JP2014016593A - Coloring composition for color filter, and color filter - Google Patents

Abstract

PROBLEM TO BE SOLVED: To provide a coloring composition for a color filter, which exhibits high brightness even when it is subjected to heat treatment of 230°C or higher in a color filter forming process, and to provide a highly bright color filter formed using the same.SOLUTION: A coloring composition for a color filter contains a colorant [A], a binder resin, and an organic solvent. The colorant [A] contains; a salt-forming compound [A1] comprising any one selected from a group consisting of triarylmethane-based basic dye, a flavin-based basic dye, an auramine-based basic dye, a safranine-based basic dye, a phloxin-based basic dye, and a methylene blue-based basic dye, and a counter compound with a molecular weight of 200 to 3,500; and a xanthene-based pigment [A2].

Description

  The present invention relates to a colored composition for a color filter used for manufacturing a color filter used for a color liquid crystal display device, a color image pickup tube element, and the like, and a color filter including a filter segment formed using the same. is there.

In the liquid crystal display device, a liquid crystal material and a pixel are interposed between two polarizing plates, a voltage is applied to each pixel to change the alignment state of the liquid crystal material, and the degree of polarization of light passing through the first polarizing plate is changed. It is a display device that changes and controls the transmitted light passing through the second polarizing plate to display the screen.
By providing a color filter between the two polarizing plates, color display becomes possible, and it has come to be used for televisions, personal computers, monitors and the like.

  The color filter is provided with a grid-like light-shielding film black matrix (hereinafter referred to as BM) for the purpose of preventing color mixture of transmitted light and increasing display contrast on a transparent substrate such as a glass plate, and then a plurality of colors (usually red, Green and blue) filter segments are provided. The filter segments are as fine as several microns to several hundreds of microns, and the filter segments are arranged in the form of fine bands (stripes) of two or more different hues (stripe arrangement), or are arranged vertically and horizontally. (Delta arrangement) etc. The filter segment and the BM are formed by drying at a high temperature of generally 200 ° C. or higher, preferably 230 ° C. by applying a coloring composition.

  In a color liquid crystal display device, a transparent electrode for driving a liquid crystal is formed on a color filter by vapor deposition or sputtering, and an alignment film for aligning the liquid crystal in a certain direction is formed thereon. In order to sufficiently obtain the performance of these transparent electrodes and alignment films, the formation thereof must generally be performed at a high temperature of 200 ° C. or higher, preferably 230 ° C. or higher. For this reason, at present, as a method for producing a color filter, a method called a pigment dispersion method using a pigment having excellent light resistance and heat resistance as a colorant is mainly used.

The quality required for color liquid crystal display devices includes high image quality and low power consumption.
In order to achieve these, color filters with high brightness, high contrast, and high resolution are required.
In particular, in recent years, from the viewpoint of power consumption, the brightness of color filters has been increasing.
When a color filter with high brightness is used, the light transmittance is high, so that the number of backlights that are light sources can be reduced and power consumption can be reduced.

  Conventional color filters have been able to achieve high brightness and a wide color display area by combining a blue filter segment with a copper phthalocyanine pigment and a dioxazine pigment. However, as described above, higher brightness is required for the color filter.

  Further, xanthene dyes are known as dyes exhibiting a magenta color. In particular, the spectrum of xanthene dyes has a high transmittance in the vicinity of 425 to 500 nm when compared with blue pigments such as copper phthalocyanine pigments and cyanine pigments. When a segment is produced, it has been proposed that a blue filter segment with higher brightness can be obtained. (For example, see Patent Documents 1 and 2)

  As described above, a technique for dissolving a dye, not a pigment, in a resin or the like as a colorant has been proposed (see, for example, Patent Document 3). In addition, an ink for a color filter containing a phthalocyanine dye and a xanthene dye has been studied. In particular, it was a combination of a direct dye and an acid dye, but although the color developability was good, it was inferior in heat resistance and light resistance and was not satisfactory. (For example, see Patent Document 4)

  Further, it has been proposed to use a triarylmethane dye and a xanthene dye together as a blue pixel for a color filter. However, as described above, since the dye has inferior weather resistance compared to the pigment, sufficient weather resistance cannot be obtained by simply mixing the dyes, leaving room for improvement. . (For example, see Patent Document 5)

  Furthermore, in order to improve heat resistance, light resistance, and solvent resistance, it is also proposed to use a salt of triarylmethane dye and aromatic sulfonic acid or a triarylmethane basic dye as a color filter colorant. (See, for example, Patent Document 6). However, a salt-forming compound of a triarylmethane-based basic dye and an aromatic monosulfonic acid has a drawback that its durability is poor because its molecular weight is small.

JP 2009-265641 A JP 2010-32999 A JP-A-6-75375 JP-A-8-327811 Japanese Patent Laid-Open No. 11-223720 JP-A-20-304766

  An object of the present invention is to provide a high brightness color filter coloring composition that can withstand heat treatment at 230 ° C., and a high brightness color filter formed using the color filter coloring composition.

  As a result of intensive studies, the inventors of the present invention contain a specific salt-forming compound [A1] and a xanthene dye [A2] as a colorant, and thus have excellent heat resistance and chemical resistance, and lightness. The present inventors have found that a colored composition for color filters having a high level can be obtained, and have reached the present invention.

  That is, the present invention is a color filter coloring composition containing a colorant [A], a binder resin, and an organic solvent, wherein the colorant [A] is a triarylmethane basic dye or a flavin basic. A structure comprising any one selected from the group consisting of a dye, an auramine basic dye, a safranin basic dye, a phloxine basic dye, and a methylene blue basic dye, and a counter compound having a molecular weight in the range of 200 to 3,500. The present invention relates to a coloring composition for a color filter comprising a salt compound [A1] and a xanthene dye [A2].

  The present invention also relates to the color composition for a color filter, wherein the basic dye constituting the salt-forming compound [A1] is a triarylmethane basic dye.

The present invention also relates to the color composition for a color filter, wherein the xanthene dye [A2] is a salt forming compound of a xanthene acid dye and / or a sulfonic acid amide compound of a xanthene acid dye.
In the present invention, the xanthene acid dye is C.I. I. Acid Red 52, C.I. I. Acid Red 87, C.I. I. Acid Red 92, C.I. I. Acid Red 289, and C.I. I. It is at least one selected from the group consisting of Acid Red 388, and relates to the coloring composition for a color filter.

  Furthermore, it is related with the said coloring composition for color filters characterized by containing a photopolymerizable monomer and / or a photoinitiator.

  The present invention relates to a color filter comprising a filter segment formed on the base material from the color filter coloring composition.

  With the color filter coloring composition of the present invention, even when heat treatment at 230 ° C. or higher is performed in the color filter forming step, a high brightness filter segment can be formed because of excellent heat resistance. Accordingly, a color liquid crystal display device with low power consumption can be manufactured using this color filter.

In the present application, when expressed as “(meth) acrylate”, “(meth) acrylic acid”, or “(meth) acrylamide”, unless otherwise specified, “acrylate and / or methacrylate”, It shall represent “acrylic acid and / or methacrylic acid” or “acrylamide and / or methacrylamide”.
Further, “CI” mentioned below means a color index (CI).

The color filter coloring composition of the present invention is a color filter coloring composition containing a colorant [A], a binder resin, and an organic solvent, wherein the colorant [A] is a triarylmethane-based basic dye. , A flavin basic dye, an auramine basic dye, a safranin basic dye, a phloxine basic dye, and a methylene blue basic dye, and a counter having a molecular weight in the range of 200-3500 A salt-forming compound [A1] composed of the compound and a xanthene dye [A2].
First, various components of the coloring composition for a color filter of the present invention will be described.

<Colorant [A]>
The coloring composition of the present invention includes, as a colorant, a triarylmethane basic dye, a flavin basic dye, an auramine basic dye, a safranine basic dye, a Phloxine basic dye, and a methylene blue basic dye And a salt-forming compound [A1] consisting of a counter compound having a molecular weight in the range of 200 to 3500 and a xanthene dye [A2].

  The use ratio of the salt-forming compound [A1] and the xanthene-based dye [A2] is preferably 1 to 80 parts by weight of the xanthene-based dye [A2] with respect to 100 parts by weight of the salt-forming compound [A1]. More preferably, it is 5 to 60 parts by weight. When the addition amount of the xanthene dye [A2] is 1 part by weight or more and 80 parts by weight or less, the reproducible chromaticity region is widened, which is preferable.

<< Salt Forming Compound [A1] >>
The salt-forming compound [A1] is selected from the group consisting of triarylmethane basic dyes, flavin basic dyes, auramine basic dyes, safranine basic dyes, phloxine basic dyes, and methylene blue basic dyes. Any one selected and a counter compound having a molecular weight in the range of 200 to 3500 exhibit blue, purple, green, red, magenta, cyan, and yellow.
That is, C.I. I. Basic Blue, C.I. I. Basic Violet, C.I. I. Basic Green, C.I. I. Basic Red, C.I. I. Basic salt-forming compounds obtained using a basic dye classified as yellow or the like and a counter compound which is an anionic component having a molecular weight in the range of 200 to 3500, preferably 250 to 3500.

  A basic dye and a counter compound can be reacted by dissolving both in an aqueous solution, an alcohol solution or the like to obtain a salt-forming compound. Or it is also possible to obtain by melt-kneading both, heating.

By using such a salt-forming compound [A1], while having good spectral characteristics,
Even when used in an image display device using a color filter that is excellent in light resistance and heat resistance and requires high reliability, the characteristics are sufficient.

[Basic dye]
Basic dyes constituting the salt-forming compound [A1] are triarylmethane basic dyes, flavin basic dyes, auramine basic dyes, safranine basic dyes, Phloxine basic dyes, and methylene blue bases Selected from the group consisting of sex dyes.

Specifically, triarylmethane basic dyes include C.I. I. Basic Violet 1 (Methyl Violet), 3 (Crystal Violet), 14 (Magenta), C.I. I. Basic Blue 1 (Basic Cyanine 6G), 5 (Basic Cyanine EX), 7 (Victoria Pure Blue BO), 26 (Victoria Blue B conc.), C.I. I. Basic Green 1 (Brilliant Green GX), 4 (Malachite Green) and the like.
Among them, C.I. I. Basic Blue 7, Green 4, Green 1, and Violet 3 are preferably used.

Examples of the flavin basic dye include C.I. I. Basic Yellow 1, auramin basic dyes include C.I. I. Basic yellow 2, 3, and safranine basic dyes include C.I. I. Basic Red 2, Phloxine basic dyes include C.I. As basic red 12 and methylene blue basic dyes, C.I. I. Basic Blue 9 (Methylene Blue FZ, Methylene Blue B), 25 (Basic Blue GO), 24 (New Methylene Blue NX) and the like.
Among them, C.I. I. Basic Yellow 1, Blue 9, Blue 24 and Blue 25 are preferably used.

  Of these, a triarylmethane basic dye or a methylene blue basic dye is preferably used, and more preferably a triarylmethane basic dye, in terms of good color developability.

In forming a red pixel, a flavin basic dye as a complementary color is an effective material.
A methylene blue basic dye is a preferable material in that it exhibits a clear blue color and is excellent in heat resistance when used as a salt-forming dye. A flavin basic dye is a preferable material because it exhibits a clear yellowish color and is excellent in heat resistance when used as a salt-forming dye.

  The triarylmethane basic dye will be described in detail below.

(Triarylmethane basic dye)
The triarylmethane basic dye develops color when the NH ₂ or OH group located in the para position with respect to the central carbon takes a quinone structure by oxidation.
Depending on the number of NH ₂ and OH groups, it can be divided into the following three types. Among them, a triaminoarylmethane-based basic dye is preferable in terms of good blue, red and green coloring.
a) Diaminotriarylmethane-based basic dye b) Triaminotriarylmethane-based basic dye c) Rosolic acid-based basic dye having an OH group Triaminotriarylmethane-based basic dye, Diaminotriarylmethane-based basic dye The dye has a clear color tone and is excellent in sunlight fastness than the other dyes and is preferable. Further, diphenylnaphthylmethane basic dye and / or triarylmethane basic dye are preferable.

  A blue triarylmethane basic dye is preferable because it has spectral characteristics with high transmittance at 400 to 440 nm.

Summarizing the basic dyes by color,
Those that can be used for blue pixels are triarylmethane basic dyes and methylene blue basic dyes. I. Basic Blue 1 (Basic Cyanine 6G), 5 (Basic Cyanine EX), 7 (Victoria Pure Blue BO), 9 (Methylene Blue FZ, Methylene Blue B), 24 (New Methylene Blue NX), 25 (Basic) Blue GO), 26 (Victoria Blue B conc.) And the like.
In addition, safranin basic dyes and phloxine basic dyes exhibiting red, which will be described later, are also effective as complementary colors of blue pixels.
For example, a blue pixel with high brightness can be obtained by using a copper phthalocyanine pigment (CI Pigment Blue 15: 6) and a salt-forming compound derived from a basic dye exhibiting red. In particular, a combination of a copper phthalocyanine pigment (CI Pigment Blue 15: 6) and one using a rhodamine-based basic dye is preferable because high brightness is obtained.

  What can be used for the red pixel is a safranin-based basic dye or a phloxine-based basic dye. I. Basic Red 2 (Safranin basic dye), 12 (Phloxine basic dye) and the like. Further, a flavin-based basic dye exhibiting yellow as a complementary color of a red pixel is preferable.

  What can be used for the green pixel is a triarylmethane basic dye. I. Basic Green 1 (Brilliant Green GX), 4 (Malachite Green) and the like.

[Counter compound]
In the present invention, the counter compound as an anion component that can be preferably used is an anionic compound having a molecular weight in the range of 200 to 3,500, specifically, organic sulfonic acids such as heteropolyacids and aromatic sulfonic acids. Organic acids such as aromatic carboxylic acids and organic carboxylic acids such as fatty acids, and acid dyes.

The molecular weight of the counter compound is preferably in the range of 200 to 750. When the molecular weight of the counter compound is smaller than 200, the heat resistance and light resistance are lowered, and when the molecular weight of the counter compound is larger than 3500, the ratio of the coloring component per molecule is lowered and sufficient color development is achieved. It becomes impossible to do so.
Furthermore, modification with a resin having an acid group is also preferable.

  Among these, it is preferable that the counter compound as an anion component has the form of organic sulfonic acid, organic carboxylic acid, and acid dye. Of these, the organic sulfonic acid and acid dye forms are preferred. In this case, the preferred molecular weight range of the counter compound is 200 to 750.

The molecular weight and average molecular weight defined in the present invention are expressed by theoretical values converted from atomic weights. The first decimal place was calculated as a significant figure, and the calculated value was rounded off to exclude the minority.
When the counter compound is used as a sodium salt, the molecular weight is taken into account after replacing Na with H.

(Heteropoly acid)
The heteropoly acid, phosphotungstic acid _{H 3 (PW 12 0 40)} · nH 2 O (n ≒ 30:. ≒ is representative of the the nearly equal) (molecular weight 3421), silicotungstic acid _{H 4 (SiW 12 0 40)} · _{nH 2 O (n ≒ 30)} ( molecular weight 3418), phosphomolybdic acid _{H 3 (PMo 12 0 40)} · nH 2 O (n ≒ 30) ( molecular weight 2205), silicomolybdic acid _{H 3 (SiMo 12 0 40)} · nH ₂ O (n≈30) (molecular weight 2202), phosphotungstomolybdic acid H ₃ (PW _{12 -X} Mo _X 0 ₄₀ ) · nH ₂ O (n≈30) (6 <X <12), phosphovanadomolybdic acid _{H 15-X (PV 12 -} X Mo X 0 40) · nH 2 O (n ≒ 30) , and the like.
In addition, the molecular weight of phosphotungstomolybdic acid, phosphovanadomolybdic acid, and cytungstomolybdic acid is adjusted within the range of 2202 to 3421 by changing the composition ratio of phosphotungstic acid, phosphomolybdic acid, silicotungstic acid, silicomolybdic acid, and the like. be able to.
Moreover, when using a heteropolyacid as a counter compound, it is preferable that the average molecular weights are the range of 2820-3421. This is because, when molybdenum and tungsten are included, the proportion of tungsten is preferably more than 50%. In the case of phosphotungstomolybdic acid, a colorant having excellent transparency can be obtained by reducing the Mo content and including a large amount of W.

(Organic acid)
Examples of organic acids include sulfonic acids represented by the following general formula (1), sulfonic acids represented by the following general formula (2), organic sulfonic acids such as aromatic sulfonic acids, and organic carboxylic acids such as aromatic carboxylic acids and fatty acids. Or a metal salt thereof. Further, it may be a salt such as an ammonium salt.

  In the case of an organic acid, a more preferable molecular weight range is 200 to 400. More preferably, it is the range of 250-400. By setting the molecular weight within this range, it is possible to obtain a colorant having a good balance between resistance and coloring power, which is preferable.

[一般式（１）中、Ｒは、置換もしくは無置換のアルキル基、または、置換もしくは無置換のアルケニル基を表し、Ｍ＋はそれぞれ独立に、水素イオン、または金属イオンを表す。ｎは、１〜４の整数を表す。] Preferably, a sulfonic acid represented by the following general formula (1) or a metal salt thereof is used.

[In general formula (1), R represents a substituted or unsubstituted alkyl group or a substituted or unsubstituted alkenyl group, and M + each independently represents a hydrogen ion or a metal ion. n represents an integer of 1 to 4. ]

Specific examples of M include a hydrogen atom, an alkali metal, and an alkaline earth metal. Examples of the alkali metal include sodium, potassium, and lithium, and examples of the alkaline earth metal include calcium and magnesium.
When n is 2 or more, M may be the same or different.

[一般式（２）中、Ｒは、置換もしくは無置換のアルキル基、または、置換もしくは無置換のアルケニル基を表し、Ｍ’ｍ＋はそれぞれ独立に、金属イオンを表す。ｍは、２〜４の整数を表す。] Further, sulfonic acid represented by the following general formula (2) or a metal salt thereof is preferable.

[In General Formula (2), R represents a substituted or unsubstituted alkyl group or a substituted or unsubstituted alkenyl group, and M′m + each independently represents a metal ion. m represents an integer of 2 to 4. ]

  Specific examples of M ′ include alkaline earth metals and transition metals. Examples of the alkaline earth metal include calcium and magnesium, and examples of the transition metal include manganese and copper.

  Among these organic acids, an organic sulfonic acid or a metal salt thereof is preferable from the viewpoint of color reproducibility. Particularly, a sulfonic acid or a metal salt thereof represented by the general formula (1) is excellent in color reproducibility. Moreover, it is preferable.

  Examples of the substituted or unsubstituted alkyl group in R include a linear, branched, monocyclic or condensed polycyclic alkyl group having 1 to 30 carbon atoms, or one or more ester bonds having 2 to 30 carbon atoms ( -COO-) and / or a linear, branched, monocyclic or condensed polycyclic alkyl group containing an ether bond (-O-).

  Specific examples of the linear, branched, monocyclic or condensed polycyclic alkyl group having 1 to 30 carbon atoms include octyl group, nonyl group, decyl group, dodecyl group, octadecyl group, 2-ethylhexyl group, tert- An octyl group, a 4-decylcyclohexyl group, and the like can be mentioned, but are not limited thereto.

Specific examples of the linear or branched alkyl group having 2 to 30 carbon atoms and containing one or more ester bonds include —CH ₂ —CH ₂ —CH ₂ —COO—CH ₂ —CH ₃ , —CH _{2 -CH (-CH 3) -CH 2} -COO-CH 2 -CH 3, -CH 2 -CH 2 -CH 2 -OCO-CH 2 -CH 3, -CH 2 -CH 2 -CH 2 -CH 2 _{-COO-CH 2 -CH (CH 2} -CH 3) -CH 2 -CH 2 -CH 2 -CH 3, - (CH 2) 5-COO- (CH 2) 11-CH 3, -CH 2 -CH _{2 -CH 2 -CH- (COO-CH} 2 -CH 3) can be exemplified _2, etc., but is not limited thereto.

Specific examples of the linear or branched alkyl group having 2 to 30 carbon atoms and including one or more ether bonds include — (CH ₂ —CH ₂ —O) _t —CH ₃ (where t is from _{3 8), - (CH 2} -CH 2 -CH 2 -O) m-CH 3 ( wherein m is 2 to 5), but can be given, are limited to It is not a thing.

Specific examples of the monocyclic or condensed polycyclic alkyl group having 2 to 30 carbon atoms and optionally including one or more ether bonds include the following, but are not limited thereto. Absent.

Furthermore, specific examples of linear, branched, and alkyl groups having 3 to 30 carbon atoms and including one or more ester bonds (—COO—) and ether bonds (—O—) include —CH ₂ — _{CH 2 -COO-CH 2 -CH 2} -O-CH 2 -CH (CH 2 -CH 3) -CH 2 -CH 2 -CH 2 -CH 3, -CH 2 -CH 2 -COO-CH 2 -CH _{2 -O-CH 2 -CH 2 -O} -CH 2 -CH (CH 2 -CH 3) can be mentioned -CH ₂ -CH ₂ -CH ₂ -CH3, but not limited thereto.

  Examples of the substituted or unsubstituted alkenyl group for R include linear, branched, monocyclic or condensed polycyclic alkenyl groups having 1 to 18 carbon atoms. They may have a plurality of carbon-carbon double bonds in the structure. Specific examples include 1-octenyl group, 2-octenyl group, 3-octenyl group, 4-octenyl group, 5-octenyl group, 6-octenyl group, 7-octenyl group, and the like. It is not limited.

  Preferred compounds as the aromatic sulfonic acid include 1-naphthylamine-4,8-disulfonic acid (molecular weight 303), 1-naphthylamine-3,8-disulfonic acid (molecular weight 303), 1-naphthylamine-5,7-disulfonic acid ( Molecular weight 303), 1-naphthylamine-3,6-disulfonic acid (molecular weight 303), 1-naphthylamine-3,6,8-trisulfonic acid (kofoic acid) (molecular weight 383), 2-naphthylamine-6,8-disulfone Acid (molecular weight 303), 2-naphthylamine-1,6-disulfonic acid (molecular weight 303), 2-naphthylamine-4,8-disulfonic acid (molecular weight 303), 2-naphthylamine-3,6-disulfonic acid (amino-R) Acid) (molecular weight 303), 2-naphthylamine-5,7-disulfonic acid (amino J acid) (molecular weight 303) 1-naphthol-4,8-disulfonic acid (molecular weight 304), 1-naphthol-3,8-disulfonic acid (ε acid) (molecular weight 304), 1-naphthol-3,6-disulfonic acid (molecular weight 304), 1 -Naphthol-3,6,8-trisulfonic acid (molecular weight 384), 2-naphthol-6,8-disulfonic acid (molecular weight 304), 2-naphthol-3,6-disulfonic acid (R acid) (molecular weight 304) 2-naphthol-3,6,8-trisulfonic acid (molecular weight 384), N-phenyl-1-naphthylamine-8-sulfonic acid (molecular weight 299), Np-tolyl-1-naphthylamine-8-sulfonic acid (Molecular weight 313), N-phenyl-1-naphthylamine-5-sulfonic acid (molecular weight 299), N-phenyl-2-naphthylamine-6-sulfonic acid (molecular weight 29) 9), N-acetyl-7-amino-1-naphthol-3-sulfonic acid (molecular weight 281), N-phenyl-7-amino-1-naphthol-3-sulfonic acid (molecular weight 315), N-acetyl-6 -Amino-1-naphthol-3-sulfonic acid (molecular weight 281), N-phenyl-6-amino-1-naphthol-3-sulfonic acid (molecular weight 315), 1,8-dihydro-3,6-disulfonic acid ( Chromotropic acid) (molecular weight 320), 8-amino-1-naphthol-3,6-disulfonic acid (molecular weight 319), 8-amino-1-naphthol-5,7-disulfonic acid (molecular weight 319), 1,6 -Diamino-2-naphthol-4-sulfonic acid (molecular weight 254), 1-amino-2-naphthol-6,8-disulfonic acid (molecular weight 319), 1-amino-2-naphtho 3,6-disulfonic acid (molecular weight 319), 2,8-diamino-1-naphthol-5,7-disulfonic acid (molecular weight 334), 2,7-diamino-1-naphthol-3-sulfonic acid (molecular weight) 254), 2,6-diamino-1-naphthol-3-sulfonic acid (molecular weight 254), 2,8-diamino-1-naphthol-3,6-disulfonic acid (molecular weight 334), 2-amino-7-phenyl Amino-1-naphthol-3-sulfonic acid (molecular weight 330), 7-aminonaphthalene-1,3,6-trisulfonic acid (molecular weight 383), 1-amino-2,3,5-naphthalene trisulfonic acid (molecular weight) 383), 4-amino-1,2,3-naphthalene trisulfonic acid (molecular weight 383), 1-amino-2,3,6-naphthalene trisulfonic acid (molecular weight 383), 4 Amino-2,3,6-naphthalene trisulfonic acid (molecular weight 383), 4-amino-2,3,5-naphthalene trisulfonic acid (molecular weight 383), 4-amino-1,3,8-naphthalene trisulfonic acid (Molecular weight 383), 4-amino-1,3,7-naphthalene trisulfonic acid (molecular weight 383), 4-amino-1,3,6-naphthalene trisulfonic acid (molecular weight 383), 4-amino-1,3 , 5-naphthalene trisulfonic acid (molecular weight 383), 4-amino-1,2,8-naphthalene trisulfonic acid (molecular weight 383), 4-amino-1,2,7-naphthalene trisulfonic acid (molecular weight 383), 4-amino-1,2,6-naphthalene trisulfonic acid (molecular weight 383), 4-amino-1,2,5-naphthalene trisulfonic acid (molecular weight 383), 5-amino -1,2,6-naphthalene trisulfonic acid (molecular weight 383), 5-amino-1,3,6-naphthalene trisulfonic acid (molecular weight 383), 5-amino-1,4,6-naphthalene trisulfonic acid ( Molecular weight 383), 5-amino-2,3,6-naphthalene trisulfonic acid (molecular weight 383), 8-amino-1,3,7-naphthalene trisulfonic acid (molecular weight 383), 8-amino-1,2, 7-naphthalene trisulfonic acid (molecular weight 383), 5-amino-1,2,7-naphthalene trisulfonic acid (molecular weight 383), 5-amino-1,3,7-naphthalene trisulfonic acid (molecular weight 383), 8 -Aminonaphthalene-1,4,6-trisulfonic acid (molecular weight 383), 5-amino-2,3,7-naphthalene trisulfonic acid (molecular weight 383), 8-aminonaphth Len-1,3,6-trisulfonic acid (molecular weight 383), 8-amino-1,2,6-naphthalene trisulfonic acid (molecular weight 383), 5-amino-1,2,8-naphthalene trisulfonic acid ( Molecular weight 383), 5-amino-1,3,8-naphthalene trisulfonic acid (molecular weight 383), 5-amino-1,4,8-naphthalene trisulfonic acid (molecular weight 383), 4-amino-1,6,6 7-naphthalene trisulfonic acid (molecular weight 383), 8-amino-1,3,5-naphthalene trisulfonic acid (molecular weight 383), 8-amino-1,2,5-naphthalene trisulfonic acid (molecular weight 383), 5 -Amino-1,2,3-naphthalene trisulfonic acid (molecular weight 383), 5-amino-1,2,4-naphthalene trisulfonic acid (molecular weight 383), 8-amino-1,2, -Naphthalene trisulfonic acid (molecular weight 383), 8-amino-1,2,3-naphthalene trisulfonic acid (molecular weight 383), 2-amino-1,3,4-naphthalene trisulfonic acid (molecular weight 383), 2- Amino-1,3,5-naphthalene trisulfonic acid (molecular weight 383), 2-amino-1,3,6-naphthalene trisulfonic acid (molecular weight 383), 2-amino-1,3,7-naphthalene trisulfonic acid (Molecular weight 383), 2-amino-1,3,8-naphthalene trisulfonic acid (molecular weight 383), 2-amino-1,4,5-naphthalene trisulfonic acid (molecular weight 383), 2-amino-1,4 , 6-Naphthalenetrisulfonic acid (molecular weight 383), 2-amino-1,4,7-naphthalenetrisulfonic acid (molecular weight 383), 2-amino-1,4,8-na Talentrisulfonic acid (molecular weight 383), 3-amino-1,2,8-naphthalenetrisulfonic acid (molecular weight 383), 3-amino-1,2,7-naphthalenetrisulfonic acid (molecular weight 383), 3-amino -1,2,6-naphthalene trisulfonic acid (molecular weight 383), 3-amino-1,2,5-naphthalene trisulfonic acid (molecular weight 383), 6-amino-1,2,5-naphthalene trisulfonic acid ( Molecular weight 383), 6-amino-1,3,5-naphthalene trisulfonic acid (molecular weight 383), 6-amino-1,4,5-naphthalene trisulfonic acid (molecular weight 383), 2-amino-1,6,6 7-naphthalene trisulfonic acid (molecular weight 383), 7-amino-1,3,8-naphthalene trisulfonic acid (molecular weight 383), 7-amino-1,2,8-naphthalene Trisulfonic acid (molecular weight 383), 6-amino-1,2,7-naphthalene trisulfonic acid (molecular weight 383), 6-amino-1,3,7-naphthalene trisulfonic acid (molecular weight 383), 7-amino- 1,4,6-naphthalene trisulfonic acid (molecular weight 383), 7-amino-2,3,6-naphthalene trisulfonic acid (molecular weight 383), 7-amino-1,2,6-naphthalene trisulfonic acid (molecular weight) 383), 6-amino-1,2,8-naphthalene trisulfonic acid (molecular weight 383), 6-amino-1,3,8-naphthalene trisulfonic acid, 7-amino-1,4,5-naphthalene trisulfone Acid (molecular weight 383), 3-amino-1,6,7-naphthalene trisulfonic acid (molecular weight 383), 7-amino-1,3,5-naphthalene trisulfonic acid (molecular weight 83), 7-amino-1,2,5-naphthalene trisulfonic acid (molecular weight 383), 6-amino-1,2,3-naphthalene trisulfonic acid (molecular weight 383), 6-amino-1,2,4 -Naphthalene trisulfonic acid (molecular weight 383), 7-amino-1,2,4-naphthalene trisulfonic acid (molecular weight 383), 7-amino-1,2,3-naphthalene trisulfonic acid (molecular weight 383), 8- Acetylamino-1,3,6-naphthalene trisulfonic acid (molecular weight 383), 8-hydroxy-1,3,6-naphthalene trisulfonic acid (molecular weight 384), 2-hydroxynaphthalene-3,6,8-trisulfone Acid, 1,3,5,7-naphthalene tetrasulfonic acid (molecular weight 448), 1,2,3-naphthalene trisulfonic acid (molecular weight 368), 1,2,4-naphthal Talentrisulfonic acid (molecular weight 368), 1,2,5-naphthalenetrisulfonic acid (molecular weight 368), 1,2,6-naphthalenetrisulfonic acid (molecular weight 368), 1,2,7-naphthalenetrisulfonic acid ( Molecular weight 368), 1,2,8-naphthalene trisulfonic acid (molecular weight 368), 1,3,5-naphthalene trisulfonic acid (molecular weight 368), 1,3,6-naphthalene trisulfonic acid (molecular weight 368), 1 , 3,7-naphthalene trisulfonic acid (molecular weight 368), 1,3,8-naphthalene trisulfonic acid (molecular weight 368), 1,4,5-naphthalene trisulfonic acid (molecular weight 368), 1,4,6- Naphthalene trisulfonic acid (molecular weight 368), 2,3,5-naphthalene trisulfonic acid (molecular weight 368), 2,3,6-naphthalene trisulfone Acid (molecular weight 368), and the like.

  It is also preferable to use anthracenesulfonic acid (molecular weight 258), anthraquinone-2-sulfonic acid, anthraquinone-1-sulfonic acid (molecular weight 288).

2-amino-1-naphthalenesulfonic acid (tobias acid molecular weight 223), 4-amino-1-naphthalenesulfonic acid (naphthoic acid molecular weight 223), 8-amino-1-naphthalenesulfonic acid (peric acid molecular weight 223), 2-amino-6-naphthalenesulfonic acid (brennaic acid molecular weight 223), 1-amino-5-naphthalenesulfonic acid (lorenzic acid molecular weight 223), 5-amino-2-naphthalenesulfonic acid (molecular weight 223), 1 1 amino group and 1 sulfone such as amino-6-naphthalenesulfonic acid (molecular weight 223), 6-amino-1-naphthalenesulfonic acid (molecular weight 223), 3-amino-1-naphthalenesulfonic acid (molecular weight 223) It is preferable to use naphthylamine sulfonic acid having an acid group in terms of good heat resistance and light resistance. Shii is intended. Among these, 2-amino-1-naphthalenesulfonic acid (tobias acid) is particularly preferable.
Furthermore, 2-hydroxy-6-naphthalenesulfonic acid (shefic acid molecular weight 224), 1-hydroxy-4-naphthalenesulfonic acid (nevir-winter-acid: NW acid molecular weight 224), 1-hydroxy-5-naphthalenesulfonic acid ( It is also preferable to use hydroxynaphthalenesulfonic acid having one hydroxyl group and one sulfonic acid group, such as L acid molecular weight 224) and 2-hydroxy-8-naphthalenesulfonic acid (croseinic acid molecular weight 224).

  Among them, an organic sulfonic acid having 2 to 3 sulfone groups is preferable in that the color developability is good and high brightness can be achieved. When there are 4 or more sulfonic acids, environmental stability deteriorates and changes with time are likely to occur. With one sulfonic acid, the basic dye and the counter compound react in a 1: 1 ratio, and color is generated when the main color is used. May be worse.

  In the case of an organic sulfonic acid having a molecular weight in the range of 200 to 250, even if there is one sulfonic acid group per molecule, the color development is not impaired because the molecular weight of the counter compound itself is small. .

  Examples of organic carboxylic acids include tetrachlorophthalic acid (molecular weight 304), palmitic acid (molecular weight 257), stearic acid (molecular weight 285), arachidic acid (molecular weight 313), behenic acid (molecular weight 341), lignoceric acid (molecular weight 369). Oleic acid (molecular weight 282), elaidic acid (molecular weight 282), erucic acid (molecular weight 339), nervonic acid (molecular weight 367), linoleic acid (molecular weight 280), galolenic acid (molecular weight 278), arachidonic acid (molecular weight 305) ), Α-linolenic acid (molecular weight 278), stearidonic acid (molecular weight 276), eicosapentaenoic acid (molecular weight 302), docosahexaenoic acid (molecular weight 328), and the like.

(Acid dyes)
Further, the hue can be controlled by using a counter compound as an acid dye.
Examples of the acid dye include anthraquinone acid dyes, monoazo acid dyes, disazo acid dyes, oxazine acid dyes, amino ketone acid dyes, quinoline acid dyes, and triarylmethane acid dyes.

  More specifically, examples of the acid dye include C.I. I. Acid Yellow 11, C.I. I. Acid Yellow 23, C.I. I. Acid Green 3 (edible green No. 1), C.I. I. Acid Green 5 (edible green No. 2), C.I. I. Acid Green 9, C.I. I. Acid Green 16, C.I. I. Acid Green 19, C.I. I. Acid Green 25 etc.

  In the case of an acid dye, a more preferable molecular weight range is 300 to 750. More preferably, it is the range of 350-700. By setting the molecular weight within this range, a colorant having a good balance between weather resistance and coloring power can be obtained, which is preferable.

In the case of a red pixel, a red pixel can be obtained by salt formation with a safranin basic dye or a phloxine basic dye. At this time, preferred acid dyes are C.I. I. Acid Yellow 11 (molecular weight 380), C.I. I. Acid Yellow 23 (molecular weight 534), and the like.
In the case of a blue pixel, a blue pixel can be obtained by salt formation with the triarylmethane basic dye or methylene blue basic dye.

  In the case of a green pixel, the C.I. Green pixels can be obtained by salt formation with triarylmethane basic dyes such as I. Basic Green 1 (Brilliant Green GX) and 4 (Malachite Green). Preferred acid dyes at this time include C.I. I. Acid Green 3 (edible green No. 1) (molecular weight 690), C.I. I. Acid Green 5 (edible green No. 2) (molecular weight 761), C.I. I. Acid Green 9 (molecular weight 724), C.I. I. Acid Green 16 (molecular weight 560), C.I. I. Acid Green 19 (molecular weight 625), C.I. And I. Acid Green 25 (molecular weight 622).

[Salt making]
These salt-forming compounds of a basic dye and a counter compound can be synthesized by a conventionally known method. A specific method is disclosed in Japanese Patent Laid-Open No. 2003-215850.
An example of a triarylmethane-based basic dye is that a triarylmethane-based basic dye is dissolved in water, then an organic sulfonic acid or (organic sodium sulfonate) solution is added, and the chlorination treatment can be performed while stirring. That's fine. Here, a salt-forming compound in which the amino group (—NHC ₂ H ₅ ) portion in the triarylmethane-based basic dye and the sulfonic acid group (—SO ₃ H) portion of the organic sulfonic acid are bonded is obtained.
Here, the organic sulfonic acid can be dissolved in an alkali solution such as sodium hydroxide before the salt-forming treatment and used as a form of sodium sulfonate (—SO ₃ Na). In the present invention, a sulfonic acid group (—SO ₃ H) and a functional group (—SO ₃ Na) which is sodium sulfonate are also synonymous.

[Resin having an acid group]
Further, the salt-forming compound used in the present invention includes an acid group such as a carboxyl group (rosin-modified maleic acid resin (also referred to as rosin-modified fumaric acid resin)), rosin ester, polyester resin, and styrene acrylic copolymer having acid value. By adding a polymer or the like, the compatibility in the binder resin, the dispersibility, and the dispersibility in the solvent are greatly improved. As a result, the colorant, heat resistance, and light resistance are further improved as a colorant. Here, the acid group is preferably a carboxyl group (—COOH) or a sulfone group (—SO ₃ H).

The resin having an acid group preferably has a weight average molecular weight in the range of 400 to 12,000. More preferably, it is 400-6000, Most preferably, it is the range of 400-2000. By using the thing of this range, compatibility with a salt-forming compound becomes favorable and dispersion | distribution in a binder resin becomes favorable as a coloring agent.
Moreover, the measurement of the weight average molecular weight of resin which has an acid group here was performed on condition of the following.
Tetrahydrofuran (THF) was added to the specimen and allowed to stand for 12 hours, and then the THF solution of the specimen was filtered, and the molecular weight of the specimen dissolved in the filtrate was measured. The measurement was performed by gel permeation chromatography (GPC) method, and the molecular weight was calculated from a calibration curve prepared with standard polystyrene.
GPC device: HLC-8120GPC manufactured by Tosoh Corporation
Column: TSK Guardcolumn manufactured by Tosoh Corporation
Super-H-HT / SK-GEL / Super HM-M 3 flow rate: 1.0 ml / min (THF)

As the resin having an acid group, rosin-modified maleic acid resin is preferably used. The rosin-modified maleic resin has an acid-containing polar group portion and a non-polar rosin skeleton portion. The polar group portion having this acid is a carboxyl group portion derived from unreacted abietic acid and a carboxyl group of maleic acid, and reacts and is compatible with the polar group portion of the binder resin. Further, the nonpolar rosin skeleton part is compatible with the nonpolar part of the binder resin.
Moreover, the effect of the reaction between the acid component of the rosin-modified maleic resin and the amino group portion of the basic dye (unreacted basic dye in the salt-forming compound) is also great.

The acid value of the resin having an acid group is preferably in the range of 100 to 300 mgKOH / g. If the acid value is less than 100 mgKOH / g, the compatibility with the salt-forming compound is deteriorated. On the other hand, if the acid value is larger than 300 mgKOH / g, it becomes unfavorable because it causes poor developability when used as an alkali developing type colored resist described later.
Here, the acid value is a value measured by the method of JIS K-0070.

When a resin having an acid group is added to and mixed with the salt-forming compound used in the present invention, it can be obtained by the following method.
(1) A method in which a salt-forming compound is added after being dissolved in a solvent soluble in a resin having an acid group and then mixed in the solution. (2) A resin having an acid group is melted using a kneader or the like. Examples thereof include a method of adding and mixing the salt-forming compound in the state of being prepared, but it may be synthesized by any conventionally known method.

  An example of these is as follows. Here, an example using a triarylmethane basic dye and a rosin-modified maleic resin is shown.

(1) Method of adding a salt-forming compound after being dissolved in a solvent soluble in a resin having an acid group and mixing in the solution (1-1)
After the triarylmethane basic dye is dissolved in water, a counter compound such as organic sulfonic acid is added, and chlorination treatment is performed while stirring. Here, a salt-forming compound is obtained in which the amino group (—NHC ₂ H ₅ ) moiety in the triarylmethane-based basic dye and the acid group moiety in the counter are bonded.
Here, the counter compound can be dissolved in an alkali solution such as sodium hydroxide before the salt-forming treatment and used in the form of sodium sulfonate (—SO ₃ Na). In the present invention, a sulfonic acid group (—SO ₃ H) and a functional group (—SO ₃ Na) which is sodium sulfonate are also synonymous.

(1-2)
Next, it is a step of adding a rosin-modified maleic acid resin. After adding an aqueous alkali solution such as an aqueous sodium hydroxide solution to adjust to neutral, the rosin-modified maleic acid resin dissolved in the aqueous alkali solution is added and stirred. Mix while mixing. Next, a rosin-modified maleic resin is insolubilized by adding a mineral acid such as hydrochloric acid or sulfuric acid to make it acidic, and then filtered, washed and dried to obtain a composition. Moreover, what is necessary is just to obtain a desired particle size through a grinding | pulverization process if necessary.

(2) Method of adding and mixing salt-forming compound in melted resin having acid group using kneading machine etc. Salt-forming compound of the present invention and resin having acid group (rosin-modified maleic acid resin etc.) In a kneader such as a heating kneader, Banbury mixer, 3-roll mill, 2-roll mill, vibration mill, ball mill, attritor, extruder, etc. and thoroughly mixed at a temperature above the softening point of the resin having an acid group. Perform melt-kneading. Thereby, the salt-forming compound is dispersed in the resin having an acid group. The composition obtained here is in a state where a salt-forming compound is coated with a resin having an acid group. Furthermore, the composition may be obtained by coarsely crushing and pulverizing the composition to adjust to a desired particle size.

When the weight mixing ratio of the salt-forming compound of the present invention to the resin having an acid group (salt-forming compound: resin having an acid group) is in the range of 70:30 to 95: 5, a good colorant can be obtained. . If the ratio of the resin having an acid group is larger than 30% by weight, the color developability is deteriorated, that is, the color defect derived from the resin having an acid group is likely to occur, and the ratio of the resin having an acid group is 5% by weight. When it becomes smaller than this, the dispersibility improvement effect of the salt-forming compound in the binder resin becomes small.
More preferably, the weight mixing ratio of the salt-forming compound of the present invention and the resin having an acid group (salt-forming compound: resin having an acid group) is in the range of 75:25 to 90:10.

<< Xanthene dye [A2] >>
The xanthene colorant [A2] is red or purple, preferably has a dye form, and has any form of an oil-soluble dye, an acid dye, a direct dye, or a basic dye. Is preferred. In addition, lake pigments obtained by forming these dyes, forms of inorganic salts of acidic dyes having acidic groups such as sulfonic acid and carboxylic acid, salt-forming compounds of acidic dyes and nitrogen-containing compounds, and sulfonic acid amide compounds of acidic dyes It may be.

Among these, it is preferable to contain at least one xanthene-based oil-soluble dye, xanthene-based acid dye, salt-forming compound of xanthene-based acid dye, or sulfonic acid amide compound of xanthene-based acid dye because of excellent hue.
Particularly preferred is a salt forming compound of a xanthene acid dye or a sulfonic acid amide compound of a xanthene acid dye because high heat resistance, light resistance and solvent resistance can be imparted. Among these, a salt forming compound of a xanthene acid dye is preferable.

A red or purple color means C.I. I. Solvent Red, C.I. Oil soluble dyes such as I. solvent violet, C.I. I. Basic Red, C.I. Basic dyes such as I. basic violet, C.I. I. Acid Red, C.I. Acid dyes such as I. acid violet, C.I. I. Direct Red, C.I. I. Direct dyes such as direct violet, and the like.
Here, the direct dye has a sulfonic acid group (—SO ₃ H, —SO ₃ Na) in the structure, and in the present invention, the direct dye is regarded as a xanthene acid dye.

  The xanthene dye [A2] used in the present invention has a transmittance of 90% or more in the region of 650 nm in the transmission spectrum, a transmittance of 75% or more in the region of 600 nm, and a transmittance of 5% in the region of 500 to 550 nm. Hereinafter, those having a transmittance of 70% or more in the 400 nm region are preferable. More preferably, the transmittance is 95% or more in the region of 650 nm, the transmittance is 80% or more in the region of 600 nm, the transmittance is 10% or less in the region of 500 to 550 nm, and the transmittance is 75% in the region of 400 nm. That's it.

Of these, xanthene-based basic dyes and xanthene-based acid dyes have spectral characteristics with high transmittance at 400 to 450 nm, but are used for image display devices using color filters that require high reliability. In some cases, light resistance and heat resistance are problems, and the characteristics may not be sufficient.
Therefore, in order to improve these drawbacks, the xanthene-based basic dye is preferably a salt-forming compound obtained by salt formation using an organic acid or perchloric acid. As the organic acid, organic sulfonic acid or organic carboxylic acid is preferably used. Of these, naphthalenesulfonic acid such as tobias acid and perchloric acid are preferably used in terms of resistance.
In addition, xanthene-based acid dyes are chlorinated using a quaternary ammonium salt compound, a tertiary amine compound, a secondary amine compound, a primary amine compound, etc., and a resin component having these functional groups to form a salt forming compound, From the viewpoint of resistance, it is preferable to use a salt-forming compound or a sulfonamidated sulfonate amide compound.

  Among these, a salt component of a xanthene acid dye and / or a sulfonic acid amide compound of a xanthene acid dye is preferable because of excellent hue and resistance, and further, a counter component that functions as a counter ion. It is more preferable to use a compound prepared by using a quaternary ammonium salt compound and a sulfonic acid amide compound obtained by sulfonamidating a xanthene acid dye.

  Of the xanthene dyes [A2], rhodamine dyes are preferable because they are excellent in color developability and resistance.

  Hereinafter, the form of the xanthene dye [A2] used in the present invention will be specifically described in detail.

(Xanthene oil-soluble dye)
Xanthene oil-soluble dyes include CI Solvent Red 35, CI Solvent Red 36, CI Solvent Red 42, CI Solvent Red 43, CI Solvent Red 44, and C.I. I. Solvent Red 45, C.I. Solvent Red 46, C.I. Solvent Red 47, C.I. Solvent Red 48, C.I. Solvent Red 49, C.I. Solvent Red 72, C.I. Solvent Red 73, CI Solvent Red 109, CI Solvent Red 140, CI Solvent Red 141, CI Solvent Red 237, CI Solvent Red 246, CI Solvent Violet 2, CI Solvent Violet 10 and the like.
Among them, CI solvent red 35, CI solvent red 36, CI solvent red 49, CI solvent red 109, CI solvent red, which are rhodamine-based oil-soluble dyes having high color development Red 237, CI Solvent Red 246, and CI Solvent Violet 2 are more preferable.

(Xanthene basic dye)
Examples of xanthene basic dyes include C.I. I. Basic Red 1 (Rhodamine 6 GCP), 8 (Rhodamine G), C.I. I. Basic violet 10 (Rhodamine B) and the like. Among these, C.I. I. Basic Red 1, C.I. I. Basic violet 10 is preferably used.

(Xanthene acid dyes)
Examples of xanthene acid dyes include C.I. I. Acid Red 51 (erythrosin (edible red No. 3)), C.I. I. Acid Red 52 (Acid Rhodamine), C.I. I. Acid Red 87 (Eosin G (edible red No. 103)), C.I. I. Acid Red 92 (Acid Phloxin PB (edible red No. 104)), C.I. I. Acid Red 289, C.I. I. Acid Red 388, Rose Bengal B (Edible Red No. 5), Acid Rhodamine G, C.I. I. It is preferable to use Acid Violet 9.
Among these, in terms of heat resistance and light resistance, C.I. I. Acid Red 87, C.I. I. Acid Red 92, C.I. I. Acid Red 388 or rhodamine acid dye C.I. I. Acid Red 52 (Acid Rhodamine), C.I. I. Acid Red 289, Acid Rhodamine G, C.I. I. It is more preferable to use Acid Violet 9.
Among these, in particular, C.I., which is a rhodamine acid dye, is excellent in color developability, heat resistance and light resistance. I. Acid Red 52, C.I. I. Most preferably, Acid Red 289 is used.

  The xanthene dye [A2] used in the present invention is preferably a salt-forming compound of a xanthene-based acid dye and a nitrogen-containing compound, and is a xanthene-based acid salt formed using a quaternary ammonium salt as the nitrogen-containing compound. Since it is particularly preferable to use a dye salt-forming compound or a xanthene-based acidic dye by sulfonamidation, these two forms will be described in detail below.

(Salt-forming compounds of xanthene acid dyes)
In the present invention, the xanthene-based acidic dye is formed by chlorination using a quaternary ammonium salt compound, a tertiary amine compound, a secondary amine compound, a primary amine compound, etc., and a resin component having these functional groups. Since it can provide high heat resistance, light resistance, and solvent resistance, it is preferable to use this salt-forming compound.

  Primary amine compounds include methylamine, ethylamine, propylamine, isopropylamine, butylamine, amylamine, hexylamine, heptylamine, octylamine, nonylamine, decylamine, undecylamine, dodecylamine (laurylamine), tridodecylamine, tetra Examples include aliphatic unsaturated primary amines such as decylamine (myristylamine), pentadecylamine, cetylamine, stearylamine, oleylamine, cocoalkylamine, beef tallow alkylamine, cured tallow alkylamine, allylamine, aniline, and benzylamine. .

  Secondary amine compounds include aliphatic unsaturated secondary amines such as dimethylamine, diethylamine, dipropylamine, diisopropylamine, dibutylamine, diamylamine, diallylamine, methylaniline, ethylaniline, dibenzylamine, diphenylamine, dicocoalkyl. Amine, di-cured tallow alkylamine, distearylamine, etc.

  Examples of the tertiary amine compound include trimethylamine, triethylamine, tripropylamine, tributylamine, triamylamine, dimethylaniline, diethylaniline, tribenzylamine and the like.

-Salt-forming compound composed of xanthene-based acid dye and quaternary ammonium salt compound The xanthene-based dye [A2] used in the present invention should be used as a salt-forming compound composed of the aforementioned xanthene-based acid dye and quaternary ammonium salt compound. Is most preferable from the viewpoints of heat resistance, light resistance, and solvent resistance.

-Quaternary ammonium salt compound A quaternary ammonium salt compound has an amino group, and the cation part becomes a counter of a xanthene acid dye.

  A preferred form of the quaternary ammonium salt compound that is a counter component of the salt-forming compound is colorless or white. Here, colorless or white means a so-called transparent state, and is defined as a state in which the transmittance is 95% or more, preferably 98% or more in the entire wavelength region of 400 to 700 nm in the visible light region. Is. That is, it is necessary not to inhibit color development of the dye component and to cause no color change.

The molecular weight of the cation moiety serving as a counter for the quaternary ammonium salt compound is preferably in the range of 190 to 900. Here, the cation moiety corresponds to the (NR ₁ R ₂ R ₃ R ₄ ) ⁺ moiety in the following general formula (2). When the molecular weight is smaller than 190, light resistance and heat resistance are lowered, and the solubility in a solvent may be further lowered. On the other hand, when the molecular weight is larger than 900, the ratio of the coloring component in the molecule is lowered, so that the color developability is lowered and the lightness is also lowered. More preferably, the molecular weight of the cation moiety is in the range of 240 to 850, and particularly preferably in the range of 350 to 800.
Here, the molecular weight was calculated based on the structural formula. The atomic weight of C was 12, the atomic weight of H was 1, and the atomic weight of N was 14.

  Moreover, it is preferable to use the compound represented by following General formula (3) as a quaternary ammonium salt compound.

[一般式（３）中、Ｒ₁〜Ｒ₄は、それぞれ独立に、炭素数１〜２０のアルキル基またはベンジル基を示し、Ｒ₁、Ｒ₂、Ｒ₃、又はＲ₄の少なくとも２つ以上が、Ｃの数が５〜２０個である。Ｙ^-は無機または有機のアニオンを表す。]

[In General Formula (3), R _{1 to} R ₄ each independently represents an alkyl group having 1 to 20 carbon atoms or a benzyl group, and at least two of R ₁ , R ₂ , R ₃ , or R ₄ However, the number of C is 5-20. Y ^- is representative of an inorganic or organic anion. ]

The solubility with respect to a solvent becomes favorable because the number of C of the side chain of at least 2 of R < ₁ > -R < ₄ > shall be 5-20. When R _{1 to} R ₄ have 3 or more alkyl groups having a C number smaller than 5, the solubility in a solvent is deteriorated, and coating film foreign matter is likely to be generated. Further, if an alkyl group having a C number exceeding 20 is present in the side chain, the color forming property of the salt-forming compound may be impaired.

The Y ⁻ component constituting the anion of the quaternary ammonium salt compound may be an inorganic or organic anion, but is preferably a halogen, usually chlorine.

Specific examples of such quaternary ammonium salt compounds include tetramethylammonium chloride (with a molecular weight of the cation moiety of 74), tetraethylammonium chloride (with a molecular weight of the cation moiety of 122), and monostearyltrimethylammonium chloride (with a molecular weight of the cation moiety). 312), distearyldimethylammonium chloride (cation part molecular weight 550), tristearyl monomethylammonium chloride (cation part molecular weight 788), cetyltrimethylammonium chloride (cation part molecular weight 284), trioctylmethylammonium chloride ( The molecular weight of the cation moiety is 368), dioctyldimethylammonium chloride (the molecular weight of the cation moiety is 270), monolauryltrimethyla Monium chloride (cation part molecular weight 228), dilauryldimethylammonium chloride (cation part molecular weight 382), trilaurylmethylammonium chloride (cation part molecular weight 536), triamylbenzylammonium chloride (cation part molecular weight 318), trihexylbenzylammonium chloride (cation part molecular weight 360), trioctylbenzylammonium chloride (cation part molecular weight 444), trilaurylbenzylammonium chloride (cation part molecular weight 612), benzyldimethylstearylammonium chloride (Molecular weight of the cation moiety is 388) and benzyldimethyloctyl ammonium chloride (molecular weight of the cation moiety is 248) , Or dialkyl (alkyl C ₁₄ -C ₁₈₎ dimethyl ammonium chloride (hydrogenated tallow) (molecular weight of the cationic moiety is from 438 to 550) is preferably used and the like.

As products, Cotamin 24P, Cotamin 86P Conch, Cotamin 60W, Cotamin 86W, Cotamin D86P, Sanizole C, Sanizole B-50, etc. manufactured by Kao Corporation, Lion Corporation's Arcade 210-80E, 2C-75, 2HT-75, 2HT flakes, 2O-75I, 2HP-75 or 2HP flakes and the like, among others QUARTAMIN D86P (distearyldimethylammonium chloride), or Arquad 2HT-75 (di (alkyl C ₁₄ -C ₁₈₎ dimethyl ammonium chloride) Etc. are preferable.

The quaternary ammonium salt compound may be in the form of a resin having a cationic group, particularly an amino group or an ammonium group in the side chain, and capable of forming a quaternary ammonium salt structure by reacting and salting with a xanthene acid dye. . (See Reference 1)
(Reference 1) Japanese Patent Application No. 2011-150752

Resin having a cationic group in the side chain The resin having a cationic group in the side chain is an alkaline resin containing a structural unit represented by the following general formula (4), and the cationic group in the general formula (4) However, a salt-forming compound can be obtained by forming a salt with the anionic group of the xanthene acid dye.

［一般式（４）中、Ｒ₅は水素原子、または置換もしくは無置換のアルキル基を表す。Ｒ₆〜Ｒ₈は、それぞれ独立に、水素原子、置換されていてもよいアルキル基、置換されていてもよいアルケニル基、または置換されていてもよいアリール基を表し、Ｒ₆〜Ｒ₈のうち２つが互いに結合して環を形成しても良い。Ｑはアルキレン基、アリーレン基、−ＣＯＮＨ−Ｒ₉−、−ＣＯＯ−Ｒ₉−を表し、Ｒ₉はアルキレン基を表す。Ｙ^-は無機または有機のアニオンを表す。］

[In General Formula (4), R ₅ represents a hydrogen atom or a substituted or unsubstituted alkyl group. R _{6 to} R ₈ each independently represents a hydrogen atom, an optionally substituted alkyl group, an optionally substituted alkenyl group, or an optionally substituted aryl group, and R _{6 to} R ₈ Two of them may be bonded to each other to form a ring. Q represents an alkylene group, an arylene group, —CONH—R ₉ —, —COO—R ₉ —, and R ₉ represents an alkylene group. Y ^- is representative of an inorganic or organic anion. ]

-Manufacturing method of salt-forming compound The salt-forming compound of a xanthene acid dye and a quaternary ammonium salt compound can be manufactured by a conventionally known method. A specific method is disclosed in Japanese Patent Laid-Open No. 11-72969.
For example, after the xanthene acid dye is dissolved in water, the quaternary ammonium salt compound is added and the chlorination treatment may be performed while stirring. Here, the sulfonic acid group (—SO ₃ H), sodium sulfonate group (—SO ₃ Na) part in the xanthene acid dye and the ammonium group (NH ₄ ⁺ ) part of the quaternary ammonium salt compound are combined. A salt compound is obtained. In addition, instead of water, methanol and ethanol are also solvents that can be used for the chlorination.

  The salt-forming compound used in the present invention is prepared by stirring or vibrating an aqueous solution in which a resin having a cationic group in the side chain represented by the general formula (4) and a xanthene-based acidic dye are dissolved, or in general. It can be easily obtained by mixing an aqueous solution of a resin having a cationic group in the side chain represented by the formula (4) and an aqueous solution of a xanthene acid dye under stirring or vibration. In the aqueous solution, the ammonium group of the resin and the anionic group of the xanthene acid dye are ionized, and these are ionically bonded, and the ion-bonded portion becomes water-insoluble and precipitates. On the contrary, the salt composed of the counter anion of the resin and the counter cation of the xanthene-based acidic dye is water-soluble and can be removed by washing with water. The resin having a cationic group in the side chain to be used and the xanthene acid dye may be used alone or in a plurality of types having different structures.

Examples of the salt-forming compound include C.I. I. Acid Red 289 and C.I. I. By using a salt-forming compound of Acid Red 52 and a quaternary ammonium salt compound having a molecular weight of the counter cation moiety of 350 to 800, it has excellent solvent solubility and is more heat resistant when used in combination with a pigment described later. Excellent in light resistance, light resistance and solvent resistance. In addition, it is presumed that the salt formation compound that is favorable when used in combination with the pigment is adsorbed on the pigment while being dissolved and dispersed in the solvent. At this time, the primary particle diameter of the pigment is preferably 20 to 100 nm.
Although the coloring composition of this invention is mentioned later, the form of the blue coloring composition used together with a blue pigment and the red coloring composition used together with a red pigment is preferable.

(Sulphonic acid amide compound of xanthene acid dye)
The xanthene-based acid dye in the present invention is preferably sulfonated to give a sulfonic acid amide compound because high heat resistance, light resistance, and solvent resistance can be imparted.
A sulfonic acid amide compound of a xanthene acid dye that can be preferably used in the xanthene dye [A2] of the present invention is obtained by chlorinating a xanthene acid dye having —SO ₃ H and —SO ₃ Na by a conventional method, SO ₃ H can be made —SO ₂ Cl, and this compound can be produced by reacting with an amine having an —NH ₂ group.

Specific examples of amine compounds that can be preferably used in sulfonamidation include 2-ethylhexylamine, dodecylamine, 3-decyloxypropylamine, 3- (2-ethylhexyloxy) propylamine, and 3-ethoxypropyl. It is preferable to use amine, cyclohexylamine or the like.
For example, C.I. I. In the case of obtaining a sulfonic acid amide compound obtained by modifying Acid Red 289 with 3- (2-ethylhexyloxy) propylamine, C.I. I. Acid Red 289 was converted to a sulfonyl chloride and reacted with a theoretical equivalent of 3- (2-ethylhexyloxy) propylamine in dioxane to give C.I. I. What is necessary is just to obtain the sulfonic acid amide compound of Acid Red 289.
In addition, C.I. I. In the case of obtaining a sulfonic acid amide compound obtained by modifying Acid Red 52 with 3- (2-ethylhexyloxy) propylamine, C.I. I. Acid Red 52 was converted to a sulfonyl chloride and reacted with a theoretical equivalent of 3- (2-ethylhexyloxy) propylamine in dioxane to give C.I. I. What is necessary is just to obtain the sulfonic acid amide compound of Acid Red 52.

《Other colorants》
As the colorant [A] of the coloring composition for a color filter of the present invention, a pigment can be used in combination.

  Examples of blue pigments that can be used include C.I. I. Pigment Blue 1, 1: 2, 9, 14, 15, 15: 1, 15: 2, 15: 3, 15: 4, 15: 6, 16, 17, 19, 25, 27, 28, 29, 33, 35, 36, 56, 56: 1, 60, 61, 61: 1, 62, 63, 66, 67, 68, 71, 72, 73, 74, 75, 76, 78, 79 and the like. Among these, from the viewpoint of obtaining a high contrast ratio and high brightness, C.I. I. Pigment Blue 15, 15: 1, 15: 2, 15: 3, 15: 4, or 15: 6, and more preferably C.I. I. Pigment Blue 15: 6.

  In particular, when a colored composition is used for a blue pixel, it is possible to have a high spectral spectrum transmittance in the vicinity of 425 to 500 nm having a characteristic peak of many backlights by using a blue pigment in combination. Therefore, it is preferable because a higher brightness can be obtained as a blue filter segment than a colorant that is a combination of a conventional blue pigment and other pigments.

  Examples of the green pigment include C.I. I. Pigment green 1, 2, 4, 7, 8, 10, 13, 14, 15, 17, 18, 19, 26, 36, 45, 48, 50, 51, 54, 55 or 58. Among these, from the viewpoint of obtaining a high contrast ratio and high brightness, C.I. I. Pigment Green 7, 36 or 58.

  Examples of yellow pigments include C.I. I. Pigment Yellow 1, 1: 1, 2, 3, 4, 5, 6, 9, 10, 12, 13, 14, 16, 17, 24, 31, 32, 34, 35, 35: 1, 36, 36: 1, 37, 37: 1, 40, 41, 42, 43, 48, 53, 55, 61, 62, 62: 1, 63, 65, 73, 74, 75, 81, 83, 87, 93, 94, 95, 97, 100, 101, 104, 105, 108, 109, 110, 111, 116, 117, 119, 120, 126, 127, 127: 1, 128, 129, 133, 134, 136, 138, 139, 142, 147, 148, 150, 151, 153, 154, 155, 157, 158, 159, 160, 161, 162, 163, 164, 165, 166, 167, 168, 169, 170, 172, 17 174, 175, 176, 180, 181, 182, 183, 184, 185, 188, 189, 190, 191, 191: 1, 192, 193, 194, 195, 196, 197, 198, 199, 200, 202 , 203, 204, 205, 206, 207, 208, and the like. Among these, from the viewpoint of obtaining a high contrast ratio and high brightness, C.I. I. Pigment Yellow 83, 117, 129, 138, 139, 150, 154, 155, 180, or 185, more preferably C.I. I. Pigment yellow 83, 138, 139, 150, or 180.

  Examples of purple pigments include C.I. I. Pigment Violet 1, 1: 1, 2, 2: 2, 3, 3: 1, 3: 3, 5, 5: 1, 14, 15, 16, 19, 23, 25, 27, 29, 31, 32, 37, 39, 42, 44, 47, 49, 50 and the like. Among these, from the viewpoint of obtaining a high contrast ratio and high brightness, C.I. I. Pigment violet 19 or 23, more preferably C.I. I. Pigment Violet 23.

Examples of red pigments include C.I. I. Pigment Red 1, 2, 3, 4, 5, 6, 7, 8, 9, 12, 14, 15, 16, 17, 21, 22, 23, 31, 32, 37, 38, 41, 47, 48, 48: 1, 48: 2, 48: 3, 48: 4, 49, 49: 1, 49: 2, 50: 1, 52: 1, 52: 2, 53, 53: 1, 53: 2, 53: 3, 57, 57: 1, 57: 2, 58: 4, 60, 63, 63: 1, 63: 2, 64, 64: 1, 68, 69, 81, 81: 1, 81: 2, 81: 3, 81: 4, 83, 88, 90: 1, 101, 101: 1, 104, 108, 108: 1, 109, 112, 113, 114, 122, 123, 144, 146, 147, 149, 151 166, 168, 169, 170, 172, 173, 174, 175, 176, 177, 178, 17 9, 181, 184, 185, 187, 188, 190, 193, 194, 200, 202, 206, 207, 208, 209, 210, 214, 216, 220, 221, 224, 230, 231, 232, 233, 235, 236, 237, 238, 239, 242, 243, 245, 247, 249, 250, 251, 253, 254, 255, 256, 257, 258, 259, 260, 262, 263, 264, 265, 266, 267, 268, 269, 270, 271, 272, 273, 274, 275, 276, and the like.
Examples of orange pigments that work in the same way as red pigments include C.I. I. Orange pigments such as CI Pigment Orange 36, 38, 43, 51, 55, 59, 61 can be used. Among these, from the viewpoint of obtaining a high contrast ratio and high brightness, C.I. I. Pigment red 254, C.I. I. It is particularly preferable to use Pigment Red 177.

<Miniaturization of pigment>
The pigment used in the present invention can be refined by a salt milling process or the like. The primary particle diameter of the pigment is preferably 20 nm or more because of good dispersion in the pigment carrier. Moreover, since it can form a filter segment with high contrast ratio, it is preferable that it is 100 nm or less. A particularly preferable range is a range of 25 to 85 nm. In addition, the primary particle diameter of a pigment has the method of measuring the magnitude | size of a primary particle directly from the electron micrograph by TEM (transmission electron microscope) of a pigment, for example. Specifically, for example, the short axis diameter and the long axis diameter of the primary particle of each pigment are measured in nm units, and the average is the primary particle diameter of the pigment particle. There is a method of calculating the number average particle diameter by obtaining the volume of the particles, performing this operation for 100 pigment particles, and calculating based on the respective particle diameters and volumes.

  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 serves as a crushing aid, and the pigment is crushed using the high hardness of the inorganic salt during salt milling. By optimizing the conditions for salt milling the pigment, it is possible to obtain a pigment having a sharp particle size distribution with a very fine primary particle diameter and a wide distribution range.

  As the water-soluble inorganic salt, 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 weight, and most preferably 300 to 1000 parts by weight with respect to 100 parts by weight of the pigment, 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 100 parts by weight of the pigment.

  When the salt is milled, 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 the resin used is preferably in the range of 5 to 200 parts by weight with respect to 100 parts by weight of the pigment.

  When preparing a pigment dispersion, add pigment derivatives to prevent aggregation of the pigment, maintain a finely dispersed state of the pigment, and produce a color filter with high brightness and high contrast ratio and high color purity. Is preferred. The content of the pigment derivative is preferably 0.5 parts by weight or more, more preferably 1 part by weight or more, and most preferably 3 parts by weight or more with respect to 100 parts by weight of the pigment. Further, from the viewpoint of heat resistance and light resistance, the amount is preferably 40 parts by weight or less, and most preferably 35 parts by weight or less with respect to 100 parts by weight of the pigment.

  A pigment derivative is a compound in which a basic or acidic substituent is introduced into an organic dye. Organic dyes include light yellow aromatic polycyclic compounds that are not generally called dyes, such as naphthalene, anthraquinone, and acridone. Examples of the pigment derivative include JP-A-63-305173, JP-B-57-15620, JP-B-59-40172, JP-B-63-17102, JP-B-5-9469, JP-A-9-9. 176511 gazette etc. can be used, and these can be used individually or in mixture of 2 or more types.

  The coloring composition for a color filter of the present invention can be added with a resin-type dispersant that is excellent in pigment dispersibility and has a large effect of preventing reaggregation of the pigment after dispersion. The resin-type dispersant can be used in an amount of preferably 0.1 to 40 parts by weight, more preferably 0.1 to 30 parts by weight with respect to 100 parts by weight of the pigment.

  The resin-type dispersant has an acidic group or a basic group because it adsorbs to the surface of the pigment using an acidic group or a basic group as an anchor, and the rebound effect of the polymer acts effectively to express dispersion stability. A polymer is preferred. The acidic group is preferably a sulfone group from the viewpoint of excellent adsorption characteristics, and the basic group is preferably an amino group from the viewpoint of excellent adsorption characteristics. Also, the combined use of a pigment derivative having an acidic group and a resin type dispersant having a basic group, or a combined use of a pigment derivative having a basic group and a resin type dispersant having an acidic group has good compatibility with the resin. Therefore, it is preferable.

  As a resin type dispersant having an acidic group or a basic group, a comb polymer having a structure in which a branch polymer part is graft-bonded to a trunk polymer part having an acidic group or a basic group has an excellent steric repulsion effect of the branch polymer part. It is preferable because it is more soluble in organic solvents. Furthermore, a comb polymer having a molecular structure in which two or more branch polymers are grafted to one molecule of the trunk polymer is more preferable for the above reason.

  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 -SOLPERSE-3000, 9000, 13000, 13240, 13650, 13940, 160 manufactured by Nippon Lubrizol Corporation, such as P104, P104S, 220S, 6919, or Lactimon, Lactimon-WS or Bykumen, etc. 0, 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, 7 54,1101,120,150,1501,1502,1503, etc., Ajinomoto Fine-Techno Co., Ltd. of AJISPER PA111, PB711, PB821, PB822, PB824, and the like.

  The coloring composition for a color filter of the present invention may be used in combination with a dye other than a xanthene dye as another colorant.

<Binder resin>
The binder resin contained in the colored composition of the present invention is one that disperses or dyes or penetrates a colorant, and includes conventionally known thermoplastic resins and thermosetting resins. The binder resin is preferably a resin having a spectral transmittance of preferably 80% or more, more preferably 95% or more in the entire wavelength region of 400 to 700 nm in the visible light region.

  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.

Moreover, when using with the form of an alkali image development type colored resist material, it is preferable to use the alkali-soluble resin which copolymerized the acidic group containing ethylenically unsaturated monomer. In order to further improve the photosensitivity, an active energy ray-curable resin having an ethylenically unsaturated double bond can also be used.
In particular, by using an active energy ray-curable resin having an ethylenically unsaturated double bond in the side chain as an alkali development type colored resist material, the resin is three-dimensionally crosslinked when exposed to active energy rays to form a coating film. As a result, the colorant is fixed, heat resistance is improved, and fading (lightness reduction) due to heat of the colorant can be suppressed. In addition, there is also an effect of suppressing aggregation and precipitation of the colorant component in the development process.

  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 an ethylenically unsaturated active double bond include polymers having reactive substituents such as hydroxy groups, carboxyl groups, amino groups, and reactive groups such as isocyanate groups, aldehyde groups, and epoxy groups. 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 substituent or cinnamic acid is used. Further, a polymer containing an acid anhydride such as a styrene-maleic anhydride copolymer or an α-olefin-maleic anhydride copolymer is 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 preferred as the color filter coloring composition.

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, styrene, styrene such as α-methylstyrene, vinyl ethers such as ethyl vinyl ether, n-propyl vinyl ether, isopropyl vinyl ether, n-butyl vinyl ether, or isobutyl vinyl ether, fatty acid vinyl 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 colorant 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 as a coloring composition for a color filter, a colorant adsorbing group and a carboxyl group that acts as an alkali-soluble group during development, an aliphatic group that acts as an affinity group for the colorant carrier and solvent, and an aromatic group The balance of groups is important for the dispersibility, penetrability, developability, and durability of the colorant, 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 developing solution is poor and it is difficult to form a fine pattern. When it exceeds 300 mgKOH / g, a fine pattern does not remain by development.

  The binder resin is preferably used in an amount of 20 to 500 parts by weight with respect to 100 parts by weight of the colorant. If it is less than 20 parts by weight, the film formability and various resistances are insufficient, and if it is more than 500 parts by weight, the concentration of the colorant becomes low and color characteristics cannot be expressed.

<Organic solvent>
In the coloring composition of the present invention, the colorant is sufficiently dispersed and permeated in the colorant carrier, and is applied on a substrate such as a glass substrate so that the dry film thickness is 0.2 to 5 μm. An organic solvent is 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.
These solvents can be used alone or in admixture of two or more at any ratio as required.

  Among them, the dispersibility of the coloring agent, the penetrability, and the coating property of the coloring composition are good, so that alkyl lactates such as ethyl lactate, propylene glycol monomethyl ether acetate, propylene glycol monoethyl ether acetate, ethylene glycol monomethyl ether acetate It is preferable to use glycol acetates such as ethylene glycol monoethyl ether acetate, alcohols such as benzyl alcohol and diacetone alcohol, and ketones such as cyclohexanone.

  In addition, the organic solvent can be used in an amount of 500 to 4000 parts by weight with respect to 100 parts by weight of the colorant because the colored composition can be adjusted to an appropriate viscosity to form a filter segment having a desired uniform film thickness. Is preferred.

<Photopolymerizable monomer>
Photopolymerizable monomers that may be added to the colored 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 colorant, and more preferably 10 to 300 parts by weight from the viewpoint of photocurability and developability. .

<Photopolymerization initiator>
In the colored composition of the present invention, a photopolymerization initiator is added to form a filter segment by photolithography by curing the composition by ultraviolet irradiation, and a solvent development type or alkali development type photosensitive coloring composition is added. It can be prepared in the form of

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 colorant, and more preferably 3 to 150 parts by weight from the viewpoint of photocurability and developability.

<Sensitizer>
Furthermore, the 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, tetraphyrin derivatives, annulene derivatives, spiropyran derivatives, spirooxazine Derivatives, thiospiropyran derivatives, metal arene complexes, organoruthenium complexes, or Michler's ketone derivatives, biimidazole derivatives, α-acyloxy esters, acylphosphine oxides, methylphenylglyoxylate, benzyl, 9,10-phenanthrenequinone, Camphorquinone, ethylanthraquinone, 4,4′-diethylisophthalophenone, 3,3 ′, or 4,4′-tetra (t-butylperoxyca Rubonyl) benzophenone, 4,4′-diethylaminobenzophenone and the like.
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 colored composition, and 5 to 50 parts by weight from the viewpoint of photocurability and developability. It is more preferable that

<Multifunctional thiol>
The coloring composition for a color filter of the present invention can contain a polyfunctional thiol that functions as a chain transfer agent.
The polyfunctional thiol may be a compound having two or more thiol groups. For example, hexanedithiol, decanedithiol, 1,4-butanediol bisthiopropionate, 1,4-butanediol bisthioglycolate, ethylene Glycol bisthioglycolate, ethylene glycol bisthiopropionate, trimethylolpropane tristhioglycolate, trimethylolpropane tristhiopropionate, trimethylolpropane tris (3-mercaptobutyrate), pentaerythritol tetrakisthioglycolate, Pentaerythritol tetrakisthiopropionate, trimercaptopropionic acid tris (2-hydroxyethyl) isocyanurate, 1,4-dimethylmercaptobenzene,
2,4,6-trimercapto-s-triazine, 2- (N, N-dibutylamino) -4,6-dimercapto-s-triazine and the like. These polyfunctional thiols can be used singly or in combination of two or more in any ratio as necessary.

  The content of the polyfunctional thiol is preferably 0.1 to 30% by weight, more preferably 1 to 20% by weight based on the weight (100% by weight) of the total solid content of the color filter coloring composition. . If the content of the polyfunctional thiol is less than 0.1% by weight, the effect of adding the polyfunctional thiol is insufficient, and if it exceeds 30% by weight, the sensitivity is too high and the resolution is lowered.

<Antioxidant>
The coloring composition for a color filter of the present invention can contain an antioxidant. Antioxidants are used to prevent the photopolymerization initiators and thermosetting compounds contained in the color filter coloring composition from oxidizing and yellowing due to thermal processes during thermal curing and ITO annealing. Can be high. Therefore, by including an antioxidant, yellowing due to oxidation during the heating step can be prevented, and a high coating film transmittance can be obtained.

  The “antioxidant” in the present invention may be a compound having an ultraviolet absorbing function, a radical scavenging function, or a peroxide decomposing function. Specifically, as an antioxidant, a hindered phenol type, a hindered amine type are used. , Phosphorus-based, sulfur-based, benzotriazole-based, benzophenone-based, hydroxylamine-based, salicylate-based, and triazine-based compounds, and known ultraviolet absorbers, antioxidants, and the like can be used.

  Among these antioxidants, a hindered phenol antioxidant, a hindered amine antioxidant, a phosphorus antioxidant, or a sulfur antioxidant is preferable from the viewpoint of achieving both transmittance and sensitivity of the coating film. Agents. More preferably, they are hindered phenolic antioxidants, hindered amine antioxidants, or phosphorus antioxidants.

  These antioxidants can be used singly or in combination of two or more at any ratio as required.

  When the content of the antioxidant is 0.5 to 5.0% by weight based on the solid content weight of the color filter coloring composition (100% by weight), brightness and sensitivity are more preferable.

<Amine compound>
Moreover, the coloring composition of this invention can be made to contain the amine compound which has a function which reduces the 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 colored 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 coloring composition (100% by weight).

  Particularly preferred as a leveling agent is a kind of so-called surfactant having a hydrophobic group and a hydrophilic group in the molecule, having a hydrophilic group but low solubility in water, and when added to a coloring composition, It has the characteristics of low surface tension reduction ability, and it is useful to have good wettability to the glass plate despite its low surface tension reduction ability. Those that can sufficiently suppress the chargeability 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 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 coloring composition of the present invention may 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 coloring composition.

<Method for producing colored composition>
The coloring composition of the present invention comprises a colorant [A] in a colorant carrier such as a binder resin and / or a solvent, preferably together with a dispersion aid, 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 (colorant dispersion). At this time, the salt-forming compound [A1], the xanthene dye [A2], and other colorants may be simultaneously dispersed in the colorant carrier, or those separately dispersed in the colorant carrier may be mixed. good. In addition, when the colorant has high solubility, specifically, it is highly soluble in the solvent to be used, and if it is dissolved by stirring and no foreign matter is confirmed, it is necessary to manufacture by finely dispersing as described above. There is no.

  Moreover, when using as a photosensitive coloring composition (resist material) for color filters, it can prepare as a solvent developing type or an alkali developing type coloring composition. The solvent development type or alkali development type coloring composition includes the colorant dispersion, a photopolymerizable monomer and / or a photopolymerization initiator, and, if necessary, a solvent, other pigment dispersants, and additives. Etc. can be mixed and adjusted. The photopolymerization initiator may be added at the stage of preparing the colored composition, or may be added later to the prepared colored composition.

(Dispersing aid)
When dispersing the colorant in the colorant carrier, a dispersion aid such as a pigment derivative, a resin-type dispersant, or a surfactant may be appropriately contained. Since the dispersion aid has a large effect of preventing reaggregation of the colorant after dispersion, the color composition obtained by dispersing the colorant in the colorant carrier using the dispersion aid has lightness and viscosity stability. Become good.

  Examples of the dye derivative include a compound obtained by introducing a basic substituent, an acidic substituent, or a phthalimidomethyl group which may have a substituent into an organic pigment, anthraquinone, acridone, or triazine. 63-305173, JP-B-57-15620, JP-B-59-40172, JP-B-63-17102, JP-B-5-9469, JP-A-2001-335717, JP-A-2003 128669, JP-A-2004-091497, JP-A-2007-156395, JP-A-2008-094773, JP-A-2008-094986, JP-A-2008-095007, JP-A-2008-195916 Gazettes, Japanese Patent No. 4585781 etc. can be used. These may be used alone or in combination of two or more. When a dye derivative is used, those having a quinophthalone skeleton and an azo skeleton are preferable from the viewpoint of lightness.

  The content of the pigment derivative is preferably 0.5 parts by weight or more, more preferably 1 part by weight or more, and most preferably 3 parts by weight or more with respect to 100 parts by weight of the colorant from the viewpoint of improving dispersibility. Further, from the viewpoint of heat resistance and light resistance, it is preferably 40 parts by weight or less, more preferably 35 parts by weight or less.

  The resin-type dispersant has a colorant-affinity part having the property of adsorbing to the colorant and a part compatible with the colorant carrier, and adsorbs to the colorant to disperse the colorant to the colorant carrier. It works to stabilize. 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 addition compound, phosphate ester-based and the like are used, they can be used alone or in admixture of two or more, not necessarily limited thereto.

  Commercially available resin-type dispersants include Disperbyk-101, 103, 107, 108, 110, 111, 116, 130, 140, 154, 161, 162, 163, 164, 165, 166, 167 manufactured by Big Chemie Japan. 168, 170, 171, 174, 180, 181, 182, 183, 184, 185, 190, 2000, 2001, 2009, 2010, 2020, 2025, 2050, 2070, 2095, 2150, 2155, 2163, 2164 or Anti -Terra-U, 203, 204, or BYK-P104, P104S, 220S, 6919, 21116, 21324, 21407, 21715 or Lactimon, Lactimon-WS or Bykumen, etc., Japan Lubrizol SOLSPERSE-3000, 9000, 13000, 13240, 13650, 13940, 16000, 17000, 18000, 20000, 21000, 24000, 26000, 27000, 28000, 31845, 32000, 32500, 32550, 33500, 32600, 34750, 35100, 36600, 38500, 41000, 41090, 53095, 55000, 56000, 76500, etc., EFKA-46, 47, 48, 452, 4008, 4009, 4010, 4015, 4020, 4047, 4050, 4055, 4060, manufactured by Ciba Japan , 4080, 4400, 4401, 4402, 4403, 4406, 4408, 4300, 4310, 4320, 4330, 4340, 45 451, 453, 4540, 4550, 4560, 4800, 5010, 5065, 5066, 5070, 7500, 7554, 1101, 120, 150, 1501, 1502, 1503, etc., Ajimoto Fine Techno Co., Ltd. PB821, PB822, PB824, etc. are mentioned.

  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.

  When a resin-type dispersant and a surfactant are added, the amount is preferably 0.1 to 55 parts by weight, more preferably 0.1 to 45 parts by weight with respect to 100 parts by weight of the colorant. When the blending amount of the resin-type dispersant and the surfactant is less than 0.1 parts by weight, it is difficult to obtain the added effect. When the content is more than 55 parts by weight, the dispersion is affected by an excessive dispersant. May affect.

<Removal of coarse particles>
The colored composition of the present invention is prepared by means of centrifugal separation, filtration with a sintered filter or a membrane filter, and the like. Coarse particles of 5 μm or more, preferably 1 μm or more, more preferably 0.5 μm or more It is preferable to remove the mixed dust. Thus, it is preferable that a coloring composition does 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 is provided with a filter segment and / or a black matrix formed on the base material from the coloring composition for a color filter of the present invention. , Red, green and blue filter segments. The filter segment may further include a magenta filter segment, a cyan filter segment, and a yellow filter segment.

  As the substrate, glass plates such as soda lime glass, low alkali borosilicate glass and non-alkali aluminoborosilicate glass, which are transparent substrates, and resin plates such as polycarbonate, polymethyl methacrylate, and polyethylene terephthalate can be used. . In addition, a transparent electrode made of indium oxide, tin oxide, or the like may be formed on the surface of the glass plate or the resin plate in order to drive the liquid crystal after forming the panel.

  If the black matrix is formed in advance before forming the filter segment on the substrate, the contrast of the liquid crystal display panel can be further increased. As the black matrix, chromium, a 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. However, the present invention is not limited thereto, and the coloring composition for color filters of the present invention A black matrix formed from is preferable. A thin film transistor (TFT) may be formed in advance on the transparent substrate or the reflective substrate, and then a filter segment may be formed. By forming the filter segment and / or the black matrix on the TFT substrate, the aperture ratio of the liquid crystal display panel can be increased and the luminance can be improved.

  The dry film thickness of the filter segment and the black matrix is preferably 0.2 to 10 μm, more preferably 0.2 to 5 μm. When drying the coating film, a vacuum dryer, a convection oven, an IR oven, a hot plate, or the like may be used.

  Formation of each color filter segment and black matrix by photolithography is performed by the following method. That is, the color composition for color filter prepared as a color composition for solvent development type or alkali development type color filter is dried on a transparent substrate by a coating method such as spray coating, spin coating, slit coating or roll coating. It is applied so that the film thickness is 0.2 to 10 μm. 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.

  Thereafter, the filter segment and the black matrix can be formed by immersing in a solvent or an alkali developer or spraying the developer by spraying or the like to remove uncured portions and forming a desired pattern. Furthermore, in order to accelerate the polymerization of the filter segment and the black matrix formed by development, heating can be performed as necessary. According to the photolithography method, it is possible to form a filter segment and a black matrix with higher accuracy than the printing method.

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.
As a development processing method, a shower development method, a spray development method, a dip (immersion) development method, a paddle (liquid accumulation) development method, or the like can be applied.
In order to increase UV exposure sensitivity, after applying and drying the above color filter coloring composition, a water-soluble or alkali-soluble resin such as polyvinyl alcohol or water-soluble acrylic resin is applied and dried to prevent polymerization inhibition due to oxygen. Ultraviolet exposure can also be performed after forming a film.

  An overcoat film, a columnar spacer, a transparent conductive film, a liquid crystal alignment film, and the like are formed on the color filter as necessary.

  The color filter is bonded to the counter substrate using a sealant, and after injecting liquid crystal from the injection port provided in the seal part, the injection port is sealed, and if necessary, a polarizing film or a retardation film is placed outside the substrate. A liquid crystal display panel is manufactured by bonding.

  Such liquid crystal display panels include twisted nematic (TN), super twisted nematic (STN), in-plane switching (IPS), vertical alignment (VA), and optically convented bend (OCB). It can be used in a liquid crystal display mode in which colorization is performed using a color filter such as the above.

  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 weight” and “% by weight”, respectively.

  Moreover, the average primary particle diameter of a pigment, the weight average molecular weight (Mw) of resin, and the measuring method of the ammonium salt value of resin which has a cationic group in a side chain 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 (TEM) electron microscope. 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 was measured in terms of polystyrene measured using TSKgel column (manufactured by Tosoh Corporation) and GPC (manufactured by Tosoh Corporation, HLC-8120GPC) equipped with an RI detector using THF as a developing solvent. It is a weight average molecular weight (Mw).

(Ammonium salt value of a resin having a cationic group in the side chain)
The ammonium salt value of the resin having a cationic group in the side chain is a value converted to the equivalent of potassium hydroxide after being obtained by titration with a 0.1N silver nitrate aqueous solution using a 5% potassium chromate aqueous solution as an indicator. Represents the ammonium salt value of the solid content.

  Subsequently, a method for producing a binder resin solution used in Examples and Comparative Examples, a method for producing a resin for salt-forming dyes, a method for producing a triarylmethane-based salt-forming compound, a method for producing a triarylmethane-based colorant-containing solution, A method for producing a xanthene dye, a method for producing a xanthene dye-containing solution, a method for producing a fine pigment, a method for preparing a pigment dispersant solution, and a method for producing a pigment dispersion will be described.

<Method for producing binder resin solution>
(Acrylic resin solution (B-1))
A separable four-necked flask equipped with a thermometer, a cooling pipe, a nitrogen gas introduction pipe, a dropping pipe and a stirring device was charged with 70.0 parts of propylene glycol monoethyl ether acetate, heated to 80 ° C., and the reaction vessel was filled with nitrogen. After the substitution, 13.3 parts of n-butyl methacrylate, 4.6 parts of 2-hydroxyethyl methacrylate, 4.3 parts of methacrylic acid, paracumylphenol ethylene oxide modified acrylate (“Aronix M110” manufactured by Toagosei Co., Ltd.) )) A mixture of 7.4 parts and 0.4 part of 2,2′-azobisisobutyronitrile was added dropwise over 2 hours. After completion of the dropping, the reaction was further continued for 3 hours to obtain an acrylic resin solution having a solid content of 30% by weight and a weight average molecular weight of 26000.
After cooling to room temperature, about 2 g of the resin solution was sampled and heated and dried at 180 ° C. for 20 minutes to measure the nonvolatile content. Propylene glycol monoethyl was added to the previously synthesized resin solution so that the nonvolatile content was 20% by weight. Ether acetate was added to obtain an acrylic resin solution (B-1) which is an alkali-soluble resin.

(Acrylic resin solution (B-2))
207 parts of cyclohexanone was charged into a separable four-necked flask equipped with a thermometer, a cooling pipe, a nitrogen gas introduction pipe, a dropping pipe, and a stirring device, heated to 80 ° C., and the flask was purged with nitrogen. 20 parts of acid, 20 parts of paracumylphenol ethylene oxide modified acrylate (Aronix M110 manufactured by Toa Gosei Co., Ltd.), 45 parts of methyl methacrylate, 8.5 parts of 2-hydroxyethyl methacrylate, and 2,2′-azobisisobutyronitrile 1.33 parts of the mixture was added dropwise over 2 hours. After completion of dropping, 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.
About 2 g of the resin solution was sampled and heated and dried at 180 ° C. for 20 minutes to measure the non-volatile content. Then, cyclohexanone was added to the previously synthesized resin solution so that the non-volatile content was 20% by weight, and the acrylic resin solution (B -2) was prepared. The weight average molecular weight (Mw) was 18000.

<Method for producing salt dye resin>
(Preparation of resin 1 having a cationic group in the side chain)
74.1 parts of isopropyl alcohol was charged into a four-necked separable flask equipped with a thermometer, a stirrer, a distillation tube, and a condenser, and the temperature was raised to 75 ° C. under a nitrogen stream. Separately, 33.2 parts of methyl methacrylate, 27.3 parts of n-butyl methacrylate, 27.3 parts of 2-ethylhexyl methacrylate, 12.2 parts of dimethylaminoethyl methyl chloride salt, and 15.6 parts of methyl ethyl ketone were homogenized. Thereafter, the mixture was placed in a dropping funnel, attached to a four-necked separable flask, and dropped over 2 hours. Two hours after the completion of the dropwise addition, it was confirmed that the polymerization yield was 98% or more from the solid content and the weight average molecular weight (Mw) was 7420, and the mixture was cooled to 50 ° C. Thereafter, 72 parts of isopropyl alcohol was added to obtain Resin 1 having a cationic group in the side chain whose resin component was 40% by weight. The ammonium salt value of the obtained resin was 33 mgKOH / g.

(Preparation of resin 2 having a cationic group in the side chain)
74.1 parts of isopropyl alcohol was charged into a four-necked separable flask equipped with a thermometer, a stirrer, a distillation tube, and a condenser, and the temperature was raised to 75 ° C. under a nitrogen stream. Separately, 15.7 parts of methyl methacrylate, 27.3 parts of n-butyl methacrylate, 27.3 parts of 2-ethylhexyl methacrylate, 12.2 parts of dimethylaminoethyl methyl chloride salt, 15.0 parts of hydroxyethyl methacrylate, methacrylic acid After 2.5 parts and 15.6 parts of methyl ethyl ketone were made uniform, they were charged into a dropping funnel, attached to a four-necked separable flask, and dropped over 2 hours. Two hours after the completion of the dropwise addition, it was confirmed that the polymerization yield was 98% or more from the solid content and the weight average molecular weight (Mw) was 7420, and the mixture was cooled to 50 ° C. Thereafter, 72 parts of isopropyl alcohol was added to obtain Resin 2 having a cationic group in the side chain whose resin component was 40% by weight. The ammonium salt value of the obtained resin was 33 mgKOH / g.

<Method for Producing Triarylmethane Salt Formation Compound>
(Preparation of triarylmethane salt-forming compounds (A1-1, A1-1a))
2,8-Diamino-1-naphthol-5,7-disulfonic acid (molecular weight 334) is dissolved in a 7-15 mol% sodium hydroxide solution and sufficiently mixed and stirred to obtain its sodium salt. This 2,8-diamino-1-naphthol-5,7-disulfonic acid sodium salt aqueous solution is heated to 70 to 90 ° C., and then Victoria Pure Blue dye (CI Basic Blue 7) is added dropwise little by little. . The Victoria Pure Blue dye may be dissolved in water and used as an aqueous solution. After dripping Victoria pure blue dye, it stirs at 70-90 degreeC for 40-60 minutes, and fully reacts. In order to confirm the end point of the reaction, it can be judged that the salt-forming compound was obtained with the reaction solution dropped on the filter paper and the point where the bleeding disappeared as the end point. The mixture is allowed to cool to room temperature with stirring, and then suction filtered and washed with water. After washing with water, the salt-forming compound remaining on the filter paper is dried by removing moisture with a dryer, and salted with Victoria Pure Blue dye and 2,8-diamino-1-naphthol-5,7-disulfonic acid. A compound, a triarylmethane salt-forming compound (A1-1) was obtained.
Furthermore, 20 parts by mass of rosin-modified maleic resin (acid value: 130, weight average molecular weight 1000, Marquide No. 32 manufactured by Arakawa Chemical Co., Ltd.) is added to 100 parts by mass of the obtained salt-forming compound, and mixed with a pressure kneader. (Material temperature 120 ° C. for 30 minutes), after cooling, finely pulverized with a mechanical pulverizer (Kryptron KTM1 type manufactured by Earth Technica Co., Ltd.) to obtain particles having an average particle size of 10 μm. Compound (A1-1a) was obtained.

(Preparation of triarylmethane salt-forming compound (A1-2))
2-Amino-1-naphthalenesulfonic acid (tobias acid) (molecular weight 223) is dissolved in a 9 mol% sodium hydroxide solution and sufficiently mixed and stirred to obtain its sodium salt. This 2-amino-1-naphthalenesulfonic acid (tobias acid) (molecular weight 223) sodium salt aqueous solution is heated to 85 ° C., and then Victoria Pure Blue dye (CI Basic Blue 7) is added dropwise little by little. The Victoria Pure Blue dye may be dissolved in water and used as an aqueous solution. After the Victoria pure blue dye is added dropwise, the mixture is stirred at 85 ° C. for 55 minutes to sufficiently react. In order to confirm the end point of the reaction, it can be judged that the salt-forming compound was obtained with the reaction solution dropped on the filter paper and the point where the bleeding disappeared as the end point. The mixture is allowed to cool to room temperature with stirring, and then suction filtered and washed with water. After washing with water, the salt-forming compound remaining on the filter paper is dried by removing moisture with a dryer, and a salt-forming compound of Victoria pure blue dye and 2-amino-1-naphthalenesulfonic acid (tobias acid), tria A reel methane salt-forming compound (A1-2) was obtained.

(Preparation of triarylmethane salt-forming compound (A1-3))
1-Amino-5-naphthalenesulfonic acid (Lorentzic acid) (molecular weight 223) is dissolved in 9 mol% sodium hydroxide solution and sufficiently mixed and stirred to obtain its sodium salt. This 1-amino-5-naphthalenesulfonic acid (Lorentzic acid) (molecular weight 223) sodium salt aqueous solution is heated to 85 ° C., and then Victoria Pure Blue dye (CI Basic Blue 7) is added dropwise little by little. The Victoria Pure Blue dye may be dissolved in water and used as an aqueous solution. After the Victoria pure blue dye is added dropwise, the mixture is stirred at 85 ° C. for 55 minutes to sufficiently react. In order to confirm the end point of the reaction, it can be judged that the salt-forming compound was obtained with the reaction solution dropped on the filter paper and the point where the bleeding disappeared as the end point. The mixture is allowed to cool to room temperature with stirring, and then suction filtered and washed with water. After washing with water, the salt-forming compound remaining on the filter paper is dried by removing moisture with a dryer, and a salt-forming compound of Victoria pure blue dye and 1-amino-5-naphthalenesulfonic acid (Lorentzic acid), tria A reel methane salt-forming compound (A1-3) was obtained.

(Preparation of triarylmethane salt-forming compound (A1-4))
1-Hydroxy-4-naphthalenesulfonic acid (NW acid) (molecular weight 224) is dissolved in a 9 mol% sodium hydroxide solution and sufficiently mixed and stirred to obtain its sodium salt. This 1-hydroxy-4-naphthalenesulfonic acid (NW acid) (molecular weight 224) sodium salt aqueous solution is heated to 85 ° C., and then Victoria Pure Blue dye (CI Basic Blue 7) is added dropwise little by little. The Victoria Pure Blue dye may be dissolved in water and used as an aqueous solution. After the Victoria pure blue dye is added dropwise, the mixture is stirred at 85 ° C. for 55 minutes to sufficiently react. In order to confirm the end point of the reaction, it can be judged that the salt-forming compound was obtained with the reaction solution dropped on the filter paper and the point where the bleeding disappeared as the end point. The mixture is allowed to cool to room temperature with stirring, and then suction filtered and washed with water. After washing with water, the salt-forming compound remaining on the filter paper is dried by removing moisture with a dryer, and a salt-forming compound of Victoria pure blue dye and 1-hydroxy-4-naphthalenesulfonic acid (NW acid), tria A reel methane salt forming compound (A1-4) was obtained.

(Preparation of Triarylmethane Salt Formation Compound (A1-5))
Phosphotungstic acid (molecular weight 2880) is dissolved in a 7-15 mol% sodium hydroxide solution and sufficiently mixed and stirred to obtain its sodium salt. After heating this phosphotungstic acid sodium salt aqueous solution to 70 to 90 ° C., Victoria Pure Blue dye (C.I.
Basic blue 7) is dripped little by little. The Victoria Pure Blue dye may be dissolved in water and used as an aqueous solution. After dripping Victoria pure blue dye, it stirs at 70-90 degreeC for 40-60 minutes, and fully reacts. In order to confirm the end point of the reaction, it can be judged that the salt-forming compound was obtained with the reaction solution dropped on the filter paper and the point where the bleeding disappeared as the end point. The mixture is allowed to cool to room temperature with stirring, and then suction filtered and washed with water. After washing with water, the salt-forming compound remaining on the filter paper was dried by removing moisture with a dryer, and a salt-forming compound of Victoria pure blue dye and phosphotungstic acid, a triarylmethane-based salt-forming compound (A1-5) )

(Preparation of triarylmethane salt-forming compound (A1-6))
Victoria Pure Blue Dye (CI Basic Blue 7) 5 g (9.73 mmol) manufactured by Tokyo Chemical Industry Co., Ltd. was dissolved in 30 mL of methanol and stirred with sodium naphthalenedisulfonate (Tokyo Chemical Industry Co., Ltd.) 1 .62 g (4.87 mmol) is added, and the mixture is stirred at room temperature for 1 hour to sufficiently react. Thereafter, the solution was concentrated by removing methanol with an evaporator, and then 100 mL of water was added, and the precipitate was collected by filtration and washed with water. After washing with water, the salt-forming compound remaining on the filter paper is dried by removing moisture with a dryer, and a salt-forming compound of Victoria pure blue dye and naphthalenedisulfonic acid, a triarylmethane-based salt-forming compound (A1-6) )

(Preparation of Triarylmethane Salt Formation Compound (A1-7))
Victoria Pure Blue Dye (CI Basic Blue 7) 5 g (9.73 mmol) manufactured by Tokyo Chemical Industry Co., Ltd. was dissolved in 30 mL of methanol and stirred with sodium naphthalene trisulfonate (Tokyo Chemical Industry Co., Ltd.) 1.41 Add g (3.24 mmol) and stir at room temperature for 1 hour to allow sufficient reaction. Thereafter, the solution was concentrated by removing methanol with an evaporator, and then 100 mL of water was added, and the precipitate was collected by filtration and washed with water. After washing with water, the salt-forming compound remaining on the filter paper is dried by removing moisture with a dryer, and a salt-forming compound of Victoria pure blue dye and naphthalene trisulfonic acid, a triarylmethane-based salt-forming compound (A1- 7) was obtained.

(Preparation of Triarylmethane Salt Formation Compound (A1-8))
Victoria Pure Blue Dye (CI Basic Blue 7) 5 g (9.73 mmol) manufactured by Tokyo Chemical Industry Co., Ltd. was dissolved in 30 mL of methanol, and sodium dodecyl sulfate (Tokyo Chemical Industry Co., Ltd.) 2. Add 81 g (9.73 mmol) and stir at room temperature for 1 hour to allow sufficient reaction. Thereafter, the solution was concentrated by removing methanol with an evaporator, and then 100 mL of water was added, and the precipitate was collected by filtration and washed with water. After washing with water, the salt-forming compound remaining on the filter paper is dried by removing moisture with a dryer, and a salt-forming compound of Victoria pure blue dye and dodecylsulfuric acid, triarylmethane-based salt-forming compound (A1-8) Got.

<Method for Producing Triarylmethane Colorant-Containing Solution>
(Preparation of Triarylmethane Salt-Forming Compound-Containing Solution (DB-1))
The following mixture was stirred and mixed so as to be uniform, and then filtered through a 5.0 μm filter to prepare a salt-forming compound-containing resin solution (DB-1).
Triarylmethane salt forming compound (A1-1): 11.0 parts Acrylic resin solution (B-1): 40.0 parts Propylene glycol monomethyl ether acetate (PGMAC): 49.0 parts

(Preparation of triarylmethane salt-forming compound-containing solution (DB-2 to 10))
Hereinafter, the salt-forming compound 1 is converted into a triarylmethane-based salt-forming compound (A1-1a, A1-2-8) or a triarylmethane-based dye (Victoria Pure Blue Dye; CI Basic Blue 7) shown in Table 1. Except having changed, it carried out similarly to said salt-forming compound containing solution (DB-1), and produced salt-forming compound containing solution (DB-2-10).

The prepared triarylmethane colorant-containing solutions are summarized in Table 1.

<Method for producing xanthene dye>
(Xanthene salt forming compound (A2-1))
In the following procedure, C.I. I. A xanthene-based salt-forming compound (A2-1) composed of Acid Red 52 and Resin 1 having a cationic group in the side chain was produced.
51 parts of vinyl-based resin 1 was added to 2000 parts of water, and after sufficient stirring and mixing, the mixture was heated to 60 ° C. On the other hand, 10 parts C.I. I. An aqueous solution in which Acid Red 52 was dissolved was prepared and added dropwise little by little to the previous resin solution. After dropping, the mixture was stirred at 60 ° C. for 120 minutes to sufficiently react. In order to confirm the end point of the reaction, it was judged that a salt-forming compound was obtained with the reaction solution dropped onto the filter paper and the point where the bleeding disappeared as the end point. After cooling to room temperature with stirring, suction filtration was performed, and after washing with water, the salt-forming compound remaining on the filter paper was dried by removing moisture with a dryer, and 32 parts of C.I. I. A salt-forming compound (A2-1) between acid red 52 and resin 1 having a cationic group in the side chain was obtained. At this time, C.I. in the salt-forming compound (A2-1). I. The content of the effective pigment component derived from Acid Red 52 was 25% by weight.

(Xanthene salt forming compound (A2-2))
In the following procedure, C.I. I. A salt-forming compound (A2-2) comprising Acid Red 52 and Resin 2 having a cationic group in the side chain was produced.
51 parts of the resin 2 having a cationic group was added to 2000 parts of water, and after sufficiently stirring and mixing, the mixture was heated to 60 ° C. On the other hand, 10 parts C.I. I. An aqueous solution in which Acid Red 52 was dissolved was prepared and added dropwise little by little to the previous resin solution. After dropping, the mixture was stirred at 60 ° C. for 120 minutes to sufficiently react. In order to confirm the end point of the reaction, it was judged that a salt-forming compound was obtained with the reaction solution dropped onto the filter paper and the point where the bleeding disappeared as the end point. After cooling to room temperature with stirring, suction filtration was performed, and after washing with water, the salt-forming compound remaining on the filter paper was dried by removing moisture with a dryer, and 32 parts of C.I. I. A salt-forming compound (A2-2) between acid red 52 and resin 2 having a cationic group in the side chain was obtained. At this time, C.I. in the salt-forming compound (A2-2). I. The content of the effective pigment component derived from Acid Red 52 was 25% by weight.

(Xanthene salt forming compound (A2-3))
In the following procedure, C.I. I. A salt-forming compound (A2-3) comprising Acid Red 289 and Resin 1 having a cationic group in the side chain was produced.
88 parts of the resin 1 having a cationic group in the side chain was added to 2000 parts of a 10% methanol aqueous solution, and the mixture was sufficiently stirred and mixed, and then heated to 60 ° C. On the other hand, 10 parts C.I. I. An aqueous solution in which Acid Red 289 was dissolved was prepared and added dropwise to the previous resin solution little by little. After dropping, the mixture was stirred at 60 ° C. for 120 minutes to sufficiently react. In order to confirm the end point of the reaction, it was judged that a salt-forming compound was obtained with the reaction solution dropped onto the filter paper and the point where the bleeding disappeared as the end point. After cooling to room temperature with stirring, suction filtration is performed, and after washing with water, the salt-forming compound remaining on the filter paper is dried by removing moisture with a dryer, and 43 parts of C.I. I. A salt-forming compound (A2-3) between Acid Red 289 and Resin 1 having a cationic group in the side chain was obtained. At this time, C.I. in the salt-forming compound (A2-3). I. The content of the effective pigment component derived from Acid Red 289 was 25% by weight.

(Xanthene salt forming compound (A2-4))
In the following procedure, C.I. I. A salt-forming compound (A2-4) composed of Acid Red 52 and distearyldimethylammonium chloride (Coatamine D86P) (the molecular weight of the cation moiety was 550) was produced.
In a 7-15 mol% sodium hydroxide solution, C.I. I. Acid Red 52 is dissolved, mixed and stirred sufficiently, heated to 70 to 90 ° C., and then Cotamine D86P is added dropwise little by little. Coatamine D86P may be dissolved in water and used as an aqueous solution. After adding Cotamine D86P dropwise, the mixture is stirred at 70 to 90 ° C. for 60 minutes to sufficiently react. In order to confirm the end point of the reaction, it can be judged that the salt-forming compound was obtained with the reaction solution dropped on the filter paper and the point where the bleeding disappeared as the end point. After cooling to room temperature with stirring, suction filtration is performed, and after washing with water, the salt-forming compound remaining on the filter paper is dried by removing moisture with a dryer. I. A salt-forming compound (A2-4) of acid red 52 and distearyldimethylammonium chloride was obtained. At this time, C.I. in the salt-forming compound (A2-4). I. The content of the effective pigment component derived from Acid Red 52 was 25% by weight.

(Xanthene salt forming compound (A2-5))
In the following procedure, C.I. I. A salt-forming compound (A2-5) composed of Acid Red 52 and dialkyl (alkyl is C14 to C18) dimethylammonium chloride (Arcade 2HT-75) (the molecular weight of the cation moiety is 438 to 550) was produced.
In a 7-15 mol% sodium hydroxide solution, C.I. I. Acid Red 52 is dissolved, mixed and stirred sufficiently, heated to 70 to 90 ° C., and then Arcard 2HT-75 is added dropwise little by little. Arcade 2HT-75 may be dissolved in water and used as an aqueous solution. After dropping Arcade 2HT-75, the mixture is stirred at 70 to 90 ° C. for 60 minutes to sufficiently react. In order to confirm the end point of the reaction, it can be judged that the salt-forming compound was obtained with the reaction solution dropped on the filter paper and the point where the bleeding disappeared as the end point. After cooling to room temperature with stirring, suction filtration is performed, and after washing with water, the salt-forming compound remaining on the filter paper is dried by removing moisture with a dryer. I. A salt-forming compound (A2-5) of acid red 52 and dialkyl (alkyl is C14 to C18) dimethylammonium chloride was obtained. At this time, C.I. in the salt-forming compound (A2-5). I. The content of the effective pigment component derived from Acid Red 52 was 25% by weight.

(Xanthene salt forming compound (A2-6))
In the following procedure, C.I. I. A salt-forming compound (A2-6) consisting of Acid Red 87 and distearyldimethylammonium chloride (Coatamine D86P) (the molecular weight of the cation moiety was 550) was produced.
In a 7-15 mol% sodium hydroxide solution, C.I. I. Acid Red 87 is dissolved, sufficiently mixed and stirred, heated to 70 to 90 ° C., and then Cotamine D86P is added dropwise little by little. Coatamine D86P may be dissolved in water and used as an aqueous solution. After adding Cotamine D86P dropwise, the mixture is stirred at 70 to 90 ° C. for 60 minutes to sufficiently react. In order to confirm the end point of the reaction, it can be judged that the salt-forming compound was obtained with the reaction solution dropped on the filter paper and the point where the bleeding disappeared as the end point. After cooling to room temperature with stirring, suction filtration is performed, and after washing with water, the salt-forming compound remaining on the filter paper is dried by removing moisture with a dryer. I. A salt-forming compound of acid red 87 and distearyldimethylammonium chloride, a salt-forming compound (A2-6) was obtained. At this time, C.I. in the salt-forming compound (A2-6). I. The content of the effective pigment component derived from Acid Red 87 was 25% by weight.

(Sulphonic acid amide compound of xanthene acid dye)
C. I. Acid Red 52 was converted to a sulfonyl chloride by a conventional method and then reacted with a theoretical equivalent of 2-ethylhexylamine in dioxane to obtain C.I. I. A sulfonic acid amide compound of Acid Red 52 was obtained. (Based on the description of JP-A-6-194828.) At this time, C.I. I. The content of the effective pigment component derived from Acid Red 52 was 25% by weight.

<Method for producing xanthene dye-containing solution>
(Preparation of xanthene dye-containing solution (DA-1))
The following mixture was stirred and mixed to be uniform, and then filtered through a 5.0 μm filter to prepare a xanthene dye-containing solution (DA-1).

Xanthene salt forming compound (A2-1): 20.0 parts propylene glycol monomethyl ether acetate (PGMAC): 80.0 parts

(Preparation of xanthene dye-containing solution (DA-2 to 6))
Hereinafter, the colorant-containing resin solution (DA-1) except that the xanthene-based salt-forming compound (A2-1) is changed to the salt-forming compound (A2-2-6) or the sulfonic acid amide compound shown in Table 1. In the same manner as above, xanthene dye-containing solutions (DA-2 to 7) were prepared.

The produced xanthene dye-containing solutions are summarized in Table 1.

<Production method of fine pigment>
(Blue refined pigment (PB-1))
Blue pigment C.I. I. Pigment Blue 15: 6 (PB15: 6) (“Rionol Blue ES” manufactured by Toyo Ink Manufacturing Co., Ltd.) 500 parts, 2500 parts of sodium chloride, and 250 parts of diethylene glycol were charged into a stainless steel 1 gallon kneader (manufactured by Inoue Seisakusho). The mixture was kneaded at 120 ° C. for 12 hours. Next, the kneaded product is poured into 5 liters of warm water, stirred for 1 hour while heating to 70 ° C. to form a slurry, filtered and washed repeatedly to remove sodium chloride and diethylene glycol, and then dried at 80 ° C. overnight. As a result, a blue refined pigment (PB-1) was obtained. The average primary particle diameter of the obtained pigment was 25 nm.

(Purple refinement treatment pigment (PV-1))
Dioxazine-based purple pigment C.I. I. 500 parts of Pigment Violet 23 (PV23) (“Fast Violet RL” manufactured by Clariant), 2500 parts of sodium chloride, and 250 parts of polyethylene glycol (manufactured by Tokyo Chemical Industry Co., Ltd.) were charged into a stainless 1 gallon kneader (manufactured by Inoue Seisakusho). The mixture was kneaded at 120 ° C. for 12 hours. Next, this mixture is poured into about 5 liters of warm water, heated to about 70 ° C. and stirred with a high speed mixer for about 1 hour to form a slurry, then filtered and washed to remove sodium chloride and diethylene glycol, It dried at 80 degreeC all day and night, and obtained the purple refinement | purification processing pigment (PV-1). The average primary particle diameter of the obtained pigment was 30 nm.

<Method for preparing pigment dispersant solution>
A pigment dispersant (“Ajisper PB821” manufactured by Ajinomoto Fine Techno Co., Ltd.) was diluted with propylene glycol monomethyl ether acetate to prepare a pigment dispersant solution having a nonvolatile content of 30% by weight.

<Method for producing pigment dispersion>
(Pigment dispersion (P-B1))
12.0 parts of blue refined pigment (PB-1), 32.5 parts of acrylic resin solution (B-1), 5 parts of pigment dispersant solution, and 50.5 parts of ethylene glycol monomethyl ether acetate are stirred and mixed uniformly. After that, using a zirconia bead having a diameter of 0.5 mm, it was dispersed for 3 hours with an Eiger mill (“Mini Model M-250 MKII” manufactured by Eiger Japan), filtered through a 5 μm filter, and a PB15: 6 pigment dispersion. (P-B1) was obtained.

(Pigment dispersion (P-V1)
PV23 pigment dispersion (P- V1) was prepared.

[Example 1]
(Preparation of colored composition 1)
The following mixture was stirred and mixed so as to be uniform, and then filtered through a 5.0 μm filter to prepare a colored composition 1.

Triarylmethane colorant-containing solution (DB-1): 20.1 parts Xanthene dye-containing solution (DA-1): 18.9 parts Binder resin solution (B-1): 3.4 parts Photopolymerization initiator 1.4 parts 2- (dimethylamino) -2-[(4-methylphenyl) methyl] -1- [4- (4-morpholinyl) phenyl] -1-butanone (“Irgacure 379” manufactured by Ciba Japan) )
Sensitizer: 0.2 part 2,4-diethylthioxanthone (“Kayacure DETX-S” manufactured by Nippon Kayaku Co., Ltd.)
Photopolymerizable monomer: 5.0 parts dipentaerythritol hexaacrylate (“Aronix M-402” manufactured by Toagosei Co., Ltd.)
Solvent: 51.0 parts propylene glycol monomethyl ether acetate

[Examples 2 to 16, Comparative Examples 1 to 4]
(Preparation of colored compositions 2 to 20)
Hereinafter, the coloring composition of Example 1 except that the triarylmethane-based colorant-containing solution, the xanthene-based dye-containing solution, the pigment dispersion, and the binder resin solution are changed to the types and blending amounts (parts by weight) shown in Table 2. In the same manner as Product 1, colored compositions 2 to 20 were produced.

[Evaluation of coloring composition]
The resulting colored composition was evaluated for brightness, heat resistance, and solvent resistance by the following methods. The results are shown in Table 4.

<Lightness evaluation>
The obtained colored composition was applied onto a glass substrate in a film thickness such that x = 0.144 and y = 0.084 using a C light source, and was exposed to ultraviolet rays through a mask having a predetermined pattern. Thereafter, an alkali developer was sprayed by spraying to remove the uncured portion and form a desired pattern. About the obtained coating film, the brightness before and behind heat processing at 230 degreeC for 20 minutes was measured with the microspectrophotometer ("OSP-SP200" by Olympus Optical Co., Ltd.).
If the chromaticity is shifted, a colored composition in which the ratio of the triarylmethane-based colorant-containing solution, the xanthene-based dye-containing solution and the pigment dispersion is appropriately changed is prepared, the chromaticity is measured, and a calibration curve is drawn. The brightness at the desired chromaticity was calculated.
In the evaluation results, “◎” is particularly good, “○” is good, “Δ” is a level where there is no problem in use, and “×” corresponds to a state where it cannot be used. Less than 5 △: 10.5 or more and less than 11.0 ×: 10.5 or less

<Heat resistance evaluation>
The substrate obtained by lightness evaluation was measured with a microspectrophotometer ("OSP-SP200" manufactured by Olympus Optical Co., Ltd.) before and after heat treatment at 230 ° C for 60 minutes in an oven, and the difference from lightness before and after heat treatment at 230 ° C for 20 minutes It was measured. The rank of evaluation is as follows. In the evaluation results, ◯ is good, Δ is a level that does not cause a problem in use, and × corresponds to a state where it cannot be used.

Lightness difference (ΔY) = | (Lightness Y after heat resistance) − (Lightness Y before heat resistance) |
○: Less than 0.4 Δ: 0.4 or more and less than 0.8 ×: 0.8 or more

<Chemical resistance evaluation>
The substrate obtained by the lightness evaluation was measured for chromaticity ([L * (1), a * (1), b * (1)]) with a C light source by a microspectrophotometer ("OSP-SP200" manufactured by Olympus Optical Co., Ltd.). ).
This substrate was immersed in N-methyl-2-pyrrolidone at room temperature for 5 minutes, washed with running water for 1 minute, and then air-dried. Measure the chromaticity ([L * (2), a * (2), b * (2)]) of the substrate obtained, and set the difference (color difference) from the chromaticity of the substrate before immersion to JIS Z 8729. Calculated in accordance with the above.
The rank of evaluation is as follows. In the evaluation results, ◯ is good, Δ is a level that does not cause a problem in use, and × corresponds to a state where it cannot be used.
ΔEab * = √ ((L * (2)-L * (1)) ² + (a * (2)-a * (1)) ² + (b * (2)-b * (1)) ² )
○: ΔEab * is less than 3 Δ: ΔEab * is 3 or more and less than 8 ×: ΔEab * is 8 or more

The coloring compositions 1 to 15 of Examples 1 to 15 were all good in lightness, heat resistance, and chemical resistance. In particular, Example 10 showed higher brightness.
Moreover, the coloring compositions 1-15 of Examples 1-15 whose xanthene pigment | dye [A2] is a salt-forming compound of a xanthene acid dye were the results excellent in tolerance.

  On the other hand, although the coloring composition 17 of Comparative Example 1 is of a quality that causes no problem when used as a color filter, it is poor in heat resistance and chemical resistance and is difficult to use. Moreover, the coloring composition (18-20) of Comparative Examples 2-4 was a result with low brightness.

<Production of color filter>
First, the red photosensitive coloring composition and the green photosensitive coloring composition used for preparation of a color filter were produced.

(Preparation of red photosensitive coloring composition (RR-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. A red pigment dispersion 1 was prepared by filtration through a 0.0 μm filter.

Red pigment (CI Pigment Red 254) 9.6 parts Red Pigment (CI Pigment Red 177) 2.4 parts Resin-type dispersant ("EFKA4300" manufactured by Ciba Japan) 1.0 part Acrylic resin Solution (B-1) 35.0 parts Propylene glycol monomethyl ether acetate 52.0 parts

Subsequently, the mixture having the following composition was stirred and mixed so as to be uniform, and then filtered through a 1.0 μm filter to prepare a red colored composition (RR-1).

Red pigment dispersion 1 42.0 parts Acrylic resin solution (B-1) 13.2 parts Photopolymerizable monomer (“Aronix M400” manufactured by Toagosei Co., Ltd.) 2.8 parts Photopolymerization initiator (Ciba Japan) "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 green photosensitive coloring composition (RG-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. A green pigment dispersion 1 was prepared by filtration through a 0.0 μm filter.

Green pigment (CI Pigment Green 58): 7.04 parts Yellow pigment (CI Pigment Yellow 150): 3.96 parts Acrylic resin solution (B-1): 35.0 parts Resin-type dispersant solution ("EFKA4300" manufactured by Ciba Japan Co., Ltd.): 5.0 parts Propylene glycol monomethyl ether acetate: 49.0 parts

Then, after stirring and mixing the mixture of the following composition so that it might become uniform, it filtered with a 1.0 micrometer filter, and produced the green coloring composition (RG-1).

Green pigment dispersion 1: 50.0 parts Acrylic resin solution (B-1): 7.5 parts Photopolymerizable monomer: 2.0 parts (“Aronix M-402” manufactured by Toagosei Co., Ltd.)
Dipentaerythritol hexaacrylate Photopolymerization initiator (“OXE-02” manufactured by Ciba Japan): 1.5 parts Cyclohexanone: 39.0 parts

(Production of color filter)
A black matrix was patterned on a glass substrate, and a red colored composition (RR-1) was applied on the substrate with a spin coater to form a colored film. The film was irradiated with ultraviolet rays of 150 mJ / cm ² 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. Formed. Here, the red filter segment was adjusted to a chromaticity of x = 0.640 and y = 0.330 in a C light source (hereinafter also used for green and blue) after heat treatment at 230 ° C. Further, by the same method, the green filter segment is matched with the chromaticity of x = 0.290 and y = 0.600 using the green coloring composition (RG-1), and the blue filter segment is the present invention. The blue coloring composition 4 was used so that the chromaticity of x = 0.150 and y = 0.060 was met, and each filter segment was formed to obtain a color filter.

  By using the coloring composition for a color filter of the present invention, the brightness of the color filter can be increased, and other physical properties can be suitably used without any problem.

Claims (6)

  A color filter coloring composition comprising a colorant [A], a binder resin, and an organic solvent, wherein the colorant [A] is a triarylmethane basic dye, a flavin basic dye, or an auramine basic A salt-forming compound [A1] comprising any one selected from the group consisting of a dye, a safranin-based basic dye, a phloxine-based basic dye, and a methylene blue-based basic dye, and a counter compound having a molecular weight in the range of 200-3500, And a coloring composition for a color filter, comprising a xanthene dye [A2].   The coloring composition for a color filter according to claim 1, wherein the basic dye constituting the salt-forming compound [A1] is a triarylmethane basic dye.   The coloring composition for a color filter according to claim 1 or 2, wherein the xanthene dye [A2] is a salt forming compound of a xanthene acid dye and / or a sulfonic acid amide compound of a xanthene acid dye.   Xanthene acid dyes are C.I. I. Acid Red 52, C.I. I. Acid Red 87, C.I. I. Acid Red 92, C.I. I. Acid Red 289, and C.I. I. The coloring composition for a color filter according to claim 3, wherein the coloring composition is at least one selected from the group consisting of Acid Red 388.   Furthermore, the coloring composition for color filters of any one of Claims 1-4 containing a photopolymerizable monomer and / or a photoinitiator.   A color filter comprising a filter segment formed from the colored composition for color filter according to any one of claims 1 to 5 on a substrate.