JP5572986B2 - Colorant for color filter, coloring composition for color filter using the same, and color filter - Google Patents

Description

  The present invention relates to a colorant for a color filter, a colorant composition for a color filter using the same, and a color filter having a segment containing the same.

  A color filter used in a liquid crystal display device is a structure in which segments of three colors of red, green, and blue are arranged in a vertical and horizontal direction on a transparent substrate such as glass. Generally, in order to form a green segment, A green pigment is used as a colorant.

  Color filter compositions using various phthalocyanine compounds as green pigments have been proposed.

  Patent Document 1 proposes a color filter composition using a halogenated phthalocyanine compound substituted with at least four halogen atoms as a green colorant.

  Patent Document 2 discloses a chlorinated copper phthalocyanine pigment C.I. I. Pigment Green 7 (hereinafter abbreviated as PG7) and / or brominated phthalocyanine pigment C.I. I. A composition for a color filter having a long maximum absorption wavelength has been proposed by using a pigment 36 (hereinafter abbreviated as PG36).

  Patent Document 3 discloses a color filter using, as a green pigment, one or more phthalocyanine compounds selected from the group consisting of a phthalocyanine compound having no central metal and a phthalocyanine compound having a central metal other than copper. Compositions have been proposed.

  In Patent Document 4, as a green pigment, a halogenated copper phthalocyanine pigment and a central metal are selected from the group consisting of Mg, Al, Si, Ti, V, Mn, Fe, Co, Ni, Zn, Ge, and Sn. There has been proposed a color filter composition comprising a green colorant composed of at least one halogenated dissimilar metal phthalocyanine pigment.

  Patent Document 5 proposes a composition for a color filter that contains 35 to 95 mol% of a halogenated copper phthalocyanine having 14 or more bromine atoms in one molecule as a green pigment.

  In Patent Document 6, in a color filter having red, green, and blue pixel portions on a transparent substrate, the green pixel portion has 8 to 16 halogen atoms per phthalocyanine molecule in the benzene ring of the phthalocyanine molecule. There has been proposed a color filter containing a bonded metal halide phthalocyanine pigment and having a maximum transmittance at 520 to 590 nm in a spectral transmission spectrum in the entire visible light range.

  Patent Document 7 discloses an aluminum phthalocyanine dimer via siloxane that is useful for an electrophotographic developer and a photoelectrophoretic image forming method.

  Both are materials for creating high-lightness color filters and high-lightness color filters, but in recent years, the demand for high-lightness has become even higher, and various hues have been demanded. The green colorant and the composition using it are insufficient.

JP 2002-131521 A JP 2002-162515 A JP 2003-161821 A JP 2002-250812 A JP 2001-342374 A JP 2003-161827 A Japanese Examined Patent Publication No. 2-45661

  An object of the present invention is to provide a color filter colorant having high brightness, a color filter color composition using the same, and a color filter having a segment containing the same.

The problem is that the siloxyaluminum phthalocyanine compound represented by the general formula (1) is refined by solvent salt milling, dry milling, or acid pasting, and a black angle 2θ (± 0) in an X-ray diffraction pattern by CuKα rays. .2) = 6.1 °, 8.0 °, 9.5 °, 10.7 °, 12.6 °, 13.6 °, 14.1 °, 14.8 °, 17.2 °, 18 Siloxyaluminum having peaks at 3 °, 18.8 °, 19.2 °, 20.4 °, 22.1 °, 23.8 °, 24.6 °, 26.3 °, and 27.8 ° Solvent salt milling, dry milling, or acid pasty of a phthalocyanine pigment and / or a siloxyaluminum phthalocyanine compound represented by the following general formula (1) and hydroxyaluminum phthalocyanine In the X-ray diffraction pattern by CuKα ray, the black angle 2θ (± 0.2) = 6.0 °, 7.5 °, 8.4 °, 9.8 °, 13.1 °, 15.1 °, is solved by 16.3 °, 18.5 °, 20.2 ° , 21.3 °, 22.8 °, and 26.8 shown to color filter colorant peaks at ° .

  That is, the present invention relates to a color filter colorant comprising a siloxyaluminum phthalocyanine compound.

Further, according to the present invention , the X-ray diffraction pattern by CuKα ray has a black angle 2θ (± 0.2) = 6.0 °, 7.5 °, 8.4 °, 9.8 °, 13.1 °. , 15.1 °, 16.3 °, 18.5 °, 20.2 °, 21.3 °, 22.8 °, and 26.8 °, and the above color filter colorant .

Further, in the present invention, the X-ray diffraction pattern of the siloxyaluminum phthalocyanine pigment by CuKα ray has a black angle 2θ (± 0.2) = 6.1 °, 8.0 °, 9.5 °, 10.7 °, 12.6 °, 13.6 °, 14.1 °, 14.8 °, 17.2 °, 18.3 °, 18.8 °, 19.2 °, 20.4 °, 22.1 °, It is related with the said color filter colorant which has a peak in 23.8 degrees, 24.6 degrees, 26.3 degrees, and 27.8 degrees.

  The present invention also relates to the color filter colorant described above, further comprising a yellow pigment.

  Moreover, this invention relates to the coloring composition for color filters characterized by containing the said coloring agent for color filters, and resin and / or the precursor of resin.

  Moreover, this invention relates to the color filter characterized by having the segment which uses the said coloring composition for color filters.

  By using the color filter colorant of the present invention and the color filter green composition using the same for the segment of the color filter, a color filter with high brightness can be exhibited.

It is a figure which shows the X-ray-diffraction pattern by the CuK alpha ray of the siloxy aluminum phthalocyanine pigment (colorant 1) used for the colorant for color filters of this invention. It is a figure which shows the X-ray-diffraction pattern by the CuK (alpha) ray of the siloxy aluminum phthalocyanine pigment (colorant 2) used for the colorant for color filters of this invention.

  First, the color filter colorant of the present invention, the color filter color composition using the same, and various components of the color filter having a segment containing the same will be described.

  In the present application, when expressed as “(meth) acryloyl”, “(meth) acrylic acid”, “(meth) acrylate”, and “(meth) acryloyloxy”, unless otherwise specified, It is intended to represent “acryloyl and / or methacryloyl”, “acrylic acid and / or methacrylic acid”, “acrylate and / or methacrylate”, and “acryloyloxy and / or methacryloyloxy”.

The siloxyaluminum phthalocyanine compound of the present invention can be represented by the following general formula (1).
General formula (1):

In General Formula (1), R ¹ , R ² , and R ³ are each independently an alkyl group having 1 to 18 carbon atoms or an aromatic group having 4 or less rings. When the number of carbon atoms in the alkyl group exceeds 18 or the number of aromatic rings exceeds 4, the molecular weight increases and the extinction coefficient per unit weight decreases, so the pigment concentration in the coloring composition must be increased. It is not obtained and is not preferable.

In the general formula (1), the alkyl groups of R ¹ , R ² , and R ³ may be linear or branched or cyclic, and the total number of heteroatoms is 3 or less. , May have a functional group. For example, methyl, ethyl, propyl, butyl, hexyl, octyl, decyl, dodecyl, octadecyl, isopropyl, isobutyl, sec-butyl, tert-butyl, 1-ethylpentyl Group, cyclopentyl group, cyclohexyl group, trifluoromethyl group, 2-ethylhexyl group, phenacyl group, 1-naphthoylmethyl group, 2-naphthoylmethyl group, 4-methylsulfanylphenacyl group, 4-phenylsulfanylphenacyl group 4-dimethylaminophenacyl group, 4-cyanophenacyl group 4-methylphenacyl group, 2-methylphenacyl group, 3-fluorophenacyl group, 3-trifluoromethylphenacyl group, and 3-nitrophenacyl group Etc.

In the general formula (1), the aromatic groups of R ¹ , R ² , and R ³ may contain a hetero atom in the aromatic ring, and each aromatic ring is functional in the range of 2 or less hetero atoms. It may have a group. Illustrative examples include phenyl, biphenyl, 1-naphthyl, 2-naphthyl, 9-anthryl, 9-phenanthryl, 1-pyrenyl, 5-naphthacenyl, 1-indenyl, 2-azurenyl, 9 -Fluorenyl group, terphenyl group, quarterphenyl group, o-, m-, and p-tolyl group, xylyl group, o-, m-, and p-cumenyl group, mesityl group, pentarenyl group, binaphthalenyl group, turnaphthalenyl group , Quarternaphthalenyl group, heptalenyl group, biphenylenyl group, indacenyl group, fluoranthenyl group, acenaphthylenyl group, aceanthrylenyl group, phenalenyl group, fluorenyl group, anthryl group, bianthracenyl group, teranthracenyl group, quarteranthracene Nyl group, anthraquinolyl group, phenanthri Group, triphenylenyl group, a pyrenyl group, naphthacenyl group, pleiadenyl group, picenyl group, a perylenyl group, tetraphenylenyl les group, and coronenyl group and the like.

In general formula (1), Y and Z are independently of each other a hydrogen atom, an alkyl group which may have a substituent, an aryl group which may have a substituent, a cyano group, a nitro group, A substituent represented by a group, —OR ⁴ , —COR ⁴ , —COOR ⁴ , or —NR ⁴ R ⁵ .

However, R ⁴ and R ⁵ each independently represent a hydrogen atom or an alkyl group which may have a substituent. Alternatively, R ⁴ and R ⁵ may be combined to form a heterocycle containing further nitrogen, oxygen or sulfur atoms.

In general formula (1), the alkyl group which may have a substituent of Y, Z, R ⁴ and R ⁵ is preferably an alkyl group having 1 to 30 carbon atoms, such as a methyl group or an ethyl group. Propyl group, butyl group, hexyl group, octyl group, decyl group, dodecyl group, octadecyl group, isopropyl group, isobutyl group, sec-butyl group, tert-butyl group, 1-ethylpentyl group, cyclopentyl group, cyclohexyl group, Trifluoromethyl group, 2-ethylhexyl group, phenacyl group, 1-naphthoylmethyl group, 2-naphthoylmethyl group, 4-methylsulfanylphenacyl group, 4-phenylsulfanylphenacyl group, 4-dimethylaminophenacyl group 4-cyanophenacyl group, 4-methylphenacyl group, 2-methylphenacyl group, 3-fluorophenacyl group, 3-triphenyl Le Oro methyl phenacyl group, and 3-Nitorofenashiru group.

  In the general formula (1), the aryl group which may have a substituent of Y or Z is preferably an aryl group having 6 to 30 carbon atoms, such as a phenyl group, a biphenyl group, a 1-naphthyl group, 2 -Naphthyl group, 9-anthryl group, 9-phenanthryl group, 1-pyrenyl group, 5-naphthacenyl group, 1-indenyl group, 2-azurenyl group, 9-fluorenyl group, terphenyl group, quarterphenyl group, o-, m- and p-tolyl groups, xylyl groups, o-, m- and p-cumenyl groups, mesityl groups, pentarenyl groups, binaphthalenyl groups, turnaphthalenyl groups, quarternaphthalenyl groups, heptaenyl groups, biphenylenyl groups, indasenyl groups Fluoranthenyl group, acenaphthylenyl group, aceanthrylenyl group, phenalenyl group, fluorenyl group, anthryl group, Anthracenyl group, teranthracenyl group, quarter anthracenyl group, anthraquinolyl group, phenanthryl group, triphenylenyl group, pyrenyl group, chrysenyl group, naphthacenyl group, preadenenyl group, picenyl group, perylenyl group, pentaphenyl group, pentacenyl group, Examples thereof include a tetraphenylenyl group, a hexaphenyl group, a hexacenyl group, a ruvicenyl group, a coronenyl group, a trinaphthylenyl group, a heptaphenyl group, a heptacenyl group, a pyranthrenyl group, and an ovalenyl group.

  In general formula (1), m is an integer of 0 to 16, n is an integer of 0 to 16, and m + n is an integer of 0 to 16.

  As the yellow pigment used in the present invention, various commercially available organic or inorganic pigments can be used. Examples of organic pigments include azo, anthanthrone, anthrapyrimidine, anthraquinone, isoindolinone, isoindoline, indanthrone, quinacridone, quinophthalone, dioxazine, diketopyrrolopyrrole, Examples include thiazine indigo, thioindigo, pyranthrone, flavanthrone, perinone, perylene, and benzimidazolone.

  More specifically, C.I. I. Pigment Yellow 1, 2, 3, 4, 5, 6, 10, 12, 13, 14, 15, 16, 17, 18, 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, 93, 94, 95, 97, 98, 100, 101, 104 106, 108, 109, 110, 113, 114, 115, 116, 117, 118, 119, 120, 123, 126, 127, 128, 129, 138, 139, 147, 150, 151, 152, 153, 154 155, 156, 161, 162, 164, 166, 167, 168, 169, 170, 171, 172, 173, 174, 175, 176, 177, 179, 180 181,182,185,187,188,193,194,199,198,213, and it can be used yellow pigment 214, and the like. When the wavelength is scanned from 400 nm to 700 nm and the transmittance is measured, a yellow pigment having a wavelength of 450 nm to 480 nm at which the transmittance starts to increase rapidly is preferable. I. Pigment Yellow 138 (hereinafter abbreviated as PY138), and C.I. I. Pigment Yellow1 150 (hereinafter abbreviated as PY150) is preferable.

  Organic dyes include nitro, azo, naphthaleneazo, heterocyclic azo, stilbene, carbonium, xanthene, quinoline, methine polymethine, azomethine, thiazole, quinoneimine, anthraquinone, indoid And phthalocyanine series.

  Examples of inorganic pigments include chrome lead and cadmium yellow. These pigments may be used in combination.

  These may be used alone or in combination of two or more pigments.

  In addition, for the purpose of adjusting the hue, a green pigment other than the siloxyaluminum phthalocyanine compound or a pigment other than the yellow pigment can be added. Examples of green pigments other than siloxyaluminum phthalocyanine compounds include C.I. I. And green pigments such as Pigment Green 7, 10, 36, 37, and 58.

In particular, the present invention can achieve a halogen-free material by using an organic pigment and an inorganic pigment which do not contain a halogen as a yellow pigment. In particular, C.I. I. Pigment Yellow 1 150 is preferred.

The following halogen-free materials will be described.

  In the past, halogen-based flame retardants have been used in many electrical products and parts as a fire-protection measure. However, in recent years, in the electronic parts industry, halogens have been used in the electronic parts industry in order to consider environmental issues such as dioxin problems and prevention of ozone layer destruction. The development of non-halogenated materials is spreading due to the development of alternative materials called free. Halogen-based chemicals have no problem with normal use, but when incinerated inappropriately, dioxins are generated due to oxidation of compounds, and ozone-depleting substances such as CFCs are generated.

Halogen-free means that no halogen atom or halogen compound such as chlorine or bromine is contained, or the content is extremely small. The Japan Electronic Circuits Association defines the halogen-free printed wiring board copper-clad laminate as chlorine (Cl) and bromine (Br) content of 0.09 wt% (900 ppm) or less, and the total content is It is defined as 0.15 wt% (1500 ppm).

The coloring composition for the color filter constituting the color filter and the coloring agent for the color filter are no exception, and it is desired to use a halogen-free material containing no halogen atoms such as chlorine and bromine. This can be achieved by using an agent.

  These organic pigments can be used as a colorant for a green color filter by refining pigment particles by a method such as solvent salt milling, dry milling, or acid pasting, if necessary.

  For example, when the organic pigment is refined by solvent salt milling, a mixture of the organic pigment, the water-soluble inorganic salt and the water-soluble solvent is strongly kneaded using a kneader such as a kneader. Next, the kneaded mixture is poured into water and stirred with various stirrers to form a slurry. The inorganic salt and the solvent are removed by filtering this. Through the above steps, a refined organic pigment can be obtained. In this pigment refinement method, the pigment may be either a single pigment or a mixture of two or more.

  Sodium chloride, potassium chloride, etc. can be used as a water-soluble inorganic salt in said refinement | miniaturization process. These inorganic salts are used in the range of 1 to 30 times the weight of the organic pigment. When the inorganic salt to be used is small, sufficient refinement is not performed, and when there is a large amount of inorganic salt, labor is required to remove the inorganic salt, and the processing efficiency is lowered, which is not preferable in terms of productivity.

  As the water-soluble solvent, it is preferable to use a solvent having a boiling point in the range of 120 to 250 ° C. from the viewpoint of safety. Examples of solvents having such properties include 2- (methoxymethoxy) ethanol, 2-butoxyethanol, 2- (isopentyloxy) ethanol, 2- (hexyloxy) ethanol, ethylene glycol, diethylene glycol, diethylene glycol monomethyl ether , Diethylene glycol monoethyl ether, diethylene glycol monobutyl ether, triethylene glycol, triethylene glycol monomethyl ether, polyethylene glycol, 1-methoxy-2-propanol, 1-ethoxy-2-propanol, dipropylene glycol, dipropylene glycol monomethyl ether, and Examples include dipropylene glycol monoethyl ether.

  The coloring composition for a color filter of the present invention contains a resin and / or a resin precursor as a colorant carrier. Depending on the formation method of the color filter segment and the curing method, the type of the resin and / or resin precursor and the weight ratio of the resin to the resin precursor are different.

  The resin and / or resin precursor used in the present invention is used in a total amount of 30 to 700 parts by weight, preferably 60 to 450 parts by weight, based on 100 parts by weight of the colorant in the coloring composition. it can. When the amount is less than 20 parts by weight, a strong color filter film is not formed. When the amount is more than 700 parts by weight, the pigment concentration decreases and color characteristics cannot be expressed.

  Examples of the resin used in the present invention include thermoplastic resins, thermosetting resins, and photosensitive resins.

  Examples of the thermoplastic resin include butyral resin, styrene-maleic acid copolymer, chlorinated polyethylene, chlorinated polypropylene, polyvinyl chloride, vinyl chloride-vinyl acetate copolymer, polyvinyl acetate, polyurethane resin, and polyester resin. Examples include resins, acrylic resins, alkyd resins, polystyrene, polyamide resins, rubber resins, cyclized rubber resins, celluloses, polyethylene, polybutadiene, petroleum resins, and polyimide resins.

  Examples of the thermosetting resin include epoxy resin, benzoguanamine resin, rosin-modified maleic acid resin, rosin-modified fumaric acid resin, melamine resin, urea resin, and phenol resin.

  As the photosensitive resin, for example, a linear polymer having a reactive substituent such as a hydroxyl group, a carboxyl group, an epoxy group, or an amino group has a reactivity such as an isocyanate group, an aldehyde group, an epoxy group, or a carboxyl group. A resin in which a photo-crosslinkable group such as a (meth) acryloyl group or a styryl group is introduced into the linear polymer by reacting a substituted (meth) acrylic compound or cinnamic acid, and styrene-maleic anhydride Resins obtained by half-esterifying a linear polymer containing an acid anhydride such as a copolymer or an α-olefin-maleic anhydride copolymer with a (meth) acrylic compound having a hydroxyl group such as hydroxyalkyl (meth) acrylate Can be mentioned.

  These resins and / or resin precursors can be used in combination as necessary, and differ depending on the patterning method (printing method, ink jet method, photolithography method, etc.) for forming the segment of the color filter.

  In the colored composition of the present invention, the colorant must be uniformly dispersed in the resin and / or resin precursor without agglomeration over a long period of time. In addition, when the coloring composition of the present invention is used as a coating liquid depending on the patterning method of the color filter segment, a coloring agent (in some cases, a resin and / or a resin precursor) is contained in the solvent. It must be uniformly dispersed without agglomeration over a long period of time.

  As a method of dispersing the colorant of the present invention in a resin and / or resin precursor, or a method of dispersing in a solvent, there may be a case where a sufficient dispersion effect can be obtained just by mixing. The method of mechanically mixing using various grinders, such as a mixer, a homomixer, a kneader, a roll mill, an attritor, and a sand mill, is preferable. As in the present invention, when a plurality of dyes such as a siloxyaluminum phthalocyanine compound, a yellow dye, and a dye derivative as described below are co-dispersed in a solvent, they may be mixed separately in powder form. Further, after preparing a suspension or solution of a solvent, they may be mixed and dispersed, or a dispersion can be obtained by mixing each of them after dispersion.

  In addition, when the coloring composition of the present invention is used as a coating liquid for ink or the like, a mixture of the coloring agent of the present invention, a resin and / or a resin precursor, and a solvent is dispersed and adjusted with various dispersers. can do. In that case, you may disperse | distribute after adding a pigment dispersant, a dispersion aid, and various additives.

  In the preparation, the pigment and the pigment dispersant may be added as a pigment composition obtained by mixing in advance, or may be dispersed after being added separately. There is no particular limitation on the order of addition and the method of adding each raw material.

  The organic solvent used when using it for the coloring composition of this invention as coating liquid, such as ink, is not specifically limited. Any of those generally used as a solvent can be used.

As an organic solvent used in the coloring composition of the present invention, for example,
aliphatic hydrocarbon solvents such as n-hexane, cyclohexane, methylcyclohexane, ethylcyclohexane, n-heptane;
Aromatic hydrocarbon solvents such as toluene, m-xylene, o-xylene, m-diethylbenzene, o-diethylbenzene, p-diethylbenzene, n-butylbenzene, isobutylbenzene, sec-butylbenzene, and tert-butylbenzene;
Acetone, methyl ethyl ketone, methyl isobutyl ketone, 2-heptanone, 4-heptanone, diisobutyl ketone, diacetone alcohol, 3,5,5-trimethyl-2-cyclohexen-1-one (also known as isophorone), 3,3,5-trimethyl Ketone solvents such as cyclohexanone and cyclohexanone;
Ethyl acetate, propyl acetate, isopropyl acetate, n-butyl acetate, isobutyl acetate, n-amyl acetate, isoamyl acetate, ethyl lactate, propyl lactate, butyl lactate, dibasic acid ester, ethyl 3-ethoxypropionate, 3-methoxy- Ester solvents such as 3-methylbutyl acetate, 3-methoxybutyl acetate, tetrahydrofurfuryl acetate, and cyclohexyl acetate;
n-butyl alcohol, isobutyl alcohol, n-amyl alcohol, isoamyl alcohol, benzyl alcohol, cyclohexanol, methylcyclohexanol,
3-methoxybutanol, 3-methoxy-3-methyl-1-butanol, diacetone alcohol,
Ethylene glycol, propylene glycol, 1,3-butanediol (also known as 1,3-butanediol), tetramethylene glycol (also known as 1,4-butanediol), 2-methyl-1,3-propanediol, 3-methyl- 1,3-butylene glycol, hexamethylenediol (also known as 1,6-hexanediol),
Ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, ethylene glycol mono n-propyl ether, ethylene glycol monoisopropyl ether, ethylene glycol mono n-butyl ether, ethylene glycol monotertiary butyl ether, ethylene glycol mono n-hexyl ether,
Diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, diethylene glycol mono n-propyl ether, diethylene glycol monoisopropyl ether, diethylene glycol mono n-butyl ether, diethylene glycol monotertiary butyl ether, diethylene glycol mono n-hexyl ether,
Propylene glycol monomethyl ether, propylene glycol monoethyl ether, propylene glycol mono n-propyl ether, propylene glycol mono n-isopropyl ether, propylene glycol mono n-butyl ether, propylene glycol monotertiary butyl ether, propylene glycol mono n-hexyl ether, propylene Glycol monophenyl ether,
Dipropylene glycol monomethyl ether, dipropylene glycol monoethyl ether, dipropylene glycol mono n-propyl ether, dipropylene glycol monoisopropyl ether, dipropylene glycol mono n-butyl ether, dipropylene glycol monotertiary butyl ether, dipropylene glycol mono n -Hexyl ether,
Alcohol solvents such as tripropylene glycol monomethyl ether, tripropylene glycol monoethyl ether, tripropylene glycol mono n-propyl ether, and tripropylene glycol mono n-butyl ether;
Ethylene glycol monomethyl ether acetate, ethylene glycol monoethyl ether acetate, ethylene glycol mono n-propyl ether acetate, ethylene glycol monoisopropyl ether acetate, ethylene glycol mono n-butyl ether acetate, ethylene glycol monotertiary butyl ether acetate, ethylene glycol mono n- Hexyl ether acetate,
Diethylene glycol monomethyl ether acetate, diethylene glycol monoethyl ether acetate, diethylene glycol mono n-propyl ether acetate, diethylene glycol monoisopropyl ether acetate, diethylene glycol n-monobutyl ether acetate, diethylene glycol monotertiary butyl ether acetate, diethylene glycol mono n-hexyl ether acetate,
Propylene glycol monomethyl ether acetate, propylene glycol monoethyl ether acetate, propylene glycol mono n-propyl ether acetate, propylene glycol monoisopropyl ether acetate, propylene glycol mono n-butyl ether acetate, propylene glycol monotertiary butyl ether acetate, propylene glycol mono n- Hexyl ether acetate,
Dipropylene glycol monomethyl ether acetate, dipropylene glycol monoethyl ether acetate, dipropylene glycol mono n-propyl ether acetate, dipropylene glycol monoisopropyl ether acetate, dipropylene glycol mono n-butyl ether acetate, dipropylene glycol monotertiary butyl ether acetate Dipropylene glycol mono n-hexyl ether acetate,
And monoalkyl ether acetate solvents of glycols such as 3-methoxybutyl acetate;
Ethylene glycol dimethyl ether, ethylene glycol diethyl ether, diethylene glycol dimethyl ether, diethylene glycol diethyl ether, triethylene glycol dimethyl ether, trimethylene glycol diethyl ether, tetraethylene glycol dimethyl ether, tetraethylene glycol diethyl ether, propylene glycol dimethyl ether, propylene glycol diethyl ether, propylene glycol n -Dialkyl ether solvents of glycols such as butyl methyl ether, dipropylene glycol dimethyl ether, dipropylene glycol diethyl ether;
Ethylene glycol diacetate, diethylene glycol diacetate, propylene glycol diacetate, dipropylene glycol diacetate, 1,3-butylene glycol diacetate (also known as 1,3-butanediol diacetate), tetramethylene glycol acetate (also known as 1,4- Diacetate solvents of glycols such as butanediol diacetate), 1,5-heptanediol diacetate, and hexamethylene glycol diacetate (also known as 1,6-hexanediol diacetate);
Triacetate solvents such as glycerin triacetate (also known as triacetin);
Cyclic compound solvents having other oxygen atoms such as 1,4-dioxane, tetrahydrofuran, γ-butyrolactone, and the like;
A compound solvent having a nitrogen atom such as N, N-dimethylacetamide, N, N-dimethylformamide, and acetonitrile; and
Examples thereof include cyclic compound solvents having nitrogen atoms such as N-methylpyrrolidone, N-methyloxazolidinone, and N-ethyloxazolidinone, but are not limited to these, and are used alone or in combination of two or more. . The organic solvent can be used in an amount of 800 to 4,000 parts by weight, preferably 1,000 to 2,500 parts by weight with respect to 100 parts by weight of the colorant of the coloring composition.

  The disperser used for dispersing the coloring composition of the present invention is not particularly specified. For example, a horizontal sand mill, a vertical sand mill, an annular bead mill, an attritor, a microfluidizer, a high speed mixer, a homomixer, a ball mill, and a roll mill. , Stone mill, ultrasonic disperser, paint conditioner and the like. Usually, any disperser or mixer used in preparing various dispersions can be used. Further, before the dispersion by various dispersers, a pre-dispersion by a kneader or a kneader mixer such as a three roll mill, or a solid dispersion by a two roll mill or the like may be performed. In addition, after being dispersed by various dispersers, post-processing for about several hours to one week in a heated state at 30 to 80 ° C., processing using an ultrasonic disperser or a collision type beadless disperser, etc. It is effective for imparting dispersion stability to the dispersion.

  When the colored composition of the present invention is dispersed, a dispersant (including a dispersion aid) such as a resin-type dispersant, a surfactant, and a pigment derivative can be appropriately contained. The dispersant exhibits an excellent effect in dispersing a colorant such as a pigment, and has a great effect of preventing reaggregation of the pigment after dispersion. Therefore, a color filter coloring composition dispersed using a dispersion aid is used. If desired, a color filter having excellent transparency can be obtained.

  A dispersing agent can be used in the quantity of 1-30 weight part with respect to 100 weight part of pigment | dyes in a coloring composition, Preferably it is 5-15 weight. The resin type pigment dispersant may function as a part of the resin used as a colorant carrier.

  The resin-type pigment dispersant has a pigment-affinity part that has the property of adsorbing to the pigment and a part that is compatible with the dye carrier, and adsorbs to the pigment to stabilize the dispersion of the pigment on the dye carrier. It works.

Examples of the resin-type dispersant include polyvinyl, polyurethane, polyester, polyether, formalin condensation, silicone, and composite polymers thereof.
Examples of the pigment affinity site include carboxyl groups, hydroxyl groups, phosphate groups, phosphate ester groups, sulfonate groups, hydroxyl groups, amino groups, quaternary ammonium bases, amide groups, and other polar groups, as well as polyethylene oxide and polypropylene oxide. , And hydrophilic polymer chains of these composite systems, etc.
Examples of the site compatible with the dye carrier include a long-chain alkyl chain, a polyvinyl chain, a polyether chain, and a polyester chain.

Specifically, as a resin-type pigment dispersant,
Styrene-maleic anhydride copolymer, olefin-maleic anhydride copolymer, poly (meth) acrylate, styrene- (meth) acrylic acid copolymer, (meth) acrylic acid- (meth) acrylic acid alkyl ester Copolymer, (meth) acrylic acid-polyvinyl-based macromer copolymer, phosphoric ester group-containing acrylic resin, aromatic carboxyl group-containing acrylic resin, polystyrene sulfonate, acrylamide- (meth) acrylic acid copolymer, carboxymethylcellulose An anionic resin type pigment dispersant such as polyurethane having a carboxyl group, formalin condensate of naphthalene sulfonate, and sodium alginate;
Nonionic resin-type pigment dispersants such as polyvinyl alcohol, polyalkylene polyamine, polyacrylamide, and polymer starch; and
Polyethyleneimine, aminoalkyl (meth) acrylate copolymer, polyvinyl imidazoline, polyurethane having amino group, reaction product of poly (lower alkyleneimine) and polyester having free carboxyl group, and cationic resin type pigment such as satkinsan A dispersing agent is mentioned, These can be used individually or in mixture of 2 or more types.

As a commercially available resin-type pigment dispersant,
Disperbyk-101, 103, 107, 108, 110, 111, 116, 130, 140, 154, 161, 162, 163, 164, 165, 166, 170, 171, 174, 180, 181, 182, 183, 184, 185, 190, 2000, 2001, 2020, 2090, 2091, 2164, and 2163, Anti-Terra-U, 203, and 204, BYK-P104, P104S, and 220S, and Lactimon, Lactimon-WS , And BYKUMEN et al.
SOLPERSE-3000, 9000, 13240, 13650, 13940, 17000, 18000, 20000, 21000, 24000, 26000, 27000, 28000, 31845, 32000, 32500, 32600, 34750, 36600, 38500, 41000, 41090, and 53095, etc. Nippon Lubrizol resin-type pigment dispersant;
EFKA-46, 47, 48, 452, LP4008, 4009, LP4010, LP4050, LP4055, 400, 401, 402, 403, 450, 451, 453, 4540, 4550, LP4560, 120, 150, 1501, 1502, and 1503 Examples include resin-type pigment dispersants manufactured by Fuka Chemicals, etc., but are not limited thereto, and any resin-type pigment dispersant can be used, and these may be used alone or in admixture of two or more. it can.

As surfactant,
Polyoxyethylene alkyl ether sulfate, sodium dodecylbenzenesulfonate, alkali salt of styrene-acrylic acid copolymer, sodium alkylnaphthalenesulfonate, sodium alkyldiphenyletherdisulfonate, lauryl sulfate monoethanolamine, lauryl sulfate triethanolamine, lauryl Anionic surfactants such as ammonium sulfate, monoethanolamine stearate, sodium stearate, sodium lauryl sulfate, monoethanolamine of styrene-acrylic acid copolymer, polyoxyethylene alkyl ether phosphate;
Nonionic surfactants such as polyoxyethylene oleyl ether, polyoxyethylene lauryl ether, polyoxyethylene nonylphenyl ether, polyoxyethylene alkyl ether phosphate, polyoxyethylene sorbitan monostearate, polyethylene glycol monolaurate;
Chaotic surfactants such as alkyl quaternary ammonium salts and their ethylene oxide adducts; and
Examples include alkylbetaines such as alkyldimethylaminoacetic acid betaines, and amphoteric surfactants such as alkylimidazolines, and these can be used alone or in admixture of two or more.

  A dye derivative is a compound in which a substituent is introduced into an organic dye, and the organic dye also includes light yellow aromatic polycyclic compounds such as naphthalene, anthraquinone, and triazine that are not generally called dyes. It is. Examples of the dye derivative are described in JP-A-63-305173, JP-B-57-15620, JP-B-59-40172, JP-B-63-17102, JP-B-5-9469, and the like. These can be used alone or in combination of two or more.

  In particular, a pigment derivative having a basic functional group and a triazine derivative having a basic functional group are preferably used because of a large pigment dispersion effect. Specific examples of the basic functional group possessed by the dye derivative include substituents represented by the following general formulas (2), (3), (4) and (5).

General formula (2):

General formula (3):

General formula (4):

General formula (5):

[In general formula (2)-(5),
X ¹¹ is SO ₂ , CO, CH ₂ NHCOCH ₂ , CH ₂ , or a direct bond,
n ¹¹ is an integer of 1 to 10,
R ¹¹ and R ¹² are each independently an optionally substituted alkyl group having 1 to 36 carbon atoms, an optionally substituted alkenyl group having 2 to 36 carbon atoms, or an optionally substituted phenyl group. Or R ¹¹ And R ¹² together to form a heterocyclic ring,
R ¹³ is an optionally substituted alkyl group having 1 to 36 carbon atoms, an optionally substituted alkenyl group having 2 to 36 carbon atoms, or an optionally substituted phenyl group;
R ¹⁴ , R ¹⁵ , R ¹⁶ , and R ¹⁷ are each independently a hydrogen atom, an optionally substituted alkyl group having 1 to 36 carbon atoms, or an optionally substituted alkenyl group having 2 to 36 carbon atoms. Or an optionally substituted phenyl group,
Y ¹¹ represents —NR ¹⁸ —Z ¹¹ —NR ¹⁹ — or a direct bond.

R ¹⁸ and R ¹⁹ are each independently a hydrogen atom, an optionally substituted alkyl group having 1 to 36 carbon atoms, an optionally substituted alkenyl group having 2 to 36 carbon atoms, or a substituted group. A good phenyl group,
Z ¹¹ is an optionally substituted alkylene group having 1 to 36 carbon atoms, an optionally substituted alkenylene group having 2 to 36 carbon atoms, or an optionally substituted phenylene group,
P ¹¹ is a substituent represented by the general formula (6) or a substituent represented by the general formula (7),
Q ¹¹ is a hydroxyl group, an alkoxyl group, a substituent represented by the general formula (6), or a substituent represented by the general formula (7).
Formula (6), and in the general formula (7), R ¹¹ to R ¹⁷ and n ¹¹ are the same as R ¹¹ to R ¹⁷ and n ¹¹ in the general formula (2) to the general formula (4).

General formula (6):

General formula (7):
]

Examples of organic dyes constituting dye derivatives having basic functional groups include diketopyrrolopyrrole dyes, azo dyes such as azo, disazo, and polyazo; phthalocyanine dyes; diaminodianthraquinones, anthrapyrimidines, and flavantrons Anthraquinone dyes such as Antanthrone, Indanthrone, Pyrantron, and Biolantron;
Dioxazine dyes; Perinone dyes; Perylene dyes; Thioindigo dyes;
Isoindoline dyes; isoindolinone dyes; quinophthalone dyes; selenium dyes; and metal complex dyes. Moreover, the organic pigment illustrated previously may be sufficient.

  A pigment derivative having a basic group can be synthesized by various synthetic routes. For example, after introducing a substituent represented by the following formulas (8) to (11) into an organic dye, it reacts with the substituent to form a substituent represented by the general formulas (2) to (5). Amine components such as N, N-dimethylaminopropylamine, N-methylpiperazine, diethylamine, or 4- [4-hydroxy-6- [3- (dibutylamino) propylamino] -1,3,5-triazine It can be obtained by reacting 2-ylamino] aniline or the like.

When the organic dye is an azo dye, a basic functional group is obtained by previously introducing a substituent represented by the general formulas (2) to (5) into a diazo component or a coupling component, and then performing a coupling reaction. It is also possible to produce an azo pigment derivative having
Formula (8): —SO ₂ Cl
Formula (9): -COCl
Formula (10): —CH ₂ NHCOCH ₂ Cl
Formula (11): —CH ₂ Cl

  Examples of the amine component used for forming the substituents represented by the general formulas (2) to (5) include dimethylamine, diethylamine, N, N-ethylisopropylamine, N, N-ethylpropylamine. N, N-methylbutylamine, N, N-methylisobutylamine, N, N-butylethylamine, N, N-tert-butylethylamine, diisopropylamine, dipropylamine, N, N-sec-butylpropylamine, di Butylamine, di-sec-butylamine, diisobutylamine, N, N-isobutyl-sec-butylamine, diamylamine, diisoamylamine, dihexylamine, di (2-ethylhexyl) amine, dioctylamine, N, N-methyloctadecylamine, Didecylamine, diallylamine, N N-ethyl-1,2-dimethylpropylamine, N, N-methylhexylamine, dioleylamine, distearylamine, N, N-dimethylaminomethylamine, N, N-dimethylaminoethylamine, N, N-dimethylamino Amylamine, N, N-dimethylaminobutylamine, N, N-diethylaminoethylamine, N, N-diethylaminopropylamine, N, N-diethylaminohexylamine, N, N-diethylaminobutylamine, N, N-diethylaminopentylamine, N , N-dipropylaminobutylamine, N, N-dibutylaminopropylamine, N, N-dibutylaminoethylamine, N, N-dibutylaminobutylamine, N, N-diisobutylaminopentylamine, N, N-methyl-laurylamino The Pyramine, N, N-ethyl-hexylaminoethylamine, N, N-distearylaminoethylamine, N, N-dioleylaminoethylamine, N, N-distearylaminobutylamine, piperidine, 2-pipecholine, 3-pipecholine, 4 -Pipecoline, 2,4-Lupetidine, 2,6-Lupetidine, 3,5-Lupetidine, 3-piperidinemethanol, Pipecolic acid, Isonipecotate, Methyl isonipecotate, Ethyl isonipecotate, 2-Piperidinethanol, Pyrrolidine, 3-hydroxy Pyrrolidine, N-aminoethylpiperidine, N-aminoethyl-4-pipecholine, N-aminoethylmorpholine, N-aminopropylpiperidine, N-aminopropyl-2-pipecholine, N-aminopropyl-4-pipecholine, N-amino Examples include propylmorpholine, N-methylpiperazine, N-butylpiperazine, N-methylhomopiperazine, 1-cyclopentylpiperazine, 1-amino-4-methylpiperazine, and 1-cyclopentylpiperazine.

  As the pigment derivative, those shown in Tables 1 to 9 can be used, but are not limited thereto. The pigment derivatives can be used alone or in admixture of two or more.

MAT

MAT

MAT

  Next, the color filter of the present invention will be described.

  The color filter of this invention is a color filter which comprises the filter segment formed using the coloring composition for color filters of this invention.

  The color filter includes an additive color mixing type including at least one red filter segment, at least one green filter segment, and at least one blue filter segment, at least one magenta color filter segment, and at least one cyan color filter segment. And a subtractive color type having at least one yellow filter segment.

  The blue filter segment, the green filter segment, and the cyan filter segment can be formed using the coloring composition for a color filter of the present invention.

  The color filter of the present invention is produced by forming filter segments of each color on a transparent substrate using the colored composition of the present invention and the above-described colored composition by a printing method, an ink jet method, or a photolithography method. can do.

The red coloring composition for forming a red filter segment is, for example, C.I. I. Pigment Red 7, 9, 14, 41, 48: 1, 48: 2, 48: 3, 48: 4, 81: 1, 81: 2, 81: 3, 97, 122, 123, 146, 149, 168, 177, 178, 180, 184, 185, 187, 192, 200, 202, 208, 210, 215, 216, 217, 220, 223, 224, 226, 227, 228, 240
Red pigments such as 246, 254, 255, 264, and 272, pigment carriers (resin and / or resin precursors), solvents as necessary, and various additives (dispersants, photopolymerization initiators, leveling) A red coloring composition containing an agent and the like. The red coloring composition includes yellow pigments exemplified later, C.I. I. Orange pigments such as Pigment Orange 36, 43, 51, 55, 59, and 61 can be used in combination.

  The green coloring composition for forming the green filter segment is, for example, C.I. I. Pigment Green 7, 10, 36, 37, etc., a green pigment, a pigment carrier (resin and / or resin precursor), if necessary, a solvent, and various additives (dispersant, photopolymerization initiator, leveling agent) Etc.) and the like. A yellow pigment exemplified later can be used in combination with the green coloring composition. In the present invention, if necessary, the colorant of the present invention is used instead of the green pigment.

The blue coloring composition for forming a blue filter segment is, for example, C.I. I. Pigment Blue 15, 15: 1, 15: 2, 15: 3, 15: 4, 15: 6, 16
, 22, 60, 64, etc. Blue pigment, pigment carrier (resin and / or resin precursor), solvent, and various additives (dispersant, photopolymerization initiator, leveling agent, etc.) as required It is a blue coloring composition formed by containing. Blue coloring compositions include C.I. I. Pigment Violet 1, 19, 23, 27, 29, 30, 32, 37, 40, 42, and 50 can be used in combination. In the present invention, the colorant of the present invention is used in place of the blue pigment as necessary.

  The yellow coloring composition for forming the yellow filter segment is, for example, C.I. I. Pigment Yellow 1, 2, 3, 4, 5, 6, 10, 12, 13, 14, 15, 16, 17, 18, 20, 24, 31, 32, 34, 35, 35: 1, 36, 36: 1, 37, 37: 1, 40, 42, 43, 53, 55, 60, 61, 62, 63, 65, 73, 74, 77, 81, 83, 86, 93, 94, 95, 97, 98, 100, 101, 104, 106, 108, 109, 110, 113, 114, 115, 116, 117, 118, 119, 120, 123, 125, 126, 127, 128, 129, 137, 138, 139, 147, 148, 150, 151, 152, 153, 154, 155, 156, 161, 162, 164, 166, 167, 168, 169, 170, 171, 172, 173, 174, 1 Yellow pigments such as 75, 176, 177, 179, 180, 181, 182, 185, 187, 188, 193, 194, and 199, and a pigment carrier (resin and / or resin precursor), if necessary, It is a yellow coloring composition containing a solvent and various additives (dispersant, photopolymerization initiator, leveling agent, etc.) and the like.

  The magenta coloring composition for forming the magenta color filter segment is, for example, C.I. I. Pigment Violet 1 and 19 and other purple pigments and / or C.I. I. Pigment Red 4, 146, 177, 169, and 81, red pigment, pigment carrier (resin and / or resin precursor), solvent, and various additives (dispersant, photopolymerization initiator, A magenta coloring composition containing a leveling agent and the like. The yellow pigment can be used in combination with the magenta colored composition.

  Cyan coloring compositions for forming cyan filter segments are, for example, C.I. I. Pigment Blue 15: 1, 15: 2, 15: 4, 15: 3, 15: 6, 16, and 81, etc. Blue pigment, pigment carrier (resin and / or precursor of resin), solvent if necessary , And various additives (dispersant, photopolymerization initiator, leveling agent, etc.) and the like. In the present invention, the colorant of the present invention is used in place of the blue pigment as necessary.

  As the transparent substrate, a glass plate or a resin plate such as polycarbonate, polymethyl methacrylate, and polyethylene terephthalate is used.

  The formation of each color filter segment by the printing method or the ink jet method can be patterned simply by repeating the printing and drying of the colored composition prepared as the above various printing inks. Excellent in properties. Furthermore, a fine pattern having high dimensional accuracy and smoothness can be printed by the development of printing technology. In order to perform printing, it is preferable that the ink is not dried and solidified on the printing plate or on the blanket. Control of the fluidity of the ink on the printing machine is also important, and the ink viscosity can be adjusted with a dispersant or extender pigment.

  The composition of the ink as the coloring composition is, for example, a colorant (pigment or the like), a resin and a resin precursor, a solvent, and other additives. As a part of the resin, a resin-type dispersant can be arbitrarily used, and as a part of the additive, a pigment derivative can be arbitrarily used.

  For example, in the case of a thermosetting ink, a thermosetting resin as a resin, a precursor of the resin, an alkyl etherified methylol melamine compound, an alkyl etherified methylol benzoguanamine compound, a carbodiimide, depending on the functional group of the resin Thermally reactive compounds such as compounds, epoxy compounds, oxetane compounds, phenol compounds, benzoxidine compounds, blocked carboxylic acid compounds, blocked isocyanate compounds, (meth) acrylate monomers, and silane coupling agents are used as additives. Each reaction catalyst can optionally be used.

  Also, for example, in the case of an active energy ray curable ink, as a resin, a photosensitive resin, as a resin precursor, an active energy ray curable monomer such as a (meth) acrylate monomer, as an additive, Each of the active energy ray polymerization initiators can be arbitrarily used.

  When each color filter segment is formed by photolithography, the colored composition prepared as the solvent development type or alkali development type color resist is applied on a transparent substrate, such as spray coating, spin coating, slit coating, roll coating, etc. By a method, it applies so that a dry film thickness may be set to 0.2-5 micrometers. If necessary, the dried film is exposed to ultraviolet light through a mask having a predetermined pattern provided in contact with or non-contact with the film. Then, after immersing in a solvent or an alkali developer or spraying the developer with a spray or the like to remove the uncured portion to form a desired pattern, the same operation is repeated for other colors to produce a color filter. be able to. Furthermore, in order to accelerate the polymerization of the colored resist, heating can be performed as necessary. According to the photolithography method, a color filter with higher accuracy than the above printing method can be manufactured.

  The composition of the resist as the coloring composition is, for example, a colorant (pigment or the like), a resin and a resin precursor, a solvent, and other additives. As a part of the resin, a resin-type dispersant can be arbitrarily used, and as a part of the additive, a pigment derivative can be arbitrarily used.

  In the case of a resist, each color filter segment is formed by a photolithography method. Therefore, an active energy ray is used as a resin, an alkali-soluble resin, a precursor of the resin, an active energy ray-curable monomer, and an additive. A polymerization initiator can be arbitrarily used.

  In addition, when the color filter coloring composition of the present invention is used in the form of an alkali development type colored resist, an ethylenically unsaturated monomer having an acidic group such as (meth) acrylic acid is used as the alkali-soluble resin. It is preferable to use the copolymerized alkali-soluble vinyl resin as a precursor thereof, the following ethylenically unsaturated monomer as an additive, and the following active energy ray polymerization initiator as an additive.

As monomers and oligomers that are resin precursors, that is, ethylenically unsaturated monomers,
Methyl (meth) acrylate, ethyl (meth) acrylate, propyl (meth) acrylate, isopropyl (meth) acrylate, butyl (meth) acrylate, isobutyl (meth), tertiary butyl (meth) acrylate, isoamyl (meth) acrylate, octyl (Meth) acrylate, isooctyl (meth) acrylate, 2-ethylhexyl (meth) acrylate, cetyl (meth) acrylate, decyl (meth) acrylate, isodecyl (meth) acrylate, lauryl (meth) acrylate, tridecyl (meth) acrylate, iso Linear or branched alkyl (meth) acrylates such as myristyl (meth) acrylate, stearyl (meth) acrylate, and isostearyl (meth) acrylate;
Cyclohexyl (meth) acrylate, Tertiarybutylcyclohexyl (meth) acrylate, Dicyclopentanyl (meth) acrylate, Dicyclopentanyloxyethyl (meth) acrylate, Dicyclopentenyl (meth) acrylate, Dicyclopentenyloxyethyl (meth) ) Acrylates and cyclic alkyl (meth) acrylates such as isobornyl (meth) acrylate;
Fluoroalkyl (meth) acrylates such as trifluoroethyl (meth) acrylate, octafluoropentyl (meth) acrylate, perfluorooctylethyl (meth) acrylate, and tetrafluoropropyl (meth) acrylate;
(Meth) acryloxy-modified polydimethylsiloxanes (silicone macromers);
(Meth) acrylates having a heterocyclic ring such as tetrahydrofurfuryl (meth) acrylate and 3-methyl-3-oxetanyl (meth) acrylate;
Benzyl (meth) acrylate, phenoxyethyl (meth) acrylate, phenoxypolyethylene glycol (meth) acrylate, paracumylphenoxyethyl (meth) acrylate, paracumylphenoxypolyethylene glycol (meth) acrylate, nonylphenoxypolyethylene glycol (meth) acrylate, etc. (Meth) acrylates having the following aromatic ring;
2-methoxyethyl (meth) acrylate, 2-ethoxyethyl (meth) acrylate, 3-methoxybutyl (meth) acrylate, 2-methoxypropyl (meth) acrylate, diethylene glycol monomethyl ether (meth) acrylate, diethylene glycol monoethyl ether (meta ) Acrylate, triethylene glycol monomethyl ether (meth) acrylate, triethylene glycol monoethyl ether (meth) acrylate, diethylene glycol mono-2-ethylhexyl ether (meth) acrylate, dipropylene glycol monomethyl ether (meth) acrylate, tripropylene glycol mono (Meth) acrylate, polyethylene glycol monolauryl ether (meth) acrylate, and polyester Glycol monostearyl ether (meth) acrylate of (poly) alkylene glycol monoalkyl ether (meth) acrylates;
(Meth) acrylic acid, acrylic acid dimer, 2- (meth) acryloyloxyethyl phthalate, 2- (meth) acryloyloxypropyl phthalate, 2- (meth) acryloyloxyethyl hexahydrophthalate, 2- (meth) (Meth) acrylates having a carboxyl group such as acryloyloxypropylhexahydrophthalate, ethylene oxide-modified succinic acid (meth) acrylate, β-carboxyethyl (meth) acrylate, and ω-carboxypolycaprolactone (meth) acrylate;
2-hydroxyethyl (meth) acrylate, 2-hydroxypropyl (meth) acrylate, 2-hydroxybutyl (meth) acrylate, 4-hydroxybutyl (meth) acrylate, 2-acryloyloxyethyl-2-hydroxyethyl (meth) Phthalate, diethylene glycol mono (meth) acrylate, dipropylene glycol mono (meth) acrylate, polyethylene glycol mono (meth) acrylate, propylene glycol mono (meth) acrylate, polypropylene glycol mono (meth) acrylate, polytetramethylene glycol mono (meth) Acrylate, poly (ethylene glycol-propylene glycol) mono (meth) acrylate, poly (ethylene glycol-tetramethylene glycol) mono (meth) Acrylate, poly (propylene glycol - tetramethylene glycol) mono (meth) acrylate, and a hydroxyl group, such as glycerol (meth) acrylate (meth) acrylates;
Ethylene glycol di (meth) acrylate, diethylene glycol di (meth) acrylate, triethylene glycol di (meth) acrylate, polyethylene glycol di (meth) acrylate, propylene glycol di (meth) acrylate, dipropylene glycol di (meth) acrylate, tri Propylene glycol di (meth) acrylate, polypropylene glycol di (meth) acrylate, poly (ethylene glycol-propylene glycol) di (meth) acrylate, poly (ethylene glycol-tetramethylene glycol) di (meth) acrylate, poly (propylene glycol- Tetramethylene glycol) di (meth) acrylate, polytetramethylene glycol di (meth) acrylate, 1,3-butanediol di (Meth) acrylate, neopentyl glycol di (meth) acrylate, 1,6-hexanediol di (meth) acrylate, 1,9-nonanediol di (meth) acrylate, and 2-ethyl, 2-butyl-propanediol di ( (Poly) alkylene glycol di (meth) acrylates such as (meth) acrylate,
Dimethylol dicyclopentane di (meth) acrylate, hydroxypivalic acid neopentyl glycol di (meth) acrylate, stearic acid modified pentaerythritol di (meth) acrylate, ethylene oxide modified bisphenol A di (meth) acrylate, propylene oxide modified bisphenol A Di (meth) acrylate, tetramethylene oxide modified bisphenol A di (meth) acrylate, ethylene oxide modified bisphenol F di (meth) acrylate, propylene oxide modified bisphenol F di (meth) acrylate, tetramethylene oxide modified bisphenol F di (meth) Acrylate, zinc diacrylate, ethylene oxide-modified phosphate triacrylate, and glycerol di (meth) acrylate Di (meth) acrylate and the like;
(Meth) acrylates having a tertiary amino group such as dimethylaminoethyl (meth) acrylate, diethylaminoethyl (meth) acrylate, dimethylaminopropyl (meth) acrylate, diethylaminopropyl (meth) acrylate;
Glycerol tri (meth) acrylate, trimethylolpropane tri (meth) acrylate, pentaerythritol tri (meth) acrylate, pentaerythritol tetra (meth) acrylate, dipentaerythritol penta (meth) acrylate, and dipentaerythritol hexa (meth) acrylate Trifunctional or higher polyfunctional (meth) acrylates such as
Glycerol triglycidyl ether- (meth) acrylic acid adduct, glycerol diglycidyl ether- (meth) acrylic acid adduct, polyglycerol polyglycidyl ether- (meth) acrylic acid adduct, 1,6-butanediol diglycidyl ether, Alkyl glycidyl ether- (meth) acrylic acid adduct, allyl glycidyl ether- (meth) acrylic acid adduct, phenyl glycidyl ether- (meth) acrylic acid adduct, styrene oxide- (meth) acrylic acid adduct, bisphenol A di Glycidyl ether- (meth) acrylic acid adduct, propylene oxide-modified bisphenol A diglycidyl ether- (meth) acrylic acid adduct, bisphenol F diglycidyl ether- (meth) acrylic acid adduct, epichlorohydride -Modified phthalic acid- (meth) acrylic acid adduct, epichlorohydrin-modified hexahydrophthalic acid- (meth) acrylic acid adduct, ethylene glycol diglycidyl ether- (meth) acrylic acid adduct, polyethylene glycol diglycidyl ether- (meta ) Acrylic acid adduct, propylene glycol diglycidyl ether- (meth) acrylic acid adduct, polypropylene glycol diglycidyl ether- (meth) acrylic acid adduct, phenol novolac type epoxy resin- (meth) acrylic acid adduct, cresol novolac Type epoxy resins-(meth) acrylic acid adducts, other epoxy resins-epoxy (meth) acrylates such as (meth) acrylic acid adducts;
(Meth) acryloyl modified isocyanurate, (meth) acryloyl modified polyurethane, (meth) acryloyl modified polyester, (meth) acryloyl modified melamine, (meth) acryloyl modified silicone, (meth) acryloyl modified polybutadiene, and (meth) acryloyl modified rosin (Meth) acryloyl-modified resin oligomers such as;
Vinyls such as styrene, α-methylstyrene, vinyl acetate, vinyl (meth) acrylate, and allyl (meth) acrylate;
Vinyl ethers such as hydroxyethyl vinyl ether, ethylene glycol divinyl ether, and pentaerythritol trivinyl ether;
Amides such as (meth) acrylamide, N-hydroxymethyl (meth) acrylamide, and N-vinylformamide; and
Examples include acrylonitrile. These can be used alone or in admixture of two or more.

  Among these precursors, an alkali-soluble resin is obtained by copolymerizing (meth) acrylates having a carboxyl group with monofunctional (meth) acrylates and / or vinyls having no carboxyl group. can get.

  Of these precursors, polyfunctional (meth) acrylates and / or vinyls are preferably used as the active energy ray-curable monomer.

As an active energy ray polymerization initiator,
4-phenoxydichloroacetophenone, 4-t-butyl-dichloroacetophenone, diethoxyacetophenone, 1- (4-isopropylphenyl) -2-hydroxy-2-methylpropan-1-one, 1-hydroxycyclohexyl phenyl ketone, 2- Methyl-1- [4- (methylthio) phenyl] -2-morpholinopropan-1-one, 2- (dimethylamino) -2-[(4-methylphenyl) methyl] -1- [4- (4- Acetophenone compounds such as morpholinyl) phenyl] -1-butanone and 2-benzyl-2-dimethylamino-1- (4-morpholinophenyl) -butan-1-one;
Benzoin compounds such as benzoin, benzoin methyl ether, benzoin ethyl ether, benzoin isopropyl ether, and benzyldimethyl ketal;
Benzophenone, benzoylbenzoic acid, methyl benzoylbenzoate, 4-phenylbenzophenone, hydroxybenzophenone, acrylated benzophenone, 4-benzoyl-4'-methyldiphenyl sulfide, and 3,3 ', 4,4'-tetra (t-butyl Peroxycarbonyl) benzophenone compounds such as benzophenone;
Thioxanthone compounds such as thioxanthone, 2-chlorothioxanthone, 2-methylthioxanthone, isopropylthioxanthone, 2,4-diisopropylthioxanthone, and 2,4-diethylthioxanthone;
2,4,6-trichloro-s-triazine, 2-phenyl-4,6-bis (trichloromethyl) -s-triazine, 2- (p-methoxyphenyl) -4,6-bis (trichloromethyl) -s -Triazine, 2- (p-tolyl) -4,6-bis (trichloromethyl) -s-triazine, 2-piperonyl-4,6-bis (trichloromethyl) -s-triazine, 2,4-bis (trichloro) Methyl) -6-styryl-s-triazine, 2- (naphth-1-yl) -4,6-bis (trichloromethyl) -s-triazine, 2- (4-methoxy-naphth-1-yl) -4 , 6-Bis (trichloromethyl) -s-triazine, 2,4-trichloromethyl- (piperonyl) -6-triazine, and 2,4-trichloromethyl- (4′-methoxystyryl) -6 -Triazine compounds such as triazine;
1,2-octanedione, 1- [4- (phenylthio)-, 2- (O-benzoyloxime)], and O- (acetyl) -N- (1-phenyl-2-oxo-2- (4 ′ Oxime ester compounds such as -methoxy-naphthyl) ethylidene) hydroxylamine;
Phosphine compounds such as bis (2,4,6-trimethylbenzoyl) phenylphosphine oxide and 2,4,6-trimethylbenzoyldiphenylphosphine oxide;
Quinone compounds such as 9,10-phenanthrenequinone, camphorquinone, and ethylanthraquinone;
Borate compounds;
A carbazole compound;
An imidazole compound; and
A titanocene compound or the like is used.

  These active energy ray polymerization initiators can be used alone or in combination of two or more in any ratio as required. These active energy ray polymerization initiators can be used in an amount of 5 to 200 parts by weight, preferably 10 to 150 parts by weight, with respect to 100 parts by weight of the dye in the color filter coloring composition.

  Furthermore, the coloring composition for a color filter of the present invention can contain a sensitizer. The sensitizer can be used in an amount of 0.1 to 60 parts by weight with respect to 100 parts by weight of the photopolymerization initiator in the colored composition.

  Sensitizers include unsaturated ketones typified by chalcone derivatives and dibenzalacetone, 1,2-diketone derivatives typified by benzyl and camphorquinone, benzoin derivatives, fluorene derivatives, naphthoquinone derivatives, anthraquinone derivatives , Xanthene derivatives, thioxanthene derivatives, xanthone derivatives, thioxanthone derivatives, coumarin derivatives, ketocoumarin derivatives, cyanine derivatives, merocyanine derivatives, oxonol derivatives, and other polymethine dyes, acridine derivatives, azine derivatives, thiazine derivatives, oxazine derivatives, indoline derivatives, Azulene derivatives, azurenium derivatives, squarylium derivatives, porphyrin derivatives, tetraphenylporphyrin derivatives, triarylmethane derivatives, tetrabenzoporphyrin derivatives, Trapirazinoporphyrazine derivatives, phthalocyanine derivatives, tetraazaporphyrazine derivatives, tetraquinoxalyloporphyrazine derivatives, naphthalocyanine derivatives, subphthalocyanine derivatives, pyrylium derivatives, thiopyrylium derivatives, tetraphylline derivatives, annulene derivatives, spiropyran derivatives, spirooxazine Derivatives, thiospiropyran derivatives, metal arene complexes, organoruthenium complexes, Michler's ketone derivatives, and the like.

  Specific examples include Okawara Nobu et al., “Dye Handbook” (1986, Kodansha), Okawara Nobu et al., “Functional Dye Chemistry” (1981, CMC), Ikemori Chusaburo et al. Examples include, but are not limited to, the sensitizers described in “Special Functional Materials” (1986, CMC). In addition, a sensitizer that absorbs light from the ultraviolet region to the near infrared region can be contained.

  Two or more kinds of sensitizers may be used in any ratio as required.

Moreover, the coloring composition for a color filter of the present invention can contain an amine compound having a function of reducing dissolved oxygen.
Such amine compounds include triethanolamine, methyldiethanolamine, triisopropanolamine, methyl 4-dimethylaminobenzoate, ethyl 4-dimethylaminobenzoate, isoamyl 4-dimethylaminobenzoate, 2-dimethylaminobenzoate. Examples include ethyl, 2-ethylhexyl 4-dimethylaminobenzoate, and N, N-dimethylparatoluidine.

  In addition, the coloring composition for a color filter of the present invention can contain a storage stabilizer for stabilizing the viscosity of the composition with time, and a silane cup for improving the adhesion to the transparent substrate. An adhesion improving agent such as a ring agent may be contained.

Examples of storage stabilizers include:
Quaternary ammonium chlorides such as benzyltrimethylammonium chloride and diethylhydroxyamine;
Organic acids such as lactic acid and oxalic acid;
Methyl esters of the organic acids;
catechols such as t-butylpyrocatechol;
Organic phosphines such as triphenylphosphine, tetraethylphosphine, and tetraphenylphosphine; and
Examples thereof include phosphites.

As a silane coupling agent,
Vinylsilanes such as vinyltris (β-methoxyethoxy) silane, vinylethoxysilane, and vinyltrimethoxysilane;
(meth) acryloxysilanes such as γ- (meth) acryloxypropyltrimethoxysilane, γ- (meth) acryloxypropyltriethoxysilane, and γ- (meth) acryloxypropyldimethoxymethylsilane;
β- (3,4-epoxycyclohexyl) ethyltrimethoxysilane, β- (3,4-epoxycyclohexyl) methyltrimethoxysilane, β- (3,4-epoxycyclohexyl) ethyltriethoxysilane, β- (3, Epoxy silanes such as 4-epoxycyclohexyl) methyltriethoxysilane, γ-glycidoxypropyltrimethoxysilane, and γ-glycidoxypropyltriethoxysilane;
N-β (aminoethyl) γ-aminopropyltrimethoxysilane, N-β (aminoethyl) γ-aminopropyltriethoxysilane, N-β (aminoethyl) γ-aminopropylmethyldiethoxysilane, γ-amino Aminosilanes such as propyltriethoxysilane, γ-aminopropyltrimethoxysilane, N-phenyl-γ-aminopropyltrimethoxysilane, and N-phenyl-γ-aminopropyltriethoxysilane; and
and thiosilanes such as γ-mercaptopropyltrimethoxysilane and γ-mercaptopropyltriethoxysilane;

  The silane coupling agent can be used in an amount of 0.01 to 10 parts by weight, preferably 0.05 to 5 parts by weight, with respect to 100 parts by weight of the dye in the color filter coloring composition.

  In the coloring composition for color filters of the present invention, as other additives, chain transfer agents, plasticizers, surface conditioners, UV inhibitors, light stabilizers, antioxidants, antistatic agents, antiblocking agents and antifoaming agents Viscosity modifiers, waxes, leveling agents and the like can be added.

  In development, an aqueous solution such as sodium carbonate or sodium hydroxide is used as an alkali developer, and an organic alkali such as dimethylbenzylamine or triethanolamine can also be used. An antifoaming agent or a surfactant can also be added to the developer. In order to increase the UV exposure sensitivity, after coating and drying the colored resist, a water-soluble or alkaline water-soluble resin such as polyvinyl alcohol or a water-soluble acrylic resin is applied and dried to form a film that prevents polymerization inhibition by oxygen. Thereafter, ultraviolet exposure can also be performed.

  The color filter of the present invention can be produced by an electrodeposition method, a transfer method or the like in addition to the above method, but the colored composition of the present invention can be used in any method. The electrodeposition method is a method for producing a color filter by using a transparent conductive film formed on a transparent substrate and forming each color filter segment on the transparent conductive film by electrophoresis of colloidal particles. is there. The transfer method is a method in which a color filter layer is formed in advance on the surface of a peelable transfer base sheet, and this color filter layer is transferred to a desired transparent substrate.

  The present invention will be described in more detail with reference to the following examples. However, the following examples do not limit the scope of rights of the present invention. In the examples, “parts” and “%” represent “parts by weight” and “% by weight”, respectively.

(Synthesis of Exemplified Compound 1)
According to the nitrile method, chloroaluminum phthalocyanine was obtained from phthalodinitrile and an aluminum chloride anhydride using DBU (1,8-Diazabicyclo [5.4.0] undec-7-ene) as a catalyst. 100 parts of chloroaluminum phthalocyanine was slowly added to 2000 parts of concentrated sulfuric acid at room temperature. The mixture was stirred at 40 ° C. for 2 hours, and the sulfuric acid solution was poured into 80000 parts of cold water at 3 ° C. The precipitated blue product was filtered, washed with water and dried to obtain hydroxyaluminum phthalocyanine.

  100 parts of the resulting hydroxyaluminum phthalocyanine and 54.6 parts of triphenylsilanol were added to 400 parts of toluene. Heating at reflux was continued for 4 hours. After filtration, washing with methanol and drying, 119 parts of Exemplified Compound 1 represented by the following general formula (12) was obtained. The structure of Exemplified Compound 1 was confirmed by accurate mass spectrometry and elemental analysis. The results are summarized in Table 9.

Formula (12):

(Synthesis of Comparative Compound 1)
100 parts of hydroxyaluminum phthalocyanine obtained as a synthetic intermediate of exemplary compound 1 was added to 1500 parts of nitrobenzene. Heating at reflux was continued for 6 hours. After filtration, washing with methanol and drying, 98 parts of Comparative Compound 1 represented by the following general formula (20) was obtained. The structure of Comparative Compound 1 which is a μ-oxoaluminum phthalocyanine dimer was confirmed by accurate mass spectrometry and elemental analysis. The results are summarized in Table 9.

Formula (20):

(Preparation of acrylic resin solution)
Put 450 parts of cyclohexanone in a reaction vessel, heat to 80 ° C. while injecting nitrogen gas into the vessel, and at the same temperature, 20.0 parts of methacrylic acid, 10.0 parts of methyl methacrylate, 55.0 parts of n-butyl methacrylate A mixture of 15.0 parts of 2-hydroxyethyl methacrylate and 4.0 parts of 2,2′-azobisisobutyronitrile was added dropwise over 1 hour to carry out a polymerization reaction. After completion of the dropwise addition, the mixture was further reacted at 80 ° C. for 3 hours, then 1.0 part of azobisisobutyronitrile dissolved in 50 parts of cyclohexanone was added, and the reaction was further continued at 80 ° C. for 1 hour. An acrylic resin solution was obtained. The weight average molecular weight of the acrylic resin was about 40,000. After cooling to room temperature, about 2 g of the resin solution was sampled, heated and dried at 180 ° C. for 20 minutes to measure the nonvolatile content, and cyclohexanone was added to the previously synthesized resin solution so that the nonvolatile content was 20% by weight. To prepare an acrylic resin solution.

(Colorant adjustment)
[Example 1]
Exemplified compound 1:36 parts, sodium chloride: 360 parts, and diethylene glycol: 46 parts were charged in a stainless steel 0.6 L kneader (manufactured by Inoue Seisakusho) and kneaded at 30 ° C. for 7 hours. Next, this kneaded product is poured into 3 liters of 70 ° C. warm water, stirred for 1 hour while heating to 70 ° C. to form a slurry, repeatedly filtered and washed with water to remove sodium chloride and diethylene glycol, and then at 80 ° C. overnight. Drying gave 33 parts of Colorant 1. When the X-ray diffraction pattern by CuKα ray of the obtained siloxyaluminum phthalocyanine pigment was measured, the black angle 2θ (± 0.2) = 6.1 °, 8.0 °, 9. 5 °, 10.7 °, 12.6 °, 13.6 °, 14.1 °, 14.8 °, 17.2 °, 18.3 °, 18.8 °, 19.2 °, 20. Peaks were observed at 4 °, 22.1 °, 23.8 °, 24.6 °, 26.3 °, and 27.8 °.

[Example 2]
Example Compound 1: 32.4 parts of hydroxyaldehyde phthalocyanine: 3.6 parts of sodium chloride: 360 parts, and diethylene glycol: were charged 46 parts of stainless steel 0.6L kneader (manufactured by Inoue Seisakusho), 7 at 30 ° C. Kneaded for hours. Next, this kneaded product is poured into 3 liters of 70 ° C. warm water, stirred for 1 hour while heating to 70 ° C. to form a slurry, repeatedly filtered and washed with water to remove sodium chloride and diethylene glycol, and then at 80 ° C. overnight. Drying gave 33 parts of Colorant 2. When the X-ray diffraction pattern by CuKα ray of the obtained siloxyaluminum phthalocyanine pigment was measured, the black angle 2θ (± 0.2) = 6.0 °, 7.5 °, 8. Peaks at 4 °, 9.8 °, 13.1 °, 15.1 °, 16.3 °, 18.5 °, 20.2 °, 21.3 °, 22.8 °, and 26.8 ° Had.

Comparative compound 1 was used as comparative colorant 1 as it was.

(Adjustment and evaluation of coloring composition)
Example 3
A colored composition 1 was prepared by uniformly dispersing a mixture having the following composition and filtering with a 5 μm filter.

Colorant 1 2.50 parts Yellow Pigment C.I. I. Pigment Yellow 150 2.50 parts (Yellow Pigment E4GN-GT manufactured by LANXESS)
Dye derivative A-14 1.0 part Acrylic resin solution 45.0 parts Trimethylolpropane triacrylate 7.30 parts ("NK ester ATMPT" manufactured by Shin-Nakamura Chemical Co., Ltd.)
Photopolymerization initiator (“Irgacure 907” manufactured by Ciba Geigy) 0.10 parts Sensitizer (“EAB-F” manufactured by Hodogaya Chemical Co., Ltd.) 0.10 parts Cyclohexane 41.5 parts

  Subsequently, using a spin coater, the colored composition 1 was applied onto the glass substrate so that the chromaticity when the F10 light source was used was x = 0.29. After drying at 70 ° C. for 20 minutes, an ultra high pressure mercury lamp was used to perform ultraviolet exposure with an integrated light amount of 150 mJ to prepare a color filter. Spectral transmittance was measured using a spectrophotometer ("U-3500" manufactured by Hitachi, Ltd.). The superiority or inferiority of the brightness was evaluated by the transmittance at 545 nm. The results are summarized in Table 10.

[Example 4, Comparative Examples 2-6]
The coloring agent 1 is a coloring agent 2, a comparative coloring agent 1, and Cyanine Blue A-13Y manufactured by Sanyo Dye Co., which is aluminum phthalocyanine, C.I. I. Pigment Blue 15: 6 (“Rionol BLUE E” manufactured by Toyo Ink Co., Ltd.), green pigment C.I. I. Pigment Green 36 (“Lionol Green 6YK” manufactured by Toyo Ink Co., Ltd.), or C.I. I. A colored composition 2 and comparative colored compositions 1 to 5 were obtained in the same manner as in Example 3 except that Pigment Green 58 (“A110” manufactured by DIC) was used. Evaluation was conducted in the same manner as in Example 3, and the results are summarized in Table 10.

Example 5
A mixture having the following composition was uniformly dispersed and filtered through a 5 μm filter to prepare a colored composition 3.

Colorant 1 2.50 parts Yellow Pigment C.I. I. Pigment Yellow 138 2.50 parts (Palito Gelb K0961HD manufactured by BASF)
Dye derivative A-14 1.0 part Acrylic resin solution 45.0 parts Trimethylolpropane triacrylate 7.30 parts ("NK ester ATMPT" manufactured by Shin-Nakamura Chemical Co., Ltd.)
Photopolymerization initiator (“Irgacure 907” manufactured by Ciba Geigy) 0.10 parts Sensitizer (“EAB-F” manufactured by Hodogaya Chemical Co., Ltd.) 0.10 parts Cyclohexane 41.5 parts

  Subsequently, the coloring composition 3 was applied on the glass substrate using a spin coater so that the chromaticity when using the F10 light source was x = 0.29. After drying at 70 ° C. for 20 minutes, an ultra high pressure mercury lamp was used to perform ultraviolet exposure with an integrated light amount of 150 mJ to prepare a color filter. Spectral transmittance was measured using a spectrophotometer ("U-3500" manufactured by Hitachi, Ltd.). The superiority or inferiority of the brightness was evaluated by the transmittance at 545 nm. The results are summarized in Table 10.

[Example 6, Comparative Examples 7 to 11]
The coloring agent 1 is a coloring agent 2, a comparative coloring agent 1, and Cyanine Blue A-13Y manufactured by Sanyo Dye Co., which is aluminum phthalocyanine, C.I. I. Pigment Blue 15: 6 (“Rionol BLUE E” manufactured by Toyo Ink Co., Ltd.), green pigment C.I. I. Pigment Green 36 (“Lionol Green 6YK” manufactured by Toyo Ink Co., Ltd.), or C.I. I. A colored composition 4 and comparative colored compositions 6 to 10 were obtained in the same manner as in Example 5 except that Pigment Green 58 (“A110” manufactured by DIC) was used. Evaluation was conducted in the same manner as in Example 5, and the results are summarized in Table 10.

  Coloring compositions 1 to 2 (Examples 3 to 6) using coloring agents 1 and 2 (Examples 1 and 2) containing siloxyaluminum phthalocyanine having an X-ray diffraction pattern by a specific CuKα ray of the present invention are as follows. Compared to comparative colored compositions 1 to 10 (Comparative Examples 2 to 11) containing μ-oxoaluminum phthalocyanine dimer (Comparative Example 1), aluminum phthalocyanine, copper phthalocyanine, halogenated copper phthalocyanine, or zinc halide phthalocyanine, 545 nm The color filter having a green segment containing the colorant of the present invention having a high transmittance was shown to have high brightness.

Claims (5)

A siloxyaluminum phthalocyanine compound represented by the following general formula (1) is refined by solvent salt milling, dry milling, or acid pasting, and an X-ray diffraction pattern by CuKα rays has a black angle 2θ (± 0.2). = 6.1 °, 8.0 °, 9.5 °, 10.7 °, 12.6 °, 13.6 °, 14.1 °, 14.8 °, 17.2 °, 18.3 ° Siloxyaluminum phthalocyanine pigments having peaks at 18.8 °, 19.2 °, 20.4 °, 22.1 °, 23.8 °, 24.6 °, 26.3 °, and 27.8 °. A color filter colorant.
General formula (1):

[In General Formula (1), R ¹ , R ² , and R ³ are each independently an aromatic group having 4 or less rings. Y and Z are each independently a hydrogen atom, an alkyl group which may have a substituent, an aryl group which may have a substituent, a cyano group, a nitro group, —COR ⁴ , —COOR ⁴ , or , -NR < ⁴ > R < ⁵ >. However, R ⁴ and R ⁵ each independently represent a hydrogen atom or an alkyl group which may have a substituent. Alternatively, R ⁴ and R ⁵ may be combined to form a heterocycle containing further nitrogen, oxygen or sulfur atoms. m is an integer of 0 to 16, n is an integer of 0 to 16, and m + n is an integer of 0 to 16. ] A siloxyaluminum phthalocyanine compound represented by the following general formula (1) and hydroxyaluminum phthalocyanine are refined by solvent salt milling, dry milling, or acid pasting, and an X-ray diffraction pattern by CuKα rays has a black angle 2θ. (± 0.2) = 6.0 °, 7.5 °, 8.4 °, 9.8 °, 13.1 °, 15.1 °, 16.3 °, 18.5 °, 20.2 °, 21.3 °, 22.8 °, and coloring agents for Luke color filter having a peak at 26.8 °.
General formula (1):

[In General Formula (1), R ¹ , R ² , and R ³ are each independently an aromatic group having 4 or less rings. Y and Z are each independently a hydrogen atom, an alkyl group which may have a substituent, an aryl group which may have a substituent, a cyano group, a nitro group, —COR ⁴ , —COOR ⁴ , or , -NR < ⁴ > R < ⁵ >. However, R ⁴ and R ⁵ each independently represent a hydrogen atom or an alkyl group which may have a substituent. Alternatively, R ⁴ and R ⁵ may be combined to form a heterocycle containing further nitrogen, oxygen or sulfur atoms. m is an integer of 0 to 16, n is an integer of 0 to 16, and m + n is an integer of 0 to 16. ]   The color filter colorant according to claim 1 or 2, further comprising a yellow pigment.   A coloring composition for a color filter, comprising the colorant for a color filter according to any one of claims 1 to 3, and a resin and / or a precursor of the resin. A color filter comprising a segment formed by using the color filter coloring composition according to claim 4.