JP2008009013A - Colorant composition for color filter and color filter substrate - Google Patents

Abstract

<P>PROBLEM TO BE SOLVED: To provide a color filter and a colorant composition in which dispersion is stabilized even when a fine acid pigment is used, and which cause neither reduction of contrast nor increase of surface roughness and are suitable for realizing a liquid crystal display having good display performance. <P>SOLUTION: The colorant composition for color filters comprises a pigment, a first polymer, a second polymer and a solvent, wherein the pigment is an acid pigment and the second polymer is a polyamic acid amide represented by general formula (1). <P>COPYRIGHT: (C)2008,JPO&INPIT

Description

  The present invention relates to a color filter colorant composition and a color filter substrate using the same.

  Usually, a colorant composition that forms a color pattern of a color filter is obtained by a pigment dispersion method in which a pigment is dispersed in a resin. A colorant composition in which a pigment is dispersed in an organic solvent solution of polyamic acid is known as a colorant composition capable of forming a color pattern of a color filter having excellent heat resistance and light resistance (Patent Document 1, Patent Document 1). 2).

  In this case, the pigment to be used is selected so as to match the backlight characteristics of the liquid crystal display device, and two or more kinds of pigments are often used after toning at a certain ratio. For example, the R (red) pixel of the color filter is used by selecting two or more kinds of red, orange, and yellow pigments and toning them at a certain ratio. Similarly, the G (green) pixel is used by selecting two or more types of green, orange, and yellow pigments and toning them. Similarly, B (blue) pixels are used by selecting two or more blue and violet pigments and toning them. The pigment is selected from the required chromaticity characteristics as described above. However, depending on the pigment used, the combination of pigments, and the toning ratio, the pigment does not disperse stably and aggregates, and the transmittance and contrast of the pixel coating film are reduced. This causes a decrease and an increase in surface roughness, thereby reducing the display quality of the liquid crystal display device.

  In order to solve such a problem, it has been proposed to contain a polymer having a basic group in the side chain (Patent Document 3).

However, it is now important for color filters to have high contrast, and dispersion stabilization of fine pigments in colorant compositions is becoming more important. In particular, when the fine pigment is an acidic pigment, sufficient dispersion stabilization cannot be performed by the conventional method, resulting in a decrease in contrast and an increase in surface roughness.
On the other hand, modification of the carboxylic acid of the polyamic acid to change its properties has been studied for some time, and a method for preparing a resin composition has been reported in detail (Patent Document 4).
It has also been reported that a polyamic acid ester is used for pigment dispersion, but this is intended to increase the solubility in lactones and to impart photosensitivity, and is intended by the present invention. This is different from the purpose (Patent Document 5).
JP 60-184202 A JP 60-184203 A JP 2002-285068 A Japanese Patent Laid-Open No. 04-218051 Japanese Patent Laid-Open No. 08-092496

  The problem to be solved by the present invention is to stabilize the dispersion even when a fine acidic pigment is used, and to realize a liquid crystal display device with good display performance without causing a decrease in contrast or an increase in surface roughness. Another object is to provide a color filter and a colorant composition suitable for the above.

As a result of intensive studies to solve the problems of the prior art, the present inventors have found that the following colorant composition and color filter have excellent characteristics.
1. In a color filter colorant composition comprising a pigment, a first polymer, a second polymer, and a solvent, the pigment is an acidic pigment, and the second polymer is represented by the following general formula (1) A colorant composition for a color filter, which is a polyamic acid amide.

(Where R ¹ is a tetravalent organic group, R ² is a divalent organic group, R ³ is a monovalent organic group, R ⁴ is a monovalent organic group or a hydroxyl group, and R ¹ and R ² are Each may be the same or different, and l, m, and n are each independently an integer of 1 or more.)
2. The colorant composition for a color filter according to 1, wherein an amidation rate of the polyamic acid amide is 15% or more and less than 50%.
3. The first polymer is a polyamic acid, and the polyamic acid amide represented by the general formula (1) has an amino group in the polyamic acid having the same structure as the polyamic acid used in the first polymer 3. The color filter composition for color filters according to item 1 or 2, wherein
4). The color filter board | substrate obtained by apply | coating the colorant composition for color filters in any one of Claims 1-3 on a transparent substrate, and pattern-forming.

  By using the colorant composition mentioned in the present invention, a color filter having a high contrast and a small surface roughness can be provided even when an acidic pigment is used. By using the color filter, a liquid crystal display device with favorable display characteristics can be provided.

  In the present invention, the colorant composition needs to contain at least one acidic pigment and a polyamic acid amide resin as the second polymer.

  The acidic pigment as used in the present invention refers to a pigment having an isoelectric point of 7 or less when the pH at which the ζ potential of the pigment becomes 0 (hereinafter, isoelectric point) is measured in a 0.1 mol / L NaCl aqueous solution. It is. In addition, when an isoelectric point is 7 or less by using a pigment derivative separately from the pigment, it can be said to be an acidic pigment. The pigment derivative may be processed directly into the pigment or may be added at the time of dispersion.

  Specific examples of typical pigments that can be used in the present invention are shown below by color index (CI) numbers, but are not limited thereto. These can be used alone or in combination of two or more.

  Examples of yellow pigments include pigment yellow (hereinafter abbreviated as PY) 12, 13, 17, 20, 24, 83, 86, 93, 95, 109, 110, 117, 125, 129, 137, 138, 139, 147, 148, 150, 153, 154, 166, 168, 185, etc. can be used, and examples of orange pigments include pigment orange (hereinafter abbreviated as PO) 13, 36, 38, 43, 51. 55, 59, 61, 64, 65, 71 can be used, and examples of red pigments include Pigment Red (hereinafter abbreviated as PR) 9, 48, 97, 122, 123, 144, 14 9, 166, 168, 177, 179, 180, 192, 209, 215, 216, 217, 220, 22 3, 224, 226, 227, 228, 2 0, 254, etc. can be used, and pigment violet (hereinafter abbreviated as PV) 19, 23, 29, 30, 32, 37, 40, 50, etc. can be used as examples of purple pigments, Examples of blue pigments include Pigment Bull (hereinafter abbreviated as PB) 15, 15: 3, 15: 4, 15: 6, 22, 60, 64, and the like, and examples of green pigments. Pigment Green (hereinafter abbreviated as PG) 7, 10, 36, etc. can be used, and as examples of black pigments, Pigment Black 7, Carbon Black, Titanium Black, etc. can be used. .

  In the present invention, examples of the polyamic acid amide used as the second polymer include those represented by the following general formula (1).

(Where R ¹ is a tetravalent organic group, R ² is a divalent organic group, R ³ is a monovalent organic group, R ⁴ is a monovalent organic group or a hydroxyl group, and l, m, and n are independent of each other. And an integer of 1 or more.)
In the general formula (1), l, m, and n represent the ratio of the three types of structures in the entire polymer, and do not indicate that the polymer is a block copolymer.

  The amount of polyamic acid amide used in the present invention is not particularly limited, but is preferably 12% or less, more preferably 6% or less, based on the total amount of the first polymer and the second polymer. It is. When the ratio of the polyamic acid amide with respect to the total amount exceeds 12%, the luminance (Y in the XYZ color system) decreases greatly.

  In the present invention, the production method of the polyamic acid amide is not particularly limited. (1) A production method of reacting a polyamic acid obtained by reacting tetracarboxylic dianhydride and a diamino compound with alkylamines or anilines, Alternatively, (2) a method of reacting a reaction product of an alkylamine or aniline and a tetracarboxylic dianhydride with a diamino compound is easy (Patent Document 4).

  In the present invention, the amidation rate of the polyamic acid amide is preferably 15% or more and less than 50%, and more preferably 25% or more. If the amidation rate is less than 15%, the dispersion stabilization is not sufficient, and the effect of preventing the decrease in contrast and the increase in surface roughness is not sufficient. Moreover, when the amidation rate is 50% or more, the decrease in luminance (Y) becomes large.

Here, the amidation rate is the ratio of the carboxyl group that is not used for the amide bond of the main chain in the polyamic acid and reacts with amines or anilines, and is calculated by the following formula in the general formula (1). The
[Amidation rate (%)] = ((2l + m) / (2l + 2m + 2n)) × 100
In the present invention, as the tetracarboxylic dianhydride that can be used for amide acid amide or amide acid, for example, aliphatic or alicyclic ones can be used. 2,3,4-cyclobutanetetracarboxylic dianhydride, 1,2,3,4-cyclopentanetetracarboxylic dianhydride, 1,2,3,5-cyclopentanetetracarboxylic dianhydride, 1, 2,4,5-bicyclohexenetetracarboxylic dianhydride, 1,2,4,5-cyclohexanetetracarboxylic dianhydride, 1,3,3a, 4,5,9b-hexahydro-5- (tetrahydro- 2,5-dioxo-3-furanyl) -naphtho [1,2-C] furan-1,3-dione and the like. In addition, when an aromatic material is used, a polyimide precursor composition that can be converted into a polyimide having good heat resistance can be obtained, and specific examples thereof include 3,3 ′, 4,4′-benzophenone. Tetracarboxylic dianhydride, pyromellitic dianhydride, 3,4,9,10-perylenetetracarboxylic dianhydride, 3,3 ′, 4,4′-diphenylsulfone tetracarboxylic dianhydride, 4 , 4′-oxydiphthalic anhydride, 3,3 ′, 4,4′-biphenyltetracarboxylic dianhydride, 1,2,5,6-naphthalenetetracarboxylic dianhydride, 3,3 ″, 4 4 "-paraterphenyl tetracarboxylic dianhydride, 3,3", 4,4 "-metaterphenyl tetracarboxylic dianhydride. In addition, when a fluorine-based material is used, a polyimide precursor composition that can be converted into a polyimide having good transparency in a short wavelength region can be obtained. As a specific example, 4,4 ′-(hexa Fluoroisopropylidene) diphthalic anhydride and the like. In addition, this invention is not limited to these, The tetracarboxylic dianhydride is used 1 type (s) or 2 or more types.

  In the present invention, as the amide that can be used for amide acid amide or amide acid, for example, aliphatic or alicyclic ones can be used, and specific examples thereof include ethylenediamine, 1,3-diamino Examples include cyclohexane, 1,4-diaminocyclohexane, 4,4′-diamino-3,3′-dimethyldicyclohexylmethane, 4,4′-diamino-3,3′-dimethyldicyclohexyl, and the like. In addition, when an aromatic material is used, a polyimide precursor composition that can be converted into a polyimide having good heat resistance can be obtained. Specific examples thereof include 4,4′-diaminodiphenyl ether, 3, 4 '-Diaminodiphenyl ether, 4,4'-diaminodiphenylmethane, 3,3'-diaminodiphenylmethane, 4,4'-diaminodiphenylsulfone, 3,3'-diaminodiphenylsulfone, 4,4'-diaminodiphenyl sulfide, m- Phenylenediamine, p-phenylenediamine, 2,4-diaminotoluene, 2,5-diaminotoluene, 2,6-diaminotoluene, benzidine, 3,3'-dimethylbenzidine, 3,3'-dimethoxybenzidine, o-tolidine 4,4 "-diaminoterphenyl, 1,5-diaminonaphthalene, 3 3'-dimethyl-4,4'-diaminodiphenylmethane, 4,4'-bis (4-aminophenoxy) biphenyl, 2,2-bis [4- (4-aminophenoxy) phenyl] propane, bis [4- ( 4-aminophenoxy) phenyl] ether, bis [4- (4-aminophenoxy) phenyl] sulfone, bis [4- (3-aminophenoxy) phenyl] sulfone, and the like. When used, a polyimide precursor composition that can be converted into a polyimide having good transparency in the short wavelength region can be obtained. As a specific example, 2,2-bis [4- (4-aminophenoxy) Phenyl] hexafluoropropane and the like.

In the present invention, alkylamines or anilines (HNR ³ R ⁴ , R ³ : monovalent organic group, R ⁴ : monovalent organic group or hydroxyl group) that can be used for polyamic acid amide or amide acid are limited. For example, primary amines include butylamine, pentylamine, hexylamine, octylamine, benzylamine, 4-ethylaniline and the like. Divalent amines include diethylamine, dipropylamine, diethanolamine, and N-methyl. Aniline, N-ethylaniline, etc. are mentioned. The present invention is not limited to these, and one or more alkylamines or anilines are used.

  As still another additive, the general formula (2)

(In the formula, R ⁵ is a divalent organic group having 1 to 10 carbon atoms, and R ⁶ , R ⁷ , R ⁸ and R ⁹ are monovalent organic groups having 1 to 10 carbon atoms. May be different.)
When the siloxane diamine represented by is used, the adhesion to the inorganic substrate can be improved.
Siloxane diamine is usually used in an amount of 1 to 20 mol% in the total diamine. If the amount of siloxane diamine is too small, the effect of improving the adhesiveness is not exhibited, and if it is too large, the heat resistance is lowered. Specific examples of the siloxane diamine include bis-3- (aminopropyl) tetramethylsiloxane. The present invention is not limited to these, and one or more diamines are used.

  The solvent preferably used in the present invention is not particularly limited as long as the polyamic acid amide is dissolved, and a general organic solvent can be used. Although it does not specifically limit as an organic solvent, For example, (poly) alkylene glycol ether type polarities, such as ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, propylene glycol monomethyl ether, propylene glycol monoethyl ether, diethylene glycol monomethyl ether Solvents, amide polar solvents such as N-methyl-2-pyrrolidone, N, N-dimethylacetamide, N, N-dimethylformamide, β-propiolactone, γ-butyrolactone, γ-valerolactone, δ-valerolactone, Lactones such as γ-caprolactone and ε-caprolactone, alcohols such as ethanol, butanol and isopropanol, cellosolves such as methyl cellosolve and ethyl cellosolve, propylene It may be used propylene glycol derivatives and the like, such as glycol monomethyl ether. These solvents can be used alone or in combination of two or more.

  Considering the solubility of the polyamic acid amide, it is preferable to use 50% or more of the polar organic solvent such as the amide polar solvent and the lactone based on the total amount of the solvent. In the present invention, a surfactant is added to the colorant composition for the purpose of improving the coating property of the colorant composition and the uniformity of the surface of the colored film, or for the purpose of improving the dispersibility of the pigment. be able to. The addition amount of the surfactant is preferably 0.001 to 10 wt%, more preferably 0.01 to 1 wt%, based on the pigment. If the amount added is too small, there is no effect of improving the coating property, the uniformity of the colored film surface, or the dispersibility of the pigment, and if it is too large, the coating property is poor or the pigment is aggregated. Specific examples of such surfactants include anionic surfactants such as ammonium lauryl sulfate and polyoxyethylene alkyl ether sulfate triethanolamine, cationic surfactants such as stearylamine acetate and lauryltrimethylammonium chloride, and lauryldimethylamine oxide. , Amphoteric surfactants such as lauryl carboxymethyl hydroxyethyl imidazolium betaine, nonionic surfactants such as polyoxyethylene lauryl ether, polyoxyethylene stearyl ether, sorbitan monostearate, and the like are used. Such surfactants can be used alone or in combination. Such a surfactant can be added at any point during or before or after the pigment dispersion step. However, care must be taken because the dispersibility of the pigment may change depending on the point of addition.

Next, an example of a method for producing a color filter when the colorant composition is used will be described.
As a method of applying the colorant composition on the substrate, a method of applying to the substrate by a spin coater, a bar coater, a blade coater, a roll coater, a die coater, a screen printing method, or the like, or immersing the substrate in the colorant composition Various methods such as spraying the method and the colorant composition onto the substrate can be used. As the substrate, a transparent substrate such as soda glass, non-alkali glass, borosilicate glass, or quartz glass, or a semiconductor substrate such as silicon or gallium arsenide is usually used, but is not particularly limited thereto. In addition, when apply | coating a colorant composition on a board | substrate, if the board | substrate surface is processed with adhesion aids, such as a silane coupling agent, the adhesive force of a colored film and a board | substrate can be improved.

  After coating on the transparent substrate by such a method, a polyimide precursor colored film is formed by air drying, heat drying, vacuum drying or the like. In the case of heat drying, an oven, a hot plate, or the like is used, and it is preferably performed in the range of 50 to 180 ° C., more preferably 80 to 120 ° C., for 30 seconds to 3 hours. When the temperature is too low, the solvent does not readily evaporate. Conversely, when the temperature is too high, the solubility in the developer is lowered. A pattern is formed on the polyimide precursor colored film thus obtained by ordinary wet etching. First, a positive photoresist is applied on the polyimide precursor colored film to form a photoresist film. Subsequently, a mask is placed on the photoresist film and irradiated with ultraviolet rays using an exposure apparatus. After the exposure, the photoresist film and the polyimide precursor colored film are simultaneously etched with an alkaline developer for positive photoresist. After the etching, the photoresist film that has become unnecessary is peeled off. The polyimide precursor colored film is then converted into a polyimide colored film by heat treatment. The heat treatment is preferably performed in air, in a nitrogen atmosphere, or in a vacuum, preferably at a temperature of 150 to 450 ° C., more preferably 180 to 350 ° C., and particularly preferably 200 to 320 ° C. .5-5 hours continuously or stepwise.

  When the above steps are performed for the three colorant compositions of R (red), G (green), and B (blue) and, if necessary, the black colorant composition, a color filter for a liquid crystal display device is produced. be able to.

  EXAMPLES Hereinafter, although this invention is demonstrated concretely based on an Example, this invention is not limited to these. In addition, the measuring method described in the Example is as showing below.

(Measurement method)
<Contrast>
The brightness of the parallel Nicols and the direct Nicols of the sample is measured with a color luminance meter (Topcon BM-5A) on the backlight (Mingaku System) in the field of view twice, and the brightness of the parallel Nicols and the brightness of the direct Nicols is measured. The ratio was contrast.

<Surface roughness>
The center line average roughness (Ra) was measured with Surfcom 1400D manufactured by Tokyo Seimitsu Co., Ltd.

<Chromaticity>
Measurement was performed with a MCPD-2000 manufactured by Otsuka Electronics Co., Ltd. with a field of view of 2 degrees and a C light source. The C light source is standard light C defined by the International Commission on Illumination (CIE). This has a color temperature of 6740 ° K. It can be obtained by applying a specified filter to a gas-filled tungsten light bulb that has been lit at a specified rate. The nature of this light corresponds to daylight including blue sky light. The 2 ° visual field refers to a visual field in the range of 0 ° to 2 °. The C light source and the 2 ° field of view are the transmitted light when the light of the C light source is transmitted through the measurement object, and the optical axis through which the light of the C light source vertically penetrates the measurement object is 0 °. And when the measurement object is used as a base point, it means that the transmitted light in the field of view within the range of 0 to 2 ° is measured (transmitted light chromaticity measurement) on the transmission side.
A. Step of preparing polyamic acid (first polymer) solution 190.2 g (0.95 mol equivalent) of 4,4′-diaminodiphenyl ether and 12.4 g (0.05 mol equivalent) of bis (3-aminopropyl) tetramethyldisiloxane Charged to a 3000 ml four-necked flask with 1400 g of γ-butyrolactone and 575.6 g of N-methyl-2-pyrrolidone, 288.3 g (0.98 mol equivalent) of 3,3 ′, 4,4′-biphenyltetracarboxylic dianhydride ) Was added and reacted at 70 ° C. for 3 hours, and then 3.0 g of phthalic anhydride was added and further reacted at 70 ° C. for 2 hours to obtain a 20% by mass polyamic acid solution (PA).
B. Step of preparing polyamic acid amide (second polymer) solution 246.95 g of polyamic acid solution (PA) was charged into a 500 ml three-necked flask and heated to 80 ° C., then 2.14 g of benzylamine was added, and 30 After stirring for 5 minutes, 8.56 g of γ-butyrolactone was added to obtain a polyamic acid amide solution (PAA-1).

  246.95 g of polyamic acid solution (PA) was charged into a 500 ml three-necked flask and the temperature was raised to 80 ° C. Then, 4.29 g of benzylamine was added and stirred for 30 minutes, and then 17.16 g of γ-butyrolactone was added. Thus, a polyamic acid amide solution (PAA-2) was obtained.

   246.95 g of polyamic acid solution (PA) was charged into a 500 ml three-necked flask and the temperature was raised to 80 ° C., then 6.43 g of benzylamine was added and stirred for 30 minutes, and then 25.72 g of γ-butyrolactone was added. Thus, a polyamic acid amide solution (PAA-3) was obtained.

  246.95 g of polyamic acid solution (PA) was charged into a 500 ml three-necked flask and heated to 80 ° C., then 15.00 g of benzylamine was added and stirred for 30 minutes, and then 60.00 g of γ-butyrolactone was added. Thus, a polyamic acid amide solution (PAA-4) was obtained.

  246.95 g of polyamic acid solution (PA) was charged into a 500 ml three-necked flask and the temperature was raised to 80 ° C. Then, 6.07 g of hexylamine was added and stirred for 30 minutes, and then 24.28 g of γ-butyrolactone was added. Thus, a polyamic acid amide solution (PAA-5) was obtained.

C. Preparation of acrylic polymer solution (AP1) First, 33 parts by weight of methyl methacrylate, 33 parts by weight of styrene, 34 parts by weight of methacrylic acid, 3 parts by weight of 2,2′-azobis (2-methylbutyronitrile), Then, 150 parts by weight of γ-butyrolactone was charged into a polymerization vessel, stirred at 90 ° C. for 2 hours, further raised to 100 ° C. and reacted for 1 hour. Next, 33 parts by weight of glycidyl methacrylate, 1.2 parts by weight of dimethylbenzylamine, and 0.2 parts by weight of p-methoxyphenol were added to the resulting solution and stirred at 90 ° C. for 4 hours. 50 g of γ-BL was added to obtain an acrylic polymer solution (AP1) (solid content 40% by mass). The obtained acrylic polymer solution (AP1) had a resin acid value of 80.0 (mgKOH / g) and a weight average molecular weight (Mw) of 22,000.
D. Preparation of Colorant Composition Example 1
PB15: 6 (acid treatment) 70 g, PV23 (basic treatment) 10 g, polyamic acid amide solution (PAA-1) 50 g, and γ-butyrolactone 870 g were dispersed with glass beads 1000 g at 7000 rpm for 30 minutes using a homogenizer. The glass beads were removed by filtration to obtain a pigment dispersion (PD-1).

  25 g of pigment dispersion (PD-1), 30 g of polyamic acid solution (PA), 35 g of γ-gamma-butyrolactone, and 10 g of 3-methoxy-3-methyl-1-butanol are placed in a 100 cc plastic container for 1 hour in a ball mill. The colorant composition (CP-1) was obtained by stirring.

Example 2
A pigment dispersion (PD-2) was obtained in the same manner as in Example 1 except that the resin used for the pigment dispersion was changed from the polyamic acid amide (PAA-1) solution to the polyamic acid amide solution (PAA-2). .

  A colorant composition (CP-2) was obtained in the same manner as in Example 1 except that the pigment dispersion (PD-1) was changed to the pigment dispersion (PD-2).

Example 3
A pigment dispersion (PD-3) was obtained in the same manner as in Example 1 except that the resin used for the pigment dispersion was changed from the polyamic acid amide solution (PAA-1) to the polyamic acid amide solution (PAA-3). .

  A colorant composition (CP-3) was obtained in the same manner as in Example 1 except that the pigment dispersion (PD-1) was changed to the pigment dispersion (PD-3).

Example 4
A pigment dispersion (PD-4) was obtained in the same manner as in Example 1 except that the resin used for the pigment dispersion was changed from the polyamic acid amide solution (PAA-1) to the polyamic acid amide solution (PAA-4). .

  A colorant composition (CP-4) was obtained in the same manner as in Example 1 except that the pigment dispersion (PD-1) was changed to the pigment dispersion (PD-4).

Example 5
A pigment dispersion (PD-5) was obtained in the same manner as in Example 1 except that the resin used for the pigment dispersion was changed from the polyamic acid amide solution (PAA-1) to the polyamic acid amide solution (PAA-5). .

  A colorant composition (CP-5) was obtained in the same manner as in Example 1 except that the pigment dispersion (PD-1) was changed to the pigment dispersion (PD-5).

Example 6
PB15: 6 (acid treatment) 7 g, PV23 (basic treatment) 1 g, polyamic acid amide solution (PAA-3) 10 g, and γ-butyrolactone 82 g were dispersed with glass beads 100 g at 7000 rpm for 30 minutes using a homogenizer. The glass beads were removed by filtration to obtain a pigment dispersion (PD-6).

  25 g of pigment dispersion (PD-6), 28.75 g of polyamic acid solution (PA), 36.25 g of γ-gamma-butyrolactone, and 10 g of 3-methoxy-3-methyl-1-butanol were placed in a 100 cc plastic container and ball milled. Was stirred for 1 hour to obtain a colorant composition (CP-6).

Example 7
PB15: 6 (acid treatment) 7 g, PV23 (basic treatment) 1 g, polyamic acid amide solution (PAA-3) 20 g, and γ-butyrolactone 72 g were dispersed with glass beads 100 g at 7000 rpm for 30 minutes using a homogenizer. The glass beads were removed by filtration to obtain a pigment dispersion (PD-7).

  25 g of pigment dispersion (PD-7), 26.25 g of polyamic acid solution (PA), 38.75 g of γ-gamma-butyrolactone, and 10 g of 3-methoxy-3-methyl-1-butanol were placed in a 100 cc plastic container and ball milled. Was stirred for 1 hour to obtain a colorant composition (CP-6).

Example 8
25 g of pigment dispersion (PD-3), 7.5 g of acrylic polymer solution (AP1) 3 g of polyfunctional acrylic monomer “DPHA” (manufactured by Nippon Kayaku), photopolymerization initiator “Irgacure 907” (manufactured by Ciba Specialty Chemicals) 1.5 g, 53 g of γ-gamma-butyrolactone, and 10 g of 3-methoxy-3-methyl-1-butanol are placed in a 100 cc plastic container and stirred for 1 hour in a ball mill to obtain a colorant composition (CP-8). It was.

Comparative Example 1
PB15: 6 (acid treatment) 7 g, PV23 (basic treatment) 1 g, polyamic acid solution (PA) 5 g, and γ-butyrolactone 87 g together with glass beads 100 g using a homogenizer at 7000 rpm for 30 minutes, and then glass beads Removal by filtration gave a pigment dispersion (PD-8).

  25 g of pigment dispersion (PD-8), 30 g of polyamic acid (PA), 35 g of γ-gamma-butyrolactone, and 10 g of 3-methoxy-3-methyl-1-butanol were placed in a 100 cc plastic container and stirred for 1 hour in a ball mill. As a result, a colorant composition (CP-9) was obtained.

E. Polyimide colored film forming film Colorant compositions (CP-1) to (CP-7), (CP-9) are spin-coated on an alkali-free glass substrate, and heated and dried at 120 ° C. for 10 minutes using an oven. A polyimide precursor film was obtained. A positive type photoresist (OFPR-800 manufactured by Tokyo Ohka Kogyo Co., Ltd.) was applied on this film and dried by heating at 80 ° C. for 20 minutes to obtain a resist film having a thickness of 1 μm. Ultraviolet rays were irradiated through a chromium photomask using an ultraviolet exposure machine. After the exposure, the photoresist and the polyimide precursor colored coating were developed at the same time by immersing in a developer composed of a 2.38 wt% aqueous solution of tetramethylammonium hydroxide. After etching, the unnecessary photoresist layer was peeled off with methyl cellosolve acetate. Furthermore, the polyimide precursor colored film thus obtained was heat-treated at 300 ° C. for 30 minutes using an oven to obtain a polyimide colored film.

F. Formation of Acrylic Colored Film A colorant composition (CP-8) was spin-coated on an alkali-free glass substrate and dried by heating at 90 ° C. for 10 minutes using an oven to obtain a coating film. Ultraviolet rays were irradiated through a chromium photomask using an ultraviolet exposure machine. After the exposure, the film was immersed in a developer composed of a 5 wt% aqueous solution of potassium hydroxide to obtain a patterned coating film. Further, the colored film thus obtained was heat-treated at 220 ° C. for 30 minutes using an oven to obtain an acrylic colored film.

G. Film characteristic evaluation The chromaticity of the film obtained by E and F was measured, and the surface roughness, contrast, and luminance (Y in the XYZ color system) were measured at a film thickness where the chromaticity coordinate y was 0.1. .

Claims (4)

In a color filter colorant composition comprising a pigment, a first polymer, a second polymer, and a solvent, the pigment is an acidic pigment, and the second polymer is represented by the following general formula (1) A colorant composition for a color filter, which is a polyamic acid amide.

(Where R ¹ is a tetravalent organic group, R ² is a divalent organic group, R ³ is a monovalent organic group, R ⁴ is a monovalent organic group or a hydroxyl group, and R ¹ and R ² are Each may be the same or different, and l, m, and n are each independently an integer of 1 or more.) The colorant composition for a color filter according to claim 1, wherein the amidation rate of the polyamic acid amide is 15% or more and less than 50%. The first polymer is a polyamic acid, and the polyamic acid amide represented by the general formula (1) has an amino group in the polyamic acid having the same structure as the polyamic acid used in the first polymer The colorant composition for a color filter according to claim 1 or 2, wherein A color filter substrate obtained by applying and patterning the color filter colorant composition according to claim 1 on a transparent substrate.