CN105446076B - Red pigment dispersion corrosion-resisting agent composition for colour filter - Google Patents
Red pigment dispersion corrosion-resisting agent composition for colour filter Download PDFInfo
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Abstract
The invention provides a red pigment dispersion resist composition for a color filter, which has excellent dispersion stability, tinting strength, contrast, brightness, heat resistance and solvent resistance. The red pigment dispersion resist composition for a color filter contains C.I. pigment Red 221, C.I. pigment Red 177, a pigment dispersion aid represented by general formula (1) and/or (2), an alkali-soluble resin, a photopolymerizable compound, a photopolymerization initiator, and an organic solvent. Wherein X and Y are the same or different and each represents a group which may be represented by F, Cl, Br or NO2、CH3Or OCH3A substituted phenyl group. M represents H, Na, K, NH4Or NR1R2R3R4(R1、R2、R3And R4The same or different, and represents a saturated or unsaturated aliphatic hydrocarbon group having 1 to 10 carbon atoms which may be substituted with other substituents, or an aromatic hydrocarbon group having 6 to 10 carbon atoms which may be substituted with other substituents. ). m represents an integer of 1 or more. And (c) a temperature sensor.
Description
Technical Field
The present invention relates to a red pigment dispersion resist composition for a color filter used in a color liquid crystal display device, an image sensor, or the like.
Background
The color filter used in a color liquid crystal display device or the like is composed of: on the surface of a transparent substrate such as glass, fine stripes (stripes) of 2 or more different colors are arranged in parallel or fine pixels are arranged in a vertically and horizontally fixed sequence. The pixel size is as fine as several 10 to several 100 μm, and each hue is arranged in a predetermined order.
The color liquid crystal display device colors white light from a backlight by transmitting the color filter, and displays a color image on a screen. Therefore, high transparency is required as a basic performance of the color filter. Therefore, the dye composition has been conventionally produced by a so-called dyeing method or the like in which a dye excellent in color characteristics is molecularly dispersed in a resin to be dyed. However, in recent years, as applications have been diversified, when it is required to improve reliability against long-term use such as heat resistance and light resistance, an organic pigment may be used instead of a dye having a limit to improve reliability thereof. In addition, various methods such as a printing method, an ink-jet method, and a photolithography method have been proposed as a method for manufacturing a color filter.
Furthermore, in recent years, in order to achieve power saving in particular in liquid crystal display devices equipped with devices, color filters having the following pixels are required: the transmittance of visible light is improved, a bright display screen can be obtained more efficiently with limited power consumption, and high contrast can be achieved to achieve high definition of the entire image.
The visible light transmission and contrast performance described above greatly depend on the performance of the pigment dispersed in each pixel of the color filter, and it is difficult to achieve the desired performance for the red pixel by using only 1 type of pigment, and it has been proposed to use another color-adjusting pigment in combination.
For example, a system has been proposed in which a toned red pigment is used in combination with pigment red 177 as a main red pigment (see, for example, patent document 1). Examples of the color-adjusting red pigment include red pigments having a maximum absorption peak in a wavelength region of 535 to 555nm, that is, pigment red 5, 9, 10, 17, 48: 1. 48: 2. 48: 3. 48: 4. 52: 2. 119, 166, 216, 224, 226. However, the improvement of the transmittance and contrast performance is limited in the system using the red pigment.
Further, a system has been proposed in which pigment red 177 or 254 is used as a toning red pigment in the pigment red 242 of the main red pigment (for example, see patent document 2). Further, a system has been proposed in which a red pigment such as pigment red 177, 207, 209, 224, 242 is used as a toning red pigment in pigment red 254 of a main red pigment (for example, see patent documents 3 and 4).
However, when pigment red 242 is used as the main pigment, there is a problem that the hue tends to be yellowish. On the other hand, when pigment red 254 is used, the transmittance is increased, but the contrast is decreased while the thickness of the colored film is increased. Further, there is a problem that solvent resistance is deteriorated or heat resistance is deteriorated (generation of sublimates) from the characteristics of the pigment.
In recent years, a backlight or the like using an LED as a light source is also used, and thus the color reproduction range of a color filter is expanded. However, available coloring pigments are limited due to the difference in the wavelength of light irradiated on each. For example, in the case of a backlight using an LED as a light source, the pigment concentration of a pixel has to be further increased from the relationship of the absorption wavelength region of light in the conventional combination of the above-mentioned pigments. Therefore, the red pigment-dispersed resist composition needs to be highly concentrated, and the production and stable storage of the composition itself over time are difficult. On the other hand, if the pigment concentration is set to a conventional ordinary concentration, the film thickness of the pixel film to obtain a desired color density becomes too thick, which makes it difficult to manufacture a color filter.
In order to solve this problem, when pigment red 179 and pigment red 208 suitable for the wavelength of light emitted from the LED are used, the color density can be obtained without increasing the pigment concentration of the pixel, and the film thickness can be controlled within a controllable range.
Further, as a method for improving luminance while maintaining high tinting strength with respect to the wavelength of light emitted from the LED, it is considered to use a red pigment such as pigment red 221 (for example, see patent document 5).
However, since the viscosity of pigment red 221 increases in the dispersion step and it becomes difficult to ensure the stability of the dispersion with time, the suitable fluidity and stability with time of the dispersion cannot be obtained by the known method.
Documents of the prior art
Patent document
Patent document 1 Japanese patent application laid-open No. 10-148712
Patent document 2 Japanese patent application laid-open No. 11-014824
Japanese patent application laid-open No. 2002-372618 of patent document 3
Patent document 4 Japanese patent laid-open No. 2003-248115
Japanese patent laid-open publication No. 2012-208329 in patent document 5
Disclosure of Invention
The invention provides a red pigment dispersion resist composition for a color filter, which has excellent dispersion stability, tinting strength, contrast, brightness, heat resistance and solvent resistance.
By using the c.i. pigment red 221 as the main pigment and the c.i. pigment red 177 as the toning pigment, a red pixel having high luminance and improved tinting strength can be obtained even when various backlight devices are used. Therefore, it is necessary to finely pulverize the pigment and stably disperse the pigment in a red pigment dispersion resist composition for a color filter, but the dispersion stability of the fine particles of the pigment containing c.i. pigment red 221 cannot be sufficiently obtained by the conventional technique.
Accordingly, the present applicant has conducted intensive studies on a technique for improving the dispersion stability of pigment fine particles containing c.i. pigment red 221, and as a result, has found a method for producing a red pigment dispersion resist composition for a color filter, which comprises adding the pigment dispersion aid specified in the present invention, an acrylic block copolymer having a tertiary amino group and/or a quaternary ammonium group, and an organic solvent to fine particles obtained by fine-granulating a pigment containing c.i. pigment red 221, and dispersing the resultant mixture to obtain a pigment dispersion. The red pigment dispersion resist composition for a color filter obtained by this method has a significantly improved dispersion stability of pigment fine particles containing c.i. pigment red 221 compared to the prior art, and therefore can solve all the problems of the present invention, and the present invention has been completed.
Namely, the present invention is as follows:
1. a red pigment dispersion resist composition for a color filter, comprising C.I. pigment Red 221, C.I. pigment Red 177, a pigment dispersion aid represented by the general formula (1) and/or (2), an alkali-soluble resin, a photopolymerizable compound, a photopolymerization initiator and an organic solvent,
wherein X and Y are the same or different and each represents a group which may be represented by F, Cl, Br or NO2、CH3Or OCH3A substituted phenyl group. M represents H, Na, K, NH4Or NR1R2R3R4(R1、R2、R3And R4The same or different, and represents a saturated or unsaturated aliphatic hydrocarbon group having 1 to 10 carbon atoms which may be substituted with other substituents, or an aromatic hydrocarbon group having 6 to 10 carbon atoms which may be substituted with other substituents. ). m represents an integer of 1 or more. Angle (c)
2. A red pigment dispersion resist composition for a color filter, which is characterized by comprising a pigment dispersion of C.I. pigment Red 221, a pigment dispersion of C.I. pigment Red 177, an alkali-soluble resin, a photopolymerizable compound, a photopolymerization initiator and an organic solvent,
the pigment dispersion of c.i. pigment red 221 is obtained by adding and dispersing a pigment dispersing aid represented by general formula (1) and/or (2), an acrylic block copolymer having a tertiary amino group and/or a quaternary ammonium group, and an organic solvent to fine particles obtained by fine-granulating c.i. pigment red 221,
the pigment dispersion of c.i. pigment red 177 is a pigment dispersion obtained by adding and dispersing a pigment dispersing aid represented by general formula (1) and/or (2), an acrylic block copolymer having a tertiary amino group and/or a quaternary ammonium group, and an organic solvent to fine particles obtained by fine-granulating c.i. pigment red 177,
wherein X and Y are the same or different and each represents a group which may be represented by F, Cl, Br or NO2、CH3Or OCH3Substituted phenyl, M represents H, Na, K, NH4Or NR1R2R3R4(R1、R2、R3And R4The same or different, and represents a saturated or unsaturated aliphatic hydrocarbon group having 1 to 10 carbon atoms which may be substituted with other substituents, or an aromatic hydrocarbon group having 6 to 10 carbon atoms which may be substituted with other substituents. ). m represents an integer of 1 or more.〕
3. A red pigment dispersion resist composition for a color filter, which is characterized by comprising a pigment dispersion of C.I. pigment Red 221, a pigment dispersion of C.I. pigment Red 177, an alkali-soluble resin, a photopolymerizable compound, a photopolymerization initiator and an organic solvent,
the pigment dispersion of c.i. pigment red 221 is obtained by adding and dispersing a pigment dispersing aid represented by general formula (3) and/or (4), an acrylic block copolymer having a tertiary amino group and/or a quaternary ammonium group, and an organic solvent to fine particles obtained by fine-granulating c.i. pigment red 221,
the pigment dispersion of c.i. pigment red 177 is a pigment dispersion obtained by adding and dispersing a pigment dispersing aid represented by general formula (3) and/or (4), an acrylic block copolymer having a quaternary ammonium group, and an organic solvent to fine particles obtained by fine-granulating c.i. pigment red 177,
[ in the formula, M represents H, Na, K, NH4Or NR1R2R3R4(R1、R2、R3And R4The same or different, and represents a saturated or unsaturated aliphatic hydrocarbon group having 1 to 10 carbon atoms which may be substituted with other substituents, or an aromatic hydrocarbon group having 6 to 10 carbon atoms which may be substituted with other substituents. ). m represents an integer of 1 or more. Angle (c)
4. The red pigment dispersion resist composition for a color filter according to any one of claims 1 to 3, wherein the pigment dispersion of C.I. pigment Red 221 contains a sulfonated compound of a compound having the same skeleton as that of C.I. pigment Red 221.
5. The red pigment dispersion resist composition for a color filter according to claim 4, wherein the pigment dispersion of the pigment Red 221 is a pigment dispersion obtained by adding and dispersing a pigment dispersing aid represented by the general formula (3) and/or (4), an acrylic block copolymer having a tertiary amino group and/or a quaternary ammonium group, and an organic solvent to a fine particle obtained by fine-granulating the C.I. pigment Red 221 in the presence of a sulfonated compound of a compound having the same skeleton as that of the C.I. pigment Red 221,
the pigment dispersion of c.i. pigment red 177 is a pigment dispersion obtained by adding and dispersing a pigment dispersing aid represented by general formula (3) and/or (4), an acrylic block copolymer having a tertiary amino group and/or a quaternary ammonium group, and an organic solvent to fine particles obtained by fine-granulating c.i. pigment red 177.
6. The red pigment dispersion resist composition for a color filter according to any one of claims 1 to 5, characterized in that the pigment dispersion of the C.I. pigment Red 221 contains 5 to 15 parts by mass of barium sulfate having a primary particle diameter of 5 to 20nm, based on 100 parts by mass of the total mass of the C.I. pigment Red 221.
7. A color filter obtained by using the red pigment dispersion resist composition for a color filter according to any one of claims 1 to 3, wherein the contrast (Bare: 1000) of the color filter is 700 or more.
According to the present invention, the following effects can be obtained.
By using the pigment dispersion resist composition for a color filter, a red filter having suitable chromaticity x and Y is obtained, and a display having brighter luminance Y is obtained.
The viscosity of the pigment dispersion resist composition can be set within an appropriate range and the film thickness can be reduced, and the production of a color filter is not difficult.
The pigment dispersion resist composition for a color filter can have excellent dispersion stability.
A red filter having excellent solvent resistance and heat resistance can be provided.
Detailed Description
Hereinafter, the red pigment dispersion resist composition for a color filter (hereinafter, also referred to as "pigment dispersion resist composition") of the present invention will be described in further detail.
(pigment)
The red pigment dispersion resist composition for a color filter of the present invention is a composition containing c.i. pigment red 221 and c.i. pigment red 177, and the pigment may be added as it is, or the pigment may be added in advance with a pigment dispersion aid represented by general formula (1) and/or (2), an acrylic block copolymer having a tertiary amino group and/or a quaternary ammonium group, an organic solvent, and if necessary, an alkali-soluble resin, and dispersed to form a pigment dispersion of c.i. pigment red 221 and a pigment dispersion of c.i. pigment red 177, and then the pigment dispersion may be contained.
Since a color filter is obtained by using the pigment dispersion resist composition containing the pigment dispersion, the color filter can have high contrast, high brightness, high heat resistance, and high solvent resistance.
The content of the c.i. pigment red 221 is preferably 30 mass% or more and less than 100 mass%, more preferably 40 mass% or more and less than 60 mass%, and c.i. pigment red 177 is preferably less than 70 mass%, more preferably 40 mass% or more and less than 60 mass%, based on the total mass of the pigments. When the content of the c.i. pigment red 221 is less than 30% by mass, chromaticity x and y may not be suitable as a red filter.
The c.i. pigment red 221 and c.i. pigment red 177 preferably have an average primary particle diameter of 30 to 50 nm. By having the average particle diameter in the above range, an image developed by the obtained color filter becomes higher in contrast.
In the present invention, the average particle size is determined by a laser diffraction particle size measuring apparatus: volume average particle diameter measured by Nanotrac (UPA-EX 150, manufactured by Nikkiso Co., Ltd.).
In the present invention, other pigments may be added and mixed in addition to the above-mentioned coloring pigments within a range not impairing the effects of the present invention. Examples of the other pigment include a yellow pigment and an orange pigment.
The amount of the pigment used in the present invention is preferably 5 to 80% by mass, more preferably 20 to 50% by mass, based on the total amount of the pigment used, as a mass fraction based on the total solid content of the pigment-dispersed resist composition.
(pigment dispersing aid)
The pigment dispersion aid contained in the pigment dispersion resist composition of the present invention preferably contains both of 2 pigment dispersion aids, i.e., a pigment dispersion aid (a) (hereinafter, also simply referred to as "pigment dispersion aid (a)") which is a compound represented by the following general formula (1) and/or general formula (2) and a pigment dispersion aid (B) (hereinafter, also simply referred to as "pigment dispersion aid (B)") which is a sulfonated compound having the same skeleton as that of c.i. pigment red 221, and may contain only the pigment dispersion aid (a) and not the pigment dispersion aid (B).
Both of the pigment dispersion aid (a) and the pigment dispersion aid (B) are preferably contained.
The pigment dispersion aid (a) used in the present invention is a compound represented by the general formula (1) and/or the general formula (2).
In the above general formulae (1) and (2), X and Y are the same or different and may be represented by F, Cl, Br, NO2、CH3Or OCH3A substituted phenyl group. M represents H, Na, K, NH4Or NR1R2R3R4。
M in the above general formulae (1) and (2) is NR1R2R3R4Each R in time1、R2、R3And R4The same or different, and represents a saturated or unsaturated aliphatic hydrocarbon group having 1 to 10 carbon atoms which may be substituted with other substituents, or an aromatic hydrocarbon group having 6 to 10 carbon atoms which may be substituted with other substituents.
Examples of the saturated or unsaturated aliphatic hydrocarbon group include alkyl groups such as methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl, tert-butyl, pentyl, hexyl, octyl, and decyl; alkenyl groups such as vinyl, allyl, and 1-butenyl; alkynyl groups such as ethynyl and propynyl. Examples of the aromatic hydrocarbon group include a phenyl group and a naphthyl group.
Examples of the other substituent include a hydroxyl group, a halogen group, a carboxyl group, an amino group, a lower alkyl group (having 1 to 5 carbon atoms), and the like. And, the above R1R2R3And R4Wherein 1 may be substituted with other substituents, or 2 or more may be substituted with other substituents. Further, "m" in the general formulae (1) and (2) is an integer of 1 or more.
In the pigment dispersion aid (a), the compound represented by the general formula (1) is a tautomer of an enol type and the compound represented by the general formula (2) is a ketone type, and the pigment dispersion resist composition of the present invention may contain two compounds. That is, the pigment dispersion aid (a) in the present invention includes either a case where the compound represented by the above general formula (1) or general formula (2) is contained or a case where the compound represented by the above general formula (1) or general formula (2) is contained.
As a preferable example of the pigment dispersion aid (a), a sulfonated product of c.i. pigment red 2 (the following general formula (3) and/or general formula (4)) is preferable from the viewpoint that a pigment dispersion having good fluidity and dispersion stability and higher levels of transparency and coloring power can be obtained even in a state where an organic pigment is finely dispersed.
The amount of the pigment dispersion aid (a) used is 0.5 to 30 parts by mass, preferably 3 to 15 parts by mass, per 100 parts by mass of the total of the pigments, and the amount of the sulfonated product of c.i. pigment red 221 as the pigment dispersion aid (B) used is 0.5 to 30 parts by mass, preferably 3 to 15 parts by mass, per 100 parts by mass of the total of the pigments.
(acrylic block copolymer having tertiary amino group and/or quaternary ammonium group)
The pigment dispersion resist composition of the present invention contains an acrylic block copolymer having a tertiary amino group and/or a quaternary ammonium group.
Examples of the acrylic block copolymer having a tertiary amino group and/or a quaternary ammonium group in the present invention include DISPERBYK-2000, DISPERBYK-2001, DISPERBYK-2020, DISPERBYK-2025, BYK-LPN 21116 and BYK-LPN 22102 (manufactured by BYK Co., Ltd.).
In the pigment dispersion resist composition of the present invention, the content of the acrylic block copolymer having a tertiary amino group and/or a quaternary ammonium group is preferably 1 to 200 parts by mass, and more preferably 1 to 60 parts by mass, based on 100 parts by mass of the total organic pigment used. When the content of the acrylic block copolymer having a tertiary amino group and/or a quaternary ammonium group is less than 1 part by mass, the pigment dispersibility may be lowered, while when it exceeds 200 parts by mass, the developability may be lowered.
(alkali-soluble resin)
The pigment dispersion resist composition of the present invention contains an alkali-soluble resin.
The alkali-soluble resin is not particularly limited as long as it is an alkali-soluble resin which is soluble in an alkali developing solution, particularly preferably in the developing solution used in the developing step in the production of a color filter. Among them, the alkali-soluble resin is preferably an alkali-soluble resin having a carboxyl group, and particularly preferably a copolymer of an ethylenically unsaturated monomer having 1 or more carboxyl groups and another copolymerizable ethylenically unsaturated monomer.
Specific examples of the copolymer of the ethylenically unsaturated monomer having 1 or more carboxyl groups and the other copolymerizable ethylenically unsaturated monomer include copolymers of an ethylenically unsaturated monomer having a carboxyl group such as acrylic acid or methacrylic acid and at least 1 ethylenically unsaturated monomer selected from styrene, 2-hydroxyethyl acrylate, 2-hydroxyethyl methyl acrylate, aryl methyl acrylate, benzyl methyl acrylate, cyclohexyl methyl acrylate, glyceryl monoacrylate, glyceryl methyl acrylate, N-phenylmaleimide, polystyrene macromonomer and polymethyl methacrylate macromonomer which are copolymerizable with the ethylenically unsaturated monomer having a carboxyl group.
The acid value of the alkali-soluble resin is preferably 50 to 300mg KOH/g. In this case, when the acid value is less than 50mgKOH/g, the solubility of the resist composition in the alkali developer may be lowered. On the other hand, if it exceeds 300mgKOH/g, the solubility in the alkali developer becomes too high, and when development is performed by the alkali developer, there is a possibility that the substrate of the colored layer is peeled off, and the film on the surface of the colored layer is rough.
In the present invention, the acid value is a theoretical acid value and is a value obtained by an arithmetic operation based on the content and the ethylenically unsaturated monomer having a carboxyl group.
The pigment dispersion resist composition of the present invention contains an alkali-soluble resin, and the content thereof is preferably a small amount from the viewpoint of dispersibility and dispersion stability in pigment dispersion described later.
Therefore, it is preferable to add the c.i. pigment red 221 pigment dispersion and the c.i. pigment red 177 pigment dispersion to at least one of them, and the red pigment dispersion resist composition for a color filter may be obtained by adding them separately from the pigment dispersion.
The mass average molecular weight of the alkali-soluble resin in the present invention is preferably 1,000 to 10 ten thousand. When the mass average molecular weight of the alkali-soluble resin is less than 1,000, the solubility to an alkali developer may be increased, and the developing property may be lowered. On the other hand, if it exceeds 10 ten thousand, the solubility in the organic solvent may decrease and the viscosity of the resist composition may increase.
In the present invention, the mass average molecular weight of the alkali-soluble resin is a mass average molecular weight in terms of polystyrene obtained by GPC. In the present invention, Water 2690 (manufactured by Watts) was used as the apparatus, and PLGel 5. mu. MIXED-D (manufactured by Polymer Laboratories) was used as the column.
In the pigment dispersion resist composition of the present invention, the content of the alkali-soluble resin is preferably 10 to 1,000 parts by mass, and more preferably 20 to 500 parts by mass, based on 100 parts by mass of the total organic pigment contained.
When the content of the alkali-soluble resin is less than 10 parts by mass, for example, alkali developability may be reduced, or scum or a film may be generated on the substrate in an unexposed portion or on the light-shielding layer. On the other hand, when it exceeds 1,000 parts by mass, since the concentration of the organic pigment is relatively decreased, there is a possibility that it is difficult to achieve the target color density as a thin film.
(photopolymerizable Compound)
The pigment dispersion resist composition of the present invention contains a photopolymerizable compound.
Examples of the photopolymerizable compound of the invention include monomers and oligomers having 1 or more photopolymerizable unsaturated bonds in the molecule. The photopolymerizable unsaturated bond means an unsaturated bond polymerizable by the following action: the photopolymerization initiator described later generates radicals and cations upon decomposition by active energy rays such as ultraviolet rays and electron beams.
Examples of the monomer having 1 photopolymerizable unsaturated bond in the molecule include methyl methacrylate, methyl butylacrylate, 2-ethylhexyl methyl acrylate, methyl methacrylate (methylacrylate), butyl acrylate, 2-ethylhexyl acrylate and other methyl alkylacrylate or acrylic acid esters; aralkyl methyl acrylates or acrylates such as benzyl methyl acrylate and benzyl acrylate; alkoxyalkyl methacrylate esters such as butoxyethyl methacrylate and butoxyethyl acrylate; aminoalkyl acrylates such as methyl N, N-dimethylaminoethylacrylate and N, N-dimethylaminoethylacrylate, or acrylic esters; methacrylic acid ester or acrylic acid ester of polyalkylene glycol alkyl ether such as diethylene glycol ethyl ether, triethylene glycol butyl ether, and dipropylene glycol methyl ether; methacrylic acid ester or acrylic acid ester of polyalkylene glycol aryl ether such as hexaethylene glycol phenyl ether; isobornyl methyl acrylate or acrylate; glyceryl methacrylate or acrylate; methyl 2-hydroxyethyl acrylate or acrylic ester, and the like.
Examples of the monomer having 2 or more photopolymerizable unsaturated bonds in the molecule include bisphenol A methyl diacrylate, 1, 4-butanediol methyl diacrylate, 1, 3-butanediol methyl diacrylate, diethylene glycol methyl diacrylate, glyceryl methyl diacrylate, neopentyl glycol methyl diacrylate, polyethylene glycol methyl diacrylate, polypropylene glycol methyl diacrylate, tetraethylene glycol methyl diacrylate, trimethylolpropane methyl triacrylate, pentaerythritol methyl tetraacrylate, dipentaerythritol methyl hexaacrylate, dipentaerythritol methyl pentaacrylate, bisphenol A diacrylate, 1, 4-butanediol diacrylate, 1, 3-butanediol diacrylate, diethylene glycol diacrylate, glyceryl diacrylate, and the like, Neopentyl glycol diacrylate, polyethylene glycol diacrylate, polypropylene glycol diacrylate, tetraethylene glycol diacrylate, trimethylolpropane triacrylate, pentaerythritol tetraacrylate, dipentaerythritol hexaacrylate, dipentaerythritol pentaacrylate, and the like. These monomers may be used alone or in combination of 2 or more.
In the present invention, the content of the photopolymerizable compound is preferably in the range of 3 to 50 mass% relative to the total solid content in the pigment-dispersed resist composition.
(photopolymerization initiator)
The pigment dispersion resist composition of the present invention contains a photopolymerization initiator.
The photopolymerization initiator in the present invention is not particularly limited as long as it can generate radicals and cations by irradiation with active energy rays such as ultraviolet rays and electron beams, and examples thereof include benzophenone, N ' -tetraethyl-4, 4 ' -diaminobenzophenone, 4-methoxy-4 ' -dimethylaminobenzophenone, benzil, 2-diethoxyacetophenone, benzoin methyl ether, benzoin isobutyl ether, benzyl dimethyl ketal, α -hydroxyisobutylphenone, thioxanthone, 2-chlorothioxanthone, 1-hydroxycyclohexylphenylketone, tert-butylanthraquinone, 1-chloroanthraquinone, 2, 3-dichloroanthraquinone, 3-chloro-2-methylanthraquinone, 2-ethylanthraquinone, 1, 4-naphthoquinone, and the like, 1, 2-benzoanthraquinone, 1, 4-dimethylanthraquinone, 2-phenylanthraquinone, 2-methyl-1 [4- (methylthio) phenyl ] -2-morpholinopropyl-1-one, triazine photopolymerization initiator, and the like. These photopolymerization initiators may be used alone or in combination of 2 or more.
In the present invention, the content of the photopolymerization initiator is preferably in the range of 1 to 20% by mass relative to the total solid content in the pigment-dispersed resist composition.
(organic solvent)
The pigment dispersion of the present invention contains an organic solvent.
Examples of the organic solvent in the present invention include those which are suitably used in the fields of ink, paint, liquid crystal color filter resist, and inkjet. Specific examples thereof include ether organic solvents such as ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, ethylene glycol monoisopropyl ether, ethylene glycol monobutyl ether, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, propylene glycol monomethyl ether, propylene glycol monoethyl ether, propylene glycol monobutyl ether, diethylene glycol diethyl ether, diethylene glycol dimethyl ether, and diethylene glycol methyl ethyl ether; ether ester-based organic solvents such as ethylene glycol monomethyl ether acetate, ethylene glycol monoethyl ether acetate, ethylene glycol monobutyl ether acetate, propylene glycol monomethyl ether acetate, and propylene glycol monoethyl ether acetate; ketone organic solvents such as methyl isobutyl ketone, cyclohexanone, 2-heptanone, and butyrolactone; ester organic solvents such as methyl 2-hydroxypropionate, ethyl 2-hydroxy-2-methylpropionate, 3-methyl-3-methoxybutyl propionate, methyl 3-methoxypropionate, ethyl 3-methoxypropionate, methyl 3-ethoxypropionate, ethyl ethoxyacetate, ethyl glycolate, and n-pentyl formate; alcohol solvents such as methanol, ethanol, isopropyl alcohol, and butanol; and nitrogen-containing organic solvents such as N-methylpyrrolidone, N-dimethylformamide, and N, N-dimethylacetamide. These may be used alone or in combination of 2 or more.
Among these organic solvents, diethylene glycol dimethyl ether, diethylene glycol methyl ethyl ether, ethylene glycol monomethyl ether acetate, propylene glycol monoethyl ether acetate, cyclohexanone, 2-heptanone, ethyl 2-hydroxypropionate, 3-methyl-3-methoxybutyl propionate, ethyl 3-methoxypropionate, methyl 3-ethoxypropionate, n-pentyl formate and the like are preferable in terms of solubility, dispersibility, coatability and the like, and propylene glycol monomethyl ether acetate is more preferable.
Further, these organic solvents are preferably contained in the red pigment dispersion resist composition in an amount of 50 mass% or more, more preferably 70 mass% or more, from the viewpoints of solubility of the alkali-soluble resin, pigment dispersibility, coatability, and the like.
(other Components)
Barium sulfate is preferably contained to improve the heat resistance and brightness of the pigment dispersion of the present invention. In the present invention, the content of barium sulfate is 0 to 15% by mass, preferably 5 to 12% by mass, based on 100 parts by mass of each of the pigments. When the amount of barium sulfate is more than 15 parts by mass, the coloring power is greatly reduced. Preferably, the primary particle diameter of the barium sulfate is 5 to 20 nm. When the primary particle diameter of the barium sulfate exceeds 20nm, the contrast tends to be lowered and foreign matter tends to be generated. The barium sulfate is used at the time of or after dispersion of the pigment subjected to the microparticulation treatment.
In addition, various additives such as a thermal polymerization inhibitor, an ultraviolet absorber, an antioxidant, and the like may be used as appropriate in the pigment dispersion resist composition of the present invention.
(method for producing pigment Dispersion)
The pigment dispersion of the present invention can be produced, for example, from the above-mentioned constituent materials by the following production method.
First, each of the untreated pigments was subjected to a microparticulation treatment (salt milling treatment) to obtain a microparticulated pigment. More preferably, the microparticulation treatment is performed in the presence of a pigment dispersion aid which is a sulfonated compound having the same skeleton as that of each pigment. By performing the microparticulation treatment in the presence of the pigment dispersion aid which is a sulfonated compound having a compound having the same skeleton as each pigment, the pigment can be uniformly micronized while suppressing crystallization of the pigment. The particle diameter of the dispersion liquid composed of the micronized pigment is about 50 to 70 nm.
The amount of the pigment dispersing aid used is 0.5 to 30 parts by mass, preferably 3 to 10 parts by mass, per 100 parts by mass of the pigment.
The above-mentioned micronization treatment may be a salt milling treatment in which the pigment is ground with an inorganic salt in the presence of a sulfonated compound of a compound having the same skeleton as the pigment to further micronize the primary particle diameter of the pigment, using a kneader, a kneading device in which 3 stirring blades are each rotated and revolved. The pigment obtained by salt milling in the presence of such a sulfonated compound having a compound having the same skeleton as the pigment is finely divided so that the primary particle diameter is further fine and uniform. The salt milling treatment using a kneading apparatus in which 3 stirring blades perform revolution motion while rotating on their own axis is also referred to as TRI-MIX treatment.
The TRI-MIX treatment will be described in further detail below.
The TRI-MIX treatment is performed by kneading a mixture containing a pigment, a water-soluble inorganic salt (hereinafter, also simply referred to as "inorganic salt") and a water-soluble dispersion medium (hereinafter, also simply referred to as "dispersion medium") in which the inorganic salt is substantially insoluble, with a kneading apparatus in which 3 stirring blades perform revolution motion while performing rotation motion, and then removing the inorganic salt and the dispersion medium.
In this process, a kneading apparatus in which 3 stirring blades perform planetary motion, that is, revolution motion while performing rotation motion, was used as a kneading apparatus. Accordingly, dead angles between the stirring blades and the inner surface of the device are extremely reduced, and a stronger and uniform shearing force can be obtained. The pigment particle size obtained by grinding with the inorganic salt under the shearing force is finer and more uniform than the primary particle size, and a color filter having higher transparency and contrast ratio than those of the conventional color filters can be obtained.
The term "revolution" as used herein means the rotation of the stirring blade in the tank. The term "kneading device that revolves the stirring blade" means a kneading device that moves the stirring blade itself and rotates the stirring blade in the tank. However, in the present specification, the kneading apparatus is included in the "kneading apparatus that revolves the stirring blade" as long as the relative movement between the kettle and the stirring blade is the same (for example, the kettle is rotated).
Further, the structure of the kneading apparatus preferably satisfies the following conditions (1) and (2).
(1) A triangle obtained by using the point where the 3 rotation axes intersect as a vertex with respect to a plane orthogonal to the rotation axes of the 3 stirring scrapers is an equilateral triangle.
(2) The revolution axis intersects the gravity center of the triangle.
The stirring blade preferably has a length from the bottom of the tank to the liquid surface and a width of the tank from the inner wall to the center. Examples of such a kneading apparatus include TRI-MIX (manufactured by Okakikai Co., Ltd.).
In addition, a wet treatment method of adding a pigment, an inorganic salt and a dispersion medium to a pot and kneading them can be used for this treatment.
The inorganic salt is not particularly limited as long as it is water-soluble, but from the viewpoint of cost, common salt (sodium chloride) is preferably used.
The particle size of the inorganic salt is preferably 200 μm or less, more preferably 50 μm or less. Accordingly, the particle diameter of the color pigment can be made finer and more uniform than the primary particle diameter.
In the present invention, the particle size of the inorganic salt is determined by a laser diffraction particle size measuring method and measuring apparatus: volume average particle diameter measured by Nanotrac (UPA-EX 150, manufactured by Nikkiso Co., Ltd.).
The dispersion medium is not particularly limited as long as it is a water-soluble dispersion medium having two conditions of water solubility and insolubilization of the inorganic salt. Among them, a high boiling point solvent having a boiling point of 120 ℃ or higher is preferable from the viewpoint of safety because the temperature increases during salt milling and the solvent is in a state of being easily evaporated.
Examples of such water-soluble dispersion media include alkoxy alcohols such as 2-methoxyethanol, 2-butoxyethanol, 2- (isopentyloxy) ethanol, 2- (hexyloxy) ethanol, 1-methoxy-2-propanol, and 1-ethoxy-2-propanol; glycols such as diethylene glycol, triethylene glycol, liquid polyethylene glycol, dipropylene glycol, and low molecular weight polypropylene glycol; and ethers such as diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, diethylene glycol monobutyl ether, triethylene glycol monomethyl ether, dipropylene glycol monomethyl ether, and dipropylene glycol monoethyl ether.
The TRI-MIX treatment using the above materials and apparatus can be performed by the following methods.
The pigment, a pigment dispersing aid which is a sulfonated compound having the same skeleton as each pigment, an inorganic salt and a dispersing medium are charged into a kettle. Next, 3 stirring blades of the kneading apparatus were rotated and revolved to grind the pigment with an inorganic salt. Thereafter, the substance slurried with warm water was filtered and the remaining inorganic salt and the dispersion medium were removed by water washing. In the grinding treatment of the pigment, it is preferable to appropriately adjust the amount of the material to be added (viscosity), the inner diameter of the pot, and the like so as to sufficiently exert stress for kneading. For example, it is preferable to perform the compounding and the treatment such that the load current at the time of the treatment using the TRI-MIX is in the range of 50% to 85% of the rated current value of the engine.
Next, each mixture containing each of the fine particles and the acrylic block copolymer having a tertiary amino group and/or a quaternary ammonium group, the pigment dispersion aid (a), the alkali-soluble resin, an organic solvent, and, if necessary, barium sulfate is obtained. Each of the obtained mixtures was kneaded and dispersed by using various dispersing machines such as a roll mill, a kneader, a high-speed stirring device, a bead mill, a ball mill, a sand mill, an ultrasonic dispersing machine, and a high-pressure dispersing machine, to obtain each pigment dispersion. The pigment dispersion may contain a photopolymerizable compound in advance.
(method for producing pigment Dispersion resist composition)
A method for obtaining the pigment dispersion resist composition of the present invention from each pigment dispersion will be described.
The method for obtaining the pigment dispersion resist composition of the present invention from each pigment dispersion can be obtained, for example, by the following (1) and (2).
(1) The pigment dispersion resist composition is obtained by mixing the pigment dispersions of c.i. pigment red 221 and c.i. pigment red 177 into a predetermined pigment ratio, and then adding a photopolymerizable compound, a photopolymerization initiator, the remaining alkali-soluble resin, an organic solvent, and barium sulfate as needed.
(2) After each pigment dispersion was added with a photopolymerizable compound, a photopolymerization initiator, the remaining alkali-soluble resin, an organic solvent, and, if necessary, barium sulfate to obtain each pigment-dispersed resist composition, the c.i. pigment red 264 pigment-dispersed resist composition and the c.i. pigment red 177 pigment-dispersed resist composition were mixed in a predetermined pigment ratio to obtain a pigment-dispersed resist composition.
By using the pigment dispersion resist composition obtained by the above method to produce a color filter so as to have a predetermined film thickness, a color filter having a contrast (Bare: 1000) of 700 or more can be obtained.
The conditions for measuring the contrast in the present invention were such that the film thickness of the color filter was 1.0 μm, and the color characteristics (x, Y) of each resist were measured by a spectrophotometer (UV-2500 PC, manufactured by shimadzu corporation, C light source 2 ° field) to obtain a contrast (Bare: 1000) when the chromaticity x was 0.6730 and the Y was 0.3200.
In the present invention, the contrast is more preferably 700 or more (Bare: 1000), and still more preferably 705 or more.
Examples
The present invention will be described in further detail with reference to examples, but the present invention is not limited to these examples. And unless otherwise specified, "%" means "% by mass" and "parts" means "parts by mass". In the present specification, "TRI-MIX" is a registered trademark manufactured by Kabushiki Kaisha, and "Yanjiaguo" is a registered trademark of Ciba Japan.
< pigment Dispersion aid >
(C.I. sulfonated pigment Red 221)
30ml of concentrated sulfuric acid was added to a 100ml Erlenmeyer flask, 10g of C.I. pigment Red 221 was charged while stirring with a magnetic stirrer, and the mixture was stirred at room temperature for 30 minutes. A1L beaker was charged with a mixture of 50g of water and 50g of ice, and the above reaction was poured into the ice water and stirred with a magnetic stirrer for 30 minutes. This was filtered and washed with water under reduced pressure, and the obtained solid was dried to obtain 12g of a sulfonated product of c.i. pigment red 221.
(C.I. sulfonated substance of pigment Red 2)
30ml of concentrated sulfuric acid was added to a 100ml Erlenmeyer flask, 10g of C.I. pigment Red 2 was added thereto while stirring with a magnetic stirrer, and the mixture was stirred at room temperature for 30 minutes. A1L beaker was charged with a mixture of 50g of water and 50g of ice, and the above reaction was poured into the ice water and stirred with a magnetic stirrer for 30 minutes. This was filtered and washed with water under reduced pressure, and the obtained solid was dried, thereby obtaining 12g of a sulfonated product of c.i. pigment red 2.
(C.I. sulfonated product of pigment orange 71)
30ml of concentrated sulfuric acid was added to a 100ml Erlenmeyer flask, and 10g of C.I. pigment orange 71 was added thereto while stirring with a magnetic stirrer, and the mixture was stirred at room temperature for 30 minutes. A1L beaker was charged with a mixture of 50g of water and 50g of ice, and the above reaction was poured into the ice water and stirred with a magnetic stirrer for 30 minutes. This was filtered and washed with water under reduced pressure, and the obtained solid was dried, thereby obtaining 12g of a sulfonated product of c.i. pigment orange 71.
< micronization treatment >
Preparation example 1 (micronization treatment PR221 (pigment Red 221))
Into a pot of TRI-MIX TX-15 (trade name, manufactured by uphole corporation), 800 parts of c.i. pigment red 221, 8000 parts of sodium chloride having a particle size of 20 μm, and 1920 parts of diethylene glycol were charged. The resulting mixture was kneaded at 45 ℃ for 3 hours in a range of 70% of the rated current value of 9.3A, and then subjected to salt milling treatment. Subsequently, 1300 parts of the resulting kneaded material was put into 3 liters of warm water, and stirred at 70 ℃ for 1 hour to be made into a slurry. After removing sodium chloride and diethylene glycol by repeated filtration and washing with water, the mixture was dried at 40 ℃ overnight to obtain 720 parts of microparticulated PR 221.
Preparation example 2 (micronized PR221 (pigment Red 221) containing pigment dispersing aid)
Into a pot of TRI-MIX TX-15 (trade name, manufactured by uphole corporation), 800 parts of c.i. pigment red 221, 40 parts of a sulfonated product of c.i. pigment red 221, 8000 parts of sodium chloride having a particle size of 20 μm, and 1920 parts of diethylene glycol were charged. The resulting mixture was kneaded at 45 ℃ for 3 hours in a range of 70% of the rated current value of 9.3A, and then subjected to salt milling treatment. Subsequently, 1300 parts of the resulting kneaded material was put into 3 liters of warm water, and stirred at 70 ℃ for 1 hour to be made into a slurry. After removing sodium chloride and diethylene glycol by repeated filtration and washing with water, the mixture was dried at 40 ℃ overnight to obtain 740 parts of a micronized PR221 containing a pigment dispersion aid.
Preparation example 3 (micronized PR254 (pigment Red 254) containing pigment dispersing aid)
800 parts of C.I. pigment Red 254, 40 parts of a sulfonated product of C.I. pigment orange 71, 8000 parts of sodium chloride having a particle size of 20 μm and 1920 parts of diethylene glycol were charged into a TRI-MIX TX-15 (trade name, manufactured by Kokai Co., Ltd.). The resulting mixture was kneaded at 45 ℃ for 3 hours in a range of 70% of the rated current value of 9.3A, and then subjected to salt milling treatment. Subsequently, 1300 parts of the resulting kneaded material was put into 3 liters of warm water, and stirred at 70 ℃ for 1 hour to be made into a slurry. After removing sodium chloride and diethylene glycol by repeated filtration and washing with water, the mixture was dried at 40 ℃ overnight to obtain 740 parts of a pigment dispersion aid-containing microparticulated PR 254.
Preparation example 4 (micronized PR177 (pigment Red 177))
800 parts of C.I. pigment Red 177, 8000 parts of sodium chloride having a particle size of 20 μm and 1920 parts of diethylene glycol were charged into a TRI-MIX TX-15 (trade name, manufactured by Okakikai Co., Ltd.). The resulting mixture was kneaded at 45 ℃ for 3 hours in a range of 70% of the rated current value of 9.3A, and then subjected to salt milling treatment. Subsequently, 1300 parts of the resulting kneaded material was put into 3 liters of warm water, and stirred at 70 ℃ for 1 hour to be made into a slurry. After removing sodium chloride and diethylene glycol by repeated filtration and washing with water, the mixture was dried at 40 ℃ overnight to obtain 720 parts of micronized PR 177.
< acrylic block copolymer having tertiary amino group and/or quaternary ammonium group >
BYK-LPN 22102 (BYK Chemicals, Inc.; BYK), solid content concentration 40% by mass
< alkali soluble resin >
BzMA/MAA copolymer (benzyl methyl acrylate/methacrylic acid copolymer, theoretical acid number: 120mg KOH/g, mass average molecular weight: 25,000)
< photopolymerizable Compound >
DPEHA (dipentaerythritol hexaacrylate)
< photopolymerization initiator >
Yanjiaguo 369 (2-benzyl-2- (dimethylamino) -1- (4-morpholinophenyl) -butanone-1, manufactured by Ciba Japan Co., Ltd.)
< organic solvent >
PGMEA (propylene glycol monomethyl ether acetate)
< barium sulfate >
BF-40 (average primary particle diameter 0.01 μm made by Sakai chemical industry Co., Ltd.)
(production of Dispersion liquid and resist composition)
< Red pigment Dispersion >
Each of the fine particles for each dispersion was mixed with each of the other components in accordance with the composition shown in Table 1, and kneaded at a temperature of 40 to 50 ℃ for 3 hours by a bead mill to obtain each of the red pigment dispersions.
< pigment dispersion resist composition for color filter >
Each of the pigment dispersion compositions obtained by the above-mentioned steps was uniformly mixed with other materials (BzMA/MAA copolymer, DPEHA, gazel-good-solid, PGMEA) using a high-speed mixer so as to have the compositions shown in table 1, and then filtered through a filter having a pore diameter of 3 μm, to obtain a red pigment dispersion resist composition for each color filter.
< Red pigment Dispersion resist compositions for color Filter of examples and comparative examples >
The red pigment dispersion resist compositions for color filters of examples 1 to 9 and comparative examples 1 to 3 were obtained by combining the respective red pigment dispersion resist compositions for color filters so as to have the formulations shown in table 2.
Evaluation method
The following evaluations were performed, and the evaluation results are shown in tables 1 and 2.
< viscosity >
The pigment dispersion resist compositions for color filters of examples and comparative examples were each collected in a glass bottle, stoppered and stored at room temperature for 1 day, and then the viscosity at 25 ℃ was measured using an E-type viscometer (model RE100L of R100 type viscometer, manufactured by Toyobo industries Co., Ltd.). The lower the viscosity, the better the fluidity, the more excellent the pigment dispersion.
< Dispersion stability >
The pigment dispersion resist compositions for color filters of examples and comparative examples were each collected in a glass bottle, and after being stored at a closed state at room temperature for 7 days, the state was evaluated in accordance with the following evaluation criteria.
O: neither thickening nor precipitation was observed.
And (delta): the thickening and sedimentation were found to be restored to the original extent by gentle shaking.
X: it was found that the thickening and the precipitates were not recovered to the original extent even by vigorous shaking.
< evaluation of color characteristics of pigment Dispersion resist composition for color Filter >
The color characteristics (x, Y) of the resists of the examples and comparative examples having a film thickness of 1.0 μm were measured by using a spectrophotometer (UV-2500 PC, 2 ℃ C. illuminant field, manufactured by Shimadzu corporation). In examples 1 to 3 and comparative example 1, the contrast, luminance Y, and film thickness were determined when the chromaticity x was 0.6730 and Y was 0.3200. In examples 4 to 6 and comparative example 2, the contrast, luminance Y, and film thickness were determined when the chromaticity x was 0.6700 and Y was 0.3122. In examples 7 to 9 and comparative example 3, the contrast, luminance Y, and film thickness were determined when the chromaticity x was 0.6800 and Y was 0.3150.
< Heat resistance >
The pigment-dispersed resist compositions for color filters of examples and comparative examples were coated on a glass substrate using a spin coater to make the film thickness to 1.0 μm, and were prebaked (pre-baker) at 100 ℃ for 3 minutes, then exposed to a high-pressure mercury lamp, and further postbaked (post-baker) at 270 ℃ for 60 minutes. Then, the surface of the obtained resist coating film was observed with a microscope (VHS-500, 500 times magnification, product of KEYENCE), and the degree of surface roughness accompanying sublimation of the pigment during post-baking was observed, and evaluated according to the following evaluation criteria.
O: no surface roughness was found
X: surface roughness was found
< solvent resistance >
The test substrate used for the evaluation of the color characteristics was immersed in N-methylpyrrolidone for 30 minutes. After the substrate was taken out, the evaluation was performed according to the following evaluation criteria.
O: elution of the coating film was not observed
X: the dissolution of the coating film was observed
TABLE 1
TABLE 2
According to examples 1 to 3, the color filter is bright when the luminance is 15.90 to 16.00 when the required chromaticity x is 0.6730 and y is 0.3200. Further, the contrast at this time was high at 730 in both examples 1 and 2, and sufficiently high at 530 in example 3, compared with 1000 in barrel. In addition, the color filters of examples 1 to 3 were excellent in heat resistance and solvent resistance.
On the other hand, according to comparative example 1 in which c.i. pigment red 221 was not used, the obtained color filter was good in brightness, but poor in contrast, heat resistance and solvent resistance.
The same tendency was confirmed in the combinations of examples 4 to 6 and comparative example 2, and also in the combinations of examples 7 to 9 and comparative example 3.
From the above results, it is understood that the use of c.i. pigment red 221 can exert more significant effects than the use of c.i. pigment red 254.
Claims (7)
1. A red pigment dispersion resist composition for a color filter, characterized by comprising C.I. pigment Red 221 as a main pigment, C.I. pigment Red 177 as a toning pigment, a pigment dispersion aid represented by general formula (1) and/or (2), an alkali-soluble resin, a photopolymerizable compound, a photopolymerization initiator and an organic solvent, wherein the content of C.I. pigment Red 221 is 40% by mass or more based on the total mass of the pigments,
wherein X and Y are the same or different and may be represented by F, Cl, Br, NO2、CH3Or OCH3Substituted phenyl, M represents H, Na, K, NH4Or NR1R2R3R4Wherein R is1、R2、R3And R4The same or different, and represents a saturated or unsaturated aliphatic hydrocarbon group having 1 to 10 carbon atoms which may be substituted with other substituents or an aromatic hydrocarbon group having 6 to 10 carbon atoms which may be substituted with other substituents, and m represents an integer of 1 or more.
2. A red pigment dispersion resist composition for a color filter, characterized by comprising a pigment dispersion of C.I. pigment Red 221 as a main pigment, a pigment dispersion of C.I. pigment Red 177 as a toning pigment, an alkali-soluble resin, a photopolymerizable compound, a photopolymerization initiator and an organic solvent, wherein the content of C.I. pigment Red 221 is 40% by mass or more relative to the total mass of the pigments,
the pigment dispersion of c.i. pigment red 221 is obtained by adding and dispersing a pigment dispersing aid represented by general formula (1) and/or (2), an acrylic block copolymer having a tertiary amino group and/or a quaternary ammonium group, and an organic solvent to fine particles obtained by fine-granulating c.i. pigment red 221,
the pigment dispersion of c.i. pigment red 177 is a pigment dispersion obtained by adding and dispersing a pigment dispersing aid represented by general formula (1) and/or (2), an acrylic block copolymer having a tertiary amino group and/or a quaternary ammonium group, and an organic solvent to fine particles obtained by fine-granulating c.i. pigment red 177,
wherein X and Y are the same or different and may be represented by F, Cl, Br, NO2、CH3Or OCH3Substituted phenyl, M represents H, Na, K, NH4Or NR1R2R3R4Wherein R is1、R2、R3And R4The same or different, and represents a saturated or unsaturated aliphatic hydrocarbon group having 1 to 10 carbon atoms which may be substituted with other substituents or an aromatic hydrocarbon group having 6 to 10 carbon atoms which may be substituted with other substituents, and m represents an integer of 1 or more.
3. A red pigment dispersion resist composition for a color filter, characterized by comprising a pigment dispersion of C.I. pigment Red 221 as a main pigment, a pigment dispersion of C.I. pigment Red 177 as a toning pigment, an alkali-soluble resin, a photopolymerizable compound, a photopolymerization initiator and an organic solvent, wherein the content of C.I. pigment Red 221 is 40% by mass or more relative to the total mass of the pigments,
the pigment dispersion of c.i. pigment red 221 is obtained by adding and dispersing a pigment dispersing aid represented by general formula (3) and/or (4), an acrylic block copolymer having a tertiary amino group and/or a quaternary ammonium group, and an organic solvent to fine particles obtained by fine-granulating c.i. pigment red 221,
the pigment dispersion of c.i. pigment red 177 is a pigment dispersion obtained by adding and dispersing a pigment dispersing aid represented by general formula (3) and/or (4), an acrylic block copolymer having a quaternary ammonium group, and an organic solvent to fine particles obtained by fine-granulating c.i. pigment red 177,
wherein M represents H, Na, K, NH4Or NR1R2R3R4Wherein R is1、R2、R3And R4The same or different, and represents a saturated or unsaturated aliphatic hydrocarbon group having 1 to 10 carbon atoms which may be substituted with other substituents or an aromatic hydrocarbon group having 6 to 10 carbon atoms which may be substituted with other substituents, and m represents an integer of 1 or more.
4. The red pigment dispersion resist composition for color filters according to any one of claims 1 to 3, wherein the pigment dispersion of C.I. pigment Red 221 contains a sulfonated compound of a compound having the same skeleton as that of C.I. pigment Red 221.
5. The red pigment dispersion resist composition for a color filter according to claim 3, wherein the pigment dispersion of the pigment Red 221 is obtained by adding and dispersing a pigment dispersing aid represented by the general formula (3) and/or (4), an acrylic block copolymer having a tertiary amino group and/or a quaternary ammonium group, and an organic solvent to a fine particle obtained by fine-granulating the C.I. pigment Red 221 in the presence of a sulfonated compound having a compound having the same skeleton as that of the C.I. pigment Red 221,
the pigment dispersion of c.i. pigment red 177 is a pigment dispersion obtained by adding and dispersing a pigment dispersing aid represented by general formula (3) and/or (4), an acrylic block copolymer having a tertiary amino group and/or a quaternary ammonium group, and an organic solvent to fine particles obtained by fine-granulating c.i. pigment red 177.
6. The red pigment dispersion resist composition for color filters according to claim 5, wherein the pigment dispersion of C.I. pigment Red 221 contains 5 to 15 parts by mass of barium sulfate having a primary particle diameter of 5 to 20nm, based on 100 parts by mass of the total of the C.I. pigment Red 221.
7. A color filter obtained from the red pigment dispersion resist composition for a color filter according to any one of claims 1 to 3, wherein the Bare: 1000 is 700 or more.
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| KR20200087675A (en) | 2019-01-11 | 2020-07-21 | 산요 시키소 가부시키가이샤 | Azo pigment composition and manufacturing method thereof |
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| JP3924872B2 (en) | 1997-04-28 | 2007-06-06 | 住友化学株式会社 | Red composition for color filter and color filter |
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| JP2002372618A (en) | 2001-06-14 | 2002-12-26 | Fujifilm Arch Co Ltd | Red hardening composition for color filter and color filter using the same |
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| WO2009041312A1 (en) * | 2007-09-27 | 2009-04-02 | Sakata Inx Corp. | Pigment dispersion assistant, pigment dispersion containing the same, and use of the pigment dispersion |
| JP2011095313A (en) * | 2009-10-27 | 2011-05-12 | Toppan Printing Co Ltd | Color filter |
| KR20110045530A (en) * | 2009-10-27 | 2011-05-04 | 동우 화인켐 주식회사 | Red colored photosensitive resin composition, color filter and liquid crystal display device having the same |
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