TW201829382A - Phthalimide, pigment dispersant using derivative of the same, and colored composition - Google Patents

Abstract

The object of the present invention is to provide a pigment dispersant which can inhibit an increase in viscosity after preparing a pigment dispersant regardless of the type of a phthalocyanine pigment, and also, can inhibit a decrease in film contrast after preparing a colored composition comprising the same; and a colored composition comprising the same. The present invention provides a pigment dispersant which comprises at least one member selected from the group consisting of phthalimide represented by formula (1) and a derivative thereof; a phthalocyanine pigment; a dispersant; and a solvent. In the formula (1): R1-R4 are a hydrogen atom or a halogen atom; and Q is (i) a hydrogen atom, (ii) an alkyl group having 1-5 carbon atoms which may have a substituent X that is bound to a terminal carbon atom, or (iii) an aryl group which may have a substituent Y that is bound to a carbon atom of an aromatic ring, wherein the substituent X is an acetyl group, a carboxyl group, a phosphate group, or a sulfonic group, and the substituent Y is a methyl group, an acetyl group, a carboxylic group, a phosphate group, or a sulfonic group.

Description

Pigment dispersion and coloring composition using phthalimide and its derivatives

[0001] The present invention relates to a pigment dispersion and a coloring composition using phthalimide and its derivatives, and in particular, to a pigment dispersion used in a color filter provided on a flat panel of a display device, for example. And colored composition containing it.

[0002] A color filter has been widely used as a constituent member of a liquid crystal display (LCD) and the like. LCDs are widely used in display devices such as monitors, televisions, notebook personal computers, tablet personal computers, and smart phones. These display devices are required to be high-quality. On the other hand, in recent years, based on the viewpoint of global environmental protection and the like, demands for reducing power consumption have also increased. Therefore, the color filters constituting them are required to have high brightness, high contrast, and the like. [0003] Color filters are widely used as coloring photosensitive compositions in which red, green, and blue dyes or pigments are dissolved or dispersed in a photosensitive resin as a coating liquid. It is produced by forming a coating film in a shadow step. As a method for realizing the improvement of the image quality of the color filter as described above, it is conceivable to improve the color purity by increasing the concentration of a dye or a pigment in the coloring photosensitive composition. However, in this case, since the light transmittance due to the backlight of the LCD is reduced, power consumption is increased. In addition, in order to achieve high contrast, it is conceivable to disperse large-sized particles of the pigment and to disperse small-sized particles of the pigment below the wavelength of light in the colored photosensitive composition. However, the pigment tends to aggregate more easily as the particle size is smaller, and it is difficult to uniformly disperse the pigment in the colored photosensitive composition. Therefore, it is required to develop a pigment that can realize a high-brightness and high-contrast color filter capable of expressing the same brightness with less light than in the past without increasing the concentration of the pigment or the like. Therefore, a color filter formed using these pigments has been proposed (Patent Document 1). [0004] For example, by using a pigment as disclosed in Patent Document 1, a high degree of brightness and high contrast of a color filter can be expected. However, in general, it is not easy to uniformly disperse a pigment in a colored photosensitive composition. For example, a method using a dispersant or a pigment derivative as a component constituting the colored photosensitive composition or using a surface-treated pigment is generally adopted. Since the characteristics of these components are related to the dispersibility of pigments, it is considered that by selecting them, the effects on the performance of color filters are seen accordingly. [0005] However, as described above, the color filter is widely produced by forming a coating film by a photolithography step. Therefore, a photoresist composition having good characteristics as a photoresist has been proposed (Patent Document 2). Patent Document 2 describes that a basic compound is preferably contained for the purpose of suppressing the diffusion rate of the acid in the photoresist film, improving the resolution, and suppressing the change in sensitivity after exposure. In addition, it is described that a fluorene imine derivative such as phthalimide can be used as a basic compound. [0006] In addition, fluorene imine derivatives are sometimes used for inkjet inks or recording inks (Patent Documents 3 and 4). Patent Document 3 describes the use of a hydroxylamine derivative in order to provide long standby time and long-term ejection stability when used in a thermal inkjet printer. As a specific example of the hydroxylamine derivative, o-benzene is described. Dimethyimine. Patent Document 4 describes that a recording ink containing water and polyvinylpyrrolidone contains a substance having a pyrrolidine ring in order to prevent hydration of water and polyvinylpyrrolidone, as a specific example. There is phthalimide. [Prior Art Document] [Patent Document] [0007] [Patent Document 1] Japanese Patent Laid-Open No. 2016-38584 [Patent Document 2] Japanese Patent Laid-Open No. 2006-251296 [Patent Document 3] Japanese Patent Laid-Open No. 10-204359 Gazette [Patent Document 4] Japanese Patent Laid-Open No. 7-331146

[Problems to be Solved by the Invention] [0008] The present inventors have found that a phthalocyanine-based green pigment CI Pigment Green 59 manufactured by DIC Corporation using the pigment disclosed in Patent Document 1 prepares a pigment dispersion containing a dispersant and a solvent, and The coloring composition using the same, after forming a coating film using the coloring composition, the contrast of the coating film of a person who is left for a certain period of time after the preparation is lower than that of the latter. In addition, it was found that instead of CI Pigment Green 59, other phthalocyanine-based pigments were treated in the same manner. After the pigment dispersion was allowed to stand for a certain period of time, its viscosity increased, which caused a problem that it was not easy to handle when preparing the coloring composition. [0009] Therefore, an object of the present invention is to provide a pigment dispersion that can suppress the increase in viscosity after preparing a pigment dispersion and can suppress the decrease in the contrast of a coating film after preparing a coloring composition containing the pigment dispersion regardless of the type of phthalocyanine pigment. Body and colored composition containing it. [Means to Solve the Problem] [0010] After the present inventor's active review, he found that by using phthalimide and a specific phthalimide derivative, the above problems can be solved, thus completing the present invention. invention. The gist of the present invention is as follows. [0011] A first object of the present invention relates to a pigment dispersion containing at least one selected from phthalimide and its derivative represented by the following formula (1), a phthalocyanine pigment, and a dispersion Agents and solvents. (In the formula (1), R ¹ to R ⁴ are a hydrogen atom or a halogen atom, Q is (i) a hydrogen atom, (ii) an alkane having 1 to 5 carbon atoms which may have a substituent X bonded to a terminal carbon atom. Or (iii) an aryl group which may have a substituent Y bonded to a carbon atom of the aromatic ring, the substituent X is an ethyl group, a carboxyl group, a phosphate group, or a sulfonic group, and the substituent Y is a methyl group, an ethyl group, Carboxyl, phosphate, or sulfonate). [0012] In a preferred embodiment of the present invention, the phthalocyanine pigment is a metal phthalocyanine pigment. It is more preferably a zinc phthalocyanine pigment or a copper phthalocyanine pigment. Furthermore, a further preferred embodiment of the zinc phthalocyanine pigment is a zinc halide phthalocyanine pigment having an average number of hydrogen atoms in a molecule of 2 or more, and particularly preferably an average number of hydrogen atoms in a molecule of 2 The above zinc halide phthalocyanine pigment is preferably a zinc bromide zinc phthalocyanine pigment. [0013] In a preferred embodiment of the present invention, Q in the aforementioned formula (1) is (ii) an alkyl group having 2 carbon atoms having a substituent X bonded to a terminal carbon atom, and the substituent X is a carboxyl group or Phosphate group. [0014] A second object of the present invention relates to a coloring composition including the pigment dispersion and a coating film-forming component. In a preferred embodiment of the present invention, a photopolymerizable component is included as the coating film forming component. [Inventive Effect] [0015] According to the present invention, regardless of the type of phthalocyanine pigment, it is possible to suppress an increase in viscosity after the pigment dispersion is prepared, and to suppress a decrease in the contrast of the coating film after the colored composition containing the pigment dispersion is prepared.

[0016] Hereinafter, embodiments of the present invention will be described. [0017] An embodiment of the pigment dispersion of the present invention contains at least one selected from phthalimide and its derivative represented by the following formula (1), a phthalocyanine pigment, a dispersant, and a solvent. (In formula (1), R ¹ ~ R ⁴ Is a hydrogen atom or a halogen atom, and Q is (i) a hydrogen atom, (ii) an alkyl group having 1 to 5 carbon atoms, which may have a substituent X bonded to a terminal carbon atom, or (iii) may be bonded to an aromatic ring The aryl group of the substituent Y of the carbon atom, the substituent X is an ethyl group, a carboxyl group, a phosphate group, or a sulfonic group, and the substituent Y is a methyl group, an ethyl group, a carboxyl group, a phosphate group, or a sulfonic group). [0018] By using a phthalocyanine pigment in combination with at least one selected from phthalimide and a specific phthalimide derivative represented by formula (1), the mechanism of action is not yet known It is clear, but regardless of the type of phthalocyanine pigment, it is possible to suppress an increase in viscosity after the pigment dispersion is prepared, and it is possible to suppress a decrease in the contrast of the coating film after the colored composition containing the pigment dispersion is prepared. [0019] The (ii) alkyl group having 1 to 5 carbon atoms which may have a substituent X bonded to a terminal carbon atom is not particularly limited as long as it is an alkyl group having 1 to 5 carbon atoms or has a bond to a terminal carbon. The atomic substituent X may be an alkyl group having 1 to 5 carbon atoms. That is, as long as it is methyl (-CH ₃ ), Ethyl (-C ₂ H ₅ ), Propyl (-C ₃ H ₇ ), Butyl (-C ₄ H ₉ ), Amyl (-C ₅ H ₁₁ ), -CH ₂ -X, -C ₂ H ₄ -X,-(C ₂ H ₄ ) CH ₂ -X,-(C ₃ H ₆ ) CH ₂ -X,-(C ₄ H ₈ ) CH ₂ -X is fine. Butyl and pentyl may be linear or branched. Among them, from the viewpoint of more exerting the effect of suppressing the increase in viscosity of the pigment dispersion and the effect of decreasing the contrast of the coating film, an alkyl group having 1 to 4 carbon atoms is preferred, an alkyl group having 1 to 3 carbon atoms is more preferred, and even better It is an alkyl group having 1 to 2 carbon atoms, and particularly preferably an alkyl group having 2 carbon atoms. [0020] In the case of (ii), the substituent X is preferably an acetyl group, a carboxyl group, a phosphate group, or a sulfonic acid group. Among them, from the viewpoint of further exerting the effect of suppressing the increase in viscosity of the pigment dispersion and the effect of suppressing the decrease in the contrast of the coating film, the acetyl group, the carboxyl group, and the phosphate group are more preferable, and the carboxyl group and the phosphate group are more preferable. [0021] The aryl group (iii) which may have a substituent Y bonded to a carbon atom of an aromatic ring is not particularly limited, but is preferably an aryl group having 6 to 14 carbon atoms, more preferably 6 to 10 carbon atoms. Of aryl. Specific examples of the ring constituting the aryl group include a benzene ring, a naphthalene ring, an anthracene ring, a phenanthrene ring, a fluorene ring, a triphenylene ring, a fluorene ring, a tetracene ring, and a biphenyl ring (two phenyl groups may be arbitrarily connected) Morphological connection), bitriphenyl (3 phenyl groups can be arbitrarily connected), and the like. In the case of (iii), the substituent Y is preferably a methyl group, an ethanoyl group, a carboxyl group, a phosphate group, or a sulfonic acid group. Moreover, as a substituent, it is preferable not to have a functional group other than these. The position and number of the substituent Y are not particularly limited. [0022] In an embodiment, at least one selected from phthalimide and its derivative represented by the above formula (1) can be used. Among them, from the viewpoint of more exerting the effect of suppressing the increase in viscosity of the pigment dispersion and the effect of reducing the contrast of the coating film, in formula (1), Q is preferably (i) a hydrogen atom, or (ii) may have a bond to a terminal carbon The alkyl group having 1 to 4 carbon atoms of the substituent X is more preferably (ii) the alkyl group having 1 to 4 carbon atoms having the substituent X bonded to the terminal carbon atom, and the substituent X is a carboxyl group or a phosphoric acid And more preferably (ii) an alkyl group having 1 to 2 carbon atoms having a substituent X bonded to a terminal carbon atom, and the substituent X is a carboxyl group or a phosphate group, and preferably (ii) has a bond to The alkyl group having 2 carbon atoms of the substituent X at the terminal carbon atom is a carboxyl group or a phosphate group. [0023] A specific example of (ii) an alkyl group having 1 to 2 carbon atoms having a substituent X bonded to a terminal carbon atom, and the substituent X is a carboxyl group or a phosphate group is -CH ₂ COOH, -C ₂ H ₄ COOH, -CH ₂ -OPO (OH) ₂ , -C ₂ H ₄ -OPO (OH) ₂ . [0024] In the formula (1), R ¹ ~ R ⁴ As long as it is a hydrogen atom or a halogen atom, according to the review by the present inventor, there is a tendency that different combinations are preferred depending on the type of Q. For example, Q is -CH ₂ COOH, R ¹ ~ R ⁴ When it is a hydrogen atom, it helps to suppress the decrease in the contrast of the coating film of the coloring composition. Q is -C. ₂ H ₄ COOH, R ¹ ~ R ⁴ When it is a halogen atom, it contributes to the tendency of improving the said contrast. And R ¹ ~ R ⁴ When any of them is a halogen atom, it is substituted by the number of halogen atoms, R ¹ ~ R ⁴ Which one is a halogen atom is not particularly limited. Although it does not specifically limit as a halogen atom, From a viewpoint of suppressing the viscosity increase of a pigment dispersion, and suppressing the fall of the contrast of the coating film of a colored composition, a chlorine atom and a bromine atom are preferable. Halogen atom at R ¹ ~ R ⁴ They can all be the same or different. [0025] The content of the at least one selected from the phthalimide and its derivative represented by the formula (1) in the pigment dispersion is not particularly limited, but is relative to 100 parts by weight of the phthalocyanine pigment. It is preferably 2 to 10 parts by weight, and more preferably 3 to 6 parts by weight. [0026] Commercially available phthalimidine can be used. The phthalimide derivatives can be produced by conventional methods. It can also be used commercially. [0027] The phthalocyanine pigment is not particularly limited, but is preferably a metal phthalocyanine pigment because it is easy to enjoy the effects of suppressing the increase in viscosity of the pigment dispersion and the effect of reducing the contrast of the colored composition. Metal phthalocyanine pigments are composed of a complex of metal ions at the center of the phthalocyanine and derivatives thereof. The metal that can be a coordinated metal ion is only required to be ordinary in the technical field. For example, as a stable coordination bond, examples include copper, zinc, vanadium, chromium, manganese, iron, cobalt, nickel, and platinum. Wait. Among them, zinc and copper are preferred. That is, as a metal phthalocyanine pigment, a zinc phthalocyanine pigment and a copper phthalocyanine pigment are more preferable. [0028] The phthalocyanine pigment may be a halogen derivative in which at least one of the hydrogen atoms of the phthalocyanine bonded to the benzene ring is substituted with a halogen atom. The halogen atom is preferably a chlorine atom or a bromine atom. The halogen atom may be one kind, or two or more kinds. It can be appropriately selected according to the desired color. [0029] The zinc phthalocyanine pigment is preferably a halogenated zinc phthalocyanine pigment. As these zinc halide phthalocyanine pigments, those described in Patent Document 1, for example, can be used. The summary of the contents is as follows. [0030] Zinc phthalocyanine has 16 hydrogen atoms in one molecule, and those hydrogen atoms replaced by halogen atoms such as chlorine atom or bromine atom are zinc halide phthalocyanine pigments. Among these, a zinc bromide zinc phthalocyanine pigment is preferred. [0031] The chlorine atom content ratio in the zinc halide phthalocyanine pigment is preferably 3.5% by mass or more and 30% by mass or less. The lower limit is more preferably 3.8% by mass or more, still more preferably 4.0% by mass or more, and even more preferably 4.3% by mass or more. The upper limit is more preferably 20% by mass or less, still more preferably 10% by mass or less, and particularly preferably 6% by mass or less. The content of halogen atoms contained in the zinc halide phthalocyanine pigment can be determined by dissolving the pigment in ethyl benzoate and burning it in a combustion device, and absorbing the combustion gas in a hydrogen peroxide absorbing liquid. Combustion gas-ion chromatography determination of ions. [0032] The number of chlorine atoms contained in 16 substituents in one molecule of the zinc halide phthalocyanine pigment is not particularly limited, but it is preferably 1 or more and 14 or less. The lower limit is more preferably two or more, and still more preferably three or more. The upper limit is more preferably 10 or less, still more preferably 6 or less, and particularly preferably 4 or less. The number of chlorine atoms contained in one molecule of pigment is an average value calculated from the average value of the average molecular weight measured by the LDI-MS method described later and the chlorine atom content ratio measured by the aforementioned combustion gas-ion chromatography method. . [0033] When the zinc halide phthalocyanine pigment is a zinc bromide zinc phthalocyanine pigment, the molar ratio of the chlorine atom in one molecule of the pigment to the molar ratio of the bromine atom is not particularly limited, but is preferably 0.1. Above 7 below. The lower limit is more preferably 0.12 or more, still more preferably 0.15 or more, and still more preferably 0.2 or more. The upper limit is more preferably 3 or less, still more preferably 1 or less, still more preferably 0.5 or less, and particularly preferably 0.3 or less. [0034] The content ratio of bromine atoms in the zinc halide phthalocyanine pigment is preferably 30% by mass or more and 80% by mass or less. The lower limit is more preferably 40% by mass or more, still more preferably 45% by mass or more, and particularly preferably 50% by mass or more. The upper limit is more preferably 70% by mass or less, still more preferably 60% by mass or less, and particularly preferably 55% by mass or less. [0035] The number of bromine atoms contained in 16 substituents in one molecule of the zinc halide phthalocyanine pigment is not particularly limited, but it is preferably 5 or more and 15 or less. The lower limit is more preferably 8 or more. The upper limit is more preferably 13 or less, still more preferably 12 or less, even more preferably 11 or less, and particularly preferably 10 or less. The number of bromine atoms contained in one molecule of the pigment is an average value calculated in the same manner as in the case of the above-mentioned chlorine atom. [0036] The average number of hydrogen atoms contained in one molecule of the zinc halide phthalocyanine pigment is not particularly limited, but is preferably 2 or more and 14 or less. The lower limit is more preferably 3 or more, still more preferably 4 or more, particularly preferably 5 or more, and most preferably 6 or more. The upper limit is more preferably 12 or less, still more preferably 10 or less, particularly preferably 8 or less, and most preferably 7 or less. The average number of hydrogen atoms in one molecule of the zinc halide phthalocyanine pigment is the average value of the average molecular weight measured by the LDI-MS method described later and the bromine atom and chlorine atom content measured by the aforementioned combustion gas-ion chromatography method. The average value calculated by the ratio. Details can be obtained in the following order. [0037] First, the average molecular weight was measured by a laser desorption / ionization (LDI) -mass spectrometry (MS) method. The measurement of the average molecular weight was performed 4 times, and the average value of the measurement results of 4 times was taken (hereinafter referred to as "the average value of the average molecular weight"). Next, the chlorine atom content ratio [mass%] and the bromine atom content ratio [mass%] in the pigment were measured by combustion gas-ion chromatography. The average number of chlorine atoms and the average number of bromine atoms in one molecule of the pigment were calculated from the average value of the average molecular weight, the content ratio of chlorine atoms and the content ratio of bromine atoms. Since there are 16 positions occupied by the chlorine atom, bromine atom, and hydrogen atom in the zinc phthalocyanine, the remaining positions not occupied by the chlorine atom and the bromine atom are calculated to obtain the average number of hydrogen atoms. [0038] These zinc halide phthalocyanine pigments can be manufactured by conventional methods. As a commercially available pigment, a green pigment "G59" manufactured by DIC Corporation can be used. [0039] The copper phthalocyanine pigment is not particularly limited and can be used. The following are examples of color index numbers. CI Pigment Blue 15, 15: 1, 15: 2, 15: 3, 15: 4, 15: 6, 17: 1, CI Pigment Green 7, 36. [0040] The content of the phthalocyanine pigment contained in the pigment dispersion is preferably 8 to 18% by weight, more preferably 10 to 16% by weight. [0041] The pigment dispersion may contain other pigments in addition to the phthalocyanine pigment. As these other pigments, if they are exemplified by color index numbers, they are, for example, CI Pigment Yellow 1, 2, 12, 13, 14, 16, 17, 20, 24, 31, 32, 34, 35, 36, 37, 40. , 41, 42, 43, 48, 53, 55, 61, 62, 63, 65, 73, 74, 75, 81, 83, 108, 109, 110, 111, 120, 125, 126, 129, 133, 138 , 139, 142, 150, 151, 153, 154, 155, 158, 160, 162, 164, 165, 168, 169, 170, 172, 174, 175, 176, 180, 181, 182, 183, 184, 185 , 189, 190, 191, 192, 193, 194, 195, 196, 197, 198, 199, 200, 202, 203, 204, 205, 206, 207, 208, CI Pigment Blue 1, CI Pigment Orange 23. Moreover, you may add a dye as needed. [0042] The pigment content other than the phthalocyanine pigment can be appropriately determined according to the purpose. It is approximately 1 to 8 parts by weight based on 100 parts by weight of the phthalocyanine pigment. [0043] The average particle diameter (average primary particle diameter) of the primary particles of the phthalocyanine pigment can be appropriately adjusted within a range that does not affect the contrast and the like. The average primary particle diameter is preferably 10 to 100 nm, more preferably 10 to 50 nm, and particularly preferably 10 to 30 nm. The primary particle diameter can be measured from an image obtained by photographing a pigment at a magnification of 100,000 times with a transmission electron microscope, for example. The average primary particle size is, for example, 100 particles that can be measured, and the average value is the average primary particle size. [0044] According to an embodiment of the present invention, depending on the type of pigment, a grinding process may be performed in advance from the viewpoint of adjusting the average primary particle diameter and the like. The grinding treatment can be performed according to a predetermined method depending on the type of pigment and the like. Examples of such a grinding process include a solvent soft grinding method and the like. [0045] Examples of the dispersant include a resin-type dispersant, a surfactant-type dispersant, and the like. Moreover, based on the difference between the acid value and the amine value of the resin, the resin type dispersant includes an acid value type dispersant with an amine value of 0 and an acid value greater than 0, and an amine value type dispersion with an acid value of 0 and an amine value greater than 0 Agent, and dispersant with acid value and amine acid value greater than 0. [0046] Examples of the resin-based dispersant include, for example, polyurethane; polyester; unsaturated polyamine; phosphate; polycarboxylic acid and its amine salt, ammonium salt, alkylamine salt; polycarboxylic acid ester; Polycarboxylates containing lead groups; polysiloxanes; modified polyacrylates; alginates, polyvinyl alcohol, hydroxypropyl cellulose, carboxymethyl cellulose, hydroxyethyl cellulose, methyl cellulose, Water-soluble polymer compounds such as polyvinylpyrrolidone and gum arabic; styrene-acrylic resin, styrene-methacrylic resin, styrene-acrylic-acrylate resin, styrene-maleic resin, styrene- Ethylene-containing double bonds containing maleic acid resin, methacrylic acid-methacrylic acid resin, acrylic acid-acrylic acid resin, isobutylene-maleic acid resin, vinyl-ester resin, turpentine modified maleic acid resin, etc. Resins; amine-based resins such as polyallylamine, polyvinylamine, and polyethylenimine; etc. [0047] Among the resin-based dispersants, from the viewpoint of more exerting the effect of suppressing the increase in viscosity of the pigment dispersion and the effect of suppressing the decrease in contrast of the coating film, those having a tertiary amine group are preferred. [0048] A commercially available resin-based dispersant can be used. Specific examples of the commercially available products are as follows, but are not limited thereto. Japan LUBRIZOL Corporation: SOLSPERSE 3000, 9000, 13240, 17000, 20000, 24000, 26000, 27000, 28000, 32000, 32500, 36000, 38500, 39000, 55000, 41000, BYK JAPAN Co., Ltd .: Disperbyk 108, 110 , 112, 140, 142, 145, 161, 162, 163, 164, 166, 167, 171, 174, 182, 190, 2000, 2001, 2050, 2070, 2150, LPN6919, LPN22101, LPN21116, BASF company system: EFKA 4401, 4403, 4406, 4330, 4340, 4010, 4015, 4046, 4047, 4050, 4055, 4060, 4080, 5064, 5207, 5244, Ajinomoto Precision Technology Co., Ltd .: AJISPER-PB821 (F), PB822 , PB880, manufactured by Kawaken Precision Chemical Co., Ltd .: HINOACT T-8000, manufactured by Kusumoto Chemical Co., Ltd .: DISPARLON PW-36, DISPARLON DA-325, 375, 7301, Otsuka Chemical Co., Ltd .: TERPLUS D2015, etc. [0049] The molecular weight of the resin-based dispersant is not particularly limited, but the weight average molecular weight is preferably 1,000 to 100,000. [0050] The acid value and the amine value of the resin-based dispersant are determined by the functional group and the content contained in the resin constituting the resin-based dispersant. The acid value (acid value at the time of solid content conversion) can be obtained by a method according to DIN EN ISO 2114, and the amine value (the amine value at the time of solid content conversion) can be obtained by a method according to DIN 16945, for example. The acid value of the acid value type dispersant is not particularly limited, but is preferably 20 to 150 mgKOH / g, and the amine value type dispersant is not particularly limited, but is preferably 5 to 30 mgKOH / g. When the dispersant having an acid value and an amine value greater than 0 is not particularly limited, the acid value is preferably 5 to 50 mgKOH / g, and the amine value is preferably 5 to 50 mgKOH / g. [0051] As the surfactant dispersant, corresponding to ionicity, examples include anionic active agents (anionic) such as naphthalenesulfonic acid formaldehyde condensate salt, aromatic sulfonic acid formaldehyde condensate, polyoxyethylene alkyl phosphate, and the like. Nonionic active agents (nonionic) such as polyoxyethylene alkyl ethers, cationic active agents (cationic) such as alkylamine salts, quaternary ammonium salts, and the like. Various surfactant-type dispersants are also commercially available, and specific examples thereof are as follows, but not limited thereto. Kao Corporation: DEMOL N, RN, MS, SN-B, EMULGEN 120, 430, ACETAMIN 24, 86, COTAMIN 24P, Nikko Chemical Co., Ltd .: NIKKOL BPS-20, BPS-30, DHC-30, BPSH-25, First Industrial Pharmaceutical Co., Ltd .: PLYSURF AL, A208F, LION Co., Ltd .: ALUCARD C-50, T-28, T-50, etc. [0052] The dispersant may be only one kind, or a combination of two or more kinds. When two or more types are combined, for example, in the case of a resin-based dispersant, it is a combination of resins that are different from each other, an acid value type and an amine value type, and in a surfactant type dispersant, it is a combination of different ionic properties (for example, anions). Type, non-ionic type, etc.), but is not limited to this. [0053] The content of the dispersant (solid content or active ingredient) in the pigment dispersion is preferably 2 to 20 based on 100 parts by weight of the phthalocyanine pigment (total if other pigments are included) from the viewpoint of dispersion stability. It is more preferably 5 to 10 parts by weight. However, the optimum amount of the dispersant should be appropriately adjusted by combining with the type of pigment used. When a pigment derivative described later is used, the content of the phthalocyanine pigment means the total amount including the pigment derivative. [0054] In the embodiment of the present invention, in addition to the dispersant described above, in order to disperse the phthalocyanine pigment in the pigment dispersion more stably, a pigment derivative may be used as a dispersion aid. When a pigment derivative is used, a pigment derivative having an affinity or a polar group introduced into the dispersant is adsorbed on the surface of each pigment, and the pigment derivative can be used as an adsorption point of the dispersant. In this case, since a dispersant is present on the surface of the pigment through the pigment derivative, each pigment can be dispersed more stably in the pigment dispersion as fine particles. Moreover, it is also possible to prevent the re-agglutination more effectively. [0055] The pigment derivative is specifically a compound that uses a pigment as a parent skeleton and introduces an acidic group, a basic group, or an aromatic group as a substituent into a side chain. The pigments that serve as the parent skeleton are specifically quinacridone-based pigments, phthalocyanine-based pigments, azo-based pigments, quinophthalone-based pigments, isoindoline-based pigments, isoindolinone-based pigments, and quinoline pigments. , Diketopyrrolopyrrole pigments, benzimidazolone pigments, dioxazine-based pigments, and the like. In addition, as the parent skeleton, light yellow aromatic polycyclic compounds such as naphthalene-based, anthraquinone-based, triazine-based, and quinoline-based compounds, which are not generally referred to as pigments, are also included. [0056] As the pigment derivative, Japanese Patent Application Laid-Open No. 11-49974, Japanese Patent Application Laid-Open No. 11-189732, Japanese Patent Application Laid-Open No. 10-245501, Japanese Patent Application Laid-Open No. 2006-265528, and Japanese Patent Application Laid-Open No. 8- Those described in JP 295810, JP 11-199796, JP 2005-234478, JP 2003-240938, and JP 2001-356210. [0057] The content (solid content) of the pigment derivative in the pigment dispersion is preferably from 2 to 15 parts by weight based on 100 parts by weight of the total of the phthalocyanine pigment and the pigment contained as needed from the viewpoint of dispersion stability. , More preferably 5 to 10 parts by weight. However, the optimum addition amount of the pigment derivative should be appropriately adjusted by a combination with the type of pigment and dispersant used, and the like. In addition, a total of 100 parts by weight of the "phthalocyanine pigment and the pigment contained as needed" means a total amount that does not include a pigment derivative. [0058] In the pigment dispersant, from the viewpoint of further improving the dispersibility of the phthalocyanine pigment and the like in the pigment dispersion and the coloring composition, in addition to the dispersant, a dispersing resin may be used as a dispersing aid. These dispersion resins are particularly preferably used when the coating film-forming component used in the coloring composition described later contains a polymerizable component, especially a photopolymerizable component. Examples of such dispersion resins include alkali-soluble resins described later. The dispersing resin may be the same kind of resin as the alkali-soluble resin used in the coloring composition, or it may be a different kind of resin. The content of the dispersing resin is preferably 10 to 50 parts by weight based on 100 parts by weight of the phthalocyanine pigment (total if other pigments are included). When a pigment derivative is used, the content of the phthalocyanine pigment (total if other pigments are included) means the total amount including the pigment derivative. [0059] The solvent can be appropriately selected depending on the type of the coating film-forming component described later, and examples thereof include various organic solvents such as aromatic, ketone, ester, glycol ether, alcohol, and aliphatic solvents. Among them, an organic solvent selected from aromatic, ketone, ester, and glycol ether systems is preferred from the viewpoint of coating film formability. The organic solvent may be only one type, or two or more types may be combined. [0060] Examples of the aromatic organic solvent include aromatic hydrocarbons such as toluene, xylene, and ethylbenzene. [0061] Examples of the ketone-based organic solvent include methyl ethyl ketone, methyl isobutyl ketone, diisobutyl ketone, acetoacetone, isophorone, acetophenone, and cyclohexanone. Examples of the ester-based organic solvent include ethyl acetate, n-butyl acetate, isobutyl acetate, isopropyl acetate, methyl propionate, 3-methoxybutyl acetate, and ethyl glycol acetate. Ester, propylene glycol monomethyl ether acetate (PMA), propylene glycol monoethyl ether acetate, 3-methyl-3-methoxybutyl acetate, methyl monochloroacetate, ethyl monochloroacetate, butyl monochloroacetate Esters, ethyl acetate, ethyl acetate, butyl carbitol acetate, butyl lactate, ethyl 3-ethoxypropionate, ethylene glycol monobutyl ether acetate, ethylene glycol Monomethyl ether acetate, propyl acetate, 1,3-butanediol diacetate, and the like. [0063] Examples of glycol ether-based organic solvents include ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, ethylene glycol monobutyl ether, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, and diethyl ether. Diethylene glycol mono-n-propyl ether, ethylene glycol mono-isopropyl ether, diethylene glycol mono-isopropyl ether, ethylene glycol mono-n-butyl ether, diethylene glycol mono-n-butyl ether, triethylene glycol mono-n-butyl ether, Ethylene glycol monotertiary butyl ether, diethylene glycol monotertiary butyl ether, 1-methyl-1-methoxybutanol, propylene glycol monomethyl ether, propylene glycol monoethyl ether, propylene glycol monotertiary butyl ether, propylene glycol mono Water solubility of n-propyl ether, propylene glycol monoisopropyl ether, dipropylene glycol monomethyl ether, dipropylene glycol monoethyl ether, dipropylene glycol mono-n-propyl ether, dipropylene glycol monoisopropyl ether, propylene glycol mono-n-butyl ether, dipropylene glycol mono-n-butyl ether Glycol ethers, ethylene glycol monohexyl ether, ethylene glycol-2-ethylhexyl ether, ethylene glycol phenyl ether, diethylene glycol n-hexyl ether, diethylene glycol-2-ethylhexyl ether, propylene glycol Monobutyl ether, dipropylene glycol monobutyl ether, dipropylene glycol propyl ether, propylene glycol methyl ether propionate and other water-insoluble glycol ethers. [0064] Examples of the alcohol-based organic solvent include alkanols having 1 to 4 carbon atoms such as ethanol, methanol, butanol, propanol, isopropanol, and the like, ethylene glycol, propylene glycol, diethylene glycol, and pentamethylene Diethylene glycol, trimethylene glycol, 2-butene-1,4-diol, 2-ethyl-1,3-hexanediol, 2-methyl-2,4-pentanediol, tripropylene glycol, molecular weight Polyethylene glycol up to 2000, 1,3-propanediol, isopropanediol, isobutanediol, 1,4-butanediol, 1,3-butanediol, 1,5-pentanediol, 1,6- Hexylene glycol, glycerol, erythritol, pentaerythritol and the like. [0065] Examples of the aliphatic organic solvent include aliphatic hydrocarbons such as n-pentane, n-hexane, and n-heptane. [0066] When the solvent is added to prepare a coloring composition to be described later, from the viewpoint of handleability, a solid content concentration including a phthalocyanine pigment or the like may be added to 50 to 85% by weight. [0067] The pigment dispersion may contain other additives in addition to the aforementioned components. [0068] The pigment dispersion can be obtained, for example, by adding the aforementioned components to a conventional dispersing machine such as a bead mill, a sand mill, or a disperser, and dispersing it. That is, a solid dispersion of a pigment-dispersed phthalocyanine pigment or the like is dispersed as particles in a solvent. Here, the term “particles” means secondary particles formed by aggregating the aforementioned phthalocyanine pigment or primary particles of other pigments which are necessary to be contained. [0069] The average particle diameter of the particles dispersed in the pigment dispersion obtained as described above (hereinafter sometimes referred to as "dispersed average particle diameter") is not particularly limited, but those having a diameter of approximately 30 to 300 nm can be preferably used. In addition, from the viewpoint of the surface smoothness of the coating film, the dispersion average particle diameter is more preferably from 30 to 150 nm. The dispersed average particle diameter can be measured by, for example, a particle diameter measuring machine. Examples of the particle size measuring device include FPAR-1000 manufactured by Otsuka Electronics Co., Ltd. and the like. [0070] <Coloring composition> An embodiment of the coloring composition of the present invention includes the pigment dispersion and a coating film forming component described above. By containing the pigment dispersion in this way, it is possible to suppress a decrease in the contrast of the coating film after the coloring composition is prepared. In addition, since the viscosity increase after the pigment dispersion is suppressed is suppressed, the pigment dispersion is easy to handle and the coloring composition can be easily prepared. [0071] The coating film forming component is not particularly limited as long as it is a component capable of forming a coating film, and may be a polymerizable component, a polymer, or a mixture thereof. The polymerizable component is preferably a photopolymerizable component because it can be easily patterned by development (negative development). Examples of the polymer include thermoplastic urethane resins, (meth) acrylic resins, polyamide resins, polyimide resins, styrene and maleic resins, and polyester resins. Resin, silicone resin, cardo resin, etc. The molecular weight of the polymer can be appropriately determined. [0072] The photopolymerizable component that can be used includes a photopolymerizable compound and a photopolymerization initiator. As such a photopolymerizable compound and a photopolymerization initiator, for example, those described in Japanese Patent Application Laid-Open No. 2009-179789 can be used. If detailed, these photopolymerizable compounds are addition polymerizable compounds having at least one ethylenically unsaturated double bond, and are selected from compounds having at least one, preferably two or more terminal ethylenically unsaturated bonds. . These compounds are widely known in the technical field, and they may be used in the present invention without particular limitation. The photopolymerizable compound has, for example, a chemical form of a monomer, a prepolymer, that is, a dimer, a trimer, and an oligomer, or a mixture thereof and a copolymer thereof. [0073] Examples of the monomer and its copolymer include unsaturated carboxylic acids (for example, acrylic acid, methacrylic acid, itaconic acid, crotonic acid, isocrotonic acid, maleic acid, etc.), or esters thereof, and As the amine, an ester of an unsaturated carboxylic acid and an aliphatic polyhydric alcohol compound, and an amine of an unsaturated carboxylic acid and an aliphatic polyamine compound are preferably used. It is also possible to preferably use an addition reactant of an unsaturated carboxylic acid ester or amidoamine having a nucleophilic substituent such as a hydroxyl group or an amine group or a mercapto group with a monofunctional or polyfunctional isocyanate or epoxy, and Dehydration condensation reactants with monofunctional or polyfunctional carboxylic acids, etc. It is also preferably an addition reactant of an unsaturated carboxylic acid ester or amidoamine having an electrophilic substituent such as an isocyanate group or an epoxy group, and a monofunctional or polyfunctional alcohol, amine, or thiol. Furthermore, it is a substitution reaction product of unsaturated carboxylic acid esters or amidines having a detachable substituent such as a halogen group or tosylsulfonyloxy group, and monofunctional or polyfunctional alcohols, amines, and thiols. As another example, instead of the unsaturated carboxylic acid described above, a group of compounds substituted with unsaturated phosphonic acid, styrene, vinyl ether, or the like may be used. [0074] These specific examples are roughly described in Japanese Patent Application Laid-Open No. 2009-179789, but as specific examples of the monomer of an aliphatic polyol compound and an ester of an unsaturated carboxylic acid, ethylene glycol is used as an acrylate. Diacrylate, triethylene glycol diacrylate, 1,3-butanediol diacrylate, tetramethylene glycol diacrylate, propylene glycol diacrylate, neopentyl glycol diacrylate, trimethylol Propane triacrylate, trimethylolpropane tri (acryloxypropyl) ether, trimethylolethane triacrylate, hexanediol diacrylate, 1,4-cyclohexanediol diacrylate, Tetraethylene glycol diacrylate, pentaerythritol diacrylate, pentaerythritol triacrylate, pentaerythritol tetraacrylate, dipentaerythritol diacrylate, dipentaerythritol hexaacrylate, dipentaerythritol pentaacrylate, sorbitol triacrylate, sorbose Alcohol tetraacrylate, sorbitol pentaacrylate, sorbitol hexaacrylate, tris (acryloxyethyl) isocyanurate, polyester acrylate oligomer, isocyanurate EO modified three Acrylate . [0075] With regard to these addition polymerizable compounds, the details of the structure, the use method alone or in combination, the amount of use, etc. can be arbitrarily set in accordance with the performance design of the final colored composition. For example, it is selected based on the following viewpoints. In terms of sensitivity, a structure having a large amount of unsaturated groups per molecule is preferred, and in most cases, it is preferably bifunctional or more. In addition, in order to improve the strength of the cured film, it is preferable to use three or more functional groups, and then use a combination of different functional groups and different polymerizable groups (such as acrylate, methacrylate, styrene-based compound, vinyl ether-based compound), The method of adjusting both sensitivity and intensity is also effective. [0076] In addition, for compatibility and dispersibility with other components in the coloring composition (such as an adhesive polymer such as an alkali-soluble resin, a photopolymerization initiator, and a colorant (pigment)), the addition of a polymer compound Selection and use are also important factors. For example, compatibility may be improved by using a low-purity compound or using two or more types in combination. [0077] In addition, a specific structure may be selected for the purpose of improving adhesion to a substrate or the like. The photopolymerizable compound preferably contains 5 to 70% by weight, and more preferably 10 to 60% by weight, with respect to the nonvolatile components in the coloring composition. These may be used alone or in combination of two or more. In addition, the method of using the photopolymerizable compound can be arbitrarily selected with an appropriate structure, blending, and addition amount based on the viewpoints of the size of oxygen polymerization inhibition, resolution, covering property, refractive index change, surface adhesion, and the like. [0078] As the photopolymerization initiator, those described in Japanese Patent Application Laid-Open No. 2009-179789 can also be used. For example, acetophenone-based, acetal-based, benzophenone-based, benzoin-based, benzamidine-based, xanthone-based, active halogen compounds (triazine-based, oxadiazole-based, coumarin-based) ), Acridine-based, bisimidazole-based, oxime ester-based, and the like. As specific examples of these, as specific examples of the benzophenone-based photopolymerization initiator, for example, benzophenone, 4,4'-bis (dimethylamino) benzophenone, 4,4 ' -Bis (diethylamino) benzophenone, 4,4'-dichlorobenzophenone and the like. [0079] The content of the photopolymerization initiator in the coloring composition is preferably 0.1 to 10.0% by mass, and more preferably 0.5 to 5.0% by mass relative to the total solid content of the coloring composition. When the content of the photopolymerization initiator is within this range, the polymerization reaction proceeds well and a film with good strength can be formed. [0080] When the photopolymerizable component is contained in the coloring composition as a coating film forming component, an alkali-soluble resin may be contained in addition to the pigment dispersion and the photopolymerizable component. [0081] When an alkali-soluble resin is contained in the coloring composition, for example, when the coloring composition is applied to the pattern formation in the photolithography step, the pattern formation property can be further improved. [0082] As these alkali-soluble resins, those described in Japanese Patent Application Laid-Open No. 2009-179789 can be used. In short, as the alkali-soluble resin, for example, a linear organic polymer and at least one molecule (preferably, a molecule having an acrylic copolymer or a styrene-based copolymer as a main chain) can promote alkali solubility. The base (for example, a carboxyl group, a phosphoric acid group, a sulfonic acid group, or the like) is appropriately selected from alkali-soluble resins. Among them, those which are more soluble in organic solvents and can be developed by weakly alkaline aqueous solutions are more preferable. [0083] As the alkali-soluble resin, a copolymer of (meth) acrylic acid and other monomers copolymerizable therewith is particularly exemplified. Herein, the general term for (meth) acrylic acrylic acid and methacrylic acid is collectively referred to below as the general term for (meth) acrylic acid acrylic ester and methacrylic acid ester. [0084] Examples of other monomers that can be copolymerized with (meth) acrylic acid include alkyl (meth) acrylate, aryl (meth) acrylate, vinyl compounds, and the like. Here, the hydrogen atoms of the alkyl group and the aryl group may be substituted with a substituent. [0085] Specific examples of the alkyl (meth) acrylate and aryl (meth) acrylate include methyl (meth) acrylate, ethyl (meth) acrylate, propyl (meth) acrylate, and the like. Butyl (meth) acrylate, isobutyl (meth) acrylate, amyl (meth) acrylate, hexyl (meth) acrylate, octyl (meth) acrylate, phenyl (meth) acrylate, ( Benzyl (meth) acrylate, toluene (meth) acrylate, naphthyl (meth) acrylate, cyclohexyl (meth) acrylate, and the like. Examples of the vinyl compound include styrene, α-methylstyrene, vinyl toluene, glycidyl methacrylate, glycidyl acrylate, acrylonitrile, vinyl acetate, and N-vinylpyrrolidine Ketone, tetrahydrofurfuryl methacrylate, polystyrene macromonomer, polymethyl methacrylate macromonomer, CH ₂ = CR ⁵ R ⁶ , CH ₂ = C (R ⁵ ) (COOR ⁷ ) (Here, R ⁵ Represents a hydrogen atom or an alkyl group having 1 to 5 carbon atoms, and R ⁶ Represents an aromatic hydrocarbon ring with 6 to 10 carbon atoms, R ⁷ Represents an alkyl group having 1 to 8 carbons or an aralkyl group having 6 to 12 carbons. [0087] These copolymerizable other monomers may be used alone or in combination of two or more. [0088] The weight average molecular weight of the alkali-soluble resin is preferably 5,000 to 50,000 from the viewpoint of developability. [0089] Various types of alkali-soluble resins are commercially available, and specific examples thereof are as follows, but not limited thereto. Showa Polymer Co., Ltd .: RIPOXY SPC-2000, Mitsubishi Electric Co., Ltd .: DIANAL NR series, Diamond hamrock Co., Ltd., Photomer 6173 (COOH-containing polyurethane acrylic oligomer ), Manufactured by Osaka Organic Chemical Industry Co., Ltd .: BISCOT R-264, KS photoresist 106, SOP-005, DAICEL Chemical Industry Co., Ltd .: CYCLOMER P series, BLACKCELL CF200 series, DAICEL UCB Co., Ltd .: Ebecryl 3800, Japan Catalyst Corporation: ACRYCURE (registered trademark) RD-Y-503, RD-Y-702-A, etc. [0090] The content of the alkali-soluble resin in the coloring composition is preferably 1 to 20% by mass, more preferably 2 to 15% by mass, and particularly preferably 3 to 12% by weight relative to the total solid content of the coloring composition. %. When contained in a pigment dispersion as a dispersing resin, it is total. [0091] When the coloring composition contains a photopolymerizable component as a coating film-forming component, it may contain a solvent in addition to the pigment dispersion, the photopolymerizable component, and the alkali-soluble resin. It can be prepared well by using a solvent. [0092] Examples of such solvents are esters such as ethyl acetate, n-butyl acetate, isobutyl acetate, amyl formate, isoamyl acetate, isobutyl acetate, butyl propionate, isopropyl butyrate , Ethyl butyrate, butyl butyrate, alkyl esters, methyl lactate, ethyl lactate, methyl oxyacetate, ethyl oxyacetate, butyl oxyacetate, methyl methoxyacetate, methoxyacetic acid Ethyl acetate, butyl methoxyacetate, methyl ethoxyacetate, ethyl ethoxyacetate; methyl 3-oxypropionate, ethyl 3-oxypropionate, etc. Esters; methyl 3-methoxypropionate, ethyl 3-methoxypropionate, methyl 3-ethoxypropionate, ethyl 3-ethoxypropionate, methyl 2-oxypropionate Esters, ethyl 2-oxypropionate, propyl 2-oxypropionate, methyl 2-methoxypropionate, ethyl 2-methoxypropionate, propyl 2-methoxypropionate, Methyl 2-ethoxypropionate, ethyl 2-ethoxypropionate, methyl 2-oxy-2-methylpropionate, ethyl 2-oxy-2-methylpropionate, 2- Methyl methoxy-2-methylpropionate, ethyl 2-ethoxy-2-methylpropionate, methyl pyruvate, ethyl pyruvate, propyl pyruvate, ethyl Methyl acetate, ethyl acetate, methyl 2-oxobutanoate, ethyl 2-oxobutanoate, etc .; ethers, such as diethylene glycol dimethyl ether, tetrahydrofuran, ethylene glycol monomethyl ether, Ethylene glycol monoethyl ether, methyl cellulose acetate, ethyl cellulose acetate, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, diethylene glycol monobutyl ether, propylene glycol monomethyl ether, Propylene glycol monomethyl ether acetate, propylene glycol monoethyl ether acetate, propylene glycol propyl ether acetate, etc .; ketones, such as methyl ethyl ketone, cyclohexanone, 2-heptanone, 3-heptanone, etc .; aromatic Hydrocarbons such as toluene, xylene; etc. The solvents may be used alone or in combination of two or more. [0093] The content of the solvent in the coloring composition is based on the type and content of the solvent in the pigment dispersion, and is preferably contained so that the total solid content (non-volatile content) content of the coloring composition becomes 15 to 50% by mass. . [0094] When a polymer is used as the coating film forming component, a solvent can be used in the same manner as in the case of using a photopolymerizable component. As such a solvent, it can be used by a user in the said pigment dispersion, and it can also be used by a user with a photopolymerizable component. [0095] In this case, the content of the solvent in the coloring composition is based on the type and content of the solvent in the pigment dispersion. It is preferable that the total solid content (non-volatile content) of the coloring composition is 15 to 50 mass. Contains in% way. [0096] In the coloring composition, a dispersing assistant, a sensitizer (sensitizing dye), a chain transfer agent, a fluorine-based organic compound, a thermal polymerization initiator, a thermal polymerization component, a filler, and an interfacial activity may be added as necessary. Various additives such as agents, adhesion promoters, antioxidants, agglutination inhibitors, and surface conditioners (leveling agents). When the pigment dispersion is contained, the amount of addition may be adjusted. [0097] The coloring composition is obtained by adding a coating film-forming component to a pigment dispersion and agitating with a disperser or the like. [0098] A coating film formed using the coloring composition can suppress a decrease in contrast after the coloring composition is prepared. Therefore, a coloring composition containing the aforementioned pigment dispersion can form a color filter well. [Examples] [0099] Examples, comparative examples, and reagents used in the control described below are as follows. [0100] (1) Pigment · CI Pigment Green 59 Product name "FASTOGEN GREEN C100" (referred to as "C100" in the table), manufactured by DIC Corporation. It is a zinc bromide zinc phthalocyanine pigment, and the average number of hydrogen atoms contained in one molecule is 2 or more. ‧CI Pigment Blue 15: 6 Product name CYANINE BLUE A540, manufactured by DIC Corporation. Is a copper phthalocyanine pigment. (2) phthalimide and its derivatives ‧ phthalimide: manufactured by Tokyo Chemical Industry Co., Ltd. ‧ phthalimide acetic acid: manufactured by Tokyo Chemical Industry Co., Ltd. ‧N-butylphthalimide: manufactured by Tokyo Chemical Industry Co., Ltd. ‧Phthalidene imine: manufactured by Tokyo Chemical Industry Co., Ltd. Tetrachlorophthalimide acetic acid manufactured by Accel Pharmtech: Reference Manufacturing Example 3. ‧Tetrabromophthalimidineacetic acid: Refer to Manufacturing Example 4. ‧3-Tetrachlorophthalimidine propionic acid: Refer to Manufacturing Example 1. ‧3-tetrabromophthalimidine propionic acid: Refer to Manufacturing Example 5. ‧N- (2-hydroxyethyl) phthalimide: manufactured by Tokyo Chemical Industry Co., Ltd.‧2-tetrachlorophthalimide ethane phosphoric acid: Reference Manufacturing Example 2. (3) Dispersant ‧Disperbyk-LPN6919, manufactured by BYK JAPAN Co., Ltd., resin type dispersant with tertiary amine group ‧SOLSPERSE 41000, manufactured by Japan LUBRIZOL Co., Ltd., resin type dispersant [0103] (4 ) Solvent: propylene glycol monomethyl ether acetate (hereinafter referred to as "PMA"). ‧ Propylene glycol monomethyl ether (hereinafter referred to as "PM"). [0104] (5) Dispersion resin ACRYCURE (registered trademark) RD-Y-702-A, manufactured by Japan Catalyst Co., Ltd. [Production Example 1] Production of phthalimide derivative (3-tetrachlorophthalimide propionic acid) A 100 ml pear-shaped flask was fixed in an oil bath, and propylene glycol monomethyl ether was fed. (Hereinafter referred to as "PM") 75 g, 20.02 g (70 mmol) of tetrachlorophthalic anhydride, 6.24 g (70 mmol) of β-alanine, and a cooling tube was installed in the upper part, and the oil bath was heated while stirring with a magnetic stirrer. After the temperature reached 130 ° C, the target was immediately precipitated, so the stirring was continued for 5 minutes. Then, it cooled to room temperature, 25g of PM was added, and stirring was continued for 30 minutes. The contents were filtered with a magnetic funnel, and the residue was washed with pure water and then dried at 100 ° C for 18 hours. The yield was 18.7 g (74% yield). The dried product was 3-tetrachlorophthalimide propionic acid, which is a phthalimide derivative, and was used in the examples described later. MALDI-TOF-MS mass spectrometer AXIMA CFR plus (manufactured by Shimadzu Corporation) was used in the negative mode spectrum of 2,5-dihydroxybenzoic acid (DHBA) in the matrix to confirm that the target substance (m / z 355 ) Crest. (Production Example 2) Production of phthalimide derivative (2-tetrachlorophthalimide ethane phosphoric acid) A 500 ml 4-necked flask was fixed in an oil bath, and 200 g of PM was fed. , 41.95g (150mmol) of tetrachlorophthalic anhydride, 20.7g (150mmol) of O-phosphoranylethanolamine, 33.65g (300mmol) of 1,4-diazabicyclo [2.2.2] -octane, in the upper part A cooling tube was set, and the mixture was heated under reflux with a magnetic stirrer for 6 hours. After cooling to room temperature, the contents were filtered with a magnetic funnel, and the residue was washed with PM. After the residue was further dispersed in 1.5 L of methanol for 30 minutes, 300 g of 35% hydrochloric acid was added and stirred for 30 minutes. The contents were filtered with a magnetic funnel, and the residue was washed with a small amount of methanol and then dried. The yield was 42 g (69% yield). The dried product was 2-tetrachlorophthalimide ethane phosphate of a phthalimide derivative, and was used in Examples described later. Negative type using α-cyano-4-hydroxycinnamic acid (CHCA) and 2,5-dihydroxybenzoic acid (DHBA) in the matrix obtained from MALDI-TOF-MS mass spectrometer AXIMA CFR plus (manufactured by Shimadzu Corporation) In the spectrum of the mode, a peak of the object (m / z 407) was confirmed. [Production Example 3] Production of phthalimidine derivative (tetrachlorophthalimide acetic acid) was performed in the same manner as in Production Example 1 except that 70 mmol of β-alanine was 70 mmol of glycine. Operations were performed under the same conditions to obtain a dried product. The yield was 15.12 g (63% yield). The dried product was tetrachlorophthalimide acetic acid, which is a phthalimide derivative, and was used in Examples described later. Negative type using α-cyano-4-hydroxycinnamic acid (CHCA) and 2,5-dihydroxybenzoic acid (DHBA) in the matrix obtained from MALDI-TOF-MS mass spectrometer AXIMA CFR plus (manufactured by Shimadzu Corporation) In the spectrum of the mode, a peak of the object (m / z 341) was confirmed. [Production Example 4] Production of phthalimide derivative (tetrabromophthalimideacetic acid) Except that 70 mmol of β-alanine was 70 mmol of glycine, and tetrachloro phthalate 70 mmol of dicarboxylic acid was changed to 70 mmol of tetrabromophthalic acid, and a dried product was obtained in the same manner as in Production Example 1. The yield was 26.24 g (72% yield). The dried product was tetrabromophthalimide acetic acid, which is a phthalimide derivative, and was used in Examples described later. Negative type using α-cyano-4-hydroxycinnamic acid (CHCA) and 2,5-dihydroxybenzoic acid (DHBA) in the matrix obtained from MALDI-TOF-MS mass spectrometer AXIMA CFR plus (made by Shimadzu Corporation) In the spectrum of the mode, a peak of the object (m / z 517) was confirmed. (Production Example 5) Production of an phthalimide derivative (3-tetrabromophthalimide propionic acid) except that 70 mmol of tetrachlorophthalic acid was used as tetrabromophthalate Except for 70 mmol of formic acid, operation was performed under the same conditions as in Production Example 1 to obtain a dried product. The yield was 28.08 g (yield 75%). The dried product was 3-tetrabromophthalimide propionic acid, which is a phthalimide derivative, and was used in the examples described later. Negative type using α-cyano-4-hydroxycinnamic acid (CHCA) and 2,5-dihydroxybenzoic acid (DHBA) in the matrix obtained from MALDI-TOF-MS mass spectrometer AXIMA CFR plus (manufactured by Shimadzu Corporation) In the spectrum of the mode, a peak of the object (m / z 531) was confirmed. [Comparative 1] <Production of Pigment Dispersion> 38.40 g of CI Pigment Green 59 (FASTOGEN GREEN C100), a dispersant (Disperbyk-LPN6919), and a dispersant ( ACRYCURE (registered trademark) RD-Y-702-A) 23.59 g, 75.98 g of PMA as a solvent. After stirring at 2000 revolutions for 10 minutes, 640 g of φ0.8 mm zirconia beads were charged, and dispersion treatment was performed at 2000 revolutions for 30 minutes. 30.28 g of PMA and 1.72 g of a dispersant (SOLSPERSE 41000, manufactured by Japan Lubrizol) were further added to the dispersion treatment liquid, and dispersion treatment was performed at 2000 revolutions for 10 minutes. 160 g of the dispersion treatment liquid from which φ0.8 mm zirconia beads were removed was put into another pot together with 640 g of φ 0.1 mm zirconia beads, and the dispersion treatment was performed at 2000 revolutions for 60 minutes. After 77.04 g of PMA was added, dispersion treatment was performed at 1500 revolutions for 10 minutes, and φ0.1 mm zirconia beads were removed to obtain a green pigment dispersion. [0111] <Production of colored composition> ACRYCURE (registered trademark) BX-Y-10, 26.0 weight, manufactured by Nippon Catalysts Co., Ltd. as a (meth) acrylic polymer containing 12.0% by weight (pure content) was prepared. % Pentaerythritol (six / five) acrylate (Kayrad DPHA, manufactured by Nippon Kayaku Co., Ltd.) as a photo-polymerizable polyfunctional acrylate monomer, and 4.0% by weight of BASF Japan as a photopolymerization initiator Irgacure 369 manufactured by the company, 58.0% by mass of a coating film forming component of PMA as a solvent. A coating film-forming component was added to the obtained green pigment dispersion and stirred with a disperser to obtain a colored composition. The addition amount of the coating film-forming component was 4.0 g with respect to 6.0 g of the green pigment dispersion. [Examples 1 to 9 and Comparative Example 1] <Production of Pigment Dispersion> Except for CI Pigment Green 59 (FASTOGEN GREEN C100) and phthalimide or its derivatives, the addition amounts are shown in Table 1. Except for the description, as in Control 1, a green pigment dispersion was obtained. [0113] <Production of Colored Composition> Using the obtained green pigment dispersion, in the same manner as in Control 1, a colored composition was obtained. [Comparative 2] <Production of Pigment Dispersion> CI Pigment Blue 15: 6 (FASTGEN BLUE A540) 30.72 g, Dispersant (Disperbyk-LPN6919), Dispersant (Disperbyk-LPN6919), 21.28 g, Dispersion 42.44 g of resin (ACRYCURE (registered trademark) RD-Y-702-A), 1.28 g of phthalimidine derivative of Production Example 2, 38.68 g of PMA as a solvent, and 25.60 g of PM. After stirring at 2000 revolutions for 10 minutes, 640 g of φ0.8 mm zirconia beads were charged, and dispersion treatment was performed at 2000 revolutions for 30 minutes. To this dispersion treatment solution, 28.24 g of PMA was further added, and dispersion treatment was performed at 2000 revolutions for 10 minutes. 160 g of the dispersion treatment liquid from which φ0.8 mm zirconia beads were removed was put into another pot together with 640 g of φ 0.05 mm zirconia beads, and the dispersion treatment was performed at 2000 revolutions for 60 minutes. After adding 105.0 g of PMA, dispersion treatment was performed at 1500 revolutions for 10 minutes, and φ0.05 mm zirconia beads were removed to obtain a blue pigment dispersion. [0115] <Production of Colored Composition> Using the obtained blue pigment dispersion, in the same manner as in Control 1, a colored composition was obtained. [Examples 10 to 12] <Production of Pigment Dispersion> Except for the addition amounts of CI Pigment Blue 15: 6 (FASTGEN BLUE A540) and phthalimide derivatives, as described in Table 1, and In the same manner as in Control 2, a blue pigment dispersion was obtained. [0117] <Production of Colored Composition> Using the obtained blue pigment dispersion, in the same manner as in Control 2, a colored composition was obtained. [Evaluation] <Temperature Change of Viscosity of Pigment Dispersion> Using the E-type viscometer "RE-80L" manufactured by Toki Sangyo Co., Ltd., the pigment dispersions obtained in Controls, Examples, and Comparative Examples were measured immediately after production. Viscosity, viscosity after standing at 40 ° C for 3 days. The viscosity (mPa.s) measured for the pigment dispersions of each control, example, and comparative example is shown in Table 1. [0119] <Temperature Change of Contrast of Colored Composition> The contrast ratio of the pigment dispersion obtained in the control, the examples, and the comparative example immediately after production and the contrast ratio of the pigment dispersion obtained after standing at 40 ° C for 3 days were evaluated by the following methods. . A spin coater (manufactured by MIKASA Corporation, spin coater MS) for adjusting the number of revolutions so that the chromaticity of the green colored composition becomes x = 0.550 and the chromaticity of the blue composition becomes y = 0.107. -150A), coated on 1mm, 100mm square glass plates. The coated plate was allowed to stand at room temperature for 5 minutes, and then dried (pre-baked) at 80 ° C for 2 minutes in an air bath. In addition, an exposure device (manufactured by Sanyung Kogyo Co., Ltd., trade name: UVE-1001S type exposure light source device, YSH-100SA type ultra-high pressure mercury lamp) was used so as to be 60 mJ / cm ² The exposure intensity was irradiated to the coated plate with ultraviolet (UV), and post-baking was performed at 235 ° C for 60 minutes on green and 30 minutes on blue. The coated plate after the post-baking was sandwiched between a polarizing plate (trade name: POLAX-38S, manufactured by LUCEO Co., Ltd.) and installed on a lamp (trade name: HF-LS-100WLCG). A luminance meter (trade name: LS-100, manufactured by KONICA MINOLTA SENSING Co., Ltd.) was used to measure the brightness when the polarizing plate was in the orthogonal position and the brightness when the polarizing plate was in the parallel position, and the ratio (%) was calculated as the contrast. Table 1 shows the measurement results of the pigment dispersions for each control, example, and comparative example. The values are expressed as the ratio of each example and comparative example to the control, and evaluated based on the following criteria. When the ratio with respect to the control is 140 or more, it is recorded as ◎, when the ratio is 100 to 139, it is recorded as ○, and when the ratio is 0 to 99, it is recorded as ×. [0120]

Claims (8)

A pigment dispersion containing at least one selected from the group consisting of phthalimide and its derivative represented by the following formula (1), a phthalocyanine pigment, a dispersant, and a solvent, (In the formula (1), R ¹ to R ⁴ are a hydrogen atom or a halogen atom, Q is (i) a hydrogen atom, (ii) an alkane having 1 to 5 carbon atoms which may have a substituent X bonded to a terminal carbon atom. Or (iii) an aryl group which may have a substituent Y bonded to a carbon atom of the aromatic ring, the substituent X is an ethyl group, a carboxyl group, a phosphate group, or a sulfonic group, and the substituent Y is a methyl group, an ethyl group, Carboxyl, phosphate, or sulfonate). The pigment dispersion according to claim 1, wherein the phthalocyanine pigment is a metal phthalocyanine pigment. The pigment dispersion according to claim 2, wherein the metal phthalocyanine pigment is a zinc phthalocyanine pigment or a copper phthalocyanine pigment. The pigment dispersion of claim 3, wherein the zinc phthalocyanine pigment is a zinc halide phthalocyanine pigment having an average number of hydrogen atoms in the molecule of 2 or more. The pigment dispersion according to claim 4, wherein the zinc halide phthalocyanine pigment is a zinc bromide phthalocyanine pigment. The pigment dispersion according to any one of claims 1 to 5, wherein Q in the aforementioned formula (1) is (ii) an alkyl group having 2 carbon atoms which may have a substituent X bonded to a terminal carbon atom, and The substituent X is a carboxyl group or a phosphate group. A coloring composition comprising the pigment dispersion of any one of claims 1 to 6 and a coating film forming component. The coloring composition according to claim 7, further comprising a photopolymerizable component as the coating film forming component.