JPH09171108A - Color filter containing phthalocyanine compound - Google Patents

Abstract

PROBLEM TO BE SOLVED: To obtain a color filter contg. a phthalocyanine compd. having excellent solubility with resins by incorporating the phthalocyanine compd. in which the substitutable positions of the benzene nuclei of phthalocyanine skeleton are partly substd. for phenoxy groups having substituents in ortho positions. SOLUTION: This color filter contains the phthalocyanine compd. in which 1 to 8 pieces among 16 pieces of the substitutable positions of the benzene nuclei of the phthalocyanine skeleton is or are substd. for phenoxy group having the substituents in one or both of the ortho positions. The substituents referred to here denote all nonmetal atom groups excluding hydrogen atoms. The nonmetal atom groups denote halogen atoms, alkyl groups, etc. The total of the atom radii of the atoms excluding the hydrogen atoms among the atoms included in the substituents in the ortho positions of the phenoxy groups is preferably >=3.0 angstrom.

Description

Detailed Description of the Invention

[0001]

TECHNICAL FIELD The present invention relates to a color filter containing a phthalocyanine compound.

The phthalocyanine compound used in the present invention has absorption in the visible light region of 400 to 700 nm and is excellent in solubility in a resin, and these phthalocyanine compounds are also excellent in light resistance or heat resistance. Therefore, it is excellent as a display material having absorption in the visible region in the optoelectronic information field, for example, as a color separation filter used in an image pickup tube, a color filter for liquid crystal display, an optical color filter, a color filter for plasma display, etc. Exert the effect. The present invention can be used for blue and green color filters for liquid crystal displays. In particular, it exhibits a very excellent effect when used for green.

[0003]

2. Description of the Related Art In recent years, liquid crystal display devices (LC)
D) is rapidly expanding its use in personal computers and word processors, as well as in car navigation systems and display devices for mobile phones, with the focus on full color and low cost, and the market continues to expand year by year. Color filters are indispensable for full color display.

A color filter is usually formed by repeatedly forming fine colored pixels of a thin film colored in a plurality of colors on a substrate such as glass, plastic, an image pickup device, and a thin film transistor, and further, if necessary, a protective film thereon. Is provided. Various methods have been proposed as methods for forming the colored pixels.

The coloring matter which is a constituent of the color filter is roughly classified into a pigment type and a dye type. Examples of the pigment-based manufacturing method include an acrylic resin, a pigment dispersion method using a colored layer in which a pigment is dispersed in a polyimide resin or a Poval resin, a printing method using an ink in which a pigment is dispersed in an epoxy resin, and an acrylic resin. An electrodeposition method using a colored layer in which a pigment is dispersed in a resin or an epoxy resin has been put into practical use. In addition to this, as a new method, a three-color film coated with a resist resin in which a pigment is dispersed is attached to each glass substrate, and a transfer method in which a color filter is formed when peeled off, or a sol of pigment-dispersed silica is used. A method of selectively coloring a polysilane film by a sol-gel method has also been proposed. However, in any of the methods, since the dispersibility of the pigment in the resin is not sufficient, there have been problems in that the transmittance when formed into a color filter is insufficient and the contrast is poor.

On the other hand, in the dye system, a dyeing method in which a dyeable resin such as gelatin is used for dyeing has been put to practical use, and although it is superior in color to the pigment system, it has heat resistance and durability. Another problem is that the chemical resistance is poor. Therefore, there is a demand for a material that retains the conventional dye-based color and has high durability.

As a dye having high durability and solubility in a solvent, a phthalocyanine compound having a substituent is known. An example of using a soluble phthalocyanine compound in a color filter is disclosed in JP-A-1-23340.
1, JP-A-5-295283 and the like are known.

However, although the phthalocyanine compound having a substituent at the β-position described in JP-A-1-233401 is excellent in durability,
The transmission characteristics were not sufficient.

JP-A-5-295283 proposes a phthalocyanine compound substituted with a substituent having a hetero atom at the α-position as a solution to those drawbacks. However, even though this compound is proposed for a dye for a green color filter, in order to obtain a transmission characteristic suitable for a dye for a green color filter, a large amount of a yellow dye is used at about 50% of the whole dye. It is necessary to mix them, and there is a problem in terms of transmission characteristics. Further, such a phthalocyanine compound does not necessarily satisfy all the properties, and thus further better properties are desired.

[0010]

SUMMARY OF THE INVENTION Therefore, an object of the present invention is to improve the above-mentioned conventional drawbacks, and a color containing a phthalocyanine compound having excellent solubility in a resin. To provide a filter.

Another object of the present invention is 400 to 700 nm.
Another object of the present invention is to provide a color filter containing a phthalocyanine compound which has absorption in the visible light range, excellent solubility in a resin, and excellent light resistance or heat resistance.

Still another object of the present invention is to provide a color filter which is excellent in light resistance and heat resistance, has a transparent feeling without turbidity, and is excellent in color tone, and in particular, a blue or green color filter for liquid crystal display. In particular, it is to provide a color filter for green.

[0013]

The above objects are achieved by the following (1) to (5).

(1) Including a phthalocyanine compound in which 1 to 8 of the 16 substitutable positions of the benzene nucleus of the phthalocyanine skeleton are substituted with a phenoxy group having a substituent at one or both of the ortho positions. Color filter.

(2) Among the atoms contained in the substituent at the ortho position of the phenoxy group, the total atomic radius of atoms excluding hydrogen atoms is 3.0 angstroms or more.
The color filter according to 1.

(3) General formula (1)

[0017]

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{In the formula (1), X represents at least one atom selected from a hydrogen atom and a halogen atom, and Y represents a general formula (2).

[0019]

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(Wherein R ¹ , R ² , R ³ , R ⁴ and R
⁵ each independently represents a linear, branched or cyclic alkyl group having 1 to 20 carbon atoms or an aryl group which may be substituted, R ⁶ represents an aryl group which may be substituted, A is CH Represents a group or a nitrogen atom, B represents an oxygen atom, a sulfur atom, a CH ₂ group, an NH group or an alkylamino group having 1 to 4 carbon atoms, and f, g, h and j are integers of 1 to 5 And i and k are integers of 0 to 6 and 1 and m are each independently an integer of 1 to 4), and W is a halogen atom and / or Z. It represents at least one kind of substituent selected, and e is an integer of 0-4. ] Represents a phenoxy group having a substituent at the ortho position, and a to d are 0 to
It is an integer of 4 and the sum of a to d is an integer of 1 to 8, and M represents a metal, a metal oxide or a metal halide. } The color filter as described in said (1) or (2) containing the phthalocyanine compound shown by these.

(4) The color filter according to any one of (1) to (3) above, which comprises a phthalocyanine compound and a resin.

(5) The above (4), wherein the resin is a photosensitive resin
The color filter according to 1.

[0023]

BEST MODE FOR CARRYING OUT THE INVENTION In the color filter according to the present invention, 1 to 8 out of 16 substitutable positions of the benzene nucleus of the phthalocyanine skeleton are substituted with a phenoxy group having a substituent at one or both of the ortho positions. The phthalocyanine compound described above is included.

The term "substituent" as used herein refers to all non-metal atomic groups other than hydrogen atoms, and examples of non-metal atomic groups include halogen atoms, alkyl groups, aryl groups, heterocyclic groups, cyano groups and hydroxy groups. , Nitro group, amino group (including substituted amino group), alkoxy group, aryloxy group, acylamino group, aminocarbonylamino group, sulfamoylamino group, alkylthio group, arylthio group, alkoxycarbonylamino group, sulfonylamino group, Carbamoyl group, sulfamoyl group, sulfonyl group, alkoxycarbonyl group, heterocyclic oxy group, azo group, acyloxy group, carbamoyloxy group, silyloxy group, aryloxycarbonyl group, imide group, heterocyclic thio group,
It represents a sulfinyl group, a phosphoryl group, an acyl group or the like.

The phthalocyanine compound of the present invention has a substituent at the ortho position of its phenoxy group,
Of the atoms contained in the substituent, the total atomic radius of atoms excluding hydrogen atoms is preferably 3.0 angstroms or more. {Here, the following numbers were used for the atomic radii of the main atoms (unit = angstrom). Carbon =
0.77, oxygen = 0.74, nitrogen = 0.74, fluorine =
0.72, chlorine = 0.99, bromine = 1.14, silicon =
1.17, phosphorus = 1.10, sulfur = 1.04}. 3.0
When it is at least angstrom, it has a better effect on the solubility in resin and the absorption wavelength. Thus, a preferred color filter of the present invention comprises a phthalocyanine compound having a total atomic radius of 3.0 angstroms or more among atoms contained in the ortho-positioned substituent of the phenoxy group excluding hydrogen atoms. Color filters are provided.

In the present invention, a color filter containing the phthalocyanine compound represented by the general formula (1) is preferable.

Substituents optionally present in the optionally substituted aryl group in the definition of Z are, for example, lower alkyl group (C ₁ -C ₄ ), lower alkoxy group (C ₁
To C ₄ ), a halogen atom, a nitro group, an amino group, an alkyl (C _{1 to} C ₄ ) amino group, an alkoxycarbonyl group (C _{1 to} C ₄ ), and the like.

These compounds represented by the general formula (1) are those in which 1 to 8 phenoxy groups are introduced into the phthalocyanine skeleton. By introducing a sublime substituent Z in the ortho position of the phenoxy group, Solubility to resist resin while maintaining light resistance, excellent characteristics in controlling absorption wavelength are obtained, and thus color filters containing phthalocyanine compounds are effective, and exhibit excellent effects in light resistance and control of absorption wavelength. The present inventors have found out what can be done.

In the present invention, 16 phthalocyanine compounds are used.
1 to 8 phenoxy groups are substituted at the bonding positions of the benzene nuclei, but a halogen atom or a hydrogen atom is substituted at the residual position (X in the general formula (1)).

The residual X at that time is preferably a fluorine atom and a hydrogen atom, and particularly preferably a fluorine atom. By using a fluorine atom, the solubility is further improved. Thus, as a preferred color filter of the present invention, a color filter containing a phthalocyanine compound in which X is a fluorine atom in the general formula (1) is provided.

The phenoxy group substituted on the phthalocyanine skeleton in the phthalocyanine compound used in the present invention has a bulky substituent Z at the ortho position, but may have another substituent W in addition to this. Good. When it has W, W can be substituted by 1 to 4 with respect to the phenoxy group, at least one of which is located in the ortho position of the phenoxy group, that is, with respect to the phenoxy group. It is preferred that the groups Z and W are located in the 2,6 position. Having a substituent at the 2,6-position of the phenoxy group exerts a better effect on the solubility in resin and the absorption wavelength. Thus, as a preferred color filter of the present invention, there is provided a color filter containing a phthalocyanine compound in which one of W in the general formula (2) is located at the ortho position of the phenoxy group.

In the present invention, the number of phenoxy groups substituted on the phthalocyanine skeleton in the general formula (1) is preferably 3 to 5. Further, the phenoxy group is represented by the general formula (3)

[0033]

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In the structural formula of phthalocyanine shown in:
It is preferably contained at any of positions 2, 3, 6, 7, 10, 11, 14 and 15. 2, 3, 6,
The presence of a total of 3 to 5 phenoxy groups at any of positions 7, 10, 11, 14 and 15 exerts a better effect on the suitability of the absorption wavelength for the color filter dye. Thus, in the structural formula of phthalocyanine represented by the general formula (3) as a preferable color filter of the present invention, 2, 3, 6, 7, 10, 11, 1
There is provided a color filter comprising a phthalocyanine compound having a total of 3 to 5 phenoxy groups at any of positions 4 and 15.

The phenoxy group substituted on the phthalocyanine skeleton of the present invention has a bulky substituent introduced at the ortho position and is represented by Z in the above general formula (2) (1) to (1).
It is preferable to use the substituents of group (7). The phenoxy group can be further substituted with a substituent W. W is at least one substituent selected from Z or a halogen atom, and preferably at least one substituent selected from Z. Furthermore, one of the substituents W is in the ortho position of the phenoxy group, that is, the substituents Z and W are 2 in the phenoxy group.
Substitutions at positions 6 and 6 are preferred. Further, at that time, it is preferable that the total number of both positions of the number of atoms excluding hydrogen of the substituents substituted at the 2-position and the 6-position of the phenoxy group is 7 or more.

Specific examples of the substituents substituted at the 2-position, 6-position or both positions of these phenoxy groups include the following.

Group (1): methyl, ethyl, propyl, isopropyl, cyclopropyl, butyl, isobutyl, s
ec-butyl, tert-butyl, straight or branched pentyl, straight or branched hexyl, cyclohexyl, straight or branched heptyl, straight or branched octyl, straight or branched nonyl, straight or branched Decyl, linear or branched undecyl, linear or branched dodecyl, phenyl, o-
Methylphenyl, m-methylphenyl, p-methylphenyl, o-ethylphenyl, m-ethylphenyl, p-
Ethylphenyl, o-propylphenyl, m-propylphenyl, p-propylphenyl, o-isopropylphenyl, m-isopropylphenyl, p-isopropylphenyl, o-butylphenyl, m-butylphenyl,
p-butylphenyl, o-tert-butylphenyl,
m-tert-butylphenyl, p-tert-butylphenyl, o-methoxyphenyl, m-methoxyphenyl, p-methoxyphenyl, o-ethoxyphenyl, m
-Ethoxyphenyl, p-ethoxyphenyl, o-propoxyphenyl, m-propoxyphenyl, p-propoxyphenyl, o-isopropoxyphenyl, m-isopropoxyphenyl, p-isopropoxyphenyl, o
-Butoxyphenyl, m-butoxyphenyl, p-butoxyphenyl, 2,6-dimethylphenyl, 2,6 diethylphenyl, 2,6-dipropylphenyl, 2,6-
Diisopropylphenyl, 2,6-dibutylphenyl,
2,6-ditert-butylphenyl, 2,6-dimethoxyphenyl, 2,6-diethoxyphenyl, 2,6-
Dipropoxyphenyl, 2,6-diisopropoxyphenyl, 2,6-dibutoxyphenyl, 2-fluorophenyl, 2-chlorophenyl, 2-bromophenyl, 2-
Iodophenyl, 3-fluorophenyl, 3-chlorophenyl, 3-bromophenyl, 3-iodophenyl,
-Fluorophenyl, 4-chlorophenyl, 4-bromophenyl, 4-iodophenyl, 2,3-difluorophenyl, 2,3-dichlorophenyl, 2,4-difluorophenyl, 2,4-dichlorophenyl, 2,4-dibromophenyl , 2,5-difluorophenyl, 2,5-
Dichlorophenyl, 2,6-difluorophenyl, 2,
6-dichlorophenyl, 2,6-dibromophenyl,
3,4-difluorophenyl, 3,4-dichlorophenyl, 3,5-difluorophenyl, 3,5-dichlorophenyl, 2,3,4-trifluorophenyl, 2,3,3
4-trichlorophenyl, 2,3,5-trifluorophenyl, 2,3,5-trichlorophenyl, 2,3,6
-Trifluorophenyl, 2,3,6-trichlorophenyl, 2,4,6-trifluorophenyl, 2,4,6
-Trichlorophenyl, 2,4,6-tribromophenyl, 2,4,6-triiodophenyl, 2,3,5,6
-Tetrafluorophenyl, pentafluorophenyl,
Pentachlorophenyl.

Group (2): methoxycarbonyl, ethoxycarbonyl, propoxycarbonyl, isopropoxycarbonyl, butoxycarbonyl, isobutoxycarbonyl, sec-butoxycarbonyl, tert-butoxycarbonyl, linear or branched pentyloxycarbonyl, linear or Branched hexyloxycarbonyl, cyclohexyloxycarbonyl, straight or branched heptyloxycarbonyl, straight or branched octyloxycarbonyl, straight or branched nonyloxycarbonyl, straight or branched decyloxycarbonyl, straight or branched Undecyloxycarbonyl, linear or branched dodecyloxycarbonyl, cyclohexanemethoxycarbonyl, cyclohexaneethoxy Carbonyl, 3-cyclohexyl -1
-Propoxycarbonyl, tert-butylcyclohexyloxycarbonyl, phenoxycarbonyl, 4-methylphenoxycarbonyl, 4-chlorophenoxycarbonyl, 4-cyclohexylphenoxycarbonyl, 4
-Phenylphenoxycarbonyl, 2-fluorophenoxycarbonyl, 4-ethoxyphenoxycarbonyl.

Group (3): methoxyethoxycarbonyl,
Ethoxyethoxycarbonyl, 3 ', 6'-oxaheptyloxycarbonyl, 3', 6'-oxaoctyloxycarbonyl, 3 ', 6', 9'-oxadecyloxycarbonyl, 3 ', 6', 9 ', 12 ′ -Oxatridecyloxycarbonyl.

Group (4): methoxypropyloxycarbonyl, ethoxypropyloxycarbonyl, 4 ', 8'
-Oxanonyloxycarbonyl, 4 ', 8'-oxadecyloxycarbonyl, 4', 8 ', 12'-oxatridecyloxycarbonyl. (5) group: methoxy, ethoxy, propoxy, isopropoxy, butoxy, isobutoxy, sec-butoxy,
tert-butoxy, linear or branched pentyloxy, linear or branched hexyloxy, cyclohexyloxy, linear or branched heptyloxy,
Linear or branched octyloxy, linear or branched nonyloxy, linear or branched decyloxy, linear or branched undecyloxy, linear or branched dodecyloxy, methoxyethoxy, ethoxyethoxy, 3 ', 6' -Oxaheptyloxy,
3 ', 6'-oxaoctyloxy, 3', 6 ', 9'
-Oxadecyloxy, 3'6 ', 9', 12'-oxatridecyloxy, methoxypropyloxy, ethoxypropyloxy, 4 ', 8'-oxanonyloxy,
4 ', 8'-oxadecyloxy.

Group (6): benzyloxycarbonyl, phenethyloxycarbonyl, 3-fer-1-propoxycarbonyl, 4-phenyl-1-butoxycarbonyl, 5-phenyl-1-pentoxycarbonyl, 6-phenyl-1-. Hexyloxycarbonyl.

Group (7): 2-tetrahydroxyfuranoxycarbonyl, 4-tetrahydropyranooxycarbonyl, 2-pyrrolidinooxycarbonyl, 2-piperidinooxycarbonyl, 2-tetrahydrothiopheneoxycarbonyl, tetrahydrofurfuryloxy Carbonyl, 4-tetrahydropyranooxycarbonyl, 2-morpholinoethoxycarbonyl, 2-pyrrolidinoethoxycarbonyl, 2-piperazinoethoxycarbonyl.

Examples of the substituent W other than the groups (1) to (7) include a halogen atom, specifically, a fluorine atom, a chlorine atom, a bromine atom and an iodine atom,
Preferred are a chlorine atom and a bromine atom. A new substituent may be introduced at the positions remaining after the introduction of the substituents Z and W into the phenoxy group in order to further improve the solubility or control the absorption wavelength. As these substituents, an alkoxycarbonyl consisting of a linear or branched alkoxy having 1 to 20 carbon atoms, preferably 1 to 4 carbon atoms, which may be substituted with a halogen atom and / or an alkoxy group, is substituted. Optionally substituted aryloxycarbonyl group, linear or branched alkyl group having 1 to 12 carbon atoms which may be substituted, preferably 1 to 4 alkyl group, linear or branched carbon number 1 to 1 12 pieces,
Preferably 1 to 4 alkoxyl groups, linear or branched C1 to C20, preferably 1 to 4 monoalkylamino groups, linear or branched C1 to C1.
20, preferably 1 to 4 dialkylamino groups, cyclohexyl groups, optionally substituted phenoxy groups,
Examples thereof include an anilino group or a nitro group which may be substituted.

In the present invention, those having a bulky substituent at the 2,6 position of the phenoxy group are preferable, but one of the substituents at the 2,6 position is the above groups (2) to (4) and ( 6)
It is preferably a substituent selected from the group (7) to (7).
In particular, one of the substituents at the 2 and 6 positions is (2)-
It is preferable that it is a substituent selected from the groups (4) and (6) to (7), and the other is a substituent selected from the groups (1) and (3). This is preferable in view of compatibility of absorption wavelength when used as a dye for a green color filter.

In the above general formula (1), M is a metal, a metal oxide or a metal halide. Specific examples of the central metal of the phthalocyanine compound represented by M include iron chloride, iron, magnesium, nickel, cobalt, copper, palladium, zinc, aluminum chloride, indium chloride, germanium chloride, tin chloride, silicon chloride, titanyl, vanadyl and the like. Is mentioned. When used as a dye for a green color filter, a tetravalent metal having a ligand, such as tin chloride, silicon chloride, titanyl, and vanadyl, is preferable in view of compatibility with absorption wavelength. Particularly preferred are tin chloride and vanadyl. Further, when used as a dye for a blue color filter, a divalent metal such as iron, magnesium, nickel, cobalt, copper, palladium, or zinc is preferable from the viewpoint of compatibility of absorption wavelength. Particularly preferred are cobalt, copper, palladium and zinc.

The phthalocyanine compound used in the present invention is
Specific examples include compounds 1 to 68 shown in the following Tables 1 to 17.

[0047]

[Table 1]

[0048]

[Table 2]

[0049]

[Table 3]

[0050]

[Table 4]

[0051]

[Table 5]

[0052]

[Table 6]

[0053]

[Table 7]

[0054]

[Table 8]

[0055]

[Table 9]

[0056]

[Table 10]

[0057]

[Table 11]

[0058]

[Table 12]

[0059]

[Table 13]

[0060]

[Table 14]

[0061]

[Table 15]

[0062]

[Table 16]

[0063]

[Table 17]

Among the compounds shown in Tables 1 to 17, compounds 1 to 44 are preferable as the color filter dye for green color, and 45 as the color filter dye for blue color.
Compounds of -68 are preferred.

The fluorinated phthalocyanine used in the present invention can be synthesized, for example, according to the first step and the second step of the first method or the second method of the following scheme, respectively.

The inventors of the present invention described the first and second steps of the scheme described below in Japanese Patent Application Nos. 61-173710 and 61-288671.
Japanese Patent Application No. 63-65806, Japanese Patent Application No. 63-2138.
No. 30, Japanese Patent Application No. 1-103554, Japanese Patent Application No. 2-144
No. 292, Japanese Patent Application No. 4-23846, Japanese Patent Application No. 4-262
186, Japanese Patent Application No. 4-28185, Japanese Patent Application No. 4-274
Since it is disclosed in No. 125, etc., it can be synthesized in the same manner.

In the formulas below, the meanings of Z, W, and e are the same as defined in the above formulas (1) and (2).

[0068]

[Chemical 6]

[0069]

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[0070]

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[0071]

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Specific production examples of these are exemplified by the compound (1
8) and (4) are shown below.

Production Example of Exemplified Compound (18) Step (a) Synthesis of 3,4,6-trifluoro-5- (2-methyl-6-methoxyethoxycarbonyl) phenoxyphthalonitrile In 100 ml four-necked flask. In addition, 6.32 g (31.6 mmol) of tetrafluorophthalonitor and 7.30 g (34.8 mmo) of methoxyethyl 2,3-cresotinate.
l), 2.75 g (47.4 mmol) of potassium fluoride (trade name: Kurocat F, manufactured by Morita Chemical Co., Ltd.) and 60 ml of acetonitrile were reacted for 4 hours under reflux conditions. After the completion of the reaction, the solvent was distilled off after the insoluble matter was filtered off, and 1% aqueous sodium hydroxide (200 ml) was added.
The product was washed twice with 200 ml of water to obtain 15.5 g of the target white cake. (Yield, 95.6% based on tetrafluorophthalonitrile).

Elemental analysis (%) C H N F theoretical value 58.47 3.36 7.18 14.60 actual value 58.21 3.48 7.52 14.43 (b) step of exemplary compound (18) Synthesis of Phthalocyanine 7.0 g (17.9) of 3,4,6-trifluoro-5- (2-methyl-6-methoxyethoxycarbonyl) phenoxyphthalonitrile in a 100 ml four-necked flask.
mmol), 0.85 g of vanadium trichloride (5.4 mm
ol) and 25 ml of benzonitrile.
The reaction was performed at 4 ° C. for 4 hours. After completion of the reaction, the insoluble matter was filtered off, the solvent was distilled off, and the residue was washed twice with 200 ml of methanol to obtain 4.26 g of the desired green cake.
(Yield, 58.4% based on phthalonitrile).

Maximum absorption wavelength 711.0 nm in ethyl cellosolve (ε = 9.21)
X10 ⁴ ) Solubility 15% by weight with respect to ethyl cellosolve Elemental analysis (%) C H N F theoretical value 56.06 3.32 6.88 14.00 actual value 56.31 3.49 6.65 13.78 Meanwhile The phthalocyanine compound having no halogen introduced is 4-nitrophthalonitrile or 3-nitrophthalonitrile, which is a generally well-known method,
Since it is possible to obtain a phthalonitrile having a phenol derivative substituted at the 4-position or 3-position by reacting with a phenol derivative, the phthalonitrile thus obtained can be synthesized by a usual method for obtaining phthalocyanine.

Production Example of Exemplified Compound (4) Step (a) Synthesis of 4- (2-Methyl-6- {3 ', 6'-oxaheptyloxycarbonyl} -phenoxyphthalonitrile In a 100 ml four-necked flask. , 4-nitrophthalonitrile 8.66 g (50 mmol), 2,3-cresotinic acid 2- (2-methoxyethoxy) ethyl ester 1
5.3 g (60 mmol), dimethyl sulfoxide 60
and 40 ml of 1,4-dioxane.
The reaction was carried out at 6 ° C. for 6 hours. After the reaction is completed, the reaction mixture is
0 ml of water, and the precipitated solid content was further
Washed with 0 ml. Then, the obtained cake is dried, and then purified by column chromatography using chloroform as a developing solvent, thereby obtaining a white solid as a target substance.
5 g (43.4 mmol) were obtained. (Yield, 86.8% based on 4-nitrophthalonitrile).

[0077] Step (b) Synthesis of Phthalocyanine of Exemplified Compound (4) In a 100 ml four-necked flask, 4- (2-methyl-
6- {3 ', 6'-oxaheptyloxycarbonyl}
8.00 g (21.0 mm) of phenoxyphthalonitrile
ol), 0.99 g of vanadium trichloride (6.30 mmol)
1) and 30 ml of benzonitrile were charged and 175 ° C
For 6 hours. After the completion of the reaction, the insolubles were filtered off, the solvent was distilled off, and the residue was washed twice with 200 ml of methanol to give 6.61 g (4.16) of the desired green cake.
mmol). (Yield, 7 for phthalonitrile
9.3%).

Maximum absorption wavelength 710.0 nm in ethyl cellosolve (ε = 1.53)
× 10 ⁵ ) Solubility 8% by weight to ethyl cellosolve The present invention provides a color filter containing a phthalocyanine compound and a resin, and as the resin used for the color filter of the present invention, all known resins can be mentioned. For example, polyamide resin, polyester resin, polycarbonate resin, polyether resin, polyolefin resin, polysulfone resin, polystyrene resin, polyvinyl chloride resin, polyvinylidene chloride resin, polyvinyl acetate resin, ethylene-vinyl acetate copolymer, acrylic Resin, ionomer resin, polyphenylene sulfide resin, styrene copolymer resin, fluorine resin, phenol resin, urea resin, melamine resin, epoxy resin, unsaturated polyester resin, diallyl phthalate resin, silicone resin, alkyd resin, polyimide resin, polyurethane resin, A xylene resin or the like can be used alone or as a mixture. Among these resins, acrylic resin is preferable. By using an acrylic resin, the solubility of the phthalocyanine compound in the resin is increased, and as a result,
It is possible to provide a resin composition containing a phthalocyanine compound at a high concentration and having high transparency. As a result, the light resistance and the absorption wavelength of the resin composition are more effectively controlled.

The acrylic resin is preferably a resin in which the monomers and oligomers constituting the acrylic resin are the following compounds. That is, acrylic acid, methacrylic acid, 2-hydroxyethyl acrylate, 2-hydroxyethyl methacrylate, 2-hydroxypropyl acrylate,
2-hydroxypropyl methacrylate, acrylamide, methacrylamide, N-hydroxymethyl acrylamide, polyethylene glycol diacrylate, trimethylolpropane triacrylate, trimethylolpropane trimethacrylate, pentaerythritol triacrylate, styrene, vinyl acetate, various acrylic esters, various Examples thereof include methacrylic acid ester, acrylonitrile, dipentaerythritol hexaacrylate, hexaacrylate of a caprolactone adduct of dipentaerythritol hexaacrylate, melamine acrylate, and epoxy acrylate prepolymer. Among these, especially (meth) acrylic acid, hydroxyalkyl (meth) acrylate, acrylic resin composed of various alkyl (meth) acrylates, (meth) acrylic acid, hydroxyalkyl (meth) acrylate, composed of various alkyl (meth) acrylates, and styrene An acrylic resin composed of acrylic resin, (meth) acrylic acid, and various alkyl (meth) acrylates is preferable.

Specific examples of preferable acrylic resins include the following. Resin (1) Resin having a weight average molecular weight of 10,000 to 100,000 consisting of the following monomer composition Styrene 5 mol% 2-hydroxyethyl methacrylate 22 mol% Ethyl methacrylate 54 mol% Methacrylic acid 19 mol% Resin (2) The following monomer composition Resin having a weight average molecular weight of 10,000 to 100,000 Styrene 62 mol% Diethylene glycol monoethyl ether acrylate 32 mol% Acrylic acid 6 mol% Resin (3) Resin having a weight average molecular weight 10,000 to 100,000 composed of the following monomer composition Methacrylic acid Benzyl 70 mol% Methacrylic acid 30 mol% These specific production examples are shown below. In the following production examples, "parts" represent parts by weight unless otherwise specified.

Production Example (1) Production Example of Resin (1) In a 1-liter four-necked flask, 175.0 parts of diethylene glycol dimethyl ether, 8.8 parts of styrene, 43.8 parts of 2-hydroxyethyl methacrylate and 43.8 parts of methacrylic acid were added. 26.3 parts and 96.3 parts of ethyl methacrylate were charged and heated to 90 ° C., and 145.0 parts of diethylene glycol dimethyl ether, 8.8 parts of styrene, 43.8 parts of 2-hydroxyethyl methacrylate and 43.8 parts of methacrylic acid were prepared in advance. A mixture of 3 parts and 96.3 parts of ethyl methacrylate and 2.92 parts of Nyper BMT (manufactured by NOF Corporation) was mixed and dissolved in 3 hours, and reacted at 90 ° C. for 3 hours. Further, 1.75 parts of Nyper BMT dissolved in 10 parts of diethylene glycol dimethyl ether was added, and the reaction was continued for 1 hour to obtain a solution of resin (1) in diethylene glycol dimethyl ether.

Production Example of Resin (2) A 1-liter four-necked flask was charged with 17 parts of cellosolve acetate.
5.0 parts, 113.8 parts of styrene, 19.6 parts of diethylene glycol monoethyl ether acrylate and 41.3 parts of acrylic acid were charged, heated to 90 ° C., and 175.0 parts of cellosolve acetate and 113.8 parts of styrene were prepared in advance. ,
19.6 parts of diethylene glycol monoethyl ether acrylate and 41.3 parts of acrylic acid and Niper BM
A mixture of 2.92 parts of T (manufactured by Nippon Oil & Fats Co., Ltd.) was dissolved in 3 hours, and the mixture was allowed to react for 3 hours at 90 ° C. Further, a solution obtained by dissolving 1.75 parts of Niper BMT in 10 parts of diethylene glycol dimethyl ether was added,
The reaction was continued for 1 hour to obtain a solution of resin (2) in cellosolve acetate.

Production Example of Resin (3) A 1-liter four-necked flask was charged with cellosolve acetate 17
5.0 parts, 144.7 parts of benzyl methacrylate and 30.3 parts of methacrylic acid were charged and heated to 90 ° C., and 175.0 parts of cellosolve acetate and benzyl methacrylate were added in advance.
4.7 parts, 30.3 parts of methacrylic acid and Niper BM
A mixture of 2.92 parts of T (manufactured by NOF Corporation) was dissolved in 3
The temperature was adjusted appropriately, and the reaction was carried out at 90 ° C. for 3 hours. further,
A solution prepared by dissolving 1.75 parts of Nyper BMT in 10 parts of diethylene glycol dimethyl ether was added, and the reaction was continued for 1 hour to obtain a cellosolve acetate solution of the resin (3).

Since the phthalocyanine compound of the present invention has a high solubility in a resin, a resin having a higher molecular weight than the conventional one can be used. Specifically, 30,000 or more, for example, 10
It is possible to use a high molecular weight resin of about 10,000 to 200,000. In a conventional color filter in which a pigment is dispersed in a resin, the molecular weight of the resin used is limited to about tens of thousands in view of the dispersibility of the pigment. Therefore, there is a problem in the heat resistance and solvent resistance of the obtained color filter, and it is necessary to increase the amount of the crosslinking agent with respect to the resin or to use a special crosslinking agent. On the other hand, in the phthalocyanine compound of the present invention, by combining with a high molecular weight resin, the amount of the cross-linking agent is increased, or a color filter excellent in heat resistance and solvent resistance is produced without using a special cross-linking agent. It is possible to

The resin contained in the color filter of the present invention is preferably a photosensitive resin.

The photosensitive resin may be any resin composition that undergoes a chemical reaction under the action of light, resulting in a change in the solubility or affinity for a solvent, or a change from a liquid state to a solid state. Aromatic diazonium salt resin, o-quinonediazide resin, bisazide resin, photodegradable photosensitive resin such as polysilane, photodimerization photosensitive resin such as cinnamic acid resin, unsaturated polyester resin, epoxy acrylic ester, Photopolymerization type photosensitivity of polyvinyl alcohol, polyamide, polymethacrylic acid ester, etc. as a prepolymer or binder polymer of urethane acrylic acid ester, etc. and various acrylic acid ester or methacrylic acid ester monomers and photopolymerization initiator added Resin can be mentioned,
Of these, photopolymerizable photosensitive resins are preferable. In particular, the binder polymer is an acrylic resin, and a resin composed of various (meth) acrylic acid ester monomers and a photopolymerization initiator is preferable. Examples of the photopolymerization initiator in the photosensitive resin include benzoin alkyl ether compounds, acetophenone compounds, benzophenone compounds, phenylketone compounds, thioxanthone compounds, and anthraquinone compounds.

Specific examples of preferable photosensitive resins include:
For example, the following are mentioned.

Photosensitive resin (1) compounding composition Binder resin Resin (1) 61 parts Monomer trimethylol chlorotrimethacrylate 36 parts Photopolymerization initiator Irgacure 907 4 parts Photosensitive resin (2) compounding composition Binder resin Resin (2) 57 parts Monomer pentaerythritol tetraacrylate 41 parts Photoinitiator 4- (pN, N-diethoxycarbenylethyl-2,6-di (trichloromethyl) -s-triazine) 2 parts Photosensitive resin (3) Blend composition Binder Resin Resin (3) 57 parts Monomer pentaerythritol tetraacrylate 41 parts Photopolymerization initiator 4- (pN, N-diethoxycarbenylethyl-2,6-di (trichloromethyl) -s-triazine) 2 parts These photosensitive materials For the resin, add the monomer and photopolymerization initiator to the solution of the corresponding binder resin. It is the solution, after a uniform solution can be prepared by evaporating the solvent.

The dye for the color filter of the present invention includes
If necessary, known pigments and dyes can be mixed in addition to the phthalocyanine compound. Examples of the pigment include inorganic pigments such as barium sulfate, zinc white, lead sulfate, titanium oxide, yellow lead, red iron oxide, ultramarine blue, navy blue, chromium oxide, and carbon black. The color index (CI) numbers are shown below. There are also organic pigments.

Yellow pigment: C.I. I. Pigment Yellow 2
0, C.I. I. Pigment Yellow 24, C.I. I. Pigment yellow 83, C.I. I. Pigment Yellow 86,
C. I. Pigment Yellow 93, C.I. I. Pigment yellow 109, C.I. I. Pigment Yellow 110,
C. I. Pigment Yellow 117, C.I. I. Pigment Yellow 125, C.I. I. Pigment Yellow 13
7, C.I. I. Pigment yellow 138, C.I. I. Pigment Yellow 139, C.I. I. Pigment Yellow 1
47, C.I. I. Pigment Yellow 148, C.I. I. Pigment yellow 153, C.I. I. Pigment yellow 154, C.I. I. Pigment yellow 166, C.I. I.
Pigment Yellow 168 Orange Pigment: C.I. I. Pigment Orange 36, C.I.
I. Pigment Orange 43, C.I. I. Pigment Orange 51, C.I. I. Pigment Orange 55, C.I. I.
Pigment Orange 59, C.I. I. Pigment Orange 61 Red Pigment: C.I. I. Pigment Red 9, C.I. I. Pigment Red 97, C.I. I. Pigment Red 122,
C. I. Pigment Red 123, C.I. I. Pigment Red 149, C.I. I. Pigment Red 168, C.I.
I. Pigment Red 177, C.I. I. Pigment Red 180, C.I. I. Pigment Red 192, C.I. I.
Pigment Red 215, C.I. I. Pigment Red 2
16, C.I. I. Pigment Red 217, C.I. I. Pigment Red 220, C.I. I. Pigment Red 22
3, C.I. I. Pigment Red 224, C.I. I. Pigment Red 226, C.I. I. Pigment Red 227,
C. I. Pigment Red 228, C.I. I. Pigment Red 240, C.I. I. Pigment Red 48: 1 Violet Pigment: C.I. I. Pigment Violet 1
9, C.I. I. Pigment Violet 23, C.I. I. Pigment Violet 29, C.I. I. Pigment Violet 30, C.I. I. Pigment Violet 37,
C. I. Pigment Violet 40, C.I. I. Pigment Violet 50 Blue Pigment: C.I. I. Pigment Blue 15, C.I. I. Pigment Blue 15: 6, C.I. I. Pigment Blue 2
2, C.I. I. Pigment Blue 60, C.I. I. Pigment Blue 64 Green Pigment: C.I. I. Pigment Green 7, C.I. I. Pigment Green 36 Brown Pigment: C.I. I. Pigment Brown 23, C.I.
I. Pigment Brown 25, C.I. I. Pigment Brown 26 Black pigment: C.I. I. Pigment Black 7 and the like.

Examples of the dye include C.I. I. Acid Yellow 11, C.I. I. Acid Orange 7, C.I. I.
Acid Red 37, C.I. I. Acid Blue 29,
C. I. Acid Red 180, C.I. I. Direct Red 28, C.I. I. Direct Yellow 12, C.I. I.
Direct Orange 26, C.I. I. Direct Green 59, C.I. I. Direct Green 28, C.I. I. Direct Red 83, C.I. I. Reactive Yellow 2,
C. I. Reactive Red 17, C.I. I. Reactive Black 5, C.I. I. Reactive Red 120,
C. I. Disperse Orange 5, C.I. I. Disperse thread 58, C.I. I. Disperse Blue 165,
C. I. Basic Blue 41, C.I. I. Basic Red 18, C.I. I. Mordant Red 7, C.I. I. Moldant Black 7, C.I. I. Azo dyes such as Moldant Yellow 5, C.I. I. Bat Blue 4, C.I. I. Acid Blue 40, C.I. I. Acid Green 25, C.I.
I. Reactive Blue 19, C.I. I. Reactive Blue 49, C.I. I. Disperse Red 60, C.I. I.
Disperse Blue 56, C.I. I. Anthraquinone dyes such as Disperse Blue 60, C.I. I. Indigo dyes such as Pad Blue 5, C.I. I. Phthalocyanine dyes such as Direct Blue 86, C.I. I. Basic Blue 3, C.I. I. Quinone imine dyes such as Basic Blue 9, C.I. I. Solvent Yellow 33, C.I.
I. Acid Yellow 3, C.I. I. Quinoline dyes such as Disperse Yellow 64, C.I. I. Acid Yellow 1, C.I. I. Acid Orange 3, C.I. I. Examples thereof include nitro dyes such as Disperse Yellow 42, carbonyl dyes and methine dyes. Dyes are preferred from the viewpoint of solubility in resins. Particularly highly soluble fluorine-containing compounds, for example, fluorine-containing phthalocyanine compounds (JP-A-5-222302 and JP-A-5-345).
861, JP-A-6-107663, JP-A-6-22.
No. 8533, JP-A-6-328856, JP-A7-1
18551, JP-A-7-118552, JP-A-6-
262927) and fluorine-containing anthraquinone compounds (Japanese Patent Application Laid-Open No. 7-92568, Japanese Patent Application No. 7-24814).
No. 0) is preferable. A fluorine-containing anthraquinone compound is more preferable.

The method for producing the resin composition for a color filter of the present invention is not particularly limited, but the following methods may be mentioned, for example.

(1) A method of mixing the phthalocyanine compound of the present invention alone or with other dyes, and mixing with the thermoplastic resin melted by heating.

(2) A method in which the phthalocyanine compound of the present invention is mixed alone or with other dyes, dissolved in a solvent together with a resin and mixed, and then the solvent is volatilized.

(3) A method in which the phthalocyanine compound of the present invention is used alone or in admixture with another dye, and is mixed with a polymerizable vinyl compound that is a precursor of a resin, and the mixed solution is polymerized.

In the present invention, the present inventors have found that a color filter using the resin composition containing the phthalocyanine compound as a colored resist can exhibit excellent effects.

The method for producing the color filter of the present invention is not particularly limited and can be applied to the conventionally proposed pigment-based production method. Since the phthalocyanine compound of the present invention has a high solubility in a resin, it is possible to manufacture a color filter having a transparent feeling and a high contrast when applied to any method.

The following method can be mentioned as a method in which the phthalocyanine compound of the present invention is applied to the conventional method.

(1) The resin composition containing the phthalocyanine compound of the present invention is used to form a resist, which is applied on a transparent substrate, exposed and developed to form a first colored pattern. A method of obtaining a three-color pattern by repeating this step three times.

(2) A method for obtaining a colored pattern by etching the polyimide resin composition containing the phthalocyanine compound of the present invention.

(3) Using the epoxy resin composition containing the phthalocyanine compound of the present invention as a coloring ink, a color pattern is directly formed on a glass substrate by an offset printing machine. A method of obtaining a three-color pattern by repeating this step three times.

(4) The ITO electrode patterned in a predetermined shape on a glass substrate is used as one electrode and immersed in an electrodeposition liquid made of a resin composition containing the phthalocyanine compound of the present invention to form a first colored film on the electrode. Let out. A method of forming a pattern by repeating this step three times.

In addition to being applicable to the above conventional method, it is also applicable to the following method proposed as a new manufacturing method.

(5) Three color films coated with a resist resin in which a dye is dispersed are attached to glass substrates, respectively,
A method in which a color filter is formed when peeled.

(6) A method of selectively coloring a polysilane film by a sol-gel method using a colored silica sol.

In the above method (1), the dye layer can be patterned on an optically transparent substrate, and the dye layer can be patterned on the substrate to be used, and the formed color filter is a predetermined color filter. There is no particular limitation as long as it has the function of. For example, glass plate, polyvinyl alcohol, hydroxyethyl cellulose, methyl methacrylate, polyester, butyral, polyamide, polyethylene, vinyl chloride, vinylidene chloride, polycarbonate, polyolefin copolymer resin, vinyl chloride copolymer resin, vinylidene chloride copolymer resin, styrene copolymer A resin film or plate such as a resin may be used. It is also possible to form a patterned dye layer integrally with a dye applied as a color filter.

[0107]

The present invention is described in detail below with reference to examples, but the present invention is not limited to these.

Example 1 5 g of the above phthalocyanine compound (3) was dissolved in 25 g of a diethylene glycol dimethyl ether solution (nonvolatile content 20%) of the above photosensitive resin (1), and the solution was placed on a glass substrate.
It was spin-coated with a spin coater so that the film thickness after solvent drying was 2 μm. Next, after prebaking at 60 ° C. for 20 minutes, exposure was performed using a photomask for pattern formation. After developing with a 1% aqueous solution of sodium carbonate and washing with pure water, post-baking was performed at 200 ° C. for 10 minutes to produce a green color filter.

The depolarization characteristics, the transmittance characteristics, the light resistance and the heat resistance of this color filter were evaluated. The results are shown in Table 18.

Example 2 Instead of the compound (3) in Example 1, the compound (4) was used.
Using a photosensitive resin (2) instead of the photosensitive resin (1)
A green color filter was produced in the same manner as in Example 1 except that was used. The depolarization characteristics, the transmittance characteristics, the light resistance and the heat resistance of this color filter were evaluated. The results are shown in Table 18.

Example 3 Instead of the compound (3) in Example 1, the compound (1
A green color filter was produced in the same manner as in Example 1 except that 2) was used and the photosensitive resin (3) was used instead of the photosensitive resin (1). The depolarization characteristics, the transmittance characteristics, the light resistance and the heat resistance of this color filter were evaluated. The results are shown in Table 18.

Example 4 Instead of the compound (3) in Example 1, the compound (1
A green color filter was produced in the same manner as in Example 1 except that 8) was used. The depolarization characteristics, the transmittance characteristics, the light resistance and the heat resistance of this color filter were evaluated. The results are shown in Table 18.

Example 5 Instead of the compound (3) in Example 1, the compound (2
A green color filter was produced in the same manner as in Example 1 except that 3) was used and the photosensitive resin (2) was used instead of the photosensitive resin (1). The depolarization characteristics, the transmittance characteristics, the light resistance and the heat resistance of this color filter were evaluated. The results are shown in Table 18.

Example 6 Instead of the compound (3) in Example 1, the compound (2
A green color filter was produced in the same manner as in Example 1 except that 8) was used and the photosensitive resin (3) was used instead of the photosensitive resin (1). The depolarization characteristics, the transmittance characteristics, the light resistance and the heat resistance of this color filter were evaluated. The results are shown in Table 18.

Example 7 Instead of the compound (3) in Example 1, the compound (3
A green color filter was produced in the same manner as in Example 1 except that 7) was used. The depolarization characteristics, the transmittance characteristics, the light resistance and the heat resistance of this color filter were evaluated. The results are shown in Table 18.

Example 8 Instead of the compound (3) in Example 1, the compound (4
0) was used, and a photosensitive resin (2) was used in place of the photosensitive resin (1), and a green color filter was produced in the same manner as in Example 1. The depolarization characteristics, the transmittance characteristics, the light resistance and the heat resistance of this color filter were evaluated. The results are shown in Table 18.

Example 9 Instead of the compound (3) in Example 1, the compound (4
A green color filter was produced in the same manner as in Example 1 except that 1) was used and the photosensitive resin (3) was used instead of the photosensitive resin (1). The depolarization characteristics, the transmittance characteristics, the light resistance and the heat resistance of this color filter were evaluated. The results are shown in Table 18.

The depolarization characteristic was evaluated by the following method. The prepared color filter sample was sandwiched between two polarizing plates, and the ratio (contrast ratio) of the amount of transmitted light was measured when the polarization axes of the two polarizing plates were parallel and orthogonal. The following two-stage evaluation was performed based on the measurement results.

Contrast ratio of 2000 times or more × Contrast ratio of less than 2000 times The transmittance characteristics of the sample were measured in the range of 400 to 700 nm, and the following three grades were evaluated according to the measurement results. .

Green color filter: ○ When the transmittance at 545 nm is 80%, it is 460 nm
And when the transmittance at 610 nm is less than 10%. When the transmittance at 545 nm is 80%, 460 nm.
And the transmittance at 610 nm is 10% or more and less than 20% × When the transmittance at 545 nm is 80%, 460 nm
And the transmittance at 610 nm is 20% or more Blue color filter: ○ When the transmittance at 460 nm is 80%, 545 nm
And when the transmittance at 610 nm is less than 10%. When the transmittance at 460 nm is 80%, 545 nm.
And when the transmittance at 610 nm is 10% or more and less than 20% x When the transmittance at 460 nm is 80%, 545 nm
And the transmittance at 610 nm is 20% or more. Further, the light resistance of the sample is measured with a xenon light resistance tester (irradiation light amount 1
It was set to 100,000 lux), and the following three grades were evaluated based on the residual rate of the absorbance over time.

○ Remaining rate of absorbance after 100 hours is 80% or more. △ Remaining rate of absorbance after 100 hours is 30% or more.
Less than 80% x less than 30% residual rate of absorbance after 100 hours Further, the heat resistance was evaluated by the following three stages based on the residual rate of absorbance after heating the sample at 200 ° C for 1 hour with a hot air dryer.

Absorbance residual rate of 80% or more Δ Absorbance residual rate of 30% or more to less than 80% × Absorbance residual rate of less than 30%

[0123]

[Table 18]

[0124]

The color filter according to the present invention comprises a phthalocyanine compound represented by the general formula (1), which has absorption in the visible light region of 400 to 700 nm and has excellent solubility in resin and excellent light resistance or heat resistance. Since it is contained, it is extremely excellent in depolarization characteristics, transmittance characteristics, light resistance and heat resistance.

Claims (5)

[Claims] 1. The benzene nucleus of a phthalocyanine skeleton
A color filter comprising a phthalocyanine compound in which 1 to 8 of the substitutable positions are substituted with a phenoxy group having a substituent at one or both of the ortho positions. 2. The color filter according to claim 1, wherein among the atoms contained in the substituent at the ortho position of the phenoxy group, the total atomic radius of atoms excluding hydrogen atoms is 3.0 angstroms or more. 3. A compound of the general formula (1) {However, in the formula (1), X represents at least one atom selected from a hydrogen atom and a halogen atom, and Y represents a compound represented by the general formula (2): (In the formula, R ¹ , R ² , R ³ , R ⁴ and R ⁵ each independently represent a linear, branched or cyclic alkyl group having 1 to 20 carbon atoms or an aryl group which may be substituted. , R ⁶
Represents an aryl group which may be substituted, A represents a CH group or a nitrogen atom, B represents an oxygen atom, a sulfur atom, CH
₂ groups, an NH group or an alkylamino group having 1 to 4 carbon atoms, f, g, h and j are integers of 1 to 5, i and k are integers of 0 to 6 and 1 and m is independently an integer of 1 to 4), at least one substituent selected from W, W represents at least one substituent selected from a halogen atom and / or Z, and e
Is an integer of 0 to 4. ] Represents a phenoxy group having a substituent at the ortho position, a to d are integers from 0 to 4, the sum of a to d is an integer from 1 to 8, and M is a metal or a metal oxide. , Represents a metal halide. } The color filter according to claim 1 or 2, which comprises a phthalocyanine compound represented by the following formula. 4. The color filter according to claim 1, comprising a phthalocyanine compound and a resin. 5. The color filter according to claim 4, wherein the resin is a photosensitive resin.