JP2003192948A - Ink composition for inkjet recording, used for color filter, color filter and its production process - Google Patents

Abstract

<P>PROBLEM TO BE SOLVED: To provide an ink composition for forming the pixel for a color filter by an inkjet recording method, a color filter having a colored cured coating film of this ink composition, having high color purity, color density and transparency and excellent in heat resistance, solvent resistance or chemical resistance, and light resistance, and a process for producing the color filter. <P>SOLUTION: The ink composition for inkjet recording, used for a color filter contains a halogenated metal phthalocyanine of a specified metal other than copper, in place of a halogenated copper phthalocyanine hitherto used, and an amino resin having a carboxy group or a phenolic hydroxy group. The color filter provided has a cured coating layer of the ink composition. A process for producing the color filter is provided. <P>COPYRIGHT: (C)2003,JPO

Description

Detailed Description of the Invention

[0001]

BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a color filter used for a color liquid crystal display, a color scanner, a solid-state image pickup device, and the like, and more specifically, it is suitable for applications requiring durability after a pattern forming step by an inkjet method. INKJET INK COMPOSITION FOR COLOR FILTER, COLOR FILTER AND PROCESS FOR PRODUCING COLOR FILTER HAVING DIFFERENT DURATION

[0002]

2. Description of the Related Art A color filter is provided on a transparent substrate provided with a black matrix so as to selectively transmit the three primary colors of red, green and blue, or to the three colors of cyan, magenta and yellow. It is formed by disposing a coloring material in each pixel portion so as to selectively reflect the primary colors. The fields of application of these are color liquid crystal displays, color scanners, solid-state imaging devices, and the like.

As a method for forming a color filter, a photolithography method, an electrodeposition method, a printing method, an ink jet method and the like are known, and at present, the photolithography method is predominant, which is a photocurable coloring composition. This is a method with many steps of forming a color filter by repeating the steps of applying an object to a substrate, performing pattern exposure, and then dissolving and washing the unexposed portion for red, blue, green or cyan, magenta, and yellow. In contrast,
The inkjet method, which can form pixels of red, blue, green or cyan, magenta, and yellow in one step, has attracted attention because it has a small number of steps and low cost.

Regarding the color filter forming method by the ink jet method, JP-A-59-75205, JP-A-61-245106 and JP-A-63-2945.
No. 03 gazette discloses a color filter produced by an inkjet method using a dye ink. However, since the colorant is a dye, the color filter obtained by these methods has heat resistance and solvent resistance. Inferior to. On the other hand, various methods using a resin and a pigment have been proposed as a method for obtaining a colored layer having higher heat resistance and solvent resistance. For example, JP-A-5-224007 discloses a color filter using an inkjet ink composed of a melamine resin and a colorant, and JP-A-8-171010 discloses a heat- or photo-curable inkjet ink containing an acrylamide polymer. The color filter using
JP-A-10-17813 discloses a color filter using an inkjet ink containing a melamine resin, a polycarboxylic acid derivative, and an amine-based stabilizer as main components, and JP-A-7-188596 discloses. , A thermosetting ink containing a thermosetting resin and a specific amine as a dispersant is disclosed.

With the recent increase in the size of LCDs, many of the characteristics required of color filter materials are related to the manufacturing process of color liquid crystal displays.
Vapor deposition or sputtering process of transparent electrodes such as TO,
Alternatively, heat resistance required in the baking step, solvent resistance required in the washing step and alignment film coating step, and light resistance because light transmitted through the color filter becomes image information when displaying an image.

When an ink jet ink containing an acrylic resin is used, it has a drawback that the resin is easily decomposed when the temperature exceeds 200 ° C. On the other hand, Japanese Patent Laid-Open No. 5-
No. 224007 discloses an ink jet ink using a thermosetting resin such as a melamine resin for the purpose of improving heat resistance. In this method, in the ink,
An organic acid or an inorganic acid, or an amine salt or ammonium salt thereof, etc. is added as a curing accelerator, and these remain as impurities in the cured coating film and contaminate the sputtering device during formation of the ITO transparent electrode, or It has drawbacks such as impairing the storage stability of the inkjet ink.

On the other hand, in the production of a color filter using the ink jet method, an ink jet ink using a conventional organic solvent pollutes the environment. Therefore, a method using an aqueous ink has been disclosed. JP-A-8-319
Japanese Patent No. 444 discloses a coating composition for a black matrix containing an aqueous pigment ink. further,
Japanese Patent Application Laid-Open No. 10-96810 discloses a method of forming a color filter by exposing a polysilane photosensitive layer to ultraviolet rays to form a hydrophilic latent image and then developing the hydrophilic latent image with a hydrophilic ink. However, the ink film obtained by these methods is inferior in durability against high temperature heating during vapor deposition, sputtering or firing of the transparent electrode.

As a colorant used for a color filter, a pigment having excellent light resistance has come to be mainly used in place of a dye which has been frequently used conventionally. Generally, a halogenated copper phthalocyanine pigment is widely used as a colorant used for forming a green pixel of a color filter. Copper phthalocyanine is a polycyclic aromatic ring compound having four isoindole structures around a copper atom, and the aromatic ring has a total of 16 hydrogen atoms which can be substituted with halogen atoms and the like. The halogenated copper phthalocyanine is a copper phthalocyanine in which some or all of the 16 hydrogen atoms contained in the copper phthalocyanine are replaced with chlorine or bromine atoms, and the halogenated copper phthalocyanine has chlorine atoms or bromine atoms introduced at various ratios. It consists of a mixture of phthalocyanines.

It is known that this conventional halogenated copper phthalocyanine pigment uses bromine as a halogen, and a green color with a stronger yellowish color is obtained as the bromination rate increases, but sometimes the reddish color becomes stronger. There is a problem in that the color tone is unstable, such as the color is lost, and the transparency is lowered.

Recently, the color liquid crystal display, which is the largest use of color filters, has come to be used in color monitors and color televisions, and color liquid crystal displays are strongly required to have color reproducibility in addition to the conventionally required characteristics. There is. Therefore, the colorant used for the color filter is also required to have high color purity and color density and high transparency. However, in the case of using a conventional halogenated copper phthalocyanine pigment whose color development is unstable, it was difficult to satisfy these requirements only by introducing a cross-linking structure effective for improving the heat resistance of colored pixels. .

Under such a background, color purity, color density,
And high transparency, further, an inkjet ink composition for a color filter capable of forming a colored cured film layer having high heat resistance and solvent resistance, and using the same, high color purity, color density and transparency, A highly practical color filter having excellent heat resistance, solvent resistance, chemical resistance, and light resistance is desired.

[0012]

An object of the present invention is to provide a color filter having pixels formed by an ink jet method, in which the pixel portion has high color purity, color density and transparency. Furthermore, an inkjet ink composition for a color filter capable of forming a colored cured film layer having both high heat resistance and solvent resistance, and using the same, high color purity, color density and transparency,
A highly practical color filter having a pixel portion having excellent heat resistance, solvent resistance or chemical resistance, and light resistance, and a method for producing the color filter.

[0013]

In order to solve the above problems, the present invention provides (a) a halogenated phthalocyanine represented by the following general formula (1) and (b) an amino resin having a carboxyl group or a phenolic hydroxyl group. An inkjet ink composition for a color filter, which comprises and.

In order to solve the above problems, the present invention provides (a) a halogenated phthalocyanine represented by the following general formula (1) and (b) an amino group having a carboxyl group or a phenolic hydroxyl group on a transparent substrate. Provided is a color filter having a colored cured film layer of an inkjet ink composition for a color filter containing a resin.
Furthermore, the present invention uses an inkjet ink composition for a color filter, which comprises, on a transparent substrate, a halogenated phthalocyanine represented by the following general formula (1) and (b) an amino resin having a carboxyl group or a phenolic hydroxyl group. A method for producing a color filter, which comprises forming a colored film layer of the inkjet ink composition for a color filter by an inkjet recording method and then curing the colored film layer.

[0015]

[Chemical 2] (1) (where M is Al, Si, Sc, Ti, V, Fe, C
o, Ni, Zn, Ga, Ge, Y, Zr, Nb, In,
It represents one metal selected from Sn and Pb or two hydrogen atoms. X _{1 to} X ₁₆ are hydrogen, fluorine, chlorine, bromine,
Alternatively, it represents an atom selected from iodine, and the total sum of halogen atoms is an integer of 8 to 16. Y represents fluorine, chlorine, bromine, iodine, oxygen, or a hydroxyl group, and m represents an integer of 0-2. )

[0016]

BEST MODE FOR CARRYING OUT THE INVENTION The present invention will be described in more detail below. Hereinafter, unless otherwise specified, the “ink jet ink composition for a color filter of the present invention” is simply abbreviated as “ink composition (a)”, and the “halogenated phthalocyanine represented by the general formula (1)” is Abbreviated as "phthalocyanine (a)"

The phthalocyanine (a) used in the ink composition (a) includes Al, Si, and M as M in the general formula (1).
Sc, Ti, V, Fe, Co, Ni, Zn, Ga, G
It is a halogenated metal phthalocyanine having one central metal selected from the group consisting of e, Y, Zr, Nb, In, Sn and Pb, or a halogenated metal-free phthalocyanine having two hydrogen atoms. Among them, a metal halide phthalocyanine having Zn, Ni, or Al as a central metal is particularly preferable because of high color purity, color density, and transparency.

In the general formula (1), in the case of a halogenated metal-free phthalocyanine in which M is two hydrogen atoms and a halogenated phthalocyanine in which M is a divalent metal, m is
Is 0 and there is no ligand Y. When M is a metal phthalocyanine having a valence of 3 or more, the ligand Y is coordinated to M.
That is, when the valence of M is trivalent, Y1 valences are monovalent, and when the valence of M is tetravalent, Y2 valences are monovalent or divalent. Y1 coordinate.

Examples of Y include fluorine, chlorine, bromine, iodine, oxygen, and a hydroxyl group. When Y is a hydroxyl group, a dehydration reaction may occur to form a dimer or a multimer. The phthalocyanine (a) used in the present invention is XnP.
When simply described as cMYm, when the valence of M is trivalent, the reaction of the following general formula (2) proceeds and XnPc
It may form a dimer represented by MOMPcXn. Here, Pc means phthalocyanine, and Xn is n
Represents substituted halogen atoms, and M, Y and m each represent M, Y and m in the general formula (1).

[0020]

Embedded image 2XnPcMOH → XnPcMOMPcXn + H ₂ O (2)

When M is a metal having a valence of 4 or more, the reaction represented by the following general formula (3) proceeds and HOXnPcMO (Xn
PcMO) _Z-2 XnPcMOH may form a multimer.

[0022]

Embedded image zXnPcM (OH) ₂ → HOXnPcMO (XnPcMO) _Z-2 XnP cMOH + (z-2) / 2 · H ₂ O (3)

Furthermore, when M is a metal having a valence of 4 or more and the ligand Y is a hydroxyl group, a dehydration reaction represented by the following general formula (4) often occurs to form a μ-oxo form.

[0024]

Embedded image XnPcM (OH) ₂ → XnPcM = O + H ₂ O (4)

In the phthalocyanine (a) used in the present invention, when M is a metal having a valence of 3 or more, a halogenated metal phthalocyanine having fluorine, chlorine, bromine, iodine or oxygen as a ligand is easily produced. , Easy to obtain.

In the present invention, when the film thickness of the green ink composition (a) cured film layer is constant, the CIE color system chromaticity (Y, x, y value) having a large y value is defined as "color purity". Is high ”. Further, when the film thickness of the pigment-dispersed resist cured coating film is determined so that the x and y values are constant, a thin film thickness is referred to as "high color density", and a large Y value is referred to as "high color density". It is highly transparent. "

The phthalocyanine (a) includes 8 to 16 fluorine, chlorine, and
It has a bromine or iodine atom. All the substituted halogen atoms may be the same or different, but preferably have 8 or more bromine atoms and 1 or more chlorine. Among them, 12 or more bromine atoms and 2 chlorine atoms
Those having one or more have a highly transparent green color and are suitable as a green colorant for a color filter.

The phthalocyanine (a) has a narrower half-value width of the spectral transmission spectrum than the conventional copper halide phthalocyanine and a large maximum transmittance. This indicates that the phthalocyanine (a) exhibits a green color with higher color purity and color density and higher transparency than the conventional halogenated copper phthalocyanine. Specifically, by using phthalocyanine (a) as a colorant, the wavelength (Tmax) at which the transmittance of the spectral transmission spectrum at 380 to 780 nm becomes maximum, which is not achieved by the conventional halogenated copper phthalocyanine, is 520. ~ 5
A color filter having a green pixel of 90 nm, a transmittance at Tmax of 70% or more, and a transmittance of a spectral transmission spectrum at a wavelength of 650 to 700 nm of 20% or less can be simply and inexpensively obtained. .

The phthalocyanine (a) can be produced by a known method for producing a halogenated metal phthalocyanine, such as the chlorosulfonic acid method or the halogenated phthalonitrile method. In the ink composition (a) of the present invention, in addition to the phthalocyanine (a) as a colorant,
A yellow pigment can be mixed and used. A desired hue can be obtained by changing the mixing ratio of the phthalocyanine (a) and the yellow pigment depending on the application.

The yellow pigment that can be used in the present invention includes
C. I. Pigment Yellow 83, C.I. I. Pigment Yellow 128, C.I. I. Pigment Yellow 13
8, C.I. I. Pigment Yellow 139, C.I. I. Pigment Yellow 150, C.I. I. Pigment Yellow 1
80, C.I. I. Pigment Yellow 185 and other yellow organic pigments.

These yellow pigments may be used alone or in combination of two or more. Among the above pigments, C.I. I. Pigment Yellow 138, C.I.
I. Pigment Yellow 139, C.I. I. Pigment Yellow 150 is particularly preferable because it has excellent color purity and transparency.

The blending ratio of the yellow pigment can be appropriately selected according to the application, but when generally used for a color filter, it is in the range of 10 to 70% with respect to the total mass of the phthalocyanine (a) and the yellow pigment. It is preferable that
It is more preferably in the range of 30 to 60%.

Generally, the smaller the particle size of a pigment used in an inkjet ink composition for a color filter in a dispersed state, the higher the transparency of a color filter pixel portion obtained by using the pigment. Therefore, the primary particle size of the phthalocyanine (a) is 10 to 100 nm.
Is preferable, and a range of 30 to 50 nm is particularly preferable. When the primary particle size of the pigment dispersed in the inkjet ink composition for a color filter exceeds 100 nm, the transparency of the color filter pixel portion formed using this decreases, and when it is less than 10 nm. ,
The viscosity of the pigment dispersion composition increases with time, thixotropy appears strongly, and the pigment is likely to aggregate, so that in the dispersed state, secondary particles having a large particle size may be formed. In this case, it also causes a decrease in the transparency of the color filter pixel portion.

To achieve such a particle size, dispersion treatment using a ball mill, sand mill, peas mill, three rolls, paint shaker, attritor, dispersion stirrer, ultrasonic wave or the like is effective.

In the present invention, phthalocyanine (a)
Further, (b) an amino resin having a carboxyl group or a phenolic hydroxyl group, a solvent, and optionally other pigments and various additives are mixed to prepare a pigment dispersion composition. The amino resin having a carboxyl group or a phenolic hydroxyl group (hereinafter abbreviated as amino resin (b)) used in the present invention includes, for example, (1) an amino compound having a carboxyl group or a phenolic hydroxyl group,
It can be produced by a method of condensing an aldehyde compound or (2) a method of condensing an aldehyde compound having a carboxyl group or a phenolic hydroxyl group with an amino compound.

Examples of the amino compound having a carboxyl group include 2-, 3-, or 4- (4,6-diamino-1,3,5-triazin-2-yl) benzoic acid, 5-methyl-2. -(4,6-diamino-1,3,5
-Triazin-2-yl) benzoic acid, 4-methoxy-2
-(4,6-Diamino-1,3,5-triazine-2-
Yl) benzoic acid, 2-methyl-4- (4,6-diamino-1,3,5-triazin-2-yl) benzoic acid, 2-
Chloro-4- (4,6-diamino-1,3,5-triazin-2-yl) benzoic acid and the like can be mentioned. As the amino compound having a phenolic hydroxyl group, for example,
2-, 3-, or 4- (4,6-diamino-1,3,3
5-triazin-2-yl) phenol, 4-methyl-
2- (4,6-diamino-1,3,5-triazine-2
-Yl) phenol, 2-methoxy-4- (4,6-diamino-1,3,5-triazin-2-yl) phenol, 3-chloro-4- (4,6-diamino-1,3,5
-Triazin-2-yl) phenol and the like.

Examples of the aldehyde compound having a carboxyl group include glyoxylic acid and its hydrate, succinosemialdehyde and the like. Examples of the aldehyde compound having a phenolic hydroxyl group include 2-, 3-, or 4-hydroxybenzaldehyde, 3,4-, 3,5-, 2,5-, or 2,4-
Examples thereof include dihydroxybenzaldehyde and 2,4,6-trihydroxybenzaldehyde.

As the aldehyde compound, in addition to the above-mentioned aldehyde compound having a carboxyl group or a phenolic hydroxyl group, for example, formaldehyde, paraformaldehyde, acetaldehyde, propionaldehyde, butyraldehyde, glyoxal; formaldehyde condensation such as trioxane and paraformaldehyde. Body; aqueous solution such as formaldehyde aqueous solution; methyl hemiformal, n-butyl hemiformal, isobutyl hemiformal, and the like.

As the amino compound, in addition to the above-mentioned amino compound having a carboxyl group or a phenolic hydroxyl group, for example, urea, melamine, benzoguanamine, acetoguanamine, cyclohexanecarboguanamine, phthaloguanamine, steroguanamine, spiroguanamine and the like can be mentioned. .

When the amino resin (b) is produced by the above method (1) or (2), a plurality of amino compounds or a plurality of aldehyde compounds can be used. For example, benzoguanamine and 4- (4,6-diamino-1,3,5-triazin-2-yl) benzoic acid can be used in a desired ratio, or formaldehyde and glyoxylic acid can be used in a desired ratio. As described above, by using a plurality of raw material amino compounds or aldehyde compounds, the acid value of the resulting amino resin can be adjusted and the solubility of the amino resin (b) in a solvent can be controlled.

The amino resin (b) obtained by the above method has a methylol group produced by a condensation reaction,
Stabilization can be achieved by etherification with alcohol. The amino resin (b) used in the present invention is prepared by a method of reacting 1.0 mol of an amino compound, 1.5 to 8 mol of an aldehyde compound, and 3 to 20 mol of an etherifying alcohol according to a known and commonly used production method. It can be manufactured. In the reaction, a known and commonly used solvent may be used if necessary.

2 amino compounds or aldehyde compounds
When used in combination with at least one species, the ratio is not particularly limited, but if the acid value of the resulting amino resin (b) is too low, the solubility in a water-soluble solvent will be poor, and the carboxyl group or phenol at the time of heat curing will be poor. If the acid value of the resulting amino resin (b) is too high, the colored cured film layer tends to have poor water resistance. Therefore, the acid value of the amino resin (b) is 20 to 250.
It is preferable to adjust the composition so as to be in the range of mgKOH / g.

The amino resin (b) in which a methylol group is etherified can be produced by a known and commonly used method. For example, (1) an amino compound is added to a solution prepared by adding an aldehyde compound to an etherification alcohol, and if necessary, reacted at 50 to 140 ° C. for 20 minutes to 7 hours in the presence of an acidic catalyst to carry out a condensation reaction and an ether. Reaction method at the same time,

(2) An aldehyde compound and an amino compound are reacted in the range of pH 8 to 10 to methylate the amino compound, and then, in the presence of an etherifying alcohol, an alkyl ether is added in the range of pH 2 to 6. How to

(3) At least 1 selected from the group consisting of urea, melamine, benzoguanamine, acetoguanamine, cyclohexanecarboguanamine, phthaloguanamine, steroguanamine and spiroguanamine in a solution prepared by adding an aldehyde compound to an etherification alcohol.
A kind of amino compound is added, and (4,6-diamino-1,3,5-triazin-2-yl) benzoic acid and / or (4,6-diamino-1, 3,5-triazin-2-yl) -phenol added,

(4) The alcohol for etherification is selected from the group consisting of formaldehyde, paraformaldehyde, acetaldehyde, propionaldehyde, butyraldehyde, glyoxal, glyoxylic acid, succine semialdehyde and 2-, 3- or 4-hydroxybenzaldehyde. , At least one aldehyde compound, and then urea, melamine, benzoguanamine, acetoguanamine, cyclohexanecarboguanamine, phthaloguanamine, steroguanamine, spiroguanamine, (4,6-diamino-1,3,5-triazine-2- Yl) benzoic acid, and (4,6-diamino-
1,3,5-triazin-2-yl) -phenol, at least one amino compound is added, and a condensation reaction and an etherification reaction are carried out.

The carboxyl group or the phenolic hydroxyl group contained in the amino resin (b) is completely neutralized or partially neutralized with various volatile bases such as ammonia or organic amine to obtain water, or water-soluble with water. It is also possible to dissolve or disperse in a mixture with a solvent.

The organic amine used for neutralizing the carboxyl group or the phenolic hydroxyl group contained in the amino resin (b) is not particularly limited, but examples thereof include monomethylamine, dimethylamine, monoethylamine, diethylamine and triethylamine. Alkylamines;
N-methylaminoethanol, N, N-dimethylaminoethanol, N, N-diethylaminoethanol, 2-
Hydroxylamines such as amino-2-methylpropanol, diethanolamine or triethanolamine; polyvalent amines such as ethylenediamine or diethylenetriamine. These may be used alone or in combination of two or more.

Examples of the solvent used in the ink composition (a) include aromatic solvents such as toluene, xylene and methoxybenzene; ethyl acetate, butyl acetate, propylene glycol monomethyl ether acetate, propylene glycol monoethyl ether acetate and the like. Acetate-based solvent; Propionate-based solvent such as ethoxyethyl propionate; Alcohol-based solvent such as methanol, ethanol, propanol and ethylene glycol; Ether-based solvent such as butyl cellosolve, propylene glycol monomethyl ether, diethylene glycol ethyl ether and diethylene glycol dimethyl ether; Methyl ethyl ketone, methyl isobutyl ketone,
Ketone solvents such as cyclohexanone; Aliphatic hydrocarbon solvents such as hexane; Nitrogen compound solvents such as N, N-dimethylformamide, γ-butyrolactam, N-methyl-2-pyrrolidone, aniline and pyridine; γ-
Lactone solvents such as butyrolactone; carbamate esters such as a 48:52 mixture of methyl carbamate and ethyl carbamate; water, or a mixture of water and a water-soluble organic solvent. Among these solvents, those having a boiling point in the range of 80 ° C. to 200 ° C. are preferable, and these solvents can be used alone or in combination of two or more kinds.

In the present invention, phthalocyanine (a)
When preparing the ink composition (a) in which is dispersed, a dispersant may be used together. There is no particular limitation on such a dispersant, and a known and commonly used dispersant can be used. Examples of such a dispersant include resin-type dispersants such as surfactants, pigment intermediates, dye intermediates, polyester compounds, polyamide compounds, polyurethane compounds, acrylic compounds and polyethylene compounds. And so on.

Examples of commercially available resin-type dispersants include "Disperbic 130" manufactured by BYK Chemie.
"Disperbic 161", "Disperbic 16
2 "," Disperbic 163 "," Disperbic 170 "," Disperbic 2000 "," Disperbic 2001 "," Efka 46 "," Efka 47 "made by EF Car Chemicals, and" Solspers 32550 made by Zeneca. " , "Solsperth 24000", Ajinomoto Co.'s "Azisper PB811", "Azisper PB"
814 ”and the like.

The compounding amount of the phthalocyanine (a) in the ink composition (a) is preferably in the range of 10 to 70 mass% with respect to the non-volatile content in the ink composition (a). When the dispersant is used in combination, the proportion of the dispersant is preferably in the range of 5 to 50 mass% with respect to the total pigment.

The color filter of the present invention is produced by forming a pixel portion on a transparent substrate using the ink composition (a) by an ink jet recording method and then thermally curing the pixel portion. You can At that time, the amino resin (b) itself is thermally cured. Since the amino resin (b) used in the present invention has a carboxyl group or a phenolic hydroxyl group, there is no need to use a curing accelerator in combination, and the curing accelerator does not remain as an impurity in the colored cured coating. Have.

A compound (c) having a photopolymerizable functional group may be added to the ink composition (a). In this case, a color filter may also be formed by forming a pixel portion on a transparent substrate by an inkjet recording method, then photo-curing the colored film layer of the ink composition (a) in the pixel portion, and then further thermally curing it. Can be manufactured. In that case, it is desirable to use a photopolymerization initiator together in the ink composition (a). The energy ray for photopolymerization is preferably a light ray having a wavelength of 200 to 500 nm.

When the film of the ink composition (a) formed on the pixel portion is photo-cured before being heat-cured, the crystal growth of the pigment due to the heating during the post-baking can be suppressed, and as a result, It is possible to obtain the effect that it is possible to prevent a decrease in transparency and color purity of the colored cured film layer that is obtained.

The compound (c) having a photopolymerizable functional group is a compound having a functional group capable of being photocured by being polymerized or cross-linked by irradiation with ultraviolet rays, visible rays, etc. Radical-polymerizable compounds and cation-polymerizable compounds are mentioned. Specifically, a (meth) acrylic compound, a maleimide compound, etc. are mentioned. Examples of the compound (c) having a photopolymerizable functional group include, for example, trimethylolethane tri (meth) acrylate,
Trimethylolpropane tri (meth) acrylate, trimethylolpropane di (meth) acrylate, neopentyl glycol di (meth) acrylate, pentaerythritol tetra (meth) acrylate, pentaerythritol tri (meth) acrylate, dipentaerythritol hexa (meth) Acrylate, dipentaerythritol penta (meth) acrylate, hexanediol di (meth) acrylate, trimethylolpropane tri (acryloyloxypropyl) ether, tri (acryloyloxyethyl) isocyanurate, tri (acryloyloxyethyl) cyanurate, glycerin tri ( (Meth) acrylic acid esters such as (meth) acrylate; phenol / novolac type epoxy resin, cresol / novolac Epoxy resin, a reaction product of an epoxy resin and (meth) acrylic acid such as bisphenol A type epoxy resin, ethylene glycol, polyethylene glycol, polypropylene glycol, polytetramethylene glycol, polyethoxy diol of bisphenol A,
Polyester polyol, polybutadiene polyol,
Polyols such as polycarbonate polyols and organic polyisocyanates (for example, tolylene diisocyanate, xylylene diisocyanate, isophorone diisocyanate, hexamethylene diisocyanate) and hydroxyl group-containing (meth) acrylates (for example, 2-hydroxyethyl (meth) acrylate, 2-hydroxypropyl (meth) acrylate, 1,4-butanediol mono (meth) acrylate, etc.) and the like can be mentioned.

The maleimide compound used as the compound (c) having a photopolymerizable functional group is preferably a compound in which a maleimide group is bound by an aliphatic group, specifically, N-hexylmaleimide or N, N. 'Alkyl such as 4,9-dioxa-1,12-bismaleimidododecane or an aliphatic maleimide compound having an ether bond in the carbon chain, ethylene glycol bis (maleimide acetate), poly (tetramethylene glycol)
Maleimide carboxylic acid (poly) alkylene glycol esters such as bis (maleimide acetate), tetra (ethylene glycol modified) pentaerythritol tetra (maleimide acetate), carbonate maleimides such as bis (2-maleimidoethyl) carbonate, isophorone bisurethane bis (N -Ethyl maleimide) and other urethane maleimides. Among these, trimethylolpropane tri (meth) acrylate, pentaerythritol tetra (meth) acrylate, dipentaerythritol hexa (meth) acrylate, dipentaerythritol penta (meth) acrylate, N,
N′-4,9-dioxa-1,12-bismaleimidododecane, ethylene glycol bis (maleimide acetate), poly (tetramethylene glycol) bis (maleimide acetate), (ethylene glycol modified) pentaerythritol tetra (maleimide acetate), Polyfunctional (meth) acrylates and polyfunctional maleimides such as bis (2-maleimidoethyl) carbonate and isophoronebisurethane bis (N-ethylmaleimide) have high sensitivity to ultraviolet rays and visible rays, and have high crosslinking density. It is particularly preferable in that it can be obtained.

The compound (c) having a photopolymerizable functional group is
One kind or a combination of two or more kinds may be used, and the use ratio thereof is not particularly limited, but may be based on the total amount of the binder resin containing the amino resin (b) used in the ink composition (a). On the other hand, the range of 25 to 150 mass% is preferable. When it exceeds 150% by mass, the heat resistance aimed at by the present invention decreases, while when it is less than 25% by mass, the physical properties of the colored photocured film of the ink composition (a) by the desired photopolymerization are improved. It is difficult to obtain the effect.

When a photopolymerizable compound is added to the ink composition (a), a photopolymerization initiator may be used in combination, if necessary. As the photopolymerization initiator, a photopolymerization initiator capable of generating a radical by being dissociated by light can be used, and as such a photopolymerization initiator, known and conventional ones are used. Specifically, for example, benzophenone, 4,4 ′
-Benzomethyls such as bismethylaminobenzophenone and Michler's ketone; xanthones such as xanthone and thioxanthone, p-dimethylaminoacetophenone, benzyl-4-dimethylaminobenzoate, 4-
Bis-trichloromethyl-6- (4-ethoxy) phenyl-S-triazine, 2-amylanthraquinone, β-
Examples thereof include chloranthraquinone and biimidazole.

Examples of commercially available photopolymerization initiators include, for example,
"Irgacure-184", "Irgacure-36"
9 "," Darocur-1173 "," Lucirin-TP "
"O", "Kayakyu DETX", "Kayakyu O
"A", "Bicure 10", "Bicure 55",
Examples thereof include "trigonal PI", "Sandley 1000", "deep", "biimidazole" and the like.

A known and commonly used photosensitizer may be used in combination with the photopolymerization initiator. Examples of the photosensitizer include amines, ureas, sulfur-containing compounds, phosphorus-containing compounds,
Examples thereof include chlorine-containing compounds, nitriles and other nitrogen-containing compounds. These may be used alone or in combination of two or more. The use ratio thereof is not particularly limited, but is 0.1 to the compound (c) having a photopolymerizable functional group in the ink composition (a).
The range of 30 mass% is preferable, and the range of 1 to 20 mass% is particularly preferable. If it is less than 0.1% by mass, the sensitivity tends to decrease, and if it exceeds 30% by mass, precipitation of crystals and deterioration of physical properties of the colored cured film tend to occur, which is not preferable.

The viscosity of the ink composition (a) is 50 mPas.
When adjusted to s or less, good ejection properties from the inkjet head can be obtained. In particular, it is preferably 10 mPa · s or less. For this purpose, the amount of solvent is preferably in the range of 1 to 19 parts by mass per 1 part by mass of the nonvolatile content in the ink composition (a).

Since the ink composition (a) thus obtained is a one-pack type, it has excellent storage stability, and since it uses an amino resin having a carboxyl group or a phenolic hydroxyl group, it is used as a solvent. Not only a non-aqueous organic solvent but also water, an aqueous solvent, or a mixed solvent thereof can be used as the solvent. When a color filter is manufactured using the ink composition (a), the amino resin (b) is used in the firing step after pixel formation.
The resulting color filter has excellent heat resistance and solvent resistance, since it is cross-linked and heat-cured.

If necessary, known additives may be added to the ink composition (a) as long as the effects of the present invention are not impaired. Examples of such additives include coupling agents, antioxidants, stabilizers,
Examples include fillers, various leveling agents such as silicone-based, fluorine-based, and acrylic-based, polyvalent carboxylic acids and their anhydrides, and epoxy compounds. In this way, it can be suitably used as an inkjet ink for a color filter.

The coupling agent has a function of chemically binding the inorganic material and the organic material and enhancing the affinity between them. Typical coupling agents include silane compounds, titanium compounds, and aluminum compounds. Among these, γ-glycidoxypropyltrimethoxysilane, β in terms of imparting excellent smoothness, adhesiveness, water resistance and solvent resistance to various transparent substrates.
A silane coupling agent having an epoxy group such as-(3,4-epoxycyclohexyl) ethyltrimethoxysilane is preferable. These coupling agents may be used alone or in combination of two or more.

The amount of the coupling agent used is in the range of 0.1 to 30 parts by mass, preferably 0.5 to 20 parts by mass, per 100 parts by mass of the amino resin (b). When the amount of the coupling agent used is 0.1 parts by mass or less, the smoothness, water resistance and solvent resistance of the colored film layer of the ink composition (a) formed on the transparent substrate for a color filter, and the transparent substrate Adhesiveness is insufficient, and when it exceeds 30 parts by mass, improvement in adhesiveness cannot be expected, and the photocurability of the colored film layer of the ink composition (a) to be formed is lowered.

The polyvalent carboxylic acid and its anhydride are used for the purpose of adjusting the solubility of the amino resin (b) in an aqueous solvent, and the epoxy compound is used as a carboxyl group of the amino resin (b) after photocuring. It is used for the purpose of improving the water resistance of the colored cured film layer of the ink composition (a) by causing a thermal reaction.

Examples of the epoxy compound include phenol / novolak type epoxy resin, cresol / novolak type epoxy resin, bisphenol A type epoxy resin, bisphenol F type epoxy resin, bisphenol A / novolak type epoxy resin, alicyclic epoxy resin, and the like. Examples include various glycols, alkylene oxide-modified epoxy resins, glycidyl group-containing acrylic resins, alicyclic epoxy group-containing acrylic resins, and the like. These may be used alone or in combination of two or more.

Since the phthalocyanine (a) is a green colorant, the ink composition (a) of the present invention is an ink jet ink composition for a green pixel portion of a color filter, but is used for the ink composition (a). If the phthalocyanine (a) is replaced with a known red or blue pigment, an ink jet ink composition for red or blue color filters excellent in heat resistance, chemical resistance and the like in the same manner as the ink composition (a). Can be obtained.

On the transparent substrate, the ink composition (a) prepared as described above was used to form a pattern of the colored film layer on the green pixel portion of the color filter by the ink jet method, and then the composition was heat cured. , Or after photo-curing, further heat-curing, and then through similar steps,
The color filter of the present invention can be manufactured by forming a colored cured film layer of a known inkjet ink composition for a color filter corresponding to each color in the red pixel portion and the blue pixel portion, respectively. The transparent substrate used in the present invention can be used as long as it is a transparent substrate used for a color filter and has heat resistance capable of withstanding thermosetting, and a typical example thereof is a glass substrate.

Examples of the ink jet method used in the present invention include a bubble jet (registered trademark) method using an electrothermal converter as an energy generating element and a piezo jet method using a piezoelectric element.

To form a pixel pattern, first, the ink composition (a) may be discharged from the discharge head onto a predetermined pixel portion on a transparent substrate provided with a black matrix by an inkjet method. The black matrix can be provided on the transparent substrate by a known forming method, that is, a method of forming a metal thin film pattern by a sputtering or vapor deposition method, a method of patterning by a photolithography method using a black resin composition, an inkjet method and the like. . At this time, depending on the properties of the inkjet ink composition, the black matrix may be subjected to a hydrophilic treatment, a hydrophobic treatment or an oil repellent treatment. Further, if necessary, surface treatment of the substrate with an adhesive aid such as the above-mentioned coupling agent is effective as a means for improving the adhesive force between the substrate and the pixel pattern. Further, the substrate may be provided with an ink jet ink receiving layer.

The color filter of the present invention can be manufactured by the following method. That is, after the ink composition (a) is ejected from the ejection head by an inkjet method onto the green pixel portion on the transparent substrate provided with the black matrix to form a colored film layer of the ink composition (a), The coating layer is heat-cured, or light-cured and then heat-cured. Similarly, a colored cured film layer is formed on the red and blue pixel portions using a known inkjet ink composition for color filters corresponding to each color, and then, if necessary, a protective layer on the pixel portion. And post-base if necessary, and then I
A method of forming a transparent conductive electrode such as TO may be used.

As a heat source used for heat curing, for example,
Known heat sources such as hot plates, electric ovens, infrared heating furnaces, etc. may be mentioned. The heating temperature is 150-3
The range of 00 ° C is preferred. If the temperature is lower than 150 ° C., the heat curing is insufficient, so that the strength, solvent resistance, and alkali resistance of the colored cured film layer tend to be inferior, and if the temperature exceeds 300 ° C., the colored cured film layer excessively shrinks in volume, Problems tend to occur in adhesion and accuracy with respect to the substrate.

When the colored film layer is photo-cured before being heat-cured, the light used is preferably ultraviolet light or visible light, and particularly preferably light having a wavelength of 200 to 500 nm.
As these light sources, for example, low-pressure mercury lamp, high-pressure mercury lamp, ultra-high pressure mercury lamp, metal halide lamp, chemical lamp, black light lamp, mercury-xenon lamp, excimer lamp, short arc lamp,
Helium / Cadmium laser, Argon laser,
A known and commonly used light source such as a THG using an Nd-YAG laser or an FHG light laser can be used. The photo-curing condition is affected by the type of light source used and the type and amount of photo-polymerization initiator, and cannot be determined unconditionally, but generally 10
The range of 0 to 3000 J / m ² is preferable. When using both photo-curing and heat-curing, the above-mentioned heat-curing treatment is performed after the above-mentioned photo-curing treatment. The green pixel portion of the color filter of the present invention obtained through the above steps is excellent in transparency, color purity and color density, and also excellent in heat resistance, chemical resistance and light resistance.

[0076]

The present invention will be described in more detail with reference to Examples. In the following, all parts and% are based on mass unless otherwise specified.

<Preparation of Amino Resin Having Carboxyl Group> (Production Example 1) 2- (4,6) containing 12.3 parts of water in a reaction vessel equipped with a thermometer, a reflux condenser and a stirrer.
-Diamino-1,3,5-triazin-2-yl) benzoic acid 131.7 parts, 37% aqueous formaldehyde solution 20
2.8 parts and 222.3 parts of n-butanol were charged and refluxed for 2 hours with stirring, and then, under reduced pressure of 5.33 × 10 ⁴ Pa, it took 3 hours to remove excess formaldehyde together with most of water. Was distilled off.

Next, after distilling off the remaining water and n-butanol, propylene glycol monomethyl ether acetate (hereinafter abbreviated as PGMAc) was added and cooled, and PGMAc was further added to adjust the nonvolatile content to 40%. did. An amino resin having a carboxyl group (b-), in which the acid value of the resin solid content (the number of milligrams of potassium hydroxide required to neutralize the acidic groups present in 1 g of the sample, the same hereinafter) is 94.6 mgKOH / g. 1) was obtained. The polystyrene-equivalent number average molecular weight; Mn was 2150, and the dispersity was Mw / Mn was 5.12.

(Production Example 2) Benzoguanamine 37.4 was placed in a reaction vessel equipped with a thermometer, a reflux condenser, and a stirrer.
Parts, 50% glyoxylic acid aqueous solution 118.4 parts, and n-butanol 88.8 parts were charged and refluxed for 1 hour while stirring, and after 4 hours under a reduced pressure of 5.33 × 10 ⁴ Pa, it was large. Part of the water was distilled off. Then the remaining water and n-
After distilling off butanol, PGMAc was added and cooled,
Further, PGMAc was added to adjust the nonvolatile content to 40%. Acid value of resin solid content is 136mgKOH / g
Amino resin (b-2) having a carboxyl group was obtained. Number average molecular weight in terms of polystyrene; Mn is 162
4, dispersity: Mw / Mn was 1.28.

<Preparation of Amino Resin Having Phenolic Hydroxyl Group> (Production Example 3) 18.7 parts of benzoguanamine and 48.8 parts of p-hydroxybenzaldehyde were placed in a reaction vessel equipped with a thermometer, a reflux condenser and a stirrer. n-butanol 8
8.8 parts were charged and the mixture was stirred at 125 ° C. for 24 hours. Thereafter, n-butanol was distilled off under a reduced pressure of 5.33 × 10 ⁴ Pa, and the obtained solid was washed with a mixed solution of n-hexane / ethyl acetate (2/1) to remove excess p- The hydroxybenzaldehyde was removed. PGMAc was added and cooled, and PGMAc was further added to adjust the nonvolatile content to 40%. Acid value of resin solid content is 85.2 mgK
An OH / g amino resin (b-3) having a phenolic hydroxyl group was obtained. Polystyrene-equivalent number average molecular weight;
Mn was 4000, dispersity; Mw / Mn was 3.26.

(Example 1) A high-speed disperser "TS" manufactured by Igarashi Machinery Co., Ltd., in which zirconia beads having a diameter of 0.5 mm were charged.
C-6H "has a primary particle diameter of 35 to 45 nm and 15 parts of phthalocyanine (a) (zinc halide phthalocyanine) having the following average composition, 4.5 parts of BYK-2001 acrylic dispersant" BYK-2001 ", PGMAc80. 0.5 part was charged and stirred at 2000 rpm for 8 hours to obtain a green pigment dispersion composition (G-1).

<Average composition of halogenated zinc phthalocyanine> In the general formula (1),

Then, 15 parts of "CI Pigment Yellow 150" having a primary particle diameter of 35 to 45 nm was used in place of 15 parts of phthalocyanine (a), except that the above phthalocyanine (a) dispersion composition (G- A yellow pigment dispersion composition (Y-1) was obtained in the same manner as in the preparation of 1).

53 parts of the green pigment dispersion composition (G-1) and 47 parts of the yellow pigment composition (Y-1) were mixed to obtain a pigment dispersion composition (1) for a color filter. 100 parts of the pigment dispersion composition for the color filter, amino resin (b-1)
After mixing 31.3 parts and 17.1 parts of PGMAc, it filtered using the filter with a pore size of 1.0 micrometer, and the inkjet ink composition (a-1) for thermosetting color filters of this invention was obtained.

Example 2 100 parts of the pigment dispersion composition for a color filter (1) obtained in Example 1, amino resin (b)
-1) 31.3 parts, dipentaerythritol hexaacrylate (hereinafter abbreviated as DPHA) 12.5 parts,
And Ciba Specialty Chemicals photopolymerization initiator "Irgacure # 369" 0.3 part, PGMAc1
After mixing 7.1 parts, the mixture was filtered using a filter having a pore size of 1.0 μm to obtain an inkjet ink composition (a-2) for a color filter.

(Example 3) In place of 15 parts of phthalocyanine (a) (zinc halide phthalocyanine) in Example 1, 15 parts of phthalocyanine (a) (nickel phthalocyanine halide) having the following average composition was used, except that In the same manner as in Example 1, the green pigment dispersion composition (G-
2) was obtained.

<Average composition of halogenated nickel phthalocyanine> In the general formula (1),

45 parts of the green pigment composition (G-2) and 55 parts of the yellow pigment composition (Y-1) were mixed to obtain a pigment dispersion composition (3) for a color filter. Next, 100 parts of the pigment dispersion composition for a color filter (3), 31.3 parts of the amino resin (b-2), 12.5 parts of DPHA, and 0.3 part of "Irgacure # 369", PGMAc1.
After mixing 7.1 parts, the mixture was filtered using a filter having a pore size of 1.0 μm to obtain an inkjet ink composition (a-3) for a color filter.

(Example 4) Instead of 31.3 parts of the amino resin (b-2) in Example 3, the amino resin (b-
3) An inkjet ink composition for a color filter (a-4) was obtained in the same manner as in Example 3 except that 31.3 parts were used.

Comparative Example 1 The same procedure as in Example 1 was repeated except that 15 parts of halogenated copper phthalocyanine having the following average composition was used in place of 15 parts of phthalocyanine (a) (zinc halide phthalocyanine) in Example 1. To obtain a green pigment dispersion composition (GH-1).

[0091] <Average composition of copper halide phthalocyanine>       Central metal: Cu       Ligand: None       Substituents: 13 bromine atoms, 2 chlorine atoms               Number of hydrogen atoms 1

Then, a green pigment dispersion composition (GH-1)
60 parts, 40 parts of yellow pigment dispersion composition (Y-1), acrylic-based alkali-soluble binder resin "EXEDIC LC-295" (PGMAc solution, nonvolatile content: 40%, acid value of the solution) manufactured by Dainippon Ink and Chemicals, Inc. : 33 mgKOH /
g) 31.3 parts of DPHA, 12.5 parts of DPHA, and 0.3 parts of Irgacure # 369, 17.1 parts of PGMAc, and then filtered using a filter having a pore size of 1.0 μm to prepare an inkjet ink composition for a color filter. The product (h-1) was obtained.

Comparative Example 2 60 parts of the green pigment dispersion composition (GH-1) obtained in Comparative Example 1 and 40 parts of the yellow pigment dispersion composition (Y-1) obtained in Example 1 were used as a binder resin. After mixing 31.3 parts of melamine resin “Super Beckamine J-820-60” (n-butanol / xylene solution) manufactured by Nippon Ink Chemical Co., Ltd. and 17.1 parts of PGMAc, a filter having a pore diameter of 1.0 μm was used. An inkjet ink composition for a color filter (h-
2) was obtained.

The above Examples 1 to 4 and Comparative Examples 1 and 2
The following tests were carried out on the inkjet ink composition for a color filter obtained in 1. The results and evaluation are shown in Table 1 and FIG. However, the ink jet ink composition for a color filter (h-2) obtained in Comparative Example 2 had poor dispersibility of the green pigment, and when the ink was ejected onto the glass substrate using the ink jet head, the head clogging occurred. Therefore, the following evaluation according to the items of the performance test was not performed.

<Color Density Test of Cured Film Layer of Inkjet Ink Composition for Color Filters> Inkjet ink composition for color filters after post-baking using a piezo jet type inkjet head manufactured by Saar Co. on a transparent glass substrate. The x and y values in the CIE color system chromaticity of the cured film layer are x = 0.260, y =
The inkjet ink compositions for color filters obtained in Examples and Comparative Examples were solid-printed so as to be 0.630, and then prebaked at 60 ° C. for 5 minutes to form an inkjet ink composition coating layer for color filters. . Then, about the ink-jet ink composition coating layer for color filters of Examples 2 to 4 and Comparative Example 1 in which DPHA was blended, a high pressure mercury lamp was used to obtain 0.1 J /
After irradiating cm ² of light to photopolymerize DPHA to photocure it, post-baking at 250 ° C. for 30 minutes to thermally cure the amino resin contained in the film to prepare a sample for color density test. did.

For Example 1 and Comparative Example 2 in which DPHA was not blended, after solid-printing the ink jet ink composition for a color filter on a transparent glass substrate using a piezo jet type ink jet head manufactured by Saar, 110 Preliminary drying was performed at 10 ° C. for 10 minutes to form an inkjet ink composition film layer for a color filter.
The coating layer is then placed in an oven at 200 ° C. for 30 minutes,
Further, post-baking was performed at 250 ° C. for 30 minutes to thermally cure the amino resin contained in the film to prepare a sample for color density test.

The CIE color development chromaticity of the ink-jet ink composition cured film layer was measured using an Olympus microspectrophotometer "OSP-SP-200".
The film thickness of the cured film layer of the inkjet ink composition after post-baking is measured by Nippon Vacuum Engineering Co., Ltd.
It was measured using "KTAK3". x = 0.260, y
It was evaluated that the thinner the film thickness was 0.630, the higher the color density was. The results are shown in Table 1.

<Transparency Test of Cured Film Layer of Inkjet Ink Composition for Color Filter> Regarding the cured film layer of inkjet ink composition for color filter of the above sample for color density test, a microspectrophotometer "OSP-SP" was used.
-200 "was used to measure the Y value in the chromaticity of the CIE color system. The larger the Y value, the higher the transparency. The results are shown in Table 1.

<Color Purity Test of Cured Film Layer of Inkjet Ink Composition for Color Filter> Using each inkjet ink composition for color filter obtained in Examples and Comparative Examples, a piezo jet type inkjet head manufactured by Saar Co., Ltd. was used. A green pixel pattern was formed on the glass substrate. In the subsequent steps, the thickness of the cured film layer of the inkjet ink composition after post-baking was 2.0 and 2.
5, 3.0 μm color purity test samples were prepared. Regarding the ink-jet ink composition cured film layer of the sample for color purity test, the microspectrophotometer "OSP-SP-200"
Was used to measure the y value in the CIE color development system. It was evaluated that the higher the y value, the higher the color purity. The results are shown in Fig. 1.

<Heat resistance test of cured film layer of inkjet ink composition for color filter> Regarding the cured film layer of inkjet ink composition for color filter of the above-mentioned sample for color density test, a microspectrophotometer "OSP-SP" was used.
-200 "was used to measure the Y value in the CIE color development system chromaticity, and the value was defined as Y1. Then, the cured film layer was further heated at 280 ° C. for 30 minutes, and then the Y value of the cured film layer was measured using the above apparatus, and the value was defined as Y2. The smaller the difference ΔY between Y1 and Y2 is, the higher the heat resistance of the cured film layer is evaluated, and the one less than 0.5 is ◯,
Those having a value of 0.5 or more were represented by x. The results are shown in Table 1.

[0101]

[Table 1]

From the results shown in Table 1, the green pixel portion of the color filter having the ink-jet ink composition cured coating layer for a color filter containing the phthalocyanine (a) and the amino resin (b) used in the present invention had a conventional type. It is clear that the transparency and the color density are excellent as compared with the case where the halogenated copper phthalocyanine and the yellow pigment are used.

Further, from the results shown in FIG. 1, the green pixel portion of the color filter having the ink-jet ink composition cured coating layer for a color filter containing the phthalocyanine (a) and the amino resin (b) used in the present invention was It is clear that the color purity is excellent as compared with the case of using the conventional halogenated copper phthalocyanine and the yellow pigment.

Further, from the results shown in Table 1, the green pixel portion of the color filter having the ink-jet ink composition cured coating layer for a color filter containing the phthalocyanine (a) and the amino resin (b) used in the present invention was It is apparent that the heat resistance is excellent as compared with the case where an acrylic resin is used instead of the amino resin (b).

[0105]

The ink jet ink composition for a color filter of the present invention comprises a) a halogenated phthalocyanine represented by the general formula (1) and (b) an amino resin having a carboxyl group or a phenolic hydroxyl group. Therefore, the green pixel portion of the color filter having the ink-jet ink composition cured film layer formed on the substrate by the inkjet method using this is excellent in color density, transparency, color purity and heat resistance test. . Further, by containing a compound having a photopolymerizable functional group in the inkjet ink composition for a color filter of the present invention, it is possible to provide a highly practical color filter that uses both photocuring and heat curing.

[Brief description of drawings]

FIG. 1 is a diagram showing a relationship between a film thickness of a colored cured film layer of an inkjet ink composition for a color filter and ay value in a CIE color development system.

─────────────────────────────────────────────────── ─── Continuation of the front page (51) Int.Cl. ⁷ Identification code FI theme code (reference) G02F 1/1335 505 B41J 3/04 101Z (72) Inventor Yoshiro Yamaguchi 3-34 Kishibe Minami Suita City, Osaka Prefecture 2 (72) Inventor Hiroshi Katsube 3-14-17 Nakazato, Kita-ku, Tokyo F-term (reference) 2C056 FB01 2H048 BA02 BA11 BA64 BB02 BB12 BB42 BB46 2H086 BA05 BA55 BA59 2H091 FA02 FB02 FB06 FC01 FC22 FC23 LA03 LA04 LA12 LA16 LA30 4 AE03 BC60 BC72 BC73 BE27 EA21 EA33 EA35 EA37 EA39 EA40 GA24

Claims (9)

[Claims] 1. An inkjet ink for a color filter comprising (a) a halogenated phthalocyanine represented by the following general formula (1) and (b) an amino resin having a carboxyl group or a phenolic hydroxyl group. Composition. [Chemical 1] (1) (where M is Al, Si, Sc, Ti, V, F
e, Co, Ni, Zn, Ga, Ge, Y, Zr, Nb,
It represents one kind of metal selected from In, Sn and Pb or two hydrogen atoms. X _{1 to} X ₁₆ are hydrogen, fluorine, chlorine,
It represents an atom selected from bromine and iodine, and the total sum of halogen atoms is an integer of 8 to 16. Y represents fluorine, chlorine, bromine, iodine, oxygen, or a hydroxyl group, and m is 0.
Represents an integer of 2; ) 2. The (b) amino resin having a carboxyl group or a phenolic hydroxyl group is (4,6-diamino-
An amino resin obtained by condensing 1,3,5-triazin-2-yl) benzoic acid with at least one aldehyde compound selected from the group consisting of formaldehyde, glyoxylic acid, succinosemialdehyde and hydroxybenzaldehyde. Item 2. The inkjet ink composition for a color filter according to Item 1. 3. The (b) amino resin having a carboxyl group or a phenolic hydroxyl group is selected from the group consisting of melamine, benzoguanamine and (4,6-diamino-1,3,5-triazin-2-yl) benzoic acid. The inkjet for a color filter according to claim 1, which is an amino resin obtained by condensing at least one triazine-based compound with at least one aldehyde compound selected from the group consisting of glyoxylic acid, succinemialdehyde, and hydroxybenzaldehyde. Ink composition. 4. The inkjet ink composition for a color filter according to claim 1, which comprises (c) a compound having a photopolymerizable functional group. 5. A color filter having a colored cured film layer of the inkjet ink composition for a color filter according to claim 1 on a transparent substrate. 6. A color filter comprising a colored cured film layer of the inkjet ink composition for a color filter according to claim 4 on a transparent substrate. 7. A transparent substrate on which (a) the general formula (1)
A colored film of an inkjet ink composition for a color filter by an inkjet recording method using an inkjet ink composition for a color filter containing a halogenated phthalocyanine represented by the formula (b) and an amino resin having a carboxyl group or a phenolic hydroxyl group (b). A method for producing a color filter, which comprises curing the colored film layer after forming the layer. 8. The method for producing a color filter according to claim 7, wherein the inkjet ink composition for a color filter is a composition containing (c) a compound having a photopolymerizable functional group. 9. The method for producing a color filter according to claim 8, wherein after the colored film layer of the inkjet ink composition for a color filter is photo-cured, it is further thermally cured.