JP2011057910A - Coloring composition, photosensitive coloring composition for color filter, and color filter - Google Patents

Abstract

<P>PROBLEM TO BE SOLVED: To provide a coloring composition excellent in heat resistance and light resistance, satisfying color density, color purity and transparency, containing no halogen atom or traces thereof, if contained, dealing with issues of safety and health, and environmental pollution; to provide a photosensitive coloring composition for color filters using the coloring composition, and a color filter. <P>SOLUTION: This coloring composition includes at least a resin (A), a colorant (B) containing an aluminum phthalocyanine pigment, and a pigment derivative (C) having a phthalocyanine structure as a parent skeleton. <P>COPYRIGHT: (C)2011,JPO&INPIT

Description

The present invention relates to a coloring composition, a photosensitive coloring composition for a color filter, and a color filter. The coloring composition of the present invention can be used as ink and paint, gravure ink, various general paints for automobile, wood, metal, etc., back coat paint for magnetic tape, radiation cure ink, ink for ink jet printer It can be used for applications such as color filter inks. Moreover, the photosensitive coloring composition for color filters of this invention can be used especially for the filter segment of the color filter for liquid crystal display devices, and for the filter segment of the color filter for solid-state image sensors.
Furthermore, the coloring composition of the present invention and the photosensitive coloring composition for a color filter do not contain a halogen atom or are contained in a very small amount. Useful for.

  In recent years, the development of environmentally friendly products with low environmental impact has been actively promoted, and more stringent standards have been set accordingly. Halogen atoms are one of the chemical substances that are desired to be removed as environmentally friendly products. Currently used green colorants such as prints and colorants are generally mixed colors of colorants centered on halogenated phthalocyanine represented by high chlorinated phthalocyanine green, which is not a problem with current standards. . It is no exaggeration to say that halogenated phthalocyanine pigments have a large amount of halogen atoms in the pigment structure, and that there is no green color that does not contain any halogen atoms in the pigment or pigment composition. Therefore, development of products that meet new standards is desired.

  Under these circumstances, a copper phthalocyanine blue pigment containing no halogen and a yellow high-grade pigment containing no halogen are mixed and co-dispersed to obtain the desired green hue and to have light resistance and heat resistance. Attempts have also been made, but the hue is unclear only by co-dispersion by simple color mixing, especially in tests when using ink and paint, "white blur" is a problem, only the pigment composition ratio and dispersion conditions Then, it is difficult to solve.

  Patent Document 1 discloses a pigment composition that maintains a clear hue, high light resistance, and high heat resistance by using a blue aluminum phthalocyanine pigment containing no halogen and a green pigment containing halogen. Yes.

  In addition, the color filter has two or more kinds of fine band (striped) filter segments arranged in parallel or intersecting with each other on the surface of a transparent substrate such as glass, or the fine filter segments are vertically and horizontally constant. It consists of things arranged in an array. The filter segments are as fine as several microns to several hundreds of microns, and are regularly arranged in a predetermined arrangement for each hue.

  On the color filter used in the color liquid crystal display device, a transparent electrode for driving the liquid crystal is generally formed by vapor deposition or sputtering, and an alignment film for aligning the liquid crystal in a certain direction is formed thereon. Has been. In order to sufficiently obtain the performance of these transparent electrodes and alignment films, it is necessary to perform the formation process at a high temperature of generally 200 ° C. or higher, preferably 230 ° C. or higher. For this reason, at present, as a method for producing a color filter, a method called a pigment dispersion method using a pigment having excellent light resistance and heat resistance as a colorant is mainly used.

  In recent years, the use of liquid crystal display devices has been extended to various monitors and TVs, and further improvement in color reproducibility has been demanded. In order to meet this demand, provision of a color filter with high color purity and high color density is expected.

  Patent Document 2 discloses a coloring composition for a green color filter segment. When an aluminum phthalocyanine pigment is used as a main pigment, high brightness can be obtained with high chromaticity even with a relatively small content, and color density, color purity, and transparency. A technology that balances the above is disclosed.

  However, conventionally used pigment compositions containing aluminum phthalocyanine pigments are difficult to maintain the pigment crystal system with respect to heat resistance at 200 ° C. or higher, preferably 230 ° C. or higher, which is required for color filter applications. There was a problem that the spectral shape changed. As a result, it is very difficult to obtain a color filter having excellent coloring power and lightness, and the tendency becomes more prominent as the area becomes lighter when a coating film is formed.

JP 2003-4930 A JP 2004-333817 A

The object of the present invention is excellent in heat resistance and light resistance, satisfying color density, color purity and transparency, and does not contain or contain halogen atoms corresponding to health and safety and environmental pollution problems. It is to provide a coloring composition which is very small.
Moreover, the further subject of this invention is providing the photosensitive coloring composition for color filters and color filter which used said coloring composition.

  The object is solved by a coloring composition containing at least a resin (A), a colorant (B) containing an aluminum phthalocyanine pigment, and a pigment derivative (C) having a phthalocyanine structure as a base skeleton.

The present invention also relates to the colored composition, wherein the pigment derivative (C) having a phthalocyanine structure as a base skeleton includes a pigment derivative represented by the following formula (1).
Equation (1) Pc-SO ₃ Y
(In Formula (1), Pc represents a phthalocyanine structure residue, and Y is any one of hydrogen, a 1-3 valent metal atom, an organic amine, or ammonia.)

  Further, the present invention relates to the colored composition further containing a pigment derivative (C2) having a phthalocyanine structure having a basic substituent as a base skeleton.

  Moreover, this invention relates to the said coloring composition in which resin (A) contains a thermosetting resin (A2).

  Moreover, this invention relates to the said coloring composition which contains a resin type pigment dispersant (D) further.

  Moreover, this invention relates to the photosensitive coloring composition for color filters which consists of the said coloring composition containing a photoinitiator (E) and / or a photopolymerizable composition (F) further.

  Moreover, this invention relates to the color filter which comprises the filter segment formed using the said photosensitive coloring composition for color filters.

The coloring composition of the present invention exhibits a clear color tone, a wide color display area, and a high coloring power. Thus, various general paints for gravure inks, automobiles, woods, metals, etc., magnetic tape backcoat paints, and radiations It can be provided for uses such as curing ink, ink for inkjet printers, and ink for color filters.
Further, the coloring composition of the present invention and the photosensitive coloring composition for a color filter do not contain a halogen atom or are contained in a very small amount. It is useful for applications.

Hereinafter, the present invention will be described in detail.
In the present application, the case where “(meth) acryloyl”, “(meth) acryl”, “(meth) acrylic acid”, “(meth) acrylate”, or “(meth) acrylamide” is particularly described. Unless otherwise indicated, “acryloyl and / or methacryloyl”, “acrylic and / or methacrylic”, “acrylic acid and / or methacrylic acid”, “acrylate and / or methacrylate”, or “acrylamide and / or methacrylamide”, respectively. It shall represent.

  The colored composition of the present invention comprises at least a resin (A), a colorant (B) containing an aluminum phthalocyanine pigment, and a pigment derivative (C) having a phthalocyanine structure as a base skeleton.

<Resin (A)>
Examples of the resin (A) contained in the colored composition of the present invention include conventionally known thermoplastic resins (A1) and thermosetting resins (A2).
Examples of the thermoplastic resin (A1) include acrylic resin, butyral resin, styrene-maleic acid copolymer, chlorinated polyethylene, chlorinated polypropylene, polyvinyl chloride, vinyl chloride-vinyl acetate copolymer, polyvinyl acetate, Examples include polyurethane resins, polyester resins, vinyl resins, alkyd resins, polystyrene resins, polyamide resins, rubber resins, cyclized rubber resins, celluloses, polyethylene (HDPE, LDPE), polybutadiene, and polyimide resins.

  When used as a photosensitive coloring composition for a color filter, the spectral transmittance is preferably 80% or more, more preferably 95% or more in the entire wavelength region of 400 to 700 nm in the visible light region. Moreover, when using with the form of an alkali image development type colored resist, it is preferable to use the alkali-soluble vinyl resin which copolymerized the acidic group containing ethylenically unsaturated monomer. In order to further improve the photosensitivity, an energy ray curable resin having an ethylenically unsaturated active double bond can also be used.

  Examples of the alkali-soluble resin obtained by copolymerizing an acidic group-containing ethylenically unsaturated monomer include resins having an acidic group such as a carboxyl group or a sulfone group. Specific examples of the alkali-soluble resin include an acrylic resin having an acidic group, an α-olefin / (anhydrous) maleic acid copolymer, a styrene / styrene sulfonic acid copolymer, an ethylene / (meth) acrylic acid copolymer, or Examples include isobutylene / (anhydrous) maleic acid copolymer. Among these, at least one resin selected from an acrylic resin having an acidic group and a styrene / styrene sulfonic acid copolymer, particularly an acrylic resin having an acidic group, is preferably used because of its high heat resistance and transparency.

  Energy ray curable resins having ethylenically unsaturated active double bonds include reactive substitution of isocyanate groups, aldehyde groups, epoxy groups, etc. on polymers having reactive substituents such as hydroxyl groups, carboxyl groups, amino groups, etc. A resin in which a photo-crosslinkable group such as a (meth) acryloyl group or a styryl group is introduced into the polymer by reacting a (meth) acrylic compound having a group or cinnamic acid is used. In addition, polymers containing acid anhydrides such as styrene-maleic anhydride copolymer and α-olefin-maleic anhydride copolymer are half-esterified with a (meth) acrylic compound having a hydroxyl group such as hydroxyalkyl (meth) acrylate. A modified version is also used.

  A thermoplastic resin (A1) having both alkali-soluble performance and energy ray curing performance is also preferable as the photosensitive coloring composition for color filters.

The following are mentioned as a monomer which comprises the said thermoplastic resin (A1). For example, methyl (meth) acrylate, ethyl (meth) acrylate, n-propyl (meth) acrylate, isopropyl (meth) acrylate, n-butyl (meth) acrylate, isobutyl (meth) acrylate, t-butyl (meth) acrylate, 2-ethylhexyl (meth) acrylate, cyclohexyl (meth) acrylate, stearyl (meth) acrylate, lauryl (meth) acrylate, tetrahydrofurfuryl (meth) acrylate, isobornyl (meth) acrylate, phenyl (meth) acrylate, benzyl (meth) Acrylate, phenoxyethyl (meth) acrylate, phenoxydiethylene glycol (meth) acrylate, methoxypolypropylene glycol (meth) acrylate, or ethoxypolyethylene Glycol (meth) acrylate of (meth) acrylates,
Alternatively, (meth) acrylamide (meth) acrylamide, N, N-dimethyl (meth) acrylamide, N, N-diethyl (meth) acrylamide, N-isopropyl (meth) acrylamide, diacetone (meth) acrylamide, acryloylmorpholine, etc. Acrylamides, styrenes, styrenes such as α-methylstyrene, ethyl vinyl ethers, n-propyl vinyl ethers, isopropyl vinyl ethers, n-butyl vinyl ethers, vinyl ethers such as isobutyl vinyl ethers, fatty acid vinyls such as vinyl acetate or vinyl propionate Kind.
Alternatively, cyclohexylmaleimide, phenylmaleimide, methylmaleimide, ethylmaleimide, 1,2-bismaleimide ethane 1,6-bismaleimidehexane, 3-maleimidopropionic acid, 6,7-methylenedioxy-4-methyl-3-maleimide Coumarin, 4,4′-bismaleimide diphenylmethane, bis (3-ethyl-5-methyl-4-maleimidophenyl) methane, N, N′-1,3-phenylenedimaleimide, N, N′-1,4- Phenylenedimaleimide, N- (1-pyrenyl) maleimide, N- (2,4,6-trichlorophenyl) maleimide, N- (4-aminophenyl) maleimide, N- (4-nitrophenyl) maleimide, N-benzyl Maleimide, N-bromomethyl-2,3-dichloromaleimide, N-succin Midyl-3-maleimidobenzoate, N-succinimidyl-3-maleimidopropionate, N-succinimidyl-4-maleimidobutyrate, N-succinimidyl-6-maleimidohexanoate, N- [4- (2-benzimidazolyl) phenyl N-substituted maleimides such as maleimide and 9-maleimide acridine.

  In particular, it is preferable to have a structural unit derived from an N-substituted maleimide, and among them, cyclohexylmaleimide, methylmaleimide, ethylmaleimide, and 1,2-bismaleimideethane are preferable, and cyclohexylmaleimide is particularly preferable.

（式（２）中、Ｒ₂₁〜Ｒ₂₄はそれぞれ独立に、ＣＨ₂ＯＣＨ₃、ＣＨ₂ＯＣ₄Ｈ₉、ＨまたはＣＨ₂ＯＨである。） Examples of the thermosetting resin (A2) include epoxy resins, benzoguanamine resins, rosin-modified maleic acid resins, rosin-modified fumaric acid resins, melamine resins, urea resins, and phenol resins.
The colored composition of the present invention preferably includes a thermosetting resin (A2) in terms of heat resistance. For example, an epoxy resin and a melamine resin can be more preferably used, and a melamine resin is particularly preferable. Especially, the melamine compound which has the methylol imino group represented by following formula (2), or its condensate is further more preferable.
Formula (2)

(In the formula (2), R _{21 to} R ₂₄ are each independently CH ₂ OCH ₃ , CH ₂ OC ₄ H ₉ , H or CH ₂ OH.)

  The thermosetting resin (A2) is preferably added in the range of 10 to 60 parts by weight with respect to 100 parts by weight of the colorant (B). If the amount is less than 10 parts by weight, the effect of improving heat resistance and light resistance is reduced, and if it exceeds 60 parts by weight, the developability deteriorates during alkali development, which is not preferable.

The weight average molecular weight (Mw) of the resin (A) is preferably in the range of 10,000 to 100,000, more preferably in the range of 30,000 to 80,000, in order to disperse the colorant (B) preferably. It is. The number average molecular weight (Mn) is preferably in the range of 5,000 to 50,000, and the value of Mw / Mn is preferably 10 or less.
Here, the weight average molecular weight (Mw) and the number average molecular weight (Mn) are connected to four separation columns in series in the gel permeation chromatography “HLC-8120GPC” manufactured by Tosoh Corporation. This is a polystyrene equivalent molecular weight measured using “TSK-GEL SUPER H5000”, “H4000”, “H3000”, and “H2000” manufactured by the company and using tetrahydrofuran as the mobile phase.

  When the resin (A) is used as a photosensitive coloring composition for a color filter, from the viewpoint of pigment dispersibility, developability, and heat resistance, a carboxyl group that functions as a pigment adsorbing group and an alkali-soluble group during development; The balance of aliphatic groups and aromatic groups that act as affinity groups for the pigment carrier and solvent is important for pigment dispersibility, developability, and durability, and a resin having an acid value of 20 to 300 mgKOH / g should be used. preferable. When the acid value is less than 20 mgKOH / g, the solubility in the developing solution is poor and it is difficult to form a fine pattern. When it exceeds 300 mgKOH / g, no fine pattern remains.

  The resin (A) can be used in an amount of 30 to 500% by weight based on the total weight of the colorant (B). If it is less than 30% by weight, the film formability and various resistances are insufficient, and if it exceeds 500% by weight, the pigment concentration is low and color characteristics cannot be expressed.

（式（３）中、Ｘは、ヒドロキシル基、水素原子、塩素原子、臭素原子のいずれかを表す。また、Ｒ¹¹〜Ｒ¹⁴はそれぞれ独立に、ハロゲン原子または炭素数１〜４のアルキル基を表し、互いに同一でも異なっていてもよい。ｎ１１〜ｎ１４はそれぞれ独立に０〜４の整数である。）
なかでも、下記式（４）の構造を有するものが、有機溶剤中への分散が容易となるため好ましい。
また、さらにハロゲン原子を無くす意味でも好ましい。
式（４）

アルミニウムフタロシアニン顔料は、着色組成物の全量を基準として、５〜２０重量％が好ましい。 <Colorant (B) containing aluminum phthalocyanine pigment>
The coloring composition of the present invention contains a colorant (B) containing an aluminum phthalocyanine pigment. As the aluminum phthalocyanine pigment, those having the structure of the following formula (3) can be used.
Formula (3)

(In Formula (3), X represents any of a hydroxyl group, a hydrogen atom, a chlorine atom, and a bromine atom. Moreover, R < ¹¹ > -R < ¹⁴ > is respectively independently a halogen atom or a C1-C4 alkyl group. And n11 to n14 are each independently an integer of 0 to 4.)
Among these, those having the structure of the following formula (4) are preferable because they can be easily dispersed in an organic solvent.
Further, it is also preferable in the sense of eliminating halogen atoms.
Formula (4)

The aluminum phthalocyanine pigment is preferably 5 to 20% by weight based on the total amount of the coloring composition.

The coloring composition of the present invention may further contain a pigment as long as the effect of the present invention is not impaired, for example, in order to adjust the chromaticity.
Specific examples of pigments that can be used are shown by pigment numbers. The following “CI” means a color index (CI).

When the coloring composition of the present invention is used as a blue coloring composition, C.I. I. Pigment Blue 15, 15: 1, 15: 2, 15: 3, 15: 4, 15: 6, 16, 22, 60, 64 and the like can be used in combination. Furthermore, a purple pigment can be used in combination with the blue coloring composition.
Examples of purple pigments added to the blue coloring composition include C.I. I. Pigment Violet 1, 19, 23, 27, 29, 30, 32, 37, 40, 42, 50, etc. can be used. Especially, C.I. I. Pigment Violet 23 is preferable.

When a blue pigment is used in combination, the weight ratio of blue pigment / aluminum phthalocyanine pigment is preferably 90/10 to 10/90.
If the weight ratio of the aluminum phthalocyanine pigment is 90% by weight or more, the hue as blue does not appear, and if it is 10% by weight or less, the film becomes thicker if the desired chromaticity is attempted to be obtained.
When a purple pigment is used in combination, the weight ratio of purple pigment / aluminum phthalocyanine pigment is preferably 95/5 to 10/90. When the weight ratio of the aluminum phthalocyanine pigment is 90% by weight or more, the lightness of blue is low, and when it is 5% by weight or less, the hue of blue is not appropriate.

When the coloring composition of the present invention is used as a green coloring composition, C.I. I. Pigment Green 7, 10, 36, 37, 58 or the like can be used in combination. Furthermore, a yellow pigment can be used in combination with the green coloring composition.
Examples of the yellow pigment added to the green coloring composition include 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 Or the like can be used 5,176,177,179,180,181,182,185,187,188,193,194,199. Especially, C.I. I. Pigment Yellow 138, 139, 150, and 185 are preferable.

When the pigment composition is used for green and the green pigment is used in combination, the weight ratio of green pigment / aluminum phthalocyanine pigment is preferably 70/30 to 95/5. When the weight ratio of the aluminum phthalocyanine pigment is 30% by weight or more, the lightness is low as green, and when it is 5% by weight or less, the amount of the aluminum phthalocyanine pigment having good coloring power is reduced, and when the desired chromaticity is attempted, the film becomes thicker. This is not preferable.
When a yellow pigment is used in combination, the weight ratio of yellow pigment / aluminum phthalocyanine pigment is preferably 60/40 to 80/20. When the weight ratio of the aluminum phthalocyanine pigment is 40% by weight or more, the lightness is low as green, and when it is 20% by weight or less, the hue as green does not appear.

<Miniaturization of pigment>
The pigment used in the colored composition of the present invention is preferably a finely processed pigment that has been subjected to salt milling.

  Salt milling is a process in which a mixture of pigment, water-soluble inorganic salt and water-soluble organic solvent is heated using a kneader such as a kneader, two-roll mill, three-roll mill, ball mill, attritor, or sand mill. After kneading, the water-soluble inorganic salt and the water-soluble organic solvent are removed by washing with water. The water-soluble inorganic salt works as a crushing aid, and it is thought that the pigment is crushed using the high hardness of the inorganic salt during salt milling, thereby generating an active surface and causing crystal growth. Yes. Therefore, the crushing of the pigment and the crystal growth occur simultaneously during the kneading, and the primary particle diameter of the pigment obtained varies depending on the kneading conditions.

  In order to promote crystal growth by heating, the heating temperature is preferably 40 to 150 ° C. When the heating temperature is less than 40 ° C., crystal growth does not occur sufficiently, and the shape of the pigment particles becomes close to amorphous, which is not preferable. On the other hand, when the heating temperature exceeds 150 ° C., crystal growth proceeds excessively and the primary particle diameter of the pigment becomes large, which is not preferable as a colorant for the color filter coloring composition. The kneading time for the salt milling treatment is preferably 2 to 24 hours from the viewpoint of the balance between the particle size distribution of the primary particles of the salt milling treatment pigment and the cost required for the salt milling treatment.

  By optimizing the conditions for salt milling the pigment, it is possible to obtain a pigment having a sharp particle size distribution in which the primary particle diameter is very fine and the distribution range is wide. It is preferable that the primary particle diameter calculated | required by TEM (transmission electron microscope) of the pigment used for the coloring composition of this invention is the range of 20-100 nm. When it becomes smaller than 20 nm, dispersion in an organic solvent becomes difficult. On the other hand, if it exceeds 100 nm, a sufficient contrast ratio cannot be obtained. A particularly preferable range is 25 to 85 nm.

  As the water-soluble inorganic salt used for the salt milling treatment, sodium chloride, barium chloride, potassium chloride, sodium sulfate and the like can be used, but sodium chloride (salt) is preferably used from the viewpoint of cost. The water-soluble inorganic salt is preferably used in an amount of 50 to 2000% by weight, and most preferably 300 to 1000% by weight, based on the total amount of pigment, from the viewpoint of both processing efficiency and production efficiency.

  The water-soluble organic solvent is not particularly limited as long as it functions to wet the pigment and the water-soluble inorganic salt and dissolves (mixes) in water and does not substantially dissolve the inorganic salt to be used. However, a high boiling point solvent having a boiling point of 120 ° C. or higher is preferable from the viewpoint of safety because the temperature rises during salt milling and the solvent is easily evaporated.

  For example, 2-methoxyethanol, 2-butoxyethanol, 2- (isopentyloxy) ethanol, 2- (hexyloxy) ethanol, diethylene glycol, diethylene glycol monoethyl ether, diethylene glycol monobutyl ether, triethylene glycol, triethylene glycol monomethyl ether, Liquid polyethylene glycol, 1-methoxy-2-propanol, 1-ethoxy-2-propanol, dipropylene glycol, dipropylene glycol monomethyl ether, dipropylene glycol monoethyl ether, liquid polypropylene glycol and the like are used. The water-soluble organic solvent is preferably used in an amount of 5 to 1000 parts by weight, and most preferably 50 to 500 parts by weight, based on 100 parts by weight of the pigment.

  When performing the salt milling treatment, a resin may be added as necessary. The type of resin used is not particularly limited, and natural resins, modified natural resins, synthetic resins, synthetic resins modified with natural resins, and the like can be used. The resin used is solid at room temperature, preferably insoluble in water, and more preferably partially soluble in the organic solvent. The amount of the resin used is preferably in the range of 5 to 200 parts by weight with respect to 100 parts by weight of the pigment.

Further, the volume average primary particle diameter (MV) of the pigment is measured by measuring the short axis diameter and the long axis diameter of 100 primary particles of the pigment using a transmission electron microscope (TEM) photograph. The average of the shaft diameters is defined as the particle diameter (d) of the pigment particles, and then the volume (V) of each particle is determined assuming that each pigment is a sphere having the determined particle diameter. And calculated using the following formula (5).
Formula (5) MV = Σ (V · d) / Σ (V)

<Pigment derivative (C) having phthalocyanine structure as base matrix>
The coloring composition of the present invention contains a pigment derivative (C) having a phthalocyanine structure as a base skeleton.
The phthalocyanine structure is a metal phthalocyanine having a central metal or a metal-free phthalocyanine, and can be produced by a known method. Using phthalocyanine with copper, zinc, nickel, aluminum or cobalt as the central metal, or metal-free phthalocyanine, it is a particularly vivid and highly useful derivative as a colorant, but it has the effects of heat resistance and light resistance. Therefore, it is preferable to use a copper phthalocyanine structure as a base skeleton.
The pigment derivative (C) having a phthalocyanine structure as a base skeleton may have an acidic substituent (C1), a basic substituent (C2), or a substituent having such a phthalocyanine structure as a base skeleton. Examples thereof include compounds having a phthalimidomethyl group introduced.
Among them, the derivative (C1) having an acidic substituent is more excellent from the viewpoints of heat resistance and light resistance. These may be used alone or in combination of two or more.

<Pigment derivative (C1) having a phthalocyanine structure having an acidic substituent as a base skeleton>
As the pigment derivative (C1) having a phthalocyanine structure having an acidic functional group as a base skeleton, derivatives represented by the following formula (6), the following formula (7), and the following formula (8) can be used. As the derivative having an acidic functional group, any of a derivative not having a counter ion represented by the following formula (6) and a derivative having a counter ion represented by the following formulas (7) and (8) should be used. Can do.

Formula (6): Pc-Z1
(In Formula (6), Pc represents a phthalocyanine structure residue, and Z1 is a sulfonic acid group or a carboxyl group.)

Formula (7): (Pc-Z2) [N ⁺ (R5, R6, R7, R8)]
(In formula (7), Pc represents a phthalocyanine pigment skeleton, R5 is an alkyl group having 5 to 20 carbon atoms, and R6, R7, and R8 are each independently a hydrogen atom or 1 to 20 carbon atoms. an alkyl group, Z2 is, SO ₃ ^- or COO ^- and is).

Formula (8): (Pc-Z2) x My ⁺
(In formula (8), Pc represents a phthalocyanine pigment skeleton, and My ⁺ represents a metal ion such as lithium, sodium, potassium, magnesium, calcium, barium, iron, cobalt, nickel, copper, zinc, or aluminum. An ion, y is a valence of the ion, x is a value obtained by an equation x = y ÷ (number of Z2), and Z2 is SO ₃ ⁻ or COO ⁻ .)

    Z1 in the formula (6) may be present in the range of 0.5 to 8.0, preferably 0.7 to 3.0, with respect to Pc in the formula (6).

Z2 of Formula (7) may exist in the range of 0.5 to 8.0, preferably 0.7 to 3.0, with respect to Pc of Formula (7). At the same time, the same number of [N ⁺ ((R5, R6, R7, R8)] may exist depending on the number of Z2.

    Z2 of Formula (8) may exist in the range of 0.5 to 8.0, preferably 0.7 to 3.0, with respect to Pc of Formula (8). At the same time, the number of x may be appropriately changed in accordance with the number of Z2 and the ionic valence y of M.

Among the derivatives having an acidic substituent, the derivative having an acidic substituent represented by the following formula (1) is particularly excellent from the viewpoints of heat resistance and light resistance.
Equation (1) Pc-SO ₃ Y
(In Formula (1), Pc represents a phthalocyanine structure residue, and Y is any one of hydrogen, a 1-3 valent metal atom, an organic amine, or ammonia.)

Examples of 1 to 3 metal atoms include lithium, potassium, sodium, calcium, magnesium, strontium, aluminum,
Examples of the organic amine include monoalkylamines such as ethylamine and butylamine, dialkylamines such as dimethylamine and diethylamine, trialkylamine monoethanolamines such as trimethylamine and triethylamine, and alkanolamines such as diethanolamine and triethanolamine.

<Pigment derivative (C2) having a phthalocyanine structure having a basic substituent as a base skeleton>
The pigment derivative (C2) having a base skeleton having a phthalocyanine structure having a basic substituent is represented by the following formula.

Formula (9): Pc-Lm
(In Formula (9), Pc is a phthalocyanine structure residue,
m is an integer of 1 to 4,
L is a substituent selected from the group represented by formulas (10), (11), and (12). )

Formula (10)

Formula (11):

Formula (12):

(In the formulas (10) to (12),
X _{is, -SO 2 -, - CO -} , - CH 2 -, - CH 2 NHCOCH 2 -, - CH 2 NHSO 2 CH 2 -, or a direct bond,
Y is —NH—, —O—, or a direct bond;
n is an integer of 1 to 10,
Y ¹ is —NH—, —NR ⁵⁸ —Z—NR ⁵⁹ —, or a direct bond;
R ⁵⁸ and R ⁵⁹ are each independently a hydrogen bond, an optionally substituted alkyl group having 1 to 36 carbon atoms, an optionally substituted alkenyl group having 2 to 36 carbon atoms, or A phenyl group which may have a substituent,
Z is an alkylene group which may have a substituent, or an arylene group which may have a substituent,
R ⁵⁰ and R ⁵¹ are each independently a hydrogen atom, an optionally substituted alkyl group having 1 to 30 carbon atoms, an optionally substituted alkenyl group having 2 to 30 carbon atoms, or R ⁵⁰ and R ⁵¹ together are a heterocyclic ring which may further have a substituent containing a further nitrogen, oxygen or sulfur atom,
R ⁵² , R ⁵³ , R ⁵⁴ , and R ⁵⁵ are each independently a hydrogen atom, an alkyl group having 1 to 20 carbon atoms that may have a substituent, or 2 to carbon atoms that may have a substituent. 20 alkenyl group, an arylene group having 6 to 20 carbon atoms which may have a substituent,
R ⁵⁶ is a hydrogen atom, an optionally substituted alkyl group having 1 to 20 carbon atoms, an optionally substituted alkenyl group having 2 to 20 carbon atoms,
R ⁵⁷ is a substituent represented by the above formula (10) or a substituent represented by the above formula (11),
Q is a hydroxyl group, an alkoxyl group, a substituent represented by the above formula (10), or a substituent represented by the above formula (11). )

  Examples of the amine component used to form the substituents represented by the formulas (10) to (12) include dimethylamine, diethylamine, methylethylamine, N, N-ethylisopropylamine, N, N-ethylpropyl. Amine, N, N-methylbutylamine, N, N-methylisobutylamine, N, N-butylethylamine, N, N-tert-butylethylamine, diisopropylamine, dipropylamine, N, N-sec-butylpropylamine, Dibutylamine, di-sec-butylamine, diisobutylamine, N, N-isobutyl-sec-butylamine, diamylamine, diisoamylamine, dihexylamine, dicyclohexylamine, di (2-ethylhexyl) amine, dioctylamine, N, N -Methyloctadeci Amine, didecylamine, diallylamine, N, N-ethyl-1,2-dimethylpropylamine, N, N-methylhexylamine, dioleylamine, distearylamine, N, N-dimethylaminomethylamine, N, N-dimethylamino Ethylamine, N, N-dimethylaminoamylamine, N, N-dimethylaminobutylamine, N, N-diethylaminoethylamine, N, N-diethylaminopropylamine, N, N-diethylaminohexylamine, N, N-diethylaminobutylamine, N , N-diethylaminopentylamine, N, N-dipropylaminobutylamine, N, N-dibutylaminopropylamine, N, N-dibutylaminoethylamine, N, N-dibutylaminobutylamine, N, N-diisobutylaminopen Ruamine, N, N-methyl-laurylaminopropylamine, N, N-ethylhexylaminoethylamine, N, N-distearylaminoethylamine, N, N-dioleylaminoethylamine, N, N-distearylaminobutylamine, Piperidine, 2-Pipecoline, 3-Pipecoline, 4-Pipecoline, 2,4-Lupetidine, 2,6-Lupetidine, 3,5-Lupetidine, 3-Piperidinmethanol, Pipecolic acid, Isonipecotic acid, Methyl isonipecotate, Isonipecotic acid Ethyl, 2-piperidineethanol, pyrrolidine, 3-hydroxypyrrolidine, N-aminoethylpiperidine, N-aminoethyl-4-pipecholine, N-aminoethylmorpholine, N-aminopropylpiperidine, N-aminopropyl-2-pipecholine, -Aminopropyl-4-pipecholine, N-aminopropylmorpholine, N-methylpiperazine, N-butylpiperazine, N-methylhomopiperazine, 1-cyclopentylpiperazine, 1-amino-4-methylpiperazine, 1-cyclopentylpiperazine, etc. Can be mentioned.

Specific examples of the pigment derivative (C2) having a phthalocyanine structure having a basic substituent as a base skeleton of the present invention are shown below with compound numbers, but are not limited thereto.

〔式（１３）中、ＣｕＰｃは、銅フタロシアニン構造残基である。〕 ・ Compound 1
Formula (13):

[In Formula (13), CuPc is a copper phthalocyanine structure residue. ]

〔式（１４）中、ＣｕＰｃは、銅フタロシアニン構造残基である。〕 ・ Compound 2
Formula (14):

[In Formula (14), CuPc is a copper phthalocyanine structure residue. ]

  In the pigment composition of the present invention, the amount of the pigment derivative (C) having a phthalocyanine structure as a base skeleton is preferably 1 to 50% by weight, more preferably 3 to 30% by weight, based on the weight of the pigment. Most preferably, it is 5 to 25% by weight. When the pigment derivative is less than 1% by weight, it is difficult to obtain the added effect, and when it exceeds 50% by weight, the heat resistance and light resistance may be deteriorated.

  The colored composition of the present invention is a combination of a derivative having an acidic substituent represented by the formula (1) and a pigment derivative (C2) having a phthalocyanine structure having a basic substituent as a base skeleton, In particular, a colored composition containing an aluminum phthalocyanine pigment having excellent heat resistance and light resistance can be obtained.

<Pigment dispersant>
Examples of the pigment dispersant that can be used in combination with the pigment derivative in the colored composition of the present invention include a resin-type pigment dispersant (D) and a surfactant.

  The resin-type pigment dispersant (D) used as a pigment dispersant has a pigment affinity part having a property of adsorbing to the pigment and a part compatible with the pigment carrier, and is adsorbed to the pigment to be a pigment of the pigment. It serves to stabilize dispersion in the carrier. Specific examples of resin-type pigment dispersants include polycarboxylic acid esters such as polyurethane and polyacrylate, unsaturated polyamides, polycarboxylic acids, polycarboxylic acid (partial) amine salts, polycarboxylic acid ammonium salts, and polycarboxylic acid alkylamines. Salts, polysiloxanes, long-chain polyaminoamide phosphates, hydroxyl group-containing polycarboxylic acid esters, their modified products, amides formed by the reaction of poly (lower alkyleneimines) with polyesters having free carboxyl groups, and the like Oil-based dispersants such as salts; water-soluble such as (meth) acrylic acid-styrene copolymer, (meth) acrylic acid- (meth) acrylic acid ester copolymer, styrene-maleic acid copolymer, polyvinyl alcohol, polyvinylpyrrolidone Resin, water-soluble polymer, polyester Modified polyacrylate, ethylene oxide / propylene oxide addition compound, phosphate ester-based or the like is used. These can be used alone or in admixture of two or more.

  As the resin-type dispersant, polyacrylate is preferable from the viewpoint of heat resistance, and polycarboxylic acid ester or unsaturated polyamide is particularly preferable.

  Surfactants used as pigment dispersants include polyoxyethylene alkyl ether sulfate, sodium dodecylbenzene sulfonate, alkali salt of styrene-acrylic acid copolymer, sodium stearate, sodium alkyl naphthalene sulfonate, alkyl diphenyl ether disulfone. Sodium acetate, monoethanolamine dodecyl sulfate, triethanolamine dodecyl sulfate, ammonium dodecyl sulfate, monoethanolamine stearate, sodium stearate, sodium dodecyl sulfate, monoethanolamine of styrene-acrylic acid copolymer, polyoxyethylene alkyl ether phosphorus Anionic surfactants such as acid esters; polyoxyethylene oleyl ether, polyoxyethylene dodecyl ether, polyoxy Nonionic surfactants such as tylene nonyl phenyl ether, polyoxyethylene alkyl ether phosphate ester, polyoxyethylene sorbitan monostearate, polyethylene glycol monolaurate; chaotics such as alkyl quaternary ammonium salts and their ethylene oxide adducts Examples include amphoteric surfactants such as alkylbetaines such as alkyldimethylaminoacetic acid betaines and alkylimidazolines, and these can be used alone or in admixture of two or more.

<Organic solvent>
Furthermore, in the coloring composition of the present invention, a pigment is sufficiently dispersed in a pigment carrier and applied on a transparent substrate such as a glass substrate so as to have a dry film thickness of 0.2 to 5 μm to form a filter segment. A solvent can be included to facilitate the process.
Examples of the solvent include 1,2,3-trichloropropane, 1,3-butanediol, 1,3-butylene glycol, 1,3-butylene glycol diacetate, 1,4-dioxane, 2-heptanone, and 2-methyl. -1,3-propanediol, 3,5,5-trimethyl-2-cyclohexen-1-one, 3,3,5-trimethylcyclohexanone, ethyl 3-ethoxypropionate, 3-methyl-1,3-butanediol 3-methoxy-3-methyl-1-butanol, 3-methoxy-3-methylbutyl acetate, 3-methoxybutanol, 3-methoxybutyl acetate, 4-heptanone, m-xylene, m-diethylbenzene, m-dichlorobenzene N, N-dimethylacetamide, N, N-dimethylformamide, n-butyl alcohol, n-butylbenzene, n-propyl acetate, N-methylpyrrolidone, o- Xylene, o-chlorotoluene, o-diethylbenzene, o-dichlorobenzene, p-chlorotoluene, p-diethylbenzene, sec-butylbenzene, tert-butylbenzene, γ-butyrolactone, isobutyl alcohol, isophorone, ethylene glycol diethyl ether, ethylene Glycol dibutyl ether, ethylene glycol monoisopropyl ether, ethylene glycol monoethyl ether, ethylene glycol monoethyl ether acetate, ethylene glycol monotertiary butyl ether, ethylene glycol monobutyl ether, ethylene glycol monobutyl ether acetate, ethylene glycol monopropyl ether, ethylene glycol mono Hexyl ether, ethylene glycol monomethyl ether Ter, ethylene glycol monomethyl ether acetate, diisobutyl ketone, diethylene glycol diethyl ether, diethylene glycol dimethyl ether, diethylene glycol monoisopropyl ether, diethylene glycol monoethyl ether acetate, diethylene glycol monobutyl ether, diethylene glycol monobutyl ether acetate, diethylene glycol monomethyl ether, cyclohexanol, cyclohexanol acetate, cyclohexanone , Dipropylene glycol dimethyl ether, dipropylene glycol methyl ether acetate, dipropylene glycol monoethyl ether, dipropylene glycol monobutyl ether, dipropylene glycol monopropyl ether, dip Pyrene glycol monomethyl ether, diacetone alcohol, triacetin, tripropylene glycol monobutyl ether, tripropylene glycol monomethyl ether, propylene glycol diacetate, propylene glycol phenyl ether, propylene glycol monoethyl ether, propylene glycol monoethyl ether acetate, propylene glycol monobutyl ether , Propylene glycol monopropyl ether, propylene glycol monomethyl ether, propylene glycol monomethyl ether acetate, propylene glycol monomethyl ether propionate, benzyl alcohol, methyl isobutyl ketone, methyl cyclohexanol, n-amyl acetate, n-butyl acetate, isoamyl acetate, Isobutyl, propyl acetate, include dibasic acid esters such as, used alone or in combination.

<Photosensitive coloring composition for color filter>
The colored composition of the present invention can be used as a photosensitive colored composition for a color filter by further adding a photopolymerization initiator (E) and / or a photopolymerizable composition (F).
<Photopolymerization initiator (E)>
When the composition is cured by ultraviolet irradiation or a filter segment is formed by a photolithographic method, a photopolymerization initiator (E) or the like is added to the photosensitive coloring composition for a color filter of the present invention. The blending amount when using the photopolymerization initiator (E) is preferably 5 to 200% by weight based on the total amount of the pigment, and 10 to 150% by weight from the viewpoint of photocurability and developability. It is more preferable.

As the photopolymerization initiator (E),
4-phenoxydichloroacetophenone, 4-t-butyl-dichloroacetophenone, diethoxyacetophenone, 1- (4-isopropylphenyl) -2-hydroxy-2-methylpropan-1-one, 1-hydroxycyclohexyl phenyl ketone, 2- Such as benzyl-2-dimethylamino-1- (4-morpholinophenyl) -butan-1-one and 2-methyl-1- [4- (methylthio) phenyl] -2-morpholinopropan-1-one An acetophenone photopolymerization initiator;
Benzoin photopolymerization initiators such as benzoin, benzoin methyl ether, benzoin ethyl ether, benzoin isopropyl ether, and benzyldimethyl ketal;
Benzophenone-based photopolymerization initiators such as benzophenone, benzoylbenzoic acid, methyl benzoylbenzoate, 4-phenylbenzophenone, hydroxybenzophenone, acrylated benzophenone, and 4-benzoyl-4′-methyldiphenyl sulfide;
Thioxanthone photopolymerization initiators such as thioxanthone, 2-chlorothioxanthone, 2-methylthioxanthone, isopropylthioxanthone, and 2,4-diisopropylthioxanthone;
2,4,6-trichloro-s-triazine, 2-phenyl-4,6-bis (trichloromethyl) -s-triazine, 2- (p-methoxyphenyl) -4,6-bis (trichloromethyl) -s -Triazine, 2- (p-tolyl) -4,6-bis (trichloromethyl) -s-triazine, 2-piperonyl-4,6-bis (trichloromethyl) -s-triazine, 2,4-bis (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 photopolymerization initiators such as triazine;
A borate photopolymerization initiator; a carbazole photopolymerization initiator; an imidazole photopolymerization initiator; and an oxime ester photopolymerization initiator are used.

The above photopolymerization initiators are used alone or in combination of two or more, but as a sensitizer,
α-acyloxy ester, acylphosphine oxide, methylphenylglyoxylate, benzyl, 9,10-phenanthrenequinone, camphorquinone, ethylanthraquinone, 4,4′-diethylisophthalophenone, 3,3 ′, Compounds such as 4,4′-tetra (t-butylperoxycarbonyl) benzophenone and 4,4′-diethylaminobenzophenone can also be used in combination.

  The blending amount when using the sensitizer is preferably 3 to 60% by weight based on the photopolymerization initiator (E) contained in the colored composition, from the viewpoint of photocurability and developability. More preferably, it is 5 to 50% by weight.

<Photopolymerizable composition (F)>
As monomers and oligomers used as the photopolymerizable composition (F),
Methyl (meth) acrylate, ethyl (meth) acrylate, 2-hydroxyethyl (meth) acrylate, 2-hydroxypropyl (meth) acrylate, cyclohexyl (meth) acrylate, β-carboxyethyl (meth) acrylate, and tricyclodecanyl Monofunctional (meth) acrylates such as (meth) acrylate;
Bifunctional (meth) acrylates such as polyethylene glycol di (meth) acrylate, 1,6-hexanediol di (meth) acrylate, triethylene glycol di (meth) acrylate, and tripropylene glycol di (meth) acrylate;
Trifunctional or more polyfunctional compounds such as trimethylolpropane tri (meth) acrylate, pentaerythritol tri (meth) acrylate, pentaerythritol tetra (meth) acrylate, dipentaerythritol hexa (meth) acrylate, and dipentaerythritol penta (meth) acrylate Functional (meth) acrylate;
1,6-hexanediol diglycidyl ether, bisphenol A diglycidyl ether, neopentyl glycol diglycidyl ether, and epoxy (meth) acrylate which is a reaction product of an epoxy compound such as phenol novolac resin and (meth) acrylic acid;
Various (meth) acrylic acid esters modified with polyester, polyurethane, isocyanurate, methylolated melamine, etc .; and (meth) acrylic acid, styrene, vinyl acetate, hydroxyethyl vinyl ether, ethylene glycol divinyl ether, pentaerythritol trivinyl ether, ( Examples include monomers other than (meth) acrylates such as (meth) acrylamide, N-hydroxymethyl (meth) acrylamide, N-vinylformamide, and acrylonitrile, and these can be used alone or in combination of two or more. However, it is not necessarily limited to these.

<Leveling agent>
In order to improve the leveling property of the composition on the transparent substrate, it is preferable to add a leveling agent to the colored composition of the present invention. As the leveling agent, dimethylsiloxane having a polyether structure or a polyester structure in the main chain is preferable. Specific examples of dimethylsiloxane having a polyether structure in the main chain include FZ-2122 manufactured by Toray Dow Corning, BYK-333 manufactured by Big Chemie. Specific examples of dimethylsiloxane having a polyester structure in the main chain include BYK-310 and BYK-370 manufactured by BYK Chemie. Dimethylsiloxane having a polyether structure in the main chain and dimethylsiloxane having a polyester structure in the main chain can be used in combination. The content of the leveling agent is usually 0.003 to 0.5% by weight based on the total weight (100% by weight) of the coloring composition.

<Other ingredients>
The colored composition of the present invention can contain a storage stabilizer in order to stabilize the viscosity of the composition over time. Moreover, in order to improve adhesiveness with a transparent substrate, adhesion improving agents, such as a silane coupling agent, can also be contained.
Examples of storage stabilizers include quaternary ammonium chlorides such as benzyltrimethyl chloride and diethylhydroxyamine, organic acids such as lactic acid and oxalic acid, and organic acids such as methyl ether, t-butylpyrocatechol, tetraethylphosphine, and tetraphenylphosphine. Examples thereof include phosphine and phosphite. The storage stabilizer can be used in an amount of 0.1 to 10 parts by weight with respect to 100 parts by weight of the colorant (B) in the coloring composition.

  Examples of the silane coupling agent include vinyl silanes such as vinyltris (β-methoxyethoxy) silane, vinylethoxysilane, and vinyltrimethoxysilane, (meth) acrylsilanes such as γ-methacryloxypropyltrimethoxysilane, β- (3 , 4-epoxycyclohexyl) ethyltrimethoxysilane, β- (3,4-epoxycyclohexyl) methyltrimethoxysilane, β- (3,4-epoxycyclohexyl) ethyltriethoxysilane, β- (3,4-epoxycyclohexyl) ) Epoxysilanes such as methyltriethoxysilane, γ-glycidoxypropyltrimethoxysilane, γ-glycidoxypropyltriethoxysilane, N-β (aminoethyl) γ-aminopropyltrimethoxysilane, N-β ( Aminoethyl) γ-aminopro Lutriethoxysilane, N-β (aminoethyl) γ-aminopropylmethyldiethoxysilane, γ-aminopropyltriethoxysilane, γ-aminopropyltrimethoxysilane, N-phenyl-γ-aminopropyltrimethoxysilane, N Examples include aminosilanes such as -phenyl-γ-aminopropyltriethoxysilane, 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 colorant (B) in the coloring composition.

<Method for producing colored composition>
The colored composition of the present invention comprises a resin (A), a colorant (B) containing an aluminum phthalocyanine pigment, a pigment derivative (C) having a phthalocyanine structure as a base skeleton, and, if necessary, other pigment dispersants In addition, a mixture of solvents can be produced by finely dispersing the pigment in a resin solvent liquid using various dispersing means such as a three roll mill, a two roll mill, a sand mill, a kneader, or an attritor (pigment dispersion). body). When used as a photosensitive coloring composition for a color filter, it can be prepared as a photosensitive coloring composition for a solvent developing type or alkali developing type color filter. The coloring composition for a solvent developing type or alkali developing type color filter comprises the above-mentioned pigment dispersion, a photopolymerizable composition (F), a photopolymerization initiator (E), and other resins, solvents, and pigment dispersions as required. An agent, an additive, etc. can be mixed and adjusted.
Moreover, the coloring composition containing 2 or more types of pigments can also be produced by mixing each pigment separately and finely dispersed in a resin and a solvent.

  Thus, when the pigment whose average primary particle diameter is refined to 100 nm or less is dispersed in the resin using a disperser such as a sand mill, the pigment is dispersed in the form of dispersed particles composed of a plurality of secondary particles. The dispersed particles gradually become smaller with the progress of the dispersed state, and finally become dispersed in the state of primary particles, but the dispersed state is controlled by the size of the dispersed particles. In which the average diameter is in the range of 50 nm to 150 nm.

  As the dispersion progresses, the dispersed particle diameter becomes smaller, the transparency increases, and the contrast ratio rises. Therefore, the smaller the dispersed particle diameter is, the better the contrast ratio can be obtained from about 300 nm. On the other hand, when the dispersion progresses and the dispersed particle size becomes small, the viscosity of the dispersion increases and the thixotropic property tends to increase. When used as a photosensitive coloring composition for a color filter, it is required to have a low viscosity and a Newtonian flow because it is required to be coated with a thin film and to have a smooth coating surface. For this reason, it is preferable to suppress the dispersed particle size to about 100 nm in consideration of the viscosity and thixotropic property preferable for normal use. Thus, by using a pigment having an average primary particle size of 100 nm or less and controlling the degree of dispersion so that the average particle size of the dispersed particles is in the range of 50 nm to 150 nm, the increase in viscosity and thixotropic property are minimized. Thus, a pigment dispersion having a very high contrast ratio can be obtained.

  The coloring composition of the present invention is mixed with coarse particles of 5 μm or more, preferably coarse particles of 1 μm or more, more preferably 0.5 μm or more and coarse particles by means of centrifugation, sintered filter, membrane filter or the like. It is preferable to remove dust.

<Color filter>
Next, the color filter of the present invention will be described.
The color filter of the present invention includes a filter segment on a substrate, and can include, for example, a black matrix and red, green, and blue filter segments. The filter segment, after applying the photosensitive coloring composition for color filter by spin coating method or die coating method, by irradiating active energy rays such as ultraviolet rays to cure the portion that becomes the filter segment, and then developing, Formed on a substrate.

The color filter coloring composition produced according to the present invention is used to form a blue or green filter segment, and the other color filter segments are a red photosensitive coloring composition and a green photosensitive coloring that are conventionally used. The composition can be formed using a blue photosensitive coloring composition.
As each color photosensitive coloring composition other than the photosensitive coloring composition for a color filter in the present invention, ordinary photosensitive coloring compositions containing each color pigment, the resin, the photopolymerizable composition (F) and the like are used. Can be formed.

  The red filter segment can be formed using a normal red coloring composition containing a red pigment and a pigment carrier. Examples of the red coloring composition include C.I. I. Pigment Red 7, 14, 41, 48: 1, 48: 2, 48: 3, 48: 4, 57: 1, 81, 81: 1, 81: 2, 81: 3, 81: 4, 122, 146, 168, 169, 177, 178, 184, 185, 187, 200, 202, 208, 210, 242, 246, 254, 255, 264, 270, 272, 273, 274, 276, 277, 278, 279, 280, Red pigments such as 281, 282, 283, 284, 285, 286, or 287 are used. Further, a basic dye or a salt-forming compound of an acid dye exhibiting a red color can also be used.

  The red coloring composition includes C.I. I. Pigment orange 43, 71, 73 or the like and / or 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, 181 182,185,187,188,193,194,198,199,213, or may be used in combination of a yellow pigment 214, and the like.

  When a green filter segment other than the present invention is used, it can be formed using a normal green coloring composition containing a green pigment and a pigment carrier. Examples of the green pigment include C.I. I. Pigment Green 2, 7, 10, 36, 37, 58, etc. are used.

  A yellow pigment can be used in combination with the green coloring composition. Examples of yellow pigments that can be used in combination include 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, 198, 199, 213, 214, 218, 219, 220, 221 and the like.

  When a blue filter segment other than the present invention is used, for example, C.I. I. Blue pigments such as Pigment Blue 15, 15: 1, 15: 2, 15: 3, 15: 4, 15: 6, 16, 22, 60, 64, etc. are used. The blue photosensitive coloring composition includes C.I. I. Pigment Violet 1, 19, 23, 27, 29, 30, 32, 37, 40, 42, 50, and other purple pigments can be used in combination.

  The magenta color filter segment can be formed using a normal magenta color coloring composition including a magenta color pigment and a pigment carrier. Examples of the magenta coloring composition include C.I. I. Pigment Red 81, 81: 1, 81: 2, 81: 3, 81: 4, 122, 192, 202, 207, 209, C.I. I. Pigment Violet 19 or the like is used.

  The yellow filter segment can be formed using a normal yellow coloring composition containing a yellow pigment and a pigment carrier. As a yellow pigment, the pigment illustrated as a yellow pigment which can be used together with a red pigment or a green pigment can be used.

  As the substrate for the color filter, glass plates such as soda lime glass, low alkali borosilicate glass and non-alkali aluminoborosilicate glass having high transmittance for visible light, and resin plates such as polycarbonate, polymethyl methacrylate, polyethylene terephthalate, etc. Is used. In addition, a transparent electrode made of indium oxide, tin oxide, or the like may be formed on the surface of the glass plate or the resin plate in order to drive the liquid crystal after forming the panel.

In development, an aqueous solution such as sodium carbonate or sodium hydroxide is used as an alkali developer, and an organic alkali such as dimethylbenzylamine or triethanolamine can also be used. Moreover, an antifoamer and surfactant can also be added to a developing solution.
As a development processing method, a shower development method, a spray development method, a dip (immersion) development method, a paddle (liquid accumulation) development method, or the like can be applied.
In order to increase the UV exposure sensitivity, after applying and drying the colored composition material, a water-soluble or alkali-soluble resin such as polyvinyl alcohol or water-soluble acrylic resin is applied and dried to form a film that prevents polymerization inhibition by oxygen. Ultraviolet exposure can also be performed after forming.

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

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

Hereinafter, the present invention will be described based on examples, but the present invention is not limited thereto. In the examples and comparative examples, “part” means “part by weight”.
In the following examples, the number average molecular weight and the weight average molecular weight were determined by connecting four separation columns in series in the gel permeation chromatography “HLC-8120GPC” manufactured by Tosoh Corporation. This is a molecular weight in terms of polystyrene measured using “TSK-GEL SUPER H5000”, “H4000”, “H3000”, and “H2000” manufactured by Tetrahydrofuran as a mobile phase.
Further, the volume average primary particle diameter (MV) of the pigment is measured by measuring the short axis diameter and the long axis diameter of 100 primary particles of the pigment using a transmission electron microscope (TEM) photograph. The average of the shaft diameters is defined as the particle diameter (d) of the pigment particles, and then the volume (V) of each particle is determined assuming that each pigment is a sphere having the determined particle diameter. And calculated using the following formula (5).
Formula (5) MV = Σ (V · d) / Σ (V)

  First, the manufacturing method of the refinement | purification processing pigment used for the Example and the comparative example, the manufacturing method of resin (A) solution, and the manufacturing method of a yellow pigment dispersion are shown.

<Method for producing refined pigment>
(Production of refined pigment (PB-1); chloroaluminum phthalocyanine)
Production of an aluminum phthalocyanine pigment (chloroaluminum phthalocyanine) having a structure in which X is a chlorine atom and n11 to n14 are each 0 in formula (3) was performed according to the following procedure. A glass 4-necked flask was charged with 60.0 parts of phthalonitrile, 300 parts of 1-chloronaphthalene, and 15.6 parts of aluminum chloride, and stirred under reflux for 6 hours. Thereafter, heating was stopped, the mixture was allowed to cool to about 200 ° C., filtered while hot, and washed by sprinkling with 600 parts of hot toluene and 300 parts of acetone. The obtained wet cake was dispersed in 250 parts of toluene and stirred and refluxed for 3 hours. The mixture was again filtered while hot, sprinkled and washed with 600 parts of hot toluene and 300 parts of acetone, dispersed in 1500 parts of ion-exchanged water, and heated and stirred at 60 to 70 ° C. for 60 minutes. Filtration, washing with water and vacuum drying at 50 ° C. gave a blue solid aluminum phthalocyanine pigment (AlPc—Cl) having the desired structure.
This (AlPc-Cl pigment 50 parts, sodium chloride 150 parts, and diethylene glycol 25 parts were charged in a stainless steel 1 gallon kneader (manufactured by Inoue Seisakusho Co., Ltd.) and kneaded for 6 hours at 120 ° C. The mixture was poured into warm water, stirred for 1 hour while heating to 70 ° C., made into a slurry, repeatedly filtered and washed with water to remove sodium chloride and diethylene glycol, and then dried at 80 ° C. all day and night to obtain a refined pigment (PB-1 The volume average primary particle diameter of the obtained pigment was 26 nm.

(Production of refined pigment (PB-2); hydroxyaluminum phthalocyanine)
Production of an aluminum phthalocyanine pigment (hydroxyaluminum phthalocyanine) having a structure represented by the formula (4) was performed according to the following procedure. 30 parts of the (AlPc-Cl) pigment before kneader synthesis synthesized in the production of the finely treated pigment (PB-1) was gradually dissolved in 1200 parts of concentrated sulfuric acid while maintaining the temperature at about 5 ° C., and this temperature was maintained for 1 hour. Stir. This was added to 6000 parts of ice water with stirring so that the temperature did not exceed 5 ° C., and further stirred for 1 hour after the end of the addition. After filtration and washing with water, it was redispersed in 6500 parts of ion exchange water and filtered again. After washing with water, the wet cake was redispersed in 2500 parts of 4% aqueous ammonia and stirred under reflux for 6 hours. After filtration, the cake was washed with ion-exchanged water and then vacuum-dried at 50 ° C. to obtain a blue solid aluminum phthalocyanine pigment (AlPc—OH) having the desired structure.
50 parts of this (AlPc-OH) pigment, 150 parts of sodium chloride, and 25 parts of diethylene glycol were charged into a stainless gallon kneader (manufactured by Inoue Seisakusho) and kneaded at 120 ° C. for 6 hours. Next, the kneaded product is poured into 5 liters of 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 dried at 80 ° C. overnight. A refined pigment (PB-2) was obtained. The obtained pigment had a volume average primary particle size of 28 nm.

(Production of refined yellow pigment (PY-1))
Metal complex yellow pigment C.I. I. 50 parts of Pigment Yellow 150 (LANXESS "E4GN"), 250 parts of sodium chloride, and 25 parts of diethylene glycol were charged into a stainless gallon kneader (manufactured by Inoue Seisakusho) and kneaded at 100 ° C for 6 hours. Next, the kneaded product is poured into 5 liters of 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 dried at 80 ° C. overnight. Then, a refined yellow pigment (PY-1) was obtained. The obtained pigment had a volume average primary particle size of 28 nm.

<Method for Producing Resin (A) Solution>
(Preparation of resin solution (A))
233 parts of propylene glycol monomethyl ether acetate was charged into a separable four-necked flask equipped with a thermometer, a cooling pipe, a nitrogen gas introduction pipe, a dropping pipe and a stirring device, and the temperature was raised to 80 ° C. From the tube, 20 parts of methacrylic acid, 30 parts of paracumylphenol ethylene oxide modified acrylate (Aronix M110 manufactured by Toagosei Co., Ltd.), 19 parts of benzyl methacrylate, 16 parts of methyl methacrylate, 15 parts of 2-hydroxyethyl methacrylate, and 2, A mixture of 1.33 parts of 2′-azobisisobutyronitrile was added dropwise over 2 hours. After completion of the dropping, the reaction was further continued for 3 hours to obtain a resin solution having a weight average molecular weight (Mw) of 16000.
After cooling to room temperature, about 2 g of resin solution was sampled and heated and dried at 180 ° C. for 20 minutes to measure the non-volatile content. Propylene glycol monomethyl ether so that the non-volatile content was 20% by weight in the previously synthesized resin solution. Acetate was added to prepare a resin solution (A).

<Method for producing yellow pigment dispersion>
(Preparation of yellow pigment dispersion (DY-1))
After stirring and mixing a mixture having the following composition with a disper, using a zirconia bead having a diameter of 0.5 mm, it is dispersed for 4 hours using an Eiger mill (“Mini Model M-250 MKII” manufactured by Eiger Japan) as a media type wet disperser. After that, a pigment content of 50% and a solid content of 20% were prepared.
Refined yellow pigment (PY-1) 10.0 parts Resin solution (A-1) 50.0 parts Propylene glycol monomethyl ether acetate 40.0 parts

[Example 1]
After stirring and mixing a mixture having the following composition with a disper, using a zirconia bead having a diameter of 0.5 mm, it is dispersed for 4 hours using an Eiger mill (“Mini Model M-250 MKII” manufactured by Eiger Japan) as a media type wet disperser. After that, a pigment content of 50% and a solid content of 20% were prepared to obtain a blue pigment dispersion (DB-1).

Aluminum phthalocyanine pigment (PB-1) 8.5 parts Resin (A) solution 50.0 parts Propylene glycol monomethyl ether acetate 40.0 parts Pigment derivative (C-1): Copper phthalocyanine sulfonic acid derivative manufactured by Nippon Lubrizol Corporation "Solspurs 12000" 1.5 parts

[Examples 2-8 and Comparative Examples 1-2]
Blue pigment dispersions (DB-2 to 10) were prepared in the same manner as in Example 1 except that the composition and blending amount (parts by weight) as shown in Table 1 were changed.

Abbreviations in Table 1 are shown below.
Pigment derivative (C-1): Copper phthalocyanine sulfonic acid derivative “Solspers 12000” manufactured by Nippon Lubrizol Corporation
Pigment derivative (C-2): Copper phthalocyanine sulfonic acid derivative “Solspers 5000” manufactured by Nippon Lubrizol Corporation
Pigment derivative (C-3): Pigment derivative represented by the following formula (15)

〔式（１５）中、ＣｕＰｃは、銅フタロシアニン構造残基である。〕 Formula (15):

[In Formula (15), CuPc is a copper phthalocyanine structure residue. ]

〔式（１６）中、ＣｕＰｃは、銅フタロシアニン構造残基である。〕 Pigment derivative (C-4): Pigment derivative formula (16) represented by the following formula (16):

[In Formula (16), CuPc is a copper phthalocyanine structure residue. ]

樹脂型顔料分散剤１：ビックケミー社製：リン酸基含有顔料分散剤「ＢＹＫ１１１」
樹脂型顔料分散剤２：味の素ファインテクノ社製：塩基性基を有する樹脂型分散剤「ＰＢ−８２１」 Pigment derivative 1: Pigment derivative formula (17) represented by the following formula (17)

Resin-type pigment dispersant 1: manufactured by Big Chemie: Phosphoric acid group-containing pigment dispersant “BYK111”
Resin type pigment dispersant 2: Ajinomoto Fine Techno Co., Ltd .: Resin type dispersant having a basic group “PB-821”

  The pigment dispersions prepared in Examples and Comparative Examples were evaluated by the following evaluation methods. The results are shown in Table 2.

As in the examples, when a pigment derivative having a phthalocyanine structure as a base skeleton is used, the change in spectral shape is suppressed and the crystal system is maintained. As a result, the heat resistance and light resistance are very good. It was. If a pigment derivative is not used as in the comparative example, or only a pigment derivative that does not have a phthalocyanine structure as a base skeleton, the spectrum changes greatly and the crystal system is significantly lost, resulting in very poor heat resistance and light resistance. It was.
In addition, when an acidic derivative was used as the pigment derivative, particularly excellent results were obtained from the viewpoints of heat resistance and light resistance. Furthermore, the combined use of an acidic derivative and a basic derivative resulted in very good heat resistance and light resistance.
Furthermore, the use of a resin-type dispersant resulted in good heat resistance.

<Heat and light resistance evaluation>
[Spectral shape evaluation]
The colored compositions obtained in Examples 1 to 8 and Comparative Examples 1 and 2 were placed on a glass substrate having a thickness of 100 mm × 100 mm and a thickness of 1.1 mm, using a spin coater and y (C) = 0.29. Then, the coating film was coated at a film thickness to be, and then dried at 70 ° C. for 20 minutes to obtain a coated substrate.
The obtained coated substrate and the transmission spectrum after heat treatment at 230 ° C. for 1 hour were measured using a microspectrophotometer (“OSP-SP100” manufactured by Olympus Optical Co., Ltd.). From the obtained transmission spectrum (T), the absorption spectrum (Abs) was calculated from the following formula (18).

Formula (18) Abs = -log (T)

Peak value around 630 nm due to aluminum phthalocyanine pigment before and after heat treatment at 230 ° C. (A ₆₃₀ ; before heat treatment, A ′ ₆₃₀ ; after heat treatment) and peak value around 670 nm (A ₆₇₀ ; before heat treatment, A ′ ₆₇₀ ; after heat treatment) Was used to calculate a parameter representing the degree of spectral shape change from the following equations (19) and (20).
Formula (19) _R630 = _A'630 / _A630
Formula (20) _R670 = _A'670 / _A670
The closer the R ₆₃₀ value calculated here is to 1, the more steep spectral shape is maintained, which is advantageous in terms of brightness. In addition, the smaller the value of R _670, the more the index indicates that the crystal system is maintained. Each was evaluated in three stages according to the following criteria.
(Lightness evaluation; R ₆₃₀ )
○: 85% or more Δ: 75% or more and less than 85% ×: less than 75% (heat resistance evaluation; R ₆₇₀ )
○: 100% or more and less than 150% △: 150% or more and less than 200% ×: 200% or more

[Color difference evaluation]
The colored compositions obtained in Examples 1 to 8 and Comparative Examples 1 and 2 were placed on a glass substrate having a thickness of 100 mm × 100 mm and a thickness of 1.1 mm, using a spin coater and y (C) = 0.29. A coated substrate was obtained. Next, it was dried at 70 ° C. for 20 minutes, then heated at 230 ° C. for 1 hour and allowed to cool, and then the chromaticity of the obtained coating film was measured using a microspectrophotometer (“OSP-SP100” manufactured by Olympus Optical Co., Ltd.) L * (1), a * (1), b * (1)] were measured.
(Heat resistance evaluation)
Further, the chromaticity [L * (2), a * (2), b * (2)] after heat treatment at 250 ° C. for 1 hour is measured, and the color difference ΔE * ab is obtained by the following equation (21). It was.
Formula (21)
ΔE * ab = [[L * (2) −L * (1)] ² + [a * (2) −a * (1)] ² + [b * (2) −b * (1)] ² ] ^1/2
(Light resistance evaluation)
Similarly, a coated substrate was prepared, and the chromaticity [L * (2), a * (2), b * (2)] after irradiation with ultraviolet rays using a 470 W / m 2 xenon lamp was measured. The color difference ΔE * ab was determined from Equation (12).

<Preparation of photosensitive coloring composition>
[Examples 9 to 18 and Comparative Examples 3 to 5]
Each material was mixed and stirred with the composition and blending amount (parts by weight) shown in Table 3, and filtered through a 1 μm filter to prepare photosensitive coloring compositions (RB-1 to 11) and (RG-1 and 2). Each was produced.

Abbreviations in Table 3 are shown below.
Blue pigment dispersion: previously prepared blue pigment dispersion (DB-1 to 10)
Yellow pigment dispersion: previously prepared yellow pigment dispersion (DY-1)
Photopolymerizable compound: trimethylolpropane triacrylate (“NK ester ATMPT” manufactured by Shin-Nakamura Chemical Co., Ltd.)
Photopolymerization initiator: “Irgacure 907” manufactured by Ciba Japan
Sensitizer: “EAB-F” manufactured by Hodogaya Chemical Co., Ltd.
Solvent: Cyclohexanone Thermosetting resin: Thermosetting melamine compound ("MW-30" manufactured by Sanwa Chemical Co., Ltd.)

  Each photosensitive coloring composition prepared in Examples and Comparative Examples was evaluated by the following evaluation method. The results are shown in Table 4.

<Measurement of halogen content>
The halogen atom content in the alkali-developable photosensitive coloring compositions prepared in Examples and Comparative Examples was measured by ICP emission spectroscopy (inductively coupled plasma emission analyzer “SPS4000” manufactured by SII Nanotechnology). .

<Heat and light resistance evaluation>
[Spectral shape evaluation]
The alkali developing type photosensitive coloring composition obtained in Examples 9 to 18 and Comparative Examples 3 to 5 was applied to a blue photosensitive coloring composition using a spin coater on a glass substrate of 100 mm × 100 mm and 1.1 mm thickness. The product was a C light source and y (c) = 0.29, and the green photosensitive coloring composition was y (c) = 0.69. Next, after drying at 70 ° C. for 20 minutes, using an ultra-high pressure mercury lamp, UV exposure was performed with an integrated light amount of 150 mJ, and development was performed with an alkali developer to obtain a coated substrate.
The obtained coating film substrate and a transmission spectrum after heat treatment at 230 ° C. for 1 hour were measured using a microspectrophotometer (“OSP-SP100” manufactured by Olympus Optical Co., Ltd.), and Examples 1 to 8, Comparative Example 1, Evaluation similar to 2 was performed.

[Color difference evaluation]
The alkali developing type photosensitive coloring composition obtained in Examples 9 to 18 and Comparative Examples 3 to 5 was applied to a blue photosensitive coloring composition using a spin coater on a glass substrate of 100 mm × 100 mm and 1.1 mm thickness. The product was a C light source and y (c) = 0.29, and the green photosensitive coloring composition was y (c) = 0.69. Next, after drying at 70 ° C. for 20 minutes, using an ultra-high pressure mercury lamp, UV exposure was performed with an integrated light amount of 150 mJ, development was performed with an alkaline developer, and then heated at 230 ° C. for 1 hour and allowed to cool to obtain. [L * (1), a * (1), b * (1)] was measured for the chromaticity of the coating film using a microspectrophotometer ("OSP-SP100" manufactured by Olympus Optical Co., Ltd.).
(Evaluation of heat resistance and light resistance)
Evaluation similar to Examples 1-8 and Comparative Examples 1 and 2 was performed.

Even when the alkali developing type photosensitive coloring composition was used, the result was the same as that of the pigment dispersion, and the characteristics excellent in heat resistance and light resistance were exhibited. Furthermore, when a melamine compound, which is a thermosetting resin, was added, the film was cured by heat, resulting in very good heat resistance and light resistance.
Moreover, the measurement result of the halogen atom amount of the photosensitive coloring composition of this invention became 500 ppm or less about all the photosensitive coloring compositions about the bromine atom. Moreover, about chlorine atom, all became 500 ppm or less except having become 5000 ppm or less by the photosensitive coloring composition (RB-2).
<Production of color filter>
Next, a black matrix is patterned on a glass substrate, and the pigment used in the coloring composition in the photosensitive blue coloring composition (RB-1) is formed on the substrate by a spin coater. I. Pigment Red 254 / C.I. I. Pigment Red 177 = 5.1 parts / 0.9 parts except that the photosensitive red coloring composition produced in the same manner as in Example 9 was used in a C light source (hereinafter also used for green and blue) x = 0 .670, y = 0.330 was applied to form a colored film. Next, the film was irradiated with 300 mJ / cm ² of ultraviolet rays through a photomask using an ultrahigh pressure mercury lamp. Next, spray development is performed with an alkali developer composed of a 2% by weight aqueous sodium carbonate solution to remove unexposed portions, and then the substrate is washed with ion-exchanged water. The substrate is heated at 230 ° C. for 20 minutes to form a red filter segment. did.
Similarly, in the photosensitive blue coloring composition (RB-1) so that the photosensitive green coloring composition (RG-1) obtained in Example 18 was x = 0.205 and y = 0.640. The pigment used in the coloring composition is C.I. I. Pigment Blue 15: 6 / C.I. I. Pigment Violet 23 = 3.6 parts / 2.4 parts were used, except that x = 0.149 and y = 0.048 were obtained using a blue photosensitive coloring composition produced in the same manner as in Example 9. Each film was applied to a different thickness to form a green filter segment and a blue filter segment to obtain a color filter.
Further, using the same photosensitive coloring composition as described above, a red filter segment of x = 0.640, y = 0.330, a green filter segment of x = 0.214, y = 0.600 in a C light source, x = 0.150, y = 0.06 were applied to the film thickness so as to be a blue filter segment to obtain a color filter.
When the photosensitive coloring composition for a color filter in the present invention is used, a color filter having a green filter segment having excellent color density, color purity, transparency, heat resistance and light resistance in a wide chromaticity range is produced. It was possible.

Claims (7)

    A coloring composition comprising at least a resin (A), a colorant (B) containing an aluminum phthalocyanine pigment, and a pigment derivative (C) having a phthalocyanine structure as a base skeleton. The colored composition according to claim 1, wherein the pigment derivative (C) having a phthalocyanine structure as a base skeleton includes a pigment derivative represented by the following formula (1).
Equation (1) Pc-SO ₃ Y
(In Formula (1), Pc represents a phthalocyanine structure residue, and Y is any one of hydrogen, a 1-3 valent metal atom, an organic amine, or ammonia.)   Furthermore, the coloring composition of Claim 2 containing the pigment derivative (C2) which makes a base skeleton the phthalocyanine structure which has a basic substituent.   The colored composition according to any one of claims 1 to 3, wherein the resin (A) contains a thermosetting resin (A2).   The colored composition according to any one of claims 1 to 4, further comprising a resin-type pigment dispersant (D).   The photosensitive coloring composition for a color filter comprising the coloring composition according to any one of claims 1 to 5, further comprising a photopolymerization initiator (E) and / or a photopolymerizable composition (F). . A color filter comprising a filter segment formed using the photosensitive coloring composition for a color filter according to claim 6.