JP2002338825A - Colored resin composition, colored photosensitive composition and color filter - Google Patents

Abstract

PROBLEM TO BE SOLVED: To provide a colored resin composition containing a dye as a colorant, excellent in transparency (light transmitting properties) and having a high color density and a good hue (particularly in blue color). SOLUTION: The colored resin composition comprises at least a binder polymer and a colorant, where at least one colorant is a compound represented by general formula (1) [wherein R<1> -R<8> are each H, an alkyl, hydroxyl, alkoxyl, amino, alkylamino or dialkylamino group, a halogen atom, a sulfonyl group, a sulfonate, a carboxyl group, a carboxylate, an ester group or an amide group; and A<1> -A<8> are each N or CH (provided that at least one of A<1> -A<8> is N)].

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a dye-containing colored resin composition and a colored photosensitive composition, and a color filter having excellent optical characteristics and suitable for a liquid crystal color display and the like.

[0002]

2. Description of the Related Art Various types of color filters for display devices have been provided, and color filters for liquid crystal displays will be described below as typical examples. Liquid crystal displays are widely used, from small-area displays such as watches and cameras to large-area displays such as computer terminal displays and television image displays.In recent years, color displays have been used mainly for large-area applications. Is progressing rapidly. The color filter is indispensable for the color display of the liquid crystal display, and is an important component that affects the performance of the liquid crystal display, and is finely patterned into various shapes to display a high-definition image.

[0003] As a conventional method for manufacturing a color filter, for example, a dyeing method, an ink jet method, a printing method, a photoresist method (photolithography method) and the like are known. In the dyeing method, after forming a predetermined pattern, a color filter is formed by repeating a process of dyeing in an appropriate dyeing bath and a process of anti-dyeing treatment for each of three colors of red, green, and blue. It is a manufacturing method. However, this method has the drawback that the steps are complicated and the total number of steps is large. On the other hand, the number of processes is smaller,
As an efficient method of manufacturing a color filter, an ink jet method in which ink is ejected onto a transparent substrate using an ink jet apparatus and coloring is performed by fixing the ink, and a printing method in which the ink is transferred to the transparent substrate using a printing machine are proposed. Have been. However, these methods have a problem that it is difficult to form high-definition pixels because alignment adjustment of the position is performed by an inkjet head, a printing machine, or a printing plate.

[0004] On the other hand, in the photolithography method, a colored photosensitive resin composition containing a polymer conjugate and a coloring agent is used, applied to a transparent substrate, formed into a film, and then the colored layer is irradiated with light. By patterning and developing further,
A color pattern can be formed. Although this method is similar to the dyeing method, this process is repeated for each color,
Since a dyeing step and an anti-dyeing treatment are not required, there is an advantage that not only the number of steps can be simplified as compared with that of the dyeing method, but also control of spectral characteristics and reproducibility can be easily secured. Furthermore, the resolution of the photolithography method is large, and it has been difficult by the printing method and the ink-jet method.
It is also possible to manufacture a higher definition color filter, and in recent years, it has become the mainstream of a method of manufacturing a color filter for a liquid crystal display.

In this photolithography method, a pigment excellent in heat resistance, light resistance and chemical resistance is generally used as a colorant. However, it is known that the pigment has a depolarizing effect due to having a certain particle diameter, and the contrast ratio of the color display of the liquid crystal display is reduced. Further, it is difficult to obtain high transparency (light transmission) in a system using a pigment, and there is a limit in improving the brightness of a color filter. Furthermore, since pigments are insoluble in solvents and polymers,
Although the colored photosensitive resin composition is obtained as a dispersion, it is difficult to stabilize the dispersion.

On the other hand, since dyes are generally soluble in solvents and polymers, they are stable even in colored photosensitive resin compositions without causing aggregation or the like. Further, the color filter obtained using the colored photosensitive resin composition in which the dye is dispersed has no depolarizing effect because the dye is dispersed at the molecular level, and is excellent in transparency (light transmission). However, if the dye itself does not have a large extinction coefficient in the desired light absorption wavelength region, the purity and vividness of hues including R (red), G (green), and B (blue) decrease. Or the desired density cannot be obtained. For example, copper phthalocyanine has been widely studied as a coloring material (dye) for blue use having a light absorption around the wavelength of 550 to 600 nm because of its large extinction coefficient. Cannot be used in practice because the main absorption of the dye is on the long wavelength side (up to 600 nm). Has been used. With these dyes, although a good hue was obtained to some extent, in order to obtain a sufficient concentration, it was necessary to apply the composition to a thick film. There has been a problem that the improvement effect is impaired and cost reduction cannot be achieved.

On the other hand, JP-A-2000-129150, JP-A-2000-26515, and JP-A-2000-44822 propose that an acrylic group is covalently bonded to a dye and copolymerized with another polymerizable monomer. . But,
Although it is effective as a means to solve the problems of dye elution and sublimation, it is only to bind the dye to the polymer side chain, so various problems associated with the main absorption wavelength and extinction coefficient of the dye as described above Has not yet been resolved.

[0008]

SUMMARY OF THE INVENTION In view of the above, an object of the present invention is to solve the above-mentioned conventional problems and achieve the following objects. That is, the present invention firstly provides a colored resin composition and a colored photosensitive composition which contain a dye as a coloring agent, are excellent in transparency (light transmission), and have good color density and hue (especially blue). Secondly, a color filter having excellent transparency (light transmission) and hue (especially blue), high density even in a thin film (especially blue), and excellent optical characteristics can be manufactured at low cost. The purpose is to provide.

[0009]

Means for solving the above problems are as follows. That is, <1> a colored resin composition comprising at least a binder polymer and a coloring agent, wherein at least one of the coloring agents is a compound represented by the following general formula (1).

[0010]

Embedded image

[In the general formula (1), R ¹ , R ² , R ³ , R ⁴ ,
R ⁵ , R ⁶ , R ⁷ and R ⁸ each independently represent a hydrogen atom, an alkyl group, a hydroxyl group, an alkoxy group, an amino group,
An alkylamino group, a dialkylamino group, a halogen atom, a sulfonic acid group, a sulfonic acid salt, a carboxylic acid group, a carboxylic acid salt, an ester group, and an amide group may be the same or different. ^{A 1, A 2, A 3} , A 4, A 5, A 6, A 7
And A ⁸ each independently represent N or CH, which may be the same or different, and at least one of A ^{1 to} A ⁸ represents N. ]

<2> The colored resin composition according to <1>, wherein the binder polymer is a binder polymer having an acidic group. <3> A color resin composition according to <1> or <2>, a polyfunctional monomer having two or more ethylenically unsaturated double bonds, and a photopolymerization initiator. It is a colored photosensitive composition. <4> In a color filter including a filter film in which two or more pixel patterns having different spectral characteristics are arranged adjacent to each other on the same substrate, the filter film may be configured such that the <
A color filter formed using the colored photosensitive composition described in 3>.

[0013]

DESCRIPTION OF THE PREFERRED EMBODIMENTS The present invention will be described below in order. <Colored resin composition> The colored resin composition of the present invention contains at least a binder polymer and a colorant, and at least one of the colorants is an azaphthalocyanine compound represented by the following general formula (1). (Dye). Further, other components may be included as needed.

(Colorant) The colored resin composition of the present invention contains, as a colorant, at least one azaphthalocyanine compound represented by the following general formula (1). It may contain a plurality of types of compounds and may further contain other known coloring agents. The azaphthalocyanine compound has at least one of the groups (A ^{1 to} A ⁸ in the general formula) constituting the 6-membered ring in the structure.
Finally, it is a dye having a nitrogen atom (N), and has a main absorption (light absorption wavelength) for use in blue at about 550 nm and a large extinction coefficient (absorbance). And a good blue hue with a high color density and other hues associated therewith can be obtained. Further, even when the layer is formed by coating, the film can be made thinner, and the transparency (light transmission) can be greatly improved, which also contributes to cost reduction. Hereinafter, the azaphthalocyanine compound represented by the following general formula (1) will be described in detail.

[0015]

Embedded image

In the general formula (1), R ¹ , R ² , R ³ ,
R ⁴ , R ⁵ , R ⁶ , R ⁷ and R ⁸ each independently represent a hydrogen atom, an alkyl group, a hydroxyl group, an alkoxy group, an amino group, an alkylamino group, a dialkylamino group, a halogen atom, a sulfonic acid group, Acid salts, carboxylic acid groups,
Represents carboxylate, ester group and amide group. R ¹
A plurality of R ⁸ to R ⁸ may represent the same group or different groups.

The alkyl group may be unsubstituted or have a substituent. When the alkyl group has a substituent, examples of the substituent include a methoxy group, an ethoxy group, a butoxy group and a
-Methoxyethoxy group, phenyl group, 2,4-di-t-
Amylphenyloxy group, chloro group, bromo group, dimethylamino group, diethylamino group, acetylamino group, hydroxyl group, carboxylic acid, sulfonic acid, dibutylaminocarbamoyl group, diethylaminosulfamoyl group and the like, among which methoxy group, A 2,4-di-t-amylphenyloxy group, a chloro group and a bromo group are preferred. The alkyl group is preferably an alkyl group having 1 to 20 carbon atoms, for example, a methyl group, an ethyl group, a primary propyl group,
Isopropyl, primary butyl, secondary butyl, tertiary butyl, isobutyl, amyl, tertiary amyl, hexyl, octyl, tertiary octyl, 2-ethylhexyl, decyl, dodecyl Octadecyl group, chloromethyl group, dimethylaminomethyl group, diethylaminomethyl group, 3-acetylaminopropyl group, 3-dimethylaminopropyl group, 6-hydroxyhexyl group, 2-
Preferable examples include a hydroxysulfonylethyl group and a 4-hydroxycarbonylphenoxymethyl group. Among them, a methyl group, an ethyl group, a primary butyl group, a secondary butyl group, a tertiary butyl group, a hexyl group, a dimethylaminomethyl group, and a diethylaminomethyl group are particularly preferred.

The alkoxy group may be unsubstituted or substituted, and is preferably an alkoxy group having 1 to 20 carbon atoms. Examples thereof include a methoxy group, an ethoxy group, an isopropoxy group, a butoxy group and a hexyloxy group. Group, octyloxy group, 2-ethylhexyloxy group, dodecyloxy group, heptadecyloxy group, undecyloxy group,
A 2- (2 ′, 4′-di-t-amylphenyloxy) ethyloxy group, a 4-bromobutoxy group, a phenethyloxy group, and the like are preferred. Among them, a methoxy group, an ethoxy group, a butoxy group, a hexyloxy group, a 2-ethylhexyloxy group, and a 2- (2 ′, 4′-di-t-amylphenyloxy) ethyloxy group are particularly preferable. Substituents having a substituent and preferred embodiments thereof are the same as those in the alkyl group.

The alkylamino group may be unsubstituted or substituted, and is preferably an alkylamino group having 1 to 12 carbon atoms. For example, a methylamino group, an ethylamino group, a butylamino group, Xylamino group, heptylamino group, 2-ethylhexylamino, octylamino group, 3,5,5-trimethylhexylamino group, decylamino group, dodecylamino group, 2- (N, N-dimethylamino) ethylamino group, 3- (N, N-diethylamino) propylamino group, phenethylamino group, 2-
A preferred example is a hydroxyethylamino group. Among them, methylamino group, 2-ethylhexylamino group, 3
-(N, N-diethylamino) propylamino group, 2-
A hydroxyethylamino group is particularly preferred. Substituents having a substituent and preferred embodiments thereof are the same as those in the alkyl group.

The dialkylamino group may be unsubstituted or substituted, and is preferably a dialkylamino group having 2 to 24 carbon atoms. Examples thereof include a dimethylamino group, a diethylamino group, a diisopropylamino group and a dibutylamino group. Group, dihexylamino group, bis (2-ethylhexyl) amino group, dioctylamino group, N-ethyl-N-methylamino group, N-butyl-N-methylamino group, N- (4-N ', N'- Preferable examples include a diethylaminosulfamoyl) butyl-N-methylamino group, a bis (2-dimethylaminoethyl) amino group, and a bis (dibutylaminocarbamoylmethyl) amino group. Among them, dimethylamino group, diethylamino group, dibutylamino group, dihexylamino group, dioctylamino group, N
-Butyl-N-methylamino group, N- (4-N ′, N ′
-Diethylaminosulfamoyl) butyl-N-methylamino group, bis (2-dimethylaminoethyl) amino group and bis (dibutylaminocarbamoylmethyl) amino group are particularly preferred. Substituents having a substituent and preferred embodiments thereof are the same as those in the alkyl group.

Preferred examples of the halogen atom include a chlorine atom, a bromine atom and an iodine atom, and among them, a bromine atom and a chlorine atom are preferred.

The sulfonate (—SO ₃ M) and carboxylate (—COOM) include a counter ion forming a salt.
Groups wherein (M) is an inorganic cation or an organic cation. Examples of the counter ion include ions of sodium, potassium, calcium, magnesium, ammonium, tetrabutylammonium and the like. Among them, sodium, potassium and ammonium are preferred.

The ester group may be unsubstituted or may have a substituent, for example, methoxycarbonyl, ethoxycarbonyl, hexyloxycarbonyl, bromomethyloxycarbonyl, 2- (N, N-
Dimethylamino) ethyloxycarbonyl group, 3-
(N, N-dimethylamino) propyloxycarbonyl group, phenoxycarbonyl group, 3-chlorophenoxycarbonyl group, methoxysulfonyl group, ethoxysulfonyl group, butoxysulfonyl group, phenoxysulfonyl group, 3- (N, N-diethylamino) propyl Preferable examples include an oxysulfonyl group, a 4-bromobutoxycarbonyl group, and a 4-methylphenoxysulfonyl group. Among them, a hexyloxycarbonyl group, a bromomethyloxycarbonyl group, a 3- (N, N-dimethylamino) propyloxycarbonyl group, a 3- (N, N-diethylamino) propyloxysulfonyl group, an ethoxycarbonyl group, and a 4-methylphenoxy group Sulfonyl groups are preferred. Substituents having a substituent and preferred embodiments thereof are the same as those in the alkyl group.

The amide group may be unsubstituted or substituted, for example, a methylaminocarbonyl group, a butylaminocarbonyl group, a 2-ethylhexylaminocarbonyl group, a 2-methoxyethylaminocarbonyl group , 3- (N, N-diethylamino) propylaminocarbonyl group, 4- (N, N-diethylamino) butylaminocarbonyl group, 6- (N, N-dimethylamino)
Hexylaminocarbonyl group, phenylaminocarbonyl group, 3-butoxyphenylaminocarbonyl group, diethylaminocarbonyl group, dibutylaminocarbonyl group, bis-2- (N, N-dimethylamino) ethylaminocarbonyl group, hexylaminosulfonyl group Benzylaminosulfonyl group, 2-methoxyphenylaminosulfonyl group, 3- (N, N-diethylamino) propylaminosulfonyl group, dimethylaminosulfonyl group, dipropylaminosulfonyl group, and acetylamino group. Among them, 2-ethylhexylaminocarbonyl group, 6- (N, N-dimethylamino) hexylaminocarbonyl group, 3- (N, N-diethylamino)
A propylaminosulfonyl group is preferred. Substituents having a substituent and preferred embodiments thereof are the same as those in the alkyl group.

Among the above, R ^{1 to} R ⁸ represent a hydrogen atom, a halogen atom, an alkyl group, an alkoxy group, an alkylamino group, a dialkylamino group, a sulfonic acid group,
A carboxylic acid group, an ester group and an amide group are preferred, and a hydrogen atom, a chlorine atom, a methyl group, an ethyl group, an isopropyl group, a butyl group and a methoxy group are particularly preferred.

In the general formula (1), A ¹ , A ² , A ³ ,
A ⁴ , A ⁵ , A ⁶ , A ⁷ and A ⁸ each independently represent N or CH, and a plurality of these may represent the same group or different groups; ^At least one of ^{1 to} A ⁸ represents N. Among them, in each combination of A ¹ and A ² , A ³ and A ⁴ , A ⁵ and A ⁶ , and A ⁷ and A ⁸ , those in which either represents N or both represent N are preferable.

Hereinafter, specific examples of the azaphthalocyanine compound represented by the general formula (1) (exemplified compounds (1) to (5))
(8)). However, the present invention is not limited to these.

[0028]

Embedded image

[0029]

Embedded image

[0030]

Embedded image

The synthesis of the azaphthalocyanine compound of the present invention is not particularly limited, and is generally preferably carried out by a known addition reaction using a heteroaromatic six-membered ring compound having two nitriles at the ortho position as a starting material. Can be. For example, the exemplified compound (1) can be synthesized as follows. In addition, other exemplary compounds can be performed according to these methods.

-Synthesis of Exemplified Compound (1)-First, 3-benzyl-5- (2-hydroxyethyl) -4
-Methylthiazolium chloride (BHMTC) 22.4
500 parts by mass of ethanol was added to the parts by mass, and the mixture was stirred at room temperature, 95.0 parts by mass of heptylaldehyde and 50 parts by mass of triethylamine were added dropwise, and the mixture was stirred under reflux for 4 hours. After the obtained reaction product was cooled to room temperature, ice water 10
And then neutralized with hydrochloric acid. Then, the mixture was extracted with ethyl acetate and concentrated to obtain a crude product. To 96 parts by mass of the obtained crude product, 188 parts by mass of copper acetate, 40 parts by mass of methanol, and 400 parts by mass of 50% acetic acid water were added, and the mixture was stirred under reflux for 10 hours. The resulting reaction product was cooled to room temperature, filtered, extracted with ethyl acetate, concentrated, purified by column with hexane and ethyl acetate, and further recrystallized with ethanol to give 7,8-dioxotetradecane. 4 parts by weight were obtained. Subsequently, 10.8 parts by mass of diaminomalononitrile and 150 parts by mass of ethanol were added to 22.6 parts by mass of the obtained 7,8-dioxotetradecane, and the mixture was stirred under reflux for 8 hours. The obtained reaction product was cooled to room temperature, concentrated, and purified by column with hexane and ethyl acetate to obtain 2,3.8 parts by mass of 2,3-dicyano-5,6-dihexyl-1,4-pyrazine. Subsequently, the 2,3-dicyano-5,6-dihexyl- obtained above.
To 9 parts of 1,4-pyrazine, 0.7 parts by mass of cuprous chloride,
40.2 parts by mass of (NH ₄ ) ₆ Mo ₇ O _{2 and} 100 parts by mass of o-dichlorobenzene were added, and the mixture was stirred at 200 ° C. for 14 hours. After the obtained reaction product was cooled to room temperature, it was poured into 500 parts by mass of 10% hydrochloric acid, stirred for 1 hour and filtered, added to 500 parts by mass of methanol, further stirred for 1 hour and filtered. The obtained crude product was recrystallized from dimethylacetamide and washed with methanol to obtain 1.5 parts by mass of an azaphthalocyanine compound (exemplified compound (1)).

The content of the azaphthalocyanine compound represented by the general formula (1) in the colored resin composition of the present invention is preferably from 0.1 to 400% by mass based on the mass of the binder polymer described below. , 1 to 200% by mass. If the content is less than 0.1% by mass, good density and hue may not be obtained,
If it exceeds 400% by mass, the resin composition may have a high viscosity or may have a precipitate.

As the known coloring agent, generally, red, green and blue pigments which are constituent colors of a color filter and the like can be used. For example, carmine 6B (C.I.
12490), phthalocyanine green (CI. 74)
260), phthalocyanine blue (CI. 7416)
0), Chromophthal Red A2B, Lionogen Yellow 1010, Monastral Green 6Y, Lionogen Violet RL, carbon black and the like.
The content varies depending on the target chromaticity and the like, but is preferably 2 to 50% by mass of the mass (solid content) of the colored resin composition.

(Binder Polymer) The binder polymer is an alkali-soluble polymer having a carboxylic acid group in a side chain, for example, Japanese Patent Application Laid-Open No. 59-44.
No. 615, JP-B-54-34327, JP-B-58-12577, JP-B-54-25957, JP-A-59-53836, and JP-A-59-53836.
JP-A-71048 discloses methacrylic acid copolymers, acrylic acid copolymers, itaconic acid copolymers, crotonic acid copolymers, maleic acid copolymers, and partially esterified maleic acid copolymers. Further, a cellulose derivative having a carboxylic acid group in a side chain can also be mentioned.

In addition to the above, those obtained by adding a cyclic acid anhydride to a polymer having a hydroxyl group are also suitable. Particularly, a copolymer of benzyl (meth) acrylate and (meth) acrylic acid or a multi-component copolymer of benzyl (meth) acrylate, (meth) acrylic acid and another monomer described in US Pat. No. 4,139,391. Can be mentioned.

When an alkali-soluble binder polymer is used, it is preferable to select and use one having an acid value in the range of 50 to 300 mgKOH / g and a mass average molecular weight in the range of 1,000 to 300,000.

In addition to the above-mentioned alkali-soluble binder polymer, an alkali-insoluble polymer can be added for the purpose of improving various performances, for example, the strength of the cured film, as long as it does not adversely affect developability and the like. Such polymers include alcohol-soluble nylon or epoxy resins.

As described above, since the azaphthalocyanine compound represented by the general formula (1) is contained as a colorant, only the transparency (light transmission) of the colored resin composition itself is excellent. In addition, a colored resin composition having a good blue hue having a high color density and another hue can be obtained. In addition, a sufficient concentration can be ensured even when used in a thin film (layer), and cost reduction can be achieved.

<Colored Photosensitive Composition> The mode of the colored photosensitive composition can be appropriately selected from known ones which can be developed with an aqueous alkali solution or an organic solvent, for example, those described in JP-A-3-282404. All can be used, for example, a photosensitive resin composition comprising a negative type diazo resin and a binder, a photopolymer composition, a photosensitive resin composition comprising an azide compound and a binder, a cinnamic acid type photosensitive resin composition Is mentioned. Among them, a photosensitive composition containing a (alkali-soluble) binder polymer, a monomer having an ethylenically unsaturated double bond that undergoes addition polymerization by light irradiation, and a photopolymerization initiator is preferable. From the viewpoints of pollution prevention and safety, those which can be developed with an alkaline aqueous solution are preferable.

The colored photosensitive composition of the present invention comprises the above-mentioned colored resin composition of the present invention, a polyfunctional monomer having two or more ethylenically unsaturated double bonds, and a photopolymerization initiator. At least it may contain, and if necessary, other components. The binder polymer-containing component includes the colored resin composition of the present invention, and the colored resin composition is as described above.

The colored photosensitive composition of the present invention is a polyfunctional monomer having two or more ethylenically unsaturated double bonds (hereinafter, referred to as a monomer having an ethylenically unsaturated double bond which is addition-polymerized by irradiation with light). "Polymerizable compound"). Examples of the polymerizable compound include compounds having at least two addition-polymerizable ethylenically unsaturated groups in the molecule and having a boiling point of 100 ° C. or more at normal pressure. For example, monofunctional acrylates and monofunctional methacrylates such as polyethylene glycol mono (meth) acrylate, polypropylene glycol mono (meth) acrylate, and phenoxyethyl (meth) acrylate;

Polyethylene glycol di (meth) acrylate, polypropylene glycol di (meth) acrylate, trimethylolethane triacrylate, trimethylolpropane triacrylate, trimethylolpropane diacrylate, neopentyl glycol di (meth) acrylate, pentaerythritol tetra ( (Meth) acrylate, pentaerythritol tri (meth)
Acrylate, dipentaerythritol hexa (meth)
Acrylate, dipentaerythritol penta (meth)
Acrylate, hexanediol di (meth) acrylate, trimethylolpropane tri (acryloyloxypropyl) ether, tri (acryloyloxyethyl) isocyanurate, tri (acryloyloxyethyl) cyanurate, glycerin tri (meth) acrylate; trimethylolpropane and glycerin And polyfunctional acrylates and polyfunctional methacrylates, such as those obtained by adding propylene oxide to ethylene oxide to a polyfunctional alcohol such as (meth) acrylated.

Further, Japanese Patent Publication No. 48-41708, Japanese Patent Publication No. 50-6034, and Japanese Patent Application Laid-Open No. 51-37193.
Urethane acrylates described in JP-A No.
Polyester acrylates described in JP-A-64183, JP-B-49-43191 and JP-B-52-30490; polyfunctional acrylates and methacrylates such as epoxy acrylates which are reaction products of an epoxy resin and (meth) acrylic acid Are also mentioned. Among them, trimethylolpropane tri (meth) acrylate, pentaerythritol tetra (meth) acrylate, dipentaerythritol hexa (meth) acrylate, and dipentaerythritol penta (meth) acrylate are preferable.

The polyfunctional monomer (polymerizable compound) having two or more ethylenically unsaturated double bonds may be used alone or as a mixture of two or more. The content of the polymerizable compound is generally 5 to 50% by mass of the mass (total solid content) of the colored photosensitive composition, and particularly preferably 10 to 40% by mass.
% By mass is preferred. If the content is less than 5% by mass, the photosensitivity and the strength of the image may be reduced. If the content is more than 50% by mass, the adhesiveness of the photosensitive resin layer may be excessive, which is not preferable.

The colored photosensitive composition of the present invention contains a photopolymerization initiator. Examples of the photopolymerization initiator include a vicinal polyketaldonyl compound described in U.S. Pat. No. 2,367,660, an acyloin ether compound described in U.S. Pat. No. 2,448,828, and U.S. Pat.
No. 22512, aromatic acyloin compounds substituted with α-hydrocarbons, US Pat. No. 3,046,127
Quinone compounds described in US Pat. No. 5,295,758 and US Pat. No. 3,549,367, a combination of a triarylimidazole dimer and a p-aminoketone described in US Pat. No. 3,549,367, and JP-B-51-48516. Described benzothiazole compound and trihalomethyl-s-triazine compound, trihalomethyl-s-triazine compound described in U.S. Pat. No. 4,239,850, trihalomethyl oxadiazole compound described in U.S. Pat. No.

Among them, trihalomethyl-s-triazine, trihalomethyloxadiazole and triarylimidazole dimer are particularly preferred. As the content of the photopolymerization initiator, the mass of the colored photosensitive composition (total solid content)
Is generally 0.5 to 20% by mass, and particularly preferably 1 to 15% by mass. When the content is less than 0.5% by mass, light sensitivity and image intensity may be reduced.
Even if added in excess of 0% by mass, no effect on performance improvement is observed.

As described above, since the colored resin composition containing the azaphthalocyanine compound represented by the general formula (1) is used, the transparency (translucency) of the colored photosensitive composition itself is reduced. ) As well as a colored photosensitive composition having a good blue hue with a high color density and other hues. Therefore, it is possible to obtain an optical film (for example, a color filter (filter film) or the like) having high transparency, excellent color density and excellent hue (especially blue) and excellent optical characteristics, and solves the conventional problems. Being a thin film (layer)
It is possible to form a film (layer) (filter film etc.)
Cost reduction can also be achieved.

The colored resin composition and the colored photosensitive composition of the present invention can be adjusted to a desired hue, and include, for example, a color filter used for a color liquid crystal display, an ink for a color printer (inkjet printer), and the like. It can be suitably used for applications such as color copier toner (color toner).

<Color Filter> The color filter of the present invention comprises a filter film in which two or more pixel patterns having different spectral characteristics are arranged adjacent to each other on the same substrate, and the filter film is formed as described above. It is formed using the colored photosensitive composition of the present invention.

In general, a color filter is composed of a red (R), green (G), and blue (B) colored film and, if necessary, a black matrix formed between these colored films. The filter film is formed by a method including a step of forming a colored film (colored film forming step) and, if necessary, a step of forming a black matrix (black matrix forming step). Can be formed. Here, as the colored film forming step and the black matrix forming step, using a photosensitive transfer material having a photosensitive resin layer formed by applying a photosensitive resist on a temporary support, transferred to a substrate, exposure, An embodiment (Embodiment (A)) of forming by developing, or an embodiment [Embodiment (B)] of forming by applying a photosensitive resist on a substrate, exposing and developing. Examples of the photosensitive transfer material include a dry film for forming a pixel and a photosensitive black resin sheet for forming a black matrix.

As the colored film forming step and the black matrix forming step, any one of the above-mentioned modes (A) and (B) may be adopted. Mode (A) and the other step may be mode (B).

In the embodiment (A), a photosensitive transfer material having a photosensitive resin layer in which a colored photosensitive resist material is provided on a temporary support is used, and the photosensitive resin layer is formed on a substrate. After the transfer, the film is exposed to a desired pattern, and further developed to form a colored film. Here, by using a plurality of photosensitive transfer materials each having a photosensitive resin layer of a different hue, by repeatedly transferring, exposing, and developing on the same substrate, two or more photosensitive materials having different spectral characteristics on the same substrate are obtained. Pixel patterns (for example, a filter film made of RGB) can be arranged adjacently.

The photosensitive transfer material has at least a photosensitive resin layer on a temporary support, and a thermoplastic resin layer, if necessary, between the temporary support and the photosensitive resin layer. An intermediate layer such as an oxygen barrier layer is provided. In addition, the photosensitive resin layer, for the purpose of protecting the photosensitive resin layer during storage,
Preferably, a cover film is provided.

<Temporary Support> The temporary support is made of a material that is flexible, has good releasability from the photosensitive resin layer or the like, and is chemically and thermally stable. Is preferred. Specifically, Teflon (registered trademark), polyethylene terephthalate, polycarbonate, polyethylene,
A film such as polypropylene or a laminate thereof is preferred. The thickness of the temporary support is suitably from 5 to 300 μm, and particularly preferably from 20 to 150 μm. On the surface of the temporary support, from the viewpoint of improving the slipperiness and improving the adhesiveness with the photosensitive resin layer, a known fine particle-containing slippery composition,
It is also useful to apply a release agent composition containing a silicone compound.

<Photosensitive Resin Layer> The photosensitive resin layer is a colored layer containing a photosensitive resin composition and a coloring agent, and is preferably a resin layer which is softened or fluidized by heat or pressure. Specifically, it is preferable to have a transferability that shows thermoplasticity having softness or tackiness at a temperature of at least 150 ° C. or less, while curing when irradiated with light,
It is preferable that the unirradiated portion is easily soluble in an alkaline solution and has resist properties. The layer is formed by adding a thermoplastic resin,
Further modification is possible by the addition of compatible plasticizers.

The photosensitive resin layer is particularly preferably a layer containing a photosensitive resin composition and a coloring agent. For example, a coating solution containing at least the photosensitive resin composition and a coloring agent (photosensitive solution) (A coating solution for a conductive resin layer). In the present invention, it can be suitably formed by using the coating solution for a photosensitive resin layer containing at least the colored photosensitive composition of the present invention described above. The photosensitive resin layer may contain the following components in addition to the components contained in the colored photosensitive composition described above.

The photosensitive resin layer preferably contains a thermal polymerization inhibitor. Examples of the thermal polymerization inhibitor include hydroquinone, p-methoxyphenol, di-t
-Butyl-p-cresol, pyrogallol, t-butylcatechol, benzoquinone, 4,4'-thiobis (3-
Methyl-6-t-butylphenol), 2,2′-methylenebis (4-methyl-6-t-butylphenol),
2-mercaptobenzimidazole, phenothiazine and the like. Further, known additives such as a plasticizer, a surfactant, a solvent, and the like can be added to the photosensitive resin layer.

The photosensitive transfer material is prepared by dissolving (or dispersing) the above-described colored photosensitive composition of the present invention in a solvent on a temporary support (a coating solution for a photosensitive resin layer). Is applied on a temporary support by a known coating method and then dried. Generally, the thickness of the photosensitive resin layer is preferably 0.5 to 3 μm,
Usually, it is about 2 μm.

Further, when a thermoplastic resin layer or an intermediate layer (such as an oxygen barrier layer) is provided, first, a coating liquid (a coating liquid for a thermoplastic resin layer) formed by dissolving a thermoplastic resin in an organic solvent is temporarily supported. Coating and drying on the body to form a thermoplastic resin layer, then preparing a coating solution (a coating solution for an intermediate layer) using a solvent that does not dissolve the thermoplastic resin layer, and coating and drying the intermediate layer Are laminated. Next, a coating solution for a photosensitive resin layer using an organic solvent that does not dissolve the intermediate layer is prepared, and further applied and dried on the intermediate layer to form a photosensitive resin layer. A cover film made of polypropylene or the like may be further provided on the surface of the photosensitive resin layer. The cover film is peeled off in a step before the photosensitive transfer material is laminated on the substrate.

<Thermoplastic resin layer> The thermoplastic resin layer is provided for the purpose of preventing air bubbles from entering during transfer, and mainly contains an alkali-soluble thermoplastic resin, and may contain other components as necessary. May be included. The thermoplastic resin preferably has a substantial softening point of 80 ° C. or less. Examples of the alkali-soluble thermoplastic resin having a softening point of 80 ° C. or lower include a saponified product of ethylene and an acrylate copolymer, a saponified product of styrene and a (meth) acrylate copolymer, and vinyltoluene and (meth) acrylic. Examples include saponified acid ester copolymers, poly (meth) acrylates, and saponified (meth) acrylate copolymers such as butyl (meth) acrylate and vinyl acetate. The thermoplastic resins may be used alone or in combination of two or more.

Further, organic materials having a softening point of about 80 ° C. or lower described in “Plastic Performance Handbook” (edited by the Japan Plastics Industry Federation, All Japan Plastics Molding Federation, published by the Industrial Research Institute, issued on October 25, 1968) Among the polymers, those soluble in an alkaline aqueous solution can be used.

Further, even if the organic polymer substance has a softening point of 80 ° C. or higher, various plasticizers compatible with the organic polymer substance are added to the organic polymer substance to substantially reduce the organic polymer substance. The softening point can be lowered to 80 ° C. or lower.
In the organic polymer substance, various polymers, a supercooled substance, an adhesion improver, a surfactant, a releasing agent, for the purpose of adjusting the adhesive strength to the support, within a range where the substantial softening point does not exceed 80 ° C. Molding agents and the like can be added.

Specific examples of the plasticizer include polypropylene glycol, polyethylene glycol, dioctyl phthalate, diheptyl phthalate, dibutyl phthalate, tricresyl phosphate, cresyl diphenyl phosphate, biphenyl diphenyl phosphate, and the like. .

The thermoplastic resin layer is prepared by dissolving the thermoplastic resin and, if necessary, other components in an organic solvent to prepare a coating solution (coating solution for the thermoplastic resin layer), and temporarily supporting the coating solution by a known coating method. It can be formed by coating or the like on the body. Examples of the organic solvent include methyl ethyl ketone, 1-methoxy-
2-propanol and the like.

The thickness of the thermoplastic resin layer is 6 μm.
m or more is preferable. When the layer thickness is less than 6 μm, 1
In some cases, it may be difficult to completely absorb irregularities of the underlayer having a size of μm or more. The upper limit is generally about 100 μm or less from the viewpoint of developability and manufacturing suitability, and about 50 μm or less.
m or less is preferable.

<Intermediate Layer> It is preferable to provide an oxygen barrier layer or the like as the intermediate layer. The oxygen barrier layer, the purpose of preventing the diffusion of oxygen from the air that inhibits the photo-curing reaction in the photosensitive resin layer during pattern exposure, and the layer when the thermoplastic resin layer is provided It is provided for the purpose of preventing the photosensitive resin layer from mixing with each other.

The oxygen barrier layer is mainly composed of a resin component which can be dispersed and dissolved in water or an aqueous alkali solution, and may contain other components such as a surfactant, if necessary. The resin component constituting the oxygen barrier layer can be appropriately selected from known ones.
No. 121 and JP-B-56-40824, polyvinyl ether / maleic anhydride polymer, water-soluble salts of carboxyalkyl cellulose, water-soluble cellulose ethers, water-soluble salts of carboxyalkyl starch, polyvinyl alcohol, polyvinyl pyrrolidone, Water-soluble salts of the group consisting of various polyacrylamides, various water-soluble polyamides, water-soluble salts of polyacrylic acid, gelatin, ethylene oxide polymers, various starches and the like, styrene / maleic acid copolymers, maleates Resins and those obtained by combining two or more of these resins are exemplified.

Among them, a combination of polyvinyl alcohol and polyvinyl pyrrolidone is particularly preferred. Further, the polyvinyl alcohol has a saponification rate of 80.
% Or more is preferable. The content of the polyvinyl pyrrolidone is 1 to 75% of the solid volume of the intermediate layer.
Is preferable, more preferably 1 to 60%, and most preferably 10 to 50%. If the solid volume is less than 1%, sufficient adhesion with the curable resin layer may not be obtained, and if it exceeds 75%,
Oxygen barrier ability may decrease.

When the oxygen-blocking ability of the oxygen-blocking layer is lowered, the polymerization sensitivity of the curable resin layer is lowered, so that it is necessary not only to increase the amount of light during exposure or to lengthen the exposure time, but also to increase the resolution. Therefore, the oxygen permeability is preferably small.

The oxygen barrier layer is formed by dissolving and dispersing a resin component and the like in an aqueous solvent to prepare a coating solution (coating solution for an oxygen barrier layer) and applying the solution on a temporary support by a known coating method. can do. Examples of the aqueous solvent include a solvent containing water such as distilled water as a main component and, if desired, a solvent or a salt having an affinity for water, such as alcohol, to the extent that the effects of the present invention are not impaired.

The thickness of the oxygen barrier layer is about 0.1
To 5 μm, more preferably 0.5 to 2 μm.
If the layer thickness is less than about 0.1 μm, the oxygen permeability is too high, and the polymerization sensitivity of the curable resin layer may be lowered. It may be necessary.

<Conductive layer etc.> The above-mentioned temporary support is peeled off after the photosensitive resin layer of the photosensitive transfer material is laminated on the substrate constituting the color filter. At this time, the film and the human body are charged. As a result, unpleasant electric shock may be caused, and dust may be attracted from the surroundings due to charging. As a result, an unexposed portion may be generated at the time of exposure, which may cause a pinhole. Therefore, in order to prevent electrification, a conductive layer is provided on at least one surface of the temporary support so that its surface electric resistance is 10 ¹³ Ω or less, or as a temporary support, conductivity is imparted to itself. It is preferable to use one having a surface electric resistance of 10 ¹³ Ω or less.

A method for imparting conductivity to the temporary support is described in JP-A-8-171201, paragraph [003].
1] to [0044] can be referred to. In order to prevent electrostatic shock due to charging, the surface electric resistance of the conductive layer or the substrate provided with conductivity should be 10 ¹³ Ω
The following is desirable, and 10 ¹² Ω or less is particularly preferable.

<Method of Forming Filter Film> Next, a method of forming a filter film using a photosensitive transfer material will be described. Here, an example using a photosensitive transfer material in which a thermoplastic resin layer, an oxygen blocking layer, a photosensitive resin layer, and a cover film are laminated in this order on a temporary support as a photosensitive transfer material is shown. First, the cover film of the photosensitive transfer material is removed, and the photosensitive resin layer is closely adhered to a substrate as a transfer object under pressure and heat. For the lamination, a conventionally known laminator, a material appropriately selected from vacuum laminators and the like can be used, and in order to further increase the productivity,
An auto cut laminator can also be used.

After laminating, the temporary support is peeled off at the interface with the thermoplastic resin layer, and the photosensitive resin layer is exposed in a pattern from above the thermoplastic resin layer through the thermoplastic resin layer and the oxygen barrier layer ( Patterning). As a light source that can be used for the patterning, a light source that emits ultraviolet light is preferable in terms of high energy and rapid polymerization reaction, and examples thereof include a high-pressure mercury lamp, an ultra-high-pressure mercury lamp, a metal halide lamp, and an Hg-Xe lamp.

As the patterning method, for example, a method of arranging an exposure mask above the thermoplastic resin layer and exposing the pattern in a lump through the mask, a method of using an exposure means such as a stepper exposure device, or the like is used. No.

After the exposure, development processing is performed to remove the thermoplastic resin layer, the oxygen blocking layer, and the unnecessary portion (uncured portion) of the photosensitive resin layer. Then, only the irradiated cured portion remains on the substrate to form a filter film. By repeating this process using a photosensitive transfer material for forming a red, green, and blue colored film, a filter film made of RGB can be formed.

The development can be carried out by a known method. For example, (a) immersing the exposed substrate itself in a developing bath using a solvent or an aqueous developer, particularly an alkaline aqueous solution, etc .; Spraying may be performed on the subsequent substrate by spraying or the like, and if necessary, the object may be rubbed with a rotary brush or a wet sponge or the like while irradiating an ultrasonic wave for the purpose of enhancing the solubility.

As the alkaline aqueous solution, a dilute aqueous solution of an alkaline substance is preferable, and an aqueous solution to which a small amount of a water-miscible organic solvent is added can also be suitably used. As the alkaline substance, sodium hydroxide,
Alkali metal hydroxides such as potassium hydroxide; alkali metal carbonates such as sodium carbonate and potassium carbonate; alkali metal bicarbonates such as sodium hydrogen carbonate and potassium hydrogen carbonate; alkali metals such as sodium silicate and potassium silicate Silicates, alkali metal metasilicates such as sodium metasilicate, potassium metasilicate, etc., tetraalkylammonium hydroxides such as triethanolamine, diethanolamine, monoethanolamine, morpholine, tetramethylammonium hydroxide, trisodium phosphate, etc. Is mentioned.

The concentration of the alkaline substance in the alkaline aqueous solution is preferably 0.01 to 30% by weight,
Is preferably 8 to 14.

Examples of the water-miscible organic solvent include:
Methanol, ethanol, 2-propanol, 1-propanol, butanol, diacetone alcohol, ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, ethylene glycol mono n-butyl ether, benzyl alcohol, acetone, methyl ethyl ketone, cyclohexanone, ε-caprolactone,
γ-butyrolactone, dimethylformamide, dimethylacetamide, hexamethylphosphoramide, ethyl lactate, methyl lactate, ε-caprolactam, N-methylpyrrolidone and the like. As the addition amount of the organic solvent,
0.1 to 30% by weight is preferred.

Further, various known surfactants can be added to the aqueous alkali solution. The concentration of the surfactant is preferably from 0.01 to 10% by weight. Usually, the temperature during development is preferably from about room temperature to 40 ° C.
Further, after the development processing, a step of washing with water may be included.

In the above embodiment (B), a colored photosensitive resist material (having the same composition as the photosensitive resin layer coating solution prepared in the above embodiment (A)) is directly applied onto a substrate. In the same manner as in the embodiment (A), a filter film is formed by exposing to a desired pattern and further developing. Here, a filter film made of RGB can be formed by repeatedly applying, exposing, and developing on the same substrate using the photosensitive resin layer coating solutions having different hues. The conditions relating to exposure and development, such as the photosensitive resin layer coating solution, the coating thickness of the coating solution, the substrate, and preferred embodiments thereof, used in this embodiment are the same as those in the above embodiment (A).

When a black matrix is formed (black matrix step), a black pattern containing a resin is formed in the peripheral region of the colored film. In the aspect (A), a black photosensitive transfer material having a black colored photosensitive resin layer in which a black colored photosensitive resist material is provided on a temporary support is used. It can be formed by performing transfer, exposure and development processing on the above. The black-colored photosensitive resin layer can be formed by a coating solution (a coating solution for a black matrix) containing at least a photosensitive resin composition and a black colorant.
Black pigments are commonly used, such as carbon black. In the above aspect (B), a black colored photosensitive resist material (having the same composition as the black matrix coating solution prepared in the above aspect (A)) is directly applied onto a substrate, The pattern can be formed by exposing and developing.

As a substrate constituting a color filter,
For example, a known glass plate such as a soda glass plate, a low expansion glass plate, a non-alkali glass plate, and a quartz glass plate having a silicon oxide film on the surface thereof, or a plastic film may be used.

As described above, the color filter of the present invention
Since it is obtained using the colored photosensitive composition containing the azaphthalocyanine compound described above, it is particularly excellent in optical properties. That is, the filter film is formed using a colored photosensitive composition having a main absorption having a large extinction coefficient near a wavelength of 550 nm and exhibiting a good blue hue having a high color density and another hue. It has excellent transparency (light transmission), excellent hue (especially blue), and sufficient color density, and can display a clear image excellent in spectral characteristics and display contrast.

[0088]

EXAMPLES The present invention will be described below with reference to examples, but the present invention is not limited to these examples. still,
“Parts” and “%” in the examples all represent “parts by mass” and “% by mass”.

(Example 1) -Preparation of coating solution A- 0.25 parts of an azaphthalocyanine compound according to the present invention (example compound (1) described above), 1,3-dimethyl-2-imidazolidinone 5 parts, methyl ethyl ketone 2.75
Part, a methacrylic acid / benzyl methacrylate copolymer (molar ratio 28/72, average molecular weight 30,000; 40% 1-methoxy-2-propyl acetate solution) was mixed and stirred, and then the insoluble portion was removed by filtration. Coating liquid A was obtained.

-Coating Sample- A 2.0 cm part of the coating liquid A obtained above was coated on the surface of a glass plate of 10 cm × 10 cm using a spin coater (1H-DX2, manufactured by Mikasa Corporation) (at 300 rpm). , 3
0 seconds). Then, it dried at 85 degreeC for 30 minutes, and produced the coating sample (1).

(Examples 2 to 8) Instead of the azaphthalocyanine compound used in Example 1, the above-mentioned exemplified compounds (2) to (2) were used.
(8) Coated sample (2) in the same manner as in Example 1 except that (azaphthalocyanine compound) was used, respectively.
To (8).

Comparative Examples 1 to 3 The following comparative compounds (A) to (A) were used in place of the azaphthalocyanine compound used in Example 1.
Comparative coating samples (9) to (11) were produced in the same manner as in Example 1 except that (C) was used.

[0093]

Embedded image

(Evaluation) Coated sample (1) obtained above
Spectrophotometer (UV-2400, Shimadzu Corporation) for (8) and comparative coated samples (9) to (11)
The transmission spectrum was measured using
Was determined. The measurement results are shown in Table 1 below.
Shown in

[0095]

[Table 1]

From the results shown in Table 1, the coated samples (1) to (8) containing the azaphthalocyanine compound according to the present invention were obtained.
Showed that the optical transmittance was high and good optical characteristics were obtained. On the other hand, the coated samples (9) to (11) of Comparative Examples in which the azaphthalocyanine compound was not used had poor transparency.

(Example 9)-Preparation of photosensitive transfer material-A polyethylene terephthalate film (PET film) having a thickness of 100 µm was prepared as a temporary support.
A coating solution having the following formulation H1 was applied to the surface of the T film and dried to form a thermoplastic resin layer having a dry layer thickness of 20 μm.

[Formulation H1 of Coating Solution for Thermoplastic Resin Layer] Methyl methacrylate / 2-ethylhexyl acrylate / benzyl methacrylate / methacrylic acid copolymer: 15 parts (copolymerization ratio (molar ratio) = 55 / 28.8) /11.7/4.5, weight average molecular weight = 90000)-Polypropylene glycol diacrylate ... 6.5 parts (average molecular weight 822)-Tetreethylene glycol dimethacrylate ... 1.5 parts-p-Toluenesulfonamide ... 0. 5 parts ・ Benzophenone ... 1.0 parts ・ Methyl ethyl ketone ... 30 parts

Next, an intermediate layer coating solution having the following formulation B1 was applied on the thermoplastic resin layer and dried to form an intermediate layer having a dry layer thickness of 1.6 μm. [Formulation B1 of coating solution for intermediate layer]-Polyvinyl alcohol ... 130 parts (PVA205, saponification rate = 80%, manufactured by Kuraray Co., Ltd.)-Polyvinylpyrrolidone ... 60 parts (PVP, K-90, manufactured by GAF Corporation)・ Fluorine surfactant: 10 parts (Surflon S-131, manufactured by Asahi Glass Co., Ltd.) ・ Distilled water: 3350 parts

As described above, four temporary supports on which the thermoplastic resin layer and the intermediate layer were formed were prepared, and black (for the K layer) and red having the following formulation were formed on each intermediate layer. (For R layer), green (for G layer) or blue (for B layer) any one of the photosensitive resin layer coating liquids is applied and dried to obtain a dry layer thickness of 2
A photosensitive resin layer having a thickness of μm was formed.

[0101]

[Table 2]

Further, a cover sheet of polypropylene (thickness: 12 μm) was pressed on the photosensitive resin layers of each color to obtain four colors of red, blue, green and black photosensitive transfer materials.

Using the photosensitive transfer material obtained as described above, a color filter was produced by the following method. First, the coating sheet of the red photosensitive transfer material is peeled off, and the surface of the photosensitive resin layer is applied to a transparent glass substrate (thickness: 1.1 mm) using a laminator (VP-II, manufactured by Taisei Laminator Co., Ltd.). Lamination was performed under pressure (0.8 kg / cm ² ) and heating (130 ° C.). Subsequently, the temporary support was peeled off at the interface with the thermoplastic resin layer, and the temporary support was removed.

Next, exposure was performed through a predetermined photomask, and development was performed with a 1% aqueous sodium carbonate solution to remove unnecessary portions, thereby forming a red pixel pattern on a transparent glass substrate.
Subsequently, a green photosensitive transfer material is adhered to the transparent glass substrate on which the red pixel pattern is formed in the same manner as described above,
Further, peeling, exposure and development were performed to form a green pixel pattern. The same operation was repeated using blue and black photosensitive transfer materials to produce a color filter.

In the obtained color filter, the wavelength 4 of the blue pixel pattern was measured in the same manner as in Example 1.
The transmittance at 50 nm was 94%, the light transmittance was high, the hue (purity) of blue was excellent, and excellent spectral characteristics and display contrast were exhibited.

(Comparative Example 4) In Example 9, the comparative compound (C) was used in place of the azaphthalocyanine compound (exemplified compound (1)) used for producing the blue photosensitive transfer material.
A color filter of a comparative example was produced in the same manner as in Example 9, except that was used. The blue light transmittance of the obtained color filter was 86% at a wavelength of 450 nm, which was inferior in transparency, and the blue hue was also lower than that of the color filter obtained in Example 9. Was inferior.

[0107]

According to the present invention, a colored resin composition and a colored photosensitive composition containing a dye as a coloring agent, having excellent transparency (light transmission), good color density and good hue (especially blue). Can be provided. In addition, it is particularly excellent in transparency (light transmission) and hue (especially blue), and has high concentration (especially blue) even in a thin film.
And a color filter having excellent optical characteristics can be provided at low cost.

──────────────────────────────────────────────────の Continued on the front page (51) Int.Cl. ⁷ Identification symbol FI Theme coat ゛ (Reference) C08K 5/3445 C08K 5/3445 4J026 C09B 47/00 C09B 47/00 G02B 5/20 101 G02B 5/20 101 G02F 1/1335 505 G02F 1/1335 505 G03F 7/004 505 G03F 7/004 505 F term (reference) 2H025 AA00 AB13 AC01 AD01 BC13 BC42 CA00 CB42 CC12 FA17 2H048 BA02 BA45 BA48 BB02 BB14 BB15 BB42 2H091 FA02 4J002 AB011 BG011 BH021 EU026 EU106 FD096 GP00 4J011 PA43 PA53 PA69 PA70 PB25 PC02 PC08 4J026 AA02 AA43 AA44 AA53 BA27 BA28 BA29 BA50 BB01 BB02 DB06 DB36 GA06

Claims (4)

[Claims] 1. A colored resin composition comprising at least a binder polymer and a coloring agent, wherein at least one of the coloring agents is a compound represented by the following general formula (1). Embedded image [In the general formula (1), R ¹ , R ² , R ³ , R ⁴ , R ⁵ , R ⁶ , R
⁷ and R ⁸ are each independently a hydrogen atom, an alkyl group, a hydroxyl group, an alkoxy group, an amino group, an alkylamino group, a dialkylamino group, a halogen atom, a sulfonic acid group, a sulfonic acid salt, a carboxylic acid group, and a carboxylic acid salt. , An ester group or an amide group, which may be the same or different. A ¹ , A ² , A ³ , A ⁴ , A ⁵ , A ⁶ , A ⁷ and A ⁸ each independently represent N or CH, and may be the same or different, and at least ^{one of} A ^{1 to} A ⁸ One represents N. ] 2. The colored resin composition according to claim 1, wherein the binder polymer is a binder polymer having an acidic group. 3. A coloring comprising the colored resin composition according to claim 1 or 2, a polyfunctional monomer having two or more ethylenically unsaturated double bonds, and a photopolymerization initiator. Photosensitive composition. 4. A color filter comprising a filter film in which two or more pixel patterns having different spectral characteristics are arranged adjacently on the same substrate, wherein the filter film is:
A color filter formed using the colored photosensitive composition according to claim 3.