TWI300794B - Color filter - Google Patents

Description

1300794 V. Technical Description [Technical Field] The present invention relates to a color filter material having a halogenated metal phthalocyanine pigment. [Background Art] A color filter material which can be used in a liquid crystal display device is in a glass or the like. Various pixel regions of three colors of red, green, and blue are formed on the transparent substrate; in order to form a green pixel region, a copper halide phthalocyanine dye or a copper halide phthalocyanine pigment is generally used. [Problem to be Solved by the Invention] A green colorant which is a green pixel region constituting a color filter material may be used, and one or more halogen atoms in each phthalocyanine molecule are bonded to a phthalocyanine molecule. A dye or pigment of a halogenated metal phthalocyanine structure on a benzene ring. However, in a wide range of applications such as lithography, paint, and coloring of molded articles, and in the field of different color filter materials, not only the coloring requirements alone but also higher (1) to (2), for example, are required. Characteristics: (1) High selectivity to light passing only a specific wavelength; (2) Light of a specific wavelength at a very high transmittance. It can be used as such a green dye coloring agent, such as the technique disclosed in Japanese Laid-Open Patent Publication No. SHO63-286801, which is an octachloro copper phthalocyanine sulfuric acid dye, an octachloronickel phthalocyanine sulfuric acid dye, or octachloroguanidine. A halogenated metal phthalocyanine sulfuric acid material such as a cyanine sulfate dye and a yellow organic dye. Further, Japanese Laid-Open Patent Publication No. Hei 11-302283 discloses an octaphenyl copper phthalocyanine acid dye, an octaphenyl zinc phthalocyanine sulfuric acid dye, and an octabenzene 1300794. The invention (2: base aluminum phthalocyanine) A phthalic acid phthalocyanine-based sulphuric acid-based phthalic acid phthalocyanine-based phthalic acid phthalocyanine-based phthalocyanine-based phthalocyanine-based phthalocyanine-based phthalocyanine-based phthalocyanine-based phthalocyanine-based phthalocyanine-based phthalocyanine-based phthalocyanine Techniques of dyes and zinc phthalocyanine green dyes having a sulfate group and a monoazo dye residue, etc. However, such dyes have the disadvantages of various durability such as light resistance and the like, and have a small number of disadvantages as described above. The green dye is usually a copper halide phthalocyanine pigment which is substituted with a halogen atom such as bromine chlorine by using a total of 16 hydrogen atoms on each of the four benzene rings of one phthalocyanine molecule. Cyanine pigment, which is replaced by a hydrogen atom and a chlorine atom and/or a chlorine atom. The copper halide phthalocyanine pigment is entangled in a mixture of various ratios on the green pixel region of the color filter material, and usually requires a green pigment which is stronger than the yellow color. It has always been green to emit a bright yellow color. It is preferable that the halogen atom bonded to the benzene ring of one molecule of the copper phthalocyanine phthalocyanine is more and that the number of bromine atoms in the halogen atom bonded to one molecule of the copper phthalocyanine is known to be large. The method of using a large amount of a copper halide phthalocyanine pigment, such as C.I. Pigment Green 36, is proposed in the green pixel region of the color filter material. A total of 16 hydrogen atoms are present on the four benzene rings of the molecular copper halide phthalocyanine, which is a copper halide phthalocyanine phthalocyanine made from a copper phthalocyanine containing a high proportion of the bromine atom. 0 1300794 V. INSTRUCTIONS (3) In addition, in order to improve the green color with a phase close to the color of the color, in the special Kaiping 1 0 - 1 No. 60928 and the like have proposed to add a yellow pigment such as CI Pigment Yellow 150 or CI Pigment Yellow 185 to the green pigment of c. I. Pigment Green 36 Temple to strengthen yellow. However, now, as a liquid crystal display device For the backlight source, a three-wavelength tube having a green light main bright line of about 545 nm is often used; in the case of using a liquid crystal display device using such a light source, when using a color filter material obtained according to a conventional technique, Has the problem points described below. In other words, the use of the color filter material of the representative green dye, such as the above-mentioned Japanese Patent Publication No. 63-286801, has a so-called fundamental disadvantage such as poor light resistance and fading of the hue due to long-term use. Further, the green pixel region of the color filter material produced by using the green pigment of CI Pigment Green 3 6 described in JP-A-9-68607 cannot obtain a red pixel region and a green pixel as suitable for combination use. The color and hue of the district. Further, as represented by the Japanese Patent Publication No. Hei 10-0160, and the like, it has been proposed to use a yellow pigment to which CI Pigment Green 36 is added, and it is intended to approximate the chromaticity and hue to the green pixel region, but in order to achieve For this purpose, the amount of yellow pigment added to the green pigment is increased, so that the desired chromaticity and hue cannot be generated in the pixel region. In order to form a pixel region, a yellow pigment and a green pigment which are used when storing a photocurable composition as described later are used, and chromatic aberration is caused. 1300794 V. INSTRUCTIONS (4) Results 'The color filter material having such a pixel region is not only insufficient in brightness on the liquid crystal display, but also has the disadvantage of having to use a large number of light sources in order to achieve a satisfactory display, or The shortcomings of the desired chromaticity and hue cannot be generated in the pixel area. DISCLOSURE OF THE INVENTION The problem to be solved by the present invention is to provide a color filter material which has durability superior to dye color filter color, and is suitable for use in a green light main line having about 545 nm. In the case of a liquid crystal display having a wavelength tube as a light source, it can exhibit a strong yellow color, a bright green color, and can be displayed in a bright liquid state under a backlight having a minimum amount of light. Therefore, the inventors of the present invention synthesize various halogenated metal phthalocyanine pigments having characteristics superior to those of conventional halogenated copper phthalocyanine pigments for forming a green pixel region of a color filter material, and measuring their spectral transmission spectra and reviewing The appropriateness of the green pixel area. In the case of a three-wavelength tube used in an actual liquid crystal display device, when an optimum light-emitting wavelength suitable for each color filter material is formed, it is a complicated operation to take out and evaluate the light-emitting wavelength. Therefore, in view of the fact that the green light main line of the three-wavelength tube is about 545 nm, the main bright line of 545 nm is specified by the Japanese Industrial Standard (IS) Z 8719, which is the same classification as the three-wavelength tube. The fluorescent light source F10 light source of the 3-wavelength domain illumination form is replaced and used as a three-wavelength tube for evaluation on an actual liquid crystal display device. The result is found and provides a 520-590 nm in the spectral transmission spectrum. The specific halogenated metal phthalocyanine which shows the maximum penetration rate. 1300794 V. Illustrative (5) The coloring agent used to form the green pixel area, and provides a bright yellow, bright green color. The liquid crystal display has heretofore completed the present invention. That is, the present invention provides a color filter material characterized in that the color filter material is on a transparent substrate having various pixel regions of red, green, and blue, and the green pixel region is (1) containing each a halogenated metal phthalocyanine pigment bonded to a benzene ring of a phthalocyanine molecule by 8 to 16 halogen atoms in a phthalocyanine molecule; and (2) displayed at 520 to 590 nm in a spectroscopic light-transmitting spectrum of the entire visible light region Maximum penetration rate. BRIEF DESCRIPTION OF THE DRAWINGS Fig. 1 is a light transmission spectrum of the green pixel region of the color filter obtained in Example 1. Fig. 2 is a light transmission spectrum of the green pixel region of the color filter obtained in Example 3. Fig. 3 is a light transmission spectrum of the green pixel region of the color filter obtained in Comparative Example 1. [Embodiment of the Invention] Hereinafter, the present invention will be described in detail. The present invention satisfies the requirements of the foregoing (1) and (2). These requirements are explained in turn below. The pigment used in the present invention which satisfies the requirements of the above (1) is a chemical structure containing a phthalocyanine molecule (structure), and each of the phthalocyanine molecules (structure) has a total of 8 to 16 halogen atom bonds. A substance that is attached to four benzene rings 1300794 5. The pigment of the invention (6). Hereinafter, these are the halogenated metal phthalocyanine pigments used in the present invention. The more suitable halogenated metal phthalocyanine pigment used in the present invention is exemplified by, for example, the following two groups of halogenated metal phthalocyanine pigments. (first group) having a metal group selected from the group consisting of Al, Si, Sc, Ti, V, Mg, Fe, Co, Ni, Zn, Ga, Ge, Y, Zr, In, Nb, Sn, and Pb a central metal, 8 to 16 halogen atoms in each phthalocyanine molecule bonded to a halogenated metal phthalocyanine pigment on a phthalene ring of a phthalocyanine molecule; when the central metal is trivalent, the central metal system One of a halogen atom, a hydroxyl group or a sulfuric acid group; when the central metal is tetravalent, the central metal may be the same or different from one oxygen atom or two halogen atoms, a hydroxyl group or A halogenated metal phthalocyanine bonded to any one of the sulfate groups. (Second group) A trivalent metal selected from the group consisting of Al, Sc, Ga, Y, and In as a central metal, and 8 to 16 halogen atom bonds in each phthalocyanine molecule a halogenated metal phthalocyanine bonded to a benzene ring of a phthalocyanine molecule as a constituent unit; each central metal of the constituent unit is composed of an oxygen atom, a sulfur atom, a sulfinyl-S0-, and a sulfonyl-S02- A halogenated metal phthalocyanine pigment composed of a divalent atomic group-bonded halogenated metal phthalocyanine dimer selected from the group. In the halogenated metal phthalocyanine pigment used in the present invention, the halogen atom bonded to the benzene ring 1300794, and the invention (7) may be all the same, and any one of them may be different. Further, it is also possible to bond a different halogen atom to one benzene ring. When the number of halogen atoms bonded to the benzene ring is constant, the yellow odor on the left side becomes stronger in the order of the halogen atom of iodine > bromine > chlorine & fluorine. Therefore, the halogenated metal phthalocyanine pigment used in the present invention in which 9 to 15 halogen atoms of 8 to 16 halogen atoms in each phthalocyanine molecule are bonded to the benzene ring of the phthalocyanine molecule is a The yellow color is bright green, and it is most suitable for use on the green pixel area of the color filter material. The halogenated metal phthalocyanine pigment used in the present invention is insoluble or poorly soluble in water and an organic solvent. The halogenated metal phthalocyanine pigment used in the present invention includes any one of a pigment (also referred to as a crude pigment) which is not subjected to the following conditioning treatment, and a pigment which is subjected to a trimming treatment. The halogenated metal phthalocyanine pigment to which the first group and the second group belong can be represented by the following formula 1. Formula 1

1300794 V. INSTRUCTIONS (8) A group of halogenated metal phthalocyanine pigments, as shown in Formula 1, are described below. In the formula 1, it represents a hydrogen atom, a chlorine atom, a bromine atom, or an iodine atom. The four X atomic systems bonded to a benzene ring are the same or different. The bond is bonded to four or four benzene rings, and has 8 to 16 hydrogen atoms, chlorine atoms, bromine atoms, or iodine atoms. The μ system represents the center metal. The enthalpy and the number m thereof described later are in the range of the same halogenated metal phthalocyanine pigment, and the total number of hydrogen atoms, chlorine atoms, bromine atoms, or iodine atoms in 16 of Xi to X16 is less than 8, and the pigment is blue. A pigment having a total of 8 or more hydrogen atoms, chlorine atoms, bromine atoms, or ruthenium atoms in 16 Xi to X16 is stronger when the total amount is larger. Y, which is bonded to the central metal ruthenium, is one of a group of halogen atoms, oxygen atoms, hydroxyl groups and sulfonic acid groups selected from fluorine, chlorine, bromine or iodine; The number of Ys bonded to the center metal crucible, which is an integer of 0 to 2. The enthalpy of m can be determined by the atomic valence of the central metal ruthenium. When the central metal lanthanide is a valence of a trivalent atom such as A 1 , S c, G a, Y, I η , shell [J m = 1, from fluorine, chlorine, bromine, iodine, hydroxyl and sulfonate One of the groups selected from the group consisting of acid groups is bonded to the central metal. When the central metal lanthanide is a tetravalent atomic valence such as Si, Ti, V, Ge, Zi:, Sn, then m = 2, an oxygen linkage to the central metal; or from fluorine, chlorine, bromine The two groups selected from the group consisting of iodine, hydroxyl and sulfonic acid groups are bonded to the central metal. When the central metal lanthanide is a valence of two valences such as Mg, Fe, Co, Ni, Zn, -10- 1300794, and (9) Zr, Sn, and Pb, Y does not exist. Further, the halogenated metal phthalocyanine pigment to which the second group belongs is as shown in the general formula 1, and is explained below. In the formula 1, the definitions of Xi to X16 are the same as defined above. When the central metal lanthanum is a trivalent valence such as Al, Sc, Ga, Y, and In, then m = 1. The Y system represents the following atomic groups.

Further, in the chemical structure of the atomic group, the central metal system is the same as defined above. Χ17~Χ32 are the same as the definitions of the aforementioned Xi~X16 series. The A system represents a divalent atomic group selected from the group consisting of an oxygen atom, a sulfur atom, a sulfinyl group (-S0-), and a sulfonyl group (-S〇2-). The oxime of the oxime and the atomic group in the formula 1 means that the bond is bonded via a divalent atomic group. That is, the halogenated metal phthalocyanine pigment to which the second group belongs is a halogenated metal phthalocyanine having a molecular weight of 2-11-1300794, and is a constituent unit via the aforementioned divalent atomic group. Bonded metal halide phthalocyanine dimer. The halogenated metal phthalocyanine pigment represented by the formula 1 can be exemplified by, for example, the following 1 to 4. 1 having a divalent metal selected from the group consisting of Mg, Fe, Co, Ni, Zn, Zr, Sn, and Pb as a center such as a tin halide phthalocyanine, a nickel halide phthalocyanine, or a zinc halide phthalocyanine A metal, and 8 to 16 halogen atoms are a halogenated metal phthalocyanine pigment bonded to each of four benzene rings of one phthalocyanine molecule. 2 having a trivalent metal selected from the group consisting of Al, Sc, Ga, Y, and In as a central metal such as a halogenated chloroaluminum phthalocyanine having a halogen atom, a hydroxyl group, and a sulfonate on the center metal Any one of the acid groups, and 8 to 16 halogen atoms are bonded to the halogenated metal phthalocyanine pigment on each of the 4 benzene rings of one phthalocyanine molecule. 3 having a tetravalent metal selected from the group consisting of S i, Ti, V, Ge, Zr and Sn as a central metal such as a halogenated oxytitanium phthalocyanine or a vanadium oxyhalide phthalocyanine, having a central metal One oxygen atom may be the same or different, and may be any one of two halogen atoms, a hydroxyl group, and a sulfonic acid group, and 8 to 16 halogen atoms are bonded to each of 4 phthalocyanine molecules. A halogenated metal phthalocyanine pigment on a benzene ring. 4 consisting of a halogenated oxy-aluminum phthalocyanine dimer, a halogenated // sulphur-aluminum phthalocyanine dimer, selected from the group consisting of A 1 , S c, G a, Y and I η The trivalent metal selected from the group is used as the central metal, and 8 to 16 halogens-12-1300794. 5. Description of the invention (11) 2 molecules of the atomic system bonded to the 4 benzene rings of each phthalocyanine molecule As a constituent unit, each of the central metals of the constituent unit is via a divalent radical selected from the group consisting of an oxygen atom, a sulfur atom, a sulfinyl group (-S0-), and a sulfonyl group (-S02-). Bonded halogenated metal phthalocyanine pigment. Hereinafter, a method of producing a green pixel region and a color filter material from a halogenated metal phthalocyanine pigment used in accordance with the present invention, and a method of measuring a spectral light transmission spectrum of the green pixel region will be described. The green pixel region containing the halogenated metal phthalocyanine pigment used in accordance with the present invention is a method for determining the wavelength of the maximum transmittance in the spectral transmission spectrum in the entire visible light region (380 to 780 nm) by the method described later ( Hereinafter, it is called Tmax), which is close to 545 nm on the long wavelength side, and because of the large transmittance in Tmax, it is possible to obtain a bright green color which is more yellow than the conventional copper halide phthalocyanine pigment. District. Moreover, in order to make a liquid crystal display device which can be more clearly displayed, it is preferable to have a high transmittance in T m a X, and it is preferable to use it at 70% or more. Among the halogenated metal phthalocyanine pigments used in the present invention, a halogenated chloroaluminum phthalocyanine pigment, a halogenated // oxy-aluminum phthalocyanine dimer pigment, and a zinc halide phthalocyanine pigment are preferred. The green pixel region containing these pigments has Tmax in the wavelength region near the green light wavelength of 545 nm of the aforementioned three-wavelength tube; since the transmittance of the Tmax is more than 85%, it is suitable for use of the three wavelengths. The liquid crystal display device of the tube can be displayed with a light source of at least a light amount. It can be seen from Fig. 1 and Fig. 3 that the green pixel region containing the halogenated chloroaluminum phthalocyanine pigment or the halogen-oxygen-aluminum phthalocyanine dimer pigment, which is halogenated-13-1300794, the invention (1 2 ), Compared with the green pixel region containing a copper halide phthalocyanine pigment, it has a wider range of high transmittance in the spectral transmission spectrum of the entire visible light region, and is therefore highly suitable for use in high-brightness objects. On the filter material of the device. 'It can be seen from Fig. 2 and Fig. 3 that the green pixel region containing the zinc halide phthalocyanine pigment is compared with the green pixel region containing the copper halide phthalocyanine pigment, and is spectrally transmitted through the spectrum of the visible light region. It has a relatively narrow wavelength range of high transmittance, and is therefore very suitable for use in a color filter of a device such as a high color gamut object. That is, the green pixel region containing the zinc halide phthalocyanine pigment can reduce the average particle diameter of the primary particles of the pigment such that Tmax is close to a high wavelength, and the transmittance at Tm ax may also become high. The green pixel region containing the zinc halide phthalocyanine pigment can also increase the average particle diameter of the primary particles of the pigment to be closer to the high wavelength side than the green pixel region containing the conventional copper halide phthalocyanine pigment. Tmax; however, when the penetration rate is interpolated at 1/2 of the Tmax in the spectral spectrum of the spectral transmission, the distance between the two points on the curve (the amplitude is half a 値) is 90 to 110 nm, which is very steep. High color purity, in the case of color mixing with yellow pigments, the amount of light penetration in the green area is increased to obtain a clear picture; the contrast of the image is good, so it is very suitable for use on high color purity filter materials. In addition, in general, in the comparison of the film thickness of the colored resin film of the plurality of color filter materials to be measured, the CIE color system chromaticity (Y, X, y) The larger one can be called "high color purity" -14- 1300794. V. Inventive Note (13); The film thickness of the colored resin film of the color filter material of a plurality of measurement objects determined according to X and y値 is constant In the comparison below, a film having a thin film thickness may be referred to as a "high color density", and a Y" being a large one may be referred to as a "high transparency". Further, in the comparison of the average particle diameters of the same primary particles, the zinc halide phthalocyanine pigment is characterized in that it has a coloring power higher than that of the green pixel region containing the copper halide phthalocyanine pigment by 10% or more. That is, in the case where the green color region of the color filter of the same transmittance is obtained in the same colored resin film, the advantage of the colorant content can be lowered. On the contrary, the zinc halide phthalocyanine pigment used in accordance with the present invention can appropriately thin the green pixel region of the color filter material. Further, it can be used as a green pixel region of a color filter material, and it is preferably a region in which the light transmittance of 650 to 700 nm is wider and the transmittance is larger than 5% or less, and the maximum transmittance ratio is large. When the split light transmission rate in such a wavelength region is low, it means that the color filter material having a small amount of red light penetration on the green pixel region is also excellent. It can be used as the halogenated metal phthalocyanine pigment used in the present invention, and it is preferred to use the kind of the central metal, the kind and number of the groups bonded to the central metal, and the bonding of each of the four molecules of phthalocyanine. The type of the halogen atom on the benzene ring and the number of bonds thereof are a single one of only one type of halogenated metal phthalocyanine pigment; however, it is also possible to measure two or more kinds of the above-mentioned central metal into a different halogenated metal phthalocyanine. a mixture of pigments. For example, a halogenated chloroaluminum phthalocyanine pigment can be presumed to have the same effect as a halogenated oxy-aluminum phthalocyanine dimer pigment. Of course, you can use this. -15- 1300794 V. Description of Invention (彳4) The halogenated metal phthalocyanine pigment used in the present invention can be used, for example, in ""phthalocyanine compound", volume 2, π manufacturing and application" (", CRC Publishing Company, 1 983), etc., produced by methods such as the chlorosulfonic acid method and the hafnium halide method. Can be used as the chlorosulfonic acid method, for example, will have from Al, Si, Sc, Ti, V, Mg, Fe, Co, Ni, Zn, Ga, Ge, Υ, Zr, Nb, In The phthalocyanine pigment of the central metal selected from the group consisting of Sn and Pb is dissolved in a sulphate-based solvent such as chlorosulfonic acid, and chlorine, bromine, iodine or the like is put thereinto to be halogenated. As a halogenated carbonitrile method, for example, ""phthalocyanine compound", the second volume, π manufacturing and application", for example, a halogen atom such as chlorine or iodine other than bromine is used. a tannic acid or a phthalonitrile substituted for a part or all of a hydrogen atom on the benzene ring, and from Al, Si, Sc, Ti, V, Mg, Fe, Co, Ni, Zn, Ga, Ge, Y, Zr, Nb, A method of synthesizing a halogenated metal phthalocyanine pigment by using a metal or a metal salt selected from the group consisting of In, Sn, and Pb as a suitable starting material. In this case, a catalyst such as bismuth molybdate may be used as the case may be. The reaction temperature at this time is in the range of 100 to 300 ° C and is carried out for 1 to 30 hours. For example, it is a method of melting, such as an aluminum halide such as aluminum chloride or aluminum bromide, as in the case of the specification of U.S. Patent No. 5,071,534, the disclosure of which is incorporated herein by reference. For example, titanium halide such as titanium tetrachloride, such as alkali metal halide or alkaline earth metal halide such as sodium chloride or sodium bromide (hereinafter referred to as alkali (earth) metal halide), chlorosulfuric acid, etc. 16-1300794 V. INSTRUCTION OF THE INVENTION (15) A melt of about 10 to 170 ° C formed by one or a mixture of two or more kinds of solvent compounds in the form of halogenation is formed in the halogenating agent from Al. A method of halogenating a metal phthalocyanine pigment is selected from the group consisting of Si, Sc, Ti, V, Mg, Fe, Co, Ni, Zn, Ga, Ge, Y, Zr, Nb, In, Sn, and Pb. Aluminum halide suitable for use in the melt process is aluminum chloride. The amount of the aluminum halide added in the above method is usually 3 times the number of moles or more, more preferably 10 to 20 times the moles, based on the metal phthalocyanine pigment. The dimer pigment in the halogenated metal phthalocyanine pigment used in the present invention may, for example, be a hydroxyl group or a sulfur group having a central metal and a bond obtained as described above, and the center metal is A trivalent halogenated metal phthalocyanine pigment is produced by a dehydration reaction or a dehydrogenation reaction. The halogenated metal phthalocyanine pigment used in the present invention is preferably produced by using a metal phthalocyanine pigment having a light of 650 to 750 nm which is made of a 1-chloronaphthalene solution as a raw material. In the green pixel region of the color filter of the present invention, it is preferred that in the halogenated metal phthalocyanine pigment used in the present invention, the average particle diameter of the primary particles is 0. 01~0. A 10 micron halogenated metal phthalocyanine pigment. The halogenated metal phthalocyanine pigment having such an average particle diameter has a relatively weak agglutination of the pigment, and is easily dispersed in a photocurable composition which forms a color filter element region to be described later; On the 3 6 5 nm that is often used when the photohardenable composition of the pixel region is hardened, its -17-1300794 5, the invention description (16) the decrease in the light-shielding property (that is, the penetration becomes high) The photocuring composition also has a light hardening sensitivity which is less likely to cause film bending and patterning during development; For this reason, it is possible to easily obtain a color filter material having any of the high-resolution pixel regions having the sharpness and brightness required in recent years. Further, in the present invention, the average particle diameter of the primary particles is obtained by taking a picture of particles in the viewing zone by a transmission electron microscope JEM-2010 (Japan Electronics Co., Ltd.), and selecting 50 aggregates on the two-dimensional image. For the primary particles of the pigment, the average enthalpy of the long diameter (long diameter) of each of them is obtained. At this time, the above-mentioned pigment as a sample was dispersed in a solvent by ultrasonic waves, and photographed by a microscope. Alternatively, a scanning electron microscope can be used instead of a transmission electron microscope. The halogenated metal phthalocyanine pigment used in the present invention may be dry-pulverized by a pulverizer such as a honing machine, a ball mill, a vibration pulverizer or a vibratory ball mill as occasion demands, and then subjected to solvent salting-out grinding method. Or solvent boiling method for finishing treatment, and obtained 0. 01~0. 10 micron bismuth metal phthalocyanine pigment. The halogenated metal phthalocyanine pigment thus treated is excellent in dispersibility and coloring power before the trimming treatment, and is a relatively bright green pigment which emits a yellowish taste. The method of the correction treatment is not particularly limited, and a conventionally known method can be employed. For example, a large amount of the halogenated metal phthalocyanine pigment used in the present invention is further treated with a solvent which is heated and stirred in an organic solvent. The crystal growth can be easily controlled, and a large specific surface -18-1300794 is obtained, and the invention (17) is a product (that is, a relatively fine) pigment; according to these viewpoints, it is preferred to use a solvent salting-out honing method. To handle. The so-called solvent salting-out honing method means a halogenated metal phthalocyanine pigment which is pulverized directly or after the synthesis, and is subjected to mixing and grinding with an inorganic salt or an organic solvent. In this case, the kneading means is, for example, a kneading, a mixing method, or the like. In the halogenated metal phthalocyanine pigment used in the present invention, the material having the average particle diameter by the above-described trimming treatment has a weaker aggregation property of the primary particles than the conventional copper halide phthalocyanine pigment. It has a relatively easy to analyze nature. It was observed by electron microscopy that the pigment primary particles could not be observed in the conventional pigment. The primary particles of the halogenated metal phthalocyanine pigment used in the present invention have an aspect ratio of from 1 to 30, and the viscosity characteristics in the photocurable composition described later are increased, resulting in a photocurable composition. The fluidity is higher, and the coating property to the transparent substrate for the color filter material is also improved. Regarding the aspect ratio, first, as in the case of obtaining the average particle diameter of the primary particles, the image in the viewing zone is taken by a transmission electron microscope or a scanning electron microscope. Thereafter, 50 primary particles constituting the aggregate pigment on the two-dimensional image are selected, and the average 値 of the long diameter (long diameter) and the short diameter (short diameter) of each of the long directions is obtained, and the enthalpy is calculated. The green pixel region of the color filter material obtained from the halogenated metal phthalocyanine pigment used in the present invention is based on the results of visual evaluation, and is halogenated for use in -19-1300794, and the invention (18). The green pixel area produced by the copper phthalocyanine pigment is more excellent in yellowish green. The halogenated metal phthalocyanine pigment used in the present invention can be obtained by a combination of a Tmax system near the long wavelength side of 545 nm and a maximum transmittance which is larger than the conventional copper halide phthalocyanine. The green pixel area produced by the pigment is more excellent in yellowish green. That is, according to the halogenated metal phthalocyanine pigment used in the present invention, it is possible to more easily and inexpensively obtain a color filter material which cannot be achieved by a conventional copper halide phthalocyanine pigment, that is, has a Tmax of a green pixel region having a transmittance of 520 to 590 nm and having a transmittance of 70% or more on the aforementioned Tmax and a transmittance of the aforementioned spectral transmission spectrum at a wavelength of 650 to 700 nm of 20% or less Filter material. The color filter material of the present invention is a substance having the above-described characteristics, but according to the above description, it is preferable to have a Tmax of 520 to 590 nm and a transmittance of 85% to 99% on the aforementioned Tmax. And a color filter material having a transmittance of the aforementioned spectral transmission spectrum at a wavelength of 650 to 700 nm in a green pixel region of 〇 20%. In the preferred color filter material, the average particle diameter of the primary particles in the halogenated metal phthalocyanine pigment used in the present invention is 微米·〇!~〇"() micrometer, which can utilize the halogenated chloroaluminum phthalocyanine Pigment 'halogenated #-oxy-aluminum phthalocyanine dimer pigments and mixtures thereof, or are made using a zinc halide phthalocyanine pigment. Further, in the color filter material obtained by the present invention, in order to form a color filter material, green -20-1300794, and the invention (19) pixel region, in the halogenated metal phthalocyanine pigment used in the present invention, It is better to use yellow pigments with yellow flavor. That is to say, by such a usage, the transmittance of the spectral transmission spectrum at a wavelength of 400 to 500 nm in the green pixel region can be lowered, for example, the transmittance in the aforementioned wavelength region can be made 50%. the following. The yellow pigment which can be used here, for example, can be used C.  I. Yellow organic pigments such as Pigment Yellow 83, Pigment Yellow 110, Pigment Yellow 138, Pigment Yellow 139, Pigment Yellow 150, Pigment Yellow 180, Pigment Yellow 155, etc. The halogenated metal phthalocyanine pigment used in the present invention, and the yellow pigment The yellow pigment is used in an amount of, for example, 10 to 65 parts by mass per 100 parts by mass of the halogenated metal phthalocyanine pigment used in the present invention. Further, the green pixel region produced by the halogenated metal phthalocyanine pigment used in the present invention is a special means which does not require the use of a yellow pigment which is indispensable for coloring, or the halogenation used in the present invention. Among the metal phthalocyanine pigments, a yellow pigment may also be used, and a small amount is preferably used. In the case of producing a color filter material having a green pixel region of the same color as the conventional green color region of the color filter material, the same yellow pigment used in the halogenated metal phthalocyanine pigment can be reduced by 30% by mass. Above, the maximum can be reduced by about 50% by mass. In particular, in the case of a green pixel region of a color filter material obtained by bonding a halogenated metal phthalocyanine pigment having 9 or more bromine atoms to four benzene rings in each phthalocyanine molecule, it is possible to minimize It prevents its drop in transmittance in the entire visible region. -21 - 1300794 V. DESCRIPTION OF THE INVENTION (2〇) According to the halogenated metal phthalocyanine pigment used in the present invention, since the yellow pigment used therein is the minimum amount, and the pigment of two or more different colors is mixed In comparison with the conventional use of the coloring, it is possible to obtain a color filter material having a turbidity which causes re-aggregation, an excellent color purity, and a bright green pixel region. In such a pixel region as described above, it is extremely difficult to produce a portion intended to be a chromaticity and a hue, and to form a defect which is not the same. For example, as in the case of C.  I. In the case of the green pigment of the pigment green 3 6 , the mixed pigment of the yellow pigment described above is used as the liquid crystal display device in the case where the halogenated metal 'phthalocyanine pigment and the yellow pigment used in the present invention are used. The brightness of the liquid crystal display will be relatively small, and the amount of light penetration in the green area will also become large. This effect is achieved by subjecting the halogenated metal phthalocyanine pigment used in the present invention to the above-mentioned trimming treatment, and having an average particle diameter of the primary particles falling within the above range of four phenyl ring systems per one phthalocyanine molecule. In the case of a halogenated metal phthalocyanine pigment in which nine or more bromine atoms are bonded, it becomes more remarkable. The halogenated metal phthalocyanine pigment used in the present invention can be formed into a green pixel region of a color filter material by a conventionally known method. In the production of the color filter of the present invention, it is preferred to employ a pigment dispersion method. A representative example of such a method is a photolithography method in which a photocurable composition described later is applied to a surface of a transparent substrate for a color filter material on which a black substrate is provided, and after heating and drying (prebaking), Irradiation of ultraviolet light through a mask -22- 1300794 V. Description of the Invention (21) Exposure is performed to cure the photocurable compound corresponding to the position of the pixel region, and then the unexposed portion is visualized by the developing liquid. A method of removing a pixel region of a non-pixel region and fixing it on a transparent substrate. According to this method, the pixel region composed of the hard colored film of the photocurable composition can be formed on the transparent substrate. After modulating the photocurable composition described later on various colors including red, green, and blue, by repeating the above operations repeatedly, it is possible to manufacture various kinds of red, green, and blue at predetermined positions. Color filter material. According to the halogenated metal phthalocyanine pigment used in the present invention, a green pixel region can be formed. Further, a photocurable composition for forming a red pixel region and a blue pixel region can be prepared by using a conventionally known red pigment and blue pigment. It can be used as a pigment for forming a red pixel region, for example, C.  I. Pigment Red 177, Pigment Red 209, Pigment Red 254, etc.; can be used as a pigment for forming a blue pixel region, for example, C.  I. Pigment Blue 15, Pigment Blue 60, etc. Yellow and purple pigments can also be used in forming the red pixel region and the blue pixel region. Thereafter, all of the color filter materials may be subjected to heat treatment (post-baking) in order to thermally cure the photoreactive compound of the final reaction as occasion demands. A method of applying a photocurable composition to be described later on a transparent substrate such as glass, for example, a photocurable composition coated on a transparent substrate by spin coating, roll coating, or inkjet method, for example. Dry film of the coating film -23 - 1300794 5. The invention (22) is different depending on the type of each component, the mixing ratio, etc., but it is usually about 50 to 150 ° C for about 1 to 15 minutes. This heat treatment is generally referred to as "prebaking". Further, it is preferable to use ultraviolet light or visible light having a wavelength of 200 to 500 nm in the light hardening of the photocurable composition. Various light sources that emit light in this wavelength range can be used. The developing method is, for example, a liquid-filling method, a dipping method, a spraying method, or the like. After exposure and development of the photocurable composition, the transparent substrate forming the pixel region of the desired color can be washed with water and dried. The color filter material thus obtained can be heat-treated (post-baking) at a temperature of 100 to 280 ° C for a predetermined time by a heating device such as a hot plate or an oven to remove volatile components in the coating film while allowing light. The unreacted photocurable compound remaining in the hardened colored film of the curable composition is thermally cured to complete the color filter. The photocurable composition (referred to as a pigment dispersion photoresist) for forming a pixel region of a color filter material is a halogenated metal phthalocyanine pigment used in the present invention, a dispersant, a photocurable compound, An organic solvent is used as an essential component, and a thermoplastic resin is used as needed, and these are mixed and prepared. In the case where the color film forming the pixel region is required to have the toughness to be baked in the actual production of the color filter material, when the photocurable composition is prepared, not only the photocurable compound but also the photocurable compound may not be used. The plastic resin is used in the absence of the ground. In the case of using a thermoplastic resin, it is preferred to use a dissolved material as an organic solvent, and a method for producing the photocurable composition described above, generally in the present invention-24-1300794. The halogenated metal phthalocyanine pigment used in the above, and the essential components such as an organic solvent and a dispersing agent are uniformly mixed and stirred and dispersed, and firstly, a pigment dispersion liquid (referred to as a coloring paste) for forming a color filter material Then, a photocurable compound, a thermoplastic resin or a photopolymerization initiator which is optionally required, and the like are added to form a photocurable composition. As a dispersing agent, for example, it is a dispersed Baker 130 of Bukkanmin, a dispersed Baker 161, a dispersed Baker 162, a dispersed Baker 163, a dispersed Baker 170; and Afka Corporation. Ivka 46, Ivka 47, etc. Further, it may be used together with a conditioning agent, a coupling agent, or a cationic surfactant. The organic solvent may, for example, be an aromatic solvent such as toluene or xylene or methoxybenzene; or acetic acid such as ethyl acetate or propylene glycol monomethyl ether acetate or propylene glycol monoethyl ether acetate. Ester solvent; propionate solvent such as ethoxyethyl propionate; alcohol solvent such as methanol or ethanol; butyl ethyl ether ether, propylene glycol monomethyl ether, diethylene glycol diethyl ether, diethylene glycol methyl An ether solvent such as ether; a ketone solvent such as methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone; an aliphatic hydroxy solvent such as hexane; N,N-dimethylphosphide, r-butyrolactone, N-methyl a solvent of a nitrogen compound such as 2-bromodecanone, aniline or pyridine; a lactone solvent such as r-butyrolactone; an aminocarboxylic acid of a mixture of methyl carbamate and ethyl urethane of 48:52; Ester system, etc. It can be used as an organic glutinous agent. It is especially suitable for water-soluble substances such as propionate, alcohol, ether, ketone, nitridium or lactone. -25-1300794 , invention description (24). In the case of using a water-soluble organic solvent, it may be used together with water. It can be used as a thermoplastic resin for modulating a photocurable composition, and examples thereof include, for example, a polyurethane resin, an acrylic resin, a polyamide resin, a polyimide resin, and styrene. A maleic acid resin, a styrene anhydride maleic acid resin, or the like. It can be used as a photocurable compound, for example, 1,6-hexanediol diacrylate, ethylene glycol diacrylate, neopentyl glycol diacrylate, triethylene glycol diacrylate, a bifunctional monomer such as bis(acrylic acid oxyethoxy)biphenol A or 3-methylpentanediol diacrylate; such as trimethylolpropane triacrylate, pentaerythritol acrylate, tris(2-hydroethyl)isocyanate Polyfunctional monomers having a relatively small molecular weight such as dipentaerythritol hexaacrylate or dipentaerythritol pentaacrylate; and polyfunctional monomers having a relatively large molecular weight such as polyester acrylate, polyurethane acrylate, polyether acrylate, etc. body. It can be used as a photopolymerization initiator, for example, acetonitrile benzophenone, benzobenzophenone, benzomethylacetone, benzhydrin peroxide, 2-chlorothioxanthone, 1,3 -bis(4 |-hexanedibenzylidene)-2-propane, 1,3-bis(4'-hexanedibenzylidene)-2-propane 2'-sulfate, 4,4, Dihexylstilbene styrene-2,2'-disulfate, and the like. With the various materials as described above, it is possible to disperse the metal halide phthalocyanine pigment to be used in the present invention in an amount of 300 to 1000 parts by mass of the organic solvent and 0 to 1 part by mass per 100 parts by mass. The agent was uniformly stirred to obtain a dispersion of the above pigment. Then, in the pigment dispersion -26-1300794, the liquid of the invention (25), a total of 3 to 20 parts by mass of the thermoplastic resin and photohardening are added per 1 part by mass of the halogenated metal phthalocyanine pigment used in the present invention. The compound is 0 per 1 part by mass of the photocurable compound. 0 to 3 parts by mass of the photopolymerization initiator, and if necessary, an organic solvent is added, and the mixture is uniformly stirred and dispersed to obtain a photocurable composition for the green pixel region of the color filter. As the developer, a known organic solvent or an aqueous alkaline solution can be used. In particular, when the photocurable composition contains a thermoplastic resin or a photocurable compound, when at least one of them has an acid value and exhibits alkali solubility, it can be washed with an alkaline aqueous solution to form a picture. The effect of the prime area. Regarding the method of producing a color filter material by photolithography in the pigment dispersion method, in detail, in addition to the color filter material of the present invention, the crucible may be an electrolysis method, a transfer method, an electrolysis method, or a PVED (photopotential). A method such as electrolysis) is used to form a pixel region, and it is also possible to manufacture a color filter material. The color filter material of the present invention is a color filter material obtained by the above method, and in the green light pixel region, the light-transmitting spectrum of the entire visible light region shows the largest at 52 0 to 590 nm. Transmittance (Tm ax). Hereinafter, a method of measuring the Tmax in the spectral transmission spectrum of the present invention and the transmittance at Tmax will be described. In the backlight source of a conventional liquid crystal display device, a three-wavelength tube which emits green light having a main bright line of 545 nm is often used. The classification method of the three-wavelength tube is in accordance with the specification of the industrial specification UIS) Z8719, using a three-wavelength light-emitting form having a main line of the same as the main line of -27-1300794, and the invention (26) 545 nm. The camping light F10 light source is used as a measuring light source for evaluation. In the spectroscopic transmission spectrum of the present invention, it is determined according to the first spectrophotometer of Japanese Industrial Standards UIS) Z8722 (method of color measurement - reflection and transmission of object color); scanning with a predetermined wavelength region A resin film containing a pigment which is formed into a film having a predetermined thickness on a transparent substrate such as a glass substrate is patterned for each transmittance 各 according to each wavelength. In the present invention, the predetermined wavelength is visible light. For the film formation of the resin film containing a pigment, a photocurable compound or a thermoplastic resin can be used. When the transmittance measurement is carried out, it is carried out by any of the dried colored resin film or the cured colored resin film formed. Therefore, in short, a photocurable composition for forming a pixel region of the above-described color filter material can be used. When a colored resin film containing a component other than a pigment is formed on a photocurable composition, it is preferred that it does not have light absorbance at 520 to 590 nm or is extremely small, and the influence of the component on the measured absolute transmittance of the composition is Very small. Therefore, from the spectral transmission spectrum, Tmax and the transmittance at Tmax can be obtained. The transmittance of the color filter material can be corrected by correcting the spectral light transmission spectrum (base correction, etc.) by a film having the same film thickness only by the above-mentioned resin, thereby obtaining a more accurate and good result. [Examples] Next, the present invention will be specifically described by way of examples of the examples. However, it is not limited to this; in the following, the meaning of % means mass%; and the meaning of parts means mass parts. -28- 1300794 V. INSTRUCTION DESCRIPTION (27) [Production Example 1] Anthraquinone anhydride, urea, and aluminum chloride were used as raw materials to produce aluminum chloride phthalocyanine. The 1-chloronaphthalene solution has an absorption light of 6 50 to 75 nm. At 40 °C will be 3. 2 parts of sulfite chlorine, 3. 8 parts of anhydrous aluminum chloride, 0.  Mix 5 parts of sodium chloride and drop 2 .  7 parts of bromine is used as a halogenating agent. One part of the aluminum chloride phthalocyanine was added thereto, and the reaction was allowed to proceed at 90 ° C for 15 hours; thereafter, the reaction mixture was poured into water to precipitate a halogenated aluminum chloride phthalocyanine crude pigment. The aqueous slurry was filtered and washed in the order of 60 ° C soup, 1% sodium hydroxide water, and 60 ° C soup. Dry at 90 ° C to obtain refined 2 .  7 parts of halogenated aluminum chloride phthalocyanine crude pigment. 1 part of the halogenated aluminum chloride phthalocyanine crude pigment, 7 parts of the pulverized sodium chloride, 1 part of diethylene glycol, 0. 09 parts of xylene was placed in a double wrist type kneader and kneaded at l ° ° C for 6 hours. After the kneading, 100 parts of water at 80 ° C was taken out, stirred for 1 hour, and then filtered, washed, and dried to obtain an aluminum halide phthalocyanine 1 . The halogen content of the aluminum halide phthalocyanine 1 was analyzed by a flask combustion ion chromatography analysis, and the average composition thereof was AlClPcBhChH. Further, Pc represents a chemical structural formula in which yttrium and Y are removed in the above formula 1. The following are the same. Thus, the average composition can be presumed to mean that M = A1, Y = C1, and m are contained in Formula 1. =l, 乂 乂 "" 14 X series are bromine atoms, 1 X is a chlorine atom, and 1 X is a hydrogen atom of a halogenated aluminum chloride phthalocyanine pigment; and in the formula 1 contains M = A1 m=l, center metal of bismuth - 29- 1300794 V. Description of invention (28) M = A1, and 14 X systems in Χ17~Χ32 are bromine atoms, one X is a chlorine atom, and one X is a hydrogen atom Α is a halogenated-oxy-aluminum phthalocyanine dimer pigment of an oxygen atom. [Production Example 2] An oxidized phthalocyanine is produced by using phthalic anhydride, urea, and ruthenium pentoxide as a raw material. The solution has an absorption light of 650 to 750 nm. It will be 3 at 40 °C.  1 part of sulfite chlorine, 3 .  7 parts of anhydrous aluminum chloride, 0.  Mix 5 parts of sodium chloride and drop 2 .  6 parts of bromine is used as a halogenating agent. One part of the oxidized phthalocyanine was added thereto, and the reaction was allowed to proceed at 90 ° C for 15 hours; thereafter, the reaction mixture was poured into water to precipitate a halogenated oxidized phthalocyanine crude pigment. The aqueous slurry was filtered and washed in the order of 60 ° C soup, 1% sodium hydroxide water, acetone containing 7% toluene, and 60 ° C soup. Dry at 90 ° C to obtain refined 2 .  6 parts of halogenated phthalocyanine crude pigment. One part of the halogenated oxidized phthalocyanine crude pigment, 7 parts of the pulverized sodium chloride and one part of diethylene glycol were placed in a double wrist type kneader, and kneaded at 80 ° C for 8 hours. After kneading, it was extracted with 1 part of water at 80 ° C, stirred for 1 hour, and then filtered, washed, dried and pulverized to obtain a halogenated oxidized phthalocyanine 2 . The halogen content of the aluminum halide phthalocyanine 2 was analyzed by a flask combustion ion chromatography analysis, and the average composition thereof was V〇PcBr13Cl2H. (In the above formula 1, M = V, Y = 0, and m = 1, 13 X systems are bromine atoms, 2 X are chlorine atoms, and 1 X is a hydrogen atom). -30· 1300794 V. Inventive Note (29) [Production Example 3] Zinc phthalocyanine was produced by using sebaconitrile and zinc chloride as raw materials. The 1-chloronaphthalene solution has an absorption light of 650 to 75 nm. 3 · 1 part of sulfinium chloride at 40 ° C, 3 .  7 parts of anhydrous aluminum chloride, 0.  Mix 5 parts of sodium chloride and drop 2 .  6 parts of bromine is used as a halogenating agent. One part of the zinc phthalocyanine was added thereto, and the reaction was allowed to proceed at 90 ° C for 15 hours; thereafter, the reaction mixture was poured into water to precipitate a crude zinc halide phthalocyanine pigment. The aqueous slurry was filtered and washed in the order of 60 ° C soup, 1% sodium hydroxide water, acetone containing 7% toluene, and 60 ° C soup. It was dried at 90 ° C to obtain a purified 2·6 parts of a crude zinc halide phthalocyanine pigment. 1 part of the crude zinc halide phthalocyanine pigment, 7 parts of the pulverized sodium chloride, 1 part of diethylene glycol, 0. 09 parts of xylene was placed in a double wrist type kneader and kneaded at 100 ° C for 6 hours. After kneading, it was extracted with 100 parts of water at 80 ° C, stirred for 1 hour, and then filtered, washed, dried and pulverized to obtain a zinc halide phthalocyanine 3. The halogen content in the zinc halide phthalocyanine 3 was analyzed by a flask combustion ion chromatography analysis, and the average composition thereof was ZiiPcBryChH. (In the above formula 1, M = Zn, 14 X systems are bromine atoms, 1 X is a chlorine atom, and 1 X is a hydrogen atom). [Production Example 4] Sebacin and 4 titanium chloride were used as raw materials to produce titanium phthalocyanine. The 1-chloronaphthalene solution has an absorption light of 650 to 70 nm. -31 - 1300794 V. INSTRUCTIONS (3〇) 3 · 1 part of sulfite chlorine at 40 ° C, 3 .  7 parts of anhydrous aluminum chloride, 0. 5 parts of sodium chloride are mixed and dropped 2 .  6 parts of bromine is used as a halogenating agent. One part of the titanium phthalocyanine was added thereto, and the reaction was allowed to proceed for 15 hours at 90 t; thereafter, the reaction mixture was poured into water to precipitate a crude titanium halide phthalocyanine pigment. The aqueous slurry was filtered and washed in the order of 60 ° C soup, 1% sodium hydroxide water, acetone containing 7% toluene, and 60 ° C soup. Dry at 9 (TC) and obtain refined 2. 6 parts of titanium halide phthalocyanine crude pigment. 1 part of the titanium halide phthalocyanine crude pigment, 7 parts of the pulverized sodium chloride, 1 part of diethylene glycol, 0.  09 parts of xylene was placed in a double wrist f-kneader and kneaded at 100 ° C for 6 hours. After kneading, extracting with 100 parts of 8 (TC water, stirring for 1 hour, filtering, rinsing, drying and pulverizing to obtain titanium halide phthalocyanine 4. The zinc halide bismuth was analyzed by a flask combustion ion chromatography analysis. The halogen content in the cyanine 4 has an average composition of TiOPcBr1()Cl5H. (In the above formula 1, M = Ti, Y = 0, and m = 1, 10 X systems are bromine atoms, and 5 X are chlorine atoms. And one X is a hydrogen atom. [Production Example 5] Niobium nitrile and nickel chloride are used as raw materials to produce nickel phthalocyanine, and the 1-chloronaphthalene solution has absorption light of 650 to 750 nm. 3 · 1 part of sulfinium chloride, 3 · 7 parts of anhydrous aluminum chloride, 0 at 40 ° C.  Mix 5 parts of sodium chloride and drop 2 .  6 parts of bromine is used as a halogenating agent. One part of the nickel phthalocyanine was added thereto at -90-1300794 at 90 ° C, and the reaction (31) was reacted for 15 hours; then the reaction mixture was poured into water to precipitate a crude nickel halide phthalocyanine. pigment. The aqueous slurry was filtered and washed in the order of 60 ° C soup, 1% sodium hydroxide water, acetone containing 7% toluene, and 60 ° C soup. It was dried at 90 ° C to obtain a purified 2 · 6 parts of a crude nickel halide phthalocyanine pigment. 1 part of the crude nickel halide phthalocyanine pigment, 7 parts of the pulverized sodium chloride, 1 part of diethylene glycol, 0. 09 parts of xylene was placed in a double wrist type kneader and kneaded at 100 ° C for 6 hours. After kneading, it was extracted with 100 parts of water at 80 ° C, stirred for 1 hour, and then filtered, washed, dried and pulverized to obtain a nickel halide phthalocyanine 5. The halogen content in the nickel halide phthalocyanine 5 was analyzed by a flask combustion ion chromatography analysis, and the average composition thereof was NiPcBr13Cl2H. (In the above formula 1, M = Ni, m = 1, and X X to X16 are 13 bromine atoms, 2 X are chlorine atoms, and 1 X is a hydrogen atom). [Production Example 6] Sebacin was produced by using sebaconitrile and tin chloride as raw materials. The 1-chloronaphthalene solution has an absorption light of 650 to 750 nm. At 40 ° C will be 3. 1 part of sulfite chlorine, 3. 7 parts of anhydrous aluminum chloride, 0.  Mix 5 parts of sodium chloride and drop 2 .  6 parts of bromine is used as a halogenating agent. One part of the tin phthalocyanine was added thereto, and the reaction was allowed to proceed at 90 ° C for 15 hours; thereafter, the reaction mixture was poured into water to precipitate a crude titanium halide phthalocyanine pigment. The aqueous slurry was filtered to obtain a soup at 60 ° C, 1% sodium hydroxide water, acetone containing 7% toluene, 6 (-33-1300794 of TC soup, invention description (32).  Wash in order. It was dried at 90 ° C to obtain a purified 2 · 6 parts of a crude tin halide phthalocyanine pigment. 1 part of the crude tin halide phthalocyanine pigment, 7 parts of the pulverized sodium chloride, 1 part of diethylene glycol, 0. 09 parts of xylene was placed in a double wrist type kneader and kneaded at 100 ° C for 6 hours. After kneading, it was extracted with 100 parts of water at 80 ° C, stirred for 1 hour, and then filtered, washed, dried and pulverized to obtain a tin halide phthalocyanine 6. The halogen content in the tin halide phthalocyanine 6 was analyzed by a flask combustion ion chromatography analysis, and the average composition thereof was SnPcBr1QCl5H. (In the above formula 1, M = Sn, m = 1, 10 X-forms are bromine atoms, 5 X are chlorine atoms, and 1 X is a hydrogen atom). [Production Example 7] The conditions in Production Example 3 were changed to 0 in the primary particles.  The zinc halide phthalocyanine 7 was obtained in the same manner as in Production Example 3 except for the average particle diameter of 03 μm. [Comparative Production Example 1] Phthalic anhydride, urea, and copper chloride were used as raw materials to produce copper phthalocyanine. The 1-chloronaphthalene solution has an absorption light of 650 to 750 nm. The copper bromide phthalocyanine pigment 8 was obtained by the same operation as in Production Example 1 using copper phthalocyanine and the same halogenating agent as in Production Example 1. (In the above formula 1, M = Cu, m = 0, and 15 X systems in Xi to X16 are bromine atoms, and one X is a hydrogen atom). [Examples 1 to 6] • 34-1300794 V. Description of the Invention (33) The green pigments of the various pigments 1, 2, 3, 4, 5 and 6 obtained in the above production examples were produced by photolithography. The green pixel areas 1, 2, 3, 4, 5 and 6 of the color filter. The method for producing the green color region of the color filter material is to use 14 parts of each pigment, 3 parts of C·I·Pigment Yellow 150 (yellow organic pigment for coloring), 2. 5 parts of N,^-dimethylammonium phosphate (organic solvent), 17.0 parts of dispersion rubber 161 (dispersant made by Cookmi), 63. 5 parts of Eugenate EEP (organic solvent made by Eucalyptus) is added to 0. A 5 mm 0 safety bead was dispersed by a paint conditioner (manufactured by Toyo Seiki Co., Ltd.) for 1 hour to prepare a pigment dispersion. Will be 75. 00 parts of the pigment dispersion, and 5. 50 copies of Alonicus M7100 (polyester acrylate made by East Asia Synthetic Chemical Industry Co., Ltd., equivalent to photocurable compound), 5. 00 parts of KAYARAD DPHA (diuretic tetraol ester hexaacrylate manufactured by Nippon Pharmaceutical Co., Ltd., equivalent to photocurable compound), 1 .  00 parts of KAYACURE BP-100 (benzophenone manufactured by Nippon Pharmaceutical Co., Ltd., equivalent to a photoinitiator), and 13.  Five parts of the superior chelate EEP were stirred with a dispersing mixer to obtain a photocurable compound for forming a green pixel region of the color filter. The composition was applied to a glass having a thickness of 1 mm in accordance with a dry film thickness of 1 μm. Next, the ultraviolet ray was irradiated through a photomask to expose it, and the unexposed portion was washed with an organic solvent to form a green pixel region for the color filter. The results of the respective pigments were measured by a transmission electron microscope: TEM-2010 (manufactured by Nippon Denshi Co., Ltd.) to obtain the average particle diameter of the primary particles of the respective pigments of -35-1300794. The chromaticity and brightness of the green pixel regions 1, 2, 3, 4, 5 and 6 of the color filter materials produced by the pigments 1 to 6 were visually evaluated. Further, the first type of spectrophotometer (spectrophotometer specified in the Industrial Standard (JIS) Z8722 is used to measure the wavelength (Tmax) of the maximum transmittance in the spectral transmission spectrum of the entire visible light region, at the aforementioned Tmax The penetration rate, the maximum transmittance in the wavelength range of 650 to 700 nm, and the measurement of the spectral transmission spectrum in the green pixel regions 1 and 3 of the color filter, and the equivalent of 50% of the maximum transmittance The distance between the two intersections formed by the interpolated line within the penetration rate (the distance in the figure is expressed in nanometers). The results are shown in Table 1. In Example 1 and Example 3 The color transmission spectrum of the green pixel region obtained by the color filter material is shown in Fig. 1 and Fig. 2, respectively, except that C having the average particle diameter of the same primary particle is used. Pigment Red 254 (diketopyrrole red organic pigment) and C.  I. Pigment Blue 15.  . In place of the pigment 1, 64 (the ε-type copper phthalocyanine-based blue organic pigment) is similarly formed into a green pixel region to modulate the respective creep compositions of red and blue, and to form a red pixel region, respectively. And the blue pixel area; and the color material set with various RGB pixel regions is obtained. [Comparative Example 1] In the same manner as in Example 1 except that the copper bromide pigment 8 was used instead of the halogenated phthalocyanine pigment 1, the green pixel region for the color filter material was obtained. 8. -36- 1300794 V. Inventive Note (35) In the same manner as in the first embodiment, the average particle diameter of the primary particles of the pigment 8 and the green pixel region 8 for the color filter material produced by the pigment 8 were visually evaluated. Chromaticity and brightness. Also, use a spectrophotometer. To determine Τιώax, the penetration rate at the aforementioned Tmax, and the maximum transmittance in the wavelength range of 650 to 700 nm. Further, the distance between the two intersections formed by the interpolated lines corresponding to the transmittance at 50% of the maximum transmittance (half width) was measured. This result is shown in Table 1. The broad axis is the horizontal axis and the transmittance is the vertical axis, and the color filter material is shown in Fig. 3 by the spectral transmission spectrum of the green pixel region. Table 1 Example 1 Example 2 Example 3 Green pixel area for color filter material 1 2 3 Pigment composition AlClPcBrnCliH V(0)PcBr13Cl2H ZnPcBr14Cl ιΗ Primary particle: Average particle diameter of F. 03 micron 0. 03 micron 0. 06 micron macroscopic chromaticity 〇〇〇 evaluation brightness Δ Δ Δ Tmax 529 nm 535 nm 521 nanometer measured Tmax penetration rate 92% 78% 89% fixed half width 136 nm 99 nm 値 650 ~ The maximum penetration rate of 700 nm is 0. 3% 4. 4% 1. 8% -37- 1300794 V. INSTRUCTIONS (36) Table 1 (Box 1) Example 4 Example 5 Example 6 Green pixel area for color filter material 4 5 6 Pigment composition Ti(O)PcBr10Cl5H NiPcBr13Cl2H SnPcBr10Cl5H Primary particle The average particle size is 0. 01 micron 0. 01 micron 0. 01 micron @ 视色〇〇〇 〇〇〇 売 Δ Δ Δ Tmax 528 nm 526 nm 530 nm measured penetration rate in Tmax 83% 75% 80% fixed half width 値 650~700 nm The maximum penetration rate of 6. 9% 1. 0% 1. 6% Table 1 (continued) Comparative Example 1 Green pixel area for color filter material 8 Pigment composition C u P c B r ! 5 平均 Average particle size of primary particles 0. 04 micron giant color chromaticity X evaluation brightness Δ Tmax 51 3 nanometers measured penetration rate in Tmax 85% fixed half width 1 13 nm 値 650~700 nm maximum penetration rate 5 .  0% -38- 1300794 V. Description of Invention (π) In Table 1, the contents of the symbols are as follows. Chromaticity: 〇···With green color equivalent to yellow scent · · · Green brightness with yellow scent: 〇 · · · Very bright X · · · A little dark due to Table 1 can be understood: use Al, V, Zn, Ti, Ni, Sn are the central metal halide metal phthalocyanine pigments 1, 2, 3, 4, 5 and 6 for the color material green pixels 1, 2, 3, 4, 5 and 6' The result of the evaluation is to compare the bright substances with yellow flavor. On the other hand, it can be understood that the green pixel region 8 of the color filter material using the halogenated metal phthalocyanine pigment 8 which is a copper-centered metal is visually evaluated as yellow with insufficient yellowness, and the brightness is slightly dark. substance. [Example 7] In Example 3, the same procedure as in Example 3 was carried out except that the above-mentioned zinc halide phthalocyanine pigment 7 was used instead of the zinc halide phthalocyanine pigment 3, and the green pixel region for forming a color material was formed. 7' and carry out the same measurement as described above. The results of this Example 7 are shown in Table 2. -39- 1300794 V. INSTRUCTIONS (38) TABLE 2 Comparative Example 7 Green gramin area for color filter material 7 Pigment composition ____ ZnPcBr14Cl # Average particle size of primary particles 0. 03 micron chromaticity 〇 evaluation brightness 〇 Tmax 529 nm measured penetration in Tmax _ 92% fixed half width 105 nm 値 maximum penetration in 650~700 nm 7. 3% From the comparison between Example 3 and Example 7, it is understood that the green pixel region obtained from the zinc halide phthalocyanine pigment 7 having a smaller average particle diameter of the primary particles is compared with the zinc halide phthalocyanine pigment 3, and the visual result is obtained. Its brightness is even better, while Tmax is closer to 545 nm, and the penetration at Tmax is also higher. Using the pigments 7 and 8, the test pieces were produced in accordance with JIS k5101-1991 (Japanese Industrial Standard "Pigment Test Method"), and each of the L-shaped beamsplitters was obtained by the data color company to obtain the color of each of them. Force scale. When the ruthenium was used as the ruthenium phthalocyanine pigment 8 of Comparative Example 1, the L 値 of the zinc halide phthalocyanine pigment 7 was equivalent to 99, and the coloring power was about 10% higher. -40- 1300794 V. Inventive Note (39) Moreover, in the green pixel region obtained in each of the examples, when visually observed, no chroma or hue portion can be observed in any of the pixel regions. presence. [Industrial Applicability] The present invention provides a color filter material comprising a halogenated metal phthalocyanine pigment having 8 to 16 halogen atoms in each phthalocyanine molecule bonded to a phthalene ring of a phthalocyanine molecule; The green pixel region with a maximum transmittance of 520 to 590 nm in the spectral light transmission spectrum of the whole region of visible light; compared with the green pixel region using copper phthalocyanine, it is more capable of achieving The bright green color close to the yellow flavor is particularly effective. Moreover, in the chromaticity or hues of the same color, it is also possible to achieve an exceptionally significant effect that does not cause the formation of chromaticity or hue. -41 -

Claims (1)

p year γ month / day repair (P original six, patent application scope 9 1 1 0 3 9 1 2 "filter material" patent case (amendment of April 1, 1993) six application patent scope: 1. The color filter material is characterized in that the color filter material is a plurality of pixel regions having red, green, and blue colors on a transparent substrate, and the green pixel region (1) contains a halogenated metal represented by the following formula 1. Phthalocyanine pigment; formula 1 Here, X1~ represents a hydrogen atom, a chlorine atom, a bromine atom, or an iodine atom, and the four X atom atoms bonded to one benzene ring are the same 'may be different; the bond is on four benzene rings χ χ 6 6 contains δ ~ 16 hydrogen atoms, chlorine atoms, bromine atoms, or iodine atoms; μ system represents the central metal, is selected from Si, Sc, Τι, Mg, Fe, 1300794 6. In the group of Co, Ni, Zn, Ge, Y, Zr, Nb, Sn and Pb, the Y system bonded to the central metal M is from fluorine, chlorine, bromine or iodine. One of a group consisting of a halogen atom, an oxygen atom, a hydroxyl group (-0Η), and a sulfonic acid group (-S03H), wherein m represents the number of Y bonded to the central metal ruthenium, An integer of 0 to 2; when the central metal is trivalent, the central metal is bonded to any one of the above halogen atoms, hydroxyl groups or sulfate groups; when the central metal is tetravalent Next, the central metal system may be bonded to any one of the above halogen atoms, hydroxyl groups or sulfonic acid groups by the same or different oxygen atoms; and in the spectroscopic light transmission spectrum of the entire visible light region 520~ The maximum penetration rate is shown at 590 nm. 2. For the color filter material of claim 1, wherein the central metal Μ is Ζη; and the number m of Υ is 0. 3. The color filter material is characterized in that: the furnace and the color material are on a transparent substrate having various pixel regions of red, green and blue, wherein the green pixel region is (1) containing the following Halogenated metal phthalocyanine pigment represented by Formula 1: Formula 1 : 1300794 Here, χ^χ16 represents a hydrogen atom, a chlorine atom, a bromine atom, or an iodine atom, and the four X atom atoms bonded to one benzene ring are the same or different; the bond is in four benzene rings. There are 8 to 16 hydrogen atoms, chlorine atoms, bromine atoms, or iodine: atoms; the lanthanide represents a central metal, which is a trivalent metal selected from the group consisting of Sc and lanthanum, and m represents 1; The Y series represents the following atomic groups: 1300794 VI. Patent Application Scope Here, Xl 7~X32 represents a hydrogen atom, a chlorine atom, a bromine atom, or an iodine atom, and the four X atom atoms bonded to one benzene ring are the same or different; The X7 to X32 bonded to the four benzene rings has 8 to 16 hydrogen atoms, chlorine atoms, bromine atoms, or iodine atoms; the lanthanum represents a central metal selected from the group consisting of S c and Υ a trivalent metal; ruthenium is a divalent atomic group selected from the group consisting of an oxygen atom, a sulfur atom, a sulfinyl group (_s〇-), and a sulfonyl group (-S02-); The enthalpy with the atomic group Y represents bonding via a divalent atomic group; and (2) the maximum transmittance is shown at 520 to 590 nm in the spectral light transmission spectrum of the entire visible light region. The color filter material according to any one of claims 1 to 3, wherein the primary particle diameter of the halogenated phthalocyanine metal pigment is 〇 1 to 0.1 μm. The color filter material according to any one of claims 1 to 3, wherein among the 8 to 16 halogen atoms bonded to the benzene ring of the phthalocyanine molecule, 9 or more are bromine atoms. 6. The color filter according to any one of claims 1 to 3, wherein the green pixel region has a transmittance of 70% or more in a wavelength exhibiting a maximum transmittance. 7. The color filter material according to any one of claims 1 to 3, wherein the green pixel region has a transmittance of 85% or more in a wavelength exhibiting a maximum transmittance. -4 -