JP2002241640A - Pigment-dispersing composition, colored photosensitive composition using the same and color filter - Google Patents

Abstract

PROBLEM TO BE SOLVED: To provide a pigment-dispersing composition excellent in dispersibility and color tone, in which a color filter can keep stably good display characteristic when used for preparation of the color filter. SOLUTION: This pigment-dispersing composition is obtained by dispersing a dispersing agent, a pigment and a resin into an organic solvent. The pigment- dispersing composition is characterized in that the sum of sodium ion and potassium ion contents obtained by an atomic absorption method is <10,000 ppm. In the composition, water content in the dispersing agent is preferably <=10 wt.% based on total weight.

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

The present invention relates to a pigment dispersion composition,
The present invention relates to a colored photosensitive composition and a color filter using the same.

[0002]

2. Description of the Related Art Conventionally, pigments have been widely used in many fields such as paints, printing inks, color display boards, etc., because they exhibit a vivid color tone and high coloring power. Further, since the photosensitive composition containing a pigment can form an image having a clear color tone by light irradiation, for example, formation of a multicolor image on a substrate such as a color proof, and color formation of a liquid crystal color display or the like Widely used as a filter material. In such various uses, the pigment is usually used as a pigment dispersion composition dispersed in a medium such as an organic solvent.
Since the dispersibility of the pigment-dispersed particles in the composition affects the coloring power, color tone, light transmittance, and the like of the composition, the pigment-dispersed composition is used for the purpose of improving the dispersibility of the pigment. Often a dispersant is added.

[0003]

By the way, a color filter is one in which pixels of three colors of red (R), green (G) and blue (B) are arranged in a line or mosaic on a substrate. The pixels of the color filter are required to have a desired color tone and light transmittance, and are required not to hinder the electrical drive control of the liquid crystal display device. However, when a pixel is made of a pigment, inorganic ions which are impurities of the pigment may adversely affect the display characteristics of the liquid crystal display device. One of the causes is that the inorganic ions contained in the pixels of the color filter are eluted into the liquid crystal cell over time or due to the voltage stress of driving the liquid crystal. Inorganic ions eluted into the liquid crystal cell have an adverse effect on driving of the liquid crystal, and display characteristics may be degraded. For example, Japanese Patent Application Laid-Open No. H11-138213 discloses that display characteristics are improved by reducing the amount of bromine ion impurities in a pigment constituting a pixel of a color filter. However, the influence of components other than the pigment contained in the pigment dispersion composition on the display characteristics has not been studied so far.

[0004] The present inventors have studied the effects of components other than pigments on the display characteristics and the like of the pigment dispersion composition, and found that impurities in the dispersant adversely affect the display characteristics of the prepared color filter. In addition, the amount of water in the dispersant greatly affects the physical properties of the obtained pigment dispersion composition, and adversely affects the color tone and light transmittance of a color filter (or colored photosensitive composition) using the composition. I found that.

[0005] It is an object of the present invention to provide a pigment dispersion composition which is excellent in dispersibility and color tone, and in particular, when used for producing a color filter, the color filter can stably maintain good display characteristics. I do. Further, the present invention can form an image having a clear color tone and high light transmittance,
In particular, it is an object of the present invention to provide a colored photosensitive composition in which the color filter can stably maintain good display characteristics when used for producing a color filter. Another object of the present invention is to provide a color filter having a clear color tone and high light transmittance, and capable of stably maintaining good display characteristics.

[0006]

Means for solving the above problems are as follows. <1> A pigment dispersion composition obtained by dispersing a dispersant, a pigment, and a resin in an organic solvent, wherein the total content of sodium ions and potassium ions of the dispersant obtained by an atomic absorption method is less than 10,000 ppm. And a pigment dispersion composition.

<2> The pigment dispersion composition according to <1>, wherein the water content in the dispersant is 10% by mass or less based on the total mass of the dispersant. <3> The pigment dispersion composition according to <1> or <2>, wherein the resin is a polymer having an acidic group. <4> The pigment dispersion composition according to any one of <1> to <3>, wherein the dispersant is a compound represented by the following general formula (I).

[0008]

Embedded image

In the general formula (I), A represents a component capable of forming an azo dye together with XY. X represents a single bond or a group selected from divalent linking groups represented by the following structural formulas. Y represents a group represented by the following general formula (II).

[0010]

Embedded image

[0011]

Embedded image

In the general formula (II), Z represents a lower alkylene group. -NR ₂ represents a 5- or 6-membered saturated heterocyclic group containing a lower alkylamino group, or a nitrogen atom. a is
Represents 1 or 2.

<5> Any one of the above <1> to <4>
A colored photosensitive composition comprising: the pigment dispersion composition described in item 1; a polyfunctional monomer having two or more ethylenically unsaturated double bonds; and a photopolymerization initiator. <6> A color filter having two or more patterned colored layers having different hues on a substrate, wherein the colored layer is made of the colored photosensitive composition according to <5>. Color filter.

[0014]

BEST MODE FOR CARRYING OUT THE INVENTION Hereinafter, the present invention will be described in detail. <Pigment dispersion composition> The pigment dispersion composition of the present invention is obtained by dispersing a dispersant, a pigment and a resin in an organic solvent. The dispersant has a total content of sodium ions and potassium ions determined by an atomic absorption method of less than 10,000 ppm, preferably 500 ppm or less. Incidentally, the content of sodium ions and potassium ions in the dispersant,
Atomic absorption method (according to the method generally called dry method)
Can be measured. The sum of the contents is 1
If the amount is 0000 ppm or more, the dispersibility and the color tone are deteriorated, and particularly, the display characteristics of the produced color filter are deteriorated.

The water content in the dispersant is as follows:
It is preferably at most 10% by mass of the total mass of the dispersant, more preferably at most 3% by mass. In addition, it is desirable that the lower limit be as low as possible. The water content was determined by sampling 3 g of a dispersant as a sample in an aluminum dish, drying it at 105 ° C. overnight, and subtracting the mass (g) of the obtained product from the total mass (3 g) of the sample. It can be determined by calculating the ratio (% by mass) of the obtained value (difference) to the total mass (3 g) of the sample before drying. When the water content in the dispersant exceeds 10% by mass, the viscosity of the pigment dispersion composition becomes high, making it difficult to control the viscosity, and also when producing a color filter, a clear color tone and high transmittance. May be difficult to maintain.

The pigment dispersion composition of the present invention is excellent in color tone because it contains a pigment, and also excellent in dispersibility because it contains a dispersant. Furthermore, since the amount of impurities of the alkali ions contained in the dispersant is reduced, the color filter can stably maintain good display characteristics especially when used for producing a color filter.

The dispersant can be used by selecting from various materials, provided that the content of sodium ions and potassium ions is within the above range. Specifically, amide compounds such as nonanoamide, decanamide, dodecaneamide, N-dodecylhexadecaneamide, N-octadecylpropioamide, N, N-dimethyldodecaneamide and N, N-dihexylacetamide;
Amine compounds such as diethylamine, diheptylamine, dibutylhexadecylamine, N, N, N ', N'-tetramethylmethanamine, triethylamine, tributylamine and trioctylamine, monoethanolamine, diethanolamine, triethanolamine, N ,
N, N ', N'-(tetrahydroxyethyl) -1,2
-Diaminoethane, N, N, N'-tri (hydroxyethyl) -1,2-diaminoethane, N, N, N ', N
'-Tetra (hydroxyethylpolyoxyethylene)-
Amines having a hydroxy group such as 1,2-diaminoethane, 1,4-bis (2-hydroxyethyl) piperazine and 1- (2-hydroxyethyl) piperazici, and other compounds such as pecotamide, isonipecotamide, nicotinamide and the like. Known dispersants. They are,
It may be a commercially available product, or may be a suitably synthesized product. Examples of the commercially available product include Shigenox-105.
(Trade name, manufactured by Hakkor Chemical Co., Ltd.).

As the dispersant used in the present invention, a compound represented by the following general formula (I) is preferable. When the dispersant is used, the dispersant is adsorbed on the surface of the pigment particles by the nitrogen atom of the dispersant, the surface of the pigment particles is covered with the dispersant, and the adsorption of the pigment particles to each other is suppressed. However, the pigment particles hardly aggregate. As a result, the pigment particles are uniformly dispersed in a finely divided state, and the dispersibility of the pigment is particularly improved.

[0019]

Embedded image

In the general formula (I), A represents a component capable of forming an azo dye together with XY. A can be arbitrarily selected as long as it is a group derived from a compound capable of forming an azo dye by coupling with a diazonium compound. Hereinafter, specific examples of the above A are shown, but the present invention is not limited to these specific examples.

[0021]

Embedded image

[0022]

Embedded image

In the general formula (I), X represents a single bond (meaning that Y is directly connected to -N = N-) or a divalent linking group represented by the following structural formula. Represents a group to be selected.

[0024]

Embedded image

In the above general formula (I), Y represents the following general formula (I
Represents a group represented by I).

[0026]

Embedded image

In the general formula (II), Z represents a lower alkylene group. Z is represented by — (CH ₂ ) _b —, where b is 1 to 5
And preferably represents 2 or 3. General formula (II)
Among, -NR ₂ represents a 5- or 6-membered saturated heterocyclic group containing a lower alkylamino group, or a nitrogen atom. The -NR
If _2, which represents a lower alkylamino group, -N (C _n H
_{2n + 1} ) ₂ , where n represents an integer of 1 to 4, and preferably represents 1 or 2. On the other hand, when -NR ₂ represents a 5- or 6-membered saturated heterocyclic group containing a nitrogen atom, a heterocyclic group represented by the following structural formula is preferable.

[0028]

Embedded image

In the general formula (II), Z and —NR ₂
May each have a lower alkyl group or an alkoxy group as a substituent. In the general formula (II), a represents 1
Or 2 and preferably 2.

Hereinafter, specific examples (exemplary compounds 1 to 22) of the compound represented by the general formula (I) are shown, but the present invention is not limited to these specific examples.

[0031]

Embedded image

[0032]

Embedded image

[0033]

Embedded image

[0034]

Embedded image

Along with the compound represented by the above general formula (I), JP-A No. 2000-239554 describes 0038
It is preferable to use in combination the amine compound represented by the general formula (III) and / or the amine compound represented by the general formula (IV) described in Columns to 0043. The compound represented by the general formula (I) can be synthesized according to the method described in columns 0033 to 0035 of JP-A-2000-239554. As the compound represented by the general formula (I), commercially available products may be used. For example, “Solsperse 22000” and “Solsperse” manufactured by Abina
50,000 ”and“ EFKA-74 ”manufactured by Efka Chemical.
5 "and the like.

When the total content of sodium ions and potassium ions of a commercially available dispersant or a synthesized dispersant exceeds the above range, the dispersant is subjected to washing treatment such as hot water washing and / or water washing. By removing the ions, the total content can be reduced to the above range.

The preferred range of the content of the dispersant in the pigment dispersion composition of the present invention also varies depending on the type of the dispersant used, but is generally 0.1 to 100 parts by mass per 100 parts by mass of the pigment. And preferably 1 to 3 parts.
More preferably, it is 0 parts by mass. It is preferable that the content is within the above range, since the viscosity of the pigment dispersion composition is prevented from excessively increasing and the chromaticity can be easily adjusted at the time of producing a color filter or the like.

As the pigment that can be used in the pigment dispersion composition of the present invention, an organic pigment can be used. Examples of the organic pigment include a yellow pigment, an orange pigment, a red pigment, a violet pigment, a blue pigment, a green pigment, a brown pigment, a black pigment, and the like.

Examples of the yellow pigment include C.I. I.
Pigment Yellow 20, C.I. I. Pigment Yellow 24, C.I. I. Pigment Yellow 12, C.I. I. Pigment Yellow 17, C.I. I. Pigment Yellow 8
3, C.I. I. Pigment Yellow 86, C.I. I. Pigment Yellow 93, C.I. I. Pigment Yellow 10
9, C.I. I. Pigment yellow 110, C.I. I. Pigment Yellow 117, C.I. I. Pigment Yellow 1
25, C.I. I. Pigment yellow 137, C.I. I. Pigment yellow 138, C.I. I. Pigment Yellow 139, C.I. I. Pigment Yellow 185, C.I. I.
Pigment yellow 147, C.I. I. Pigment yellow 148, C.I. I. Pigment Yellow 150, C.I. I
Pigment yellow 153, C.I. I. Pigment yellow, C.I. I. Pigment yellow 154, C.I. I. Pigment yellow 166, C.I. I. Pigment Yellow 1
68, C.I. I. Pigment Yellow 185 and the like.

Examples of the orange pigment include C.I.
I. Pigment Orange 36, C.I. I. Pigment Orange 43, C.I. I. Pigment Orange 51, C.I. I.
Pigment Orange 55, C.I. I. Pigment Orange 59, C.I. I. Pigment Orange 61, C.I. I. Pigment Orange 71, and the like.

Examples of the red pigment include C.I. I.
Pigment Red 9, C.I. I. Pigment Red 97,
C. I. Pigment Red 122, C.I. I. Pigment Red 123, C.I. I. Pigment Red 149, C.I.
I. Pigment Red 168, C.I. I. Pigment Red 177, C.I. I. Pigment Red 180, C.I. I.
Pigment Red 192, C.I. I. Pigment Red 2
15, C.I. I. Pigment Red 216, C.I. I. Pigment Red 217, C.I. I. Pigment Red 22
0, C.I. I. Pigment Red 223, C.I. I. Pigment Red 224, C.I. I. Pigment Red 226,
C. I. Pigment Red 227, C.I. I. Pigment Red 228, C.I. I. Pigment Red 240, C.I.
I. Pigment Red 242, C.I. I. Pigment Red 48: 1, C.I. I. Pigment Red 209, C.I.
I. Pigment Red 146, C.I. I. Pigment Red 11, C.I. I. Pigment Red 81, C.I. I. Pigment Red 213, C.I. I. Pigment Red 27
2, C.I. I. Pigment Red 270, C.I. I. Pigment Red 255, C.I. I. Pigment Red 264,
C. I. Pigment Red 254, and the like.

Examples of the violet pigment include:
C. I. Pigment Violet 19, C.I. I. Pigment Violet 23, C.I. I. Pigment Violet 29, C.I. I. Pigment Violet 30, C.I.
I. Pigment Violet 37, C.I. I. Pigmented Violet 40, C.I. I. Pigment Violet 5
0 and the like.

Examples of the blue pigment include C.I. I.
Pigment Blue 15, C.I. I. Pigment Blue 1
5: 6, C.I. I. Pigment Blue 22, C, I.P. Pigment Blue 60, C.I. I. Pigment Blue 64, and the like.

Examples of the green pigment include C.I. I.
Pigment Green 7, C.I. I. Pigment Green 3
6, etc. Examples of the brown pigment include C.I. I. Pigment Brown 23, C.I. I. Pigment Brown 25, C.I. I. Pigment Brown 26,
And the like. Examples of the black pigment include C.I.
I. Pigment Black 7, and the like.

These pigments may be used alone or in combination of two or more. In the present invention, among these, pigments having an acidic group such as Pigment Yellow 138, Pigment Yellow 139, Pigment Yellow 185, and Pigment Yellow 83 are preferable,
Pigment Yellow 138, Pigment Yellow 13
9, Pigment Yellow 185, Pigment Red 25
4, Pigment Green 36, Pigment Blue 15 and the like are particularly preferred.

The preferred range of the pigment content in the pigment dispersion composition of the present invention varies depending on the type used, but is generally preferably from 5 to 80% by mass, and more preferably from 10 to 80% by mass.
70 mass% is more preferable. It is preferable that the content is within the above range, since it is possible to prevent the viscosity from excessively increasing while maintaining a high coloring power.

As a resin usable in the pigment dispersion composition of the present invention, a polymer having an acidic group is preferable. When a polymer having an acidic group is used as the resin, steric repulsion can be imparted, the dispersion stability of the pigment is improved, and alkali developability when used as a colored photosensitive composition is improved. . Examples of the polymer having an acidic group include a copolymer of (meth) acrylic acid and a (meth) acrylate, a styrene / maleic anhydride copolymer, and a styrene / maleic anhydride copolymer and an alcohol. And the like. These may be used alone or in combination of two or more. Among them, pigment dispersibility is excellent, when used as a colored photosensitive composition, polyfunctional monomer, excellent compatibility with photopolymerization initiator, alkali developer solubility, organic solvent solubility, strength, softening Those having an appropriate temperature and the like are preferable, and specifically, a copolymer of (meth) acrylic acid and (meth) acrylate is preferable.

The weight average molecular weight of the polymer having an acidic group is preferably 5,000 to 200,000. When the weight average molecular weight is less than 5,000, when used as a colored photosensitive composition, there may be a problem in forming a coating film, and when it exceeds 200,000, the viscosity of the colored photosensitive composition increases. Sometimes.

The preferred range of the content of the resin in the pigment dispersion composition of the present invention varies depending on the kind used, but generally, it is usually from 10 to 200 parts by mass relative to 100 parts by mass of the pigment. Is preferably 20 to 15
0 parts by mass is more preferred. When the content is within the above range, the steric repulsion effect can be obtained, and the viscosity of the dispersion can be prevented from excessively increasing.

In the pigment dispersion composition of the present invention, the organic solvent in which the dispersant, the pigment and the resin are dispersed is not particularly limited and can be appropriately selected from known organic solvents. For example, ethylene glycol monomethyl ether (Poly) alkylene glycol monoalkyl ethers such as ethylene glycol monoethyl ether, propylene glycol monomethyl ether, propylene glycol monoethyl ether, diethylene glycol monomethyl ether, and ethylene glycol monoethyl ether, and their acetic esters; ethyl acetate, n-acetic acid Propyl, i-propyl acetate, n-butyl acetate, i-acetate
Acetates such as butyl; aromatic hydrocarbons such as benzene, toluene and xylene; ketones such as methyl ethyl ketone, acetone, methyl isobutyl ketone and cyclohexanone; ethanol, propanol, butanol, hexanol, cyclohexanol, ethylene glycol, diethylene glycol; And alcohols such as glycerin. These may be used alone or in combination of two or more. Among these,
Alkylene glycol monoalkyl ethers and their acetates, acetates, methyl ethyl ketone and the like are preferred.

The content of the organic solvent in the pigment dispersion composition is usually 10 to 1000 parts by mass, preferably 20 to 500 parts by mass, based on 100 parts by mass of the pigment. When the content is within the above range, it is preferable in that the viscosity of the pigment dispersion composition can be prevented from excessively increasing, and it is not difficult to secure a space during storage.

The pigment dispersion composition of the present invention may optionally contain other components such as a surfactant. It is preferable to include a surfactant because the dispersion stability of the pigment is further improved. Examples of the surfactant include an alkyl naphthalene sulfonate, an anionic surfactant represented by a phosphoric acid ester salt, a cationic surfactant represented by an amine salt, an aminocarboxylic acid, and a betaine type. Examples include an amphoteric surfactant.

In the pigment dispersion composition of the present invention, the pigment is preferably dispersed in the form of primary particles. The pigment dispersion composition of the present invention can be prepared, for example, by the following method. 1) A method in which a composition obtained by previously mixing the pigment and the dispersant is added to and dispersed in the organic solvent (or vehicle). 2) The pigment and the dispersion are dispersed in the organic solvent (or vehicle). 3) A method in which the pigment and the dispersant are separately dispersed in advance in the organic solvent (or vehicle), and the resulting dispersion is mixed (in this case, the dispersion is performed). 4) A method of dispersing the pigment in the organic solvent (or vehicle) and then adding the dispersant to the obtained dispersion.

The vehicle refers to a portion of a medium in which the pigment is dispersed when the paint is in a liquid state, and a component (binder resin) which is liquid and binds to the pigment to solidify a coating film. (The above-mentioned organic solvent).

The disperser used for dispersing the pigment is not particularly limited, and examples thereof include known dispersers such as a kneader, a roll mill, an attritor, a super mill, a dissolver, a homomixer, and a sand mill.

The pigment dispersion composition of the present invention can be used as a paint, printing ink and the like. Further, for example, a coating solution containing the pigment dispersion composition is applied on a support and dried to form a layer of the pigment dispersion composition, or a layer of the pigment dispersion composition formed on a temporary support. Is transferred onto a support, a layer of a known positive or negative photosensitive resin composition is formed thereon, exposed and developed, and then exposed in the same region with the photosensitive resin composition layer. An image can be formed by a method of removing the layer of the pigment dispersion composition described above. Further, by mixing with the photosensitive composition, it can be used for image formation as a colored photosensitive composition capable of forming an image by light irradiation. This will be described later.

<Colored Photosensitive Composition> The colored photosensitive composition of the present invention comprises a pigment dispersion composition of the present invention, a polyfunctional monomer having two or more ethylenically unsaturated double bonds, and a photopolymerization initiator. And is characterized by containing. The colored photosensitive composition of the present invention has excellent color tone because it contains a pigment, and has good dispersibility because it contains a dispersant. Furthermore, since the amount of impurities of alkali ions contained in the dispersant is reduced, the color filter can stably maintain good display characteristics, particularly when used in the production of a color filter.

The polyfunctional monomer having two or more ethylenically unsaturated double bonds is described in, for example, JP-A-60-1985.
Known (meth) acrylic acid esters, urethane (meth) acrylates, (meth) acrylic acid amides, allyl compounds, vinyl esters, and the like as described in JP-A-258538. These may be used alone or in combination of two or more. Among these, (meth) acrylates are preferred.

The content of the polyfunctional monomer having an ethylenically unsaturated double bond in the colored photosensitive composition is preferably from 10 to 60% by mass based on the total solid content. When the content is in the above range, it is preferable because the curing ability at the time of exposure is sufficiently maintained and the performance of other materials is not suppressed.

The photopolymerization initiator has a wavelength of about 30
It is preferred to use at least one compound having a molecular extinction coefficient of at least about 50 at 0 to 500 nm, such as, for example, JP-A-2-4866.
No. 4, JP-A-1-152449, and JP-A-2-153353, aromatic ketones, lophine dimers, benzoin, benzoin ethers, polyhalogens, and the like. No. These may be used alone or in combination of two or more. Among these, 4,4'-bis (diethylamino) benzophenone and 2- (o-chlorophenyl)-
A combination of 4,5-diphenylimidazole dimers,
And 4- [pN, N-di (ethoxycarbonylmethyl) -2,6-di (trichloromethyl) -s-triazine].

The content of the photopolymerization initiator in the colored photosensitive composition is preferably from 0.2 to 10% by mass based on the total solid content of the colored photosensitive composition. It is preferable that the content is within the above range, because it is possible to prevent the exposure sensitivity from becoming too high and difficult to control while maintaining the exposure sensitivity at a high level.

The colored photosensitive composition of the present invention is prepared by mixing the pigment dispersion composition of the present invention, a polyfunctional monomer having two or more ethylenically unsaturated double bonds, and a photopolymerization initiator. can do. In addition, at the time of preparation,
A resin may be further added. As the resin, a polymer having the acidic group which can be used in a pigment dispersion composition is preferable. It is preferable to use the same resin as the resin used when preparing the pigment dispersion composition. In the colored photosensitive composition of the present invention, the content of the resin (particularly, polymer having an acidic group) is preferably about 20 to 80% by mass based on the total solid content. When the content is within the above range, it is preferable because it is possible to maintain the strength of the coating film at a high level and to prevent the ability of another material from being hardly exhibited.

The colored photosensitive composition of the present invention can be used for image formation by light irradiation. Formation of a colored image using the colored photosensitive composition is basically performed in the following (1) to
It can be performed by the step (3). (1) After preparing the pigment dispersion composition, using the same to prepare the colored photosensitive composition (2) coating the obtained colored photosensitive composition on a substrate and drying, or Step of transferring a layer formed by coating and drying on another temporary support onto a substrate to form a layer of a colored photosensitive composition (3) Layer of a colored photosensitive composition formed on a substrate For exposing and developing a pattern to form a pattern

As the substrate, a transparent material such as a glass plate or a transparent plastic plate is generally used. In order to improve the adhesion between the substrate and the colored photosensitive composition, various commercially available silane coupling agents or the like are added to the colored photosensitive composition, or the substrate is subjected to a coupling treatment in advance. May be.

The application of the coating solution of the colored photosensitive composition to the substrate can be performed by using a known coating means such as a spin coater, a roll coater, a bar coater, and a curtain coater.

As a method for transferring the layer of the colored photosensitive composition formed on the temporary support onto the substrate, a method using a heat roll laminator under normal pressure or reduced pressure is preferable.

Examples of the developer used in the development include hydroxides or carbonates of alkali metals or alkaline earth metals, hydrogencarbonates, asimonia water, and aqueous solutions of quaternary ammonium salts. Can be These may be used alone or in combination of two or more. Among these, an aqueous solution of sodium carbonate is particularly preferred.

<Color Filter> The color filter of the present invention is a color filter having two or more patterned colored layers having different hues on a substrate, wherein the colored layer is a colored photosensitive composition of the present invention. It is characterized by consisting of things. The color filter of the present invention has a clear color tone and high light transmittance because the colored layer is formed of the colored photosensitive composition of the present invention. Furthermore, since the amount of impurities of alkali ions contained in the dispersant is reduced, good display characteristics can be stably maintained.

The color filter of the present invention is obtained by repeating the steps (2) and (3) to obtain a plurality of colors (usually R,
G, B). The color filter of the present invention can also be manufactured using a transfer method. For example, Japanese Patent Application Laid-Open Nos. 4-208940, 5-72724, 5-80503, and 5-1733 disclose a method of manufacturing a color filter using a transfer method.
The details are described in Japanese Patent Publication No. 20 and the like, and can be applied to the present invention.

The color filter of the present invention has a mode in which the colored layer is formed directly on a transparent substrate such as glass,
An embodiment in which the colored layer is formed on a substrate on which an active element such as an FT is formed (color filter on array: COA) is included. In the case of producing a COA, a through hole is opened in the colored layer, and an electrical connection is made between the transparent conductive film and the active element. In particular, when a through hole is formed, alkali ions and the like pass through the through hole. It was easily eluted into the liquid crystal cell, and conventionally, the display characteristics were likely to deteriorate. Therefore, the effect of the present invention is remarkable in the mode of COA in which through holes are formed.

The color filter of the present invention can be widely used for display devices such as personal computers, word processors, engineering workstations, navigation systems, televisions and videos.

[0072]

EXAMPLES Examples of the present invention will be described below, but the present invention is not limited to these examples. [Example 1] First, a dispersant having the following structure (exemplary compound 7)
Was synthesized by the following method. 18.5 parts of bis-3-diethylaminopropylamide 5-nitroisophthalate,
And 5.1 parts of triethylamine were dissolved in 60 parts of DMF and cooled with ice. To this was added a solution of 9.3 parts of 4-nitrobenzoyl chloride in 60 parts of acetone to effect amidation. After the reaction, 800 parts of water was added, and the crystals were collected by filtration and recrystallized from ethyl acetate to give 4-nitrobenzoyl-4- [3,5
-Bis (3-diethylaminopropylcarbamoyl)]
14 parts of phenylamide were obtained. The obtained compound (92 parts) was refluxed and reduced in 200 parts of isopropanol and 35 parts of water together with 112 parts of reduced iron and 12 parts of ammonium chloride to obtain 13.2 parts of an aniline derivative.

Further, the obtained aniline derivative 13.2
The mixture was added to 120 parts of methanol, and 18 parts of hydrochloric acid was added under ice cooling. The mixture was further cooled to -15 ° C. This is N
An aqueous solution (1.8 parts of aNO ₂ ) (20 parts of water) was added dropwise and diazotized (preparation of diazo liquid). Separately, 5.9 parts of 5-acetoacetylaminobenzimidazolone, 260 parts of methanol
Parts, 530 parts of water, and 10.8 parts of NaCO ₃ were prepared and cooled to 10 ° C. or lower.
The diazo solution obtained above was added dropwise thereto so as not to exceed 10 ° C., and reacted. The system was made basic by adding K ₂ CO ₃ , and the precipitated yellow product was collected by filtration and recrystallized from DMF and acetonitrile to give Exemplified Compound 7 shown above.
(Dispersant) 19 parts were obtained. The maximum absorption wavelength of the obtained compound was λmax 391 nm (in CHCl ₃ ).

[0074]

Embedded image

The obtained dispersant (exemplary compound 7) was washed with water in the following procedure. The obtained dispersant was added to 200 g of hot water at 80 ° C., and the mixture was stirred at 80 ° C. for 1 hour. 30
After cooling to ℃, the liquid was filtered, the dispersant was collected by filtration and washed with 200 g of water three times. Then, at 40 ° C
For one day and night.

After the water washing treatment, the total amount of sodium ions and potassium ions contained in the obtained dispersant was measured by an atomic absorption method, and was 200 ppm and 30 pp, respectively.
m (total 230 ppm). Further, when the water content in the dispersant was measured, it was 1.5% by mass of the total mass of the dispersant. The water content was determined by drying 3 g of the dispersant (Exemplified Compound 7) sampled in an aluminum dish at 105 ° C. overnight, and then subtracting the mass (g) after drying from 3 g to obtain the difference in dryness. Percentage to 3g of total mass before (% by mass)
Was calculated.

Next, a red pigment dispersion composition having the following composition was prepared.・ C. I. Pigment Red 254 ··· 6.4 g · Dispersant synthesized above (after washing treatment) ··· 0.6 g · Methacrylic acid / benzyl methacrylate 15.8 g (molar ratio 28/72, weight average molecular weight: 30,000, 40% 1-methoxy-2-propyl acetate solution) 1-methoxy-2-propyl acetate・ ・ ・ ・ 57.2g

That is, the above composition was converted to a motor mill M-50.
Using a zirconia bead having a diameter of 0.65 mm, the mixture was dispersed at a peripheral speed of 9 m / s for 9 hours by using (Eiger) to prepare a red pigment dispersion composition. The viscosity of the red pigment dispersion composition obtained here (measured at 29 ° C. with an ELD type viscometer (manufactured by Tokyo Rika Instruments Inc.)) was 14.5 mPa · s.

Next, the following components were mixed to prepare a colored photosensitive composition for producing a color filter. -Red pigment dispersion composition prepared as described above-32.4 g-Methacrylic acid / benzyl methacrylate copolymer-9.0 g (molar ratio 28/72, weight (Average molecular weight 30,000, 30% 1-methoxy-2-propyl acetate solution) -pentaerythritol tetraacrylate 5.2g -4- [p-N, N-di (ethoxycarbonylmethyl)] -2,6-di (trichloromethyl) -5-triazine 0.2 g hydroquinone monomethyl ether 0.01 g 1-methoxy-2-propyl acetate・ ・ ・ ・ ・ ・ 62g

The colored photosensitive composition for producing a color filter was applied on a non-alkali glass substrate using a spin coater, and dried at 100 ° C. for 2 minutes to form a film having a thickness of about 2 μm. Then, under a nitrogen stream, exposure with an ultra-high pressure mercury lamp, development with a 1% aqueous sodium carbonate solution,
A red coloring layer was formed. On top of this, a 0.1 μm thick I
A TO film was formed on the entire surface, and a hole having a diameter of 100 μm was formed on the ITO film by photolithography. Specifically, a photoresist was applied on the ITO film, prebaked, and then exposed through a mask pattern. After immersing the photoresist in a developing solution and developing, the sample is washed with water, post-baked, and immersed in an etching solution (ferric chloride: nitric acid = 1: 1) to form a hole having a diameter of 100 μm in the ITO film. Formed. Thereafter, the photoresist was stripped using a stripper, washed with water and dried to produce a substrate having a red colored layer. Separately, a substrate having an ITO film formed on the entire surface of an alkali-free glass was manufactured.

An alignment film was formed on both of the obtained two substrates by a printing method, and the alignment films were rubbed and then arranged to face each other. After bonding with a sealing material, liquid crystal was injected between the substrates, and the liquid crystal injection port was sealed with the sealing material to obtain a liquid crystal cell. The liquid crystal sealed between the substrates was a TN liquid crystal capable of driving at 4 V.

[Comparative Example 1] In the preparation of the red pigment dispersion composition of Example 1, a water-free dispersant (sodium ion content of 7000 ppm by atomic absorption method and potassium ion content) was used as a dispersant. 350
ppm, the total content was 10500 ppm), and a liquid crystal cell was produced in the same manner as in Example 1.

[Comparative Example 2] In Example 1, the drying conditions of the dispersant (exemplary compound 7) after the water washing treatment were as follows.
The dispersant was washed with water and dried in the same manner as in Example 1 except that the temperature was changed to 40 ° C. for 3 hours. Here, when the water content in the dispersant after the water washing treatment and the drying was measured in the same manner as in Example 1, it was 15.3% by mass of the total mass of the dispersant. Further, a red pigment dispersion composition was prepared in the same manner as in Example 1 using the above dispersant. The viscosity of the obtained red pigment dispersion composition measured in the same manner as in Example 1 was 652 mPa · s. still,
An attempt was made to prepare a colored photosensitive composition using the obtained red pigment dispersion composition, but the preparation could not be performed due to dispersion destruction.

The liquid crystal cells of Example 1 and Comparative Example 1 were driven by a rectangular wave of ± 4 V, 30 Hz for 100 hours, then sandwiched between polarizing plates, and gray level display was observed. In the liquid crystal cell of Comparative Example 1, the display of the portion corresponding to the hole formed in the ITO film was darker than the display of the portion where no hole was formed. This is considered to be due to the fact that ions in the colored layer eluted from the holes formed in the ITO film and the threshold value was lowered. On the other hand, Example 1
In each of the liquid crystal cells, the display at any point was uniformly good.

[0085]

According to the present invention, there is provided a pigment dispersion composition which is excellent in dispersibility and color tone, and in particular, when used for producing a color filter, the color filter can stably maintain good display characteristics. can do. Further, according to the present invention, it is possible to form an image having a clear color tone and high light transmittance, and particularly when the color filter is used for producing a color filter, the color filter can stably maintain good display characteristics. A colored photosensitive composition can be provided. further,
ADVANTAGE OF THE INVENTION According to this invention, while having a clear color tone and high light transmittance, the color filter which can maintain a favorable display characteristic stably can be provided.

Continued on the front page (51) Int.Cl. ⁷ Identification symbol FI Theme coat II (reference) G03F 7/004 501 G03F 7/004 501 505 505 F term (reference) 2H025 AB13 AC01 AD01 BC42 BC51 CA01 CA14 CA28 CB10 CB13 CB14 CB16 CC12 CC20 FA03 FA17 2H048 BA02 BA45 BA48 BB02 BB14 BB15 BB43 BB44 2H091 FA02Y FB04 FB12 FC10 FD04 LA16

Claims (6)

[Claims] A pigment dispersion composition comprising a dispersant, a pigment and a resin dispersed in an organic solvent, wherein the total content of sodium ions and potassium ions of the dispersant determined by an atomic absorption method is A pigment dispersion composition having a content of less than 10,000 ppm. 2. The water content of the dispersant is not more than 10% by mass of the total mass of the dispersant.
3. The pigment dispersion composition according to item 1. 3. The pigment dispersion composition according to claim 1, wherein the resin is a polymer having an acidic group. 4. The pigment dispersion composition according to claim 1, wherein the dispersant is a compound represented by the following general formula (I). Embedded image (In the general formula (I), A represents a component capable of forming an azo dye together with XY. X represents a single bond or a group selected from divalent linking groups represented by the following structural formula. Y represents
It represents a group represented by the following general formula (II). ) Embedded image (In the general formula (II), Z represents a lower alkylene group.
R ₂ is a lower alkylamino group or 5 containing a nitrogen atom;
Represents a 6 to 6 membered saturated heterocyclic group. a represents 1 or 2. ) 5. A pigment dispersion composition according to claim 1, comprising a polyfunctional monomer having two or more ethylenically unsaturated double bonds, and a photopolymerization initiator. A colored photosensitive composition comprising: 6. A color filter having two or more patterned colored layers having different hues on a substrate, wherein the colored layer is made of the colored photosensitive composition according to claim 5. Description: Color filter.