JP2011090313A - Method for producing coloring material for color filter, coloring material for color filter produced by the method, and color filter - Google Patents

Abstract

<P>PROBLEM TO BE SOLVED: To provide a coloring material for a color filter compatibly having required characteristics of a high contrast ratio, lightness and the like required for the color filter and fluidity and stability with passage of time. <P>SOLUTION: The method for producing the coloring material for the color filter includes a step (A) for supplying and dispersing a pigment composition including a pigment, a pigment derivative and a liquid medium to a wet dispersion device using a medium having ≤0.3 mmϕ particle diameter, having no medium separation mechanism of a slit system and a screen system and having only a medium separation mechanism of a centrifugal separation system and a step (B) for adding and mixing a monomer and/or a resin to the pigment composition obtained in the step (A) if needed. The color filter has a filter segment formed by using the coloring material for the color filter manufactured by the method. <P>COPYRIGHT: (C)2011,JPO&INPIT

Description

The present invention relates to a method for producing a colorant used for forming a filter segment constituting a color filter used in a color liquid crystal display device and a solid-state imaging device, a colorant for color filter produced by the production method, and the color filter. The present invention relates to a color filter obtained by using a coloring material.

In the liquid crystal display device, a liquid crystal layer sandwiched between two polarizing plates controls the amount of light passing through the first polarizing plate by controlling the degree of polarization of light passing through the first polarizing plate. The type using twisted nematic (TN) type liquid crystal that performs display by the above method is the mainstream, and color display is enabled by providing a color filter between the two polarizing plates. Currently, as a method for producing a color filter, a method called a pigment dispersion method in which a pigment having excellent light resistance and heat resistance is used as a colorant is mainly used. However, a color filter in which an organic pigment is dispersed is generally based on pigment particles. There is a problem that the degree of polarization controlled by the liquid crystal is disturbed due to light scattering or the like. That is, there is a phenomenon in which light leaks when light must be blocked (OFF state) or transmitted light attenuates when light must be transmitted (ON state). The above luminance ratio is called the contrast ratio.

In general, it is difficult to obtain a stable dispersion by dispersing fine pigment particles in a colorant carrier such as varnish in the pigment dispersion method, and the pigment particles in the dispersion often aggregate over time. A color filter formed using a dispersion in which pigment particles are aggregated remarkably lowers the contrast ratio. Therefore, the pigment may be stable fine particles without aggregation and easy to handle. It is desired.
In recent years, the required characteristics such as contrast ratio and flow stability required for colorants for color filters have become very high performance, and techniques for finely dispersing pigments are important.

In the fine dispersion of pigment, generally, in a disperser called a sand mill, a sand grinder, a dyno mill, a pearl mill, etc., the pigment composition is processed by impact force, shear force, friction force obtained by vigorously stirring the media with a stirring mechanism. Is done by.
Further, as a method of finely dispersing the pigment, using a media stirring type disperser, without using a pigment derivative, only the pigment is dispersed in multiple stages, and the diameter of the media in each stage is sequentially reduced, and A method of performing dispersion in a circulation manner has been proposed (see, for example, Patent Document 1).

JP 11-352319 A

It is important to finely disperse the pigment to the submicron region of 1 μm or less in order to satisfy the performance required for the color filter, but the dispersion using fine media that is considered effective for fine dispersion of the pigment. When only the pigment is dispersed in the liquid medium by a machine, the viscosity may be increased by the particles dispersed in the submicron region. In addition, the contrast ratio and brightness may be reduced due to reaggregation of the pigment.
In other words, with the conventional technology, it is very difficult to achieve both the required characteristics such as the high contrast ratio and high brightness required for the color filter, the fluidity and the stability over time in the color filter colorant. Met.

The method for producing a color filter coloring material of the present invention does not have a slit-type and screen-type media separation mechanism using a medium having a particle size of 0.3 mmφ or less, but has only a centrifugal separation type media separation mechanism. It includes a step (A) of supplying and dispersing a pigment composition containing a pigment, a pigment derivative, and a liquid medium to a wet disperser. The method for producing a color filter coloring material of the present invention may further include a step (B) of adding and mixing a monomer and / or a resin to the dispersion of the pigment composition obtained in the step (A).
Moreover, the color filter of this invention comprises the filter segment formed using the coloring material for color filters manufactured by the said manufacturing method, It is characterized by the above-mentioned.

According to the method for producing a color filter coloring material of the present invention, a combination of fine media having a particle size of 0.3 mmφ or less and a pigment derivative does not have a slit-type and screen-type media separation mechanism, and is a centrifugal separation type. In order to disperse the pigment in the liquid medium by the wet disperser having only the media separation mechanism, the effect of each of the fine media and the pigment derivative is greatly exceeded, and the pigment is stably re-aggregated to the submicron region of 1 μm or less. A color filter colorant that can be finely dispersed and has low viscosity and high fluidity is obtained. Further, by using the color filter coloring material produced by the production method of the present invention, a color filter having a high contrast ratio and high brightness can be obtained.

Hereinafter, the present invention will be described in detail.
The color filter coloring material is a pigment that is added to a wet disperser that has only a centrifugal separation type media separation mechanism, without a slit type or screen type media separation mechanism using a medium having a particle size of 0.3 mmφ or less. It can be produced by supplying and dispersing a pigment composition containing a pigment derivative, a liquid medium, and if necessary, a resin, a monomer, a dispersant, an additive and the like. Resin, monomer, dispersant, additive, etc. are added and mixed after dispersing the pigment composition containing pigment, pigment derivative, and liquid medium to a wet disperser using media with a particle size of 0.3 mmφ or less. May be.
Wet dispersers that use media and do not have slit-type and screen-type media separation mechanisms, but only centrifugal-type media separation mechanisms include horizontal, vertical, and annular types of cylindrical dispersers ( For example, various dispersers using media such as a ball mill, a sand mill, an attritor, and a vibration mill can be used.

The rotary shaft of this wet disperser is provided with stirring blades having various shapes, and disk type, pin type, etc. are known. Among them, those equipped with rotor pins are more effective for the present invention. Preferred for greater prominence.
In addition, as a media separation mechanism of this wet disperser, there are a centrifugal separation method, a slit method (gap separator method), a screen method, and the like. In the present invention, only a centrifugal separation method is used. This is because it is very difficult to manufacture slits or screens capable of separating minute media having a particle size of 0.3 mmφ or less because of machining accuracy, and there is a possibility of clogging when supplying a pigment composition. . In addition, when using fine media having a particle size of 0.3 mmφ or less, particularly 0.1 mmφ or less, the filtration rate becomes very slow when separating the fine media by a slit or screen method, This is because it is difficult to increase the supply amount.

For example, Super Apex Mill (manufactured by Kotobuki Giken Kogyo Co., Ltd.), Ultra Apex Mill (Kotobuki Giken Co., Ltd.), which has only a media separation mechanism by centrifugation, without a media separation mechanism of rotor pin, slit type and screen type. Manufactured by Kogyo Co., Ltd.).
Moreover, the media filling rate in the disperser having good dispersion efficiency is preferably 50 to 100%, more preferably 60 to 80%.
The material of the media is not particularly limited, and commonly used glass, steel, stainless steel, ceramics, zircon, zirconia and the like can be mentioned. The media particle size must be 0.3 mmφ or less, and usually 0.01 mmφ or more in order to achieve fine dispersion, a sizing effect, and a high contrast ratio. Furthermore, the preferable particle diameter of the micro media is 0.1 mmφ or less, and it is particularly preferable to use micro media of 0.05 mmφ to 0.01 mmφ because the effect becomes very large.

Next, the pigment composition supplied to the wet disperser will be described.
As the pigment contained in the pigment composition, organic or inorganic pigments can be used alone or in admixture of two or more. The pigment is preferably a pigment having a high color developability and a high heat resistance, particularly a pigment having a high heat decomposition resistance, and an organic pigment is usually used.
Below, the specific example of the organic pigment which can be used for a pigment composition is shown by a color index number.
Examples of the red colorant for forming the red filter segment include CI Pigment Red 7, 9, 14, 41, 48: 1, 48: 2, 48: 3, 48: 4, 81: 1, 81: 2, 81: 3, 97, 122, 123, 146, 149, 168, 177, 178, 180, 184, 185, 187, 192, 200, 202, 208, 210, 215, 216, 217, 220, 223, 224, Red pigments such as 226, 227, 228, 240, 246, 254, 255, 264, and 272 can be used. A yellow pigment and an orange pigment can be used in combination with the red composition.

Examples of yellow colorants for forming yellow filter segments include CI Pigment Yellow 1, 2, 3, 4, 5, 6, 10, 12, 13, 14, 15, 16, 17, 18, 20, 24, 31, 32, 34, 35, 35: 1, 36, 36: 1, 37, 37: 1, 40, 42, 43, 53, 55, 60, 61, 62, 63, 65, 73, 74, 77, 81, 83, 86, 93, 94, 95, 97, 98, 100, 101, 104, 106, 108, 109, 110, 113, 114, 115, 116, 117, 118, 119, 120, 123, 125, 126, 127, 128, 129, 137, 138, 139, 147, 148, 150, 151, 152, 153, 154, 155, 156, 161, 162, 164, 166, 167, Use yellow pigments such as 68, 169, 170, 171, 172, 173, 174, 175, 176, 177, 179, 180, 181, 182, 185, 187, 188, 193, 194, 199, 213, 214, etc. Can do.

As the orange coloring material for forming the orange filter segment, for example, an orange pigment such as CI Pigment orange 36, 43, 51, 55, 59, 61, 71, 73 can be used.
As the green colorant for forming the green filter segment, for example, a green pigment such as CI Pigment Green 7, 10, 36, 37 can be used. A yellow pigment can be used in combination with the green composition.
Examples of the blue colorant for forming the blue filter segment include blue colors such as CI Pigment Blue 15, 15: 1, 15: 2, 15: 3, 15: 4, 15: 6, 16, 22, 60, 64, etc. Pigments can be used. Purple pigments such as CI Pigment Violet 1, 19, 23, 27, 29, 30, 32, 37, 40, 42, 50 can be used in combination with the blue composition.

For the cyan colorant for forming the cyan filter segment, for example, a blue pigment such as CI Pigment Blue 15: 1, 15: 2, 15: 4, 15: 3, 15: 6, 16, 81 or the like is used. it can.
As a magenta colorant for forming a magenta color filter segment, for example, purple pigments and red pigments such as CI Pigment Violet 1, 19, CI Pigment Red 144, 146, 177, 169, 81 can be used. A yellow pigment can be used in combination with the magenta composition.
Examples of the black pigment for the resin black matrix include carbon black, titanium black, aniline black, anthraquinone black pigment, perylene black pigment, specifically CI Pigment black 6, 7, 12, 20, 31, 32, etc. Among them, carbon black is preferable. Carbon black may be surface-treated with a resin or the like.
Inorganic pigments include titanium oxide, barium sulfate, zinc white, lead sulfate, yellow lead, zinc yellow, red bean (red iron (III) oxide), cadmium red, ultramarine, bitumen, chromium oxide green, cobalt green, amber And synthetic iron black. Inorganic pigments are used in combination with organic pigments in order to ensure good coatability, sensitivity, developability and the like while maintaining a balance between saturation and lightness.
The pigment composition may contain a dye within a range that does not reduce heat resistance for color matching.

The pigment derivative contained in the pigment composition is a compound represented by the following general formula (2), and there are those having a basic substituent and those having an acidic substituent.
Formula (2)
AB
A: Organic pigment residue B: Basic substituent or acidic substituent

In the formula (2), the organic pigment constituting the organic pigment residue of A includes diketopyrrolopyrrole pigments, azo pigments such as azo, disazo, polyazo, copper phthalocyanine, halogenated copper phthalocyanine, metal-free phthalocyanine, etc. Phthalocyanine pigments, aminoanthraquinone, diaminodianthraquinone, anthrapyrimidine, flavantron, anthanthrone, indanthrone, pyranthrone, violanthrone, anthraquinone pigment, quinacridone pigment, dioxazine pigment, perinone pigment, perylene pigment, thioindigo Pigments, isoindoline pigments, isoindolinone pigments, quinophthalone pigments, selenium pigments, metal complex pigments, and the like.

式（４）

式（５）

式（６）

式（７）

式（８）

In the formula (2), examples of the basic substituent of B include substituents represented by the following formula (3), formula (4), formula (5), and formula (6). , Substituents represented by formula (7) and formula (8).
Formula (3)

Formula (4)

Formula (5)

Formula (6)

Formula (7)

Formula (8)

X: represents —SO 2 —, —CO—, —CH 2 NHCOCH 2 —, —CH 2 — or a direct bond.
n represents an integer of 1 to 10.
R1, R2: each independently an alkyl group having 1 to 36 carbon atoms which may be substituted, an alkenyl group having 2 to 36 carbon atoms which may be substituted, an optionally substituted phenyl group, or R1 and R2 together with R2 represents an optionally substituted heterocycle containing further nitrogen, oxygen or sulfur atoms.
R3: represents an optionally substituted alkyl group having 1 to 36 carbon atoms, an optionally substituted alkenyl group having 2 to 36 carbon atoms, or an optionally substituted phenyl group.
R4, R5, R6, R7: each independently a hydrogen atom, an optionally substituted alkyl group having 1 to 36 carbon atoms, an optionally substituted alkenyl group having 2 to 36 carbon atoms, or an optionally substituted group Represents a good phenyl group.
Y: -NR8-Z-NR9- or a direct bond.
R8 and R9 each independently represent a hydrogen atom, an optionally substituted alkyl group having 1 to 36 carbon atoms, an optionally substituted alkenyl group having 2 to 36 carbon atoms, or an optionally substituted phenyl group. .
Z: represents an optionally substituted alkylene group having 1 to 36 carbon atoms, an optionally substituted alkenylene group having 2 to 36 carbon atoms, or an optionally substituted phenylene group.

式（１０）

R: The substituent shown by Formula (9) or the substituent shown by Formula (10) is represented.
Q: represents a hydroxyl group, an alkoxyl group, a substituent represented by the formula (9) or a substituent represented by the formula (10).
Formula (9)

Formula (10)

M: represents a hydrogen atom, calcium atom, barium atom, strontium atom, manganese atom or aluminum atom.
i: represents the valence of M.
R10, R11, R12, R13: each independently a hydrogen atom, an optionally substituted alkyl group having 1 to 36 carbon atoms, an optionally substituted alkenyl group having 2 to 36 carbon atoms, or optionally substituted Represents a good phenyl group or polyoxyalkylene group.

Examples of the amine component used for forming the substituent represented by the formulas (3) to (6), (9), and (10) include dimethylamine, diethylamine, N, N-ethylisopropyl, and the like. Amine, N, N-ethylpropylamine, N, N-methylbutylamine, N, N-methylisobutylamine, N, N-butylethylamine, N, N-tert-butylethylamine, diisopropylamine, dipropylamine, N, N-sec-butylpropylamine, dibutylamine, disec-butylamine, diisobutylamine, N, N-isobutyl-sec-butylamine, diamylamine, diisoamylamine, dihexylamine, di (2-ethylhexyl) amine, dioctylamine N, N-methyloctadecylamine, didecyla , Diallylamine, N, N-ethyl-1,2-dimethylpropylamine, N, N-methylhexylamine, dioleylamine, distearylamine, N, N-dimethylaminomethylamine, N, N-dimethylaminoethylamine, N, N-dimethylaminoamylamine, N, N-dimethylaminobutylamine, N, N-diethylaminoethylamine, N, N-diethylaminopropylamine, N, N-diethylaminohexylamine, N, N-diethylaminobutylamine, N, N -Diethylaminopentylamine, N, N-dipropylaminobutylamine, N, N-dibutylaminopropylamine, N, N-dibutylaminoethylamine, N, N-dibutylaminobutylamine, N, N-diisobutylaminopentylamine, N, N- Tyl-laurylaminopropylamine, N, N-ethylhexylaminoethylamine, N, N-distearylaminoethylamine, N, N-dioleylaminoethylamine, N, N-distearylaminobutylamine, piperidine, 2-pipecoline, 3 -Pipecoline, 4-Pipecoline, 2,4-Lupetidine, 2,6-Lupetidine, 3,5-Lupetidine, 3-Piperidinemethanol, Pipecolic acid, Isonipecotic acid, Methyl isonicopetinate, Ethyl isonicopetinate, 2-Piperidinethanol, Pyrrolidine 3-hydroxypyrrolidine, N-aminoethylpiperidine, N-aminoethyl-4-pipecholine, N-aminoethylmorpholine, N-aminopropylpiperidine, N-aminopropyl-2-pipecoline, N-aminopropyl-4 -Pipecoline, N-aminopropylmorpholine, N-methylpiperazine, N-butylpiperazine, N-methylhomopiperazine, 1-cyclopentylpiperazine, 1-amino-4-methylpiperazine, 1-cyclopentylpiperazine and the like.

The amine component used to form the sulfonic acid amine salt of formula (8) may be any of primary, secondary, tertiary and quaternary amines. For example, the primary amine has a side chain. Hexylamine, heptylamine, octylamine, nonylamine, decylamine, undecylamine, dodecylamine, tridecylamine, tetradecylamine, pentadecylamine, hexadecylamine, heptadecylamine, octadecylamine, nonadecylamine, Examples include amines such as eocosylamine, or unsaturated amines corresponding to the number of carbon atoms.

Secondary, tertiary and quaternary amines include dioleylamine, distearylamine, dimethyloctylamine, dimethyldecylamine, dimethyllaurylamine, dimethylstearylamine, dilaurylmonomethylamine, trioctylamine, dimethyldidodecylammonium chloride, Dimethyl dioleyl ammonium chloride, dimethyl didecyl ammonium chloride, dimethyl dioctyl ammonium chloride, trimethyl stearyl ammonium chloride, dimethyl distearyl ammonium chloride, trimethyl decyl ammonium chloride, trimethyl hexadecyl ammonium chloride, trimethyl octadecyl ammonium chloride, dimethyl dodecyl tetradecyl ammonium chloride , Dimethyl hexadecyl octadec Ammonium chloride, and the like.
Further, when any of R10, R11, R12 and R13 in the formula (8) represents a polyoxyalkylene group, examples thereof include a polyoxyethylene group and a polyoxypropylene group.

ＣｕＰｃは、銅フタロシアニン残基を表す。
化合物２

化合物３

Specific examples of pigment derivatives are shown below with compound numbers.
Compound 1

CuPc represents a copper phthalocyanine residue.
Compound 2

Compound 3

化合物５

化合物６

ＣｕＰｃは、銅フタロシアニン残基を表す。 Compound 4

Compound 5

Compound 6

CuPc represents a copper phthalocyanine residue.

化合物８

化合物９

Compound 7

Compound 8

Compound 9

The blending amount of the pigment derivative in the pigment composition is preferably 1 to 20 parts by weight, more preferably 5 to 15 parts by weight with respect to 100 parts by weight of the pigment. When the blending amount of the pigment derivative is less than 1 part by weight, the dispersion effect is insufficient, and when it is more than 20 parts by weight, the excess pigment derivative may affect the dispersion.

Further, the liquid medium contained in the pigment composition is not particularly limited. For example, cyclohexanone, ethyl cellosolve acetate, butyl cellosolve acetate, 1-methoxy-2-propyl acetate, diethylene glycol dimethyl ether, ethylbenzene, ethylene glycol diethyl ether, xylene , Ethyl cellosolve, methyl-n amyl ketone, propylene glycol monomethyl ether toluene, methyl ethyl ketone, ethyl acetate, methanol, ethanol, isopropyl alcohol, butanol, isobutyl ketone, petroleum solvents, etc., and these may be used alone or in combination. Can do.
Furthermore, these solvents make it easy to form a filter segment by sufficiently dispersing the pigment in the pigment carrier and applying it onto a transparent substrate such as a glass substrate so that the dry film thickness is 0.2 to 5 μm. Therefore, the pigment composition dispersion obtained in the step (A) can be added and mixed.

In the step (A), the pigment composition may further contain a resin. Moreover, the method for producing a color filter coloring material of the present invention may further include a step (B) of adding and mixing a monomer and / or a resin to the dispersion of the pigment composition obtained in the step (A).
As monomers, methyl (meth) acrylate, ethyl (meth) acrylate, 2-hydroxyethyl (meth) acrylate, 2-hydroxypropyl (meth) acrylate, cyclohexyl (meth) acrylate, β-carboxyethyl (meth) acrylate, polyethylene Glycol di (meth) acrylate, 1,6-hexanediol di (meth) acrylate, triethylene glycol di (meth) acrylate, tripropylene glycol di (meth) acrylate, trimethylolpropane tri (meth) acrylate, pentaerythritol tri ( (Meth) acrylate, 1,6-hexanediol diglycidyl ether di (meth) acrylate, bisphenol A diglycidyl ether di (meth) acrylate, neopentylglycol Rudiglycidyl ether di (meth) acrylate, dipentaerythritol hexa (meth) acrylate, tricyclodecanyl (meth) acrylate, ester acrylate, (meth) acrylic acid ester of methylolated melamine, epoxy (meth) acrylate, urethane acrylate, etc. Acrylic acid esters and methacrylic acid esters, (meth) acrylic acid, styrene, vinyl acetate, hydroxyethyl vinyl ether, ethylene glycol divinyl ether, pentaerythritol trivinyl ether, (meth) acrylamide, N-hydroxymethyl (meth) acrylamide, N -Vinylformamide, acrylonitrile, etc. are mentioned, These can be used individually or in mixture of 2 or more types.

As the resin, a transparent resin having a transmittance of preferably 80% or more, more preferably 95% or more in the entire wavelength region of 400 to 700 nm in the visible light region is used. The transparent resin includes a thermoplastic resin, a thermosetting resin, and a photosensitive resin, and these can be used alone or in admixture of two or more, and the photosensitive resin is particularly preferable.
As the photosensitive resin, a (meth) acrylic compound having a reactive substituent such as an isocyanate group, an aldehyde group or an epoxy group on a linear polymer having a reactive substituent such as a hydroxyl group, a carboxyl group or an amino group, A resin obtained by reacting cinnamic acid and introducing a photocrosslinkable group such as a (meth) acryloyl group or a styryl group into the linear polymer is used. In addition, a linear polymer containing an acid anhydride such as a styrene-maleic anhydride copolymer or an α-olefin-maleic anhydride copolymer is converted into a (meth) acrylic compound having a hydroxyl group such as hydroxyalkyl (meth) acrylate. Half-esterified products are also used.

Examples of the thermoplastic resin include butyral resin, styrene-maleic acid copolymer, chlorinated polyethylene, chlorinated polypropylene, polyvinyl chloride, vinyl chloride-vinyl acetate copolymer, polyvinyl acetate, polyurethane resin, and polyester resin. , Acrylic resins, alkyd resins, styrene resins, polyamide resins, rubber resins, cyclized rubber resins, celluloses, polybutadiene, polyimide resins, and the like. Examples of the thermosetting resin include an epoxy resin, a benzoguanamine resin, a rosin-modified maleic acid resin, a rosin-modified fumaric acid resin, a phenol resin, a melamine resin, and a urea resin.

The resin preferably contains an alkali-soluble non-photosensitive resin when a color filter pattern is formed by alkali development using the color filter colorant produced by the method of the present invention. The alkali-soluble non-photosensitive resin is a resin that dissolves in an alkaline aqueous solution and does not crosslink with radicals. For example, the weight-average molecular weight having an acidic functional group such as a carboxyl group or a sulfone group is 1,000 to 500,000, preferably 5,000 to 100,000. These resins are mentioned. Specific examples of the alkali-soluble non-photosensitive resin include acrylic resin, α-olefin / (anhydrous) maleic acid copolymer, styrene / (anhydrous) maleic acid copolymer, styrene / styrene sulfonic acid copolymer, An ethylene / (meth) acrylic acid copolymer, an isobutylene / (anhydrous) maleic acid copolymer, etc. are mentioned. Among them, at least one resin selected from an acrylic resin, an α-olefin / (anhydrous) maleic acid copolymer, a styrene / (anhydrous) maleic acid copolymer, and a styrene / styrene sulfonic acid copolymer, particularly an acrylic resin. Is preferably used because of its high heat resistance and transparency.

（Ｒaは、水素原子またはメチル基、Ｒbは炭素数２〜１０のアルキレン基、ＲCは水素原子または置換されていてもよい炭素数１〜２０のアルキル基を表す。ｍは１〜１５の整数を表す。） Further, as the resin, it is preferable to use a transparent resin obtained by copolymerizing the compound (a) represented by the following general formula (1) and another compound (b) having an ethylenically unsaturated double bond. .
Formula (1)

(Ra represents a hydrogen atom or a methyl group, Rb represents an alkylene group having 2 to 10 carbon atoms, RC represents a hydrogen atom or an optionally substituted alkyl group having 1 to 20 carbon atoms. M represents an integer of 1 to 15) Represents.)

In the general formula (1), the alkylene group Rb preferably has 2 to 3 carbon atoms. The alkyl group of RC has 1-20 carbon atoms, more preferably 1-10, and RC may contain a substituent such as a benzene ring. When the carbon number of the alkyl group of RC is 1 to 10, the alkyl group becomes an obstacle and suppresses the approach between the resins and promotes adsorption / orientation to the pigment. The hindrance effect becomes high and shows a tendency to prevent even the adsorption / orientation of the benzene ring to the pigment. This tendency becomes more prominent as the carbon chain length of the alkyl group of RC becomes longer. When the carbon number exceeds 20, the adsorption / orientation of the benzene ring is extremely reduced. Examples of the alkyl group containing a benzene ring represented by RC include a benzyl group and a 2-phenyl (iso) propyl group.

Compound (a) includes phenol ethylene oxide (EO) modified (meth) acrylate, paracumylphenol EO or propylene oxide (PO) modified (meth) acrylate, nonylphenol EO modified (meth) acrylate, nonylphenol PO modified (Meth) acrylate etc. are mentioned. Among these compounds, EO or PO-modified (meth) acrylate of paracumylphenol has not only the effect of the π-electron of the benzene ring, but also its steric effect, and has a better adsorption / orientation surface for the pigment. Since it can form, it is more effective.

As the compound (b), (meth) acrylic acid, methyl (meth) acrylate, ethyl (meth) acrylate, (iso) propyl (meth) acrylate, (iso) butyl (meth) acrylate, (iso) pentyl (meth) Acrylate, 2-hydroxyethyl (meth) acrylate, 2-hydroxypropyl (meth) acrylate, benzyl (meth) acrylate, cyclohexyl (meth) acrylate, glycidyl (meth) acrylate, isobornyl (meth) acrylate, acid phosphooxyethyl (meth) ) Acrylate, acid phosphooxypropyl (meth) acrylate, 3-chloro-2-acid phosphooxyethyl (meth) acrylate, acid phosphooxypolyethylene glycol mono (meth) acrylate, etc. .

The proportion of the compound (a) in the transparent resin obtained by copolymerizing the compound (a) represented by the general formula (1) and another compound (b) having an ethylenically unsaturated double bond is 0. .1 to 50% by weight, more preferably 10 to 35% by weight. When the proportion of the compound (a) is less than 0.1% by weight, the pigment dispersion effect decreases. On the other hand, when the amount is more than 50% by weight, the hydrophobicity is increased, and the developability of the color filter coloring material may be lowered or a residue may be caused.

When the colorant is cured by ultraviolet irradiation, a photopolymerization initiator or the like is added to the color filter colorant.
Examples of the photopolymerization initiator include 4-phenoxydichloroacetophenone, 4-t-butyl-dichloroacetophenone, diethoxyacetophenone, 1- (4-isopropylphenyl) -2-hydroxy-2-methylpropan-1-one, 1- Hydroxycyclohexyl phenyl ketone, 2-benzyl-2-dimethylamino-1- (4-morpholinophenyl) -butan-1-one, 2-methyl-1- [4- (methylthio) phenyl] -2-morpholinopropane Acetophenone photopolymerization initiators such as -1-one, benzoin photopolymerization initiators such as benzoin, benzoin methyl ether, benzoin ethyl ether, benzoin isopropyl ether, and benzyldimethyl ketal, benzophenone, benzoylbenzoic acid, methyl benzoylbenzoate, 4 Benzophenone photopolymerization initiators such as phenylbenzophenone, hydroxybenzophenone, acrylated benzophenone, 4-benzoyl-4'-methyldiphenyl sulfide, thioxanthone, 2-chlorothioxanthone, 2-methylthioxanthone, isopropylthioxanthone, 2 Thioxanthone photopolymerization initiators such as 2,4-diisopropylthioxanthone, 2,4,6-trichloro-s-triazine, 2-phenyl-4,6-bis (trichloromethyl) -s-triazine, 2- (p -Methoxyphenyl) -4,6-bis (trichloromethyl) -s-triazine, 2- (p-tolyl) -4,6-bis (trichloromethyl) -s-triazine, 2-piperonyl-4,6-bis (Trichloromethyl) -s-triazine, 2,4-bis (trick (Romethyl) -6-styryl-s-triazine, 2- (naphth-1-yl) -4,6-bis (trichloromethyl) -s-triazine, 2- (4-methoxy-naphth-1-yl) -4 , 6-Bis (trichloromethyl) -s-triazine, 2,4-trichloromethyl- (piperonyl) -6-triazine, 2,4-trichloromethyl (4′-methoxystyryl) -6-triazine, etc. A polymerization initiator, a borate photopolymerization initiator, a carbazole photopolymerization initiator, an imidazole photopolymerization initiator, or the like is used.

These photopolymerization initiators are used alone or in admixture of two or more. As sensitizers, α-acyloxy esters, acylphosphine oxides, methylphenylglyoxylate, benzyl, 9,10-phenance are used. Such as lenquinone, camphorquinone, ethylanthraquinone, 4,4′-diethylisophthalophenone, 3,3 ′, 4,4′-tetra (t-butylperoxycarbonyl) benzophenone, 4,4′-diethylaminobenzophenone, etc. A compound can also be used in combination.

In the method for producing a colorant for color filter of the present invention, prior to step (A), a pigment composition containing a pigment, a pigment derivative, and a liquid medium is converted into a three-roll mill, a two-roll mill, a sand mill, a kneader, an attritor, It can also be pre-dispersed using various dispersing means such as a paint conditioner. It is also preferable from the viewpoint of dispersion efficiency to disperse the pigment composition containing the pigment, the pigment derivative, and the liquid medium with a wet disperser using a medium having a particle size larger than 0.3 mmφ. At this time, if a medium having a particle diameter of 0.5 mm to 1.0 mm is used, the effect becomes remarkable. At this time, the dispersion method may be either circulation or path dispersion, but path dispersion is preferred.

When dispersing the pigment composition, a dispersion aid such as a resin-type pigment dispersant or a surfactant can be appropriately used. Since the dispersion aid is excellent in pigment dispersion and has a great effect of preventing re-aggregation of the pigment after dispersion, a color filter colorant formed by dispersing the pigment in a liquid medium using the dispersion aid was used. In this case, a color filter having excellent transparency can be obtained.
The resin-type pigment dispersant has a pigment affinity part having a property of adsorbing to the pigment and a part compatible with the pigment carrier, and adsorbs to the pigment to stabilize the dispersion of the pigment on the pigment carrier. It works. Specific examples of resin-type pigment dispersants include polycarboxylic acid esters such as polyurethane and polyacrylate, unsaturated polyamides, polycarboxylic acids, polycarboxylic acid (partial) amine salts, polycarboxylic acid ammonium salts, and polycarboxylic acid alkylamines. Salts, polysiloxanes, long-chain polyaminoamide phosphates, hydroxyl group-containing polycarboxylic acid esters, their modified products, amides formed by the reaction of poly (lower alkyleneimines) with polyesters having free carboxyl groups, and the like Salt or the like is used. In addition, water-soluble resins such as (meth) acrylic acid-styrene copolymer, (meth) acrylic acid- (meth) acrylic acid ester copolymer, styrene-maleic acid copolymer, polyvinyl alcohol, and polyvinylpyrrolidone, and water-soluble Polymer compounds, polyesters, modified polyacrylates, ethylene oxide / propylene oxide adducts, and the like are used. These can be used alone or in admixture of two or more.

Specifically, Disperbyk or Disperbyk-101, 103, 107, 108, 110, 111, 116, 130, 140, 154, 161, 162, 163, 164, 165, 166, 170, 171, 174 manufactured by Big Chemie 180, 181, 182, 183, 184, 185, 190, 2000, 2001 or Anti-Terra-U, 203, 204 or BYK-P104, P104S, 220S or Lactimon, Lactimon-WS or Bykumen, etc., manufactured by Abyssia SOLSPERSE-3000, 9000, 13240, 13650, 13940, 17000, 18000, 20000, 21000, 24000, 26000, 27000, 28000, 31845, 32000, 32500, 32600, 34750, 36600, 38500, 41000, 4109 EF95, etc., EFKA-46, 47, 48, 452, LP4008, 4009, LP4010, LP4050, LP4055, 400, 401, 402, 403, 450, 451, 453, 4540, 4550, LP4560, manufactured by Fuka Chemicals 120, 150, 1501, 1502, 1503 and the like.

Examples of the surfactant include sodium lauryl sulfate, polyoxyethylene alkyl ether sulfate, sodium dodecylbenzene sulfonate, alkali salt of styrene-acrylic acid copolymer, sodium stearate, sodium alkyl naphthalene sulfonate, alkyl diphenyl ether disulfonic acid. Anionic surfactants such as sodium, monoethanolamine lauryl sulfate, triethanolamine lauryl sulfate, ammonium lauryl sulfate, monoethanolamine stearate, sodium stearate, sodium lauryl sulfate, monoethanolamine of styrene-acrylic acid copolymer; Polyoxyethylene oleyl ether, polyoxyethylene lauryl ether, polyoxyethylene nonylphenyl ether, polyoxyethylene sol Nonionic surfactants such as tan monostearate and polyethylene glycol monolaurate; Chaotic surfactants such as alkyl quaternary ammonium salts and their ethylene oxide adducts; Alkyl betaines such as alkyldimethylaminoacetic acid betaines; Alkyl imidazolines These amphoteric surfactants can be used, and these can be used alone or in admixture of two or more.

In addition, the color filter colorant may contain a storage stabilizer in order to stabilize the colorant viscosity with time. Examples of storage stabilizers include quaternary ammonium chlorides such as benzyltrimethyl chloride and diethylhydroxyamine, organic acids such as lactic acid and oxalic acid, and organic acids such as methyl ether, t-butylpyrocatechol, tetraethylphosphine, and tetraphenylphosphine. Examples thereof include phosphine and phosphite.
The pigment is preferably contained in the color filter colorant at a ratio of 1.5 to 7% by weight. In addition, the pigment is preferably contained in the final filter segment in a proportion of 10 to 40% by weight, more preferably 20 to 40% by weight, and the remainder is substantially from the resinous binder provided by the monomer and / or resin. Become.

The color filter colorant can be adjusted in the form of a solvent development type or alkali development type color resist material. The colored resist material includes a thermoplastic resin or a thermosetting resin and a monomer, or a photosensitive resin, a pigment, a pigment derivative, a photopolymerization initiator, and a liquid medium.
The color filter coloring material may be coarse particles of 5 μm or more, preferably coarse particles of 1 μm or more, more preferably coarse particles of 0.5 μm or more and mixed dust by means of centrifugal separation, sintering filter, membrane filter or the like. Is preferably removed.

Next, the color filter of the present invention will be described.
The color filter of this invention comprises the filter segment formed using the coloring material for color filters manufactured by the manufacturing method of this invention. Examples of the color filter include those having a red filter segment, a green filter segment, and a blue filter segment, or those having a magenta filter segment, a cyan filter segment, and a yellow filter segment.
The color filter of this invention can be manufactured by forming the filter segment of each color on a transparent substrate using the coloring material for color filters by the photolithographic method.

As the transparent substrate, a glass plate or a resin plate such as polycarbonate, polymethyl methacrylate, or polyethylene terephthalate is used.
Each color filter segment is formed by the photolithography method by the following method. That is, the coloring material prepared as the solvent developing type or alkali developing type coloring resist material is applied on a transparent substrate by a coating method such as spray coating, spin coating, slit coating, roll coating, etc. Apply to 5 μm. If necessary, the dried film is exposed to ultraviolet light through a mask having a predetermined pattern provided in contact with or non-contact with the film. Then, after immersing in a solvent or an alkaline developer, or spraying the developer with a spray or the like to remove the uncured portion to form a desired pattern, the same operation is repeated for other colors to produce a color filter. be able to. Furthermore, in order to accelerate the polymerization of the colored resist material, heating can be performed as necessary. According to the photolithography method, a color filter with higher accuracy than the printing method can be manufactured.

In development, an aqueous solution such as sodium carbonate or sodium hydroxide is used as an alkali developer, and an organic alkali such as dimethylbenzylamine or triethanolamine can also be used. Moreover, an antifoamer and surfactant can also be added to a developing solution.
In order to increase the UV exposure sensitivity, after coating and drying the colored resist material, a water-soluble or alkali-soluble resin such as polyvinyl alcohol or a water-soluble acrylic resin is applied and dried to form a film that prevents polymerization inhibition by oxygen. Thereafter, ultraviolet exposure can also be performed.
The color filter of the present invention can be produced by an electrodeposition method, a transfer method or the like in addition to the above method, and the colorant produced by the production method of the present invention can be used in any method. The electrodeposition method is a method for producing a color filter by using a transparent conductive film formed on a transparent substrate and forming each color filter segment on the transparent conductive film by electrophoresis of colloidal particles. is there.

The transfer method is a method in which a color filter layer is formed in advance on the surface of a peelable transfer base sheet, and this color filter layer is transferred to a desired transparent substrate.
If the black matrix is formed in advance before forming the filter segment on the transparent substrate or the reflective substrate, the contrast ratio of the liquid crystal display panel can be further increased. As the black matrix, a chromium, chromium / chromium oxide multilayer film, an inorganic film such as titanium nitride, or a resin film in which a light-shielding agent is dispersed is used, but is not limited thereto. In addition, a thin film transistor (TFT) may be formed in advance on the transparent substrate or the reflective substrate, and then a filter segment may be formed. By forming the filter segment on the TFT substrate, the aperture ratio of the liquid crystal display panel can be increased and the luminance can be improved.

On the color filter of the present invention, an overcoat film, a columnar spacer, a transparent conductive film, a liquid crystal alignment film, and the like are formed as necessary.
The color filter is bonded to the counter substrate using a sealant, and after injecting liquid crystal from the injection port provided in the seal part, the injection port is sealed, and if necessary, a polarizing film or a retardation film is placed outside the substrate. A liquid crystal display panel is manufactured by bonding.
Such liquid crystal display panels include twisted nematic (TN), super twisted nematic (STN), in-plane switching (IPS), vertical alignment (VA), and optically convented bend (OCB). It can be used for a liquid crystal display mode in which colorization is performed using a color filter.

Hereinafter, the present invention will be described based on examples, but the present invention is not limited thereto. In the examples and comparative examples, “parts” means “parts by weight”.
Prior to the examples, a method for measuring the contrast ratio of the resist-coated substrate will be described.
A resist material coated substrate is sandwiched between two polarizing plates, and light is irradiated from one polarizing plate side using a backlight unit for liquid crystal display. The light emitted from the backlight unit passes through the first polarizing plate and is polarized, and then passes through the resist material-coated substrate and reaches the second polarizing plate. If the polarization planes of the first polarizing plate and the second polarizing plate are parallel, light passes through the second polarizing plate, but if the polarization plane is perpendicular, the light passes through the second polarizing plate. Are blocked by the polarizing plate. However, when the light polarized by the first polarizing plate passes through the resist material coated substrate, scattering due to pigment particles occurs and a part of the polarization plane shifts. When the amount of light transmitted through the second polarizing plate is reduced and the deflecting plate is perpendicular, a part of the light is transmitted through the second polarizing plate. This transmitted light is measured as the luminance on the polarizing plate, and the ratio between the luminance when the polarizing plate is parallel and the luminance when the polarizing plate is orthogonal is defined as the contrast ratio.
Contrast ratio = (Luminance when parallel) / (Luminance when direct)

Accordingly, when scattering occurs due to the pigment in the resist material coating film, the luminance when parallel is lowered and the luminance when perpendicular is increased, and the contrast ratio is lowered.
The luminance meter was a color luminance meter BM-5A manufactured by Topcon Corporation, and the polarizing plate was a polarizing film LLC2-92-18 manufactured by Sanritsu. In the measurement, in order to block unnecessary light, measurement was performed by applying a black mask having a 1 cm square hole in the measurement portion.
First, adjustment of the acrylic resin solutions 1 to 4 used in Examples and Comparative Examples will be described. The molecular weight of the resin is a weight average molecular weight in terms of polystyrene measured by GPC (gel permeation chromatography).

(Preparation of acrylic resin solution 1)
370 parts of cyclohexanone was placed in a reaction vessel, heated to 80 ° C. while injecting nitrogen gas into the vessel, and a mixture of the following monomer and thermal polymerization initiator was added dropwise at the same temperature over 1 hour to carry out a polymerization reaction.
Methacrylic acid 20.0 parts Methyl methacrylate 10.0 parts n-Butyl methacrylate 55.0 parts 2-Hydroxyethyl methacrylate 15.0 parts 2,2′-azobisisobutyronitrile 4.0 parts After the reaction at 3 ° C. for 3 hours, 1.0 part of azobisisobutyronitrile dissolved in 50 parts of cyclohexanone was added, and the reaction was further continued at 80 ° C. for 1 hour to obtain an acrylic resin solution. . The weight average molecular weight of the acrylic resin was about 40,000.
After cooling to room temperature, about 2 g of the resin solution was sampled, heated and dried at 180 ° C. for 20 minutes to measure the nonvolatile content, and cyclohexanone was added to the previously synthesized resin solution so that the nonvolatile content was 20% by weight. To prepare an acrylic resin solution.

(Preparation of acrylic resin solution 2)
370 parts of cyclohexanone was placed in a reaction vessel, heated to 80 ° C. while injecting nitrogen gas into the vessel, and a mixture of the following monomer and thermal polymerization initiator was added dropwise at the same temperature over 1 hour to carry out a polymerization reaction.
Methacrylic acid 20.0 parts Methyl methacrylate 10.0 parts n-Butyl methacrylate 35.0 parts 2-Hydroxyethyl methacrylate 15.0 parts 2,2'-azobisisobutyronitrile 4.0 parts paracumylphenol ethylene oxide modification Acrylate 20.0 parts ("Aronix M110" manufactured by Toa Gosei Co., Ltd.)
After completion of the dropwise addition, the mixture was further reacted at 80 ° C. for 3 hours, and then 1.0 part of azobisisobutyronitrile dissolved in 50 parts of cyclohexanone was added, and the reaction was further continued at 80 ° C. for 1 hour. A resin solution was obtained. The weight average molecular weight of the acrylic resin was about 40,000.
After cooling to room temperature, about 2 g of the resin solution was sampled, heated and dried at 180 ° C. for 20 minutes to measure the nonvolatile content, and cyclohexanone was added to the previously synthesized resin solution so that the nonvolatile content was 20% by weight. To prepare an acrylic resin solution.

(Preparation of acrylic resin solution 3)
560 parts of cyclohexanone was placed in a reaction vessel, heated to 80 ° C. while injecting nitrogen gas into the vessel, and a mixture of the following monomer and thermal polymerization initiator was added dropwise at the same temperature over 1 hour to carry out a polymerization reaction.
Methacrylic acid 34.0 parts Methyl methacrylate 23.0 parts n-Butyl methacrylate 45.0 parts 2-Hydroxyethyl methacrylate 70.5 parts 2,2'-azobisisobutyronitrile 8.0 parts After completion of dropping, 100 more After reacting at 0 ° C. for 3 hours, 1.0 part of azobisisobutyronitrile dissolved in 55 parts of cyclohexanone was added, and the reaction was further continued at 80 ° C. for 1 hour to obtain a copolymer solution. .
Next, with respect to 338 parts of the obtained copolymer solution, the mixture of the following compound was dripped at 70 degreeC over 3 hours.
2-Methacryloyl ethyl isocyanate 32.0 parts Dibutyltin laurate 0.4 parts Cyclohexanone 120.0 parts After cooling to room temperature, about 2 g of the resin solution was sampled and heated and dried at 180 ° C for 20 minutes to measure the nonvolatile content. Then, cyclohexanone was added to the previously synthesized resin solution so that the nonvolatile content was 20% by weight to prepare a photosensitive resin solution. The obtained photosensitive resin had a weight average molecular weight of 20,000 and a double bond equivalent of 470.

(Preparation of acrylic resin solution 4)
560 parts of cyclohexanone was placed in a reaction vessel, heated to 80 ° C. while injecting nitrogen gas into the vessel, and a mixture of the following monomer and thermal polymerization initiator was added dropwise at the same temperature over 1 hour to carry out a polymerization reaction.
Methacrylic acid 34.0 parts Methyl methacrylate 23.0 parts n-Butyl methacrylate 25.0 parts 2-Hydroxyethyl methacrylate 70.5 parts 2,2'-azobisisobutyronitrile 8.0 parts paracumylphenol ethylene oxide modification Acrylate 20.0 parts ("Aronix M110" manufactured by Toa Gosei Co., Ltd.)
After completion of the dropwise addition, the mixture was further reacted at 100 ° C. for 3 hours, then 1.0 part of azobisisobutyronitrile dissolved in 55 parts of cyclohexanone was added, and the reaction was further continued at 80 ° C. for 1 hour. A polymer solution was obtained.
Next, with respect to 338 parts of the obtained copolymer solution, the mixture of the following compound was dripped at 70 degreeC over 3 hours.
2-Methacryloyl ethyl isocyanate 32.0 parts Dibutyltin laurate 0.4 parts Cyclohexanone 120.0 parts After cooling to room temperature, about 2 g of the resin solution was sampled and heated and dried at 180 ° C for 20 minutes to measure the nonvolatile content. Then, cyclohexanone was added to the previously synthesized resin solution so that the nonvolatile content was 20% by weight to prepare a photosensitive resin solution. The obtained photosensitive resin had a weight average molecular weight of 20,000 and a double bond equivalent of 470.

[Comparative Example 1]
After the pigment composition having the following composition is stirred and mixed uniformly, 0.3 mmφ zirconia beads are used, the media separation mechanism is a slit type, and a dyno mill having a disk as a stirring blade (manufactured by Shinmaru Enterprises Co., Ltd.) ) For 2 hours and filtered through a 5 μm filter to prepare a copper phthalocyanine dispersion.
ε-type copper phthalocyanine pigment (CI Pigment Blue 15: 6) 10.0 parts (“Heliogen Blue L-6700F” manufactured by BASF)
Phthalocyanine pigment derivative (Compound 1) 1.0 part Phosphate ester pigment dispersant 1.0 part ("BYK111" manufactured by BYK Chemie)
Acrylic resin solution 1 40.0 parts Cyclohexanone 48.0 parts Next, a mixture having the following composition was stirred and mixed to be uniform, and then filtered through a 1 μm filter to obtain a blue resist material.
Copper phthalocyanine dispersion 45.0 parts Acrylic resin solution 1 15.0 parts Trimethylolpropane triacrylate 5.6 parts ("NK ester ATMPT" manufactured by Shin-Nakamura Chemical Co., Ltd.)
Photopolymerization initiator (“Irgacure 907” manufactured by Ciba Geigy) 2.0 parts sensitizer (“EAB-F” manufactured by Hodogaya Chemical Co., Ltd.) 0.2 parts Cyclohexanone 32.2 parts

[Example 1]
In Comparative Example 1, the pigment composition was 0.3 mmφ zirconia beads, the media separation mechanism was a centrifugal separation type, and the ultra apex mill (manufactured by Kotobuki Giken Kogyo Co., Ltd.) with a rotor pin as a stirring blade was used. A blue resist material was obtained in the same manner as in Comparative Example 1 except that the dispersion was performed for time.
[Example 2]
A blue resist material was obtained in the same manner as in Example 1 except that 0.3 mmφ zirconia beads were replaced with 0.1 mmφ zirconia beads in Example 1.

[Comparative Example 2]
A blue resist material was obtained in the same manner as in Comparative Example 1 except that the phthalocyanine pigment derivative was omitted.
[Comparative Example 3]
A blue resist material was obtained in the same manner as in Example 3 except that the phthalocyanine pigment derivative was omitted.
[Comparative Example 4]
A blue resist material was obtained in the same manner as in Example 4 except that the phthalocyanine pigment derivative was omitted.

[Comparative Example 5]
After uniformly stirring and mixing the pigment composition having the following composition, 0.3 mmφ zirconia beads were used for dispersion for 2 hours with the same dyno mill as in Comparative Example 1, and then filtered through a 5 μm filter to obtain a copper phthalocyanine dispersion. Produced.
ε-type copper phthalocyanine pigment (CI Pigment Blue 15: 6) 10.0 parts (“Heliogen Blue L-6700F” manufactured by BASF)
Phthalocyanine pigment derivative (Compound 1) 1.0 part Phosphate ester pigment dispersant 1.0 part ("BYK111" manufactured by BYK Chemie)
Acrylic resin solution 2 40.0 parts Cyclohexanone 48.0 parts Next, a mixture having the following composition was stirred and mixed to be uniform, and then filtered through a 1 μm filter to obtain a blue resist material.
Copper phthalocyanine dispersion 45.0 parts Acrylic resin solution 3 15.0 parts Trimethylolpropane triacrylate 5.6 parts ("NK ester ATMPT" manufactured by Shin-Nakamura Chemical Co., Ltd.)
Photopolymerization initiator (“Irgacure 907” manufactured by Ciba Geigy) 2.0 parts sensitizer (“EAB-F” manufactured by Hodogaya Chemical Co., Ltd.) 0.2 parts Cyclohexanone 32.2 parts

[Example 3]
In Comparative Example 5, a blue resist material was obtained in the same manner as in Comparative Example 5, except that 0.3 mmφ zirconia beads were used and the pigment composition was dispersed for 2 hours in the same Ultra Apex mill as in Example 1. .
[Example 4]
In Example 3, a blue resist material was obtained in the same manner as in Example 3 except that the 0.3 mmφ zirconia beads were replaced with 0.1 mmφ zirconia beads.
[Comparative Example 6]
In Comparative Example 5, a blue resist material was obtained in the same manner as in Comparative Example 5, except that 0.3 mmφ zirconia beads were replaced with 0.5 mmφ zirconia beads.
[Comparative Example 7]
In Example 3, a blue resist material was obtained in the same manner as in Example 3 except that 0.3 mmφ zirconia beads were replaced with 0.5 mmφ zirconia beads.

[Comparative Example 8]
After uniformly stirring and mixing the pigment composition having the following composition, 0.3 mmφ zirconia beads were used for dispersion for 2 hours with the same dyno mill as in Comparative Example 1, and then filtered through a 5 μm filter to obtain a copper phthalocyanine dispersion. Produced.
ε-type copper phthalocyanine pigment (CI Pigment Blue 15: 6) 10.0 parts (“Heliogen Blue L-6700F” manufactured by BASF)
Phthalocyanine pigment derivative (Compound 1) 1.0 part Phosphate ester pigment dispersant 1.0 part ("BYK111" manufactured by BYK Chemie)
Acrylic resin solution 2 40.0 parts Cyclohexanone 48.0 parts Next, a mixture having the following composition was stirred and mixed to be uniform, and then filtered through a 1 μm filter to obtain a blue resist material.
Copper phthalocyanine dispersion 45.0 parts Acrylic resin solution 4 15.0 parts Trimethylolpropane triacrylate 5.6 parts (“NK ester ATMPT” manufactured by Shin-Nakamura Chemical Co., Ltd.)
Photopolymerization initiator (“Irgacure 907” manufactured by Ciba Geigy) 2.0 parts sensitizer (“EAB-F” manufactured by Hodogaya Chemical Co., Ltd.) 0.2 parts Cyclohexanone 32.2 parts

[Example 5] In the same manner as in Comparative Example 8, except that the pigment composition was dispersed for 2 hours in the same Ultra Apex mill as in Example 1 using 0.03 mmφ zirconia beads. A blue resist material was obtained.
[Comparative Example 9]
A blue resist material was obtained in the same manner as in Comparative Example 8 except that the phthalocyanine pigment derivative 1 was omitted.

[Comparative Example 10]
A blue resist material was obtained in the same manner as in Example 5 except that 0.03 mmφ zirconia beads were replaced with 0.5 mmφ zirconia beads in Example 5.

The color filter colorant obtained in Examples 1 to 5 and Comparative Examples 1 to 10 is formed on a glass substrate having a thickness of 100 mm × 100 mm and a thickness of 1.1 mm using a spin coater at 500 rpm, 1000 rpm, and 1500 rpm. The three coated substrates having different film thicknesses were obtained by coating. The resist-coated substrate was dried at 70 ° C. for 20 minutes, exposed to ultraviolet light with an integrated light amount of 150 mJ using an ultrahigh pressure mercury lamp, heated at 230 ° C. for 1 hour, allowed to cool, and then measured for the contrast ratio. Next, the chromaticity (Y, x, y) of the coating film with a C light source was measured using a microspectrophotometer (“OSP-SP100” manufactured by Olympus Optical Co., Ltd.). From the three sets of contrast ratio and chromaticity measurement results, the contrast ratio and brightness at y = 0.140 of the resist material coated substrate were determined using an approximation method.
Subsequently, the ELD type E-type viscometer (with the viscosity of the color filter coloring materials obtained in Examples 1 to 5 and Comparative Examples 1 to 10 immediately after adjustment and aged for one week in an oven at 40 ° C. ( Measured at 25 ° C. using Toki Sangyo Co., Ltd. The above results are shown in Tables 1 and 2.

The color filter coloring materials obtained in Examples 1 to 5 had a low viscosity and a high fluidity as compared with those obtained in Comparative Examples, and were excellent in stability over time. Moreover, the required characteristics such as high contrast ratio and high brightness required for the color filter were satisfied.
Further, as the pigment and pigment derivative in this example, copper phthalocyanine pigment (CI Pigment Blue 15: 6) and compound 9, copper phthalocyanine pigment (CI Pigment Green 36) and isoindoline pigment ( CI Pigment Yellow 185) and Compound 2, Dioxazine Violet Pigment (CI Pigment Violet 23) and Compound 4, Diketopyrrolopyrrole Pigment (CI Pigment Red 254), Anthraquinone Pigment (C I. Pigment Red 177), anthraquinone pigments (CI Pigment Yellow 199) and Compound 3 were used, and similar results were obtained.

Claims (10)

Wet disperser using media with a particle size of 0.3 mmφ or less, without slit-type and screen-type media separation mechanisms, but only with centrifugal-type media separation mechanisms, pigments, pigment derivatives, and liquids The manufacturing method of the coloring material for color filters characterized by including the process (A) which supplies and disperse | distributes the pigment composition containing a medium. The method for producing a color filter coloring material according to claim 1, wherein the wet disperser includes a rotor pin. The method for producing a colorant for a color filter according to claim 1 or 2, wherein the media has a particle size of 0.1 mmφ or less. The method for producing a color filter colorant according to any one of claims 1 to 3, wherein in the step (A), the pigment composition further contains a resin. The coloring for color filter according to any one of claims 1 to 4, further comprising a step (B) of adding and mixing a monomer and / or a resin to the dispersion of the pigment composition obtained in the step (A). A method of manufacturing the material. 6. The method for producing a color filter colorant according to claim 4, wherein the resin is a photosensitive resin. The resin is a transparent resin obtained by copolymerizing a compound (a) represented by the following general formula (1) and a compound (b) having another ethylenically unsaturated double bond. The manufacturing method of the coloring material for color filters in any one of 4 thru | or 6.
Formula (1)

(R _a represents a hydrogen atom or a methyl group, R _b represents an alkylene group having 2 to 10 carbon atoms, R _C represents a hydrogen atom or an optionally substituted alkyl group having 1 to 20 carbon atoms. Represents an integer of 15.) 8. The method for producing a colorant for a color filter according to claim 4, wherein the resin is an alkali-soluble non-photosensitive resin. A color filter colorant produced by the production method according to claim 1. A color filter comprising a filter segment formed using the color filter colorant according to claim 9.