JP4969491B2 - Colored curable composition, colored pattern, color filter, method for producing color filter, and liquid crystal display element - Google Patents

Description

  The present invention relates to a colored curable composition, a colored pattern, a color filter, a method for producing a color filter, and a liquid crystal display element.

  A color filter constituting a liquid crystal display (LCD), a color image pickup tube element (CCD), etc. is a solvent dispersion composition of a colorant such as an organic pigment and an inorganic pigment, a binder resin and / or a monomer, and a photopolymerization initiator. And a colored photosensitive composition containing other components, which are manufactured by a photolithographic method including a step of coating and drying on a transparent substrate to form a coating film having a thickness of about 1 μm to 3 μm. .

Examples of the coating method on the substrate include a spin coating method and a die coating method, which are appropriately used depending on the characteristics.
The spin coating method is widely used for forming a thin film on a relatively small-sized substrate. While rotating the transparent substrate at a constant rotational speed, the coating solution is dropped onto the central portion of the transparent substrate and centrifugal force is applied. Is a coating method in which a coating film having a desired film thickness is formed on the surface of the transparent substrate by extending the coating solution thinly and controlling the number of revolutions and the rotation time of the transparent substrate suitable for the coating solution. However, due to the principle of extending the coating film thinly by utilizing the centrifugal force due to rotation, there is a drawback that the coating film thickness at the rotation center portion and the peripheral portion of the transparent substrate becomes too thick compared to the intermediate portion.

  The die coating method is a method suitable for forming a thin film on a large-sized substrate, and a coating liquid having a desired film thickness is formed on the surface of a transparent substrate while discharging the coating liquid from the slit and moving the slit. Application method. However, due to the mechanism, stripe-like unevenness (straight unevenness) is likely to occur in a direction perpendicular to the direction of movement of the slit, and the outer peripheral portion of the coating film rises and the film thickness becomes thicker than the central portion of the substrate.

  Further, there is a problem that pinholes (white spots) occur if the drying property and surface tension of the coating solution are not appropriate regardless of the coating method.

Various attempts have been made so far to solve the problem of non-uniformity of the coating film in the spin coating method and the die coating method. For example, Patent Document 1 discloses a technique for solving the problem by adjusting the contact angle of the composition, and a fluorine-based surfactant is suitably used. Patent Document 2 discloses a technique for solving the problem by using a composition having polysiloxane as an antistatic agent.
JP 2007-10992 A JP 2007-161886 A

This invention is made | formed in view of said background art, and makes it a subject to achieve the objective shown below.
An object of the present invention is to provide a colored curable composition that can suppress planar deterioration due to coating and can form a colored film with few defects.
Another object of the present invention is to use the above-mentioned colored curable composition, having a good surface shape and less defects, a color filter having this color pattern, a method for producing the color filter, And providing a liquid crystal display device including the color filter.

Means for solving the above-mentioned problems are as follows.
That is, the colored curable composition of the present invention comprises (A) a colorant, (B) a photopolymerizable compound, (C) a photopolymerization initiator, and (D) a repeating unit represented by the following general formula (1). It contains the copolymer containing this, It is characterized by the above-mentioned.

In the general formula (1), R ¹ represents a hydrogen atom or a methyl group, X ¹ represents an oxygen atom, a sulfur atom, or —N (R) —, and m1 represents an integer of 0 to 18. , N1 represents an integer of 1-18. Here, R represents a hydrogen atom or an alkyl group having 1 to 8 carbon atoms which may have a substituent.

  In the present invention, the copolymer having a repeating unit represented by the general formula (1) is preferably a copolymer having a repeating unit represented by the following general formula (2).

In the general formula (2), i and j each represent an integer of 1 or more, meaning that i and j types of each repeating unit are included, respectively. a and b are mass percentages representing a polymerization ratio, Σai represents a numerical value of 1% by mass to 98% by mass, and Σbj represents a numerical value of 1% by mass to 98% by mass. R ¹ , R ² , and R ³ each represent a hydrogen atom or a methyl group, X ¹ and X ² each represent an oxygen atom, a sulfur atom, or —N (R) —, and m 1 is 0. Represents an integer of -18, n1 and m2 each represent an integer of 1 to 18, and p and q each represent an integer of 1 to 20. Here, R represents a hydrogen atom or an alkyl group having 1 to 8 carbon atoms which may have a substituent.

  In the colored curable composition of the present invention, the copolymer containing the repeating unit represented by the general formula (1) is contained in an amount of 0.01% by mass to 20% by mass with respect to the total solid content in the composition. Is a preferred embodiment.

The colored pattern of the present invention is formed by the colored curable composition of the present invention.
The color filter of the present invention is characterized by having the colored pattern of the present invention on a substrate.
The method for producing a color filter of the present invention includes a step of applying the colored curable composition of the present invention by a spin coating method, a slit-and-spin method, or a die coating method, and forming a colored pattern on a substrate. It is characterized by.
The liquid crystal display element of the present invention uses the color filter of the present invention.

ADVANTAGE OF THE INVENTION According to this invention, the colored curable composition which can suppress the planar deterioration resulting from application | coating and can form a colored film with few defects can be provided.
In addition, according to the present invention, a colored pattern having a good surface shape and few defects, using the colored curable composition, a color filter having the colored pattern, a method for producing the color filter, and this A liquid crystal display element including a color filter can be provided.

Hereinafter, the present invention will be described in detail.
In the present specification, “to” is used to mean that the numerical values described before and after it are included as a lower limit value and an upper limit value.

<Colored curable composition>
The colored curable composition of the present invention comprises (A) a colorant, (B) a photopolymerizable compound, (C) a photopolymerization initiator, and (D) a repeating unit represented by the general formula (1). It is characterized by containing a polymer.
When the colored curable composition of the present invention contains the components (A) to (D), the surface tension of the colored curable composition is reduced, and the wettability with respect to the coated surface such as a substrate is improved. In addition, the white spot defect is eliminated, and furthermore, the extremely high surface uneven distribution effect of the component (D) makes it possible to make the drying in the coating process uniform, and it is possible to greatly reduce the unevenness caused by the uneven drying.
Hereinafter, each component of (A)-(D) is demonstrated in detail.

[(D) Copolymer containing repeating unit represented by formula (1)]
(Repeating unit represented by general formula (1))
The colored curable composition of the present invention contains (D) a copolymer containing a repeating unit represented by the following general formula (1). Hereinafter, this copolymer is appropriately referred to as “fluoroaliphatic group-containing polymer”.

In the general formula (1), R ¹ represents a hydrogen atom or a methyl group, X ¹ represents an oxygen atom, a sulfur atom, or —N (R) —, and m1 represents an integer of 0 to 18. , N1 represents an integer of 1-18. Here, R represents a hydrogen atom or an alkyl group having 1 to 8 carbon atoms which may have a substituent.

X ¹ is preferably an oxygen atom or —N (R) —, and more preferably an oxygen atom. Here, R represents a hydrogen atom or an optionally substituted alkyl group having 1 to 8 carbon atoms, more preferably a hydrogen atom or an alkyl group having 1 to 4 carbon atoms, a hydrogen atom or methyl Groups are more preferred.
m1 is preferably an integer of 1 to 18, more preferably an integer of 1 to 10, and still more preferably an integer of 1 to 3.
n1 is preferably 1 to 10, and more preferably 3 to 8.

  Although the specific example (a-1 to a-85) of the repeating unit represented by General formula (1) below is given, this invention is not limited to these.

The fluoroaliphatic group-containing polymer in the present invention preferably contains 1% by mass or more of the repeating unit represented by the general formula (1), more preferably 40% by mass or more, more preferably 80% by mass. It is more preferable to include the above.
Moreover, this fluoro aliphatic group containing polymer may contain 2 or more types of the repeating unit represented by the said General formula (1).

(Other repeat units)
The fluoroaliphatic group-containing polymer in the present invention may contain other repeating units in addition to the repeating unit represented by the general formula (1).
Although it does not restrict | limit especially as another repeating unit, It is also preferable that the side chain contains the alkyleneoxy group, and it is especially preferable that the polyalkyleneoxy group containing the repetition of an alkyleneoxy group is included.

  The fluoroaliphatic group-containing polymer in the present invention is preferably a copolymer containing repeating units (repeating units A and B) represented by the following general formula (2).

In the general formula (2), i and j each represent an integer of 1 or more, meaning that i and j types of each repeating unit are included, respectively. a and b are mass percentages representing a polymerization ratio, Σai represents a numerical value of 1% by mass to 98% by mass, and Σbj represents a numerical value of 1% by mass to 98% by mass. R ¹ , R ² , and R ³ each represent a hydrogen atom or a methyl group, X ¹ and X ² each represent an oxygen atom, a sulfur atom, or —N (R) —, and m 1 is 0. Represents an integer of -18, n1 and m2 each represent an integer of 1-18, and p and q each represent an integer of 1-20. Here, R represents a hydrogen atom or an alkyl group having 1 to 8 carbon atoms which may have a substituent.

Here, R ¹ , X ¹ , m 1, and n ¹ in the general formula (2) are respectively synonymous with R ¹ , X ¹ , m 1, and n ¹ in the general formula (1), and preferred embodiments are also the same. It is.

X ¹ and X ² in the general formula (2) are preferably both oxygen atoms, that is, the repeating units A and B are preferably repeating units derived from a (meth) acrylic monomer. .
As n1 and m1 in General formula (2), it is synonymous with n1 and m1 in General formula (1), and its preferable aspect is also the same.

In the general formula (2), p is preferably 2 or 3, and q is preferably 4 or 6. That is, in General formula (2), it is preferable to contain an ethyleneoxy group or a propyleneoxy group from the point of the wettability with respect to to-be-coated surfaces, such as a board | substrate.
Furthermore, as m2, 1-10 are preferable and 2-6 are more preferable from the point of the wettability with respect to to-be-coated surfaces, such as a board | substrate.

  Specific examples (b-1 to b-9) of the repeating unit B in the general formula (2) are shown below, but the present invention is not limited thereto.

  In the general formula (2), a and b are mass percentages representing the polymerization ratio of the monomer for deriving each repeating unit, Σai represents a numerical value of 1% by mass to 98% by mass, and Σbj represents 1% by mass to 98%. The numerical value of mass% is represented. Σai is 40% by mass to 98% by mass, Σbj is preferably 1% by mass to 60% by mass, Σai is 80% by mass to 98% by mass, and Σbj is 1% by mass to 30% by mass. It is preferable.

  The copolymer containing the repeating unit represented by the general formula (2) may contain a repeating unit other than the repeating units A and B, that is, Σai + Σbj <100% by mass. It is preferable that no repeating unit other than the repeating units A and B is included, that is, Σai + Σbj = 100% by mass.

Further, it is preferable that the ratio of the repeating units A and B derived from the fluoroaliphatic group-containing monomer contained in the fluoroaliphatic group-containing polymer is in a predetermined range because the surface shape can be improved. Specifically, the total mass Σai of i-type repeating units A and the total mass (Σai + Σbj) of j-type repeating units B are preferably 20% by mass to 50% by mass, It is more preferable that it is 45 mass%, and it is still more preferable that it is 25 mass%-40 mass%. When (Σai + Σbj) is in the above range, the surface state of the coating film can be further improved.
From the same viewpoint, the ratio of Σai to Σai + Σbj (Σai / (Σai + Σbj)) is preferably 0.2 to 0.8, more preferably 0.3 to 0.6, More preferably, it is 35-0.55. It is preferable that Σai / (Σai + Σbj)) is in the above range because the surface shape of the coating film can be further improved.

Specific examples of the fluoroaliphatic group-containing polymer in the present invention are shown in Table 1 below, but the present invention is not limited to the following specific examples.
In Table 1, those described in the repeating unit A are those listed in the specific examples (a-1 to a-85) of the repeating unit represented by the general formula (1). What is described in the unit B is the one given in the specific examples (b-1 to b-9) of the repeating unit B in the above general formula (2).

The monomer for obtaining the repeating unit represented by the general formula (1) can be produced by a telomerization method (also referred to as a telomer method) or an oligomerization method (also referred to as an oligomer method). Regarding the production method of these fluoroaliphatic compounds, for example, “Synthesis and Function of Fluorine Compounds” (Supervision: Nobuo Ishikawa, Issue: CMC Co., 1987), “Chemistry of Organic Fluorines Compounds”. II "(Monograph 187, Ed by Milos Hudricky and Attila E. Pavlath, American Chemical Society 1995).
The telomerization method is a method of synthesizing a telomer by radical polymerization of a fluorine-containing vinyl compound such as tetrafluoroethylene using an alkyl halide having a large chain transfer constant such as iodide as a telogen (example in Scheme-1). showed that).

  The obtained terminal iodinated telomer is usually subjected to an appropriate terminal chemical modification such as the following Scheme-2 and led to a fluoroaliphatic compound.

  Further, the production method of the fluoroaliphatic group-containing polymer in the present invention is not particularly limited. For example, cationic polymerization or radical using a vinyl group is performed using the fluoroaliphatic compound (monomer) obtained by the above-described method. It can be produced by a polymerization method such as polymerization or anionic polymerization, and among these, a radical polymerization method is particularly preferred because it can be used for general purposes.

When the radical polymerization method is used in producing the fluoroaliphatic group-containing polymer in the present invention, a polymerization initiator as shown below is used.
As the polymerization initiator, known compounds such as a radical thermal polymerization initiator and a radical photopolymerization initiator can be used, and it is particularly preferable to use a radical thermal polymerization initiator.
Here, the radical thermal polymerization initiator is a compound that generates radicals by heating to a decomposition temperature or higher. Examples of such radical thermal polymerization initiators include diacyl peroxide (acetyl peroxide, benzoyl peroxide, etc.), ketone peroxide (methyl ethyl ketone peroxide, cyclohexanone peroxide, etc.), hydroperoxide (hydrogen peroxide, tert. -Butyl hydroxide, cumene hydroperoxide, etc.), dialkyl peroxides (di-tert-butyl peroxide, dicumyl peroxide, dilauroyl peroxide, etc.), peroxyesters (tert-butyl peroxyacetate, tert) -Butyl peroxypivalate, etc.), azo compounds (azobisisobutyronitrile, azobisisovaleronitrile, etc.), persulfates (ammonium persulfate, sodium persulfate) And potassium persulfate) and the like. Such radical thermal polymerization initiators can be used singly or in combination of two or more.

  The radical polymerization method is not particularly limited, and an emulsion polymerization method, a suspension polymerization method, a bulk polymerization method, a solution polymerization method, and the like can be employed. The solution polymerization, which is a typical radical polymerization method, will be described more specifically. The outlines of other polymerization methods are the same, and details thereof are described, for example, in “Polymer Science Experimental Method” edited by Polymer Society (Tokyo Kagaku Dojin, 1981).

  An organic solvent is used for solution polymerization. These organic solvents can be arbitrarily selected as long as the objects and effects of the present invention are not impaired. These organic solvents are usually organic compounds having a boiling point in the range of 50 ° C. to 200 ° C. under atmospheric pressure, and organic compounds that uniformly dissolve each component are preferable. Examples of preferable organic solvents include alcohols such as isopropanol and butanol, ethers such as dibutyl ether, ethylene glycol dimethyl ether, tetrahydrofuran and dioxane, ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone and cyclohexanone, ethyl acetate and acetic acid. Examples thereof include esters such as butyl, amyl acetate and γ-butyrolactone, and aromatic hydrocarbons such as benzene, toluene and xylene. In addition, these organic solvents can be used individually by 1 type or in combination of 2 or more types. Furthermore, a water-mixed organic solvent in which water is used in combination with the above organic solvent is also applicable from the viewpoint of the solubility of the monomer and the polymer to be produced.

  Further, the solution polymerization conditions are not particularly limited, but for example, it is preferable to heat for 10 minutes to 30 hours within a temperature range of 50 ° C to 200 ° C. Furthermore, in order not to deactivate the generated radicals, it is preferable to perform an inert gas purge not only during solution polymerization but also before the start of solution polymerization. Usually, nitrogen gas is suitably used as the inert gas.

In order to obtain the fluoroaliphatic group-containing polymer in the present invention within a preferable molecular weight range, a radical polymerization method using a chain transfer agent is particularly effective.
As chain transfer agents, mercaptans (for example, octyl mercaptan, decyl mercaptan, dodecyl mercaptan, tert-dodecyl mercaptan, octadecyl mercaptan, thiophenol, p-nonylthiophenol, etc.), polyhalogenated alkyls (for example, carbon tetrachloride, chloroform, etc.) , 1,1,1-trichloroethane, 1,1,1-tribromooctane, etc.) and low-activity monomers (α-methylstyrene, α-methylstyrene dimer, etc.) can be used, preferably carbon These are mercaptans of 4-16. The amount of these chain transfer agents used is remarkably influenced by the activity of the chain transfer agent, the combination of the monomers, the polymerization conditions and the like, and must be precisely controlled. It is about 01 mol% to 50 mol%, preferably 0.05 mol% to 30 mol%, particularly preferably 0.08 mol% to 25 mol%. These chain transfer agents may be present in the system simultaneously with the target monomer whose degree of polymerization is to be controlled in the polymerization process, and the addition method is not particularly limited. It may be added after being dissolved in the monomer, or may be added separately from the monomer.

  The fluoroaliphatic group-containing polymer in the present invention preferably has a viscosity at 25 ° C. of 200 Pa · s to 10,000 Pa · s. When the viscosity of the fluoroaliphatic group-containing polymer at 200C is 200 Pa · s to 10000 Pa · s, a good surface shape can be obtained. The viscosity of the fluoroaliphatic group-containing polymer is more preferably 250 Pa · s to 5000 Pa · s, and still more preferably 300 Pa · s to 1000 Pa · s. In the present invention, the “viscosity” of the fluoroaliphatic group-containing polymer is determined using a VAR-100 rheometer manufactured by Rheology, a distance between gaps of 1.5 mm, a frequency of 1 Hz, a strain of 0.005, and a heating rate of 5 ° C./min. The value measured by the oscillation mode under the condition of nitrogen atmosphere.

The weight average molecular weight of the fluoroaliphatic group-containing polymer in the present invention is preferably 1,000,000 or less. More preferred is a weight average molecular weight of 500,000 or less, and particularly preferred is a weight average molecular weight of 100,000 or less. The lower limit of the weight average molecular weight of the fluoroaliphatic group-containing polymer is 5,000.
The weight average molecular weight can be measured as a value in terms of polyethylene oxide (PEO) using gel permeation chromatography (GPC).

The colored curable composition of this invention should just contain at least 1 sort (s) of fluoro aliphatic group containing polymer, and may contain 2 or more types.
In the colored curable composition of the present invention, the addition amount of the fluoroaliphatic group-containing polymer is preferably 0.01% by mass to 20% by mass of the solid content mass of the composition, preferably 0.01% by mass to 5 mass% is more preferable and 0.01 mass%-1 mass% are still more preferable.

  Moreover, the preferable range of the concentration C mass% of the fluoroaliphatic group-containing polymer in the solid content mass of the composition varies depending on the fluorine content F% in the fluoroaliphatic group-containing polymer. In order to further improve the coated surface state, the product of the concentration C% by mass of the fluoroaliphatic group-containing polymer and the fluorine content F% in the fluoroaliphatic group-containing polymer is 0.05 to 0.12. It is preferable that it is 0.06 to 0.09, more preferably 0.06 to 0.08. When C × F is within the above range, the surface shape of the coating film can be further improved.

[(A) Colorant]
The colored curable composition of the present invention contains (A) a colorant. As the colorant, pigments and dyes can be used.

(Pigment)
As a pigment that can be used in the colored curable composition of the present invention, various conventionally known inorganic pigments or organic pigments can be used. Moreover, considering that it is preferable that the pigment has a high transmittance regardless of whether it is an inorganic pigment or an organic pigment, it is preferable to use a pigment having a particle size as small as possible and a handling property in consideration of handling properties. Then, it is preferably a pigment having an average primary particle diameter of 0.01 μm to 0.3 μm, more preferably 0.01 μm to 0.15 μm. When the particle size is within the above range, the transmittance is high, the color characteristics are good, and it is effective for forming a color filter with high contrast.
The average primary particle diameter is obtained by observing with an SEM or TEM, measuring 100 particle sizes in a portion where the particles are not aggregated, and calculating an average value.

  Examples of the inorganic pigment include metal compounds represented by metal oxides, metal complex salts, and the like. Specifically, iron, cobalt, aluminum, cadmium, lead, copper, titanium, magnesium, chromium, zinc, antimony And metal oxides such as the above, and complex oxides of the above metals.

Examples of the organic pigment include:
C. I. Pigment Red 1, 2, 3, 4, 5, 6, 7, 9, 10, 14, 17, 22, 23, 31, 38, 41, 48: 1, 48: 2, 48: 3, 48: 4 49, 49: 1, 49: 2, 52: 1, 52: 2, 53: 1, 57: 1, 60: 1, 63: 1, 66, 67, 81: 1, 81: 2, 81: 3 83, 88, 90, 105, 112, 119, 122, 123, 144, 146, 149, 150, 155, 166, 168, 169, 170, 171, 172, 175, 176, 177, 178, 179, 184 185, 187, 188, 190, 200, 202, 206, 207, 208, 209, 210, 216, 220, 224, 226, 242, 246, 254, 255, 264, 270, 272, 279,
C. I. Pigment Yellow 1, 2, 3, 4, 5, 6, 10, 11, 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, 168, 169, 170, 171, 172, 173, 17 , 175,176,177,179,180,181,182,185,187,188,193,194,199,213,214
C. I. Pigment Orange 2, 5, 13, 16, 17: 1, 31, 34, 36, 38, 43, 46, 48, 49, 51, 52, 55, 59, 60, 61, 62, 64, 71, 73,
C. I. Pigment Green 7, 10, 36, 37,
C. I. Pigment Blue 1, 2, 15, 15: 1, 15: 2, 15: 3, 15: 4, 15: 6, 16, 22, 60, 64, 66, 79, 79 were changed to OH. Things, 80,
C. I. Pigment Violet 1, 19, 23, 27, 32, 37, 42,
C. I. Pigment Brown 25, 28,
C. I. Pigment Black 1, 7 and the like.

Among these, the pigments that can be preferably used include the following. However, the present invention is not limited to these.
C. I. Pigment Yellow 11, 24, 108, 109, 110, 138, 139, 150, 151, 154, 167, 180, 185,
C. I. Pigment Orange 36, 71,
C. I. Pigment Red 122, 150, 171, 175, 177, 209, 224, 242, 254, 255, 264,
C. I. Pigment Violet 19, 23, 32,
C. I. Pigment Blue 15: 1, 15: 3, 15: 6, 16, 22, 60, 66,
C. I. Pigment Green 7, 36, 37,
C. I. Pigment Black 1, 7

-Finer pigments-
In the present invention, if necessary, a fine and sized organic pigment can be used. The refinement of the pigment is a step of preparing a highly viscous liquid composition together with the pigment, the water-soluble organic solvent, and the water-soluble inorganic salt, and grinding the pigment using the liquid composition.

  Water-soluble organic solvents include methanol, ethanol, isopropanol, n-propanol, isobutanol, n-butanol, ethylene glycol, diethylene glycol, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, diethylene glycol monobutyl ether, propylene glycol, propylene glycol A monomethyl ether acetate etc. can be mentioned. However, if it is adsorbed to the pigment by using a small amount and does not flow away into the wastewater, benzene, toluene, xylene, ethylbenzene, chlorobenzene, nitrobenzene, aniline, pyridine, quinoline, tetrahydrofuran, dioxane, ethyl acetate, isopropyl acetate, butyl acetate, hexane , Heptane, octane, nonane, decane, undecane, dodecane, cyclohexane, methylcyclohesasan, halogenated hydrocarbon, acetone, methyl ethyl ketone, methyl isobutyl ketone, cyclohexanone, dimethylformamide, dimethyl sulfoxide, N-methylpyrrolidone, etc. Two or more kinds of solvents may be mixed and used as necessary.

  In the present invention, examples of the water-soluble inorganic salt include sodium chloride, potassium chloride, calcium chloride, barium chloride, sodium sulfate and the like.

The amount of the water-soluble inorganic salt used is 1 to 50 times the mass of the pigment, and a larger amount has a grinding effect, but a more preferred amount is 1 to 10 times the mass in terms of productivity, and further moisture. Is preferably 1% or less.
The amount of the water-soluble organic solvent used is in the range of 50% by mass to 300% by mass and preferably in the range of 100% by mass to 200% by mass with respect to the pigment.

  After preparing a liquid composition using each of the above components, the pigment is refined by a wet pulverizer. Here, there is no particular limitation on the operating conditions of the wet pulverizing apparatus, but in order to effectively proceed the grinding with the pulverizing media, the operating condition when the apparatus is a kneader is that the rotational speed of the blade in the apparatus is 10 rpm to 200 rpm is preferable, and a relatively large biaxial rotation ratio is preferable because the grinding effect is large. The operation time is preferably 1 to 8 hours in combination with the dry pulverization time, and the internal temperature of the apparatus is preferably 50 to 150 ° C. Further, the water-soluble inorganic salt that is a pulverizing medium preferably has a pulverized particle size of 5 μm to 50 μm, a sharp particle size distribution, and a spherical shape.

-Preparation of pigment (color matching)-
The organic pigment as the colorant can be used alone, but can be used in various combinations in order to increase color purity. Specific examples of combinations are shown below.
For example, as a red pigment, an anthraquinone pigment, a perylene pigment, and a diketopyrrolopyrrole pigment may be used alone, but at least one of them, a disazo yellow pigment, an isoindoline yellow pigment, a quinophthalone pigment A yellow pigment, or a perylene red pigment, an anthraquinone red pigment, or a diketopyrrolopyrrole red pigment may be mixed. For example, as an anthraquinone pigment, C.I. I. Pigment Red 177, and perylene pigments include C.I. I. Pigment red 155, C.I. I. Pigment Red 224, and diketopyrrolopyrrole pigments include C.I. I. Pigment Red 254, and C.I. I. Pigment yellow 83, C.I. I. Pigment yellow 139, or C.I. I. Mixing with Pigment Red 177 is preferred.
The mass ratio of the red pigment to the other pigment is preferably 100: 5 to 100: 80. If it is less than 100: 5, it may be difficult to suppress the light transmittance from 400 nm to 500 nm, and the color purity may not be increased. On the other hand, if the ratio exceeds 100: 80, the coloring power may decrease. Particularly, the mass ratio is optimally in the range of 100: 10 to 100: 65. In addition, in the case of the combination of red pigments, it can adjust according to chromaticity.

As the green pigment, a halogenated phthalocyanine pigment may be used alone, but a mixture of this with a disazo yellow pigment, a quinophthalone yellow pigment, an azomethine yellow pigment, or an isoindoline yellow pigment. May be performed. For example, C.I. I. Pigment Green 7, 36, 37 and C.I. I. Pigment yellow 83, C.I. I. Pigment yellow 138, C.I. I. Pigment yellow 139, C.I. I. Pigment yellow 150, C.I. I. Pigment yellow 180, or C.I. I. Mixing with Pigment Yellow 185 is preferred.
The mass ratio of the green pigment to the yellow pigment is preferably 100: 5 to 100: 200. If the mass ratio is less than 100: 5, it is difficult to suppress the light transmittance of 400 nm to 450 nm, and the color purity may not be increased. On the other hand, if the ratio exceeds 100: 200, the dominant wavelength tends to be longer and the deviation from the NTSC target hue may become larger. The mass ratio is particularly preferably in the range of 100: 20 to 100: 150.

As the blue pigment, a phthalocyanine pigment may be used alone, but it may be mixed with a dioxazine purple pigment. As a particularly preferred example, C.I. I. Pigment blue 15: 6 and C.I. I. A mixture with pigment violet 23 can be mentioned.
The mass ratio of the blue pigment to the violet pigment is preferably 100: 0 to 100: 100, more preferably 100: 70 or less.

Moreover, as a pigment suitable for black matrix use, carbon black, graphite, titanium black, iron oxide, titanium oxide alone or a mixture thereof can be used, and a combination of carbon black and titanium black is preferable.
The mass ratio of carbon black to titanium black is preferably in the range of 100: 0 to 100: 60. If it is 100: 61 or more, the dispersion stability may decrease.

(dye)
In the present invention, when a dye is used as the colorant (A), a uniformly curable colored curable composition is obtained.
There is no restriction | limiting in particular as dye which can be used as a coloring agent, The well-known dye conventionally used as a color filter use can be used. For example, Japanese Patent Application Laid-Open No. 64-90403, Japanese Patent Application Laid-Open No. 64-91102, Japanese Patent Application Laid-Open No. 1-94301, Japanese Patent Application Laid-Open No. 6-11614, No. 2592207, US Pat. No. 4,808,501. Specification, US Pat. No. 5,667,920, US Pat. No. 5,059,500, JP-A-5-333207, JP-A-6-35183, JP-A-6-51115 JP-A-6-194828, JP-A-8-21599, JP-A-4-249549, JP-A-10-123316, JP-A-11-302283, JP-A-7-286107, JP 2001-4823, JP-A-8-15522, JP-A-8-29771, JP-A-8-146215, JP-A-11-3434. 7, JP-A-8-62416, JP-A-2002-14220, JP-A-2002-14221, JP-A-2002-14222, JP-A-2002-14223, JP-A-8-302224 JP-A-8-73758, JP-A-8-179120, JP-A-8-151531, and the like.
The chemical structure includes pyrazole azo, anilino azo, triphenyl methane, anthraquinone, anthrapyridone, benzylidene, oxonol, pyrazolotriazole azo, pyridone azo, cyanine, phenothiazine, pyrrolopyrazole azomethine, A dye such as xanthene, phthalocyanine, benzopyran, or indigo can be used.

(Pigment dispersion)
In the present invention, when a pigment is used as the colorant (A), it is preferable to prepare the colored curable composition of the present invention using a pigment dispersion prepared in advance.
The content of the pigment in the pigment dispersion is preferably 10% by mass to 60% by mass and more preferably 15% by mass to 50% by mass with respect to the total solid content (mass) of the composition. When the pigment content is within the above range, the color density is sufficient and it is effective to ensure excellent color characteristics.

-Dispersant-
The pigment dispersion in the present invention preferably contains at least one dispersant. By containing this dispersant, the dispersibility of the pigment can be improved.
As the dispersant, for example, a known pigment dispersant or surfactant can be appropriately selected and used.

  Specifically, many types of compounds can be used. For example, organosiloxane polymer KP341 (manufactured by Shin-Etsu Chemical Co., Ltd.), (meth) acrylic acid (co) polymer polyflow No. 75, no. 90, no. Cationic surfactants such as 95 (manufactured by Kyoeisha Chemical Industry Co., Ltd.) and W001 (manufactured by Yusho Co., Ltd.); polyoxyethylene lauryl ether, polyoxyethylene stearyl ether, polyoxyethylene oleyl ether, polyoxyethylene Nonionic surfactants such as octylphenyl ether, polyoxyethylene nonylphenyl ether, polyethylene glycol dilaurate, polyethylene glycol distearate, and sorbitan fatty acid ester; anionic systems such as W004, W005, and W017 (manufactured by Yusho Co., Ltd.) Surfactant: EFKA-46, EFKA-47, EFKA-47EA, EFKA polymer 100, EFKA polymer 400, EFKA polymer 401, EFKA polymer 450 (all manufactured by Ciba Specialty Chemicals) Polymer dispersants such as Disperse Aid 6, Disperse Aid 8, Disperse Aid 15, Disperse Aid 9100 (all manufactured by San Nopco); Solsperse 3000, 5000, 9000, 12000, 13240, 13940, 17000, 24000, Various Solsperse dispersants (manufactured by Nippon Lubrizol Co., Ltd.) such as 26000, 28000; Adeka Pluronic L31, F38, L42, L44, L61, L64, F68, L72, P95, F77, P84, F87, P94, L101, P103, F108, L121, P-123 (Asahi Denka Co., Ltd.) and Isonet S-20 (Sanyo Kasei Co., Ltd.), Disperbyk 101, 103, 106, 108, 109, 111, 112, 116, 130, 140, 142, 162, 163, 164, 166, 167, 170, 171, 174, 176, 180, 182, 2000, 2001, 2050, 2150 (by Big Chemie). In addition, an oligomer or polymer having a polar group at the molecular end or side chain, such as an acrylic copolymer, may be mentioned.

  As content in the pigment dispersion liquid of a dispersing agent, 1 mass%-100 mass% are preferable with respect to the mass of the above-mentioned pigment, and 3 mass%-70 mass% are more preferable.

-Pigment derivative-
A pigment derivative is added to the pigment dispersion in the present invention as necessary. By adsorbing a pigment derivative having a part having affinity for the dispersant or a polar group to the pigment surface and using this as the adsorption point of the dispersant, the pigment is made into fine particles in the pigment dispersion or colored. It can be dispersed in the curable composition to prevent reaggregation. As a result, this colored curable composition can be preferably used when forming a color filter having high contrast and excellent transparency.

  Specifically, the pigment derivative is a compound in which an organic pigment is used as a base skeleton, and an acidic group, a basic group, or an aromatic group is introduced into a side chain as a substituent. Specific examples of organic pigments include quinacridone pigments, phthalocyanine pigments, azo pigments, quinophthalone pigments, isoindoline pigments, isoindolinone pigments, quinoline pigments, diketopyrrolopyrrole pigments, and benzoimidazolone pigments. Is mentioned. In general, light yellow aromatic polycyclic compounds such as naphthalene series, anthraquinone series, triazine series and quinoline series which are not called pigments are also included.

  Examples of pigment derivatives include JP-A-11-49974, JP-A-11-189732, JP-A-10-245501, JP-A-2006-265528, JP-A-8-295810, and JP-A-11-199796. For example, JP-A-2005-234478, JP-A-2003-240938, and JP-A-2001-356210 can be used.

  As content in the pigment dispersion liquid of a pigment derivative, 1 mass%-30 mass% are preferable with respect to the mass of a pigment, and 3 mass%-20 mass% are more preferable. When the content is within the above range, the dispersion can be favorably performed while the viscosity is kept low, the dispersion stability after dispersion can be improved, and the color characteristics with high transmittance can be obtained. When producing a filter, it can be configured to have high contrast with good color characteristics.

-Distribution method-
As a method for dispersing the pigment, for example, a bead disperser using a zirconia bead (for example, a disperse mat manufactured by GETZMANN), which is prepared by mixing a pigment and a dispersant and previously dispersing the mixture with a homogenizer or the like, is used. And a fine dispersion method is used.
The dispersion time is preferably about 3 to 6 hours.

[(B) Photopolymerizable compound]
The colored curable composition of the present invention contains (B) a photopolymerizable compound.
The photopolymerizable compound is preferably a compound having at least one addition-polymerizable ethylenically unsaturated group and having a boiling point of 100 ° C. or higher at normal pressure, and more preferably a tetrafunctional or higher functional acrylate compound. .

Examples of the compound having at least one addition-polymerizable ethylenically unsaturated group and having a boiling point of 100 ° C. or higher at normal pressure include, for example, polyethylene glycol mono (meth) acrylate, polypropylene glycol mono (meth) acrylate, phenoxy Monofunctional acrylates and methacrylates such as ethyl (meth) acrylate; polyethylene glycol di (meth) acrylate, trimethylolethane tri (meth) acrylate, neopentyl glycol di (meth) acrylate, pentaerythritol tri (meth) acrylate, penta Erythritol tetra (meth) acrylate, dipentaerythritol hexa (meth) acrylate, hexanediol (meth) acrylate, trimethylolpropane tri (acryloyloxypropyl) ester Ter, tri (acryloyloxyethyl) isocyanurate, polyfunctional alcohols such as glycerin and trimethylol ethane, added with ethylene oxide and propylene oxide and then (meth) acrylated, poly (pentaerythritol or dipentaerythritol) (Meth) acrylate, urethane acrylates described in JP-B-48-41708, JP-B-50-6034, JP-A-51-37193, JP-A-48-64183, JP-B-49-43191 Polyfunctional acrylates and methacrylates such as polyester acrylates described in JP-B-52-30490 and epoxy acrylates which are reaction products of epoxy resins and (meth) acrylic acid can be mentioned.
Furthermore, the Japan Adhesion Association Vol. 20, no. 7, pages 300 to 308 which are introduced as photocurable monomers and oligomers can also be used.

  In addition, a compound which has been (meth) acrylated after adding ethylene oxide or propylene oxide to the polyfunctional alcohol described in JP-A-10-62986 as general formulas (1) and (2) together with specific examples thereof. Can be used.

Among these, dipentaerythritol penta (meth) acrylate, dipentaerythritol hexa (meth) acrylate, and a structure in which these acryloyl groups are via ethylene glycol and propylene glycol residues are preferable. These oligomer types can also be used.
Also, urethane acrylates such as those described in JP-B-48-41708, JP-A-51-37193, JP-B-2-32293, and JP-B-2-16765, JP-B-58-49860, Urethane compounds having an ethylene oxide skeleton described in JP-B-56-17654, JP-B-62-39417, and JP-B-62-39418 are also suitable. Further, by using addition polymerizable compounds having an amino structure or a sulfide structure in the molecule described in JP-A-63-277653, JP-A-63-260909, and JP-A-1-105238, It is possible to obtain a photopolymerizable composition excellent in the photosensitive speed. Commercially available products include urethane oligomer UAS-10, UAB-140 (manufactured by Sanyo Kokusaku Pulp Co., Ltd.), UA-7200 "(manufactured by Shin-Nakamura Chemical Co., Ltd., DPHA-40H (manufactured by Nippon Kayaku Co., Ltd.), UA-306H, UA- 306T, UA-306I, AH-600, T-600, AI-600 (manufactured by Kyoeisha) and the like.
In addition, ethylenically unsaturated compounds having an acid group are also suitable. Examples of commercially available products include TO-756, which is a carboxyl group-containing trifunctional acrylate manufactured by Toagosei Co., Ltd., and a carboxyl group-containing pentafunctional acrylate. Some TO-1382 and the like can be mentioned.

The photopolymerizable compound can be used in combination of two or more, in addition to being used alone.
The content of the photopolymerizable compound in the colored curable composition is preferably 5% by mass to 50% by mass, more preferably 7% by mass to 40% by mass, and more preferably 10% by mass. It is still more preferable that it is mass%-35 mass%.

[(C)]
The colored curable composition of the present invention contains (C) a photopolymerization initiator.
Examples of the photopolymerization initiator include halomethyl oxadiazole described in JP-A-57-6096, halomethyl-s-triazine described in JP-B-59-1281, JP-A-53-133428, and the like. Isoactive halogen compounds, aromatic carbonyl compounds such as ketals, acetals, or benzoin alkyl ethers described in US Pat. No. 4,318,791 and European Patent Application No. 88050, described in US Pat. No. 4,199,420 Aromatic ketone compounds such as benzophenones, (thio) xanthones or acridine compounds described in French Patent No. 2456741, coumarins or lophine dimers described in JP-A-10-62986, etc. Compound, sulfonium organoboron such as JP-A-8-015521 Body, etc., etc. can be mentioned.

  Examples of the photopolymerization initiator include acetophenone, ketal, benzophenone, benzoin, benzoyl, xanthone, triazine, halomethyloxadiazole, acridine, coumarins, lophine dimers, biphenyl Imidazole type, oxime ester type and the like are preferable.

  Examples of the acetophenone photopolymerization initiator include 2,2-diethoxyacetophenone, p-dimethylaminoacetophenone, 2-hydroxy-2-methyl-1-phenyl-propan-1-one, p-dimethylaminoacetophenone, Preferable examples include 4′-isopropyl-2-hydroxy-2-methyl-propiophenone.

  Preferable examples of the ketal photopolymerization initiator include benzyl dimethyl ketal and benzyl-β-methoxyethyl acetal.

  Examples of the benzophenone photopolymerization initiator include benzophenone, 4,4 ′-(bisdimethylamino) benzophenone, 4,4 ′-(bisdiethylamino) benzophenone, 4,4′-dichlorobenzophenone, and 1-hydroxy-cyclohexyl. -Phenyl-ketone, 2-benzyl-2-dimethylamino-1- (4-morpholinophenyl) -butanone-1, 2-tolyl-2-dimethylamino-1- (4-morpholinophenyl) -butanone-1 2-methyl-1- [4- (methylthio) phenyl] -2-morpholinopropanone-1 and the like can be preferably exemplified.

  Preferred examples of the benzoin-based or benzoyl-based photopolymerization initiator include benzoin isopropyl ether, zenzoin isobutyl ether, benzoin methyl ether, methyl o-benzoyl bezoate, and the like.

  Preferable examples of the xanthone photopolymerization initiator include diethylthioxanthone, diisopropylthioxanthone, monoisopropylthioxanthone, chlorothioxanthone, and the like.

  Examples of the triazine photopolymerization initiator include 2,4-bis (trichloromethyl) -6-p-methoxyphenyl-s-triazine, 2,4-bis (trichloromethyl) -6-p-methoxystyryl- s-triazine, 2,4-bis (trichloromethyl) -6- (1-p-dimethylaminophenyl) -1,3-butadienyl-s-triazine, 2,4-bis (trichloromethyl) -6-biphenyl- s-triazine, 2,4-bis (trichloromethyl) -6- (p-methylbiphenyl) -s-triazine, p-hydroxyethoxystyryl-2,6-di (trichloromethyl) -s-triazine, methoxystyryl- 2,6-di (trichloromethyl-s-triazine, 3,4-dimethoxystyryl-2,6-di (trichloromethyl) -s-to Azine, 4-benzoxolane-2,6-di (trichloromethyl) -s-triazine, 4- (o-bromo-pN, N- (diethoxycarbonylamino) -phenyl) -2,6-di (Chloromethyl) -s-triazine, 4- (pN, N- (diethoxycarbonylamino) -phenyl) -2,6-di (chloromethyl) -s-triazine and the like can be preferably exemplified.

  Examples of the halomethyloxadiazole-based photopolymerization initiator include 2-trichloromethyl-5-styryl-1,3,4-oxodiazole, 2-trichloromethyl-5- (cyanostyryl) -1,3. , 4-oxodiazole, 2-trichloromethyl-5- (naphth-1-yl) -1,3,4-oxodiazole, 2-trichloromethyl-5- (4-styryl) styryl-1,3 A preferred example is 4-oxodiazole.

  Preferred examples of the acridine-based photopolymerization initiator include 9-phenylacridine, 1,7-bis (9-acridinyl) heptane, and the like.

  Examples of the coumarin-based photopolymerization initiator include 3-methyl-5-amino-((s-triazin-2-yl) amino) -3-phenylcoumarin, 3-chloro-5-diethylamino-((s Preferred examples include -triazin-2-yl) amino) -3-phenylcoumarin, 3-butyl-5-dimethylamino-((s-triazin-2-yl) amino) -3-phenylcoumarin, and the like.

  Examples of the lophine dimer-based photopolymerization initiator include 2- (o-chlorophenyl) -4,5-diphenylimidazolyl dimer and 2- (o-methoxyphenyl) -4,5-diphenylimidazolyl dimer. And 2- (2,4-dimethoxyphenyl) -4,5-diphenylimidazolyl dimer and the like can be preferably exemplified.

  Preferable examples of the biimidazole photopolymerization initiator include 2-mercaptobenzimidazole, 2,2′-benzothiazolyl disulfide and the like.

  In addition to the above, 1-phenyl-1,2-propanedione-2- (o-ethoxycarbonyl) oxime, O-benzoyl-4 ′-(benzmercapto) benzoyl-hexyl-ketoxime, 2,4,6-trimethylphenyl Examples thereof include carbonyl-diphenyl phosphonyl oxide and hexafluorophospho-trialkylphenyl phosphonium salt.

In this invention, it is not limited to the above photoinitiator, Other well-known things can also be used. For example, vicinal polykettle aldonyl compounds described in US Pat. No. 2,367,660, and α-carbonyl compounds described in US Pat. Nos. 2,367,661 and 2,367,670. An acyloin ether described in US Pat. No. 2,448,828, an α-hydrocarbon substituted aromatic acyloin compound described in US Pat. No. 2,722,512, US Pat. , 046,127 and 2,951,758, the triarylimidazole dimer / p-aminophenyl ketone combination described in US Pat. No. 3,549,367, Benzothiazole compounds / trihalomethyl-s-triazine compounds described in JP-A-51-48516; C. S. Perkin II (1979) 1653-1660, J. MoI. C. S. Examples include Perkin II (1979) 156-162, Journal of Photopolymer Science and Technology (1995) 202-232, and oxime ester compounds described in JP-A No. 2000-66385.
Moreover, these photoinitiators can also be used together.

  As content in the colored curable composition of a photoinitiator, 0.1 mass%-10.0 mass% are preferable with respect to the total solid of this composition, More preferably, it is 0.5 mass%. It is -5.0 mass%. When the content of the photopolymerization initiator is within the above range, the polymerization reaction can proceed well to form a film with good strength.

[Optional ingredients]
Hereinafter, the colored curable composition of the present invention may optionally contain components such as a binder polymer (alkali-soluble resin) and a solvent in addition to the components (A) to (D) described above.
Hereinafter, optional components that can be added to the colored curable composition of the present invention will be described.

(Binder polymer)
The colored curable composition of the present invention may contain an alkali-soluble resin as a binder polymer.
The alkali-soluble resin is a linear organic polymer, and promotes at least one alkali-solubility in a molecule (preferably a molecule having an acrylic copolymer or a styrene copolymer as a main chain). It can be appropriately selected from alkali-soluble resins having a group (for example, carboxyl group, phosphoric acid group, sulfonic acid group, etc.). Of these, more preferred are those which are soluble in an organic solvent and can be developed with a weak alkaline aqueous solution.

  For production of the alkali-soluble resin, for example, a known radical polymerization method can be applied. Polymerization conditions such as temperature, pressure, type and amount of radical initiator, type of solvent, etc. when producing an alkali-soluble resin by radical polymerization can be easily set by those skilled in the art, and the conditions are determined experimentally. It can also be done.

  As said linear organic high molecular polymer, the polymer which has carboxylic acid in a side chain is preferable. For example, it is described in JP-A-59-44615, JP-B-54-34327, JP-B-58-12577, JP-B-54-25957, JP-A-59-53836, and JP-A-59-71048. Methacrylic acid copolymer, acrylic acid copolymer, itaconic acid copolymer, crotonic acid copolymer, maleic acid copolymer, partially esterified maleic acid copolymer, etc., as well as in the side chain Preferred examples include acidic cellulose derivatives having a carboxylic acid, those obtained by adding an acid anhydride to a polymer having a hydroxyl group, and a polymer having a (meth) acryloyl group in the side chain.

Of these, benzyl (meth) acrylate / (meth) acrylic acid copolymers and multi-component copolymers composed of benzyl (meth) acrylate / (meth) acrylic acid / other monomers are particularly suitable.
In addition, those obtained by copolymerizing 2-hydroxyethyl methacrylate are also useful. The polymer can be used by mixing in an arbitrary amount.

  In addition to the above, 2-hydroxypropyl (meth) acrylate / polystyrene macromonomer / benzyl methacrylate / methacrylic acid copolymer, 2-hydroxy-3-phenoxypropyl acrylate / polymethyl methacrylate described in JP-A-7-140654 Macromonomer / benzyl methacrylate / methacrylic acid copolymer, 2-hydroxyethyl methacrylate / polystyrene macromonomer / methyl methacrylate / methacrylic acid copolymer, 2-hydroxyethyl methacrylate / polystyrene macromonomer / benzyl methacrylate / methacrylic acid copolymer Etc.

  As a specific structural unit of the alkali-soluble resin, a copolymer of (meth) acrylic acid and another monomer copolymerizable therewith is particularly suitable. Here, (meth) acrylic acid is a general term that combines acrylic acid and methacrylic acid, and (meth) acrylate is also a general term for acrylate and methacrylate.

Examples of other monomers copolymerizable with the (meth) acrylic acid include alkyl (meth) acrylates, aryl (meth) acrylates, and vinyl compounds. Here, the hydrogen atom of the alkyl group and the aryl group may be substituted with a substituent.
Specific examples of the alkyl (meth) acrylate and aryl (meth) acrylate include methyl (meth) acrylate, ethyl (meth) acrylate, propyl (meth) acrylate, butyl (meth) acrylate, isobutyl (meth) acrylate, pentyl ( Examples include meth) acrylate, hexyl (meth) acrylate, octyl (meth) acrylate, phenyl (meth) acrylate, benzyl (meth) acrylate, tolyl (meth) acrylate, naphthyl (meth) acrylate, cyclohexyl (meth) acrylate, and the like. it can.

Examples of the vinyl compound include styrene, α-methylstyrene, vinyl toluene, glycidyl methacrylate, acrylonitrile, vinyl acetate, N-vinyl pyrrolidone, tetrahydrofurfuryl methacrylate, polystyrene macromonomer, polymethyl methacrylate macromonomer, CH _2. = CR ³¹ R ³² , CH ₂ = C (R ³¹ ) (COOR ³³ ) [wherein R ³¹ represents a hydrogen atom or an alkyl group having 1 to 5 carbon atoms, and R ³² is an aromatic group having 6 to 10 carbon atoms. Represents a hydrocarbon ring, and R ³³ represents an alkyl group having 1 to 8 carbon atoms or an aralkyl group having 6 to 12 carbon atoms. ], Etc. can be mentioned.

These other copolymerizable monomers can be used singly or in combination of two or more. Other preferred copolymerizable monomers are selected from CH ₂ ═CR ³¹ R ³² , CH ₂ ═C (R ³¹ ) (COOR ³³ ), phenyl (meth) acrylate, benzyl (meth) acrylate and styrene. It is at least one, and particularly preferably, CH ₂ = CR ³¹ R ³² and / or CH ₂ = C (R ³¹ ) (COOR ³³ ).

  As content in the colored curable composition of alkali-soluble resin, 1 mass%-15 mass% are preferable with respect to the total solid of this composition, More preferably, they are 2 mass%-12 mass%. Especially preferably, it is 3 mass%-10 mass%.

(solvent)
The colored curable composition of the present invention can contain a solvent, if necessary.
Examples of the solvent include esters such as ethyl acetate, n-butyl acetate, isobutyl acetate, amyl formate, isoamyl acetate, isobutyl acetate, butyl propionate, isopropyl butyrate, ethyl butyrate, butyl butyrate, alkyl esters, methyl lactate, and lactic acid. 3 such as ethyl, methyl oxyacetate, ethyl oxyacetate, butyl oxyacetate, methyl methoxyacetate, ethyl methoxyacetate, butyl methoxyacetate, methyl ethoxyacetate, ethyl ethoxyacetate, methyl 3-oxypropionate, ethyl 3-oxypropionate -Oxypropionic acid alkyl esters; methyl 3-methoxypropionate, ethyl 3-methoxypropionate, methyl 3-ethoxypropionate, ethyl 3-ethoxypropionate, methyl 2-oxypropionate, 2-oxypropion Ethyl, propyl 2-oxypropionate, methyl 2-methoxypropionate, ethyl 2-methoxypropionate, propyl 2-methoxypropionate, methyl 2-ethoxypropionate, ethyl 2-ethoxypropionate, 2-oxy-2- Methyl methyl propionate, ethyl 2-oxy-2-methylpropionate, methyl 2-methoxy-2-methylpropionate, ethyl 2-ethoxy-2-methylpropionate, methyl pyruvate, ethyl pyruvate, propyl pyruvate, Methyl acetoacetate, ethyl acetoacetate, methyl 2-oxobutanoate, ethyl 2-oxobutanoate and the like; ethers such as diethylene glycol dimethyl ether, tetrahydrofuran, ethylene glycol monomethyl ether, ethylene glycol monoethyl ether Ter, methyl cellosolve acetate, ethyl cellosolve acetate, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, diethylene glycol monobutyl ether, propylene glycol methyl ether acetate, propylene glycol ethyl ether acetate, propylene glycol propyl ether acetate, etc .; ketones such as methyl ethyl ketone, cyclohexanone, 2-heptanone, 3-heptanone, etc .; aromatic hydrocarbons such as toluene, xylene and the like.

Of these, methyl 3-ethoxypropionate, ethyl 3-ethoxypropionate, ethyl cellosolve acetate, ethyl lactate, diethylene glycol dimethyl ether, butyl acetate, methyl 3-methoxypropionate, 2-heptanone, cyclohexanone, ethyl carbitol acetate, butyl Carbitol acetate, propylene glycol methyl ether acetate and the like are suitable.
You may use a solvent in combination of 2 or more types besides using independently.
In addition, you may use these solvents when preparing the above-mentioned pigment dispersion liquid.

(Other ingredients)
In the colored curable composition of the present invention, if necessary, a thermal polymerization initiator, a thermal polymerization component, a thermal polymerization inhibitor, other fillers, a polymer compound other than the above alkali-soluble resin, an adhesion promoter, an oxidation agent Various additives such as an inhibitor, an ultraviolet absorber and an aggregation inhibitor can be contained.

-Thermal polymerization initiator-
It is also effective to contain a thermal polymerization initiator in the colored curable composition of the present invention.
Examples of the thermal polymerization initiator include various azo compounds and peroxide compounds. Examples of the azo compounds include azobis compounds. Examples of the peroxide compounds include ketones. Examples thereof include peroxides, peroxyketals, hydroperoxides, dialkyl peroxides, diacyl peroxides, peroxyesters, peroxydicarbonates, and the like.

-Thermal polymerization component-
It is also effective to contain a thermal polymerization component in the colored curable composition of the present invention in order to improve the film strength.
An epoxy compound is used as the thermal polymerization component. The epoxy compound is a compound having two or more epoxy rings in the molecule such as bisphenol A type, cresol novolac type, biphenyl type, and alicyclic epoxy compound.
Specifically, for example, as bisphenol A type, Epototo YD-115, YD-118T, YD-127, YD-128, YD-134, YD-8125, YD-7011R, ZX-1059, YDF-8170, YDF-170 and the like (manufactured by Tohto Kasei), Denacol EX-1101, EX-1102, EX-1103 and the like (manufactured by Nagase Kasei), Plaxel GL-61, GL-62, G101 and G102 (manufactured by Daicel Chemical) In addition, these similar bisphenol F type and bisphenol S type can also be mentioned. Epoxy acrylates such as Ebecryl 3700, 3701, 600 (manufactured by Daicel UC) may also be used.

Examples of the cresol novolak type include Epototo YDPN-638, YDPN-701, YDPN-702, YDPN-703, YDPN-704, etc. (manufactured by Toto Kasei), Denacol EM-125, etc. (manufactured by Nagase Kasei),
As the biphenyl type, 3,5,3 ′, 5′-tetramethyl-4,4′diglycidylbiphenyl, etc.
Examples of the alicyclic epoxy compounds include Celoxide 2021, 2081, 2083, 2085, Epolide GT-301, GT-302, GT-401, GT-403, EHPE-3150 (manufactured by Daicel Chemical), Santo Tote ST-3000, ST. -4000, ST-5080, ST-5100 (manufactured by Tohto Kasei) and the like.
1,1,2,2-tetrakis (p-glycidyloxyphenyl) ethane, tris (p-glycidyloxyphenyl) methane, triglycidyltris (hydroxyethyl) isocyanurate, o-phthalic acid diglycidyl ester, terephthalic acid Diglycidyl ester, amine type epoxy resins such as Epototo YH-434 and YH-434L, and glycidyl ester obtained by modifying dimer acid in the skeleton of bisphenol A type epoxy resin can also be used.

-Thermal polymerization inhibitor-
A thermal polymerization inhibitor may be added to the colored curable composition of the present invention.
Examples of the thermal polymerization inhibitor include hydroquinone, p-methoxyphenol, di-t-butyl-p-cresol, pyrogallol, t-butylcatechol, benzoquinone, 4,4'-thiobis (3-methyl-6-t- Butylphenol), 2,2′-methylenebis (4-methyl-6-tert-butylphenol), 2-mercaptobenzimidazole, and the like are useful.

(Preparation of colored curable composition)
The colored curable composition of the present invention is added to (A) a colorant, (B) a photopolymerizable compound, (C) a photopolymerization initiator, and (D) a fluoroaliphatic group-containing polymer (preferably together with a solvent). It can be prepared by mixing and dispersing arbitrary components and mixing and dispersing using various mixers and dispersers. In particular, when the colorant (A) is a pigment, it is preferable to prepare a pigment dispersion in advance and use it.
The mixing and dispersing step preferably comprises kneading and dispersing followed by fine dispersion treatment, but kneading and dispersing can be omitted.

An example of a method for preparing the colored curable composition of the present invention is shown below.
A mixture of a pigment, a water-soluble organic solvent and a water-soluble inorganic salt is mixed into a kneader such as a two-roll, three-roll, ball mill, tron mill, disper, kneader, kneader, homogenizer, blender, single-screw or twin-screw extruder. Is used to grind the pigment while applying a strong shearing force, and then the mixture is put into water and made into a slurry with a stirrer or the like. Next, the slurry is filtered and washed with water to remove the water-soluble organic solvent and the water-soluble inorganic salt, and then dried to obtain a finer pigment. In addition, it is also possible to omit the process which refines | miniaturizes this pigment.

The beads are dispersed with a pigment and a dispersant and / or a pigment derivative and a solvent. Mainly using a vertical or horizontal sand grinder, pin mill, slit mill, ultrasonic disperser, etc., and finely dispersing with beads made of 0.01 mm to 1 mm particle size glass, zirconia, etc., pigment dispersion Get.
For details on kneading and dispersing, see T.W. C. “Paint Flow and Pigment Dispersion” by Patton (published by John Wiley and Sons, 1964) and the like.
And, after adding (B) photopolymerizable compound, (C) photopolymerization initiator, (D) fluoroaliphatic group-containing polymer, and optional components to the pigment dispersion obtained as described above, By passing through the mixing and dispersing step, the colored curable composition of the present invention can be obtained.

<Coloring pattern, color filter, and manufacturing method thereof>
The colored pattern of the present invention is formed by the above-described colored curable composition of the present invention.
The obtained colored pattern can suppress the surface deterioration due to coating and can form a colored film with few defects. As a result, the coloring pattern of the present invention can be applied to a pixel portion of a color filter.

The color filter of the present invention has a colored pattern formed on the substrate by the above-described colored curable composition of the present invention.
Further, the method for producing a color filter of the present invention includes a step of applying the above-described colored curable composition of the present invention by a spin coating method, a slit-and-spin method, or a die coating method, and a colored pattern on a substrate. It is characterized by forming.
Hereinafter, the color filter of the present invention will be described in detail through its manufacturing method (color filter manufacturing method of the present invention).

As a method for producing the color filter of the present invention, first, the colored curable composition of the present invention is applied directly or via another layer to a substrate by a spin coating method, a slit-and-spin method, or a die coating method. The process of apply | coating is performed. In this step, after a photocurable coating film is formed on the substrate, the coating film is exposed through a predetermined mask pattern. After exposure, the uncured portion is developed and removed with a developer to form a colored pattern. By repeating such steps, pixel portions (colored patterns) of each color (three colors or four colors) are formed on the substrate, and a color filter can be obtained.
By the above method, a color filter used for a liquid crystal display element or a solid-state image sensor can be manufactured with high quality and low cost with little difficulty in process.
Hereinafter, each process of application | coating, exposure, and image development is demonstrated.

[Coating process]
In the coating step, the colored curable composition of the present invention is coated on the substrate using a spin coating method, a slit-and-spin method, or a die coating method.
In the coating step, the colored curable composition of the present invention is coated on the substrate using a spin coating method, a slit-and-spin method, or a die coating method.
In the case of the slit-and-spin method or the die coating method, the conditions vary depending on the size of the coated substrate. For example, when a fifth generation glass substrate (1100 mm × 1250 mm) is coated by the die coating method, coloring from the slit nozzle The discharge amount of the curable composition is usually 500 microliters / second to 2000 microliters / second, preferably 800 microliters / second to 1500 microliters / second, and the coating speed is usually 50 mm / second. Second to 300 mm / second, preferably 100 mm / second to 200 mm / second. The solid content of the colored curable composition is usually 10% by mass to 20% by mass, preferably 13% by mass to 18% by mass.
When a 3.5th generation glass substrate 720 mm × 600 mm is applied by a spin coating method, the discharge amount of the colored curable composition from the nozzle is usually 40 cc to 50 cc, and the coating rotation speed is 500 rpm to 1000 rpm. . The solid content of the colored curable composition is usually 15% by mass to 25% by mass, and preferably 18% by mass to 22% by mass.

  When forming the coating film by the colored curable composition of this invention on a board | substrate, as thickness (after a prebaking process) of this coating film, it is generally 0.3 micrometer-5.0 micrometers, Preferably 0.5 micrometer-4 0.0 μm, most desirably 0.8 μm to 3.0 μm.

Next, the board | substrate with which the colored curable composition of this invention is apply | coated is demonstrated.
As the substrate in the present invention, for example, non-alkali glass, soda glass, Pyrex (registered trademark) glass, quartz glass, and those obtained by attaching a transparent conductive film thereto, a solid-state imaging device, etc. Examples of the photoelectric conversion element substrate used in the present invention include a silicon substrate and a plastic substrate. On these substrates, usually, a black matrix for isolating each pixel may be formed, or a transparent resin layer may be provided for promoting adhesion.
The plastic substrate preferably has a gas barrier layer and / or a solvent resistant layer on its surface.

In addition, the color curable property of the present invention is also applied to a driving substrate (hereinafter referred to as “TFT type liquid crystal driving substrate”) on which a thin film transistor (TFT) of a thin film transistor (TFT) type color liquid crystal display device is arranged. A colored pattern can be formed by the composition to produce a color filter. Examples of the substrate in the TFT type liquid crystal driving substrate include glass, silicon, polycarbonate, polyester, aromatic polyamide, polyamideimide, and polyimide. These substrates may be subjected to appropriate pretreatment such as chemical treatment with a silane coupling agent or the like, plasma treatment, ion plating, sputtering, gas phase reaction method, vacuum deposition, etc., if desired. For example, a substrate on which a passivation film such as a silicon nitride film is formed on the surface of the TFT liquid crystal driving substrate or on the surface of the driving substrate can be used.
When a colored pattern is formed on the TFT type liquid crystal driving substrate using the colored curable composition of the present invention, the photomask used for exposure has a pattern for forming pixels. In addition, it is preferable that a pattern for forming a through hole or a U-shaped depression is also provided.

After the photocurable coating film is formed as described above, a pre-bake treatment is usually performed. If necessary, vacuum treatment can be performed before pre-baking. The vacuum drying conditions are such that the degree of vacuum is usually about 0.1 to 1.0 torr, preferably about 0.2 to 0.5 torr.
The pre-bake treatment can be performed using a hot plate, an oven or the like in a temperature range of 50 ° C. to 140 ° C. (preferably 70 ° C. to 110 ° C.) for 10 seconds to 300 seconds. Here, a high-frequency treatment or the like may be used in combination with the pre-bake treatment. The high frequency treatment can be used alone.

[Exposure process]
In the exposure step, after a photocurable coating film is formed on the substrate, the coating film is exposed through a predetermined mask pattern.
In this case, ultraviolet rays such as g-line, h-line, i-line and j-line are particularly preferable as the radiation to be used. When manufacturing a color filter for a liquid crystal display device, it is preferable that exposure using mainly h-line and i-line is performed by a proximity exposure machine and a mirror projection exposure machine.

[Development process]
In the development step, the uncured portion after exposure is eluted in the developer, leaving only the cured portion.
The development temperature is usually 20 ° C. to 30 ° C., and the development time is 20 seconds to 90 seconds.
Moreover, as a developing solution, what melt | dissolves the coating film of the photocurable colored curable composition in an uncured part, On the other hand, what can melt | dissolve a hardening part can be used. Specifically, a combination of various organic solvents or an alkaline aqueous solution can be used.

As said organic solvent, the above-mentioned solvent which can be used when preparing the pigment dispersion liquid or colored curable composition in this invention is mentioned.
Examples of the alkaline aqueous solution include sodium hydroxide, potassium hydroxide, sodium carbonate, sodium hydrogencarbonate, sodium oxalate, sodium metasuccinate, aqueous ammonia, ethylamine, diethylamine, dimethylethanolamine, tetramethylammonium hydroxide, Concentration of an alkaline compound such as tetraethylammonium hydroxide, choline, pyrrole, piperidine, 1,8-diazabicyclo- [5,4,0] -7-undecene is 0.001% by mass to 10% by mass, preferably 0.8%. An alkaline aqueous solution dissolved so as to be 01% by mass to 1% by mass can be mentioned. An appropriate amount of a water-soluble organic solvent such as methanol or ethanol, a surfactant, or the like can be added to the alkaline aqueous solution.

The development method may be any of a dip method, a shower method, a spray method, and the like, and may be combined with a swing method, a spin method, an ultrasonic method, or the like. Before the developer is touched, the surface to be developed can be previously moistened with water or the like to prevent uneven development.
It is also possible to develop with the substrate tilted.

After the development processing, after a rinsing step for washing and removing excess developer, drying is performed, and then heat treatment (post-baking) is performed to complete the curing.
The rinsing process is usually performed with pure water, but in order to save liquid, pure water is used in the final cleaning, and at the beginning of cleaning, used pure water is used. Sound wave irradiation can be used together.

  After the rinsing step, after draining and drying, a heat treatment is usually performed at about 200 ° C. to 250 ° C. In this heat treatment (post-bake), the coating film after development is continuously or batch-treated using a heating means such as a hot plate, a convection oven (hot air circulation dryer) or a high-frequency heater so as to satisfy the above conditions. It can be done with an expression.

  By sequentially repeating the above operation for each color in accordance with the desired number of hues, a color filter in which a plurality of colored patterns (pixels) are formed can be produced.

Although the application of the colored curable composition of the present invention has been described mainly focusing on the application to a color filter, it can also be applied to the formation of a black matrix that isolates each colored pixel constituting the color filter.
The black matrix exposes and develops the pigment dispersion in the present invention using a black pigment such as carbon black or titanium black as a pigment, and then further post-bake as necessary to promote film hardening. Can be formed.

<Liquid crystal display element>
The liquid crystal display element of the present invention comprises the color filter of the present invention.
More specifically, an alignment film is formed on the inner surface side of the color filter of the present invention, is opposed to the electrode substrate, and a gap is filled with liquid crystal and sealed to obtain a panel which is the liquid crystal display element of the present invention. It is done.

  The present invention will be described more specifically with reference to the following examples. The materials, reagents, amounts and ratios of substances, operations, and the like shown in the following examples can be appropriately changed without departing from the gist of the present invention. Therefore, the scope of the present invention is not limited to the following specific examples. In the following, all parts and% are based on mass unless otherwise specified.

Example 1
Green pigment C.I. I. 200 parts of Pigment Green 36, 1600 parts of sodium chloride, and 360 parts of diethylene glycol were charged into a 1 gallon kneader (manufactured by Inoue Seisakusho) and kneaded at 50 ° C. for 8 hours. Next, this kneaded product is poured into 10 liters of warm water, stirred for 2 hours while heating to 80 ° C. to form a slurry, repeatedly filtered and washed with water to remove sodium chloride and diethylene glycol, and then dried at 60 ° C. overnight. 190 parts of a green pigment were obtained.
The yellow pigment C.I. I. 200 parts of Pigment Yellow 138, 2000 parts of sodium chloride, and 360 parts of diethylene glycol were charged into a 1 gallon kneader (manufactured by Inoue Seisakusho) and kneaded at 50 ° C. for 8 hours. Next, this kneaded product is poured into 10 liters of warm water, stirred for 2 hours while heating to 80 ° C. to form a slurry, repeatedly filtered and washed with water to remove sodium chloride and diethylene glycol, and then dried at 60 ° C. overnight. 190 parts of a yellow pigment were obtained.
With the following composition, using a homogenizer, the rotational speed was 3,000 r. p. m. And mixed for 3 hours to prepare a mixed solution.

〔composition〕
Pigment Green 36 (average primary particle diameter 25 nm) ... 66 parts Pigment Yellow 138 (average primary particle diameter 25 nm) ... 68 parts phthalocyanine derivative (manufactured by Solsperse 3000) ... 10 parts benzyl methacrylate / methyl methacrylate (= 70 / 30 [molar ratio]) copolymer (weight average molecular weight: 30,000) ... 32 parts Dispersant (BYK-161, manufactured by BYK) ... 10 parts propylene glycol monomethyl ether acetate ... 720 parts

  Subsequently, the mixed solution obtained above was further subjected to co-dispersion treatment for 6 hours in a bead disperser Ultra Apex Mill (manufactured by Kotobuki Kogyo Co., Ltd.) using 0.1 mmφ zirconia beads.

  Components of the following composition were further added to the obtained pigment dispersion and mixed by stirring to prepare a colored curable composition (color resist solution) of the present invention.

〔composition〕
Dipentaerythritol pentahexaacrylate 72 parts Photopolymerization initiator A: 1,2-octanedione, 1- [4- (phenylthio) phenyl]-, 2- (O-benzoyloxime) 4.5 parts Photopolymerization initiator B: 2-benzyl-2-dimethylamino-1- (4-morpholinophenyl) -butanone-1 15 parts Photopolymerization initiator C: diethylthioxanthone 4.5 parts benzyl methacrylate / methacrylic Acid (= 70/30 [molar ratio]) copolymer (weight average molecular weight: 30,000) ... 172 parts · Propylene glycol monomethyl ether acetate · 106 parts · Epoxy resin: (trade name EHPE3150 manufactured by Daicel Chemical Industries) ... 11 parts・ Fluoroaliphatic group-containing polymer (P-7, Mw = 15000)... 0.18 part. 3-Eto Xylethyl propionate ... 814 parts

(Examples 2-15, Comparative Examples 1-4)
In Example 1, the fluoroaliphatic group-containing polymer P-7 was changed to various polymers (fluoroaliphatic group-containing polymer or comparative polymer) as shown in Table 2 below. Except having changed suitably as shown in 2, it carried out similarly to Example 1, and prepared the colored curable composition (color resist liquid) of an Example and a comparative example.

(Production and evaluation of evaluation samples)
-1. Evaluation of radiation stripes (straight stripes) and pinholes (white spots)
Each of the colored curable compositions (color resist solutions) prepared in each Example and Comparative Example was spin-coated on a 550 mm × 650 mm glass substrate (1737, manufactured by Corning) at a rotational speed of 740 rpm to 850 rpm, 90 After drying (prebaking) in an oven at 60 ° C. for 60 seconds, a coating film having a thickness of 1.3 μm was obtained.
The surface of the coating film was observed visually and with an optical microscope, and evaluated for radiation streaks and pinholes (white spots). The evaluation index is as follows.

(Radiation streaks)
◎: No radiation streaks ○: Slightly at the end ×: Located at the end and center

(Pinhole)
◎: Not observed at all ○: Slightly observed but acceptable range ×: Observed and exceeded acceptable range

-2. Fabrication and evaluation of colored filter substrate
The colored curable composition (color resist solution) prepared in each Example and Comparative Example was spin-coated on a 550 mm × 650 mm glass substrate (1737, manufactured by Corning) at a rotation speed of 740 rpm to 850 rpm, and 90 ° C. In an oven for 60 seconds (pre-baking). Thereafter, the entire surface of the coating film was exposed at 200 mJ / cm ² (illuminance 20 mW / cm ² ), and the coated film after the exposure was a 1% aqueous solution of alkali developer CDK-1 (manufactured by Fuji Film Electronics Materials Co., Ltd.). And rested for 60 seconds. After standing still, pure water was sprayed in a shower to wash away the developer. The coating film that has been exposed and developed as described above is heat-treated in an oven at 220 ° C. for 1 hour (post-baking) to form a colored resin film for forming a color filter on the glass substrate. A substrate (color filter) was produced.
The surface state of the obtained color filter was observed with a sodium lamp and an optical microscope, and image defects (surface luminance unevenness, pinholes) were evaluated. The evaluation index is as follows.

(Image defect)
◎: No defect ○: Slightly observed but acceptable range ×: Observed and exceeded acceptable range

  Table 2 below shows the evaluation results of the radiation streaks (straight stripes) and pinholes (white spots) obtained as described above, and the evaluation results of the image defects of the color filter.

  The structures of the comparative polymers Pc-1 and Pc-2 used in Comparative Examples 1 to 4 shown in Table 2 are shown below.

  As shown in Table 2, the colored curable composition using the (D) fluoroaliphatic group-containing polymer in the present invention has no radiation streaks when applied, has a good surface shape, and has pinholes (white spots). It can be seen that a good coating film can be formed. Moreover, it turned out that the image defect of the coloring pattern after post-baking is also suppressed, and it turned out that an excellent color filter can be manufactured.

Claims (7)

(A) a colorant, (B) a photopolymerizable compound, (C) a photopolymerization initiator, and (D) a copolymer containing a repeating unit represented by the following general formula (1) A colored curable composition.

(In General Formula (1), R ¹ represents a hydrogen atom or a methyl group, X ¹ represents an oxygen atom, a sulfur atom, or —N (R) —, and m 1 represents an integer of 0 to 18. , N1 represents an integer of 1 to 18. Here, R represents a hydrogen atom or an optionally substituted alkyl group having 1 to 8 carbon atoms. 2. The coloring according to claim 1, wherein the copolymer containing the repeating unit represented by the general formula (1) is a copolymer containing a repeating unit represented by the following general formula (2). Curable composition.

(In general formula (2), i and j each represent an integer of 1 or more, meaning that each repeating unit contains i and j types, respectively. A and b are mass percentages representing the polymerization ratio. Σai represents a numerical value of 1% by mass to 98% by mass, Σbj represents a numerical value of 1% by mass to 98% by mass, R ¹ , R ² , and R ³ each represent a hydrogen atom or a methyl group, X ¹ and ^{X 2} are each an oxygen atom, a sulfur atom, or -N (R) - represents, m1 represents an integer of 0 to 18, n1 and m2 each represent an integer of 1 to 18, p And q each represents an integer of 1 to 20. Here, R represents a hydrogen atom or an optionally substituted alkyl group having 1 to 8 carbon atoms.   The copolymer containing the repeating unit represented by the general formula (1) is contained in an amount of 0.01% by mass to 20% by mass with respect to the total solid content in the composition. Item 3. The colored curable composition according to Item 2.   The coloring pattern formed with the colored curable composition of any one of Claims 1-3.   A color filter comprising the colored pattern according to claim 4 on a substrate.   A step of applying the colored curable composition according to any one of claims 1 to 3 by a spin coating method, a slit-and-spin method, or a die coating method, and forming a colored pattern on the substrate A method for producing a color filter, comprising:   A liquid crystal display element using the color filter according to claim 6.