JP2015074728A - Pigment dispersant, and pigment composition, coloring composition and color filter using the same - Google Patents

Abstract

PROBLEM TO BE SOLVED: To provide a pigment dispersant that exhibits an extremely good characteristic in enhancing the dispersibility of pigment, to provide a pigment composition, produced by using the pigment dispersant, that is excellent in the contrast ratio and the luminance, has a good heat resistance and light stability, and does not generate a coated film foreign body, as well as to provide a coloring composition having an extremely good dispersibility stability.SOLUTION: The problem is solved by a naphthol azo-based pigment dispersant having a particular structure represented by a general formula (1) or a general formula (2), and by a pigment composition, coloring composition and color filter that are produced using the pigment dispersant.

Description

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

  Examples of color display devices using color filters include (i) a backlight as a light source, a liquid crystal as an optical shutter, and a combination of color filters having color adjustment functions (color conversion function, color separation function, color correction function, etc.) And (ii) a synthetic white organic EL light source, and an organic EL display device comprising a combination of color filters having a color adjustment function (color conversion function, color separation function, color correction function, etc.).

  A color filter has two or more kinds of fine band (striped) filter segments arranged in parallel or intersecting with each other on the surface of a transparent substrate such as glass, or the fine filter segments are arranged vertically and horizontally. It is made up of those arranged in The filter segments are as fine as several microns to several hundreds of microns, and are regularly arranged in a predetermined arrangement for each hue.

  In general, a color filter is produced by using a coloring composition in which a pigment is dispersed and a photocurable coloring composition containing a polyfunctional monomer, a polymerization initiator, an alkali-soluble resin and other components. In addition, a method of forming a colored pattern and a black matrix through a high temperature treatment process of 230 ° C. or higher is the mainstream.

  At present, the liquid crystal display (i) is mainly used as the flat panel display, and it is rapidly spreading as a home TV, a monitor for a personal computer, a tablet terminal and a smartphone because of low power consumption and space saving. Along with this widespread use, in particular, there is a demand for higher brightness year by year, and in the color filter that is a constituent member, improvement in transmittance is desired. When a color filter with low luminance is used, the light transmittance is low, resulting in a dark screen. In order to obtain a bright screen, it is necessary to increase the number of backlights that are light sources. For this reason, from the viewpoint of suppressing an increase in power consumption, increasing the brightness of color filters has become a trend.

  In order to increase the luminance, it is necessary to design a pigment composition having an optimal spectral shape. For example, in the case of red, in the transmission spectrum of the color filter, the transmittance from around 560 nm to the longer wavelength side is increased. There is a need.

  In television applications, color reproducibility is also important. The color reproducibility of the color liquid crystal display device is determined by the color of light emitted from the red, green, and blue filter segments, and the chromaticity points of the respective filter segments are (xR, yR), (xG, yG), (XB, yB) is evaluated by the area of a triangle surrounded by these three points on the xy chromaticity diagram, and the standard three primary colors defined by the US National Television System Committee (NTSC), red ( 0.67, 0.33), ratio to the area surrounded by green (0.21, 0.71), blue (0.14, 0.08) (unit is%, hereinafter abbreviated as NTSC ratio). Is done. This value is 40 to 100% for a general notebook computer, 50 to 100% for a monitor for a personal computer, and 70% to 100% for a liquid crystal television.

As the backlight in the liquid crystal display device of (i), a cold cathode tube type backlight, a two-wavelength peak pseudo-white backlight and a three-wavelength peak backlight using a light emitting diode or an organic EL element using an inorganic material. and so on. In the liquid crystal display device, a liquid crystal layer sandwiched between two polarizing plates controls the amount of light passing through the first polarizing plate by controlling the degree of polarization of light passing through the first polarizing plate. The VA mode, the IPS mode, etc., and the type using a TN (twisted nematic) mode type liquid crystal is the mainstream. However, these liquid crystal display devices have a problem that energy is wasted because the backlight unit continues to emit the same light as white display even in black display.

  In a color liquid crystal display device, since a structure in which a liquid crystal layer and a color filter are sandwiched between two polarizing plates is the mainstream, the contrast ratio of the color filter is also an important quality item. When a color filter with a low contrast ratio is used, the polarization plane of the light transmitted through the light plate is disturbed, and when light must be blocked (OFF state) or when light must be transmitted or transmitted Since the transmitted light attenuates in the (ON state), the screen becomes blurred. Therefore, in order to realize a high-quality liquid crystal display device, high contrast is indispensable.

  The reason why the polarization plane of the light transmitted through the first polarizing plate is disturbed by the color filter is that the light polarized by the first polarizing plate is reflected on the pigment surface when passing through the color filter, and polarized. It is thought that the plane is rotated and the polarized light is broken (depolarization).

  Therefore, in order to increase the contrast ratio of a color liquid crystal display, the primary particles of the pigment contained in the color filter are made finer and made smaller than the wavelength of the light, and the refractive index difference between the pigment and the medium is changed. It is important to make it smaller. In general, the primary particles of the pigment are miniaturized by subjecting the pigment to mechanical pulverization (see Patent Documents 1 and 2).

  Therefore, if a pigment having an appropriate spectral region can be refined and a good dispersion state can be obtained by using a pigment dispersant having high refining ability and dispersibility, the luminance and contrast ratio can be improved.

  Conventionally, the red filter segment, which is one of the three primary colors (red, green, blue; RGB) of the color filter substrate, is a diketopyrrolopyrrole pigment C.I. I. Pigment Red 254 and C.I. an anthraquinone pigment. I. Pigment Red 177 is used alone or in combination.

  C. I. Pigment Red 254 is a pigment particularly excellent in luminance, but has a problem in heat resistance of the fine pigment, and has a problem that luminance is lowered in a color filter using the pigment. In addition, C.I. I. Pigment Red 177 has good heat resistance and light resistance, but has a problem of low brightness.

  As the synthetic white light source of the organic EL display device of (ii), there are a light source having a two-wavelength peak, a light source having a three-wavelength peak, and a light source having a large number of peaks in the visible light region. Synthetic white light is obtained by mixing or layering.

  Since the organic EL display device can directly turn on / off the light source of the pixel by a TFT (thin film transistor) or the like, it is possible to perform black display by turning off the light emission of the designated pixel. Therefore, the deflecting plate used in the liquid crystal display device is not required in the light emitting device, and it is not necessary to control the liquid crystal body. For this reason, the amount of transmitted light in the display device increases, and energy consumption can be greatly reduced by turning off the light emitting device in black display. In addition, it is possible to reproduce true dark black, and the contrast ratio can be increased. As an organic EL color display device in which the problems in the liquid crystal display device are solved, for example, a product such as “XEL-1” manufactured by SONY is already on the market. (For example, see Patent Document 3)

However, a light emitting device using such an organic EL element has a light emission spectrum different from that of a conventionally used light source. For example, a conventional light source has a peak in the vicinity of 420 to 430 nm, but a light source using an organic EL element has no peak in the vicinity of 420 to 430 nm due to the characteristics of the material, and has a peak in the vicinity of 460 nm. In addition, the emission spectrum of the light source using the organic EL element has a broad peak as compared with the conventional light source, and therefore, even after passing the peak around 460 nm, the conventional light source reaches about 500 nm. The spectrum is higher. For these reasons, currently used color filters cannot be used as they are in display devices using light sources using organic EL elements. For this reason, it is necessary to select and develop a color filter material that can be used for a light source using an organic EL element and has an optimum hue and transmittance characteristics.

An organic EL display device having such a light source is also required to have a high NTSC ratio, as in a liquid crystal display device. In order to increase the NTSC ratio, it is necessary to increase the color purity of each filter segment. However, if the color purity is increased, the light use efficiency (represented by the luminance Y value) of the light source decreases, so that power consumption is reduced. There is a problem that increases.

  In order to obtain a color filter having a large NTSC ratio, C.I. I. Pigment red 177, C.I. I. Pigment Red 179, a red pigment, and C.I. I. Pigment yellow 185, C.I. I. Often yellow pigments such as CI Pigment Yellow 139 are used.

Here, when the above pigments are used alone or in combination, there is a problem that the luminance is low.

  In Patent Documents 4 to 6, in order to further improve the luminance of the red filter segment, C.I. I. Pigment red 176, C.I. I. Pigment red 242, and C.I. I. Although it has been proposed to use an azo pigment such as CI Pigment Orange 38 as a main pigment, brightness and color purity are not sufficient, and further improvement has been demanded. Furthermore, Patent Document 7 discloses a novel azo compound, but its action as a pigment dispersant is not known.

JP 2001-220520 A JP 2005-189672 A Japanese Patent Laid-Open No. 2005-10091 JP 2009-237462 A Japanese Patent Laid-Open No. 11-14824 Japanese Patent Laid-Open No. 10-115709 JP 2011-173971 A

  The problem to be solved by the present invention is to provide a pigment dispersant exhibiting extremely excellent characteristics for improving the dispersibility of the pigment. Furthermore, when producing a color filter using a pigment composition or a coloring composition using the same, the pigment composition is excellent in contrast ratio and luminance, heat resistance and light resistance, and does not generate a coating film foreign matter. Another object of the present invention is to provide a coloring composition having extremely excellent dispersibility stability.

  As a result of intensive studies, the present inventors have found that a pigment dispersant having a specific structure can solve the above problems, and have reached the present invention.

  That is, the present invention relates to a pigment dispersant represented by the following general formula (1) or general formula (2).

[In the general formula ^(1), X 1 ~X ⁵ each independently represent a hydrogen atom, a halogen atom, an alkyl group or an alkoxyl group. X ⁶ is a hydrogen atom, a halogen atom, an alkyl group, or an alkoxyl group. X ^{7 to} X ⁹ are each independently a hydrogen atom or a group represented by the following formula (a), (c) or (d), and at least one of X ^{7 to} X ⁹ is represented by the formula (a ), (C) or (d). X ¹⁰ is a hydrogen atom.
In the general formula (2), X ^{11 to} X ¹⁵ are each independently a hydrogen atom, a halogen atom, an alkyl group, a perfluoroalkyl group, or an alkoxyl group, and at least one of X ^{11 to} X ¹⁵ is a per A fluoroalkyl group; X ¹⁶ is a halogen atom or an alkyl group. X ^{17 to} X ¹⁹ are each independently a hydrogen atom or a group represented by the following formula (a), (c) or (d), and at least one of X ^{17 to} X ¹⁹ is represented by the formula (a ), (C) or (d). X ²⁰ is a hydrogen atom. ]

[In the formula (a), Z ¹ is CO or a direct bond, Z ² is NH or O, n is an integer of 1 to 10, and R ¹⁶ and R ¹⁷ are alkyl groups. . ]

[In Formula (c), Z ⁴ represents CO or a direct bond, Z ⁵ represents NH, and R ²³ represents a group represented by Formula (a). R ²⁴ is an alkoxyl group or a group represented by the formula (a). ]

[In the formula (d), Z ⁶ is CONH. R ^{25 to} R ²⁹ are a hydrogen atom, an alkoxyl group, or a group represented by formula (a) or formula (c), and at least one of R ^{25 to} R ²⁹ is represented by formula (a) or formula (c ). ]

The present invention also provides:
In the general formula (1), X ^{7 to} X ⁹ are each independently a hydrogen atom or a group represented by the following formula (a), (c) or (d), and X ⁸ or X ⁹ is a formula Is a group represented by (a), X ⁸ or X ⁹ is a group represented by formula (c), or X ⁷ and / or X ⁹ is a group represented by formula (d) And
In the general formula (2), X ^{17 to} X ¹⁹ are each independently a hydrogen atom or a group represented by the following formula (a), (c) or (d), and X ¹⁸ or X ¹⁹ is a formula Is a group represented by (a), X ¹⁸ or X ¹⁹ is a group represented by formula (c), or X ¹⁷ and / or X ¹⁹ is a group represented by formula (d) It is related with the said pigment dispersant characterized by these.

The present invention also provides:
In general formula (1), X ¹ is a hydrogen atom, an alkyl group, or an alkoxy group, X ² , X ³ , and X ⁵ are hydrogen atoms, and X ⁴ is a hydrogen atom or a halogen atom. ,
In General Formula (2), X ¹¹ is a hydrogen atom or a halogen atom, X ¹² and X ¹⁵ are hydrogen atoms, and X ¹³ and X ¹⁴ are each independently a hydrogen atom or a perfluoroalkyl group. And
In formula (d), R ²⁵ is a hydrogen atom or an alkoxyl group, R ²⁹ is a hydrogen atom, R ^{26 to} R ²⁸ are a hydrogen atom or a group represented by formula (a), At least one of R ^{26 to} R ²⁸ relates to the pigment dispersant, which is a group represented by the formula (a).

  The present invention also relates to a pigment composition comprising the pigment dispersant and a pigment.

  In the present invention, the mass ratio of the pigment dispersant represented by the general formula (1) and / or the general formula (2) to the pigment is 35:65 to 1:99. The present invention relates to a pigment composition.

  The present invention also relates to the pigment composition, wherein the pigment is an azo pigment represented by the following general formula (3).

[In General Formula (3), A represents a hydrogen atom or a phenyl group. R ¹ represents a hydrogen atom, a halogen atom, a trifluoromethyl group, an alkyl group having 1 to 4 carbon atoms, or an alkoxyl group having 1 to 4 carbon atoms. R ^{2 to} R ⁶ are each independently a hydrogen atom, a halogen atom, a cyano group, a nitro group, a trifluoromethyl group, an alkyl group having 1 to 4 carbon atoms, —OR ⁸ , —COOR ⁹ , —CONHR ¹⁰ , It represents an -NHCOR ¹¹ or -SO ₂ NHR ^12. R ⁸ to R ¹² each independently represent a hydrogen atom or an alkyl group having 1 to 4 carbon atoms. ]

  The present invention further relates to the pigment composition comprising a pigment dispersant represented by the following general formula (4) and an azo pigment represented by (5).

[In General Formula (4), X ⁶ represents a hydrogen atom, a halogen atom, an alkyl group, or an alkoxyl group. X ^{7 to} X ⁹ are each independently a hydrogen atom or a group represented by the following formula (a), (c) or (d), and at least one of X ^{7 to} X ⁹ is represented by the formula (a ), (C) or (d). X ¹⁰ is a hydrogen atom.
In general formula (5), A represents a hydrogen atom or a phenyl group. R ¹ represents a hydrogen atom, a halogen atom, a trifluoromethyl group, an alkyl group having 1 to 4 carbon atoms, or an alkoxyl group having 1 to 4 carbon atoms.

[In the formula (a), Z ¹ is CO or a direct bond, Z ² is NH or O, n is an integer of 1 to 10, and R ¹⁶ and R ¹⁷ are alkyl groups. . ]

[In Formula (c), Z ⁴ represents CO or a direct bond, Z ⁵ represents NH, and R ²³ represents a group represented by Formula (a). R ²⁴ is an alkoxyl group or a group represented by the formula (a). ]

[In the formula (d), Z ⁶ is CONH. R ^{25 to} R ²⁹ are a hydrogen atom, an alkoxyl group, or a group represented by formula (a) or formula (c), and at least one of R ^{25 to} R ²⁹ is represented by formula (a) or formula (c ). ]

The present invention also provides:
1 to 35% by weight of a pigment dispersant represented by the general formula (1) and / or the general formula (2),
The azo pigment represented by the general formula (3) is 50 to 93% by weight,
The pigment dispersant represented by the general formula (4) is 0.1 to 10% by weight,
The azo pigment represented by the general formula (5) is 5 to 25% by weight,
It is related with the said pigment composition characterized by the above-mentioned.

  The present invention also relates to a color composition containing a colorant, a binder resin, and an organic solvent, wherein the colorant contains the pigment composition.

  In addition, the present invention relates to the colored composition further comprising a photopolymerizable monomer.

  Furthermore, the present invention relates to a color filter comprising a filter segment formed from the colored composition on a substrate.

  The pigment dispersant of the present invention acts as a good dispersant for the pigment. Therefore, a pigment composition or a coloring composition using the same can provide a color filter excellent in contrast ratio and luminance, free from foreign matter on the coating film, and having good heat resistance and light resistance. The colored composition of the present invention can also be used in industrial fields such as inkjet colored compositions, printing inks, resin colorants, and paints.

  Hereinafter, the present invention will be described in detail. Note that “CI” described below means a color index (CI).

<Pigment dispersant>
First, the substituent of the pigment dispersant represented by the general formula (1) or the general formula (2) will be described.

[In the general formula ^(1), X 1 ~X ⁵ each independently represent a hydrogen atom, a halogen atom, an alkyl group or an alkoxyl group. X ⁶ is a hydrogen atom, a halogen atom, an alkyl group, or an alkoxyl group. X ^{7 to} X ⁹ are each independently a hydrogen atom or a group represented by the following formula (a), (c) or (d), and at least one of X ^{7 to} X ⁹ is represented by the formula (a ), (C) or (d). X ¹⁰ is a hydrogen atom. ]

[In the general formula (2), X ¹¹ ~X ¹⁵ each independently represent a hydrogen atom, a halogen atom, an alkyl group, a perfluoroalkyl group, an alkoxyl group, at least one of X ¹¹ to X ¹⁵ is Perfluoroalkyl group. X ¹⁶ is a halogen atom or an alkyl group. X ^{17 to} X ¹⁹ are each independently a hydrogen atom or a group represented by the following formula (a), (c) or (d), and at least one of X ^{17 to} X ¹⁹ is represented by the formula (a ), (C) or (d). X ²⁰ is a hydrogen atom. ]

[In the formula (a), Z ¹ is CO or a direct bond, Z ² is NH or O, n is an integer of 1 to 10, and R ¹⁶ and R ¹⁷ are alkyl groups. . ]

[In Formula (c), Z ⁴ represents CO or a direct bond, Z ⁵ represents NH, and R ²³ represents a group represented by Formula (a). R ²⁴ is an alkoxyl group or a group represented by the formula (a). ]

[In the formula (d), Z ⁶ is CONH. R ^{25 to} R ²⁹ are a hydrogen atom, an alkoxyl group, or a group represented by formula (a) or formula (c), and at least one of R ^{25 to} R ²⁹ is represented by formula (a) or formula (c ). ]

  Here, examples of the halogen atom include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom. Of these, a chlorine atom is particularly preferred.

  Examples of the alkyl group include methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl, tert-butyl, pentyl, isopentyl, hexyl, heptyl, octyl, An alkyl group having 1 to 8 carbon atoms such as a 2-ethylhexyl group is preferable, an alkyl group having 1 to 4 carbon atoms is more preferable, and a methyl group or an ethyl group is further preferable.

  Examples of the alkoxyl group include C1-C4 alkoxyl groups such as a methoxy group, an ethoxy group, a propoxy group, a butoxy group, and a tert-butoxy group. Of these, a methoxy group or an ethoxy group is preferable, and a methoxy group is particularly preferable.

In the general formula (1), X ¹ is preferably a hydrogen atom, an alkyl group or an alkoxyl group, particularly preferably an alkoxyl group.

In the general formula (1), X ⁴ is preferably a hydrogen atom or a halogen atom, and more preferably a chlorine atom.

In the general formula (1), X ⁶ is preferably a hydrogen atom, a halogen atom, an alkyl group or an alkoxyl group. More preferably, it is an alkyl group or an alkoxyl group.

In General Formula (1), any one of X ^{7 to} X ⁹ is preferably a group represented by Formula (a), Formula (c), or Formula (d). In a more preferred embodiment, (i): when X ⁹ is a group represented by formula (a), formula (c) or formula (d), and X ⁷ and X ⁸ are hydrogen atoms, Preferably, when it is a group represented by formula (a) or (d), (ii): X ⁸ is a group represented by formula (a) or formula (c), and X ⁷ and X ^{When 9} is a hydrogen atom, more preferably when it is a group represented by the formula (a), (iii): X ⁷ and X ⁹ are groups represented by the formula (d), and X ⁸ Is a hydrogen atom.

In the general formula (2), X ¹¹ is preferably a hydrogen atom, a halogen atom, an alkyl group, or an alkoxy group, and among these, a hydrogen atom or a halogen atom is preferable, and a halogen atom is more preferable.

In the general formula (2), X ¹³ and X ¹⁴ are each independently preferably a hydrogen atom or a perfluoroalkyl group, preferably X ¹³ is a hydrogen atom, and X ¹⁴ is a perfluoroalkyl group. A fluoromethyl group is preferred.

In General Formula (2), any one of X ^{17 to} X ¹⁹ is preferably a group represented by Formula (a), Formula (c), or Formula (d). In a more preferred embodiment, (i): when X ¹⁹ is a group represented by formula (a), formula (c) or formula (d), and X ¹⁷ and X ¹⁸ are hydrogen atoms, ii): when X ¹⁸ is a group represented by formula (a) or formula (c), and X ¹⁷ and X ¹⁹ are hydrogen atoms, (iii): X ¹⁷ and X ¹⁹ are represented by formula ( a group represented by d), and X ¹⁸ is a hydrogen atom. In a more preferred embodiment, when (iv): X ¹⁹ is a group represented by the formula (a) or (d), and X ¹⁷ and X ¹⁸ are hydrogen atoms, (v): X ¹⁸ is a group represented by the formula (a), and X ¹⁷ and X ¹⁹ are hydrogen atoms.

Here, as a preferable embodiment of the group represented by the formula (a), Z ¹ is CO, Z ² is NH,
n is an integer of 1 to 8, and R ¹⁶ and R ¹⁷ are alkyl groups having 1 to 8 carbon atoms. More preferably, n is an integer of 1 to 4, and R ¹⁶ and R ¹⁷ are alkyl groups having 1 to 4 carbon atoms.

A preferred embodiment of the group represented by the formula (c) is a case where Z ⁴ is a direct bond and R ²³ and R ²⁴ are groups represented by the formula (a).

Moreover, as a preferable embodiment of the group represented by the formula (d), R ²⁵ and R ²⁹ are hydrogen atoms, and at least one of R ^{26 to} R ²⁷ is a group represented by the formula (a). The other is a hydrogen atom. In a more preferred embodiment, when (i): R ²⁷ is a group represented by the formula (a) and R ²⁶ and R ²⁸ are hydrogen atoms, (ii): R ²⁶ is a hydrogen atom or a group represented by the formula (a ), R ²⁸ is a group represented by the formula (a), and R ²⁷ is a hydrogen atom.

  Examples of the amine component used to form the substituent represented by the above formula (a), formula (b), and formula (c) include dimethylamine, diethylamine, methylethylamine, N, N-ethyl. Isopropylamine, N, N-ethylpropylamine, N, N-methylbutylamine, N, N-methylisobutylamine, N, N-butylethylamine, N, N-tert-butylethylamine, diisopropylamine, dipropylamine, N , N-sec-butylpropylamine, dibutylamine, di-sec-butylamine, diisobutylamine, N, N-isobutyl-sec-butylamine, N, N-dimethylaminomethylamine, N, N-dimethylaminoethylamine, N, N-dimethylaminoamylamine, N, N-dimethylaminobuty Amine, N, N-diethylaminoethylamine, N, N-diethylaminopropylamine, N, N-diethylaminohexylamine, N, N-diethylaminobutylamine, N, N-diethylaminopentylamine, N, N-dipropylaminobutylamine, N , N-dibutylaminopropylamine, N, N-dibutylaminoethylamine, N, N-dibutylaminobutylamine and the like, but are not limited thereto.

Therefore, as a preferable embodiment of the general formula (1),
X ¹ is a hydrogen atom, an alkyl group or an alkoxyl group,
X ² , X ³ , X ⁵ and X ¹⁰ are hydrogen atoms;
X ⁴ is a hydrogen atom or a halogen atom,
X ⁶ is a hydrogen atom, a halogen atom, an alkyl group, or an alkoxyl group,
X ⁷ , X ⁸ and X ⁹ are a hydrogen atom, a group represented by formula (a), formula (c) or formula (d), and at least one of X ⁷ , X ⁸ and X ⁹ Is a group represented by formula (a), formula (c), or formula (d),
In the formula (a), Z ¹ is CO, Z ² is NH, n is an integer of 1 to 8, and R ¹⁶ and R ¹⁷ are alkyl groups having 1 to 8 carbon atoms. Yes,
In formula (c), Z ⁴ is a direct bond, Z ⁵ is NH, R ²³ and R ²⁴ are groups represented by formula (a),
In formula (d), Z ⁶ is CONH, R ²⁵ and R ²⁹ are hydrogen atoms, and R ²⁶ , R ²⁷ and R ²⁸ are each independently represented by a hydrogen atom or formula (a). It is preferable that at least one of R ²⁶ , R ²⁷ and R ²⁸ is a group represented by the formula (a).

Moreover, as a preferable aspect of General formula (2),
X ¹¹ is a hydrogen atom or a halogen atom,
X ¹² , X ¹³ , X ¹⁵ and X ²⁰ are hydrogen atoms;
X ¹⁴ is a hydrogen atom or a perfluoroalkyl group,
X ¹⁶ is a halogen atom or an alkyl group,
X ¹⁷ , X ¹⁸ and X ¹⁹ are a hydrogen atom, a group represented by formula (a), formula (c) or formula (d), and at least one of X ¹⁷ , X ¹⁸ and X ¹⁹ Is a group represented by formula (a), formula (c), or formula (d),
In the formula (a), Z ¹ is CO, Z ² is NH, n is an integer of 1 to 8, and R ¹⁶ and R ¹⁷ are alkyl groups having 1 to 8 carbon atoms. Yes,
In formula (c), Z ⁴ is a direct bond, Z ⁵ is NH, R ²³ and R ²⁴ are groups represented by formula (a),
In formula (d), Z ⁶ is CONH, R ²⁵ and R ²⁹ are hydrogen atoms, and R ²⁶ , R ²⁷ and R ²⁸ are each independently represented by a hydrogen atom or formula (a). It is preferable that at least one of R ²⁶ , R ²⁷ and R ²⁸ is a group represented by the formula (a).

  In addition to the method of mixing when dispersing the pigment, the pigment dispersant is added at the time of manufacturing the pigment composition, the method of synthesizing at the same time, the method of mixing in water or an organic solvent, or the salt milling process. A method is mentioned. The blending amount of the pigment dispersant is preferably in the range of 0.5 to 40 parts by mass with respect to 100 parts by mass of the pigment. More preferably, it is the range of 1-30 mass parts, Most preferably, it is the range of 1-20 mass parts.

Hereinafter, specific examples of the substituent (abbreviated as L) represented by the formula (a), the formula (b), and the formula (c) in the pigment dispersant used in the present invention will be described. However, it is not limited to these. C ₃ H ₇ and n-C ₃ H ₇ are propyl groups, i-C ₃ H ₇ is isopropyl groups, C ₄ H ₉ is butyl groups, C ₃ H ₆ is propylene groups, and C ₄ H ₈ is butylene groups. Represents.

<Pigment>
Next, the pigment used in the present invention will be described. The pigment used in the present invention may be an industry-known pigment, and may be an organic pigment or an inorganic pigment, but an organic pigment is preferred. More preferred are azo pigments and naphthol pigments, and particularly preferred are pigments represented by the general formula (3).

[In General Formula (3), A represents a hydrogen atom or a phenyl group. R ¹ represents a hydrogen atom, a halogen atom, a trifluoromethyl group, an alkyl group having 1 to 4 carbon atoms, or an alkoxyl group having 1 to 4 carbon atoms. R ^{2 to} R ⁶ are each independently a hydrogen atom, a halogen atom, a cyano group, a nitro group, a trifluoromethyl group, an alkyl group having 1 to 4 carbon atoms, —OR ⁸ , —COOR ⁹ , —CONHR ¹⁰ , It represents an -NHCOR ¹¹ or -SO ₂ NHR ^12. R ⁸ to R ¹² each independently represent a hydrogen atom or an alkyl group having 1 to 4 carbon atoms. ]

  Here, examples of the halogen atom include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom. Of these, a chlorine atom is particularly preferred.

  Examples of the alkyl group include a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, an isobutyl group, a sec-butyl group, and a tert-butyl group, and a methyl group or an ethyl group is more preferable.

  Examples of the alkoxyl group include C1-C4 alkoxyl groups such as a methoxy group, an ethoxy group, a propoxy group, a butoxy group, and a tert-butoxy group. Of these, a methoxy group or an ethoxy group is preferable, and a methoxy group is particularly preferable.

  In general formula (3), A is particularly preferably a phenyl group.

R ¹ is preferably a halogen atom, an alkyl group having 1 to 4 carbon atoms, or an alkoxyl group. A C1-C4 alkyl group and an alkoxyl group are more preferable.

R ² is more preferably a hydrogen atom, a halogen atom, an alkyl group having 1 to 4 carbon atoms, or an alkoxyl group, and particularly preferably an alkoxyl group.

R ⁵ is more preferably a hydrogen atom, a halogen atom, or a trifluoromethyl group, and particularly preferably a halogen atom.

Therefore, as a preferable embodiment of the general formula (3),
A is a hydrogen atom or a phenyl group,
R ¹ is a halogen atom, an alkyl group having 1 to 4 carbon atoms, or an alkoxyl group,
R ² is a hydrogen atom, a halogen atom, an alkyl group having 1 to 4 carbon atoms, or an alkoxyl group,
R ³ , R ⁴ and R ⁶ are hydrogen atoms;
R ⁵ is preferably a hydrogen atom, a halogen atom, or a trifluoromethyl group.
In particular, C.I. I. Pigment Red 269 is preferable.

<Pigment dispersant represented by general formula (4) and azo pigment represented by (5)>
Next, the pigment dispersant represented by the general formula (4) and the azo pigment represented by (5) used in the present invention will be described.

General formula (4)
[In General Formula (4), X ⁶ represents a hydrogen atom, a halogen atom, an alkyl group, or an alkoxyl group. X ^{7 to} X ⁹ are each independently a hydrogen atom or a group represented by the following formula (a), (c) or (d), and at least one of X ^{7 to} X ⁹ is represented by the formula (a ), (C) or (d). X ¹⁰ is a hydrogen atom. ]

[In the formula (a), Z ¹ is CO or a direct bond, Z ² is NH or O, n is an integer of 1 to 10, and R ¹⁶ and R ¹⁷ are alkyl groups. . ]

[In Formula (c), Z ⁴ represents CO or a direct bond, Z ⁵ represents NH, and R ²³ represents a group represented by Formula (a). R ²⁴ is an alkoxyl group or a group represented by the formula (a). ]

[In the formula (d), Z ⁶ is CONH. R ^{25 to} R ²⁹ are a hydrogen atom, an alkoxyl group, or a group represented by formula (a) or formula (c), and at least one of R ^{25 to} R ²⁹ is represented by formula (a) or formula (c ). ]

General formula (5)
[In General Formula (5), A represents a hydrogen atom or a phenyl group. R ¹ represents a hydrogen atom, a halogen atom, a trifluoromethyl group, an alkyl group having 1 to 4 carbon atoms, or an alkoxyl group having 1 to 4 carbon atoms. ]

  Here, examples of the halogen atom include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom. Of these, a chlorine atom is particularly preferred.

  Examples of the alkyl group include methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl, tert-butyl, pentyl, isopentyl, hexyl, heptyl, octyl, An alkyl group having 1 to 8 carbon atoms such as a 2-ethylhexyl group is preferable, an alkyl group having 1 to 4 carbon atoms is more preferable, and a methyl group or an ethyl group is further preferable.

  Examples of the alkoxyl group include C1-C4 alkoxyl groups such as a methoxy group, an ethoxy group, a propoxy group, a butoxy group, and a tert-butoxy group. Of these, a methoxy group or an ethoxy group is preferable, and a methoxy group is particularly preferable.

In the general formula (4), X ⁶ is preferably a hydrogen atom, a halogen atom, an alkyl group or an alkoxyl group. An alkyl group or an alkoxyl group is more preferable.

Moreover, it is preferable that any one of X < ⁷ > -X < ⁹ > is group represented by Formula (a), Formula (c), or Formula (d). In a more preferred embodiment, (i): when X ⁹ is a group represented by formula (a), formula (c) or formula (d), and X ⁷ and X ⁸ are hydrogen atoms, Preferably, when it is a group represented by formula (a) or (d), (ii): X ⁸ is a group represented by formula (a) or formula (c), and X ⁷ and X ^{When 9} is a hydrogen atom, more preferably when it is a group represented by the formula (a), (iii): X ⁷ and X ⁹ are groups represented by the formula (d), and X ⁸ Is a hydrogen atom.

Here, as a preferable embodiment of the group represented by the formula (a), Z ¹ is CO, Z ² is NH,
n is an integer of 1 to 8, and R ¹⁶ and R ¹⁷ are alkyl groups having 1 to 8 carbon atoms. More preferably, n is an integer of 1 to 4, and R ¹⁶ and R ¹⁷ are alkyl groups having 1 to 4 carbon atoms.

A preferred embodiment of the group represented by the formula (c) is a case where Z ⁴ is a direct bond and R ²³ and R ²⁴ are groups represented by the formula (a).

Moreover, as a preferable embodiment of the group represented by the formula (d), R ²⁵ and R ²⁹ are hydrogen atoms, and at least one of R ^{26 to} R ²⁷ is a group represented by the formula (a). The other is a hydrogen atom. In a more preferred embodiment, when (i): R ²⁷ is a group represented by the formula (a) and R ²⁶ and R ²⁸ are hydrogen atoms, (ii): R ²⁶ is a hydrogen atom or a group represented by the formula (a ), R ²⁸ is a group represented by the formula (a), and R ²⁷ is a hydrogen atom.

Therefore, as a preferable embodiment of the general formula (4),
X ⁶ is a hydrogen atom, a halogen atom, an alkyl group, or an alkoxyl group,
X ⁷ , X ⁸ and X ⁹ are a hydrogen atom, a group represented by formula (a), formula (c) or formula (d), and at least one of X ⁷ , X ⁸ and X ⁹ Is a group represented by formula (a), formula (c), or formula (d),
In the formula (a), Z ¹ is CO, Z ² is NH, n is an integer of 1 to 8, and R ¹⁶ and R ¹⁷ are alkyl groups having 1 to 8 carbon atoms. Yes,
In formula (c), Z ⁴ is a direct bond, Z ⁵ is NH, R ²³ and R ²⁴ are groups represented by formula (a),
In formula (d), Z ⁶ is CONH, R ²⁵ and R ²⁹ are hydrogen atoms, and R ²⁶ , R ²⁷ and R ²⁸ are each independently represented by a hydrogen atom or formula (a). Wherein at least one of R ²⁶ , R ²⁷ and R ²⁸ is a group represented by formula (a),
X ¹⁰ is preferably a hydrogen atom.

  In the general formula (5), A is preferably a hydrogen atom or a phenyl group, and particularly preferably a phenyl group.

R ¹ is preferably a hydrogen atom, a halogen atom, a trifluoromethyl group, an alkyl group having 1 to 4 carbon atoms, or an alkoxyl group. Furthermore, a halogen atom, a C1-C4 alkyl group, and an alkoxyl group are preferable. A C1-C4 alkyl group and an alkoxyl group are more preferable.

Therefore, as a preferable aspect of the general formula (5),
A is a hydrogen atom or a phenyl group,
R ¹ is preferably a halogen atom, an alkyl group having 1 to 4 carbon atoms, or an alkoxyl group.

The pigment dispersant represented by the general formula (4) and the azo pigment represented by (5) are synthesized at the same time when the pigment composition is produced, mixed by treatment in water or an organic solvent, salt milling The method of adding at the time of processing is mentioned. Pigment dispersant represented by formula (1) or formula (2), pigment represented by formula (3), pigment dispersant represented by formula (4), and azo pigment represented by formula (5) The amount of
Respectively, the pigment dispersant represented by the general formula (1) and / or the general formula (2) is 1 to 35% by weight,
The azo pigment represented by the general formula (3) is 50 to 93% by weight,
The pigment dispersant represented by the general formula (4) is 0.1 to 10% by weight,
The azo pigment represented by the general formula (5) is preferably 1 to 25% by weight.
The pigment dispersant represented by the general formula (1) and / or the general formula (2) is 5 to 25% by weight,
The azo pigment represented by the general formula (3) is 65 to 85% by weight,
The pigment dispersant represented by the general formula (4) is 0.1 to 5% by weight,
The azo pigment represented by the general formula (5) is more preferably 5 to 15% by weight.
In particular, the pigment dispersant represented by the general formula (1) and / or the general formula (2) is 5 to 15% by weight,
The azo pigment represented by the general formula (3) is 70 to 85% by weight,
The pigment dispersant represented by the general formula (4) is 0.1 to 3% by weight,
The azo pigment represented by the general formula (5) is preferably 5 to 10% by weight.

(Miniaturization of pigment)
In order to obtain high brightness and high contrast when the pigment composition of the present invention is a colored composition, the color filter is made fine by subjecting the pigment particles to fineness by salt milling, acid pasting treatment or the like as necessary. It can be suitably used as an application. The average primary particle diameter of the pigment obtained by TEM (transmission electron microscope) is preferably 10 nm or more in order to improve the dispersibility in the pigment carrier. Moreover, in order to obtain a filter segment with high contrast, the thickness is preferably 50 nm or less.

  Salt milling is a process in which a mixture of pigment, water-soluble inorganic salt and water-soluble organic solvent is heated using a kneader such as a kneader, two-roll mill, three-roll mill, ball mill, attritor, or sand mill. After kneading, the water-soluble inorganic salt and the water-soluble organic solvent are removed by washing with water. The water-soluble inorganic salt works as a crushing aid, and it is thought that the pigment is crushed using the high hardness of the inorganic salt during salt milling, thereby generating an active surface and causing crystal growth. Yes. Accordingly, during kneading, the pigment is crushed and crystal growth occurs simultaneously, and the primary particle diameter of the pigment obtained varies depending on the kneading conditions.

  In order to promote the crystal growth of the pigment by heating, the heating temperature is preferably 35 to 150 ° C. The kneading time for the salt milling is preferably 2 to 24 hours in view of the balance between the particle size distribution of the primary particles of the salt milled and the cost required for the salt milling.

  By optimizing the conditions for salt milling the pigment, it is possible to obtain a pigment having a sharp particle size distribution in which the primary particle diameter is very fine and the width of the distribution is wide. In particular, it is preferable to use a pigment derivative in combination.

  As the water-soluble inorganic salt used for salt milling, sodium chloride, barium chloride, potassium chloride, sodium sulfate and the like can be used, but sodium chloride (salt) is preferably used from the viewpoint of cost. The water-soluble inorganic salt is preferably used in an amount of 50 to 2000 parts by mass, and most preferably 300 to 1200 parts by mass, based on the total weight of the pigment (100% by weight) from the viewpoint of both processing efficiency and production efficiency.

  The water-soluble organic solvent functions to wet the pigment and the water-soluble inorganic salt, and is not particularly limited as long as it dissolves (mixes) in water and does not substantially dissolve the inorganic salt to be used. However, a high boiling point solvent having a boiling point of 120 ° C. or higher is preferable from the viewpoint of safety because the temperature rises during salt milling and the solvent is easily evaporated. For example, 2-methoxyethanol, 2-butoxyethanol, 2- (isopentyloxy) ethanol, 2- (hexyloxy) ethanol, diethylene glycol, diethylene glycol monoethyl ether, diethylene glycol monobutyl ether, triethylene glycol, triethylene glycol monomethyl ether, Liquid polyethylene glycol, 1-methoxy-2-propanol, 1-ethoxy-2-propanol, dipropylene glycol, dipropylene glycol monomethyl ether, dipropylene glycol monoethyl ether, liquid polypropylene glycol and the like are used. The water-soluble organic solvent is preferably used in an amount of 5 to 1000 parts by weight, and most preferably 50 to 500 parts by weight, based on the total weight of the pigment (100% by weight).

  When salt milling the pigment composition, a resin may be added as necessary. The type of resin used is not particularly limited, and natural resins, modified natural resins, synthetic resins, synthetic resins modified with natural resins, and the like can be used. The resin used is solid at room temperature, preferably insoluble in water, and more preferably partially soluble in the organic solvent. The amount of resin used is preferably in the range of 2 to 200% by weight based on the total weight of the pigment (100% by weight).

<Coloring composition>
The coloring composition of the present invention includes a pigment composition composed of a pigment dispersant represented by the general formula (1) or the formula (2) of the present invention and a pigment, a binder resin, and an organic solvent. Dispersing aids and pigments other than colorants can also be included.

<Binder resin>
The binder resin contained in the coloring composition of the present invention disperses the pigment composition and includes conventionally known thermoplastic resins and thermosetting resins.

  Examples of the thermoplastic resin include acrylic resin, butyral resin, styrene-maleic acid copolymer, chlorinated polyethylene, chlorinated polypropylene, polyvinyl chloride, vinyl chloride-vinyl acetate copolymer, polyvinyl acetate, and polyurethane resin. Polyester resins, vinyl resins, alkyd resins, polystyrene resins, polyamide resins, rubber resins, cyclized rubber resins, celluloses, polyethylene (HDPE, LDPE), polybutadiene, polyimide resins, and the like.

  When used as a color filter, the spectral transmittance is preferably 80% or more, more preferably 95% or more in the entire wavelength region of 400 to 700 nm in the visible light region. Moreover, when using with the form of an alkali image development type colored resist, it is preferable to use the alkali-soluble vinyl resin which copolymerized the acidic group containing ethylenically unsaturated monomer. In order to further improve the photosensitivity, an energy ray curable resin having an ethylenically unsaturated active double bond can also be used.

  Examples of the alkali-soluble resin obtained by copolymerizing an acidic group-containing ethylenically unsaturated monomer include resins having an acidic group such as a carboxyl group or a sulfone group. Specific examples of the alkali-soluble resin include an acrylic resin having an acidic group, an α-olefin / (anhydrous) maleic acid copolymer, a styrene / styrene sulfonic acid copolymer, an ethylene / (meth) acrylic acid copolymer, or Examples include isobutylene / (anhydrous) maleic acid copolymer. Among these, at least one resin selected from an acrylic resin having an acidic group and a styrene / styrene sulfonic acid copolymer, particularly an acrylic resin having an acidic group, is preferably used because of its high heat resistance and transparency.

  Energy ray curable resins having ethylenically unsaturated active double bonds include reactive substitution of isocyanate groups, aldehyde groups, epoxy groups, etc. on polymers having reactive substituents such as hydroxyl groups, carboxyl groups, amino groups, etc. A resin in which a photo-crosslinkable group such as a (meth) acryloyl group or a styryl group is introduced into the polymer by reacting a (meth) acrylic compound having a group or cinnamic acid is used. In addition, polymers containing acid anhydrides such as styrene-maleic anhydride copolymer and α-olefin-maleic anhydride copolymer are half-esterified with a (meth) acrylic compound having a hydroxyl group such as hydroxyalkyl (meth) acrylate. A modified version is also used.

  A thermoplastic resin having both alkali-soluble performance and energy ray curing performance is also preferable for color filter applications.

The following are mentioned as a monomer which comprises the said thermoplastic resin. For example, methyl (meth) acrylate, ethyl (meth) acrylate, n-propyl (meth) acrylate, isopropyl (meth) acrylate, n-butyl (meth) acrylate, isobutyl (meth) acrylate, t-butyl (meth) acrylate, 2-ethylhexyl (meth) acrylate, cyclohexyl (meth) acrylate, stearyl (meth) acrylate, lauryl (meth) acrylate, tetrahydrofurfuryl (meth) acrylate, isobornyl (meth) acrylate, phenyl (meth) acrylate, benzyl (meth) Acrylate, phenoxyethyl (meth) acrylate, phenoxydiethylene glycol (meth) acrylate, methoxypolypropylene glycol (meth) acrylate, or ethoxypoly Ji glycol (meth) acrylate of (meth) acrylates,
Alternatively, (meth) acrylamide (meth) acrylamide, N, N-dimethyl (meth) acrylamide, N, N-diethyl (meth) acrylamide, N-isopropyl (meth) acrylamide, diacetone (meth) acrylamide, acryloylmorpholine, etc. Acrylamides, styrenes, styrenes such as α-methylstyrene, vinyl ethers such as ethyl vinyl ether, n-propyl vinyl ether, isopropyl vinyl ether, n-butyl vinyl ether, isobutyl vinyl ether, fatty acid vinyls such as vinyl acetate or vinyl propionate Kind.

  Alternatively, cyclohexylmaleimide, phenylmaleimide, methylmaleimide, ethylmaleimide, 1,2-bismaleimide ethane 1,6-bismaleimidehexane, 3-maleimidopropionic acid, 6,7-methylenedioxy-4-methyl-3-maleimide Coumarin, 4,4′-bismaleimide diphenylmethane, bis (3-ethyl-5-methyl-4-maleimidophenyl) methane, N, N′-1,3-phenylenedimaleimide, N, N′-1,4- Phenylene dimaleimide, N- (1-pyrenyl) maleimide, N- (2,4,6-trichlorophenyl) maleimide, N- (4-aminophenyl) maleimide, N- (4-nitrophenyl) maleimide, N-benzyl Maleimide, N-bromomethyl-2,3-dichloromaleimide, N-sc N-imidyl-3-maleimidobenzoate, N-succinimidyl-3-maleimidopropionate, N-succinimidyl-4-maleimidobutyrate, N-succinimidyl-6-maleimidohexanoate, N- [4- (2-benzimidazolyl) phenyl N-substituted maleimides such as maleimide and 9-maleimide acridine.

  Examples of the thermosetting resin include epoxy resins, benzoguanamine resins, rosin-modified maleic acid resins, rosin-modified fumaric acid resins, melamine resins, urea resins, and phenol resins. Especially, an epoxy resin and a melamine resin are used more suitably from a viewpoint of heat resistance improvement.

  The weight average molecular weight (Mw) of the binder resin is preferably in the range of 5,000 to 80,000, more preferably in the range of 7,000 to 50,000 in order to disperse the pigment composition preferably. The number average molecular weight (Mn) is preferably in the range of 2,500 to 40,000, and the value of Mw / Mn is preferably 10 or less.

  Here, the weight average molecular weight (Mw) and the number average molecular weight (Mn) are connected to four separation columns in series in the gel permeation chromatography “HLC-8120GPC” manufactured by Tosoh Corporation. This is a polystyrene equivalent molecular weight measured using “TSK-GEL SUPER H5000”, “H4000”, “H3000”, and “H2000” manufactured by the company and using tetrahydrofuran as the mobile phase.

  When the binder resin is used for color filter applications, a carboxyl group that acts as an alkali-soluble group during adsorption and development in the pigment composition, an aliphatic group that serves as an affinity group for the pigment composition carrier and solvent, and an aromatic group The balance of groups is important for the dispersibility, developability, and durability of the pigment composition, and it is preferable to use a resin having an acid value of 20 to 300 mgKOH / g. When the acid value is less than 20 mgKOH / g, the solubility in the developer is poor, and it may be difficult to form a fine pattern. If it exceeds 300 mgKOH / g, a fine pattern may not remain by development.

  The binder resin can be used in an amount of 20 to 500% by mass based on the total mass of the pigment composition. If it is less than 20% by mass, the film formability and various resistances are insufficient, and if it exceeds 500% by mass, the pigment concentration is low and color characteristics may not be exhibited.

<Organic solvent>
In the colored composition of the present invention, the filter composition is sufficiently dispersed in a pigment composition carrier and applied on a substrate such as a glass substrate so that the dry film thickness is 0.2 to 5 μm. An organic solvent can be included to facilitate the formation. The organic solvent is selected in consideration of good applicability of the coloring composition, solubility of each component of the coloring composition, and safety.

  Examples of the organic solvent include ethyl lactate, benzyl alcohol, 1,2,3-trichloropropane, 1,3-butanediol, 1,3-butylene glycol, 1,3-butylene glycol diacetate, 1,4-dioxane. 2-heptanone, 2-methyl-1,3-propanediol, 3,5,5-trimethyl-2-cyclohexen-1-one, 3,3,5-trimethylcyclohexanone, ethyl 3-ethoxypropionate, 3- Methyl-1,3-butanediol, 3-methoxy-3-methyl-1-butanol, 3-methoxy-3-methylbutyl acetate, 3-methoxybutanol, 3-methoxybutyl acetate, 4-heptanone, m-xylene, m-diethylbenzene, m-dichlorobenzene, N, N-dimethylacetamide, N, N- Dimethylformamide, n-butyl alcohol, n-butylbenzene, n-propyl acetate, o-xylene, o-chlorotoluene, o-diethylbenzene, o-dichlorobenzene, p-chlorotoluene, p-diethylbenzene, sec-butylbenzene, tert-butylbenzene, γ-butyrolactone, isobutyl alcohol, isophorone, ethylene glycol diethyl ether, ethylene glycol dibutyl ether, ethylene glycol monoisopropyl ether, ethylene glycol monoethyl ether, ethylene glycol monoethyl ether acetate, ethylene glycol monotertiary butyl ether, Ethylene glycol monobutyl ether, ethylene glycol monobutyl ether acetate, ethylene glycol Monopropyl ether, ethylene glycol monohexyl ether, ethylene glycol monomethyl ether, ethylene glycol monomethyl ether acetate, diisobutyl ketone, diethylene glycol diethyl ether, diethylene glycol dimethyl ether, diethylene glycol monoisopropyl ether, diethylene glycol monoethyl ether acetate, diethylene glycol monobutyl ether, diethylene glycol monobutyl ether acetate , Diethylene glycol monomethyl ether, cyclohexanol, cyclohexanol acetate, cyclohexanone, dipropylene glycol dimethyl ether, dipropylene glycol methyl ether acetate, dipropylene glycol monoethyl ether , Dipropylene glycol monobutyl ether, dipropylene glycol monopropyl ether, dipropylene glycol monomethyl ether, diacetone alcohol, triacetin, tripropylene glycol monobutyl ether, tripropylene glycol monomethyl ether, propylene glycol diacetate, propylene glycol phenyl ether, propylene glycol Monoethyl ether, propylene glycol monoethyl ether acetate, propylene glycol monobutyl ether, propylene glycol monopropyl ether, propylene glycol monomethyl ether, propylene glycol monomethyl ether acetate, propylene glycol monomethyl ether propionate, benzyl alcohol, Louis Seo ketone, methyl cyclohexanol, acetic acid n- amyl acetate n- butyl, isoamyl acetate, isobutyl acetate, propyl acetate, and dibasic acid esters.

  Among them, since the solubility of each component of the coloring composition and the coating property are good, ethyl lactate, propylene glycol monomethyl ether acetate, propylene glycol monoethyl ether acetate, ethylene glycol monomethyl ether acetate, ethylene glycol monoethyl ether acetate, etc. It is preferable to use aromatic alcohols such as glycol acetates and benzyl alcohol and ketones such as cyclohexanone.

  These organic solvents can be used individually by 1 type or in mixture of 2 or more types. Moreover, since the organic solvent can adjust a coloring composition to an appropriate viscosity and can form the filter segment of the target uniform film thickness, 500-4000 on the basis of the total mass of a pigment composition (100 mass%). It is preferably used in an amount of mass%.

<Dispersing aid>
When dispersing the pigment composition in the pigment composition carrier, a dispersion aid such as a dye derivative, a resin-type dispersant, and a surfactant can be appropriately used. The dispersion aid is excellent in dispersion of the pigment composition and has a great effect of preventing re-aggregation of the pigment composition after dispersion. Therefore, the dispersion aid is used to disperse the pigment composition in the pigment composition carrier. When a coloring composition is used, a color filter having a high spectral transmittance (brightness) can be obtained.

(Dye derivative)
As the dye derivative used in the present invention, in addition to the pigment dispersant represented by the general formula (1) or (2), an organic pigment is used as a base skeleton, and a basic group or acidic group is added to the organic pigment by a known method. A compound into which a group or a phthalimidomethyl group is introduced can also be used. Specific examples of organic pigments include quinacridone pigments, phthalocyanine pigments, azo pigments, quinophthalone pigments, isoindoline pigments, isoindolinone pigments, quinoline pigments, diketopyrrolopyrrole pigments, and benzoimidazolone pigments. Is mentioned. Also included are light yellow aromatic polycyclic compounds such as phthalimides, naphthalenes, naphthoquinones, anthracenes, anthraquinones, etc., which are not generally called dyes. Examples of the dye derivative include JP-A 63-305173, JP-B 57-15620, JP-B 59-40172, JP-B 63-17102, JP-B 5-9469, JP-A 06-06. What is described in 306301 gazette, Unexamined-Japanese-Patent No. 2001-220520, Unexamined-Japanese-Patent No. 2003-238842 etc. can be used, These can be used individually or in mixture of 2 or more types.

  From the viewpoint of improving the dispersibility of the pigment composition, the blending amount of the pigment derivative is preferably 0.5% by weight or more, more preferably 1% by weight or more, most preferably based on the total amount of the pigment composition (100% by weight). Preferably it is 3 weight% or more. Further, from the viewpoints of heat resistance and light resistance, the total amount of the pigment composition is preferably 40% by weight or less, more preferably 35% by weight or less, based on the total amount (100% by weight).

(Resin type dispersant)
The resin-type dispersant has an affinity part for the pigment composition having the property of adsorbing to the pigment composition and a part compatible with the pigment composition carrier, and is adsorbed to the pigment composition. It serves to stabilize dispersion in the carrier. Specific examples of resin-type dispersants include polycarboxylic acid esters such as polyurethane and polyacrylate, unsaturated polyamides, polycarboxylic acids, polycarboxylic acid (partial) amine salts, polycarboxylic acid ammonium salts, and polycarboxylic acid alkylamine salts. , Polysiloxane, long-chain polyaminoamide phosphate, hydroxyl group-containing polycarboxylic acid ester, modified products thereof, amides formed by reaction of poly (lower alkyleneimine) and polyester having a free carboxyl group, and salts thereof Oil-soluble dispersants such as, (meth) acrylic acid-styrene copolymer, (meth) acrylic acid- (meth) acrylic acid ester copolymer, styrene-maleic acid copolymer, polyvinyl alcohol, polyvinylpyrrolidone, etc. Resin, water-soluble polymer, polyester, modified poly Acrylate-based, ethylene oxide / propylene oxide adduct, phosphoric ester or the like is used, they may be used alone or in combination, it is not necessarily limited thereto.

  Among the above-mentioned dispersants, the acid-base interaction with the pigment dispersant of the present invention is utilized to the maximum, and the viscosity of the coloring composition is lowered with a small amount of addition, and exhibits a high spectral transmittance. A polymer dispersant having an acidic functional group is more preferable. Particularly preferred are carboxylic acid-containing graft copolymers, acidic functional group-containing acrylic block copolymers and urethane polymer dispersants having functional groups containing sulfonic acid, carboxylic acid, phosphoric acid and the like in the side chain. The resin-type dispersant is preferably used in an amount of about 5 to 200% by weight based on the total amount of the pigment composition, and more preferably about 10 to 100% by weight from the viewpoint of film formability.

  Commercially available resin-type dispersants include Disperbyk-101, 103, 107, 108, 110, 111, 116, 130, 140, 154, 161, 162, 163, 164, 165, 166, and 170 manufactured by Big Chemie Japan. 171, 174, 180, 181, 182, 183, 184, 185, 190, 2000, 2001, 2020, 2025, 2050, 2070, 2095, 2150, 2155 or Anti-Terra-U, 203, 204, or BYK- P104, P104S, 220S, 6919, or SOLPERSE-3000, 9000, 13000, 13240, 13650, 13940, 1600 manufactured by Nihon Lubrizol Corporation, such as Lactimon, Lactimon-WS, or Bykumen. 17000, 18000, 20000, 21000, 24000, 26000, 27000, 28000, 31845, 32000, 32500, 32550, 33500, 32600, 34750, 35100, 36600, 38500, 41000, 41090, 53095, 55000, 76500, etc. EFKA-46, 47, 48, 452, 4008, 4009, 4010, 4015, 4020, 4047, 4050, 4055, 4060, 4080, 4400, 4401, 4402, 4403, 4406, 4408, 4300, 4310, manufactured by Japan 4320, 4330, 4340, 450, 451, 453, 4540, 4550, 4560, 4800, 5010, 5065, 5066, 5070, 7500, 75 4,1101,120,150,1501,1502,1503, etc., Ajinomoto Fine-Techno Co., Ltd. of AJISPER PA111, PB711, PB821, PB822, PB824, and the like.

(Surfactant)
Surfactants include sodium lauryl sulfate, polyoxyethylene alkyl ether sulfate, sodium dodecylbenzene sulfonate, alkali salt of styrene-acrylic acid copolymer, sodium stearate, sodium alkyl naphthalene sulfonate, sodium alkyl diphenyl ether disulfonate Anionic surfactants such as lauryl sulfate monoethanolamine, lauryl sulfate triethanolamine, ammonium lauryl sulfate, monoethanolamine stearate, monoethanolamine of styrene-acrylic acid copolymer, polyoxyethylene alkyl ether phosphate; Polyoxyethylene oleyl ether, polyoxyethylene lauryl ether, polyoxyethylene nonylphenyl ether, polyoxyethylene Nonionic surfactants such as alkyl ether phosphates, polyoxyethylene sorbitan monostearate and polyethylene glycol monolaurate; chaotic surfactants such as alkyl quaternary ammonium salts and their ethylene oxide adducts; alkyldimethylamino Examples include amphoteric surfactants such as alkylbetaines such as betaine acetate and alkylimidazolines, and these can be used alone or in admixture of two or more, but are not necessarily limited thereto.

  The amount of the resin-type dispersant and the surfactant added is preferably 0.1 to 55% by weight, more preferably 0.1 to 45% by weight based on the total amount of the pigment composition (100% by weight). %. When the blending amount of the resin-type dispersant and the surfactant is less than 0.1% by weight, it is difficult to obtain the added effect. When the blending amount is more than 55% by weight, the dispersion is adversely affected by the excessive dispersant. May affect.

<Other pigments>
In the colored composition of the present invention, the following pigments or dyes may be used in combination so as not to impair the effects of the present invention, for example, in order to adjust chromaticity.

For example, C.I. I. Pigment Red 7, 14, 41, 48: 1, 48: 2, 48: 3, 48: 4, 57: 1, 81, 81: 1, 81: 2, 81: 3, 81: 4, 122, 146, 168, 169, 176, 177, 178, 179, 184, 185, 187, 200, 202, 208, 210, 246, 254, 255, 264, 270, 272, 273, 274, 276, 277, 278, 279, Mention may be made of red pigments such as 280, 281, 282, 283, 284, 285, 286 or 287. Examples of red dyes include xanthene series, azo series (pyridone series, barbituric acid series, metal complex series, etc.), disazo series, anthraquinone series, cyanine series, and the like. Xanthene dyes are particularly preferred. Specifically, as the xanthene oil-soluble dye, CI Solvent Red 35, CI Solvent Red 36, CI Solvent Red 42, CI Solvent Red 43, CI Solvent Red Red 44, CI Solvent Red 45, CI Solvent Red 46, CI Solvent Red 47, CI Solvent Red 48, CI Solvent Red 49, CI Solvent Red 72 CI Solvent Red 73, CI Solvent Red 109, CI Solvent Red 140, CI Solvent Red 141, CI Solvent Red 237, CI Solvent Red 246, C I. Solvent Violet 2, C.I. Solvent Violet 10, etc.
Examples of xanthene acid dyes include C.I. I. Acid Red 51, C.I. I. Acid Red 52, C.I. I. Acid Red 87, C.I. I. Acid Red 92, C.I. I. Acid Red 289, C.I. I. Acid Red 388, Rose Bengal B, Acid Rhodamine G, C.I. I. Acid Violet 9 etc.
Examples of xanthene basic dyes include C.I. I. Basic Red 1, C.I. I. Basic Red 8, C.I. I. Basic violet 10 and the like.

  In addition, C.I. I. Pigment Orange 38, 43, 71, or 73, such as an orange pigment or C.I. I. Pigment Yellow 1, 2, 3, 4, 5, 6, 10, 12, 13, 14, 15, 16, 17, 18, 24, 31, 32, 34, 35, 35: 1, 36, 36: 1, 37, 37: 1, 40, 42, 43, 53, 55, 60, 61, 62, 63, 65, 73, 74, 77, 81, 83, 93, 94, 95, 97, 98, 100, 101, 104, 106, 108, 109, 110, 113, 114, 115, 116, 117, 118, 119, 120, 123, 126, 127, 128, 129, 138, 139, 147, 150, 151, 152, 153, 154, 155, 156, 161, 162, 164, 166, 167, 168, 169, 170, 171, 172, 173, 174, 175, 176, 177, 179, 180, 181 182,185,187,188,193,194,198,199,213,214,218,219,220, or a yellow pigment 221 and the like can be used in combination. Examples of the orange dye or yellow dye include quinoline series, azo series (pyridone series, barbituric acid series, metal complex series, etc.), disazo series, and methine series.

  Preferred dyes to be used in combination include azo dyes, naphtholazo dyes, diketopyrrolopyrrole dyes, anthraquinone dyes, quinophthalone dyes, and perylene dyes from the viewpoint of color characteristics. Specifically, C.I. I. Pigment Red 254, brominated diketopyrrolopyrrole pigment, C.I. I. Pigment yellow 138, 139, 150, 185.

<Method for producing colored composition>
The coloring composition of the present invention is prepared by mixing a pigment composition with a binder resin, an organic solvent, and, if necessary, a dispersion aid or other coloring matter, a kneader, a two-roll mill, a three-roll mill, a ball mill, It can be produced by finely dispersing using various dispersing means such as a horizontal sand mill, a vertical sand mill, an annular bead mill, or an attritor. In the colored composition of the present invention, the pigment composition and other dyes may be simultaneously dispersed in the pigment composition carrier, or those separately dispersed in the pigment composition carrier may be mixed.

(Photosensitive coloring composition)
The colored composition of the present invention can be used as a photosensitive colored composition by further adding a photopolymerizable monomer.

<Photopolymerizable monomer>
Photopolymerizable monomers that may be added to the photosensitive coloring composition of the present invention include monomers or oligomers that are cured by ultraviolet rays or heat to produce a transparent resin.

Examples of monomers and oligomers that are cured by ultraviolet rays or heat to produce a transparent resin include methyl (meth) acrylate, ethyl (meth) acrylate, 2-hydroxyethyl (meth) acrylate, and 2-hydroxypropyl (meth) acrylate. , Cyclohexyl (meth) acrylate, β-carboxyethyl (meth) acrylate, polyethylene glycol di (meth) acrylate, 1,6-hexanediol di (meth) acrylate, triethylene glycol di (meth) acrylate, tripropylene glycol di ( (Meth) acrylate, trimethylolpropane tri (meth) acrylate, pentaerythritol tri (meth) acrylate, pentaerythritol tetra (meth) acrylate, 1,6-hexanediol diglycy Luether di (meth) acrylate, bisphenol A diglycidyl ether di (meth) acrylate, neopentyl glycol diglycidyl ether di (meth) acrylate, dipentaerythritol hexa (meth) acrylate, dipentaerythritol penta (meth) acrylate, tricyclodeca Nyl (meth) acrylate, ester acrylate, methylolated melamine (meth) acrylate ester, epoxy (meth) acrylate, urethane acrylate and other acrylic esters and methacrylate esters, (meth) acrylic acid, styrene, vinyl acetate, Hydroxyethyl vinyl ether, ethylene glycol divinyl ether, pentaerythritol trivinyl ether, (meth) acrylamide, N-hydroxymethyl Examples include, but are not necessarily limited to, til (meth) acrylamide, N-vinylformamide, acrylonitrile and the like.
These photopolymerizable compounds can be used singly or in combination of two or more at any ratio as required.

  The blending amount of the photopolymerizable monomer is preferably 5 to 400 parts by weight with respect to 100 parts by weight of the pigment composition, and more preferably 10 to 300 parts by weight from the viewpoint of photocurability and developability. preferable.

<Photopolymerization initiator>
In the photosensitive coloring composition of the present invention, the composition is cured by ultraviolet irradiation, and a photopolymerization initiator is added as necessary to form a filter segment by a photolithography method. It can be prepared in the form of a type photosensitive coloring composition.

Examples of the photopolymerization initiator include 4-phenoxydichloroacetophenone, 4-t-butyl-dichloroacetophenone, diethoxyacetophenone, 1- (4-isopropylphenyl) -2-hydroxy-2-methylpropan-1-one, 1- Hydroxycyclohexyl phenyl ketone, 2-methyl-1- [4- (methylthio) phenyl] -2-morpholinopropan-1-one, 2- (dimethylamino) -2-[(4-methylphenyl) methyl] -1 Acetophenone compounds such as-[4- (4-morpholinyl) phenyl] -1-butanone or 2-benzyl-2-dimethylamino-1- (4-morpholinophenyl) -butan-1-one; benzoin, benzoin Methyl ether, benzoin ethyl ether, benzoin isopropyl ether, or Benzoin compounds such as dimethyl dimethyl ketal; benzophenone, benzoylbenzoic acid, methyl benzoylbenzoate, 4-phenylbenzophenone, hydroxybenzophenone, acrylated benzophenone, 4-benzoyl-4'-methyldiphenyl sulfide, or 3,3 ', 4 Benzophenone compounds such as 4,4'-tetra (t-butylperoxycarbonyl) benzophenone; thioxanthone, 2-chlorothioxanthone, 2-methylthioxanthone, isopropylthioxanthone, 2,4-diisopropylthioxanthone, 2,4-diethylthioxanthone, etc. 2,4,6-trichloro-s-triazine, 2-phenyl-4,6-bis (trichloromethyl) -s-triazine, 2- (p-methoxyphenyl) Nyl) -4,6-bis (trichloromethyl) -s-triazine, 2- (p-tolyl) -4,6-bis (trichloromethyl) -s-triazine, 2-piperonyl-4,6-bis (trichloro Methyl) -s-triazine, 2,4-bis (trichloromethyl) -6-styryl-s-triazine, 2- (naphth-1-yl) -4,6-bis (trichloromethyl) -s-triazine, 2 -(4-Methoxy-naphth-1-yl) -4,6-bis (trichloromethyl) -s-triazine, 2,4-trichloromethyl- (piperonyl) -6-triazine, or 2,4-trichloromethyl- Triazine compounds such as (4′-methoxystyryl) -6-triazine; 1,2-octanedione, 1- [4- (phenylthio)-, 2- (O-benzoyloxime)] Or an oxime ester compound such as O- (acetyl) -N- (1-phenyl-2-oxo-2- (4′-methoxy-naphthyl) ethylidene) hydroxylamine; bis (2,4,6-trimethylbenzoyl) Phosphine compounds such as phenylphosphine oxide or 2,4,6-trimethylbenzoyldiphenylphosphine oxide; quinone compounds such as 9,10-phenanthrenequinone, camphorquinone and ethylanthraquinone; borate compounds; carbazole compounds; An imidazole compound; or a titanocene compound or the like is used.
These photoinitiators can be used individually by 1 type or in mixture of 2 or more types by arbitrary ratios as needed.

  The content of the photopolymerization initiator is preferably 2 to 200 parts by weight with respect to 100 parts by weight of the pigment composition, and more preferably 3 to 150 parts by weight from the viewpoint of photocurability and developability.

<Sensitizer>
Furthermore, the photosensitive coloring composition of the present invention can contain a sensitizer.
Sensitizers include chalcone derivatives, unsaturated ketones such as dibenzalacetone, 1,2-diketone derivatives such as benzyl and camphorquinone, benzoin derivatives, fluorene derivatives, naphthoquinone derivatives, anthraquinone derivatives , Xanthene derivatives, thioxanthene derivatives, xanthone derivatives, thioxanthone derivatives, coumarin derivatives, ketocoumarin derivatives, cyanine derivatives, merocyanine derivatives, oxonol derivatives, and other polymethine dyes, acridine derivatives, azine derivatives, thiazine derivatives, oxazine derivatives, indoline derivatives, Azulene derivatives, azurenium derivatives, squarylium derivatives, porphyrin derivatives, tetraphenylporphyrin derivatives, triarylmethane derivatives, tetrabenzoporphyrin derivatives, Trapirazinoporphyrazine derivatives, phthalocyanine derivatives, tetraazaporphyrazine derivatives, tetraquinoxalyloporphyrazine derivatives, naphthalocyanine derivatives, subphthalocyanine derivatives, pyrylium derivatives, thiopyrylium derivatives, tetraphylline derivatives, annulene derivatives, spiropyran derivatives, spirooxazine Derivatives, thiospiropyran derivatives, metal arene complexes, organoruthenium complexes, or Michler's ketone derivatives, α-acyloxy esters, acylphosphine oxides, methylphenylglyoxylate, benzyl, 9,10-phenanthrenequinone, camphorquinone, ethyl Anthraquinone, 4,4'-diethylisophthalophenone, 3,3 ', or 4,4'-tetra (t-butylperoxycarbonyl) benzopheno And 4,4′-diethylaminobenzophenone.
These sensitizers can be used singly or in combination of two or more at any ratio as necessary.

  More specifically, edited by Shin Okawara et al., “Dye Handbook” (1986, Kodansha), edited by Shin Okawara et al., “Chemistry of Functional Dye” (1981, CMC), edited by Tadasaburo Ikemori et al. Examples include, but are not limited to, sensitizers described in "Special Functional Materials" (1986, CMC). In addition, a sensitizer that absorbs light from the ultraviolet region to the near infrared region can also be contained.

  The content of the sensitizer is preferably 3 to 60 parts by weight with respect to 100 parts by weight of the photopolymerization initiator contained in the photosensitive coloring composition, and 5 to 50 from the viewpoint of photocurability and developability. More preferred are parts by weight.

<Amine compound>
Moreover, the photosensitive coloring composition of the present invention can contain an amine compound having a function of reducing dissolved oxygen.

  Such amine compounds include triethanolamine, methyldiethanolamine, triisopropanolamine, methyl 4-dimethylaminobenzoate, ethyl 4-dimethylaminobenzoate, isoamyl 4-dimethylaminobenzoate, 2-dimethylaminobenzoate. Examples include ethyl, 2-ethylhexyl 4-dimethylaminobenzoate, and N, N-dimethylparatoluidine.

<Leveling agent>
In order to improve the leveling property of the composition on the transparent substrate, it is preferable to add a leveling agent to the photosensitive coloring composition of the present invention. As the leveling agent, dimethylsiloxane having a polyether structure or a polyester structure in the main chain is preferable. Specific examples of dimethylsiloxane having a polyether structure in the main chain include FZ-2122 manufactured by Toray Dow Corning, BYK-333 manufactured by Big Chemie. Specific examples of dimethylsiloxane having a polyester structure in the main chain include BYK-310 and BYK-370 manufactured by BYK Chemie. Dimethylsiloxane having a polyether structure in the main chain and dimethylsiloxane having a polyester structure in the main chain can be used in combination. In general, the leveling agent content is preferably 0.003 to 0.5% by weight based on the total weight of the photosensitive coloring composition (100% by weight).

  Particularly preferred as a leveling agent is a type of so-called surfactant having a hydrophobic group and a hydrophilic group in the molecule, and having a hydrophilic group but low solubility in water, and when added to a photosensitive coloring composition It has the characteristics that its surface tension lowering ability is low, and it is useful to have good wettability to the glass plate despite its low surface tension lowering ability, and it does not cause coating film defects due to foaming Those that can sufficiently suppress chargeability in terms of amount can be preferably used. As a leveling agent having such preferable characteristics, dimethylpolysiloxane having a polyalkylene oxide unit can be preferably used. Examples of the polyalkylene oxide unit include a polyethylene oxide unit and a polypropylene oxide unit, and dimethylpolysiloxane may have both a polyethylene oxide unit and a polypropylene oxide unit.

  In addition, the bonding form of the polyalkylene oxide unit with dimethylpolysiloxane includes a pendant type in which the polyalkylene oxide unit is bonded in the repeating unit of dimethylpolysiloxane, a terminal-modified type in which the end of dimethylpolysiloxane is bonded, and dimethylpolysiloxane. Any of linear block copolymer types in which they are alternately and repeatedly bonded may be used. Dimethylpolysiloxane having a polyalkylene oxide unit is commercially available from Toray Dow Corning Co., Ltd., for example, FZ-2110, FZ-2122, FZ-2130, FZ-2166, FZ-2191, FZ-2203, FZ. -2207, but is not limited thereto.

An anionic, cationic, nonionic or amphoteric surfactant can be supplementarily added to the leveling agent. Two or more kinds of surfactants may be mixed and used.
Anionic surfactants added to the leveling agent as auxiliary agents include polyoxyethylene alkyl ether sulfate, sodium dodecylbenzene sulfonate, alkali salt of styrene-acrylic acid copolymer, sodium alkyl naphthalene sulfonate, alkyl diphenyl ether disulfonic acid Sodium, lauryl sulfate monoethanolamine, lauryl sulfate triethanolamine, ammonium lauryl sulfate, monoethanolamine stearate, sodium stearate, sodium lauryl sulfate, monoethanolamine of styrene-acrylic acid copolymer, polyoxyethylene alkyl ether phosphate Examples include esters.

  Examples of the chaotic surfactant that is supplementarily added to the leveling agent include alkyl quaternary ammonium salts and their ethylene oxide adducts. Nonionic surfactants added to the leveling agent as auxiliary agents include polyoxyethylene oleyl ether, polyoxyethylene lauryl ether, polyoxyethylene nonylphenyl ether, polyoxyethylene alkyl ether phosphate ester, polyoxyethylene sorbitan monostearate And amphoteric surfactants such as alkyl dimethylamino acetic acid betaine and alkylimidazolines, and fluorine-based and silicone-based surfactants.

<Curing agent, curing accelerator>
Moreover, in order to assist hardening of a thermosetting resin, the photosensitive coloring composition of this invention may contain the hardening | curing agent, the hardening accelerator, etc. as needed. As the curing agent, phenolic resins, amine compounds, acid anhydrides, active esters, carboxylic acid compounds, sulfonic acid compounds and the like are effective, but are not particularly limited to these, and thermosetting resins. Any curing agent may be used as long as it can react with the. Among these, a compound having two or more phenolic hydroxyl groups in one molecule and an amine curing agent are preferable. Examples of the curing accelerator include amine compounds (for example, dicyandiamide, benzyldimethylamine, 4- (dimethylamino) -N, N-dimethylbenzylamine, 4-methoxy-N, N-dimethylbenzylamine, 4-methyl). -N, N-dimethylbenzylamine etc.), quaternary ammonium salt compounds (eg triethylbenzylammonium chloride etc.), blocked isocyanate compounds (eg dimethylamine etc.), imidazole derivative bicyclic amidine compounds and salts thereof (eg Imidazole, 2-methylimidazole, 2-ethylimidazole, 2-ethyl-4-methylimidazole, 2-phenylimidazole, 4-phenylimidazole, 1-cyanoethyl-2-phenylimidazole, 1- (2-cyanoethyl) -2- Til-4-methylimidazole, etc.), phosphorus compounds (eg, triphenylphosphine, etc.), guanamine compounds (eg, melamine, guanamine, acetoguanamine, benzoguanamine, etc.), S-triazine derivatives (eg, 2,4-diamino-6) -Methacryloyloxyethyl-S-triazine, 2-vinyl-2,4-diamino-S-triazine, 2-vinyl-4,6-diamino-S-triazine isocyanuric acid adduct, 2,4-diamino-6 Methacryloyloxyethyl-S-triazine / isocyanuric acid adduct, etc.) can be used. These may be used alone or in combination of two or more. As content of the said hardening accelerator, 0.01-15 weight part is preferable with respect to 100 weight part of thermosetting resins.

<Other additive components>
The photosensitive coloring composition of the present invention can contain a storage stabilizer in order to stabilize the viscosity with time. Moreover, in order to improve adhesiveness with a transparent substrate, adhesion improving agents, such as a silane coupling agent, can also be contained.

  Examples of storage stabilizers include quaternary ammonium chlorides such as benzyltrimethyl chloride and diethylhydroxyamine, organic acids such as lactic acid and oxalic acid, and methyl ethers thereof, t-butylpyrocatechol, tetraethylphosphine, and tetraphenylphosphine. Organic phosphines, phosphites and the like can be mentioned. The storage stabilizer can be used in an amount of 0.1 to 10 parts by weight with respect to 100 parts by weight of the colorant.

  Examples of the adhesion improver include vinyl silanes such as vinyltris (β-methoxyethoxy) silane, vinylethoxysilane and vinyltrimethoxysilane, (meth) acrylsilanes such as γ-methacryloxypropyltrimethoxysilane, β- (3, 4-epoxycyclohexyl) ethyltrimethoxysilane, β- (3,4-epoxycyclohexyl) methyltrimethoxysilane, β- (3,4-epoxycyclohexyl) ethyltriethoxysilane, β- (3,4-epoxycyclohexyl) Epoxysilanes such as methyltriethoxysilane, γ-glycidoxypropyltrimethoxysilane, γ-glycidoxypropyltriethoxysilane, N-β (aminoethyl) γ-aminopropyltrimethoxysilane, N-β (amino Ethyl) γ-aminopropyltrie Xisilane, N-β (aminoethyl) γ-aminopropylmethyldiethoxysilane, γ-aminopropyltriethoxysilane, γ-aminopropyltrimethoxysilane, N-phenyl-γ-aminopropyltrimethoxysilane, N-phenyl Examples include silane coupling agents such as aminosilanes such as -γ-aminopropyltriethoxysilane, and thiosilanes such as γ-mercaptopropyltrimethoxysilane and γ-mercaptopropyltriethoxysilane. The adhesion improver can be used in an amount of 0.01 to 10 parts by weight, preferably 0.05 to 5 parts by weight, with respect to 100 parts by weight of the colorant in the photosensitive coloring composition.

<Removal of coarse particles>
The colored composition and the photosensitive colored composition of the present invention are 5 μm or larger coarse particles, preferably 1 μm or larger coarse particles, more preferably 0.8 μm, by means such as centrifugation, filtration with a sintered filter or a membrane filter. It is preferable to remove coarse particles of 5 μm or more and mixed dust. Thus, it is preferable that a coloring composition and a photosensitive coloring composition do not contain a particle | grain of 0.5 micrometer or more substantially. More preferably, it is 0.3 μm or less.

<Color filter>
Next, the color filter of the present invention will be described. The color filter of the present invention comprises a red filter segment, a green filter segment, and a blue filter segment, and the red filter segment therein contains the azo pigment of the present invention or a photosensitive coloring composition. Formed from things.

  The green filter segment can be formed using a normal green coloring composition or a green photosensitive coloring composition containing a green pigment and a pigment carrier. Examples of the green pigment include C.I. I. Pigment Green 7, 10, 36, 37, 58, etc. are used. Blue pigments such as aluminum phthalocyanine can also be used.

  Moreover, a yellow pigment can be used together with a green coloring composition or a green photosensitive coloring composition. Examples of yellow pigments that can be used in combination include C.I. I. Pigment Yellow 1, 2, 3, 4, 5, 6, 10, 12, 13, 14, 15, 16, 17, 18, 24, 31, 32, 34, 35, 35: 1, 36, 36: 1, 37, 37: 1, 40, 42, 43, 53, 55, 60, 61, 62, 63, 65, 73, 74, 77, 81, 83, 93, 94, 95, 97, 98, 100, 101, 104, 106, 108, 109, 110, 113, 114, 115, 116, 117, 118, 119, 120, 123, 126, 127, 128, 129, 138, 139, 147, 150, 151, 152, 153, 154, 155, 156, 161, 162, 164, 166, 167, 168, 169, 170, 171, 172, 173, 174, 175, 176, 177, 179, 180, 181 182,185,187,188,193,194,198,199,213,214,218,219,220, or it can be given a yellow pigment 221, and the like. Further, a basic dye exhibiting yellow and a salt-forming compound of an acid dye can be used in combination.

  The blue filter segment can be formed using a normal blue coloring composition or a blue photosensitive coloring composition containing a blue pigment and a pigment carrier. Examples of blue pigments include C.I. I. Pigment Blue 15, 15: 1, 15: 2, 15: 3, 15: 4, 15: 6, 16, 22, 60, 64, etc. are used. A purple pigment can be used in combination with the blue coloring composition or the blue photosensitive coloring composition. Examples of purple pigments that can be used in combination include C.I. I. And violet pigments such as CI Pigment Violet 1, 19, 23, 27, 29, 30, 32, 37, 40, 42, and 50. In addition, a basic dye or a salt-forming compound of an acid dye exhibiting blue or purple can be used. When using a dye, a xanthene dye is preferable in terms of heat resistance and luminance.

(Color filter manufacturing method)
The color filter of the present invention can be produced by a printing method or a photolithography method.

  The formation of the filter segment by the printing method can be patterned simply by repeating the printing and drying of the coloring composition prepared as the printing ink. Therefore, the color filter manufacturing method is low in cost and excellent in mass productivity. Furthermore, it is possible to print a fine pattern having high dimensional accuracy and smoothness by the development of printing technology. In order to perform printing, it is preferable that the ink does not dry and solidify on the printing plate or on the blanket. Control of ink fluidity on a printing press is also important, and ink viscosity can be adjusted with a dispersant or extender pigment.

  When the filter segment is formed by photolithography, the colored composition prepared as a solvent developing type or alkali developing type colored resist material is applied on a transparent substrate by spray coating, spin coating, slit coating, roll coating or the like. By a method, it applies so that a dry film thickness may be set to 0.2-5 micrometers. If necessary, the dried film is exposed to ultraviolet light through a mask having a predetermined pattern provided in contact with or non-contact with the film. Then, after immersing in a solvent or alkali developer or spraying the developer by spraying or the like to remove the uncured portion to form a desired pattern, the same operation is repeated for other colors to produce a color filter. be able to. Furthermore, in order to accelerate the polymerization of the colored resist material, heating can be performed as necessary. According to the photolithography method, a color filter with higher accuracy than the above printing method can be manufactured.

  In development, an aqueous solution such as sodium carbonate or sodium hydroxide is used as an alkali developer, and an organic alkali such as dimethylbenzylamine or triethanolamine can also be used. Moreover, an antifoamer and surfactant can also be added to a developing solution. In order to increase the UV exposure sensitivity, after coating and drying the colored resist, a water-soluble or alkaline water-soluble resin such as polyvinyl alcohol or a water-soluble acrylic resin is applied and dried to form a film that prevents polymerization inhibition by oxygen. Thereafter, ultraviolet exposure can also be performed.

  The color filter of the present invention can be produced by an electrodeposition method, a transfer method or the like in addition to the above method, but the colored composition or the photosensitive colored composition of the present invention can be used in any method. The electrodeposition method is a method for producing a color filter by using a transparent conductive film formed on a substrate and forming each color filter segment on the transparent conductive film by electrophoresis of colloidal particles. . The transfer method is a method in which a filter segment is formed in advance on the surface of a peelable transfer base sheet, and this filter segment is transferred to a desired substrate.

  A black matrix can be formed in advance before forming each color filter segment on a transparent substrate or a reflective substrate. As the black matrix, a chromium, chromium / chromium oxide multilayer film, an inorganic film such as titanium nitride, or a resin film in which a light-shielding agent is dispersed is used, but is not limited thereto. Further, a thin film transistor (TFT) may be formed in advance on the transparent substrate or the reflective substrate, and then each color filter segment may be formed. In addition, an overcoat film, a transparent conductive film, or the like is formed on the color filter of the present invention as necessary.

  Hereinafter, the present invention will be described based on examples, but the present invention is not limited thereto. In the examples, “parts” and “%” represent “parts by mass” and “mass%”, respectively. Me represents a methyl group, and Et represents an ethyl group.

(Elemental analysis and mass spectrometry)
Elemental analysis and mass spectrometry were used in determining and identifying the structure of the pigment dispersant. Elemental analysis was performed using Perkin Elmer 2400 CHN Element Analyzer. For mass spectrometry, MALDI-TOF MS Autoflex III TOF / TOF manufactured by Bruker Daltonics was used.

  The average primary particle diameter of the pigment and the pigment composition, the identification method, the weight average molecular weight (Mw) of the resin, and the acid value of the resin are as follows.

(Average primary particle diameter of pigment)
The average primary particle diameter of the pigment was measured by a method of directly measuring the size of primary particles from an electron micrograph using a transmission electron microscope (TEM). Specifically, the minor axis diameter and major axis diameter of the primary particles of each pigment were measured, and the average was taken as the particle diameter of the primary pigment particles. Next, for 100 or more pigment particles, the volume (weight) of each particle was obtained by approximating the obtained particle size cube, and the volume average particle size was defined as the average primary particle size.

(Weight average molecular weight of resin (Mw))
The weight average molecular weight (Mw) of the resin is TPCgel column (manufactured by Tosoh Corporation), GPC equipped with RI detector (manufactured by Tosoh Corporation, HLC-8120GPC), four separation columns connected in series, Is a polystyrene equivalent molecular weight measured using “TSK-GEL SUPER H5000”, “H4000”, “H3000”, and “H2000” manufactured by Tosoh Corporation in succession using tetrahydrofuran as the mobile phase.

(Resin acid value)
To 0.5 to 1.0 part of the resin solution, 80 ml of acetone and 10 ml of water are added and stirred to dissolve uniformly, and a 0.1 mol / L KOH aqueous solution is used as a titrant and an automatic titrator (“COM-555”). Titration using Hiranuma Sangyo Co., Ltd.) and the acid value of the resin solution was measured. Then, the acid value per solid content of the resin was calculated from the acid value of the resin solution and the solid content concentration of the resin solution.

<Method for producing binder resin solution>
(Preparation of acrylic resin solution 1)
A reaction vessel equipped with a separable four-necked flask equipped with a thermometer, a cooling tube, a nitrogen gas introduction tube, a dropping tube and a stirring device was charged with 196 parts of cyclohexanone, heated to 80 ° C., and purged with nitrogen in the reaction vessel. From the tube, 37.2 parts of n-butyl methacrylate, 12.9 parts of 2-hydroxyethyl methacrylate, 12.0 parts of methacrylic acid, paracumylphenol ethylene oxide modified acrylate (“Aronix M110” manufactured by Toagosei Co., Ltd.) 20.7 A mixture of 1.1 parts of 2,2′-azobisisobutyronitrile was added dropwise over 2 hours. After completion of the dropwise addition, the reaction was continued for another 3 hours to obtain an acrylic resin solution. After cooling to room temperature, about 2 parts of the resin solution was sampled, heated and dried at 180 ° C. for 20 minutes, and the nonvolatile content was measured. The methoxypropyl acetate was added to the previously synthesized resin solution so that the nonvolatile content was 20% by mass. Was added to prepare an acrylic resin solution 1. The weight average molecular weight (Mw) was 26000.

(Preparation of acrylic resin solution 2)
207 parts of cyclohexanone was charged into a reaction vessel equipped with a separable four-necked flask equipped with a thermometer, a cooling tube, a nitrogen gas introduction tube, a dropping tube and a stirring device, heated to 80 ° C., and the inside of the reaction vessel was purged with nitrogen. From the tube, 20 parts of methacrylic acid, 20 parts of paracumylphenol ethylene oxide modified acrylate (Aronix M110 manufactured by Toagosei Co., Ltd.), 45 parts of methyl methacrylate, 8.5 parts of 2-hydroxyethyl methacrylate, and 2,2′-azobis A mixture of 1.33 parts of isobutyronitrile was added dropwise over 2 hours. After completion of the dropwise addition, the reaction was further continued for 3 hours to obtain a copolymer resin solution. Next, after the nitrogen gas was stopped and stirred while injecting dry air for 1 hour with respect to the total amount of the copolymer solution obtained, the mixture was cooled to room temperature, and then 2-methacryloyloxyethyl isocyanate (Karenz manufactured by Showa Denko KK). MOI) A mixture of 6.5 parts, 0.08 part dibutyltin laurate and 26 parts cyclohexanone was added dropwise at 70 ° C. over 3 hours. After completion of the dropwise addition, the reaction was further continued for 1 hour to obtain an acrylic resin solution. After cooling to room temperature, sample 2 parts of the resin solution, heat dry at 180 ° C. for 20 minutes, measure the nonvolatile content, and add cyclohexanone to the previously synthesized resin solution so that the nonvolatile content is 20% by mass. Thus, an acrylic resin solution 2 was prepared. The weight average molecular weight (Mw) was 18000.

<Method for producing pigment dispersant>
[Example 1]
(Production of terminal amine of pigment dispersant 1 (RD-1))
97.5 parts of diethylaminopropylamine was added to 140 parts of water and dissolved by stirring at 20-25 ° C. 125 parts of 4-nitrobenzoyl chloride was added and stirred at 20 to 25 ° C. for 2 hours, and then stirred at 55 to 60 ° C. for 1 hour. Subsequently, this solution was mixed with 670 parts of water, 110 parts by weight of 80% acetic acid and 135 parts by weight of iron powder, and reacted at 85 ° C. to 90 ° C. for 5 hours. After cooling to 50 ° C. to 60 ° C. and filtering off iron powder, soda ash was added to the filtrate to precipitate the target product. This slurry was filtered and dried to obtain 138 parts of 4-amino-N- (3- (diethylamino) propyl) benzamide represented by the following formula (7-a).

Formula (7-a)

(Production of Base Compound of Pigment Dispersant 1 (RD-1))
23.7 parts of 4-methoxy-3-nitrobenzoic acid and 0.7 parts of N, N-dimethylformamide (DMF) were dissolved in 180 parts of toluene. To this was added dropwise 17.9 parts of thionyl chloride over 25 minutes, and the mixture was refluxed at 110 ° C. for 1 hour to synthesize benzoic acid chloride. In 140 parts of toluene, 30.0 parts of 4-amino-N- (3- (diethylamino) propyl) benzamide represented by the formula (7-a) was dispersed, and benzoic acid chloride was added dropwise thereto at room temperature for 1 hour. Subsequently, refluxing was performed for 4 hours to complete the reaction. Toluene was distilled off while neutralizing with a 10% aqueous sodium carbonate solution, followed by reslurry with a 3% aqueous NaOH solution, filtration and drying to obtain 40.0 parts of a compound represented by the following formula (7-b).

Formula (7-b)

  40.0 parts of the compound represented by the above formula (7-b) and 80 parts of 65% NaSH are added to 300 parts of water and refluxed for 6 hours, and 35.0 parts of the base compound represented by the following formula (7-c) is added. Obtained.

Formula (7-c)

(Synthesis of Pigment Dispersant 1 (RD-1))
20.0 parts of the base compound represented by the above formula (7-c) is dispersed in 200 parts of water, ice is added to adjust the temperature to 5 ° C., 20.0 parts of 35% aqueous hydrochloric acid is added, and the mixture is stirred for 1 hour. An aqueous solution prepared by adding 3.60 parts of sodium nitrite to 11.0 parts of water was added and stirred for 2 hours. Subsequently, an aqueous solution consisting of 59.0 parts of an 80% aqueous acetic acid solution, 65.0 parts of a 25% aqueous sodium hydroxide solution, and 64.0 parts of water was added to form a diazonium salt aqueous solution. On the other hand, 16.6 parts of N- [2-methoxy-5-chlorophenyl] -3-hydroxy-2-naphthalenecarboxamide and 53.5 parts of 25% aqueous sodium hydroxide solution were dissolved in 340 parts of methanol to obtain a coupler solution. .
This coupler solution was poured into the diazonium salt aqueous solution at 5 ° C. over 30 minutes to carry out a coupling reaction. The pH at this time was 4.4. After stirring for 1 hour and confirming the disappearance of the diazonium salt, the mixture was heated to 70 ° C., filtered, washed with water, and dried at 90 ° C. for 24 hours to obtain 34.0 parts of a pigment dispersant represented by the formula (7). . The obtained pigment dispersant was subjected to elemental analysis. As a result, the calculated value (C) 65.17%, (H) 5.61%, and (N) 11.40% were measured (C) 65. .1%, (H) 5.5%, (N) 11.3%, and the result of mass spectrometry by TOF-MS identified the compound of interest.

Formula (7)

[Example 2]
(Production of Pigment Dispersant 2 (RD-2))
23.7 parts of 4-methoxy-3-nitrobenzoic acid and 0.7 parts of N, N-dimethylformamide (DMF) were dissolved in 180 parts of toluene. To this was added dropwise 17.9 parts of thionyl chloride over 25 minutes, and the mixture was refluxed at 110 ° C. for 1 hour to synthesize benzoic acid chloride. 15.7 parts of diethylaminopropylamine were dissolved in 140 parts of toluene, and benzoic acid chloride was added dropwise thereto at room temperature for 1 hour. Subsequently, refluxing was performed for 4 hours to complete the reaction. Toluene was distilled off while neutralizing with 10% aqueous sodium carbonate solution, reslurried with 3% aqueous NaOH solution, and extracted with diethyl ether. Subsequently, the solvent was removed from the extract with an evaporator, and the residue was dried at 80 ° C. to obtain 31.2 parts of a compound represented by the following formula (9-a).

Formula (9-a)

  31.2 parts of the compound represented by the above formula (9-a) and 62 parts of 65% NaSH are added to 230 parts of water and refluxed for 6 hours, and 27.0 parts of the base compound represented by the following formula (9-b) is added. Obtained.

Formula (9-b)

  Next, the same operation as in Example 1 was carried out except that 20 parts of the base compound represented by the formula (7-c) was changed to 14.0 parts of the base compound represented by the formula (9-b). 27.2 parts of a pigment dispersant represented by 9) were obtained. The obtained pigment dispersant was subjected to elemental analysis. The calculated value (C) of 64.12%, (H) of 5.87%, and (N) of 11.33% was actually measured (C) 64. .2%, (H) 6.0%, (N) 11.4%, and the result of mass spectrometry by TOF-MS identified the compound of interest.

Formula (9)

[Example 3]
(Production of Compound of Pigment Dispersant 3 (RD-3))
3-nitrobenzoyl chloride (23.8 parts) was dissolved in 190 parts of toluene, and this was added dropwise to a solution prepared by dissolving 21.0 parts of diethylaminopropylamine in 150 parts of toluene at room temperature for 1 hour. Subsequently, refluxing was performed for 4 hours to complete the reaction. Toluene was distilled off while neutralizing with a 10% aqueous sodium carbonate solution, followed by reslurry and extraction with 3% aqueous NaOH solution. Subsequently, the solvent was removed by an evaporator, and after drying at 80 ° C., 28.6 parts of a compound represented by the following formula (10-a) was obtained.

Formula (10-a)

  When 28.6 parts of the compound represented by the above formula (10-a) and 57 parts of 65% NaSH are placed in 215 parts of water and refluxed for 6 hours, 22.8 parts of a base compound represented by the following formula (10-b) is obtained. It was.

Formula (10-b)

  In Example 1, the same operation as in Example 1 was carried out except that 20 parts of the base compound represented by formula (7-c) was changed to 12.5 parts of the base compound represented by formula (10-b). 26.7 parts of a pigment dispersant represented by the formula (10) were obtained. The obtained pigment dispersant was subjected to elemental analysis. As a result, it was found that the calculated value (C) 65 was 65.35%, (H) 5.83%, and (N) 11.91%. 4%, (H) 5.7%, (N) 12.0%, and the result of mass spectrometry by TOF-MS identified the compound of interest.

Formula (10)

[Example 4]
(Production of Pigment Dispersant 4 (RD-4))
12.5 parts of the compound represented by the formula (7-a) was dispersed in 190 parts of water, ice was added to adjust the temperature to 5 ° C., and 19.8 parts of 35% aqueous hydrochloric acid solution was added and stirred for 1 hour. To this solution, an aqueous solution prepared by adding 3.60 parts of sodium nitrite to 11.0 parts of water was added and stirred for 2 hours. Subsequently, an aqueous solution consisting of 59.0 parts of an 80% aqueous acetic acid solution, 65.0 parts of a 25% aqueous sodium hydroxide solution, and 64.0 parts of water was added to form a diazonium salt aqueous solution.
Separately, 16.6 parts of N- [2-methoxy-5-chlorophenyl] -3-hydroxy-2-naphthalenecarboxamide and 53.5 parts of 25% aqueous sodium hydroxide solution were dissolved in 340 parts of methanol to obtain a coupler solution. .
This coupler solution was poured into the diazonium salt aqueous solution at 5 ° C. over 30 minutes to carry out a coupling reaction. The pH at this time was 4.4. After stirring for 1 hour and confirming the disappearance of the diazonium salt, the mixture was heated to 70 ° C., filtered, washed with water, and dried at 90 ° C. for 24 hours to obtain 25.8 parts of a pigment dispersant represented by the formula (11). It was. The obtained pigment dispersant was subjected to elemental analysis. As a result, it was found that the calculated value (C) 65 was 65.35%, (H) 5.83%, and (N) 11.91%. .3%, (H) 5.9%, (N) 11.8%, and the result of mass spectrometry by TOF-MS identified the compound of interest.

Formula (11)

[Example 5]
(Production of Pigment Dispersant 5 (RD-5))
2.51 parts of 80% acetic acid was added to 18.0 parts of water and cooled to 5-10 ° C. 4.24 parts of cyanuric chloride and 3.18 parts of 3-aminoacetanilide were added and stirred at 10 to 20 ° C. for 1 hour. Next, 37.3 parts of a 2.5% NaOH aqueous solution was added dropwise, and the mixture was further stirred at 10 to 20 ° C. for 1 hour. Subsequently, 6.89 parts of diethylaminopropylamine was added and stirred at room temperature for 1 hour. The mixture was cooled to 5 to 10 ° C., 37.3 parts of 2.5% NaOH aqueous solution was added dropwise, and the mixture was further stirred at 75 ° C. for 2 hours. After allowing to cool, 11.0 parts of 35% HCl aqueous solution was added and stirred at 100 ° C. for 3 hours and allowed to cool.
Ice was added to the above solution to adjust the temperature to 5 ° C., and an aqueous solution prepared by adding 1.53 parts of sodium nitrite to 5.1 parts of water was added and stirred for 2 hours. Subsequently, an aqueous solution consisting of 15.6 parts of an 80% aqueous acetic acid solution, 17.1 parts of a 25% aqueous sodium hydroxide solution and 18.4 parts of water was added to form a diazonium salt aqueous solution.
Separately, 7.01 parts of N- [2-methoxy-5-chlorophenyl] -3-hydroxy-2-naphthalenecarboxamide and 14.1 parts of 25% aqueous sodium hydroxide solution were dissolved in 154 parts of methanol to obtain a coupler solution. .
This coupler solution was poured into the diazonium salt aqueous solution at 5 ° C. over 30 minutes to carry out a coupling reaction. The pH at this time was 4.4. After stirring for 1 hour and confirming the disappearance of the diazonium salt, it was heated to 70 ° C., filtered, washed with water, and dried at 90 ° C. for 24 hours to obtain 13.8 parts of a pigment dispersant represented by the formula (12). It was. The obtained pigment dispersant was subjected to elemental analysis. The calculated value (C) 61.60%, (H) 6.25%, and (N) 18.38% were measured (C) 61. It was 0.5%, (H) 6.4%, (N) 18.5%, and was identified as the target compound from the results of mass spectrometry by TOF-MS.

Formula (12)

[Example 6]
(Production of Pigment Dispersant 6 (RD-6))
2.51 parts of 80% acetic acid was added to 18.0 parts of water and cooled to 5-10 ° C. 4.24 parts of cyanuric chloride and 3.18 parts of 4-aminoacetanilide were added and stirred at 10 to 20 ° C. for 1 hour. Next, 37.3 parts of a 2.5% NaOH aqueous solution was added dropwise, and the mixture was further stirred at 10 to 20 ° C. for 1 hour. Subsequently, 6.89 parts of diethylaminopropylamine was added and stirred at room temperature for 1 hour. The mixture was cooled to 5 to 10 ° C., 37.3 parts of 2.5% NaOH aqueous solution was added dropwise, and the mixture was further stirred at 75 ° C. for 2 hours. After allowing to cool, 11.0 parts of 35% HCl aqueous solution was added and stirred at 100 ° C. for 3 hours and allowed to cool.
Ice was added to the above solution to adjust the temperature to 5 ° C., and an aqueous solution prepared by adding 1.53 parts of sodium nitrite to 5.1 parts of water was added and stirred for 2 hours. Subsequently, an aqueous solution consisting of 15.6 parts of an 80% aqueous acetic acid solution, 17.1 parts of a 25% aqueous sodium hydroxide solution and 18.4 parts of water was added to form a diazonium salt aqueous solution.
Separately, 7.01 parts of N- [2-methoxy-5-chlorophenyl] -3-hydroxy-2-naphthalenecarboxamide and 14.1 parts of 25% aqueous sodium hydroxide solution were dissolved in 154 parts of methanol to obtain a coupler solution. .
This coupler solution was poured into the diazonium salt aqueous solution at 5 ° C. over 30 minutes to carry out a coupling reaction. The pH at this time was 4.4. After stirring for 1 hour and confirming the disappearance of the diazonium salt, it was heated to 70 ° C., filtered, washed with water, and dried at 90 ° C. for 24 hours to obtain 14.2 parts of a pigment dispersant represented by the formula (13). It was. The obtained pigment dispersant was subjected to elemental analysis. The calculated value (C) 61.60%, (H) 6.25%, and (N) 18.38% were measured (C) 61. 7%, (H) 6.2%, (N) 18.3%, and the results of mass spectrometry by TOF-MS identified the compound of interest.

Formula (13)

[Example 7]
(Production of Base Compound for Pigment Dispersant 7 (RD-7))
16 parts of 5-nitroisophthalic acid and 1.0 part of N, N-dimethylformamide (DMF) were dissolved in 110 parts of toluene. 22.6 parts of thionyl chloride was dripped here over 25 minutes, and it was made to recirculate | reflux at 110 degreeC for 1 hour, and benzoic acid chloride was synthesize | combined. 4-Amino-N- (3- (diethylamino) propyl) benzamide (38.0 parts) represented by the formula (7-a) is dispersed in 90 parts of toluene, and the above benzoic acid chloride is added dropwise thereto over 1 hour at room temperature. Then, reflux was performed for 4 hours to complete the reaction. Toluene was distilled off while neutralizing with a 10% aqueous sodium carbonate solution, followed by reslurry, filtration and drying with a 3% aqueous NaOH solution to obtain 28.0 parts of a compound represented by the following formula (18-a).

Formula (18-a)

  Next, 25.0 parts of the compound represented by the above formula (18-a) was dissolved in 100 parts of N-methylpyrrolidone, and 32 parts of sodium hydrosulfide hydrate (containing 65% sodium hydrosulfide) was added to 55 parts thereof. After adding an aqueous solution dissolved in a part of water, the mixture was refluxed for 6 hours to obtain 20.0 parts of a base compound represented by the following formula (18-b).

Formula (18-b)

(Synthesis of Pigment Dispersant 7 (RD-7))
The same operation as in Example 1 was carried out except that 20 parts of the base compound represented by the formula (7-c) was changed to 32.0 parts of the base compound represented by the formula (18-b). 45.4 parts of a pigment dispersant represented by the formula: The obtained pigment dispersant was subjected to elemental analysis. As a result, the calculated value (C) 66.01%, (H) 6.15%, and (N) 12.83 were compared with the measured value (C) 66.61. 1%, (H) 6.1%, (N) 12.7%, and the result of mass spectrometry by TOF-MS identified the target compound.

Formula (18)

[Example 8]
(Production of Base Compound of Pigment Dispersant 8 (RD-8))
16 parts of 5-nitroisophthalic acid and 2.0 parts of N, N-dimethylformamide (DMF) were dissolved in 110 parts of toluene. To this, 22.6 parts of thionyl chloride was added dropwise over 25 minutes and refluxed at 110 ° C. for 1 hour to synthesize benzoic acid chloride. Diethylaminopropylamine (20.0 parts) was dissolved in 90 parts of toluene, and the above benzoic acid chloride was added dropwise thereto at room temperature over 1 hour, followed by refluxing for 4 hours to complete the reaction. Toluene was distilled off while neutralizing with a 10% aqueous sodium carbonate solution, and then 26.4 parts of a compound represented by the following formula (19-a) were obtained through reslurry, filtration and drying with a 3% aqueous NaOH solution.

Formula (19-a)

  16.2 parts of the compound represented by the above formula (19-a) was dissolved in 100 parts of N-methylpyrrolidone, and 32 parts of sodium hydrosulfide hydrate (containing 65% sodium hydrosulfide) was dissolved in 55 parts. An aqueous solution in water was added. After refluxing for 6 hours, 13.1 parts of a base compound represented by the following formula (19-b) was obtained.

Formula (19-b)

  Subsequently, 14.9 parts of 4-methoxy-3-nitrobenzoic acid and 1.0 part of N, N-dimethylformamide (DMF) were dissolved in 110 parts of toluene. To this was added dropwise 11.1 parts of thionyl chloride over 25 minutes and refluxed at 110 ° C. for 1 hour to synthesize benzoic acid chloride. In 90 parts of toluene, 31.0 parts of the compound of the formula (19-b) was dissolved, and the benzoic acid chloride was added dropwise thereto at room temperature for 1 hour, followed by refluxing for 4 hours to complete the reaction. Toluene was distilled off while neutralizing with a 10% aqueous sodium carbonate solution, and then 35.4 parts of a compound represented by the following formula (19-c) was obtained through reslurry, filtration and drying with a 3% aqueous NaOH solution.

Formula (19-c)

  16.2 parts of the compound represented by the above formula (19-c) was dissolved in 100 parts of N-methylpyrrolidone, and 32 parts of sodium hydrosulfide hydrate (containing 65% sodium hydrosulfide) was added to 55 parts. After adding an aqueous solution dissolved in water, the mixture was refluxed for 6 hours to obtain 16.5 parts of a base compound represented by the following formula (19-d).

Formula (19-d)

(Synthesis of Pigment Dispersant 8 (RD-8))
The same operation as in Example 1 was carried out, except that 20 parts of the base compound represented by formula (7-c) was changed to 27.8 parts of the base compound represented by formula (19-d). 44.9 parts of a pigment dispersant represented by the formula: The obtained pigment dispersant was subjected to elemental analysis. The calculated value (C) of 64.53%, (H) of 6.43%, and (N) of 12.54 was compared with the actually measured value (C) of 64.3%. It was 6%, (H) 6.3%, (N) 12.4%, and the result of mass spectrometry by TOF-MS identified the target compound.

Formula (19)

[Example 9]
(Production of Pigment Dispersant 9 (RD-9))
The same operation as in Example 2 was carried out except that 15.7 parts of diethylaminopropylamine was replaced with 12.3 parts of dimethylaminopropylamine to obtain 26.3 parts of a pigment dispersant represented by the formula (20). It was. The obtained pigment dispersant was subjected to elemental analysis. As a result, the calculated value (C) 63.10%, (H) 5.47%, and (N) 11.87% were measured (C) 63. 0.02%, (H) 5.3%, (N) 12.0%, and the result of mass spectrometry by TOF-MS identified the target compound.

Formula (20)

[Example 10]
(Production of Pigment Dispersant 10 (RD-10))
The same operation as in Example 2 was carried out except that 15.7 parts of diethylaminopropylamine was replaced with 22.4 parts of dibutylaminopropylamine to obtain 28.4 parts of a pigment dispersant represented by the formula (21). It was. The obtained pigment dispersant was subjected to elemental analysis. The calculated value (C) 66.91%, (H) 6.58%, and (N) 10.39% were measured (C) 66. 0.0%, (H) 6.7%, (N) 10.3%, and the result of mass spectrometry by TOF-MS identified the compound of interest.

Formula (21)

[Example 11]
(Production of Pigment Dispersant 11 (RD-11))
The same operation as in Example 2 was conducted, except that 15.7 parts of diethylaminopropylamine was replaced with 17.3 parts of diethylaminobutylamine, to obtain 27.6 parts of a pigment dispersant represented by the formula (22). The obtained pigment dispersant was subjected to elemental analysis. As a result, it was found that the calculated value (C) 64.60%, (H) 6.06%, and (N) 11.08% were measured (C) 64. It was identified as the target compound from the results of mass spectrometry by TOF-MS, that was 0.5%, (H) 6.2%, (N) 11.2%.

Formula (22)

[Example 12]
(Production of Pigment Dispersant 12 (RD-12))
The same operation as in Example 2 was conducted, except that 15.7 parts of diethylaminopropylamine was replaced with 13.9 parts of diethylaminoethylamine, to obtain 26.9 parts of a pigment dispersant represented by the formula (23). The obtained pigment dispersant was subjected to elemental analysis. The calculated value (C) 63 was 63.62%, (H) 5.67%, and (N) 11.59%. It was identified as the target compound from the results of mass spectrometry by TOF-MS, that was 0.5%, (H) 5.5%, (N) 11.7%.

Formula (23)

[Example 13]
(Production of Pigment Dispersant 13 (RD-13))
The same operation as in Example 1 was carried out except that 23.7 parts of 4-methoxy-3-nitrobenzoic acid was replaced with 21.7 parts of 4-methyl-3-nitrobenzoic acid, and represented by the formula (24). 32.2 parts of pigment dispersant to be obtained were obtained. The obtained pigment dispersant was subjected to elemental analysis. The calculated value (C) 66 was 66.61%, (H) 5.73%, and (N) 11.65%. 7%, (H) 5.6%, (N) 11.7%, and the result of mass spectrometry by TOF-MS identified the compound of interest.

Formula (24)

[Example 14]
(Production of Pigment Dispersant 14 (RD-14))
The same operation as in Example 2 was carried out except that 23.7 parts of 4-methoxy-3-nitrobenzoic acid was replaced with 21.7 parts of 4-methyl-3-nitrobenzoic acid, and represented by the formula (25). 26.6 parts of pigment dispersant to be obtained were obtained. The obtained pigment dispersant was subjected to elemental analysis. The calculated value (C) 65 was found to be 65.83%, (H) 6.03%, and (N) 11.63%. , 9%, (H) 6.1%, (N) 11.5%, and the result of mass spectrometry by TOF-MS identified the compound of interest.

Formula (25)

[Example 15]
(Production of Pigment Dispersant 15 (RD-15))
23.7 parts of 4-methoxy-3-nitrobenzoic acid are added to 21.7 parts of 4-methyl-3-nitrobenzoic acid and N- [2-methoxy-5-chlorophenyl] -3-hydroxy-2-naphthalenecarbohydrate. The same operation as in Example 1 was carried out except that 16.6 parts of amide was replaced with 14.9 parts of N- [2-methoxyphenyl] -3-hydroxy-2-naphthalenecarboxamide. 25.3 parts of the pigment dispersant represented were obtained. The obtained pigment dispersant was subjected to elemental analysis. The calculated value (C) of 69.95%, (H) of 6.16%, and (N) of 12.24% was actually measured (C) 70. 0.0%, (H) 6.0%, (N) 12.1%, and mass spectrometry by TOF-MS identified the target compound.

Formula (26)

[Example 16]
(Production of Pigment Dispersant 16 (RD-16))
23.7 parts of 4-methoxy-3-nitrobenzoic acid are added to 21.7 parts of 4-methyl-3-nitrobenzoic acid and N- [2-methoxy-5-chlorophenyl] -3-hydroxy-2-naphthalenecarbohydrate. The same procedure as in Example 1 was carried out, except that 16.6 parts of amide were replaced with 15.8 parts of N- [2-methyl-5-chlorophenyl] -3-hydroxy-2-naphthalenecarboxamide. 26.2 parts of pigment dispersant represented by 27) were obtained. The obtained pigment dispersant was subjected to elemental analysis. The measured value (C) 68 was found to be 68.12% for the calculated value (C), 5.86% for (H), and 11.92% for (N). .2%, (H) 6.0%, (N) 11.8%, and the result of mass spectrometry by TOF-MS identified the compound of interest.

Formula (27)

[Example 17]
(Production of Pigment Dispersant 17 (RD-17))
23.7 parts of 4-methoxy-3-nitrobenzoic acid are added to 21.7 parts of 4-methyl-3-nitrobenzoic acid and N- [2-methoxy-5-chlorophenyl] -3-hydroxy-2-naphthalenecarbohydrate. The same procedure as in Example 1 was performed, except that 16.6 parts of amide were replaced with 14.1 parts of N- [2-methylphenyl] -3-hydroxy-2-naphthalenecarboxamide, and the compound of formula (28) 24.6 parts of the pigment dispersant represented were obtained. The obtained pigment dispersant was subjected to elemental analysis. The calculated value (C) 71.62%, (H) 6.31%, (N) 12.53% were measured (C) 71. From 6%, (H) 6.4%, (N) 12.4%, and the result of mass spectrometry by TOF-MS, it was identified as the target compound.

Formula (28)

[Example 18]
(Production of Pigment Dispersant 18 (RD-18))
23.7 parts of 4-methoxy-3-nitrobenzoic acid are added to 21.7 parts of 4-methyl-3-nitrobenzoic acid and N- [2-methoxy-5-chlorophenyl] -3-hydroxy-2-naphthalenecarbohydrate. The same procedure as in Example 1 was carried out, except that 16.6 parts of amide were replaced with 15.1 parts of N- [3-chlorophenyl] -3-hydroxy-2-naphthalenecarboxamide. 25.5 parts of pigment dispersant to be obtained were obtained. The obtained pigment dispersant was subjected to elemental analysis. The calculated value (C) 67.77%, (H) 5.69%, and (N) 12.16% were measured (C) 67. 7%, (H) 5.8%, (N) 12.3%, and the results of mass spectrometry by TOF-MS identified the compound of interest.

Formula (29)

[Example 19]
(Production of Pigment Dispersant 19 (RD-19))
23.7 parts of 4-methoxy-3-nitrobenzoic acid are added to 21.7 parts of 4-methyl-3-nitrobenzoic acid and N- [2-methoxy-5-chlorophenyl] -3-hydroxy-2-naphthalenecarbohydrate. A pigment dispersion represented by the formula (30) was carried out in the same manner as in Example 1, except that 16.6 parts of the amide was replaced with 13.3 parts of N-phenyl-3-hydroxy-2-naphthalenecarboxamide. 24.0 parts of agent were obtained. The obtained pigment dispersant was subjected to elemental analysis. As a result, the calculated value (C) 71.32%, (H) 6.14%, and (N) 12.80% were measured (C) 71. .4%, (H) 6.0%, (N) 12.7%, and the result of mass spectrometry by TOF-MS identified the target compound.

Formula (30)

[Example 20]
(Production of Pigment Dispersant 20 (RD-20))
23.7 parts of 4-methoxy-3-nitrobenzoic acid and 24.2 parts of 4-chloro-3-nitrobenzoic acid are added to N- [2-methoxy-5-chlorophenyl] -3-hydroxy-2-naphthalenecarbo. The same procedure as in Example 1 was performed, except that 16.6 parts of amide was replaced with 16.6 parts of N- [2-methyl-5-chlorophenyl] -3-hydroxy-2-naphthalenecarboxamide. 27.7 parts of a pigment dispersant represented by 31) were obtained. The obtained pigment dispersant was subjected to elemental analysis. The calculated value (C) of 64.55%, (H) of 5.28%, and (N) of 11.58% was actually measured (C) 64. It was identified as the target compound from the results of mass spectrometry by TOF-MS, that was 0.5%, (H) 5.4%, (N) 11.5%.

Formula (31)

[Example 21]
(Production of Pigment Dispersant 21 (RD-21))
23.7 parts of 4-methoxy-3-nitrobenzoic acid, 21.7 parts of 4-methyl-3-nitrobenzoic acid, and N- [2-methoxy-5-chlorophenyl] -3-hydroxy-2-naphthalenecarbo The same operation as in Example 2 was carried out except that 16.6 parts of amide was replaced with 18.5 parts of N- [2-chloro-5-trifluoromethylphenyl] -3-hydroxy-2-naphthalenecarboxamide. 28.6 parts of pigment dispersant represented by the formula (32) were obtained. The obtained pigment dispersant was subjected to elemental analysis. The calculated value (C) was 61.92%, (H) was 5.20%, and (N) was 10.94%. 0.0%, (H) 5.4%, (N) 11.0%, and the result of mass spectrometry by TOF-MS identified the target compound.

Formula (32)

[Example 22]
(Production of Pigment Dispersant 22 (RD-22))
23.7 parts of 4-methoxy-3-nitrobenzoic acid, 21.7 parts of 4-methyl-3-nitrobenzoic acid, and N- [2-methoxy-5-chlorophenyl] -3-hydroxy-2-naphthalenecarbo The same operation as in Example 1 was carried out except that 16.6 parts of amide was replaced with 18.5 parts of N- [2-chloro-5-trifluoromethylphenyl] -3-hydroxy-2-naphthalenecarboxamide. 34.0 parts of pigment dispersant represented by the formula (33) were obtained. The obtained pigment dispersant was subjected to elemental analysis. As a result, the measured value (C) 63 was compared with the calculated value (C) 63.28%, (H) 5.04%, and (N) 11.07%. .1%, (H) 5.0%, (N) 11.2%, and the result of mass spectrometry by TOF-MS identified the compound of interest.

Formula (33)

[Example 23]
(Production of Pigment Dispersant 23 (RD-23))
23.7 parts of 4-methoxy-3-nitrobenzoic acid and 24.2 parts of 4-chloro-3-nitrobenzoic acid are added to N- [2-methoxy-5-chlorophenyl] -3-hydroxy-2-naphthalenecarbo. The same operation as in Example 1 was carried out except that 16.6 parts of amide was replaced with 18.5 parts of N- [2-chloro-5-trifluoromethylphenyl] -3-hydroxy-2-naphthalenecarboxamide. 34.9 parts of pigment dispersant represented by the formula (34) were obtained. The obtained pigment dispersant was subjected to elemental analysis. As a result, the calculated value (C) 60.08%, (H) 4.52%, and (N) 10.78% were measured (C) 60. .1%, (H) 4.5%, (N) 10.6%, and the result of mass spectrometry by TOF-MS identified the target compound.

Formula (34)

[Example 24]
(Production of Pigment Dispersant 24 (RD-24))
16.6 parts of N- [2-methoxy-5-chlorophenyl] -3-hydroxy-2-naphthalenecarboxamide are added to N- [4- (2-oxo-2,3-dihydro-1H-benzimidazole-5 Yl)]-3-hydroxy-2-naphthalenecarboxamide, except that 16.2 parts were used, the same operation as in Example 1 was carried out to obtain 32.2 parts of a pigment dispersant represented by the formula (35). It was. The obtained pigment dispersant was subjected to elemental analysis. The calculated value (C) 66.92%, (H) 5.53%, and (N) 15.38% were measured (C) 66. 0.05%, (H) 5.4%, (N) 15.5%, and the result of mass spectrometry by TOF-MS identified the target compound.

Formula (35)

[Example 25]
(Synthesis of Pigment Dispersant 25 (RD-25))
16.6 parts of N- [2-methoxy-5-chlorophenyl] -3-hydroxy-2-naphthalenecarboxamide are added to N- [4- (2-oxo-2,3-dihydro-1H-benzimidazole-5 Yl)]-3-hydroxy-2-naphthalenecarboxamide Except for changing to 16.2 parts, the same operation as in Example 4 was performed to obtain 25.0 parts of a pigment dispersant represented by the formula (36). It was. The obtained pigment dispersant was subjected to elemental analysis. The calculated value (C) 66.31%, (H) 5.74%, and (N) 16.91% were measured (C) 66. .2%, (H) 5.6%, (N) 16.8%, and the result of mass spectrometry by TOF-MS identified the compound of interest.

Formula (36)

[Example 26]
(Production of Pigment Dispersant 26 (RD-26))
23.7 parts of 4-methoxy-3-nitrobenzoic acid, 21.7 parts of 4-methyl-3-nitrobenzoic acid, and N- [2-methoxy-5-chlorophenyl] -3-hydroxy-2-naphthalenecarbo 16.6 parts of the amide were replaced with 16.2 parts of N- [4- (2-oxo-2,3-dihydro-1H-benzimidazol-5-yl)]-3-hydroxy-2-naphthalenecarboxamide. Except for the above, the same operation as in Example 1 was performed to obtain 31.9 parts of a pigment dispersant represented by the formula (37). The obtained pigment dispersant was subjected to elemental analysis. As a result, the calculated value (C) 67.40%, (H) 5.66%, and (N) 15.72% were measured (C) 67. .3%, (H) 5.8%, (N) 15.8%, and the result of mass spectrometry by TOF-MS identified the compound of interest.

Formula (37)

[Example 27]
(Production of Pigment Dispersant 27 (RD-27))
16.6 parts of N- [2-methoxy-5-chlorophenyl] -3-hydroxy-2-naphthalenecarboxamide are added to N- [4- (2-oxo-2,3-dihydro-1H-benzimidazole-5 Yl)]-3-hydroxy-2-naphthalenecarboxamide, except that 16.2 parts were used, the same operation as in Example 2 was carried out to obtain 31.9 parts of a pigment dispersant represented by the formula (38). It was. The obtained pigment dispersant was subjected to elemental analysis. The calculated value (C) of 64.01%, (H) of 5.79%, and (N) of 16.08% was actually measured (C) 64. , 9%, (H) 5.9%, (N) 16.2%, and the results of mass spectrometry by TOF-MS identified the target compound.

Formula (38)

<Production of pigment composition>
[Example 28]
(Preparation of Pigment Composition 1 (RP-1))
C. I. 90 parts of Pigment Red 269 (PR269) (Permanent Carmine 3810 manufactured by Sanyo Dye), 10 parts of Pigment Dispersant 1 (RD-1), 1200 parts of sodium chloride, and 120 parts of diethylene glycol, 1 gallon kneader made of stainless steel (Inoue Manufacturing Co., Ltd.) And kneaded at 60 ° C. for 6 hours and subjected to salt milling. The obtained kneaded product is poured into 3 liters of warm water, stirred for 1 hour while being heated to 70 ° C., made into a slurry, repeatedly filtered and washed with water to remove sodium chloride and diethylene glycol, and then dried at 80 ° C. overnight. 98 parts of pigment composition 1 (RP-1) were obtained. The average primary particle size was 29 nm.

[Examples 29 to 45, 47 to 68, 73 to 75]
(Preparation of pigment compositions 2-18, 20-41, 46-48 (RP-2-18, 20-41, 46-48))
The azo pigment represented by the general formula (3), the pigment dispersant represented by the general formula (1) or the formula (2), the pigment dispersant represented by the general formula (4), and the general formula (5) Pigment compositions 2 to 18, 20 to 41, and 46 to 48 were prepared in the same manner as pigment composition 1 (RP-1) except that the azo pigments were changed as shown in Table 1.
The pigments used are shown below.
・ C. I. Pigment Red 147 (PR147) (“Permanent Pink F3B 01” manufactured by Clariant)
・ C. I. Pigment Red 245 (PR245) (“FAST RED 30T” manufactured by Tokyo Color Material Industries Co., Ltd.)
・ C. I. Pigment Red 176 (PR176) (“Novoperm Carmine HF3C” manufactured by Clariant)

[Example 46]
(Preparation of Pigment Composition 19 (RP-19))
125 parts of 3-amino-4-methoxybenzanilide are dispersed in 2000 parts of water, ice is added to adjust the temperature to 5 ° C., 205 parts of 35% aqueous hydrochloric acid is added, and the mixture is stirred for 1 hour. A water solution prepared by adding 110 parts to water was added, and the mixture was stirred for 2 hours. An aqueous solution consisting of 380 parts of an 80% aqueous acetic acid solution, 418 parts of a 25% aqueous sodium hydroxide solution, and 413 parts of water was added to form an aqueous diazonium salt solution. On the other hand, 154.4 parts of N- [2-methoxyphenyl] -3-hydroxy-2-naphthalenecarboxamide and 1344 parts of 25% aqueous sodium hydroxide solution were dissolved in 3500 parts of methanol to obtain a coupler solution.
This coupler solution was poured into the 5 ° C. diazonium salt aqueous solution over 30 minutes to carry out a coupling reaction. The pH at this time was 4.4. After stirring for 3 hours and confirming the disappearance of the diazonium salt, the mixture was heated to 70 ° C., filtered, washed with water, and dried at 90 ° C. for 24 hours. I. 276 parts of Pigment Red 261 (PR261) was obtained.
The obtained C.I. I. 90 parts of Pigment Red 261 (PR261), 10 parts of Pigment Dispersant 4 (RD-4), 1200 parts of sodium chloride, and 120 parts of diethylene glycol were charged into a stainless 1 gallon kneader (manufactured by Inoue Seisakusho) at 60 ° C. The mixture was kneaded for 6 hours and subjected to salt milling. The obtained kneaded product is poured into 3 liters of warm water, stirred for 1 hour while being heated to 70 ° C., made into a slurry, repeatedly filtered and washed with water to remove sodium chloride and diethylene glycol, and then dried at 80 ° C. overnight. 98 parts of pigment composition 19 (RP-19) were obtained. The average primary particle size was 29 nm.

[Example 69]
(Preparation of pigment composition 42 (RP-42))
112.5 parts of 3-amino-4-methoxybenzanilide and 14.4 parts of the base compound represented by the formula (9-b) are dispersed in 2000 parts of water, adjusted to a temperature of 5 ° C. by adding ice, 35% After adding 205 parts of an aqueous hydrochloric acid solution and stirring for 1 hour, an aqueous solution prepared by adding 37.5 parts of sodium nitrite to 110 parts of water was added and stirred for 2 hours. An aqueous solution consisting of 380 parts of an 80% aqueous acetic acid solution, 418 parts of a 25% aqueous sodium hydroxide solution, and 413 parts of water was added to form an aqueous diazonium salt solution. On the other hand, 172.5 parts of N- [2-methoxy-5-chlorophenyl] -3-hydroxy-2-naphthalenecarboxamide and 1344 parts of 25% aqueous sodium hydroxide solution were dissolved in 3500 parts of methanol to obtain a coupler solution.
This coupler solution was poured into the 5 ° C. diazonium salt aqueous solution over 30 minutes to carry out a coupling reaction. The pH at this time was 4.4. After stirring for 3 hours and confirming the disappearance of the diazonium salt, the mixture was heated to 70 ° C., filtered, washed with water, and dried at 90 ° C. for 24 hours. I. 265.7 parts of a mixture of Pigment Red 269 (PR269) and Pigment Dispersant 2 (RD-2) represented by Formula (9) were obtained.
100 parts of the obtained mixture, 1200 parts of sodium chloride, and 120 parts of diethylene glycol were charged into a stainless steel 1 gallon kneader (manufactured by Inoue Seisakusho), kneaded at 60 ° C. for 6 hours, and subjected to salt milling treatment. The obtained kneaded product is poured into 3 liters of warm water, stirred for 1 hour while being heated to 70 ° C., made into a slurry, repeatedly filtered and washed with water to remove sodium chloride and diethylene glycol, and then dried at 80 ° C. overnight. 98 parts of pigment composition 42 (RP-42) were obtained. The average primary particle size was 25 nm.

[Example 70]
(Preparation of pigment composition 43 (RP-43))
3-amino-4-methoxybenzanilide, 103.8 parts, 24.5 parts of the base compound represented by the formula (9-b) are dispersed in 2000 parts of water, ice is added to adjust the temperature to 5 ° C., and 35% After adding 205 parts of an aqueous hydrochloric acid solution and stirring for 1 hour, an aqueous solution prepared by adding 37.5 parts of sodium nitrite to 110 parts of water was added and stirred for 2 hours. An aqueous solution consisting of 380 parts of an 80% aqueous acetic acid solution, 418 parts of a 25% aqueous sodium hydroxide solution, and 413 parts of water was added to form an aqueous diazonium salt solution. On the other hand, N- [2-methoxy-5-chlorophenyl] -3-hydroxy-2-naphthalenecarboxamide 155.3 parts, N- [4- (2-oxo-2,3-dihydro-1H-benzimidazole-5] -Il)]-3-Hydroxy-2-naphthalenecarboxamide (16.8 parts) and 25% aqueous sodium hydroxide solution (1344 parts) were dissolved in methanol (3500 parts) to obtain a coupler solution.
This coupler solution was poured into the 5 ° C. diazonium salt aqueous solution over 30 minutes to carry out a coupling reaction. The pH at this time was 4.4. After stirring for 3 hours and confirming the disappearance of the diazonium salt, the mixture was heated to 70 ° C., filtered, washed with water, and dried at 90 ° C. for 24 hours. I. Pigment Red 269 (PR269), Pigment Dispersant 2 (RD-2) represented by Formula (9), and C.I. I. 246.7 parts of pigment composition 43 (RP-43) which is a mixture of pigment red 176 (PR176) and pigment dispersant 27 (RD-27) represented by formula (38) was obtained. The average primary particle size was 26 nm.

[Example 71]
(Preparation of pigment composition 44 (RP-44))
100 parts of the obtained 43 (RP-43), 1200 parts of sodium chloride, and 120 parts of diethylene glycol were charged into a stainless steel 1 gallon kneader (manufactured by Inoue Seisakusho Co., Ltd.), kneaded at 60 ° C. for 6 hours, and subjected to salt milling treatment. The obtained kneaded product is poured into 3 liters of warm water, stirred for 1 hour while being heated to 70 ° C., made into a slurry, repeatedly filtered and washed with water to remove sodium chloride and diethylene glycol, and then dried at 80 ° C. overnight. 98 parts of pigment composition 44 (RP-44) were obtained. The average primary particle size was 25 nm.

[Example 72]
(Preparation of pigment composition 45 (RP-45))
Disperse 103.8 parts of 3-amino-4-methoxybenzanilide in 2000 parts of water, add ice to adjust the temperature to 5 ° C., add 205 parts of 35% aqueous hydrochloric acid and stir for 1 hour, and then add sodium nitrite 37 An aqueous solution prepared by adding 5 parts to 110 parts of water was added and stirred for 2 hours to obtain a diazonium salt aqueous solution. On the other hand, 143.2 parts of N- [2-methoxy-5-chlorophenyl] -3-hydroxy-2-naphthalenecarboxamide and 1344 parts of 25% aqueous sodium hydroxide solution were dissolved in 3500 parts of methanol to obtain a coupler solution. 39.8 parts of pigment dispersant 2 (RD-2) represented by formula (9) in a mixed solution of an aqueous solution consisting of 380 parts of an 80% aqueous acetic acid solution, 418 parts of an aqueous 25% sodium hydroxide solution, and 413 parts of water, C. I. Pigment Red 176 (PR176) 20.0 parts and Pigment Dispersant 27 (RD-27) 4.4 parts represented by Formula (38) were added to obtain a mixed slurry solution.
The 5 ° C. diazonium salt aqueous solution and the coupler solution were simultaneously injected into the mixed slurry solution over 30 minutes to perform a coupling reaction. The pH at this time was 4.4. After stirring for 3 hours and confirming the disappearance of the diazonium salt, the mixture was heated to 70 ° C., filtered, washed with water, and dried at 90 ° C. for 24 hours. I. Pigment Red 269 (PR269), Pigment Dispersant 2 (RD-2) represented by Formula (9), and C.I. I. 246.7 parts of a mixture of Pigment Red 176 (PR176) and Pigment Dispersant 27 (RD-27) represented by Formula (38) were obtained.
100 parts of the obtained mixture, 1200 parts of sodium chloride, and 120 parts of diethylene glycol were charged into a stainless steel 1 gallon kneader (manufactured by Inoue Seisakusho), kneaded at 60 ° C. for 6 hours, and subjected to salt milling treatment. The obtained kneaded product is poured into 3 liters of warm water, stirred for 1 hour while being heated to 70 ° C., made into a slurry, repeatedly filtered and washed with water to remove sodium chloride and diethylene glycol, and then dried at 80 ° C. overnight. 98 parts of pigment composition 45 (RP-45) were obtained. The average primary particle size was 24 nm.

<Other manufacturing examples>
[Production Example 1]
(Production of Red Pigment 1 (RC-1))
Commercially available C.I. I. 100 parts of Pigment Red 254 (PR254) ("Irgafore Red B-CF" manufactured by BASF), 1200 parts of sodium chloride, and 120 parts of diethylene glycol were charged into a 1 gallon kneader (manufactured by Inoue Seisakusho Co., Ltd.) at 6O 0 C. The mixture was kneaded for a time and subjected to salt milling. The obtained kneaded product is poured into 3 liters of warm water, stirred for 1 hour while being heated to 70 ° C., made into a slurry, repeatedly filtered and washed with water to remove sodium chloride and diethylene glycol, and then dried at 80 ° C. overnight. 98 parts of red pigment 1 (RC-1) were obtained. The average primary particle size was 37 nm.

[Production Example 2]
(Production of Red Pigment 2 (RC-2))
C. I. Pigment Red 254 (“Irgafore Red B-CF” manufactured by BASF) I. Pigment Red 177 (PR177) (“CROMOPHTAL RED A2B” manufactured by BASF) was used except that the red pigment 1 (RC-1) was produced, and 97 parts of red pigment 2 (RC-2) was obtained. . The average primary particle size was 33 nm.

[Production Example 3]
(Production of Red Pigment 3 (RC-3))
C. I. Pigment Red 254 (“Irgafore Red B-CF” manufactured by BASF) I. Pigment Red 242 (PR242) (“Novoperm Scallet 4RF” manufactured by Clariant) was used in the same manner as in the production of Red Pigment 1 (RC-1) to obtain 98 parts of Red Pigment 3 (RC-3). . The average primary particle size was 39 nm.

[Production Example 4]
(Production of Red Pigment 4 (RC-4))
C. I. Pigment Red 254 (“Irgafore Red B-CF” manufactured by BASF) I. Pigment Red 176 (PR176) (“Novoperm Carmine HF3C” manufactured by Clariant) was used in the same manner as in the production of Red Pigment 1 (RC-1) to obtain 98 parts of Red Pigment 4 (RC-4). . The average primary particle size was 35 nm.

[Production Example 5]
(Production of red pigment 5 (RC-5))
C. I. Pigment Red 254 (“Irgafore Red B-CF” manufactured by BASF) I. Pigment Orange 38 (PO38) ("Novoperm Red HF" manufactured by Clariant) was used in the same manner as in the production of Red Pigment 1 (RC-1) to obtain 97 parts of Red Pigment 5 (RC-5). . The average primary particle size was 39 nm.

[Production Example 6]
(Production of Red Pigment 6 (RC-6): Brominated diketopyrrolopyrrole pigment)
To a stainless steel reaction vessel equipped with a reflux tube, 200 parts of tert-amyl alcohol dehydrated with molecular sieves and 140 parts of sodium-tert-amyl alkoxide are added in a nitrogen atmosphere and heated to 100 ° C. with stirring to obtain an alcoholate solution. Prepared. On the other hand, 88 parts of diisopropyl succinate and 153.6 parts of 4-bromobenzonitrile were added to a glass flask and dissolved by heating to 90 ° C. with stirring to prepare a solution of these mixtures. The heated solution of the mixture was slowly dropped into the alcoholate solution heated to 100 ° C. at a constant rate over 2 hours with vigorous stirring. After completion of the dropwise addition, heating and stirring were continued at 90 ° C. for 2 hours to obtain an alkali metal salt of a diketopyrrolopyrrole pigment. Furthermore, 600 parts of methanol, 600 parts of water and 304 parts of acetic acid were added to a reaction vessel with a glass jacket, and cooled to -10 ° C. While cooling this mixture with a high-speed stirring disperser, rotating a shear disk having a diameter of 8 cm at 4000 rpm, the alkali metal salt of the diketopyrrolopyrrole pigment obtained above was cooled to 75 ° C. The solution was added in small portions. At this time, the rate of addition of the alkali metal salt of the diketopyrrolopyrrole pigment at 75 ° C. while cooling so that the temperature of the mixture consisting of methanol, acetic acid and water is always kept at −5 ° C. or lower. Was added in small portions over approximately 120 minutes. After addition of the alkali metal salt, red crystals were precipitated to form a red suspension. Subsequently, the obtained red suspension was washed with an ultrafiltration device at 5 ° C. and then filtered to obtain a red paste. This paste was re-dispersed in 3500 parts of methanol cooled to 0 ° C. to make a suspension with a methanol concentration of about 90%, and stirred at 5 ° C. for 3 hours to perform particle sizing and washing with crystal transition. Subsequently, the diketopyrrolopyrrole pigment aqueous paste obtained by filtration with an ultrafilter was dried at 80 ° C. for 24 hours and pulverized to obtain 150.8 parts of a brominated diketopyrrolopyrrole pigment. Got.

  100 parts of the brominated diketopyrrolopyrrole pigment (hereinafter referred to as DiBrDPP) obtained above, 1200 parts of sodium chloride, and 120 parts of diethylene glycol were charged into a stainless steel 1 gallon kneader (manufactured by Inoue Seisakusho) and kneaded at 60 ° C. for 6 hours. Then, salt milling was performed. The obtained kneaded product is poured into 3 liters of warm water, stirred for 1 hour while being heated to 70 ° C., made into a slurry, repeatedly filtered and washed with water to remove sodium chloride and diethylene glycol, and then dried at 80 ° C. overnight. 98 parts of red pigment 6 (RC-6) were obtained. The average primary particle size was 34 nm.

[Production Example 7]
(Production of red pigment 7 (RC-7))
C. I. Pigment Red 254 (“Irgafore Red B-CF” manufactured by BASF) I. Except for changing to Pigment Red 269 (PR269) (Permanent Carmine 3810 manufactured by Sanyo Color Co., Ltd.), the same procedure as in the production of Red Pigment 1 (RC-1) was carried out to obtain 98 parts of Red Pigment 7 (RC-7). The average primary particle size was 42 nm.

[Production Example 8]
(Production of red pigment 8 (RC-8))
125 parts of 3-amino-4-methoxybenzanilide are dispersed in 2000 parts of water, ice is added to adjust the temperature to 5 ° C., 205 parts of 35% aqueous hydrochloric acid is added, and the mixture is stirred for 1 hour. A water solution prepared by adding 110 parts to water was added, and the mixture was stirred for 2 hours. An aqueous solution consisting of 380 parts of an 80% aqueous acetic acid solution, 418 parts of a 25% aqueous sodium hydroxide solution, and 413 parts of water was added to form an aqueous diazonium salt solution. On the other hand, 154.4 parts of N- [2-methoxyphenyl] -3-hydroxy-2-naphthalenecarboxamide and 1344 parts of 25% aqueous sodium hydroxide solution were dissolved in 3500 parts of methanol to obtain a coupler solution.
This coupler solution was poured into the 5 ° C. diazonium salt aqueous solution over 30 minutes to carry out a coupling reaction. The pH at this time was 4.4. After stirring for 3 hours and confirming the disappearance of the diazonium salt, the mixture was heated to 70 ° C., filtered, washed with water, and dried at 90 ° C. for 24 hours. I. 276 parts of Pigment Red 261 (PR261) was obtained.
C. I. Pigment Red 254 ("Irgafore Red B-CF" manufactured by BASF) was obtained. I. Except having changed to pigment red 261 (PR261), it carried out similarly to manufacture of the red pigment 1 (RC-1), and obtained 98 parts of red pigment 8 (RC-8). The average primary particle size was 43 nm.

[Production Example 9]
(Production of red pigment 9 (RC-9))
C. I. Pigment Red 254 (“Irgafore Red B-CF” manufactured by BASF) I. Pigment Red 245 (PR245) (“FAST RED 30T” manufactured by Tokyo Color Materials Co., Ltd.) was used in the same manner as in the production of Red Pigment 1 (RC-1), and 98 parts of Red Pigment 9 (RC-9). Got. The average primary particle size was 44 nm.

[Production Example 10]
(Production of Red Pigment 10 (RC-10))
C. I. Pigment Red 254 (“Irgafore Red B-CF” manufactured by BASF) I. Pigment Red 147 (PR147) (“Permanent Pink F3B 01” manufactured by Clariant) was used in the same manner as in the production of Red Pigment 1 (RC-1) to obtain 98 parts of Red Pigment 10 (RC-10). It was. The average primary particle size was 43 nm.

(Table 1 continued)

<Method for producing colored composition>
[Example 76]
(Preparation of colored composition 1 (RM-1))
A mixture having the following composition was stirred and mixed so as to be uniform, and then dispersed with an Eiger mill (“Mini Model M-250 MKII” manufactured by Eiger Japan) for 5 hours using zirconia beads having a diameter of 0.5 mm. It filtered with a 0.0 micrometer filter, and the coloring composition 1 (RM-1) was produced.
Pigment composition 1 (RP-1) 10.0 parts Resin type dispersant ("BYK111" manufactured by Big Chemie) 3.0 parts Acrylic resin solution 1 35.0 parts Propylene glycol monomethyl ether acetate 52.0 parts

[Examples 77 to 120, 123 to 125, Comparative Examples 1 to 10]
(Coloring compositions 2 to 45, 48 to 60 (RM-2 to 45, 48 to 60)
Except having changed the pigment composition and the pigment dispersant as shown in Table 2, it was the same as the colored composition 1 (RM-1), and the colored compositions 2 to 45 (RM-2 to 45) and the colored composition, respectively. Articles 48-60 (RM-48-60) were produced.

[Example 121]
(Preparation of colored composition 46 (RM-46))
Coloring composition 1 except that 10.0 parts of pigment composition 1 (RP-1) was changed to 9.5 parts of red pigment 7 (RC-7) and 0.5 part of pigment dispersant 13 (RD-13) Colored composition 46 (RM-46) was produced in the same manner as (RP-1).

[Example 122]
(Preparation of colored composition 47 (RM-47))
Coloring composition 1 except that pigment composition 1 (RP-1) 10.0 was changed to 9.5 parts of pigment composition 22 (RP-22) and 0.5 parts of pigment dispersant 4 (RD-4) A colored composition 47 (RM-47) was produced in the same manner as (RP-1).

<Evaluation of coating film of colored composition>
The heat resistance, light resistance, foreign matter evaluation, and storage stability of the coating film produced using the obtained colored compositions 1 to 60 (RM-1 to 60) were performed by the following methods. Table 2 shows the evaluation results.

(Heat resistance evaluation)
The coloring composition was applied on a 100 mm × 100 mm, 1.1 mm thick glass substrate using a spin coater so that the dry film thickness was 2.0 μm, then dried at 70 ° C. for 20 minutes, and then 230 ° C. The coating film substrate (one aspect of the color filter) was produced by heating and cooling for 60 minutes. The chromaticity ([L * (1), a * (1), b * (1)]) of the obtained coating film with a C light source was measured with a microspectrophotometer ("OSP-SP100" manufactured by Olympus Optical Co., Ltd.). And measured. Further, as a heat resistance test, the sample was heated at 250 ° C. for 1 hour, and the chromaticity ([L * (2), a * (2), b * (2)]) with a C light source was measured. The color difference ΔEab * was determined and evaluated in the following four stages.
ΔEab * = √ ((L * (2)-L * (1)) 2+ (a * (2)-a * (1)) 2+ (b * (2)-b * (1)) 2)
A: ΔEab * is less than 1.0 (very good)
○: ΔEab * is 1.0 or more and less than 2.5 (good)
Δ: ΔEab * is 2.5 or more and less than 5.0 (defect)
×: ΔEab * is 5.0 or more (very poor)

(Light resistance evaluation)
A coated substrate is prepared in the same manner as in the heat resistance evaluation, and the chromaticity ([L * (1), a * (1), b * (1)]) with a C light source is measured with a microspectrophotometer ( Measurement was performed using “OSP-SP100” manufactured by Olympus Optical Co., Ltd. Subsequently, an ultraviolet cut filter (“COLORED OPTICAL part LASS L38” manufactured by Hoya Co., Ltd.) was applied on the substrate, and irradiated with ultraviolet rays for 100 hours using a 470 W / m ² xenon lamp, and then the chromaticity ( [L * (2), a * (2), b * (2)]) were measured, and the color difference ΔEab * was determined by the above formula and evaluated according to the same criteria as heat resistance.

(Coating foreign material evaluation)
The coloring composition was applied onto a glass substrate of 100 mm × 100 mm and 1.1 mm thickness using a spin coater so that the dry film thickness was 2.0 μm, then dried at 70 ° C. for 20 minutes, and then 230 A coating film substrate was prepared by heating and cooling at 60 ° C. for 60 minutes. The evaluation was performed using a Olympus system metal microscope “BX60”). The magnification was 500 times, and the number of particles that were observable in arbitrary 5 fields of view through transmission was counted. Evaluation was made in the following four stages.
A: Less than 5 foreign objects (very good)
○: The number of foreign matters is 5 or more and less than 10 (good)
Δ: The number of foreign matters is 10 or more and less than 60 (defects)
×: The number of foreign matters is 60 or more (very bad)

(Storage stability test method)
The viscosity at 25 ° C. of the colored composition was measured at a rotation speed of 20 rpm using an E-type viscometer (TUE-20L type manufactured by Toki Sangyo Co., Ltd.). The viscosity change rate was calculated from the initial viscosity on the day of preparation of the colored composition and the viscosity measured after storage for 7 days in a thermostatic chamber at 40 ° C., and the storage stability was evaluated according to the following criteria.
◎: Less than 10% (very good)
○: 10% or more, less than 20% (good)
Δ: 20% or more, less than 50% (defect)
×: 50% or more (very bad)

(Table 2 continued)

  As shown in Table 2, the colored composition using the pigment dispersant of the present invention had good results in the heat resistance, light resistance, coating foreign matter, and initial viscosity of the coating film.

  In particular, when comparing the colored composition using the pigment dispersant of the present invention and Comparative Examples 7 to 10 which are not used, there is a clear difference not only in the primary particle diameter but also in the coating film foreign matter and storage stability of the coating film. It was seen.

<Production method of photosensitive coloring composition>
[Example 126]
(Preparation of photosensitive coloring composition 1 (RR-1))
A mixture having the following composition was stirred and mixed so as to be uniform, and then filtered through a 1 μm filter to prepare photosensitive coloring composition 1 (RR-1).
Coloring composition 1 (RM-1) 19.5 parts Coloring composition 51 (RM-51) 23.5 parts Acrylic resin solution 2 8.2 parts Photopolymerizable monomer ("Aronix M402" manufactured by Toagosei Co., Ltd.) 2.8 parts Photopolymerization initiator ("Irgacure 907" manufactured by BASF) 2.0 parts Sensitizer ("EAB-F" manufactured by Hodogaya Chemical Co., Ltd.) 0.4 parts Propylene glycol monomethyl ether acetate 43.6 Part

[Examples 127 to 175, Comparative Examples 11 to 19]
(Photosensitive coloring composition 2 to 59 (RR-2 to 59))
Implementation was performed except that coloring composition 1 (RM-1) and coloring composition 51 (RM-51) were changed to the combinations and ratios of coloring compositions shown in Table 3 (ratio within 43 parts of the total amount of coloring compositions). In the same manner as in Example 126, photosensitive colored compositions 2 to 59 (RR-2 to 59) were obtained, respectively. In addition, about the ratio change, it was made to match | combine the chromaticity of x = 0.640, y = 0.330 with C light source in the case of coating-film evaluation.

<Evaluation of coating film of photosensitive coloring composition>
The brightness | luminance (color characteristic) of the coating film produced using the obtained photosensitive coloring composition 1-59 (RR-1 to 59) was evaluated by the following method. Table 3 shows the evaluation results.

(Luminance evaluation)
The photosensitive coloring composition is applied onto a 100 mm × 100 mm, 1.1 mm thick glass substrate using a spin coater, then dried at 70 ° C. for 20 minutes, and an integrated light quantity of 150 mJ is used using an ultrahigh pressure mercury lamp. UV exposure was performed at / cm ² and development was performed with an alkaline developer at 23 ° C. to obtain a coated substrate. Next, after heating at 230 ° C. for 60 minutes and allowing to cool, the luminance Y (C) of the obtained coating film substrate was measured using a microspectrophotometer (“OSP-SP100” manufactured by Olympus Optical Co., Ltd.). The prepared coated substrate was adjusted to chromaticity of x = 0.640 and y = 0.330 with a C light source after heat treatment at 230 ° C. As an alkaline developer, sodium carbonate 1.5% by mass, sodium hydrogen carbonate 0.5% by mass, an anionic surfactant (“Perex NBL” manufactured by Kao Corporation) 8.0% by mass and water 90% by mass are used. What was used. Regarding the luminance Y (C), it can be said that there is a clear difference if it is 0.1 point or more.

(Contrast ratio evaluation)
Using the obtained photosensitive coloring composition, a spin coater was used to produce a three-level coated substrate (film thickness) so that the dry film thickness was about 1 μm by changing the rotation speed. After coating, the film was dried in a hot air oven at 80 ° C. for 30 minutes, and then the film thickness and contrast ratio were measured. The contrast ratio (CR) at a film thickness of 1 μm was determined from the three points of data by the primary correlation method.

(Table 3 continued)

  From the results of Table 3, a photosensitive coloring composition having high luminance and high contrast could be produced by using the coloring composition using the pigment dispersant of the present invention.

<Production of color filter>
The green photosensitive coloring composition and the blue photosensitive coloring composition used for preparation of a color filter were produced. In addition, about the red, the photosensitive coloring composition 1 (RR-1) of this invention was used.

(Preparation of green coloring composition 1 (GM-1))
A mixture having the composition shown below was stirred and mixed uniformly, and dispersed with an Eiger mill (“Mini Model M-250 MKII” manufactured by Eiger Japan) for 5 hours using zirconia beads having a diameter of 0.5 mm, and then 5.0 μm. The green colored composition 1 (GM-1) was produced by filtering with a filter.
Green pigment (CI Pigment Green 36) 6.8 parts Yellow pigment (CI Pigment Yellow 150) 5.2 parts Resin type dispersant ("EFKA4300" manufactured by BASF) 1.0 part Acrylic resin solution 1 35.0 parts Propylene glycol monomethyl ether acetate 52.0 parts

(Preparation of green photosensitive coloring composition 1 (GR-1))
A mixture having the following composition was stirred and mixed so as to be uniform, and then filtered through a 1 μm filter to prepare green photosensitive coloring composition 1 (GR-1).
Green coloring composition 1 (GM-1) 42.0 parts Acrylic resin solution 2 13.2 parts Photopolymerizable monomer (“Aronix M402” manufactured by Toagosei Co., Ltd.) 2.8 parts Photopolymerization initiator (manufactured by BASF) "Irgacure 907") 2.0 parts Sensitizer ("EAB-F" manufactured by Hodogaya Chemical Co., Ltd.) 0.4 parts Ethylene glycol monomethyl ether acetate 39.6 parts

(Preparation of blue coloring composition 1 (BM-1))
A mixture having the composition shown below was stirred and mixed uniformly, and dispersed with an Eiger mill (“Mini Model M-250 MKII” manufactured by Eiger Japan) for 5 hours using zirconia beads having a diameter of 0.5 mm, and then 5.0 μm. The blue colored composition 1 (BM-1) was produced by filtering with a filter.
Blue pigment (CI Pigment Blue 15: 6) 7.2 parts Purple Pigment (CI Pigment Violet 23) 4.8 parts Resin type dispersant ("EFKA4300" manufactured by BASF) 1.0 part Acrylic resin Solution 1 35.0 parts Propylene glycol monomethyl ether acetate 52.0 parts

(Preparation of blue photosensitive coloring composition 1 (BR-1))
A mixture having the following composition was stirred and mixed so as to be uniform, and then filtered through a 1 μm filter to prepare a blue photosensitive coloring composition 1 (BR-1).
Blue coloring composition 1 (BM-1) 34.0 parts Acrylic resin solution 2 15.2 parts Photopolymerizable monomer (“Aronix M400” manufactured by Toagosei Co., Ltd.) 3.3 parts Photopolymerization initiator (manufactured by BASF) "Irgacure 907") 2.0 parts Sensitizer ("EAB-F" manufactured by Hodogaya Chemical Co., Ltd.) 0.4 parts Ethylene glycol monomethyl ether acetate 45.1 parts

  A black matrix was patterned on a glass substrate, and the photosensitive coloring composition 1 (RR-1) of the present invention was applied onto the substrate with a spin coater to form a colored film. The coating was irradiated with 300 mJ / cm 2 of ultraviolet rays through a photomask using an ultrahigh pressure mercury lamp. Next, spray development was performed with an alkaline developer composed of a 0.2% by weight aqueous sodium carbonate solution to remove unexposed portions, followed by washing with ion-exchanged water. The substrate was heated at 230 ° C. for 20 minutes to obtain a red filter segment. Formed. The formed red filter segment was x = 0.640 and y = 0.330 with a C light source. By the same method, green photosensitive coloring composition 1 (GR-1) x = 0.300, y = 0.600, blue photosensitive coloring composition 1 (BR-1) x = 0.150, y = 0.060, a green filter segment and a blue filter segment were formed to obtain a color filter.

  By using the photosensitive coloring composition 1 (RR-1) of the present invention, it was possible to produce a color filter with high luminance and high contrast. Further, even in a color display device using a white light-emitting organic EL element as a light source, it was possible to produce a high-luminance color filter.

That is, the present invention is a pigment composition comprising a pigment dispersant represented by the following general formula (1) or general formula (2) and a pigment, wherein the general formula (1) or the general formula (2) It is related with the pigment composition characterized by mass ratio of the pigment dispersant represented and a pigment being 35: 65-1: 99 .

[In General Formula (1), X ¹ is a hydrogen atom, an alkyl group, or an alkoxy group, X ² , X ³ , and X ⁵ are hydrogen atoms, and X ⁴ is a hydrogen atom or a halogen atom . is there. X ⁶ is a hydrogen atom, a halogen atom, an alkyl group, or an alkoxyl group. X ^{7 to} X ⁹ are each independently a hydrogen atom or a group represented by the following formula (a), (c) or (d), and X ⁸ or X ⁹ is represented by the formula (a). X ⁸ or X ⁹ is a group represented by the formula (c), or X ⁷ and / or X ⁹ is a group represented by the formula (d) . X ¹⁰ is a hydrogen atom.
In general formula (2), X ¹¹ is a hydrogen atom or a halogen atom, X ¹² and X ¹⁵ are hydrogen atoms, and X ¹³ and X ¹⁴ are each independently a hydrogen atom or a perfluoroalkyl group. It is. X ¹⁶ is a halogen atom or an alkyl group. X ^{17 to} X ¹⁹ are each independently a hydrogen atom or a group represented by the following formula (a), (c) or (d), and X ¹⁸ or X ¹⁹ is represented by the formula (a). X ¹⁸ or X ¹⁹ is a group represented by the formula (c), or X ¹⁷ and / or X ¹⁹ is a group represented by the formula (d) . X ²⁰ is a hydrogen atom. ]

[In the formula (d), Z ⁶ is CONH. R ²⁵ is a hydrogen atom, Ri alkoxyl group der, R ²⁹ is hydrogen atom, R ²⁶ to R ²⁸ is a group represented by hydrogen or the ^{formula, (a), R 26 ~R} 28 At least one of these is a group represented by the formula (a ) . ]

[In General Formula (1), X ¹ is a hydrogen atom, an alkyl group, or an alkoxy group, X ² , X ³ , and X ⁵ are hydrogen atoms, and X ⁴ is a hydrogen atom or a halogen atom . is there. X ⁶ is a hydrogen atom, a halogen atom, an alkyl group, or an alkoxyl group. X ^{7 to} X ⁹ are each independently a hydrogen atom or a group represented by the following formula (a), (c) or (d), and X ⁸ or X ⁹ is represented by the formula (a). X ⁸ or X ⁹ is a group represented by the formula (c), or X ⁷ and / or X ⁹ is a group represented by the formula (d) . X ¹⁰ is a hydrogen atom. ]

[In General Formula (2), X ¹¹ is a hydrogen atom or a halogen atom, X ¹² and X ¹⁵ are hydrogen atoms, and X ¹³ and X ¹⁴ are each independently a hydrogen atom or perfluoroalkyl. It is a group. X ¹⁶ is a halogen atom or an alkyl group. X ^{17 to} X ¹⁹ are each independently a hydrogen atom or a group represented by the following formula (a), (c) or (d), and X ¹⁸ or X ¹⁹ is represented by the formula (a). X ¹⁸ or X ¹⁹ is a group represented by the formula (c), or X ¹⁷ and / or X ¹⁹ is a group represented by the formula (d) . X ²⁰ is a hydrogen atom. ]

[In the formula (d), Z ⁶ is CONH. R ²⁵ is a hydrogen atom, Ri alkoxyl group der, R ²⁹ is hydrogen atom, R ²⁶ to R ²⁸ is a group represented by hydrogen or the ^{formula, (a), R 26 ~R} 28 At least one of these is a group represented by the formula (a ) . ]

In the general formula (2), X ¹¹ is a hydrogen atom or, preferably a halogen atom, a halogen atom is more preferable.

Examples of the amine component used for forming the substituent represented by the above formula (a), formula ( d ), and formula (c) include dimethylamine, diethylamine, methylethylamine, N, N-ethyl. Isopropylamine, N, N-ethylpropylamine, N, N-methylbutylamine, N, N-methylisobutylamine, N, N-butylethylamine, N, N-tert-butylethylamine, diisopropylamine, dipropylamine, N , N-sec-butylpropylamine, dibutylamine, di-sec-butylamine, diisobutylamine, N, N-isobutyl-sec-butylamine, N, N-dimethylaminomethylamine, N, N-dimethylaminoethylamine, N, N-dimethylaminoamylamine, N, N-dimethylaminobu Ruamine, N, N-diethylaminoethylamine, N, N-diethylaminopropylamine, N, N-diethylaminohexylamine, N, N-diethylaminobutylamine, N, N-diethylaminopentylamine, N, N-dipropylaminobutylamine, N , N-dibutylaminopropylamine, N, N-dibutylaminoethylamine, N, N-dibutylaminobutylamine and the like, but are not limited thereto.

Hereinafter, specific examples of the substituent (abbreviated as L) represented by the formula (a), the formula ( d ), and the formula (c) in the pigment dispersant used in the present invention will be described. However, it is not limited to these. C ₃ H ₇ and n-C ₃ H ₇ are propyl groups, i-C ₃ H ₇ is isopropyl groups, C ₄ H ₉ is butyl groups, C ₃ H ₆ is propylene groups, and C ₄ H ₈ is butylene groups. Represents.

[Examples 29 to 45, 47 to 68, 73 to 75]
(Preparation of pigment compositions 2-18, 20-41, 46-48 (RP-2-18, 20-41, 46-48))
The azo pigment represented by the general formula (3), the pigment dispersant represented by the general formula (1) or the formula (2), the pigment dispersant represented by the general formula (4), and the general formula (5) Pigment compositions 2 to 18, 20 to 41, and 46 to 48 were prepared in the same manner as pigment composition 1 (RP-1) except that the azo pigments were changed as shown in Table 1.
The pigments used are shown below.
・ C. I. Pigment Red 147 (PR147) (“Permanent Pink F3B 01” manufactured by Clariant)
・ C. I. Pigment Red 245 (PR245) (“FAST RED 30T” manufactured by Tokyo Color Material Industries Co., Ltd.)
・ C. I. Pigment Red 176 (PR176) (“Novoperm Carmine HF3C” manufactured by Clariant)
Examples 73 and 74 (RP-46 and 47) are reference examples.

[Examples 77 to 120, 123 to 125, Comparative Examples 1 to 10]
(Coloring compositions 2 to 45, 48 to 60 (RM-2 to 45, 48 to 60)
Except having changed the pigment composition and the pigment dispersant as shown in Table 2, it was the same as the colored composition 1 (RM-1), and the colored compositions 2 to 45 (RM-2 to 45) and the colored composition, respectively. Articles 48-60 (RM-48-60) were produced.
Examples 123 and 124 (RM-48 and 49) are reference examples.

<Evaluation of coating film of colored composition>
The heat resistance, light resistance, foreign matter evaluation, and storage stability of the coating film produced using the obtained colored compositions 1 to 60 (RM-1 to 60) were performed by the following methods. Table 2 shows the evaluation results.
Examples 123 and 124 (RM-48 and 49) are reference examples.

[Examples 127 to 175, Comparative Examples 11 to 19]
(Photosensitive coloring composition 2 to 59 (RR-2 to 59))
Implementation was performed except that coloring composition 1 (RM-1) and coloring composition 51 (RM-51) were changed to the combinations and ratios of coloring compositions shown in Table 3 (ratio within 43 parts of the total amount of coloring compositions). In the same manner as in Example 126, photosensitive colored compositions 2 to 59 (RR-2 to 59) were obtained, respectively. In addition, about the ratio change, it was made to match | combine the chromaticity of x = 0.640, y = 0.330 with C light source in the case of coating-film evaluation.
Examples 173 and 174 (RR-48 and 49) are reference examples.

<Evaluation of coating film of photosensitive coloring composition>
The brightness | luminance (color characteristic) of the coating film produced using the obtained photosensitive coloring composition 1-59 (RR-1 to 59) was evaluated by the following method. Table 3 shows the evaluation results.
Examples 173 and 174 (RR-48 and 49) are reference examples.

[In General Formula (1), X ¹ is a hydrogen atom, an alkyl group, or an alkoxy group, X ² , X ³ , and X ⁵ are hydrogen atoms, and X ⁴ is a hydrogen atom or a halogen atom. is there. X ⁶ is a hydrogen atom, a halogen atom, an alkyl group, or an alkoxyl group. X ^{7 to} X ⁹ are each independently a hydrogen atom or a group represented by the following formula (a ) or (d), and is X ⁸ or X ⁹ a group represented by the formula (a)? , X ⁷ and / or X ⁹ are groups represented by the formula (d). X ¹⁰ is a hydrogen atom.
In General Formula (2), X ¹¹ is a hydrogen atom or a halogen atom, X ¹² and X ¹⁵ are hydrogen atoms, and X ¹³ and X ¹⁴ are each independently a hydrogen atom or a perfluoroalkyl group. It is. X ¹⁶ is a halogen atom or an alkyl group. X ^{17 to} X ¹⁹ are each independently a hydrogen atom or a group represented by the following formula (a ) or (d), and is X ¹⁸ or X ¹⁹ a group represented by the formula (a)? , X ¹⁷ and / or X ¹⁹ is a group represented by the formula (d). X ²⁰ is a hydrogen atom. ]

[In General Formula (1), X ¹ is a hydrogen atom, an alkyl group, or an alkoxy group, X ² , X ³ , and X ⁵ are hydrogen atoms, and X ⁴ is a hydrogen atom or a halogen atom. is there. X ⁶ is a hydrogen atom, a halogen atom, an alkyl group, or an alkoxyl group. X ^{7 to} X ⁹ are each independently a hydrogen atom or a group represented by the following formula (a ) or (d), and is X ⁸ or X ⁹ a group represented by the formula (a)? , X ⁷ and / or X ⁹ are groups represented by the formula (d). X ¹⁰ is a hydrogen atom. ]

[In General Formula (2), X ¹¹ is a hydrogen atom or a halogen atom, X ¹² and X ¹⁵ are a hydrogen atom, and X ¹³ and X ¹⁴ are each independently a hydrogen atom or a perfluoroalkyl. It is a group. X ¹⁶ is a halogen atom or an alkyl group. X ^{17 to} X ¹⁹ are each independently a hydrogen atom or a group represented by the following formula (a ) or (d), and is X ¹⁸ or X ¹⁹ a group represented by the formula (a)? , X ¹⁷ and / or X ¹⁹ is a group represented by the formula (d). X ²⁰ is a hydrogen atom. ]

In General Formula (1), any one of X ^{7 to} X ⁹ is preferably a group represented by Formula (a ) or Formula (d). In a more preferred embodiment, (i): when X ⁹ is a group represented by the formula (a ) or the formula (d), and X ⁷ and X ⁸ are hydrogen atoms, more preferably the formula (a ), Or a group represented by formula (d), (ii): when X ⁸ is a group represented by formula (a ) , and X ⁷ and X ⁹ are hydrogen atoms, Preferably, when it is a group represented by the formula (a), (iii): X ⁷ and X ⁹ are groups represented by the formula (d), and X ⁸ is a hydrogen atom. .

In General Formula (2), any one of X ^{17 to} X ¹⁹ is preferably a group represented by Formula (a ) or Formula (d). In a more preferred embodiment, when (i): X ¹⁹ is a group represented by formula (a ) or (d), and X ¹⁷ and X ¹⁸ are hydrogen atoms, (ii): X ¹⁸ Is a group represented by the formula (a ) , and when X ¹⁷ and X ¹⁹ are hydrogen atoms, (iii): X ¹⁷ and X ¹⁹ are groups represented by the formula (d), An example is when X ¹⁸ is a hydrogen atom. In a more preferred embodiment, when (iv): X ¹⁹ is a group represented by the formula (a) or (d), and X ¹⁷ and X ¹⁸ are hydrogen atoms, (v): X ¹⁸ is a group represented by the formula (a), and X ¹⁷ and X ¹⁹ are hydrogen atoms.

Examples of the amine component used to form the substituents represented by the above formulas (a) and (d ) include dimethylamine, diethylamine, methylethylamine, N, N-ethylisopropylamine, N, N -Ethylpropylamine, N, N-methylbutylamine, N, N-methylisobutylamine, N, N-butylethylamine, N, N-tert-butylethylamine, diisopropylamine, dipropylamine, N, N-sec-butyl Propylamine, dibutylamine, di-sec-butylamine, diisobutylamine, N, N-isobutyl-sec-butylamine, N, N-dimethylaminomethylamine, N, N-dimethylaminoethylamine, N, N-dimethylaminoamylamine N, N-dimethylaminobutylamine, N, N -Diethylaminoethylamine, N, N-diethylaminopropylamine, N, N-diethylaminohexylamine, N, N-diethylaminobutylamine, N, N-diethylaminopentylamine, N, N-dipropylaminobutylamine, N, N-dibutylamino Examples include, but are not limited to, propylamine, N, N-dibutylaminoethylamine, N, N-dibutylaminobutylamine and the like.

Therefore, as a preferable embodiment of the general formula (1),
X ¹ is a hydrogen atom, an alkyl group or an alkoxyl group,
X ² , X ³ , X ⁵ and X ¹⁰ are hydrogen atoms;
X ⁴ is a hydrogen atom or a halogen atom,
X ⁶ is a hydrogen atom, a halogen atom, an alkyl group, or an alkoxyl group,
X ⁷ , X ⁸ and X ⁹ are each a hydrogen atom, a group represented by the formula (a ) or the formula (d), and at least one of X ⁷ , X ⁸ and X ⁹ is represented by the formula (a ) Or a group represented by formula (d),
In the formula (a), Z ¹ is CO, Z ² is NH, n is an integer of 1 to 8, and R ¹⁶ and R ¹⁷ are alkyl groups having 1 to 8 carbon atoms. Yes ,
In formula (d), Z ⁶ is CONH, R ²⁵ and R ²⁹ are hydrogen atoms, and R ²⁶ , R ²⁷ and R ²⁸ are each independently represented by a hydrogen atom or formula (a). It is preferable that at least one of R ²⁶ , R ²⁷ and R ²⁸ is a group represented by the formula (a).

Moreover, as a preferable aspect of General formula (2),
X ¹¹ is a hydrogen atom or a halogen atom,
X ¹² , X ¹³ , X ¹⁵ and X ²⁰ are hydrogen atoms;
X ¹⁴ is a hydrogen atom or a perfluoroalkyl group,
X ¹⁶ is a halogen atom or an alkyl group,
X ¹⁷ , X ¹⁸ and X ¹⁹ are a hydrogen atom, a group represented by formula (a ) or formula (d), and at least one of X ¹⁷ , X ¹⁸ and X ¹⁹ is represented by formula (a ) Or a group represented by formula (d),
In the formula (a), Z ¹ is CO, Z ² is NH, n is an integer of 1 to 8, and R ¹⁶ and R ¹⁷ are alkyl groups having 1 to 8 carbon atoms. Yes ,
In formula (d), Z ⁶ is CONH, R ²⁵ and R ²⁹ are hydrogen atoms, and R ²⁶ , R ²⁷ and R ²⁸ are each independently represented by a hydrogen atom or formula (a). It is preferable that at least one of R ²⁶ , R ²⁷ and R ²⁸ is a group represented by the formula (a).

Hereinafter, specific examples of the substituents (abbreviated as L ) represented by the formula (a) and the formula (d ) in the pigment dispersant used in the present invention will be described, but the present invention is limited to these. It is not a thing. C ₃ H ₇ and n-C ₃ H ₇ are propyl groups, i-C ₃ H ₇ is isopropyl groups, C ₄ H ₉ is butyl groups, C ₃ H ₆ is propylene groups, and C ₄ H ₈ is butylene groups. Represents.

[Examples 29 to 45, 47 to 68, 73 to 75]
(Preparation of pigment compositions 2-18, 20-41, 46-48 (RP-2-18, 20-41, 46-48))
The azo pigment represented by the general formula (3), the pigment dispersant represented by the general formula (1) or the formula (2), the pigment dispersant represented by the general formula (4), and the general formula (5) Pigment compositions 2 to 18, 20 to 41, and 46 to 48 were prepared in the same manner as pigment composition 1 (RP-1) except that the azo pigments were changed as shown in Table 1.
The pigments used are shown below.
・ C. I. Pigment Red 147 (PR147) (“Permanent Pink F3B 01” manufactured by Clariant)
・ C. I. Pigment Red 245 (PR245) (“FAST RED 30T” manufactured by Tokyo Color Material Industries Co., Ltd.)
・ C. I. Pigment Red 176 (PR176) (“Novoperm Carmine HF3C” manufactured by Clariant)
Examples 47 and 48 (RP-20 and 21) and Examples 73 and 74 (RP-46 and 47) are reference examples.

[Examples 77 to 120, 123 to 125, Comparative Examples 1 to 10]
(Coloring compositions 2 to 45, 48 to 60 (RM-2 to 45, 48 to 60)
Except having changed the pigment composition and the pigment dispersant as shown in Table 2, it was the same as the colored composition 1 (RM-1), and the colored compositions 2 to 45 (RM-2 to 45) and the colored composition, respectively. Articles 48-60 (RM-48-60) were produced.
Examples 95 and 96 (RM-20 and 21) and Examples 123 and 124 (RM-48 and 49) are reference examples.

<Evaluation of coating film of colored composition>
The heat resistance, light resistance, foreign matter evaluation, and storage stability of the coating film produced using the obtained colored compositions 1 to 60 (RM-1 to 60) were performed by the following methods. Table 2 shows the evaluation results.
Examples 95 and 96 (RM-20 and 21) and Examples 123 and 124 (RM-48 and 49) are reference examples.

[Examples 127 to 175, Comparative Examples 11 to 19]
(Photosensitive coloring composition 2 to 59 (RR-2 to 59))
Implementation was performed except that coloring composition 1 (RM-1) and coloring composition 51 (RM-51) were changed to the combinations and ratios of coloring compositions shown in Table 3 (ratio within 43 parts of the total amount of coloring compositions). In the same manner as in Example 126, photosensitive colored compositions 2 to 59 (RR-2 to 59) were obtained, respectively. In addition, about the ratio change, it was made to match | combine the chromaticity of x = 0.640, y = 0.330 with C light source in the case of coating-film evaluation.
Examples 145 and 146 (RR-20 and 21) and Examples 173 and 174 (RR-48 and 49) are reference examples.

<Evaluation of coating film of photosensitive coloring composition>
The brightness | luminance (color characteristic) of the coating film produced using the obtained photosensitive coloring composition 1-59 (RR-1 to 59) was evaluated by the following method. Table 3 shows the evaluation results.
Examples 145 and 146 (RR-20 and 21) and Examples 173 and 174 (RR-48 and 49) are reference examples.

Claims (11)

A pigment dispersant represented by the following general formula (1) or general formula (2).
[In the general formula ^(1), X 1 ~X ⁵ each independently represent a hydrogen atom, a halogen atom, an alkyl group or an alkoxyl group. X ⁶ is a hydrogen atom, a halogen atom, an alkyl group, or an alkoxyl group. X ^{7 to} X ⁹ are each independently a hydrogen atom or a group represented by the following formula (a), (c) or (d), and at least one of X ^{7 to} X ⁹ is represented by the formula (a ), (C) or (d). X ¹⁰ is a hydrogen atom.
In the general formula (2), X ^{11 to} X ¹⁵ are each independently a hydrogen atom, a halogen atom, an alkyl group, a perfluoroalkyl group, or an alkoxyl group, and at least one of X ^{11 to} X ¹⁵ is a per A fluoroalkyl group; X ¹⁶ is a halogen atom or an alkyl group. X ^{17 to} X ¹⁹ are each independently a hydrogen atom or a group represented by the following formula (a), (c) or (d), and at least one of X ^{17 to} X ¹⁹ is represented by the formula (a ), (C) or (d). X ²⁰ is a hydrogen atom. ]

[In the formula (a), Z ¹ is CO or a direct bond, Z ² is NH or O, n is an integer of 1 to 10, and R ¹⁶ and R ¹⁷ are alkyl groups. . ]

[In Formula (c), Z ⁴ represents CO or a direct bond, Z ⁵ represents NH, and R ²³ represents a group represented by Formula (a). R ²⁴ is an alkoxyl group or a group represented by the formula (a). ]

[In the formula (d), Z ⁶ is CONH. R ^{25 to} R ²⁹ are a hydrogen atom, an alkoxyl group, or a group represented by formula (a) or formula (c), and at least one of R ^{25 to} R ²⁹ is represented by formula (a) or formula (c ). ] In the general formula (1), X ^{7 to} X ⁹ are each independently a hydrogen atom or a group represented by the following formula (a), (c) or (d), and X ⁸ or X ⁹ is a formula Is a group represented by (a), X ⁸ or X ⁹ is a group represented by formula (c), or X ⁷ and / or X ⁹ is a group represented by formula (d) And
In the general formula (2), X ^{17 to} X ¹⁹ are each independently a hydrogen atom or a group represented by the following formula (a), (c) or (d), and X ¹⁸ or X ¹⁹ is a formula Is a group represented by (a), X ¹⁸ or X ¹⁹ is a group represented by formula (c), or X ¹⁷ and / or X ¹⁹ is a group represented by formula (d) The pigment dispersant according to claim 1, wherein In general formula (1), X ¹ is a hydrogen atom, an alkyl group, or an alkoxy group, X ² , X ³ , and X ⁵ are hydrogen atoms, and X ⁴ is a hydrogen atom or a halogen atom. ,
In General Formula (2), X ¹¹ is a hydrogen atom or a halogen atom, X ¹² and X ¹⁵ are hydrogen atoms, and X ¹³ and X ¹⁴ are each independently a hydrogen atom or a perfluoroalkyl group. And
In formula (d), R ²⁵ is a hydrogen atom or an alkoxyl group, R ²⁹ is a hydrogen atom, R ^{26 to} R ²⁸ are a hydrogen atom or a group represented by formula (a), at least one pigment dispersing agent according to claim 1 or 2, wherein a group represented by formula (a) of the R ²⁶ to R ^28.   A pigment composition comprising the pigment dispersant according to claim 1 and a pigment.   The pigment composition according to claim 4, wherein a mass ratio of the pigment dispersant represented by the general formula (1) and / or the general formula (2) to the pigment is 35:65 to 1:99. object. The pigment composition according to claim 4 or 5, wherein the pigment is an azo pigment represented by the following general formula (3).
[In General Formula (3), A represents a hydrogen atom or a phenyl group. R ¹ represents a hydrogen atom, a halogen atom, a trifluoromethyl group, an alkyl group having 1 to 4 carbon atoms, or an alkoxyl group having 1 to 4 carbon atoms. R ^{2 to} R ⁶ are each independently a hydrogen atom, a halogen atom, a cyano group, a nitro group, a trifluoromethyl group, an alkyl group having 1 to 4 carbon atoms, —OR ⁸ , —COOR ⁹ , —CONHR ¹⁰ , It represents an -NHCOR ¹¹ or -SO ₂ NHR ^12. R ⁸ to R ¹² each independently represent a hydrogen atom or an alkyl group having 1 to 4 carbon atoms. ] The pigment composition according to any one of claims 4 to 6, further comprising a pigment dispersant represented by the following general formula (4) and an azo pigment represented by (5).
[In General Formula (4), X ⁶ represents a hydrogen atom, a halogen atom, an alkyl group, or an alkoxyl group. X ^{7 to} X ⁹ are each independently a hydrogen atom or a group represented by the following formula (a), (c) or (d), and at least one of X ^{7 to} X ⁹ is represented by the formula (a ), (C) or (d). X ¹⁰ is a hydrogen atom.
In general formula (5), A represents a hydrogen atom or a phenyl group. R ¹ represents a hydrogen atom, a halogen atom, a trifluoromethyl group, an alkyl group having 1 to 4 carbon atoms, or an alkoxyl group having 1 to 4 carbon atoms.

[In the formula (a), Z ¹ is CO or a direct bond, Z ² is NH or O, n is an integer of 1 to 10, and R ¹⁶ and R ¹⁷ are alkyl groups. . ]

[In Formula (c), Z ⁴ represents CO or a direct bond, Z ⁵ represents NH, and R ²³ represents a group represented by Formula (a). R ²⁴ is an alkoxyl group or a group represented by the formula (a). ]

[In the formula (d), Z ⁶ is CONH. R ^{25 to} R ²⁹ are a hydrogen atom, an alkoxyl group, or a group represented by formula (a) or formula (c), and at least one of R ^{25 to} R ²⁹ is represented by formula (a) or formula (c ). ] 1 to 35% by weight of a pigment dispersant represented by the general formula (1) and / or the general formula (2),
The azo pigment represented by the general formula (3) is 50 to 93% by weight,
The pigment dispersant represented by the general formula (4) is 0.1 to 10% by weight,
The azo pigment represented by the general formula (5) is 5 to 25% by weight,
The pigment composition according to claim 7, wherein   A coloring composition containing a coloring agent, a binder resin, and an organic solvent, wherein the coloring agent contains the pigment composition according to any one of claims 4 to 8.   The colored composition according to claim 9, further comprising a photopolymerizable monomer.   A color filter comprising a filter segment formed from the colored composition according to claim 9 or 10 on a substrate.