JP2010223987A - Red composition for color filter and color filter having the same - Google Patents

Abstract

<P>PROBLEM TO BE SOLVED: To provide a red composition for a color filter having high luminance and contrast, and to provide a color filter having the composition. <P>SOLUTION: The red composition for a color filter contains PR254, PR177 and an orange pigment. The color filter contains the composition. <P>COPYRIGHT: (C)2011,JPO&INPIT

Description

  The present invention relates to a red composition useful for a color filter and a color filter having the same.

In recent years, color liquid crystal display devices are often used for displays for personal computers, portable terminals, and televisions, and demand is increasing. The color filter of such a liquid crystal display device is generally formed on a transparent substrate and a transparent substrate, and is formed on the transparent substrate so as to partition the colored layers of the three primary colors of red, green, and blue and the respective colored patterns. And a light shielding portion. As a method for forming such a colored layer, a printing method, an ink jet method, a pigment dispersion method using photolithography, and the like are known.
As a red pigment (red pigment) for color filters mainly used for television, from the viewpoint of luminance, DPP: diketopyrrolopyrrole C.I. I. The hue of CI Pigment Red 254 (hereinafter referred to as “PR254”) is preferable. Therefore, conventionally, PR254 alone or anthraquinone C.I. I. In general, a red color obtained by using together with Pigment Red 177 (hereinafter referred to as “PR177”) was used.
However, liquid crystal television is inferior in terms of contrast, and there has been an increasing demand for high contrast coloring compositions.
On the other hand, in addition to the improvement of the PR254 pigment itself, improvement as a red light-sensitive material has been performed by increasing the ratio of PR177 having a high contrast. In this method, toning is performed with a yellow pigment instead of increasing PR177 having a strong blue tint, but there is a problem in that the luminance is greatly reduced.

At present, the PR254 / PR177 / yellow pigment system is widely used, and the contrast and brightness of the yellow pigment are becoming important. For example, in Patent Document 1, C.I. I. A system of PR254 / PR177 / PY139 using Pigment Yellow 139 (hereinafter referred to as “PY139”) is disclosed. In this system, the reduction in luminance was improved, but the contrast was insufficient.
In Patent Document 2, C.I. I. The use of Pigment Yellow 150 (hereinafter referred to as “PY150”) has been proposed. In the system of PR254 / PR177 / PY150, although the contrast is very high, the brightness is remarkably lowered, and it is difficult to achieve both brightness and contrast.

JP 2000-131517 A JP 2007-133131 A

  Under such circumstances, an object of the present invention is to provide a red composition for a color filter having both brightness and contrast and a color filter having the same.

As a result of intensive studies to achieve the above-mentioned problems, the present inventor has found that the above-described problems can be achieved by combining PR254 and PR177 with an orange pigment. The present invention has been completed based on such findings.
That is, the present invention
[1] C.I. I. Pigment red 254, C.I. I. A red composition for a color filter containing CI Pigment Red 177 and an orange pigment,
[2] Among a total of 100 parts by mass of pigment, C.I. I. Pigment Red 254 is 10 to 60 parts by mass, C.I. I. Pigment Red 177 is 20 to 80 parts by mass, and the orange pigment is 10 to 49 parts by mass. The red composition for color filters as described in [1] above,
[3] The red composition for a color filter as described in [1] or [2] above, wherein the orange pigment has a dispersion average particle size of 20 to 80 nm,
[4] The red composition for a color filter according to any one of the above [1] to [3], wherein the orange pigment has a naphthol structure, a DPP structure or a condensed azo structure,
[5] The orange pigment is C.I. I. Pigment orange 38, C.I. I. Pigment orange 71 and / or C.I. I. A red composition for a color filter according to any one of the above [1] to [3], which is CI Pigment Red 242;
[6] The red composition for color filters as described in any one of [1] to [5] above, which contains at least a pigment, a dispersant, a binder resin, a radiation sensitive compound, a photopolymerization initiator, and a solvent. ,
[7] In the XYZ color system chromaticity diagram under the conditions of the color filter having the red composition for a color filter according to any one of [1] to [6], and [8] C light source and 2 ° field of view. The color filter according to [7], wherein the chromaticity coordinates (x, y) are in the following range.
0.630 ≦ x ≦ 0.680
0.310 ≦ y ≦ 0.350

  According to the present invention, it is possible to provide a red composition for a color filter having both brightness and contrast and a color filter having the same.

It is a schematic diagram which shows the measuring method of contrast.

The red composition for a color filter of the present invention contains PR254, PR177 and an orange pigment.
The red composition for a color filter of the present invention can be applied to known color filter production methods such as a printing method, an ink jet method, and a pigment dispersion method, but the pigment dispersion method is preferably used because pixels can be accurately produced. In particular, a method using a negative photosensitive red composition is preferably used.
In the red composition for a color filter of the present invention, PR254 is in the range of 10 to 60 parts by mass, PR177 is in the range of 20 to 80 parts by mass, and the orange pigment is in the range of 10 to 49 parts by mass in the total 100 parts by mass of the pigment. It is preferable. This range is preferable because both high luminance and high contrast can be achieved.

The orange pigment used in the present invention is not particularly limited. I. Pigment orange 1, C.I. I. Pigment orange 5, C.I. I. Pigment orange 13, C.I. I. Pigment orange 14, C.I. I. Pigment orange 16, C.I. I. Pigment orange 17, C.I. I. Pigment orange 24, C.I. I. Pigment orange 31, C.I. I. Pigment orange 34, C.I. I. Pigment orange 36, C.I. I. Pigment orange 38, C.I. I. Pigment orange 40, C.I. I. Pigment orange 42, C.I. I. Pigment orange 43, C.I. I. Pigment orange 46, C.I. I. Pigment orange 49, C.I. I. Pigment orange 51, C.I. I. Pigment orange 55, C.I. I. Pigment orange 59, C.I. I. Pigment orange 61, C.I. I. Pigment orange 63, C.I. I. Pigment orange 64, C.I. I. Pigment orange 65, C.I. I. Pigment orange 71, C.I. I. Pigment orange 73, C.I. I. And CI Pigment Red 242.
Of these orange pigments, orange pigments having a naphthol structure, a DPP structure or a condensed azo structure are preferred. Examples of orange pigments having a naphthol structure include C.I. I. Pigment Orange 38 (hereinafter referred to as “PO38”) is preferable, and orange pigments having a DPP structure include C.I. I. Pigment Orange 71 (hereinafter referred to as “PO71”) is preferable. Examples of orange pigments having a condensed azo structure include C.I. I. Pigment Red 242 (hereinafter referred to as “PR242”) is preferable.
It is particularly preferable to use PO38, PO71 and / or PR242 together with PR254 and PR177 because a red composition having high luminance and high contrast can be obtained.

  The total amount of the pigment in the solid content of the red composition of the present invention is preferably 10 to 50% by mass, particularly preferably 20 to 40% by mass. This is because if the amount is 10% by mass or more, the color reproducibility is high, and if it is 50% by mass or less, a developable and sufficiently sensitive composition can be obtained.

The pigment used in the present invention is preferably finer using a known method such as a salt milling method, an acid paste method, or an acid slurry method. This is because a red composition with higher contrast can be obtained.
The dispersion average particle size of the orange pigment is preferably 20 to 80 nm. A dispersion average particle size of 20 nm or more is preferable because the dispersion stability in the red composition is improved, and a dispersion average particle size of 80 nm or less is preferable because luminance and contrast are improved. The dispersion average particle size was measured with a Microtrac UPA particle size distribution analyzer (manufactured by Nikkiso Co., Ltd.) using a laser light scattering method.

The pigment described above is dispersed in a solvent together with a pigment dispersant to form a pigment dispersion. The mixing and dispersion for obtaining the pigment dispersion is performed using a mixing and dispersing machine such as a bead mill, a ball mill, a dissolver, a paint shaker, or a kneader.
The pigments may be mixed and dispersed independently, or two or more pigments may be combined and dispersed.
As the pigment dispersant, known polymer dispersants and low molecular dispersants can be used. Specifically, polymer dispersants such as modified polyurethane, modified polyacrylate, modified polyester, modified polyamide, phosphoric acid, and the like. Surfactants and pigment derivatives such as esters, alkylamines and polyoxyethylene alkylphenyl ethers can be mentioned. Among these, a polymer dispersant is preferable in the present invention, and specific product names include EFKA-4046, EFKA-4047, EFKA polymer 100, EFKA polymer 400, EFKA polymer 401, EFKA4300, and EFKA4330 (above, Ciba Specialty Chemicals), Disperbyk111, Disperbyk161, Disperbyk165, Disperbyk167, Disperbyk182, Disperbyk2000, Disperbyk2000, Disperbyk2001 (above, manufactured by Big Chemie), SOLSPER24000 techno Co., Ltd.)), and the like.
The amount of the dispersant in the solid content of the red composition of the present invention is preferably 0.5 to 30% by mass, particularly preferably 1 to 20% by mass. This is because a red composition having good dispersion stability and coating film properties can be obtained within the above range.

  The solvent is not particularly limited as long as it is generally used in a red composition for a color filter. Specifically, (mono or poly) alkylene glycol (mono or poly) alkyl ethers such as ethylene glycol monoethyl ether, propylene glycol monomethyl ether, diethylene glycol monoethyl ether, diethylene glycol dimethyl ether, diethylene glycol diethyl ether, dipropylene glycol dimethyl ether; Acetates such as 3-methyl-3-methoxybutyl acetate, ethylene glycol monomethyl ether acetate, ethylene glycol monoethyl ether acetate, propylene glycol monomethyl ether acetate, diethylene glycol monoethyl ether acetate, 3-methoxybutyl acetate, cyclohexanol acetate; propylene Glycoldia Diacetates such as tate and 1,3-butylene glycol diacetate; ethers such as tetrahydrofuran; ketones such as methyl ethyl ketone, cyclohexanone and 2-heptanone; methyl 2-hydroxypropionate, ethyl 3-hydroxypropionate, ethyl acetate , Esters such as n-butyl acetate, i-butyl acetate, i-butyl butyrate, n-butyl butyrate, ethyl 3-methoxypropionate, ethyl 3-ethoxypropionate and ethyl lactate; aromatic carbonization such as toluene and xylene Examples thereof include hydrogen. Among these solvents, propylene glycol monomethyl ether acetate, 3-methyl-3-methoxybutyl acetate, 3-methoxybutyl acetate, diethylene glycol diethyl ether and the like are preferable from the viewpoints of solubility, pigment dispersibility, and coatability. In addition, the said solvent can be used individually or in mixture of 2 or more types.

The red composition of the present invention preferably contains at least a pigment, a dispersant, a binder resin, a radiation sensitive compound, a photopolymerization initiator, and a solvent.
When a color filter is produced by the pigment dispersion method, for example, a negative photosensitive red composition is used. In this case, the photosensitive red composition comprises the above-described pigment dispersion, the binder resin dissolved in the solvent, the radiation-sensitive compound, the photopolymerization initiator, and the additive that is optionally added. Obtained by mixing and dispersing with a disperser.

  The binder resin used in the red composition of the present invention is not particularly limited, but since it is used in the production of color filters, it has heat resistance and resistance to organic solvents used in the production process. It is preferable that Specific examples include photosensitive or non-photosensitive resins such as epoxy resins, acrylic resins, urethane resins, polyester resins, polyimide resins, polyolefin resins, and gelatin.

  Among the above-described binder resins, particularly preferable binder resins include alkali-soluble resins having an acidic functional group such as a carboxyl group. As the alkali-soluble resin having a carboxyl group, a copolymer of a carboxyl group-containing unsaturated monomer and another copolymerizable ethylenically unsaturated monomer is preferable, and an epoxy group and an ethylenically unsaturated group are further included in the molecule. It is also preferable to add a compound having a group, such as glycidyl (meth) acrylate, and introduce an ethylenically unsaturated group in the side chain.

  Examples of the carboxyl group-containing unsaturated monomer include (meth) acrylic acid, crotonic acid, maleic acid, maleic anhydride, succinic acid mono [2- (meth) acryloyloxyethyl], and phthalic acid mono [2- (Meth) acryloyloxyethyl], ω-carboxypolycaprolactone mono (meth) acrylate and the like are preferable, and (meth) acrylic acid is particularly preferable. In addition, the carboxyl group-containing unsaturated monomer can be used alone or in combination of several kinds.

  Examples of the ethylenically unsaturated monomer include methyl (meth) acrylate, n-butyl (meth) acrylate, cyclohexyl (meth) acrylate, isobornyl (meth) acrylate, dicyclopentanyl (meth) acrylate, and dicyclopentenyl (meth) ) Acrylate, allyl (meth) acrylate, styrene, α-methylstyrene, benzyl (meth) acrylate, hydroxyethyl (meth) acrylate, 2-dimethylaminoethyl (meth) acrylate, 2-ethylhexyl (meth) acrylate, 2-hydroxyl (Meth) ethyl acrylate and the like and their macromonomers; N such as N-methylmaleimide, N-cyclohexylmaleimide, N-benzylmaleimide, N-phenylmaleimide and N-methylphenylmaleimide Mention may be made of the conversion maleimide, and the like. In addition, an ethylenically unsaturated monomer can be individual or can combine several types.

  Moreover, as an epoxy resin used as a binder resin, bisphenol A type epoxy resin, bisphenol F type epoxy resin, phenol novolac type epoxy resin, cresol novolac type epoxy resin, glycidyl (meth) acrylate, alicyclic epoxy (meth) acrylate, etc. Examples thereof include acrylic copolymers contained in the resin skeleton, and these resins can be used alone or in combination with an acrylic resin system.

  The amount of the binder resin in the solid content of the red composition of the present invention is preferably 5 to 60% by mass, particularly preferably 10 to 40% by mass. This is because within the above range, the coating property and the developing property are excellent.

  The radiation-sensitive compound means a compound that is reactive to radiation, and examples thereof include photoreactive compounds (such as UV-reactive compounds and visible light-reactive compounds) and electron beam-reactive compounds. Can do. More specifically, a monofunctional monomer having an unsaturated double bond and a polyfunctional monomer are exemplified. Monofunctional monomers include allyl acrylate, benzyl acrylate, butoxyethyl acrylate, butoxyethylene glycol acrylate, cyclohexyl acrylate, dicyclopentanyl acrylate, 2-ethylhexyl acrylate, glycerol acrylate, glycidyl acrylate, 2-hydroxyethyl acrylate, 2-hydroxy Propyl acrylate, isobornyl acrylate, isodexyl acrylate, isooctyl acrylate, lauryl acrylate, 2-methoxyethyl acrylate, methoxyethylene glycol acrylate, phenoxyethyl acrylate, stearyl acrylate, and those obtained by replacing the above acrylate with methacrylate Can be mentioned.

  Examples of the polyfunctional monomer include ethylene glycol diacrylate, diethylene glycol diacrylate, 1,4-butanediol diacrylate, 1,5-pentanediol diacrylate, 1,6-hexanediol diacrylate, and 1,3-propanediol. Bifunctional monomers such as acrylate, 1,4-cyclohexanediol diacrylate, 2,2-dimethylolpropane diacrylate, glycerol diacrylate, tripropylene glycol diacrylate; glycerol triacrylate, trimethylolpropane triacrylate, polyoxyethylation Trimethylolpropane triacrylate, pentaerythritol triacrylate, pentaerythritol tetraacrylate, triethylene glycol diamine , Polyoxypropyltrimethylolpropane triacrylate, butylene glycol diacrylate, 1,2,4-butanetriol triacrylate, 2,2,4-trimethyl-1,3-pentanediol diacrylate, diallyl fumarate, 1, Tri- or higher functional monomers such as 10-decanediol dimethyl acrylate, dipentaerythritol pentaacrylate, dipentaerythritol hexaacrylate, carboxylic acid-modified dipentaerythritol pentaacrylate, and the above acrylate replaced with methacrylate, and γ-methacrylate Examples include loxypropyltrimethoxysilane and 1-vinyl-2-pyrrolidone. In the present invention, the above monofunctional monomer and polyfunctional monomer can be used as one kind or a mixture of two or more kinds or as a mixture with other compounds.

  The amount of the radiation sensitive compound in the solid content of the red composition of the present invention is preferably 5 to 60% by mass, particularly preferably 10 to 40% by mass. It is because it will become excellent in a sensitivity, developability, coating-film hardness, etc. if it is in the said range.

In addition, the red composition for a color filter of the present invention includes, as additives, a photopolymerization initiator, a sensitizer, a polymerization terminator, a chain transfer agent, a leveling agent, a plasticizer, a surfactant, an antifoaming agent, and the like. Used as needed.
Specific examples of the photopolymerization initiator include benzophenone, Michler's ketone (4,4′-bisdimethylaminobenzophenone), 4,4′-bisdiethylaminobenzophenone, 4-methoxy-4′-dimethylaminobenzophenone, 2-ethylanthraquinone, Aromatic ketones such as phenanthrene, benzoin ethers such as benzoin methyl ether, benzoin ethyl ether and benzoin phenyl ether, benzoins such as methyl benzoin and ethyl benzoin, 2- (o-chlorophenyl) -4,5-phenylimidazole dimer 2- (o-chlorophenyl) -4,5-di (m-methoxyphenyl) imidazole dimer, 2- (o-fluorophenyl) -4,5-diphenylimidazole dimer, 2- (o-methoxy) Phenyl) -4,5-diph Nylimidazole dimer, 2,4,5-triarylimidazole dimer, 2- (o-chlorophenyl) -4,5-di (m-methylphenyl) imidazole dimer, 2-benzyl-2-dimethyl Amino-1- (4-morpholinophenyl) -butanone, 2-trichloromethyl-5-styryl-1,3,4-oxadiazole, 2-trichloromethyl-5- (p-cyanostyryl) -1,3 , 4-oxadiazole, halomethylthiazole compounds such as 2-trichloromethyl-5- (p-methoxystyryl) -1,3,4-oxadiazole, 2,4-bis (trichloromethyl) -6-p -Methoxystyryl-S-triazine, 2,4-bis (trichloromethyl) -6- (1-p-dimethylaminophenyl-1,3-butadienyl) -S-tri Gin, 2-trichloromethyl-4-amino-6-p-methoxystyryl-S-triazine, 2- (naphth-1-yl) -4,6-bis-trichloromethyl-S-triazine, 2- (4- Ethoxy-naphth-1-yl) -4,6-bis-trichloromethyl-S-triazine, 2- (4-butoxy-naphth-1-yl) -4,6-bis-trichloromethyl-S-triazine, etc. Halomethyl-S-triazine compounds, 2,2-dimethoxy-1,2-diphenylethane-1-one, 2-methyl-1- [4- (methylthio) phenyl] -2-morpholinopropanone, 1,2- Benzyl-2-dimethylamino-1- (4-morpholinophenyl) -butanone-1,1-hydroxy-cyclohexyl-ketone, benzyl, benzoylbenzoic acid, Methyl benzoylbenzoate, 4-benzoyl-4'-methyldiphenyl sulfide, benzylmethyl ketal, dimethylaminobenzoate, isoamyl P-dimethylaminobenzoate, 2-n-butoxyethyl-4-dimethylaminobenzoate, 2-chlorothioxanthone, 2 , 4 Diethylthioxanthone, 2,4 Dimethylthioxanthone, Isopropylthioxanthone, Speed Cure BMS (Lambson), Irgacure 184 (Ciba Specialty Chemicals), Irgacure 369 (Ciba Specialty Chemicals), Irgacure 379 (Ciba Specialty Chemicals), Irgacure 651 (Ciba Specialty Chemicals), Irgacure 819 (Ciba Specialty Chemicals) Irgacure 907 (Ciba Specialty Chemicals), Irgacure OXE01 (Ciba Specialty Chemicals), Irgacure OXE02 (Ciba Specialty Chemicals), Darocur TPO (Ciba Specialty Chemicals), etc. The photoinitiator of this is mentioned. In this invention, these photoinitiators can be used individually or in mixture of 2 or more types.
The amount of the photopolymerization initiator used in the solid component of the photosensitive red composition of the present invention is preferably 3% by mass to 40% by mass, particularly preferably 10% by mass to 30% by mass. This is because within this range, a photosensitive red composition having good sensitivity and a fine pattern can be obtained.

  In addition, an aliphatic or aromatic mono- or polyfunctional thiol compound or an aromatic amine compound can be used as a hydrogen donor in combination with a photopolymerization initiator. The amount of the hydrogen donor used in the solid component of the photosensitive red composition of the present invention is in the range of 0.5% by mass to 30% by mass, particularly in the range of 2% by mass to 20% by mass. It is preferable in terms of sensitivity.

  In addition, surfactants, antifoaming agents, silane coupling agents, chain transfer agents, and the like can be added as additives. Examples of the surfactant that can be used include polyoxyethylene lauryl ether, polyoxyethylene stearyl ether, polyoxyethylene oleyl ether, polyoxyethylene octylphenyl ether, polyoxyethylene nonylphenyl ether, polyethylene glycol dilaurate, and polyethylene glycol. Examples include distearate, sorbitan fatty acid esters, fatty acid-modified polyesters, and tertiary amine-modified polyurethanes.

The photosensitive red composition of the present invention prepared as described above is used, for example, for spin coating, casting coating, and dipping on a glass substrate for a color filter having a light shielding layer patterned. Coating is performed by a known coating method such as coating, roll coating, especially die coating, and vacuum baking is performed until the degree of vacuum reaches about 0.1 to 1.0 torr, for example, 0.2 torr, and about 0.5 to 4 μm ( A coating film having a dry film thickness is obtained. The obtained coating film is exposed by irradiating it with ultraviolet light having a light amount of about 10 to 500 mJ / cm ² by a high pressure mercury lamp, an ultrahigh pressure mercury lamp or the like through a negative photomask for forming a target pixel. After the exposure, the photocured coating film is developed by a spray method or a dipping method using a known alkaline developer, and the unexposed portion is dissolved to obtain a pixel corresponding to the target color. If necessary, after development, post-curing can be performed at a temperature of about 200 to 250 ° C. for about 10 to 60 minutes. A target color filter can be obtained by repeating the above-described step of obtaining the pixels by the number of colors required for the color filter. The above color filter may be manufactured as a red color filter having only red pixels. Usually, in addition to the red pixels formed using the photosensitive red composition of the present invention, each of the green and blue pixels. Are arranged on a glass substrate for a color filter on which a light shielding layer is patterned.

The color filter manufactured as described above preferably has chromaticity coordinates (x, y) in the XYZ color system chromaticity diagram in the following range under the condition of a C light source and a 2 ° visual field.
0.630 ≦ x ≦ 0.680
0.310 ≦ y ≦ 0.350
If this range has chromaticity coordinates (x, y), high color reproducibility and transmittance are compatible when combined with a backlight, and television display is achieved when combined with GREEN (green) and BLUE (blue). This is preferable because the chromaticity is suitable.

Examples The present invention will be described in more detail with reference to examples, but the present invention is not limited to these examples.
The chromaticity x, chromaticity y, luminance Y and contrast of the photosensitive red composition were evaluated according to the following methods.
<Chromaticity x, chromaticity y, and luminance Y>
Using an Olympus Co., Ltd. OSP-SP200 microspectrophotometer, the chromaticity x, chromaticity y and tristimulus Y (brightness Y) values defined in JIS Z8701 were measured as luminance Y. . The measurement conditions were as follows: the light source was a C light source, the illumination magnification was 20 times, and the 7 (50 μm).
<Contrast>
The contrast ratio of the coating film produced using the resist was measured as follows.
FIG. 1 is a schematic diagram illustrating a contrast measurement method. In FIG. 1, the light 2 emitted from the backlight unit 1 for liquid crystal display passes through the first polarizing plate 3, is polarized, passes through the cured coating film 4 of the colored composition applied on the glass substrate, It reaches the second polarizing plate 5. If the polarizing plates of the first polarizing plate 3 and the second polarizing plate 5 are parallel, the light is transmitted through the second polarizing plate 5, but if the polarizing plates 3 and 5 are orthogonal, the light is transmitted. Is blocked by the second polarizing plate 5. However, when the light polarized by the first polarizing plate 3 passes through the cured coating film 4 of the colored composition, if the light is scattered by the pigment particles and the polarized light is partially displaced, the polarizing plate 3 When 5 and 5 are parallel, the amount of light passing through the second polarizing plate 5 is reduced, and when the polarizing plates 3 and 5 are orthogonal, a part of the light passes through the second polarizing plate 5. The luminance of the transmitted light was measured with a luminance meter 6, and the ratio (contrast ratio) between the luminance when the polarizing plates 3 and 5 were parallel and the luminance when they were orthogonal was calculated.
Contrast ratio = {parallel luminance (cd / m ² )} / {orthogonal luminance (cd / m ² )}
For luminance measurement, a luminance meter (product name “LS-100” manufactured by Minolta), a polarizing plate (product name “NPF-G1220DU” manufactured by Nitto Denko Corporation) as a polarizing plate, backlight (Toshiba Corporation) Product name, “Mellow 5DFL10EX-DH”, color temperature 6500K).

Production Example 1 Binder resin: Synthesis of benzyl methacrylate copolymer resin benzyl methacrylate 30 g (0.16 mol), methyl methacrylate 38 g (0.38 mol), methacrylic acid 18 g (0.21 mol) and t-butyl-oxy- A mixture of 10 g of 2-ethylhexanoate (trade name “Perbutyl O”, manufactured by NOF Corporation) is placed in a polymerization tank containing 150 g of propylene glycol monomethyl ether acetate at 100 ° C. for 3 hours under a nitrogen stream. It was dripped.
After completion of the dropwise addition, the polymer solution was obtained by further heating for 3 hours. The weight average molecular weight (Mw) of this polymer solution was 8,000 in terms of polystyrene.
Next, 14 g (0.10 mol) of glycidyl methacrylate, 0.2 g of triethylamine and 0.05 g of p-methoxyphenol were added to the obtained polymer solution, and the main chain methacrylic acid was heated by heating at 110 ° C. for 10 hours. The reaction between the carboxylic acid group and the epoxy group of glycidyl methacrylate was carried out. During the reaction, air was bubbled into the reaction solution in order to prevent polymerization of glycidyl methacrylate. The reaction was followed by measuring the acid value of the solution. The obtained reaction solution had a solid content (NV) of 40% by mass, an acid value (AV) of 75 mgKOH / g, and a weight average molecular weight (Mw) of 10,000 in terms of polystyrene.

Production Example 2 Preparation of Clear Resist Solution 40 g of binder resin obtained in Production Example 1, 16 g of dipentaerythritol hexaacrylate (DPHA) which is a radiation sensitive compound (photopolymerizable monomer), photopolymerization initiator 2-benzyl-2 -Dimethylamino-1- (4-morpholinophenyl) butan-1-one (trade name “Irgacure 369”, manufactured by Ciba Specialty Chemicals) 8 g, propylene glycol monomethyl ether acetate (PGMEA) 36 g were blended, The mixture was stirred for 1 hour to prepare a clear resist solution.

Production Examples 3 to 9 Preparation of pigment dispersions N1 to N7 As a dispersant, 7.2 g of Ajisper PB821 (manufactured by Ajinomoto Fine-Techno Co., Ltd.) and 80.8 g of propylene glycol monomethyl ether acetate (PGMEA) were blended uniformly using a dissolver. Then, 12 g of PR254 was added and stirred for 1 hour to prepare a preliminary dispersion. Next, this preliminary dispersion was dispersed with a paint shaker for 3 hours using 0.3 mm zirconia beads to prepare a pigment dispersion Nl.
The pigments other than PR254 were also dispersed in the same manner to prepare pigment dispersions N2 to N7. In addition, when the dispersion average particle diameter of each pigment in the pigment dispersions Nl to N7 was measured with a Microtrac UPA particle size distribution meter (manufactured by Nikkiso Co., Ltd.), N1 was 60 nm, N2 was 45 nm, N3 was 25 nm, and N4 was 25 nm, N5 was 20 nm, N6 was 25 nm, and N7 was 20 nm.
Nl: PR254, N2: PR177, N3: PY139, N4: PY150, N5: PO38, N6: PO71, N7: PR242

Examples 1-3 and Comparative Examples 1-2
100 g of the pigment dispersions Nl to N7 obtained in Production Examples 3 to 9 (adjusted so as to have the pigment ratio in Table 1), 42 g of the clear resist solution obtained in Production Example 2, and propylene glycol monomethyl ether acetate (PGMEA) ) Was mixed and stirred to prepare negative photosensitive red compositions of Examples 1 to 3 and Comparative Examples 1 and 2.
Next, each photosensitive red composition obtained in Examples 1 to 3 and Comparative Examples 1 and 2 is applied on a transparent glass base plate for a color filter with a spin coater, and then applied to a hot plate at 70 ° C. Then, a photosensitive red composition coating film was obtained by heat treatment (pre-baking) for 3 minutes. The photosensitive red composition was applied by adjusting the spin coater rotation speed so that the chromaticity of the pattern was x = 0.648 with a C light source. Next, the entire surface of the coating film was exposed with an amount of light of 60 mj in terms of i-line using an exposure machine equipped with an ultra-high pressure mercury lamp, and then developed with 0.05% potassium hydroxide aqueous solution (optionally with a surfactant added). The patterning substrate was obtained by performing pure water cleaning. The obtained patterned substrate was held in a hot air oven at 230 ° C. for 30 minutes to cure the acrylic resin. From the above, a substrate on which a red cured coating film was formed was produced.
Using the above substrate, chromaticity x, chromaticity y, luminance Y, and contrast were evaluated by the above measuring method. The evaluation results are shown in Table 1.

  As is clear from Table 1, the photosensitive red compositions of Examples 1 to 3 containing PR254, PR177 and an orange pigment were excellent in both luminance and contrast. On the other hand, the photosensitive red composition of Comparative Example 1 had high contrast but low luminance, and the photosensitive red composition of Comparative Example 2 had improved brightness compared to Comparative Example 1, but had low contrast.

  The photosensitive red composition of the present invention is suitably used for a color filter, and the color filter having the photosensitive red composition is a high-definition color filter used for a television or the like, particularly a large glass of a liquid crystal display device such as a large television. It is suitably used as a color filter having a substrate.

DESCRIPTION OF SYMBOLS 1 Backlight unit for liquid crystal display 2 Light 3 1st polarizing plate 4 Curing coating film 5 2nd polarizing plate 6 Luminance meter

Claims (8)

  C. I. Pigment red 254, C.I. I. A red composition for a color filter, containing Pigment Red 177 and an orange pigment.   In a total of 100 parts by mass of pigment, C.I. I. Pigment Red 254 is 10 to 60 parts by mass, C.I. I. The red composition for a color filter according to claim 1, wherein the pigment red 177 is 20 to 80 parts by mass and the orange pigment is 10 to 49 parts by mass.   The red composition for a color filter according to claim 1 or 2, wherein the orange pigment has a dispersion average particle diameter of 20 to 80 nm.   The red composition for a color filter according to any one of claims 1 to 3, wherein the orange pigment has a naphthol structure, a DPP structure, or a condensed azo structure.   The orange pigment is C.I. I. Pigment orange 38, C.I. I. Pigment orange 71 and / or C.I. I. The red composition for a color filter according to claim 1, which is CI Pigment Red 242.   The red composition for a color filter according to claim 1, comprising at least a pigment, a dispersant, a binder resin, a radiation sensitive compound, a photopolymerization initiator, and a solvent.   The color filter which has the red composition for color filters in any one of Claims 1-6. The color filter according to claim 7, wherein the chromaticity coordinates (x, y) in the XYZ color system chromaticity diagram are in the following range under the condition of a C light source and a 2 ° visual field.
0.630 ≦ x ≦ 0.680
0.310 ≦ y ≦ 0.350

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