Azo dye, colored curable resin composition, color filter, display device, solid imaging device and production method of azo dye

Abstract

To provide an azo dye and a colored curable resin composition capable of forming a color filter with improved heat resistance and light resistance, and to provide a production method of an azo dye capable of forming the color filter.SOLUTION: An azo dye has a prescribed crystal structure, identified with a powder X-ray diffraction using a CuK α-ray of a compound of azo dye 50 pts. and aluminum oxide 50 pts. The azo dye is expressed, for instance, by a formula (AI-1) below.SELECTED DRAWING: None

Description

[Technical field]

[0001] The present invention relates to an azo dye, a colored curable resin composition containing the azo dye, a color filter formed from the colored curable resin composition, a display device and a solid-state imaging device each including the color filter, and a method for producing the azo dye. [Background technology]

[0002] As an azo dye, for example, a disazo pigment described in Patent Document 1, which is used in an ink composition, is known. [Prior art documents] [Patent documents]

[0003] [Patent Document 1] JP 2018-123321 A Summary of the Invention [Problem to be solved by the invention]

[0004] When an azo dye is used as a colorant contained in a colored curable resin composition capable of forming a color filter used in a display device such as a liquid crystal display device, an electroluminescent display device, and a plasma display device, or a solid-state imaging device such as a CCD or a CMOS sensor, if a conventionally known azo dye such as a disazo pigment described in Patent Document 1 is used, the heat resistance and light resistance of the formed color filter may not be fully satisfactory. Therefore, one of the objectives of the present invention is to provide an azo dye and a colored curable resin composition capable of forming a color filter with improved heat resistance and light resistance. Another objective of the present invention is to provide a method for producing an azo dye capable of forming a color filter with improved heat resistance and light resistance. [Means for solving the problem]

[0005] The gist of the present invention is as follows. [1] An azo dye represented by the following formula (I): The azo dye has a powder X-ray diffraction pattern obtained by using CuKα radiation for a mixture of 50 parts of the azo dye and 50 parts of aluminum oxide. There are peaks in the diffraction angle range (2θ±0.2°) = 5° to 25°, The maximum peak is at 9.8°~16.0°, and the maximum peak is at 5°~25°. At least one peak exists between 11.0° and 11.8°. Between the maximum peak intensity at 9.8°-16.0° (I1) and the maximum peak intensity at 11.0°-11.8° (I2), I2 / I1≧0.05 and Between the peak intensity (I3) at the diffraction angle (2θ±0.2°)=35.1° due to aluminum oxide and the I1, I1 / I3≧0.35 Azo dyes meet the following requirements. [ka] [In formula (I), L 1 represents a group represented by formula (ph1-1), formula (ph1-2), formula (ph11-1), or formula (ph11-2); A represents a group represented by formula (ia). [ka] [In formula (ph1-1), formula (ph1-2), formula (ph11-1), and formula (ph11-2), X 1a , X 1b , X 10 , X 11a , X 11b each independently represents a substituent or a hydrocarbon group which may have a substituent. n1 represents an integer of 0 to 5, and n2 represents an integer of 0 to 4. When n1 represents an integer of 2 or more, a plurality of X 1amay be the same or different, and when n2 represents an integer of 2 or more, a plurality of X 1b may be the same or different. n1 represents an integer of 2 or more, and X 1a is bonded to adjacent carbon atoms, X is bonded to adjacent carbon atoms 1a may be bonded to each other to form a ring, n2 represents an integer of 2 or more, and X 1b is bonded to adjacent carbon atoms, X is bonded to adjacent carbon atoms 1b may be bonded to each other to form a ring. p represents an integer of 0 to 4. When p represents an integer of 2 or more, a plurality of X 10 may be the same or different. p represents an integer of 2 or more, and X 10 is bonded to adjacent carbon atoms, X is bonded to adjacent carbon atoms 10 may be bonded to each other to form a ring. q1 represents an integer of 0 to 5, and q2 represents an integer of 0 to 4. When q1 represents an integer of 2 or more, a plurality of X 11a may be the same or different, and when q2 represents an integer of 2 or more, a plurality of X 11b may be the same or different. q1 represents an integer of 2 or more, and X 11a is bonded to adjacent carbon atoms, X is bonded to adjacent carbon atoms 11a may be bonded to each other to form a ring, q2 represents an integer of 2 or more, and X 11b is bonded to adjacent carbon atoms, X is bonded to adjacent carbon atoms 11b may be bonded to each other to form a ring. Y represents -O-, -CO-, -SO2-, or -C(CF3)2-. * represents a bond to A. ** represents a bond to the group represented by formula (ib). [ka] [In formula (ia) and formula (ib), X 6 ~X 9each independently represents a hydrocarbon group which may have a substituent, and -CH- contained in the hydrocarbon group may be replaced by -O-, -CO-, or -NH-, -CH= contained in the hydrocarbon group may be replaced by -N=, and -C< contained in the hydrocarbon group may be replaced by -N<. X 6 and X 7 may be bonded to each other to form a ring, X 8 and X 9 may be bonded to each other to form a ring. * is L 1 Represents a bond with . [2] The group represented by the formula (ph1-2) is a group represented by the formula (ph2-2), The group represented by the formula (ph11-1) is a group represented by the formula (ph12-1), The azo dye according to [1], wherein the group represented by formula (ph11-2) is a group represented by formula (ph12-2). [ka] [In formula (ph2-2), formula (ph12-1), and formula (ph12-2), X 2b ~X 5b , X 12a ~X 15a , X 21a ~X 25a , X 12b ~X 15b , X 22b ~X 25b each independently represents a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, an amino group, an amido group, a carboxylic acid amide group, a carboxyl group, an alkoxy group having 1 to 4 carbon atoms, an alkylthio group having 1 to 4 carbon atoms, a cyano group, or a halogen atom. X 2b and X 3b , X 4b and X 5b , X 12a and X 13a , X 14a and X 15a , X 22a and X 23a , X21a and X 23a , X 21a and X 25a , X 24a and X 25a , X 12b and X 13b , X 14b and X 15b , X 22b and X 23b , X 24b and X 25b may be bonded to each other to form a ring. Y has the same meaning as above. * represents a bond to A. ** represents a bond to the group represented by formula (ib). [3] The azo dye according to [1] or [2], wherein the groups represented by formula (ia) and formula (ib) are each independently any of the groups represented by formulas (t1) to (t5). [ka] [In formulas (t1) to (t5), R 1 ~R 16 each independently represents a hydrogen atom, an optionally substituted hydrocarbon group, a heterocyclic group, a cyano group, or a halogen atom. * is L 1 It represents a bond with . [4] A colored curable resin composition comprising the azo dye according to any one of [1] to [3], a resin, a polymerizable compound, a polymerization initiator, and a solvent. [5] A color filter formed from the colored curable resin composition according to [4]. [6] A display device comprising the color filter according to [5]. [7] A solid-state imaging device comprising the color filter according to [5]. [8] A method for producing an azo dye, comprising: a contacting step of contacting azo dye (A) in a slurry state with a solvent (Z) at a temperature of 80 to 200°C; and a separation step of recovering the azo dye (A) contacted with the solvent (Z) by solid-liquid separation, wherein the solvent (Z) comprises at least one solvent selected from the group consisting of ester solvents, ether solvents, ether ester solvents, ketone solvents, nitrile solvents, alcohol solvents, amide solvents, aromatic hydrocarbon solvents, sulfoxide solvents, sulfone solvents, halogenated solvents, and amine solvents, and the amount of the solvent (Z) in the contacting step is 0.1 to 120.0 times by mass relative to the azo dye (A). Effect of the Invention

[0006] According to the present invention, it is possible to provide an azo dye and a colored curable resin composition capable of forming a color filter having improved heat resistance and light resistance. Also, according to the present invention, a new method for producing an azo dye capable of forming a color filter having improved heat resistance and light resistance is provided. [Brief description of the drawings]

[0007] [Figure 1] Fig. 1 is an X-ray diffraction spectrum of the azo dye (1) obtained in Example 1. The peaks at diffraction angles (2θ±0.2°)=25.5, 35.1, 37.8, 43.3, and 43.4° are peaks derived from aluminum oxide, which is an internal standard substance (the same applies to Figs. 2 to 14). [Diagram 2] FIG. 2 is an X-ray diffraction spectrum of the azo dye (1-1) obtained in Synthesis Example 1. [Diagram 3] FIG. 3 is an X-ray diffraction spectrum of the azo dye (2) obtained in Example 2. [Figure 4] FIG. 4 is an X-ray diffraction spectrum of the azo dye (2-1) obtained in Synthesis Example 2. [Diagram 5] FIG. 5 is an X-ray diffraction spectrum of the azo dye (3) obtained in Example 3. [Figure 6] FIG. 6 is an X-ray diffraction spectrum of the azo dye (3-1) obtained in Synthesis Example 3. [Figure 7] FIG. 7 is an X-ray diffraction spectrum of the azo dye (4) obtained in Example 4. [Figure 8] FIG. 8 is an X-ray diffraction spectrum of the azo dye (4-1) obtained in Synthesis Example 4. [Figure 9] FIG. 9 is an X-ray diffraction spectrum of the azo dye (5a) obtained in Example 5. [Figure 10] FIG. 10 is an X-ray diffraction spectrum of the azo dye (5b) obtained in Example 6. [Figure 11] FIG. 11 is an X-ray diffraction spectrum of the azo dye (5c) obtained in Example 7. [Figure 12] FIG. 12 is an X-ray diffraction spectrum of the azo dye (5d) obtained in Example 8. [Figure 13] FIG. 13 is an X-ray diffraction spectrum of the azo dye (5e) obtained in Example 9. [Figure 14] FIG. 14 is an X-ray diffraction spectrum of the azo dye (5f) obtained in Example 10. [Figure 15] FIG. 15 is an X-ray diffraction spectrum of the azo dye (5g) obtained in Example 11. [Figure 16] FIG. 16 is an X-ray diffraction spectrum of the azo dye (5h) obtained in Example 12. [Figure 17] FIG. 17 is an X-ray diffraction spectrum of the azo dye (5i) obtained in Example 13. [Figure 18] FIG. 18 is an X-ray diffraction spectrum of the azo dye (5j) obtained in Example 14. [Figure 19] FIG. 19 is an X-ray diffraction spectrum of the azo dye (5k) obtained in Example 15. [Figure 20] FIG. 20 is an X-ray diffraction spectrum of the azo dye (5l) obtained in Example 16. [Figure 21] FIG. 21 is an X-ray diffraction spectrum of the azo dye (5-1) obtained in Synthesis Example 5. [Figure 22] FIG. 22 shows the X-ray diffraction spectrum of the glass sample plate. DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS

[0008] <Azo dye> The azo dye of the present invention has a specific crystal structure. The crystal structure is identified by powder X-ray diffraction. Specifically, the azo dye of the present invention has a diffraction pattern of the following in powder X-ray diffraction using CuKα radiation of a mixture of 50 parts of the azo dye and 50 parts of aluminum oxide: There are peaks in the diffraction angle range (2θ±0.2°) = 5° to 25°, The maximum peak is at 9.8°~16.0°, and the maximum peak is at 5°~25°. At least one peak exists between 11.0° and 11.8°. Between the maximum peak intensity at 9.8°-16.0° (I1) and the maximum peak intensity at 11.0°-11.8° (I2), I2 / I1≧0.05 and Between the peak intensity (I3) at the diffraction angle (2θ±0.2°)=35.1° due to aluminum oxide and the I1, I1 / I3≧0.35 It has a crystal structure that satisfies the following: By using an azo dye having such a crystal structure, it is possible to form a color filter having good heat resistance and light resistance. In the present invention, the color filter having excellent heat resistance or light resistance is formed by reducing the color difference (ΔE * ab) is small.

[0009] In the X-ray diffraction pattern, the maximum peak at 5° to 25°, which is in the diffraction angle range (2θ±0.2°) of 9.8° to 16.0°, may be at 11.0° to 11.8°, but is preferably outside the range of 11.0° to 11.8°.

[0010] The I2 / I1 is preferably 0.07 or more, more preferably 0.09 or more, and is preferably 0.6 or less, more preferably 0.5 or less, even more preferably 0.45 or less, still more preferably 0.40 or less, and even more preferably 0.38 or less.

[0011] The I1 / I3 is preferably 0.37 or more, more preferably 0.39 or more, even more preferably 0.41 or more, still more preferably 0.43 or more, and is preferably 1.0 or less, more preferably 0.95 or less, even more preferably 0.90 or less, still more preferably 0.85 or less, even more preferably 0.80 or less, and may be 0.70 or less.

[0012] In the X-ray diffraction analysis of the present invention, CuKα radiation (1.5418 Å) from the anticathode is used as the X-ray source, and aluminum oxide is used as the internal standard substance. In the specific method of X-ray diffraction analysis, 50 parts by mass of azo dye as a sample was mixed with 50 parts by mass of aluminum oxide as an internal standard substance, and the mixture was crushed while passing through a 150-mesh wire netting. The crushed sample was then filled into a recess (inner dimensions 20 mm x 20 mm x 0.5 mm) of a glass sample plate manufactured by Rigaku Corporation, and the surface was flattened for measurement. Note that there is a peak derived from the glass sample plate (halo: Koji Obara, "What is the halo of X-ray diffraction?", NEW GLASS, 2016, Vol. 31, No. 118, pp. 24-26), which must be distinguished from the peak derived from the colorant. Therefore, in the present invention, the X-ray diffraction spectrum of the azo dye was calculated by calculating the difference spectrum between the X-ray diffraction spectrum of the glass sample plate alone and the X-ray diffraction spectrum of the colorant. Furthermore, since the thickness of the sample depends on the intensity of the X-ray diffraction spectrum, the X-ray diffraction spectrum normalized to the peak intensity I3 of aluminum oxide as the internal standard substance of 100,000 was used.

[0013] The azo dye of the present invention preferably has two or more peaks, more preferably three or more peaks, and preferably 15 or less, more preferably 10 or less, and even more preferably 7 or less, in the range of diffraction angles (2θ±0.2°) of 5° to 25° in the X-ray diffraction, the relative intensity of which is 10% or more and less than 100%, when the maximum peak intensity I1 is taken as 100%.

[0014] Examples of the azo dye of the present invention include those having peaks at the following diffraction angles (2θ±0.2°) in the above X-ray diffraction spectrum. Example (i): 10.0, 11.2, 13.1, 15.3, 15.6, 15.8, 18.5, 18.9, 19.0, 22.1, 22.5, 23.3, 25.6, 26.1, 26.4, 26.9, 28.6, 29.1° Example (ii): 7.1, 13.0, 13.3, 14.2, 17.5, 19.1, 19.4, 20.2, 21.3, 21.7, 24.1, 24.3, 27.2, 28.3, 29.4° Example (iii): 5.7, 10.6, 11.4, 14.6, 17.2, 20.3, 21.4, 24.8, 26.1, 26.5, 26.8, 28.4° Example (iv): 7.5, 11.0, 11.6, 15.0, 15.3, 19.8, 20.5, 22.2, 23.7, 24.6, 26.4, 27.7, 28.5, 30.1, 32.3° Example (v): 6.0,10.2,11.9,15.6,16.0,18.0,18.6,20.1,20.7,22.5,23.1,23.5,24.6,25.2,27.4,30.3°

[0015] The azo dye exhibiting the above-mentioned crystal structure can be obtained, for example, by the following production method.

[0016] The method for producing an azo dye of the present invention includes a contacting step of contacting an azo dye (hereinafter also referred to as azo dye (A)) in a slurry state with a solvent (Z) at a temperature of 80 to 200°C, and a separation step of extracting the azo dye (A) contacted with the solvent (Z) by solid-liquid separation, the solvent (Z) including at least one selected from the group consisting of ester solvents, ether solvents, ether ester solvents, ketone solvents, nitrile solvents, alcohol solvents, amide solvents, aromatic hydrocarbon solvents, sulfoxide solvents, sulfone solvents, halogenated solvents, and amine solvents, and the amount of the solvent (Z) in the contacting step is 0.1 to 120.0 times by mass relative to the azo dye (A). Here, the temperature does not mean the temperature of the container, but the internal temperature of the reaction system. That is, the production method of the present invention relates to a method for producing a purified azo dye (A), comprising a contacting step of contacting azo dye (A) in a slurry state with a predetermined solvent (Z) at a predetermined temperature, and a separation step of obtaining a purified azo dye (A) by solid-liquid separation such as filtration. Hereinafter, the azo dye having a predetermined crystal structure obtained by the production method of the present invention is also referred to as azo dye (Aa). The azo colorant (Aa) obtained by this production method can be used to form a color filter having good heat resistance and light resistance.

[0017] The azo dye (A) may be a single dye consisting of one kind of azo dye, or a mixed dye containing two or more kinds of azo dyes. In addition, the azo dye (A) preferably contains the azo dye (I) described below.

[0018] <Precipitation process> The production method of the present invention may include a precipitation step of recrystallizing the azo dye (A) before the contact step. Examples of the precipitation step of recrystallizing the azo dye (A) include a poor solvent addition method, and specifically, a method of adding the azo dye (A) dissolved in a high solubility liquid (good solvent, etc.) to a low solubility liquid (poor solvent, etc.) and a method of adding a low solubility liquid to an azo dye dissolved in a high solubility liquid. The azo dye (A) to be subjected to the precipitation step may be an azo dye produced by a production method for azo dye (I) described later, or the like. When the crystal structure of the azo dye (A) varies, the crystal structure can be made uniform by recrystallization. Therefore, by providing a precipitation step before the contact step, it becomes possible to obtain an azo dye (Aa) having a desired crystal structure (i.e., a desired diffraction pattern) in a higher yield and with higher selectivity.

[0019] In the precipitation step, the azo dye (A) is not brought into contact with the solvent in a slurry state at a temperature (internal temperature) of 80° C. or higher. Therefore, the azo dye (A) obtained in the precipitation step does not have a desired crystal structure (desired diffraction pattern).

[0020] Examples of the high-solubility liquid and / or low-solubility liquid used in the precipitation step include a basic compound, a basic solution, an acidic compound, and an acidic solution.

[0021] Examples of basic compounds and basic solutions include amines such as propylamine, butylamine, hexylamine, benzylamine, dimethylamine, diethylamine, dipropylamine, dihexylamine, trimethylamine, diisopropylethylamine, pyridine, and pyrrole; ammonia water; solutions of quaternary ammonium salts such as tetramethylammonium hydroxide, tetraethylammonium hydroxide, tetrapropylammonium hydroxide, tetrabutylammonium hydroxide, and benzyltrimethylammonium hydroxide (preferably, aqueous solutions); alcohol solutions of alkali metal alkoxides such as a methanol solution of sodium methoxide, an ethanol solution of sodium ethoxide, and a tert-butyl alcohol solution of potassium tert-butoxide; and solutions of alkali metal hydroxides such as sodium hydroxide and potassium hydroxide (preferably, aqueous solutions).

[0022] Examples of acidic compounds and acidic solutions include inorganic acids such as hydrochloric acid, sulfuric acid, nitric acid, phosphoric acid, boric acid, hexafluorophosphoric acid, and sulfamic acid; organic acids such as formic acid, acetic acid, trifluoroacetic acid, propionic acid, citric acid, benzenesulfonic acid, p-toluenesulfonic acid, methanesulfonic acid, trifluoromethanesulfonic acid, and salicylic acid; and solutions thereof (preferably, aqueous solutions).

[0023] The basic compound, basic solution, acidic compound, and acidic solution may be used alone or in combination of two or more.

[0024] The highly soluble liquid may be appropriately selected depending on the azo dye (A) used, but a basic compound or a basic solution is preferred. The highly soluble liquid may further contain an organic solvent in addition to the above-mentioned basic compound, basic solution, acidic compound, and acidic solution.The organic solvent may be, for example, an alcohol solvent, an ester solvent, an ether solvent, an ether ester solvent, a ketone solvent, an aromatic hydrocarbon solvent, a nitrile solvent, etc., and these organic solvents may be used alone or in combination of two or more.The organic solvent is preferably an alcohol solvent such as methanol, ethanol, isopropyl alcohol, or a nitrile solvent such as acetonitrile, and more preferably an alcohol solvent.

[0025] The amount of the highly soluble liquid used may be an amount necessary to dissolve the azo dye (A), and may be appropriately determined depending on the type and concentration of the highly soluble liquid. For example, when a solution of a quaternary ammonium salt is used as the highly soluble liquid, the amount of the quaternary ammonium salt is preferably 0.1 to 20 molar equivalents relative to the azo dye (A) (1 mole), more preferably 0.5 molar equivalents or more, even more preferably 1 molar equivalents or more, more preferably 15 molar equivalents or less, and even more preferably 10 molar equivalents or less. For example, when an inorganic acid or an organic acid, or a solution thereof, is used as the highly soluble liquid, the amount of the inorganic acid or organic acid is preferably 10 to 500 molar equivalents relative to the azo dye (A) (1 mole), more preferably 20 molar equivalents or more, even more preferably 30 molar equivalents or more, more preferably 450 molar equivalents or less, and even more preferably 400 molar equivalents or less.

[0026] The mixing time, mixing temperature, stirring conditions, etc. of the azo dye (A) and the highly soluble liquid may be set to those necessary for dissolving the azo dye (A). However, the highly soluble liquid is a liquid that easily dissolves the azo dye (A), and it is not necessary to use a high temperature to dissolve the azo dye (A). For this reason, the mixing temperature (internal temperature) is less than 80°C, preferably 60°C or less, more preferably 40°C or less, and preferably 5°C or more.

[0027] The low-solubility liquid may be appropriately selected depending on the types of azo dye (A) and high-solubility liquid used. For example, when a basic compound or a basic solution is used as the high-solubility liquid, an acidic compound or an acidic solution is preferred. The low-solubility liquid may further contain an organic solvent in addition to the above-mentioned basic compound, basic solution, acidic compound, and acidic solution.The organic solvent may be, for example, an alcohol solvent, an ester solvent, an ether solvent, an ether ester solvent, a ketone solvent, an aromatic hydrocarbon solvent, a nitrile solvent, etc., and these organic solvents may be used alone or in combination of two or more.The organic solvent is preferably an alcohol solvent such as methanol, ethanol, isopropyl alcohol, or a nitrile solvent such as acetonitrile, and more preferably an alcohol solvent. Furthermore, for example, when an acidic compound or an acidic solution is used as the highly soluble liquid, it is preferable to use, as the low-solubility liquid, an organic solvent such as an alcohol solvent, an ester solvent, an ether solvent, an ether ester solvent, a ketone solvent, an aromatic hydrocarbon solvent, or a nitrile solvent, and more preferably an alcohol solvent such as methanol, ethanol, or isopropyl alcohol, or a nitrile solvent such as acetonitrile, and these may be used alone or in combination of two or more kinds.

[0028] The amount of the low-solubility liquid used may be an amount necessary for precipitating the azo dye (A), and may be appropriately determined depending on the types and concentrations of the high-solubility liquid and the low-solubility liquid.

[0029] The mixing time, mixing temperature, stirring conditions, etc. of the mixed liquid of the azo dye (A) and the high-solubility liquid and the low-solubility liquid may be set to the conditions necessary for precipitating the azo dye (A). The mixing temperature is preferably 60° C. or less, more preferably 40° C. or less, and even more preferably 20° C. or less, from the viewpoint of efficient precipitation, and may be performed under ice cooling.

[0030] The method of adding the low-solubility liquid to the mixed liquid of the azo dye (A) and the high-solubility liquid, or adding the mixed liquid of the azo dye (A) and the high-solubility liquid to the low-solubility liquid may be a lump-sum addition, but it is preferable to add it in several portions or continuously dropwise. Even when adding it in several portions, it is preferable to add it in a continuous dropwise manner.

[0031] The azo dye (A) precipitated in the precipitation step may be extracted using a known solid-liquid separation method such as filtration or centrifugation, and may be washed with water or a solvent as necessary before being subjected to the contact step. Examples of the solvent used for washing include a solvent described below as solvent (Z). Furthermore, the azo dye (A) after washing may be subjected to a drying treatment such as vacuum drying or hot air drying as necessary.

[0032] <Contact process> The azo dye (A) is contacted with the solvent (Z) in a slurry state at a temperature (internal temperature) of 80 to 200° C. The slurry state means a state in which azo dye (A) in a mixture of the azo dye (A) and the solvent (Z) contains solid azo dye (A) that is not dissolved in the solvent (Z), and a part of the azo dye (A) may be dissolved in the solvent (Z). By contacting the azo dye (A) with the solvent (Z) at 80 to 200° C. in a slurry state, it is possible to obtain an azo dye (Aa) having a desired crystal structure (i.e., having a desired diffraction pattern).

[0033] <Solvent (Z)> The solvent (Z) used in the contact step is at least one selected from the group consisting of ester solvents (solvents containing -COO- in the molecule and not containing -O-), ether solvents (solvents containing -O- in the molecule and not containing -COO-), ether ester solvents (solvents containing -COO- and -O- in the molecule), ketone solvents (solvents containing -CO- in the molecule and not containing -COO-), alcohol solvents (solvents containing -OH in the molecule and not containing -O-, -CO-, and -COO-), aromatic hydrocarbon solvents (solvents containing aromatic hydrocarbon groups in the molecule and not containing -O-, -OH, and halogen atoms), amide solvents, sulfoxide solvents, sulfone solvents, halogen solvents (solvents containing halogen atoms in the molecule and not containing -OH), amine solvents (solvents containing -N< in the molecule and not containing -OH), and nitrile solvents. The solvent (Z) may be a single solvent consisting of one solvent or a solvent mixture containing two or more solvents.

[0034] Examples of ester solvents include methyl lactate, ethyl lactate, butyl lactate, methyl 2-hydroxyisobutanoate, ethyl acetate, n-butyl acetate, isobutyl acetate, pentyl formate, isopentyl acetate, butyl propionate, isopropyl butyrate, ethyl butyrate, butyl butyrate, methyl pyruvate, ethyl pyruvate, propyl pyruvate, methyl acetoacetate, ethyl acetoacetate, cyclohexanol acetate, and γ-butyrolactone.

[0035] Examples of the ether solvent include ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, ethylene glycol monopropyl ether, ethylene glycol monobutyl ether, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, diethylene glycol monobutyl ether, propylene glycol monomethyl ether, propylene glycol monoethyl ether, propylene glycol monopropyl ether, propylene glycol monobutyl ether, 3-methoxy-1-butanol, 3-methoxy-3-methylbutanol, tetrahydrofuran, tetrahydropyran, 1,4-dioxane, diethylene glycol dimethyl ether, diethylene glycol diethyl ether, diethylene glycol methyl ethyl ether, diethylene glycol dipropyl ether, diethylene glycol dibutyl ether, anisole, phenetole, and methylanisole.

[0036] The ether ester solvents include methyl methoxyacetate, ethyl methoxyacetate, butyl methoxyacetate, methyl ethoxyacetate, ethyl ethoxyacetate, methyl 3-methoxypropionate, ethyl 3-methoxypropionate, methyl 3-ethoxypropionate, ethyl 3-ethoxypropionate, methyl 2-methoxypropionate, ethyl 2-methoxypropionate, propyl 2-methoxypropionate, methyl 2-ethoxypropionate, ethyl 2-ethoxypropionate, methyl 2-methoxy-2-methyl ... Examples of the alkyl ether acetates include ethyl methoxy-2-methylpropionate, 3-methoxybutyl acetate, 3-methyl-3-methoxybutyl acetate, propylene glycol monomethyl ether acetate, propylene glycol monoethyl ether acetate, propylene glycol monopropyl ether acetate, ethylene glycol monomethyl ether acetate, ethylene glycol monoethyl ether acetate, diethylene glycol monoethyl ether acetate, and diethylene glycol monobutyl ether acetate.

[0037] Ketone solvents include 4-hydroxy-4-methyl-2-pentanone (diacetone alcohol), acetone, 2-butanone, 2-heptanone, 3-heptanone, 4-heptanone, 4-methyl-2-pentanone, cyclopentanone, cyclohexanone, and isophorone. The ketone solvent is preferably cyclopentanone or cyclohexanone, and more preferably cyclohexanone.

[0038] Examples of alcohol solvents include methanol, ethanol, propanol, butanol, hexanol, cyclohexanol, 2-aminoethanol, benzyl alcohol, 1-phenyl-1-propanol, 2-chlorophenol, 1-amino-2-propanol, 3-amino-1-propanol, ethylene glycol, propylene glycol, and glycerin. As the alcohol solvent, methanol and 2-aminoethanol are preferred, and 2-aminoethanol is more preferred.

[0039] Aromatic hydrocarbon solvents include benzene, toluene, xylene, mesitylene, nitrobenzene, and anisole. As the aromatic hydrocarbon solvent, toluene and xylene are preferable, and xylene is more preferable.

[0040] Examples of the amide solvent include formamide, N-methylformamide, N,N-dimethylformamide, acetamide, N,N-dimethylacetamide, N,N-dimethylisobutyramide, N,N-diethylformamide, N,N-diethylacetamide, N,N-dimethylacetoacetamide, N-methylpyrrolidone, N-methyl-ε-caprolactam, 1,3-dimethyl-2-imidazolidinone, and 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone. The amide solvent is preferably N,N-dimethylacetamide, N-methylpyrrolidone, N,N-dimethylacetoacetamide, or 1,3-dimethyl-2-imidazolidinone, and more preferably N,N-dimethylacetamide or N-methylpyrrolidone.

[0041] Sulfoxide solvents include dimethyl sulfoxide, diethyl sulfoxide, dipropyl sulfoxide, and tetramethylene sulfoxide. As the sulfoxide solvent, preferred are dimethyl sulfoxide and diethyl sulfoxide, and more preferred is dimethyl sulfoxide.

[0042] Sulfone solvents include dimethyl sulfone, diethyl sulfone, dipropyl sulfone, isopropyl methyl sulfone, and sulfolane. As the sulfone solvent, dimethyl sulfone, diethyl sulfone, and sulfolane are preferred, and sulfolane is more preferred.

[0043] Halogenated solvents include chlorobenzene, dichlorobenzene, chloroform, dichloromethane, and carbon tetrachloride.

[0044] Amine solvents include propylamine, butylamine, hexylamine, benzylamine, dimethylamine, diethylamine, dipropylamine, dihexylamine, trimethylamine, diisopropylethylamine, 1-methylimidazole, pyridine, and pyrrole.

[0045] Nitrile solvents include acetonitrile, propionitrile, and methacrylonitrile. The nitrile solvent is preferably acetonitrile.

[0046] The solvent (Z) preferably contains at least one selected from the group consisting of ester solvents, ketone solvents, alcohol solvents, amide solvents, aromatic hydrocarbon solvents, sulfoxide solvents, sulfone solvents, halogenated solvents, and amine solvents, more preferably contains at least one selected from the group consisting of ester solvents, ketone solvents, alcohol solvents, amide solvents, aromatic hydrocarbon solvents, sulfoxide solvents, sulfone solvents, and amine solvents, even more preferably contains at least one selected from the group consisting of alcohol solvents, amide solvents, aromatic hydrocarbon solvents, sulfoxide solvents, and amine solvents, even more preferably contains at least one selected from the group consisting of alcohol solvents, amide solvents, aromatic hydrocarbon solvents, and amine solvents, still more preferably contains at least one selected from the group consisting of alcohol solvents, amide solvents, aromatic hydrocarbon solvents, and amine solvents, and even more preferably contains at least one selected from the group consisting of alcohol solvents, amide solvents, aromatic hydrocarbon solvents, and amine solvents. In 100% of the solvent (Z), the total of the alcohol solvent, the amide solvent, the aromatic hydrocarbon solvent, the sulfoxide solvent, the sulfone solvent, and the amine solvent is preferably 40% or more, more preferably 50% or more, and even more preferably 60% or more, in terms of volume ratio. In addition, in 100% of the solvent (Z), the total of the alcohol solvent, the amide solvent, and the aromatic hydrocarbon solvent is preferably 40% or more, more preferably 50% or more, and even more preferably 60% or more, in terms of volume ratio.

[0047] A method of mixing the azo dye (A) and the solvent (Z) in a container is preferred as a method for contacting the azo dye (A) and the solvent (Z) at a temperature of 80 to 200° C. When mixing, the mixture containing the azo dye (A) and the solvent (Z) may be stirred with a stirrer or the like, or may be stirred by ultrasonic vibration. The contact time (preferably the stirring time) in the contact step is preferably 1 minute or more, more preferably 10 minutes or more, even more preferably 1 hour or more, and is preferably 24 hours or less, more preferably 12 hours or less, even more preferably 5 hours or less.

[0048] The contact temperature in the contact step is 80 to 200° C., and the upper limit of the temperature is preferably equal to or lower than the boiling point of the solvent (Z) at 1 atm. The contact temperature is preferably 80 to 190° C., more preferably 85 to 170° C., and even more preferably 85 to 150° C.

[0049] The amount of the solvent (Z) used in the contact step may be appropriately determined depending on the type of the azo dye (A) and the solvent (Z) used so that the mixture becomes a slurry, but from the viewpoint of yield, the amount is 0.1 times by mass or more, preferably 0.5 times by mass or more, more preferably 2 times by mass or more, and 120.0 times by mass or less, preferably 100.0 times by mass or less, more preferably 80.0 times by mass or less, and even more preferably 60.0 times by mass or less, relative to the azo dye (A). As the azo dye (A) to be subjected to the contact step, not only the dried product but also the residue containing the azo dye (A) separated from the reaction mixture in solid-liquid separation is preferably used. In the latter case, the residue may contain the solvent used in the reaction or the solvent used for washing, but the amount of the solvent (Z) used in the contact step is calculated including the solvent used in the reaction or washing contained in the residue. In addition, in the case where the solid-liquid separation is not performed and drying is not performed after the precipitation step, the precipitate may contain the solvent used for precipitation or the solvent used for washing. The amount of the solvent (Z) used in the contact step is calculated including the amount of the solvent used for precipitation or washing contained in the precipitate.

[0050] In the contacting step, the azo dye (A) is contacted with the solvent (Z) so that, in a powder X-ray diffraction pattern of a mixture of the azo dye (A) and 50 parts of α-alumina using CuKα radiation, the ratio (I1 / I3) of the maximum peak intensity (I1) at a diffraction angle (2θ±0.2°) of 5° to 25° attributable to the azo dye (A) to the peak intensity (I3) at a diffraction angle (2θ±0.2°) of 35.1° attributable to the α-alumina is reduced by changing I1 / I3 before contact with the solvent (Z) to I R1 After contact with the solvent (Z), I1 / I3 is expressed as I R2 Then, I R1 and I R2 Between I R2 / IR1 ≧1.4 It is preferable to carry out the above process so as to satisfy the following: As a specific method for the X-ray diffraction analysis, the same method as the above-mentioned X-ray diffraction analysis method is used.

[0051] Above I R2 / I R1 is preferably 1.45 or more, more preferably 1.5 or more, even more preferably 1.55 or more, still more preferably 1.6 or more, and is preferably 20 or less, more preferably 18 or less, even more preferably 15 or less, and still more preferably 12 or less.

[0052] The method may further include a step of contacting the azo dye (A) with the solvent (Z) in a slurry state at a temperature of 80 to 200° C., and then adding and mixing the mixture with a solvent (Z2) at a temperature of less than 80° C. By including a step of adding and mixing the solvent (Z2) with the mixture obtained in the contacting step at a temperature of less than 80° C., it becomes possible to obtain an azo dye (Aa) having a desired crystal structure (i.e., a desired diffraction pattern) in a higher yield.

[0053] Examples of the solvent (Z2) include the solvents exemplified as the solvent (Z) used in the contact step. The solvent (Z2) is preferably at least one selected from the group consisting of nitrile solvents and alcohol solvents, and more preferably at least one selected from the group consisting of nitrile solvents and alcohol solvents not having an amine structure. The nitrile solvent is preferably acetonitrile, and the alcohol solvent is preferably a primary alcohol such as methanol, ethanol, propanol, butanol, hexanol, or cyclohexanol.

[0054] The method of adding the solvent (Z2) to the mixture of the azo dye (A) and the solvent (Z) may be to add it all at once, but it is preferable to add it in several divided portions or to add it dropwise continuously. Even when adding it in several divided portions, it is preferable to add it dropwise continuously. During and / or after adding the solvent (Z2), it is preferable to stir the mixture with a stirrer, ultrasonic vibration, or the like. The total stirring time during and after the addition of the solvent (Z2) is preferably 1 minute or more, more preferably 5 minutes or more, even more preferably 10 minutes or more, and is preferably 20 hours or less, more preferably 10 hours or less, even more preferably 3 hours or less.

[0055] The temperature (internal temperature) when adding and stirring the solvent (Z2) is less than 80° C., preferably 75° C. or less, more preferably 70° C. or less, even more preferably 65° C. or less, even more preferably 60° C. or less, and preferably 0° C. or more, more preferably 5° C. or more. When the solvent (Z2) is added in multiple portions, the temperatures for each addition may be different.

[0056] The amount of the solvent (Z2) used may be appropriately determined depending on the types and amounts of the azo dye (A) and the solvent (Z) used, and the type of the solvent (Z2); from the viewpoint of yield, the amount of the solvent (Z2) used is preferably 0.1 times by mass or more, more preferably 0.5 times by mass or more, even more preferably 2 times by mass or more, and is preferably 80.0 times by mass or less, more preferably 60.0 times by mass or less, even more preferably 50.0 times by mass or less, and still more preferably 40.0 times by mass or less, relative to the amount of the azo dye (A).

[0057] <Separation process> The azo dye (A) that has been brought into contact with the solvent (Z) is separated from the solvent (Z) (or from the solvent (Z) and the solvent (Z2) when the solvent (Z2) is added) by solid-liquid separation, and is taken out as a solid. That is, a purified azo dye (A) can be taken out by solid-liquid separation. The purified azo dye (A) preferably has the above-mentioned predetermined crystal structure.

[0058] The solid-liquid separation is preferably carried out by natural filtration, reduced pressure filtration, pressure filtration, centrifugal filtration, centrifugation, etc. The azo dye (A) from which the solvent (Z) has been removed by solid-liquid separation may be further subjected to treatments such as washing, recrystallization, drying, etc.

[0059] As the azo dye (Aa) exhibiting the above-mentioned predetermined crystal structure, it is particularly preferable to select one exhibiting the predetermined crystal structure from compounds represented by the following formula (I) (hereinafter also referred to as azo dye (I)). The azo dye (I) exhibiting the predetermined crystal structure and having a predetermined chemical structure (hereinafter also referred to as azo dye (Ia)) makes it possible to form a color filter having improved heat resistance and light resistance.

[0060] [ka] [In formula (I), L 1 represents a group represented by formula (ph1-1), formula (ph1-2), formula (ph11-1), or formula (ph11-2); A represents a group represented by formula (ia).

[0061] [ka] [In formula (ph1-1), formula (ph1-2), formula (ph11-1), and formula (ph11-2), X 1a , X 1b , X 10 , X 11a , X 11b each independently represents a substituent or a hydrocarbon group which may have a substituent. n1 represents an integer of 0 to 5, and n2 represents an integer of 0 to 4. When n1 represents an integer of 2 or more, a plurality of X 1a may be the same or different, and when n2 represents an integer of 2 or more, a plurality of X 1b may be the same or different. n1 represents an integer of 2 or more, and X 1ais bonded to adjacent carbon atoms, X is bonded to adjacent carbon atoms 1a may be bonded to each other to form a ring, n2 represents an integer of 2 or more, and X 1b is bonded to adjacent carbon atoms, X is bonded to adjacent carbon atoms 1b may be bonded to each other to form a ring. p represents an integer of 0 to 4. When p represents an integer of 2 or more, a plurality of X 10 may be the same or different. p represents an integer of 2 or more, and X 10 is bonded to adjacent carbon atoms, X is bonded to adjacent carbon atoms 10 may be bonded to each other to form a ring. q1 represents an integer of 0 to 5, and q2 represents an integer of 0 to 4. When q1 represents an integer of 2 or more, a plurality of X 11a may be the same or different, and when q2 represents an integer of 2 or more, a plurality of X 11b may be the same or different. q1 represents an integer of 2 or more, and X 11a is bonded to adjacent carbon atoms, X is bonded to adjacent carbon atoms 11a may be bonded to each other to form a ring, q2 represents an integer of 2 or more, and X 11b is bonded to adjacent carbon atoms, X is bonded to adjacent carbon atoms 11b may be bonded to each other to form a ring. Y represents -O-, -CO-, -SO2-, or -C(CF3)2-. * represents a bond to A. ** represents a bond to the group represented by formula (ib).

[0062] [ka] [In formula (ia) and formula (ib), X 6 ~X 9each independently represents a hydrocarbon group which may have a substituent, and -CH- contained in the hydrocarbon group may be replaced by -O-, -CO-, or -NH-, -CH= contained in the hydrocarbon group may be replaced by -N=, and -C< contained in the hydrocarbon group may be replaced by -N<. X 6 and X 7 may be bonded to each other to form a ring, X 8 and X 9 may be bonded to each other to form a ring. * is L 1 It represents a bond with .

[0063] The azo dye (I) will be described in detail below, but the azo dye (I) also includes the resonance structure of formula (I), the tautomer of formula (I), and stereoisomers such as geometric isomers of formula (I). Examples of the tautomer of formula (I) include a compound in which A in formula (I) is a group represented by formula (iia); a compound in which, when formula (I) has a group represented by formula (ib) (hereinafter also referred to as group (ib)), the group (ib) in formula (I) is a group represented by formula (iib); and a compound in which, when formula (I) has group (ib), A in formula (I) is a group represented by formula (iia) and the group (ib) in formula (I) is a group represented by formula (iib).

[0064] [ka] [In formula (iia) and formula (iib), X 6 ~X 9 is the same as above, and * is L 1 It represents a bond with .

[0065] In the formulas (ph1-1), (ph1-2), (ph11-1), and (ph11-2), X 1a , X 1b , X 10 , X 11a , X 11bExamples of the substituent represented by the formula (hereinafter also referred to as substituent A) include an amino group, an amide group, a carboxylic acid amide group, a carboxyl group, an alkoxy group having 1 to 10 carbon atoms, an alkylthio group having 1 to 10 carbon atoms, a cyano group, and a halogen atom.

[0066] X 1a , X 1b , X 10 , X 11a , X 11b The hydrocarbon group represented by the formula (I) may be an aliphatic hydrocarbon group or an aromatic hydrocarbon group, and the aliphatic hydrocarbon group may be saturated or unsaturated, and may be linear or cyclic (alicyclic hydrocarbon group). The alicyclic hydrocarbon group may be monocyclic or polycyclic.

[0067] Examples of saturated chain hydrocarbon groups (hereinafter also referred to as alkyl groups) include linear alkyl groups such as methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, and decyl groups; and branched alkyl groups such as isopropyl, isobutyl, sec-butyl, tert-butyl, 1,3-dimethylbutyl, 2-ethylbutyl, and 2-ethylhexyl groups.

[0068] Examples of the unsaturated chain hydrocarbon group include alkenyl groups such as ethenyl, propenyl (e.g., 1-propenyl, 2-propenyl), and butenyl (e.g., 1-butenyl, 3-butenyl) groups; and alkynyl groups such as ethynyl, propynyl (e.g., 1-propynyl, 2-propynyl), and butynyl (e.g., 1-butynyl, 3-butynyl) groups.

[0069] The saturated or unsaturated chain hydrocarbon group preferably has 1-10 carbon atoms, more preferably 1-6 carbon atoms, and further preferably 1-4 carbon atoms.

[0070] Examples of the saturated alicyclic hydrocarbon group include cycloalkyl groups such as a cyclopropyl group, a 1-methylcyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, and a 2-methylcyclohexyl group.

[0071] Examples of the unsaturated alicyclic hydrocarbon group include cycloalkenyl groups such as a cyclohexenyl group (for example, a cyclohex-1-en-1-yl group, a cyclohex-2-en-1-yl group, a cyclohex-3-en-1-yl group), a cycloheptenyl group, and a cyclooctenyl group.

[0072] Examples of the alicyclic hydrocarbon group include polycyclic saturated alicyclic hydrocarbon groups such as a norbornyl group, an adamantyl group, and a bicyclo[2.2.2]octyl group; and polycyclic unsaturated alicyclic hydrocarbon groups such as a norbornenyl group.

[0073] The alicyclic hydrocarbon group preferably has 3 to 12 carbon atoms, more preferably 3 to 10 carbon atoms, and further preferably 3 to 8 carbon atoms.

[0074] Examples of the aromatic hydrocarbon group include a phenyl group, an o-tolyl group, an m-tolyl group, a p-tolyl group, a 2,4-dimethylphenyl group, a 2,6-dimethylphenyl group, a 2,4,6-trimethylphenyl group, a 2,4-diisopropylphenyl group, a 2,6-diisopropylphenyl group, a 4-vinylphenyl group, an o-tert-butylphenyl group, an m-tert-butylphenyl group, a p-tert-butylphenyl group, a 3,5-di(tert-butyl)phenyl group, a 1-naphthyl group, a 2-naphthyl group, and a group in which one hydrogen atom has been removed from tetralin.

[0075] The aromatic hydrocarbon group preferably has 6 to 18 carbon atoms, more preferably 6 to 12 carbon atoms, and further preferably 6 to 10 carbon atoms.

[0076] X 1a , X 1b , X 10 , X 11a , X 11bThe hydrocarbon group represented by the formula (I) may be a group obtained by combining the above-mentioned hydrocarbon groups, and examples thereof include an aralkyl group or an alkyl group having an alicyclic hydrocarbon group bonded thereto; an aromatic hydrocarbon group having a condensed cycloalkyl group; an alkyl group having an aromatic hydrocarbon group having a condensed cycloalkyl group bonded thereto; and the like.

[0077] Examples of the aralkyl group include a benzyl group, a (4-methylphenyl)methyl group, and a phenethyl group. The number of carbon atoms in the aralkyl group is preferably 7 to 18, more preferably 7 to 12, and further preferably 7 to 10.

[0078] Examples of the alkyl group having an alicyclic hydrocarbon group bonded thereto include a cyclopropylmethyl group, a cyclopropylethyl group, a cyclobutylmethyl group, a cyclohexylmethyl group, a cyclohexylethyl group, an adamantylmethyl group, etc. The number of carbon atoms in the alkyl group having an alicyclic hydrocarbon group bonded thereto is preferably 4 to 20, more preferably 4 to 15, and further preferably 4 to 10.

[0079] Examples of aromatic hydrocarbon groups condensed with a cycloalkyl group include a group in which one hydrogen atom has been removed from the benzene ring of indane, a group in which one hydrogen atom has been removed from the benzene ring of 1-methyl-indane, and a group in which one hydrogen atom has been removed from 2-methyl-indane.

[0080] Examples of the alkyl group having an aromatic hydrocarbon group condensed with a cycloalkyl group include an indane group having an alkyl group having 1 to 4 carbon atoms bonded to the benzene ring, a 1-methyl-indane group having an alkyl group having 1 to 4 carbon atoms bonded to the benzene ring, and a 2-methyl-indane group having an alkyl group having 1 to 4 carbon atoms bonded to the benzene ring.

[0081] X 1a , X 1b , X 10 , X 11a , X 11bExamples of the substituent that the hydrocarbon group represented by the formula (I) may have (hereinafter also referred to as the substituent B) include an amino group, an amide group, a carboxylic acid amide group, a carboxyl group, an alkoxy group having 1 to 10 carbon atoms, an alkylthio group having 1 to 10 carbon atoms, a cyano group, a halogen atom, and a hydroxy group.

[0082] The amino group as the substituent A and the substituent B may be an unsubstituted amino group or a substituted amino group. The substituted amino group is preferably an amino group having one or two hydrocarbon groups. As the hydrocarbon group, the above-mentioned X 1a , X 1b , X 10 , X 11a , X 11b Examples of the substituted amino group include the same groups as the hydrocarbon group represented by the following formula: and it is preferably an alkyl group. The number of carbon atoms in the hydrocarbon group is preferably 1 to 10, more preferably 1 to 4. Examples of the substituted amino group include an N-methylamino group, an N,N-dimethylamino group, an N-ethylamino group, an N,N-diethylamino group, an N-propylamino group, an N,N-dipropylamino group, an N-isopropylamino group, an N,N-diisopropylamino group, an N-phenylamino group, an N,N-diphenylamino group, and an N,N-ethylmethylamino group.

[0083] The amide group as the substituent A and the substituent B is *-CONR X1 R X2 (R X1 , R X2 each independently represents a hydrogen atom or a hydrocarbon group which may have a substituent, and * represents a bond. X1 , R X2 The hydrocarbon group represented by the above formula is 1a , X 1b , X 10 , X 11a , X 11b The hydrocarbon group preferably contains an aromatic hydrocarbon group. The number of carbon atoms in the hydrocarbon group is preferably 6 to 15, and more preferably 6 to 12. X1 , R X2Examples of the substituent that the hydrocarbon group represented by the formula (I) may have include the same groups as the substituent B. X1 , R X2 is preferably a hydrocarbon group having 6 to 15 carbon atoms and the other a hydrogen atom or a hydrocarbon group having 1 to 4 carbon atoms, and more preferably one an aromatic hydrocarbon group or aralkyl group having 6 to 15 carbon atoms and the other a hydrogen atom or a saturated chain hydrocarbon group having 1 to 4 carbon atoms. Examples of the amide group include amide groups represented by the following formulas (am1) to (am9).

[0084] [ka]

[0085] The carboxylic acid amide group as the substituent A and the substituent B means a group in which one hydrogen atom bonded to a nitrogen atom has been removed from an amide, and examples thereof include a formamide group, an acetamide group, a propylamide group, a butylamide group, a benzamide group, a trifluoroacetamide group, a pentafluorobenzamide group, etc. The number of carbon atoms in the amide group is preferably 2 to 20, more preferably 2 to 10, and further preferably 2 to 6.

[0086] Examples of the alkoxy group as the substituent A and the substituent B include a methoxy group, an ethoxy group, a propoxy group, an n-butoxy group, a tert-butoxy group, etc. The number of carbon atoms in the alkoxy group is preferably 1 to 8, more preferably 1 to 5, even more preferably 1 to 4, and even more preferably 1 or 2.

[0087] Examples of the alkylthio group as the substituent A and the substituent B include a methylthio group, an ethylthio group, a propylthio group, and an n-butylthio group. The alkylthio group has preferably 1 to 8 carbon atoms, more preferably 1 to 5, further preferably 1 to 4, and further preferably 1 or 2.

[0088] Examples of the halogen atom as the substituent A and the substituent B include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom. Among these, a fluorine atom, a chlorine atom, or a bromine atom is preferable, and a chlorine atom is more preferable.

[0089] X 1a , X 11a are each independently preferably a hydrocarbon group having 1 to 20 carbon atoms, an amino group, an amide group, a carboxylic acid amide group, a carboxyl group, an alkoxy group having 1 to 10 carbon atoms, a cyano group, a halogen atom, or a hydroxy group, more preferably an alkyl group having 1 to 10 carbon atoms, a hydrocarbon group containing an aromatic hydrocarbon group having 6 to 20 carbon atoms, an amino group, an amide group, a carboxylic acid amide group, an alkoxy group having 1 to 8 carbon atoms, a cyano group, a halogen atom, or a hydroxy group, still more preferably an alkyl group having 1 to 4 carbon atoms, an aromatic hydrocarbon group or aralkyl group having 6 to 12 carbon atoms, an amide group, a carboxylic acid amide group, an alkoxy group having 1 to 4 carbon atoms, a halogen atom, or a hydroxy group, and further preferably an alkyl group having 1 to 4 carbon atoms, an aralkyl group having 6 to 12 carbon atoms, X1 R X2 , a carboxylic acid amide group having 2 to 20 carbon atoms, an alkoxy group having 1 to 4 carbon atoms, or a halogen atom, and even more preferably an alkyl group having 1 to 4 carbon atoms, an amide group represented by any of the above formulas (am1) to (am9), an alkoxy group having 1 to 4 carbon atoms, or a halogen atom.

[0090] X 1b , X 10 , X 11b are each independently preferably an alkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 4 carbon atoms, a cyano group, or a halogen atom, more preferably an alkyl group having 1 to 4 carbon atoms, an alkoxy group having 1 to 4 carbon atoms, a cyano group, or a halogen atom, even more preferably an alkyl group having 1 to 4 carbon atoms, an alkoxy group having 1 to 4 carbon atoms, or a halogen atom, and even more preferably an alkyl group having 1 to 4 carbon atoms, or a halogen atom.

[0091] It is preferable that n1, n2, p, q1, and q2 each independently represent an integer of 0 to 2.

[0092] In formula (ph1-1), when n1 is an integer of 2 or more, a plurality of X 1a may be the same or different, and in formula (ph1-2), when n2 is an integer of 2 or more, a plurality of X 1b In formula (ph11-1) and formula (ph11-2), when p is an integer of 2 or more, a plurality of X 10 may be the same or different, and in formula (ph11-1), when q1 is an integer of 2 or more, a plurality of X 11a may be the same or different, and in formula (ph11-2), when q2 is an integer of 2 or more, a plurality of X 11b may be the same or different.

[0093] n1 represents an integer of 2 or more, and X 1a is bonded to adjacent carbon atoms, X is bonded to adjacent carbon atoms 1a may be bonded to each other to form a ring, n2 represents an integer of 2 or more, and X 1b is bonded to adjacent carbon atoms, X is bonded to adjacent carbon atoms 1b may be bonded to each other to form a ring. In addition, p represents an integer of 2 or more, and X 10 is bonded to adjacent carbon atoms, X is bonded to adjacent carbon atoms 10 may be bonded to each other to form a ring. In addition, q1 represents an integer of 2 or more, and X 11a is bonded to adjacent carbon atoms, X is bonded to adjacent carbon atoms 11a may be bonded to each other to form a ring, q2 represents an integer of 2 or more, and X 11b is bonded to adjacent carbon atoms, X is bonded to adjacent carbon atoms 11b may be bonded to each other to form a ring. Examples of the ring formed by the above bond include the following structure: 1It represents a bond to an adjacent carbon atom in the

[0094] [ka]

[0095] Y is -O-, -CO-, -SO2-, or -C(CF3)2-, preferably -O- or -CO-, and more preferably -CO-.

[0096] The bonding positions of A and group (ib) in formula (ph1-2) and formula (ph11-2), and the bonding position of A in formula (ph11-1) are not particularly limited, but from the viewpoint of easy availability of raw materials, formula (ph1-2) is preferably a group represented by the following formula (ph2-2), formula (ph11-1) is preferably a group represented by the following formula (ph12-1), and formula (ph11-2) is preferably a group represented by the following formula (ph12-2).

[0097] [ka] [In formula (ph2-2), formula (ph12-1), and formula (ph12-2), X 2b ~X 5b , X 12a ~X 15a , X 21a ~X 25a , X 12b ~X 15b , X 22b ~X 25b each independently represents a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, an amino group, an amido group, a carboxylic acid amide group, a carboxyl group, an alkoxy group having 1 to 4 carbon atoms, an alkylthio group having 1 to 4 carbon atoms, a cyano group, or a halogen atom. X 2b and X 3b , X 4b and X 5b , X 12a and X 13a , X 14a and X 15a , X22a and X 23a , X 21a and X 23a , X 21a and X 25a , X 24a and X 25a , X 12b and X 13b , X 14b and X 15b , X 22b and X 23b , X 24b and X 25b may be bonded to each other to form a ring. Y has the same meaning as above. * represents a bond to A. ** represents a bond to group (ib).

[0098] X 2b ~X 5b , X 12a ~X 15a , X 21a ~X 25a , X 12b ~X 15b , X 22b ~X 25b Examples of the alkyl group having 1 to 4 carbon atoms represented by the formula (1) include a methyl group, an ethyl group, a propyl group, an n-butyl group, an isobutyl group, a tert-butyl group, etc. Among these, a methyl group or an ethyl group is preferable.

[0099] X 2b ~X 5b , X 12a ~X 15a , X 21a ~X 25a , X 12b ~X 15b , X 22b ~X 25b Examples of the amino group represented by the formula (I) include the groups explained as the amino group in the substituents A and B, and the preferred ranges thereof are also the same.

[0100] X 2b ~X 5b , X 12a ~X 15a , X 21a ~X 25a , X12b ~X 15b , X 22b ~X 25b Examples of the amide group represented by the formula (I) include the groups explained as the amide group in the substituents A and B, and the preferred ranges thereof are also the same.

[0101] X 2b ~X 5b , X 12a ~X 15a , X 21a ~X 25a , X 12b ~X 15b , X 22b ~X 25b Examples of the carboxylic acid amide group represented by the formula (I) include the groups explained as the carboxylic acid amide group in the substituents A and B, and the preferred ranges thereof are also the same.

[0102] X 2b ~X 5b , X 12a ~X 15a , X 21a ~X 25a , X 12b ~X 15b , X 22b ~X 25b Examples of the alkoxy group represented by the formula (I) include the groups explained as the alkoxy group in the substituent A and the substituent B, and the preferred ranges thereof are also the same.

[0103] X 2b ~X 5b , X 12a ~X 15a , X 21a ~X 25a , X 12b ~X 15b , X 22b ~X 25b Examples of the alkylthio group represented by the formula (I) include the groups explained as the alkylthio group in the substituents A and B, and the preferred ranges thereof are also the same.

[0104] X 2b ~X 5b , X 12a ~X 15a , X 21a ~X25a , X 12b ~X 15b , X 22b ~X 25b Examples of the halogen atom represented by the formula (I) include those described as the halogen atoms in the substituents A and B, and the preferred ranges thereof are also the same.

[0105] X 2b and X 3b , X 4b and X 5b , X 12a and X 13a , X 14a and X 15a , X 22a and X 23a , X 21a and X 23a , X 21a and X 25a , X 24a and X 25a , X 12b and X 13b , X 14b and X 15b , X 22b and X 23b , or X 24b and X 25b The ring formed by bonding with each other includes the above-mentioned X 1a , X 1b , X 10 , X 11a , or X 11b Examples of the ring include those described above as a ring formed by bonding two or more of the above.

[0106] In the group represented by formula (ph1-1), n1 is preferably an integer of 0 to 2, more preferably 1 or 2, and even more preferably 2. When n1 is 2, X 1a If there are two X 1a may be bonded at any of the ortho, meta, or para positions, is preferably bonded at the meta or para position, and is more preferably bonded at the para position.

[0107] The group represented by formula (ph1-1) is X 1ais preferably a hydrocarbon group having a substituent B or a substituent A, more preferably a chain hydrocarbon group having 1 to 10 carbon atoms having a substituent B, or the substituent A, even more preferably a saturated chain hydrocarbon group having 1 to 4 carbon atoms having a substituent B, or the substituent A, even more preferably a saturated chain hydrocarbon group having 1 to 4 carbon atoms having a substituent B (preferably an amino group, an amide group, a carboxylic acid amide group, an alkoxy group having 1 to 10 carbon atoms, and / or a halogen atom), an amino group, an amide group, a carboxylic acid amide group, an alkoxy group having 1 to 10 carbon atoms, or a halogen atom, still more preferably an amino group, an amide group, a carboxylic acid amide group, an alkoxy group having 1 to 10 carbon atoms, or a halogen atom, still more preferably an amide group, a carboxylic acid amide group, an alkoxy group having 1 to 4 carbon atoms, or a halogen atom, and particularly preferably an amide group or an alkoxy group having 1 to 4 carbon atoms.

[0108] As the group represented by formula (ph1-1), for example, groups represented by the following formulae (ph1-12-1) to (ph1-12-8) are preferred, and groups represented by formulae (ph1-12-3) to (ph1-12-5) are more preferred. In the formulae, * represents a bond to A.

[0109] [ka]

[0110] The group represented by formula (ph2-2) is X 2b ~X 5b are each independently preferably a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, an alkoxy group having 1 to 4 carbon atoms, a cyano group, or a halogen atom, more preferably a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, an alkoxy group having 1 to 4 carbon atoms, or a chlorine atom, and further preferably a hydrogen atom or a chlorine atom.

[0111] As the group represented by formula (ph2-2), for example, the groups represented by the following formulae (ph2-22-1) to (ph2-22-8) are preferred, and the groups represented by formulae (ph2-22-1) to (ph2-22-7) are more preferred. In the formulae, * represents a bond to A, and ** represents a bond to group (ib).

[0112] [ka]

[0113] The group represented by formula (ph12-1) is X 12a ~X 15a are each independently preferably a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, an alkoxy group having 1 to 4 carbon atoms, a cyano group, or a halogen atom, more preferably a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, an alkoxy group having 1 to 4 carbon atoms, or a chlorine atom, and further preferably a hydrogen atom or a chlorine atom. The group represented by formula (ph12-1) is X 21a ~X 25a are each independently preferably a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, an amino group, an amide group, a carboxylic acid amide group, an alkoxy group having 1 to 4 carbon atoms, or a halogen atom, more preferably a hydrogen atom, an amino group, an amide group, a carboxylic acid amide group, an alkoxy group having 1 to 4 carbon atoms, or a halogen atom, still more preferably a hydrogen atom, an amide group, a carboxylic acid amide group, an alkoxy group having 1 to 4 carbon atoms, or a halogen atom, and still more preferably a hydrogen atom, an amide group, or an alkoxy group having 1 to 4 carbon atoms.

[0114] As the group represented by formula (ph12-1), for example, the groups represented by the following formulae (ph12-12-1) to (ph12-12-8) are preferred, and the groups represented by formulae (ph12-12-3) to (ph12-12-5) are more preferred. In the formulae, Y has the same meaning as above, and * represents a bond to A.

[0115] [ka]

[0116] The group represented by formula (ph12-2) is X 12b ~X 15b , X 22b ~X 25bare each independently preferably a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, an alkoxy group having 1 to 4 carbon atoms, a cyano group, or a halogen atom, more preferably a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, an alkoxy group having 1 to 4 carbon atoms, or a chlorine atom, and further preferably a hydrogen atom or a chlorine atom.

[0117] As the group represented by formula (ph12-2), for example, the groups represented by the following formulae (ph12-22-1) to (ph12-22-8) are preferred, and the groups represented by formulae (ph12-22-1) to (ph12-22-5) are more preferred. In the formulae, Y has the same meaning as above, * represents a bond to A, and ** represents a bond to group (ib).

[0118] [ka]

[0119] X in formula (ia) and formula (ib) 6 ~X 9 The hydrocarbon group represented by the above formula is 1a , X 1b , X 10 , X 11a , X 11b The hydrocarbon group represented by X may be any of the groups described above. 6 ~X 9 -CH2- contained in the hydrocarbon group represented by the formula (I) may be replaced by -O-, -CO-, or -NH-; 6 ~X 9 -CH= in the hydrocarbon group represented by the formula (I) may be replaced by -N=, 6 ~X 9 The -C< contained in the hydrocarbon group represented by the following formula may be replaced with -N<.

[0120] Also, X 6 and X 7 may be bonded to each other to form a ring, X 8 and X 9 may be bonded to each other to form a ring. 6 and X 7A ring formed by bonding together with X 8 and X 9 a -CH2- in the ring formed by bonding together is replaced with -O-, -CO-, or -NH-; 6 and X 7 A ring formed by bonding together with X 8 and X 9 A form in which -CH= in the ring formed by bonding together is replaced with -N=; X 6 and X 7 A ring formed by bonding together with X 8 and X 9 The present invention also includes an embodiment in which --C< in the ring formed by bonding together is replaced with --N<.

[0121] In formula (ia), X 6 and X 7 are bonded to each other to form a ring, and in formula (ib), X 8 and X 9 Examples of groups in which L are bonded to each other to form a ring include the following: 1 At least one hydrogen atom in the group represented by the following formula may be replaced by a substituent C described later.

[0122] [ka]

[0123] [ka]

[0124] X 6 ~X 9 Examples of the substituent that the hydrocarbon group represented by the formula (hereinafter also referred to as the substituent C) may have include a hydroxy group, an alkoxy group having 1 to 4 carbon atoms, an alkylthio group having 1 to 4 carbon atoms, a carboxyl group, an amino group, an amide group, a carboxylic acid amide group, a cyano group, a halogen atom, -SO3H, -SO3M, -SO3T 0.5 , -SO2N(R 17M represents an alkali metal atom, T represents an alkaline earth metal atom, and R 17 represents a hydrogen atom or a hydrocarbon group.

[0125] Examples of the alkoxy group as the substituent C include those described as the alkoxy group in the substituent A and the substituent B, and the preferred ranges thereof are also the same.

[0126] Examples of the alkylthio group as the substituent C include those described as the alkylthio group in the substituents A and B, and the preferred ranges thereof are also the same.

[0127] The amino group as the substituent C includes those described as the amino group in the substituent A and the substituent B, and the preferred ranges thereof are also the same.

[0128] The amide group as the substituent C includes those described as the amide group in the substituents A and B, and the preferred ranges thereof are also the same.

[0129] Examples of the carboxylic acid amide group as the substituent C include those described as the carboxylic acid amide group in the substituents A and B, and the preferred ranges thereof are also the same.

[0130] Examples of the halogen atom as the substituent C include those described as the halogen atoms in the substituents A and B, and a chlorine atom, a bromine atom or a fluorine atom is preferred.

[0131] The alkali metal atom represented by M includes sodium, potassium, and the like.

[0132] Examples of the alkaline earth metal atom represented by T include magnesium, calcium, barium, etc., and magnesium and calcium are preferred. 6 ~X 9 Either of the following is true: -SO3T 0.5 When it is a hydrocarbon group having one alkyl group, the azo dye (I) has the following structure:

[0133] [ka] [In the formula, L 1 , A, and T have the same meanings as above. - X 6 ~X 9

[0036] One of the hydrogen atoms of the hydrocarbon group represented by the formula:

[0134] R 17 represents a hydrogen atom or a hydrocarbon group. 17 may be the same or different, and it is preferable that one of them is a hydrogen atom and the other is a hydrocarbon group. 17 The hydrocarbon group represented by the above formula is 1a , X 1b , X 10 , X 11a , X 11b and preferably an alkyl group having 1 to 10 carbon atoms, a cycloalkyl group having 3 to 10 carbon atoms, a polycyclic saturated alicyclic hydrocarbon group having 3 to 12 carbon atoms, or an aromatic hydrocarbon group having 6 to 18 carbon atoms.

[0135] When the azo dye (I) has a group represented by formula (ib), it is preferable that the group represented by formula (ia) and the group represented by formula (ib) are the same. 6 and X 8 represent the same group, and X 7 and X 9 It is preferable that the group represented by formula (ia) and the group represented by formula (ib) are the same, whereby the color density when made into a color filter is improved.

[0136] The group represented by formula (ia) and the group represented by formula (ib) are each independently more preferably any of the groups represented by formulas (t1) to (t5), further preferably any of the groups represented by formulas (t1) to (t4), still further preferably any of the groups represented by formulas (t1) to (t3), and still further preferably any of the groups represented by formulas (t1) and (t3).

[0137] [ka] [In formulas (t1) to (t5), R 1 ~R 16 each independently represents a hydrogen atom, a hydrocarbon group which may have a substituent, a heterocyclic group, a cyano group, or a halogen atom. 1 It represents a bond with .

[0138] R 1 ~R 16 The hydrocarbon group represented by the above formula is 1a , X 1b , X 10 , X 11a , X 11b Among these, alkyl groups having 1 to 10 carbon atoms, cycloalkyl groups having 3 to 10 carbon atoms, and aromatic hydrocarbon groups having 6 to 12 carbon atoms are preferred, alkyl groups having 1 to 6 carbon atoms, and aromatic hydrocarbon groups having 6 to 12 carbon atoms are more preferred, and alkyl groups having 1 to 6 carbon atoms, and phenyl groups are even more preferred.

[0139] R 1 ~R 16 Examples of the substituent that the hydrocarbon group represented by the following formula (I) may have include the groups explained above as the substituent C, and the preferred ranges thereof are also the same.

[0140] R 1 ~R 16Examples of the heterocyclic group represented by the formula (I) include a thienyl group, a benzo[b]thienyl group, a thianthrenyl group, a furyl group, a pyranyl group, an isobenzofuranyl group, a chromenyl group, a xanthenyl group, a pyrrolyl group, an imidazolyl group, a pyrazolyl group, a pyridyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, an indolizinyl group, an indolyl group, a 1H-indazolyl group, an isoquinolyl group, a quinolyl group, a phthalazinyl group, a carbazolyl group, an acridinyl group, a chromanyl group, a pyrrolidinyl group, a piperidyl group, a piperazinyl group, an indolinyl group, an isoindolinyl group, and a benzimidazolonyl group. Among these, heterocyclic groups having a benzene ring, such as a benzo[b]thienyl group, a thianthrenyl group, an isobenzofuranyl group, a chromenyl group, a xanthenyl group, an indolyl group, a 1H-indazolyl group, an isoquinolyl group, a quinolyl group, a phthalazinyl group, a carbazolyl group, an acridinyl group, a chromanyl group, an indolinyl group, an isoindolinyl group, or a benzimidazolonyl group, are preferred, and an indolyl group, a 1H-indazolyl group, an isoquinolyl group, a quinolyl group, a phthalazinyl group, a carbazolyl group, an acridinyl group, an indolinyl group, an isoindolinyl group, or a benzimidazolonyl group is more preferred.

[0141] R 1 ~R 16 Examples of the halogen atom represented by the formula (I) include those described as the halogen atoms in the substituents A and B, and among these, a chlorine atom and a fluorine atom are preferred.

[0142] R 1 is preferably an aromatic hydrocarbon group which may have a substituent, more preferably an aromatic hydrocarbon group having 6 to 12 carbon atoms which may have a substituent, even more preferably an aromatic hydrocarbon group having 6 to 12 carbon atoms, still more preferably an aromatic hydrocarbon group having 6 to 10 carbon atoms, and even more preferably a phenyl group.

[0143] R 2is preferably a chain hydrocarbon group which may have a substituent, more preferably a chain hydrocarbon group having 1 to 10 carbon atoms which may have a substituent, even more preferably a saturated chain hydrocarbon group having 1 to 10 carbon atoms which may have a substituent, still more preferably an alkyl group having 1 to 6 carbon atoms, and even more preferably an alkyl group having 1 to 4 carbon atoms.

[0144] R 3 and R 4 are each independently preferably a hydrogen atom, an alkyl group, a cycloalkyl group, or an aromatic hydrocarbon group, and more preferably a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, a cycloalkyl group having 3 to 8 carbon atoms, or a phenyl group. 3 and R 4 are preferably the same.

[0145] R 5 is preferably a chain hydrocarbon group which may have a substituent or a hydrogen atom, more preferably a chain hydrocarbon group having 1 to 10 carbon atoms which may have a substituent, even more preferably a saturated chain hydrocarbon group having 1 to 10 carbon atoms which may have a substituent, still more preferably an alkyl group having 1 to 8 carbon atoms, and even more preferably an alkyl group having 1 to 6 carbon atoms.

[0146] R 6 is preferably an alkyl group which may have a substituent or a cyano group, more preferably an alkyl group which may have a halogen atom or a cyano group, still more preferably an alkyl group having 1 to 4 carbon atoms which may have a halogen atom or a cyano group, and still more preferably a cyano group.

[0147] R 7 is preferably a chain hydrocarbon group which may have a substituent, more preferably a chain hydrocarbon group of 1 to 10 carbon atoms which may have a substituent, even more preferably a saturated chain hydrocarbon group of 1 to 10 carbon atoms which may have a substituent, still more preferably an alkyl group of 1 to 8 carbon atoms, and even more preferably an alkyl group of 1 to 6 carbon atoms.

[0148] R 8 is preferably an alkyl group which may have a substituent, and more preferably an alkyl group having 1 to 4 carbon atoms.

[0149] R 9 is preferably an alkyl group which may have a substituent or a hydrogen atom, and more preferably an alkyl group having 1 to 4 carbon atoms or a hydrogen atom.

[0150] R 10 is preferably an aromatic hydrocarbon group or a heterocyclic group which may have a substituent, more preferably a phenyl group which may have a substituent, or a heterocyclic group having a benzene ring, and further preferably a phenyl group which may have a halogen atom, or a benzimidazolonyl group.

[0151] R 11 ~R 16 are preferably each independently an alkyl group which may have a substituent or a hydrogen atom, more preferably an alkyl group which may have a halogen atom or a hydrogen atom, and further preferably an alkyl group having 1 to 4 carbon atoms which may have a halogen atom or a hydrogen atom.

[0152] More specifically, the azo dye (I) may be, for example, azo dye (AI-1) to azo dye (AI-378) shown in Tables 1 to 5. In addition, in Tables 1 to 5, ib represents the group (ib), ph1-12-3 to ph1-12-5, ph2-22-1 to ph2-22-3, ph2-22-7, ph12-12-3 to ph12-12-5, and ph12-22-1 to ph12-22-5 represent the groups represented by the above formulas (ph1-12-3) to (ph1-12-5), (ph2-22-1) to (ph2-22-3), (ph2-22-7), (ph12-12-3) to (ph12-12-5), and (ph12-22-1) to (ph12-22-5), respectively, and t6 to t11 represent the groups represented by the following formulas (t6) to (t11).

[0153] [Table 1]

[0154] [Table 2]

[0155] [Table 3]

[0156] [Table 4]

[0157] [Table 5]

[0158] [ka] [In formula (t6) to formula (t11), * is L 1 It represents a bond with .

[0159] Among the azo dyes (I), azo dye (AI-1) to azo dye (AI-24), azo dye (AI-40) to azo dye (AI-45), azo dye (AI-76) to azo dye (AI-81), azo dye (AI-112) to azo dye (AI-117), azo dye (AI-151) to azo dye (AI-174), and azo dye (AI-274) to azo dye (AI-378) are preferred; Azo dye (AI-1) to azo dye (AI-6), azo dye (AI-19) to azo dye (AI-24), azo dye (AI-112) to azo dye (AI-117), azo dye (AI-151) to azo dye (AI-156), azo dye (AI-169) to azo dye (AI-174), azo dye (AI-274) to azo dye (AI-279), azo dye (AI-295) to azo dye (AI-300), azo dye (AI-316) to azo dye (AI-321), azo dye (AI-337) to azo dye (AI-342), and azo dye (AI-358) to azo dye (AI-363) are more preferable, More preferred are azo dye (AI-1) to azo dye (AI-6), azo dye (AI-19) to azo dye (AI-24), azo dye (AI-151) to azo dye (AI-156), azo dye (AI-169) to azo dye (AI-174), and azo dye (AI-274) to azo dye (AI-279). Azo dye (AI-1) to azo dye (AI-6), azo dye (AI-19) to azo dye (AI-24), azo dye (AI-169), azo dye (AI-172), azo dye (AI-274) to azo dye (AI-279) are even more preferred, More preferred are azo dye (AI-1), azo dye (AI-4), azo dye (AI-19), azo dye (AI-22), azo dye (AI-274), and azo dye (AI-277).

[0160] The azo dye (I) can be produced, for example, by the following method.

[0161] When the azo dye (I) is a compound represented by the following formula (I1) (hereinafter also referred to as compound (I1)), first, an amine represented by formula (pt1-1) is diazotized to produce a diazonium salt represented by formula (q1-1). The compound represented by formula (I1) can be produced by reacting the resulting diazonium salt represented by formula (q1-1) with a compound represented by formula (pt2).

[0162] [ka] [In formula (pt1-1), formula (pt2), formula (q1-1), and formula (I1), X 1a , X 6 , X 7 , and n1 have the same meaning as above. Q 1 represents an inorganic anion or an organic anion.

[0163] When the azo dye (I) is a compound represented by the following formula (I2) (hereinafter also referred to as compound (I2)), first, an amine represented by formula (pt1-2) is diazotized to produce a diazonium salt represented by formula (q1-2). The obtained diazonium salt represented by formula (q1-2) is reacted with a compound represented by formula (pt2) to produce a compound represented by formula (q2). Next, the compound represented by formula (q2) is reduced to produce an amine represented by formula (q3). Furthermore, the obtained amine is diazotized to produce a diazonium salt represented by formula (q4), and then the compound represented by formula (pt3) is reacted to produce a compound represented by formula (I2).

[0164] [ka] [In formula (pt1-2), formula (pt2), formula (pt3), formula (q1-2), formula (q2) to formula (q4), and formula (I2), X 1b , X 6 ~X 9 , and n2 have the same meaning as above. Q 1 and Q 2 each independently represents an inorganic anion or an organic anion.

[0165] In addition, when the azo dye (I) is compound (I2), it can also be produced by the following method. First, one of the amino groups of the diamine represented by formula (pt1-2A) is diazotized to produce a diazonium salt represented by formula (q1-2A). The obtained diazonium salt represented by formula (q1-2A) is reacted with a compound represented by formula (pt2) to produce an amine represented by formula (q3). Furthermore, the amine represented by formula (q3) is diazotized to produce a diazonium salt represented by formula (q4), and then the compound represented by formula (pt3) is reacted to produce a compound represented by formula (I2).

[0166] [ka] [In formula (pt1-2A), formula (pt2), formula (pt3), formula (q1-2A), formula (q3), formula (q4), and formula (I2), X 1b , X 6 ~X 9 , and n2 have the same meaning as above. Q 1 and Q 2 each independently represents an inorganic anion or an organic anion.

[0167] When the azo dye (I) is a compound represented by the following formula (I3) (hereinafter also referred to as compound (I3)), first, an amine represented by formula (pt11-1) is diazotized to produce a diazonium salt represented by formula (q11-1). The compound represented by formula (I3) can be produced by reacting the resulting diazonium salt represented by formula (q11-1) with a compound represented by formula (pt2).

[0168] [ka] [In formula (pt11-1), formula (pt2), formula (q11-1), and formula (I3), X 10 , X 11a , X 6 , X 7, Y, p, and q1 have the same meanings as above. Q 1 represents an inorganic anion or an organic anion.

[0169] When the azo dye (I) is a compound represented by the following formula (I4) (hereinafter also referred to as compound (I4)), first, an amine represented by formula (pt11-2) is diazotized to produce a diazonium salt represented by formula (q11-2). The obtained diazonium salt represented by formula (q11-2) is reacted with a compound represented by formula (pt2) to produce a compound represented by formula (q2-1). Next, the compound represented by formula (q2-1) is reduced to produce an amine represented by formula (q3-1). Furthermore, the obtained amine is diazotized to produce a diazonium salt represented by formula (q4-1), and then the compound represented by formula (pt3) is reacted to produce a compound represented by formula (I4).

[0170] [ka] [In formula (pt11-2), formula (pt2), formula (pt3), formula (q11-2), formula (q2-1) to formula (q4-1), and formula (I4), X 10 , X 11b , X 6 ~X 9 , Y, p, and q2 have the same meanings as above. Q 1 and Q 2 each independently represents an inorganic anion or an organic anion.

[0171] In addition, the azo dye (I) is a compound (I4), and X in the compound (I4) is 6 and X 8 are the same and X 7 and X 9are the same, first, azidation of a diamine represented by the following formula (pt11-2A) is carried out to produce a diazonium salt represented by the formula (q11-2A). The compound represented by the formula (I4) can be produced by reacting the obtained diazonium salt represented by the formula (q11-2A) with the compounds represented by the formulas (pt2) and (pt3).

[0172] [ka] [In formula (pt11-2A), formula (pt2), formula (pt3), formula (q11-2A), and formula (I4), X 10 , X 11b , X 6 ~X 9 , Y, p, and q2 have the same meanings as above; X 6 and X 8 are identical, and X 7 and X 9 are identical. Q 1 and Q 2 each independently represents an inorganic anion or an organic anion.

[0173] The diazonium salts represented by formula (q1-1), formula (q1-2), formula (q1-2A), formula (q11-1), formula (q11-2), and formula (q11-2A) can be obtained by diazotizing the amines represented by formula (pt1-1), formula (pt1-2), formula (pt1-2A), formula (pt11-1), formula (pt11-2), and formula (pt11-2A), respectively, with nitrous acid, a nitrite, or a nitrite ester. The diazotization is carried out by any known method.

[0174] Examples of the inorganic anion include a fluoride ion, a chloride ion, a bromide ion, an iodide ion, a perchlorate ion, a hypochlorite ion, etc. Examples of the organic anion include CH3COO - , C6H5COO - etc. Q 1 and Q2 is preferably a chloride ion, a bromide ion, or CH3COO - It is.

[0175] In carrying out the diazotization reaction, an acid catalyst may be used to ensure that the reaction proceeds smoothly. Examples of the acid catalyst include mineral acids such as sulfuric acid and hydrochloric acid.

[0176] Compound (I1) can be produced by diazo coupling the diazonium salt represented by formula (q1-1) with the compound represented by formula (pt2). Compound (q2) can be produced by diazo coupling the diazonium salt represented by formula (q1-2) with the compound represented by formula (pt2). Compound (q3) can be produced by diazo coupling the diazonium salt represented by formula (q1-2A) with the compound represented by formula (pt2). Compound (I3) can be produced by diazo coupling the diazonium salt represented by formula (q11-1) with the compound represented by formula (pt2). Compound (q2-1) can be produced by diazo coupling the diazonium salt represented by formula (q11-2) with the compound represented by formula (pt2). In addition, the compound (I4) can be produced by diazo coupling the diazonium salt represented by formula (q11-2A) with the compounds represented by formula (pt2) and formula (pt3) (in this case, formula (pt2) and formula (pt3) are the same). These diazo couplings are carried out by any known method. The diazo coupling reaction is preferably carried out in the presence of an aqueous solvent. Examples of the aqueous solvent include water-soluble organic solvents such as methanol, ethanol, propanol, and 2-propanol, water, or a mixed solvent of water and the water-soluble organic solvent, and water or a mixed solvent of water and the water-soluble organic solvent is preferable.

[0177] A compound represented by formula (q3) can be produced by reducing a compound represented by formula (q2). A compound represented by formula (q3-1) can be produced by reducing a compound represented by formula (q2-1). The method of these reductions is not particularly limited and can be carried out by any known method, for example, reduction with a reducing agent such as a sulfide can be used. The sulfide is not particularly limited and examples thereof include hydrosulfides such as sodium hydrosulfide, potassium hydrosulfide, and ammonium hydrosulfide, and sulfides such as sodium sulfide, potassium sulfide, and ammonium sulfide. These may be anhydrous or contain water of crystallization. The reduction reaction is preferably carried out in the presence of an aqueous solvent. Examples of the aqueous solvent include the same solvents as those described above, and are preferably water or a mixed solvent of water and a water-soluble organic solvent.

[0178] The diazonium salt represented by formula (q4) can be obtained by diazotizing the amine represented by formula (q3). The diazonium salt represented by formula (q4-1) can be obtained by diazotizing the amine represented by formula (q3-1). As the method of diazotization, the same method as that of the diazotization of the compounds represented by formula (pt1-1), formula (pt1-2), formula (pt1-2A), formula (pt11-1), formula (pt11-2), and formula (pt11-2A) described above can be used.

[0179] Compound (I2) can be produced by diazo coupling the diazonium salt represented by formula (q4) with the compound represented by formula (pt3). Compound (I4) can be produced by diazo coupling the diazonium salt represented by formula (q4-1) with the compound represented by formula (pt3-1). As the method of these diazo couplings, the same method as the diazo coupling between the diazonium salt represented by formula (q1-1), formula (q1-2), formula (q11-1), or formula (q11-2) and the compound represented by formula (pt2) can be adopted.

[0180] Also, the substituents are -SO3M or -SO3T 0.5 In the case of producing an azo dye (I) having the formula (I), an azo dye having a sulfonic acid group as a substituent is produced by the above-mentioned method, and then an alkali metal salt or an alkaline earth metal salt is reacted with the sulfonic acid group of the azo dye. Examples of the alkali metal compound or alkaline earth metal compound include salts with chloride ions, salts with iodide ions, salts with bromide ions, salts with acetate ions, salts with formate ions, and salts with benzoate ions, and the like, with the salts with acetate ions being preferred.

[0181] The reaction with the alkali metal compound or alkaline earth metal compound is preferably carried out in the presence of a mixed solvent of an organic solvent and an aqueous solvent. The aqueous solvent may be the same as the aqueous solvent described above, and is preferably water. The organic solvent may be an ester solvent such as ethyl lactate, butyl lactate, n-butyl acetate, ethyl butyrate, or methyl acetoacetate; an ether solvent such as ethylene glycol monobutyl ether, diethylene glycol monomethyl ether, or propylene glycol monomethyl ether; a ketone solvent such as diacetone alcohol; an amide solvent such as N,N-dimethylformamide, N,N-dimethylacetamide, or N-methylpyrrolidone; or a halogen-based solvent such as chloroform or methylene chloride; and the like, and an amide solvent is preferred.

[0182] In addition, -SO2N(R 17 In the case of producing an azo dye (I) having a sulfonic acid group as a substituent by the above-mentioned method, an azo dye having a sulfonic acid group as a substituent is reacted with a halogenating agent to react with the sulfonic acid group of the azo dye, and a base and NH(R 17 The halogenating agent can be, for example, thionyl chloride, oxalyl chloride, phosphorus trichloride, phosphorus pentachloride, etc.

[0183] The halogenating agent, as well as a base and NH(R 17The reaction with 2) is preferably carried out in the presence of an organic solvent. Examples of the organic solvent include the same organic solvents as those mentioned above, and preferred are amide solvents and halogenated solvents.

[0184] Examples of the base include organic bases such as triethylamine, 4-(N,N-dimethylamino)pyridine, pyridine, and piperidine; metal alkoxides such as sodium methoxide, sodium ethoxide, sodium tert-butoxide, and potassium tert-butoxide; organometallic compounds such as butyllithium, tert-butyllithium, and phenyllithium; and inorganic bases such as lithium hydroxide, sodium hydroxide, and potassium hydroxide. Among these, organic bases are preferred.

[0185] The method for obtaining the target compound azo dye (I) (e.g., azo dyes (I1) to (I4)) from the reaction mixture is not particularly limited, and various known methods can be used. For example, an acid (e.g., acetic acid, etc.) can be added to the reaction mixture as necessary, and the precipitated crystals can be collected by filtration. Alternatively, after the reaction is completed, the solvent of the reaction mixture can be distilled off, a small amount of methanol is added and stirred, and an acid (e.g., acetic acid, etc.) and water are added to the resulting solution, and the precipitated crystals can be collected by filtration. The filtered crystals may be washed with a solvent such as water or methanol, and may further be dried. Furthermore, they may be further purified by a known method such as recrystallization, if necessary.

[0186] When the crystal structure of the obtained azo dye (I) does not exhibit the above-mentioned specified X-ray diffraction pattern, the obtained crystal is treated by the method including the above-mentioned contacting step and separation step to give a crystal structure exhibiting the specified X-ray diffraction pattern.

[0187] <Colored curable resin composition> The azo dye (Aa) having a specific crystal structure (preferably the azo dye (Ia)) may be contained in the following colored curable resin composition. The colored curable resin composition of the present invention includes the azo dye (Aa) (preferably the azo dye (Ia)), a resin (hereinafter referred to as resin (B)), a polymerizable compound (hereinafter also referred to as polymerizable compound (C)), a polymerization initiator (hereinafter also referred to as polymerization initiator (D)), and a solvent (hereinafter also referred to as solvent (E)). The azo dye (Aa) can be used as a colorant (hereinafter also referred to as colorant (A1)). The colored curable resin composition of the present invention may further contain a leveling agent (hereinafter also referred to as leveling agent (F)). In this specification, the compounds exemplified as each component may be used alone or in combination, unless otherwise specified.

[0188] <Colorant (A1)> The colorant (A1) contains an azo dye (Aa) having a specific crystal structure. When the colorant (A) contains the azo dye (Aa), the colored curable resin composition containing the colorant can form a color filter having improved heat resistance and light resistance.

[0189] <Azo dye (Aa)> The azo dye (Aa) is as described above, and the preferred embodiments thereof are also the same.

[0190] The content of the azo dye (Aa) relative to the total amount of the colorant (A1) is preferably 30% by mass or more, more preferably 40% by mass or more, even more preferably 50% by mass or more, still more preferably 60% by mass or more, even more preferably 70% by mass or more, and even more preferably 80% by mass or more, and may be 100% by mass or 95% by mass or less.

[0191] <Colorant (A1)> The colorant (A1) may contain a colorant other than the azo dye (Aa) in addition to the azo dye (Aa). The colorant other than the azo dye (Aa) may be either a dye (hereinafter also referred to as dye (A1-1)) or a pigment (hereinafter also referred to as pigment (A1-2)), and the colorant other than the azo dye (Aa) may contain one or both of the dye (A1-1) and the pigment (A1-2).

[0192] The dye (A1-1) is not particularly limited, and may be a known dye, as long as it does not include the azo dye (Aa), and examples thereof include solvent dyes, acid dyes, direct dyes, and mordant dyes. Examples of the dye include compounds classified as having a hue other than pigments in the Color Index (published by The Society of Dyers and Colourists) and known dyes described in Dyeing Notes (Shikisensha Co., Ltd.). According to the chemical structure, examples of the dye (A1-1) include cyanine dyes, triphenylmethane dyes, xanthene dyes, phthalocyanine dyes, anthraquinone dyes, naphthoquinone dyes, quinoneimine dyes, methine dyes, azomethine dyes, squarylium dyes, acridine dyes, styryl dyes, coumarin dyes, quinoline dyes, and nitro dyes. According to the crystal structure, examples of the azo dye that is the dye (A1-1) include azo dyes other than the azo dye (Aa). Of these, the dye (A1-1) is preferably an organic solvent-soluble dye.

[0193] Specific examples of the dye (A1-1) include CI Solvent Yellow 4 (hereinafter, the description of CI Solvent Yellow will be omitted and only the numbers will be used), 14, 15, 23, 24, 38, 62, 63, 68, 82, 94, 98, 99, 117, 162, 163, 167, and 189; CI Solvent Red 45, 49, 111, 125, 130, 143, 145, 146, 150, 151, 155, 168, 169, 172, 175, 181, 207, 218, 222, 227, 230, 245, 247; CI Solvent Orange 2, 7, 11, 15, 26, 56, 77, 86; CI Solvent Violet 11, 13, 14, 26, 31, 36, 37, 38, 45, 47, 48, 51, 59, 60; CI Solvent Blue 4, 5, 14, 18, 35, 36, 37, 45, 58, 59, 59:1, 63, 67, 68, 69, 70, 78, 79, 83, 90, 94, 97, 98, 100, 101, 102, 104, 105, 111, 112, 122, 128, 132, 136, 139; CI Solvent Dyes such as CI Solvent Green 1, 3, 4, 5, 7, 28, 29, 32, 33, 34, 35, etc. CI Acid Yellow 1, 3, 7, 9, 11, 17, 23, 25, 29, 34, 36, 38, 40, 42, 54, 65, 72, 73, 76, 79, 98, 99, 111, 112, 113, 114, 116, 119, 123, 128, 134, 135, 138, 139, 140, 144, 150, 155, 157, 160, 161, 163, 168, 169, 172, 177, 178, 179, 184, 190, 193, 196, 197, 199, 202, 203, 204, 205, 207, 212, 214, 220, 221, 228, 230, 232, 235, 238, 240, 242, 243, 251; CI Acid Red 1, 4, 8, 14, 17, 18, 26, 27, 29, 31, 33, 34, 35, 37, 40, 42, 44, 50, 51, 52, 57, 66, 73, 76, 80, 87, 88, 91, 92, 94, 95, 97, 98, 103, 106, 111, 114, 129, 133, 134, 138, 143, 145, 150, 151, 155, 158, 160, 172, 176, 1 82, 183, 195, 198, 206, 211, 215, 216, 217, 227, 228, 249, 252, 257, 258, 260, 261, 266, 268, 270, 274, 277, 280, 281, 289, 308, 312, 315, 316, 339, 341, 345, 346, 349, 382, ​​383, 388, 394, 401, 412, 417, 418, 422, 426; CI Acid Orange 6, 7, 8, 10, 12, 26, 50, 51, 52, 56, 62, 63, 64, 74, 75, 94, 95, 107, 108, 169, 173; CI Acid Violet 6B, 7, 9, 15, 16, 17, 19, 21, 23, 24, 25, 30, 34, 38, 49, 72, 102; CI Acid Blue 1, 3, 5, 7, 9, 11, 13, 15, 17, 18, 22, 23, 24, 25, 26, 27, 29, 34, 38, 40, 41, 42, 43, 45, 48, 51, 54, 59, 60, 62, 70, 72, 74, 75, 78, 80, 82, 83, 86, 87, 88, 90, 90:1, 91, 92, 93, 93:1, 96, 99, 100, 102, 103, 104, 108, 109, 110, 112, 113, 117, 119, 120, 1 23, 126, 127, 129, 130, 131, 138, 140, 142, 143, 147, 150, 151, 154, 158, 161, 166, 167, 168, 170, 171, 175, 182, 183, 184, 187, 192, 199, 203, 204, 205, 210, 213, 229, 234, 236, 242, 243, 256, 259, 267, 269, 278, 280, 285, 290, 296, 315, 324:1, 335, 340; CI Acid Dyes such as CI Acid Green 1, 3, 5, 6, 7, 8, 9, 11, 13, 14, 15, 16, 22, 25, 27, 28, 41, 50, 50:1, 58, 63, 65, 80, 104, 105, 106, 109, CI Direct Yellow 2, 33, 34, 35, 38, 39, 43, 47, 50, 54, 58, 68, 69, 70, 71, 86, 93, 94, 95, 98, 102, 108, 109, 129, 136, 138, 141; CI Direct Red 79, 82, 83, 84, 91, 92, 96, 97, 98, 99, 105, 106, 107, 172, 173, 176, 177, 179, 181, 182, 184, 204, 207, 211, 213, 218, 220, 221, 222, 232, 233, 234, 241, 243, 246, 250; CI Direct Orange 26, 34, 39, 41, 46, 50, 52, 56, 57, 61, 64, 65, 68, 70, 96, 97, 106, 107; CI Direct Violet 47, 52, 54, 59, 60, 65, 66, 79, 80, 81, 82, 84, 89, 90, 93, 95, 96, 103, 104; CI Direct Blue 1, 2, 3, 6, 8, 15, 22, 25, 28, 29, 40, 41, 42, 47, 52, 55, 57, 71, 76, 77, 78, 80, 81, 84, 85, 86, 90, 93, 94, 95, 97, 98, 99, 100, 101, 106, 107, 108, 109, 113, 114, 115, 117, 119, 120, 137, 149, 150, 153, 155, 156, 158, 159, 160, 161, 162, 163, 164, 165, 166, 167, 168, 170, 171, 172, 173, 188, 189, 190, 192, 193, 194, 195, 196, 198, 199, 200, 201, 202, 203, 207, 209, 210, 212, 213, 214, 222, 225, 226, 228, 229, 236, 237, 238, 242, 243, 244, 245, 246, 247, 248, 249, 250, 251, 252, 256, 257, 259, 260, 268, 274, 275, 293; CI Direct Dyes such as CI Direct Green 25, 27, 31, 32, 34, 37, 63, 65, 66, 67, 68, 69, 72, 77, 79, 82, etc. CI Disperse Yellow 51, 54, 76; CI Disperse Violet 26, 27; CI Disperse Dyes such as CI Disperse Blue 1, 14, 56, 60, etc. CI Basic Red 1, 10; CI Basic Blue 1, 3, 5, 7, 9, 19, 21, 22, 24, 25, 26, 28, 29, 40, 41, 45, 47, 54, 58, 59, 60, 64, 65, 66, 67, 68, 81, 83, 88, 89; CI Basic Violet 2; CI Basic Red 9; CI Basic dyes, such as CI Basic Green 1; CI Reactive Yellow 2,76,116; CI Reactive Orange 16; CI Reactive dyes such as CI Reactive Red 36; CI Mordant Yellow 5, 8, 10, 16, 20, 26, 30, 31, 33, 42, 43, 45, 56, 61, 62, 65; CI Mordant Red 1, 2, 3, 4, 9, 11, 12, 14, 17, 18, 19, 22, 23, 24, 25, 26, 27, 29, 30, 32, 33, 36, 37, 38, 39, 41, 42, 43, 45, 46, 48, 52, 53, 56, 62, 63, 71, 74, 76, 78, 85, 86, 88, 90, 94, 95; CI Mordant Orange 3, 4, 5, 8, 12, 13, 14, 20, 21, 23, 24, 28, 29, 32, 34, 35, 36, 37, 42, 43, 47, 48; CI Mordant Violet 1, 1:1, 2, 3, 4, 5, 6, 7, 8, 10, 11, 14, 15, 16, 17, 18, 19, 21, 22, 23, 24, 27, 28, 30, 31, 32, 33, 36, 37, 39, 40, 41, 44, 45, 47, 48, 49, 53, 58; CI Mordant Blue 1, 2, 3, 7, 8, 9, 12, 13, 15, 16, 19, 20, 21, 22, 23, 24, 26, 30, 31, 32, 39, 40, 41, 43, 44, 48, 49, 53, 61, 74, 77, 83, 84; CI Mordant dyes such as CI Mordant Green 1, 3, 4, 5, 10, 13, 15, 19, 21, 23, 26, 29, 31, 33, 34, 35, 41, 43, 53, Examples of such dyes include CI Vat dyes such as CI Vat Green 1.

[0194] These dyes may be appropriately selected according to the optical spectrum of the desired color filter.

[0195] When the colorant (A1) contains a dye (A1-1), the content thereof is preferably 0.1 mass % or more, more preferably 0.5 mass % or more, even more preferably 1 mass % or more, and still more preferably 3 mass % or more, based on the total amount of the colorant (A1), and is preferably 15 mass % or less, more preferably 10 mass % or less.

[0196] The pigment (A1-2) is not particularly limited, and any known pigment can be used as long as it does not include an azo colorant (Aa). Examples of the pigment include pigments classified as pigments in the Color Index (published by The Society of Dyers and Colourists).

[0197] Examples of the pigment (A1-2) include yellow pigments such as CI Pigment Yellow 1, 3, 10, 12, 13, 14, 15, 16, 17, 20, 24, 31, 53, 81, 83, 86, 93, 94, 109, 110, 117, 125, 128, 129, 137, 138, 139, 147, 148, 150, 153, 154, 166, 173, 185, 194, 214, and 231; Orange pigments such as CI Pigment Orange 13, 31, 36, 38, 40, 42, 43, 51, 55, 59, 61, 62, 64, 65, 71, 72, 73; Red pigments such as CI Pigment Red 9, 97, 105, 122, 123, 144, 149, 166, 168, 176, 177, 179, 180, 190, 192, 202, 209, 215, 216, 224, 242, 254, 255, 264, 265, 266, 268, 269, 273, 291, 295, 296; Blue pigments such as CI Pigment Blue 15, 15:3, 15:4, 15:6, 60; Violet pigments such as CI Pigment Violet 1, 19, 23, 29, 32, 36, 38; Green pigments such as CI Pigment Green 7, 36, 58, 59, 62, 63; Brown pigments such as CI Pigment Brown 23, 25; Black pigments such as CI Pigment Black 1 and 7;

[0198] The pigment may be subjected, as necessary, to a rosin treatment, a surface treatment using a pigment derivative into which an acidic group or a basic group has been introduced, or the like, a grafting treatment onto the pigment surface using a polymer compound or the like, a particle size reduction treatment using a sulfuric acid atomization method or the like, a washing treatment using an organic solvent or water for removing impurities, a removal treatment of ionic impurities using an ion exchange method or the like, or the like.

[0199] As the colorant (A1) other than the azo dye (Aa), the pigment (A1-2) is preferable, and the pigment surface-treated with the pigment derivative is more preferable. By using the pigment surface-treated with the pigment derivative, the dispersibility of the azo dye (Aa) in the colored curable resin composition is improved.

[0200] A preferred example of a pigment that has been surface-treated with a pigment derivative is compound (A1-21) (hereinafter also referred to as compound (A1-21)), which has a pigment (preferably an organic pigment) as a base material to which a sulfonic acid group or a salt thereof, or a sulfonamide group is bonded.

[0201] The compound (A1-21) is preferably one to which at least one of a sulfonic acid and an amine salt of sulfonic acid is bonded.

[0202] As the organic pigment that serves as the base material for compound (A1-21), quinophthalone pigments such as CI Pigment Yellow 138, CI Pigment Yellow 231, and CI Pigment Yellow 233 are preferred, with CI Pigment Yellow 138 being more preferred.

[0203] Compound (A1-21) can be produced, for example, according to the method described in JP-A No. 2002-179979.

[0204] It is preferable that the pigment has a uniform particle size. By carrying out a dispersion treatment in the presence of a dispersant, it is possible to obtain a pigment dispersion in which the pigment is uniformly dispersed in the solution.

[0205] Examples of the dispersant include cationic, anionic, nonionic, amphoteric, polyester, polyamine, and acrylic surfactants. These dispersants may be used alone or in combination of two or more. Examples of the dispersant include KP (manufactured by Shin-Etsu Chemical Co., Ltd.), FLOWRENE (manufactured by Kyoeisha Chemical Co., Ltd.), Solsperse (manufactured by Zeneca Co., Ltd.), EFKA (manufactured by CIBA), AJISPER (manufactured by Ajinomoto Fine-Techno Co., Ltd.), and Disperbyk (manufactured by BYK-Chemie Co., Ltd.). When a dispersant is used, the amount of the dispersant used is preferably from 1% by mass to 100% by mass, more preferably from 5% by mass to 50% by mass, based on the total amount of the pigment. When the amount of the dispersant used is within the above range, a pigment dispersion in a uniformly dispersed state tends to be obtained.

[0206] When the colorant (A1) contains a pigment (A1-2), the content thereof is preferably 0.05 mass% or more, more preferably 0.1 mass% or more, even more preferably 0.5 mass% or more, and still more preferably 0.8 mass% or more, based on the total amount of the colorant (A1), and is preferably 15 mass% or less, more preferably 10 mass% or less.

[0207] The content of the colorant (A1) is preferably 0.1% by mass or more and 70% by mass or less, more preferably 0.5% by mass or more and 60% by mass or less, and even more preferably 1% by mass or more and 50% by mass or less, based on the total amount of solids. When the content of the colorant (A1) is within the above range, the color density when made into a color filter is sufficient, and the resin (B) and the polymerizable compound (C) can be contained in the composition in the necessary amounts, so that a colored coating film (colored pattern) with sufficient mechanical strength can be formed.

[0208] Here, the "total amount of solids" in this specification refers to the amount obtained by subtracting the content of the solvent from the total amount of the colored curable resin composition. The total amount of solids and the content of each component relative thereto can be measured by a known analytical means such as liquid chromatography or gas chromatography.

[0209] <Resin (B)> Resin (B) is not particularly limited, but is preferably an alkali-soluble resin. Examples of resin (B) include the following resins [K1] to [K6], and it is preferably at least one selected from resins [K1] to [K6].

[0210] Resin [K1]: a copolymer having a structural unit derived from at least one monomer (a) (hereinafter also referred to as "(a)") selected from the group consisting of unsaturated carboxylic acids and unsaturated carboxylic anhydrides, and a structural unit derived from a monomer (b) (hereinafter also referred to as "(b)") having a cyclic ether structure having 2 to 4 carbon atoms and an ethylenically unsaturated bond; Resin [K2]: a copolymer having a structural unit derived from the (a), a structural unit derived from the (b), and a structural unit derived from a monomer (c) copolymerizable with (a) (however, different from (a) and (b)) (hereinafter also referred to as "(c)"); Resin [K3]: a copolymer having structural units derived from the (a) and structural units derived from the (c); Resin [K4]: a copolymer having a structural unit derived from the (a) to which the (b) has been added and a structural unit derived from the (c), the copolymer including a structural unit derived from the (a) to which the (b) has not been added; Resin [K4']: a copolymer having a structural unit derived from (a) and a structural unit derived from (c), and not including a structural unit derived from (a) to which (b) is added; Resin [K5]: a copolymer having a structural unit derived from the (b) to which the (a) has been added and a structural unit derived from the (c) (which may contain, but preferably does not contain, a structural unit derived from the (b) to which the (a) has not been added); Resin [K6]: A copolymer having a structural unit obtained by adding the (a) to a structural unit derived from the (b) and further adding a carboxylic acid anhydride, and a structural unit derived from (c).

[0211] Specific examples of (a) include unsaturated monocarboxylic acids such as acrylic acid, methacrylic acid, crotonic acid, o-, m-, and p-vinylbenzoic acid; Unsaturated dicarboxylic acids such as maleic acid, fumaric acid, citraconic acid, mesaconic acid, itaconic acid, 3-vinylphthalic acid, 4-vinylphthalic acid, 3,4,5,6-tetrahydrophthalic acid, 1,2,3,6-tetrahydrophthalic acid, dimethyltetrahydrophthalic acid, and 1,4-cyclohexenedicarboxylic acid; Bicyclounsaturated compounds containing a carboxy group, such as methyl-5-norbornene-2,3-dicarboxylic acid, 5-carboxybicyclo[2.2.1]hept-2-ene, 5,6-dicarboxybicyclo[2.2.1]hept-2-ene, 5-carboxy-5-methylbicyclo[2.2.1]hept-2-ene, 5-carboxy-5-ethylbicyclo[2.2.1]hept-2-ene, 5-carboxy-6-methylbicyclo[2.2.1]hept-2-ene, and 5-carboxy-6-ethylbicyclo[2.2.1]hept-2-ene; Unsaturated dicarboxylic acid anhydrides such as maleic anhydride, citraconic anhydride, itaconic anhydride, 3-vinylphthalic anhydride, 4-vinylphthalic anhydride, 3,4,5,6-tetrahydrophthalic anhydride, 1,2,3,6-tetrahydrophthalic anhydride, dimethyltetrahydrophthalic anhydride, and 5,6-dicarboxybicyclo[2.2.1]hept-2-ene anhydride; Unsaturated mono[(meth)acryloyloxyalkyl] esters of divalent or higher polyvalent carboxylic acids, such as mono[2-(meth)acryloyloxyethyl] succinate and mono[2-(meth)acryloyloxyethyl] phthalate; Examples include unsaturated acrylates containing a hydroxy group and a carboxy group in the same molecule, such as α-(hydroxymethyl)acrylic acid. Among these, acrylic acid, methacrylic acid, maleic anhydride, etc. are preferred from the standpoint of copolymerization reactivity and solubility of the resulting resin in a developer (particularly an aqueous alkaline solution).

[0212] In this specification, the term "(meth)acrylic acid" refers to at least one selected from the group consisting of acrylic acid and methacrylic acid. The terms "(meth)acryloyl" and "(meth)acrylate" have the same meaning.

[0213] (b) is, for example, a polymerizable compound having a cyclic ether structure having 2 to 4 carbon atoms (for example, at least one selected from the group consisting of an oxirane ring, an oxetane ring, and a tetrahydrofuran ring) and an ethylenically unsaturated bond. (b) is preferably a monomer having a cyclic ether having 2 to 4 carbon atoms and a (meth)acryloyloxy group.

[0214] Examples of (b) include a monomer (b1) having an oxiranyl group and an ethylenically unsaturated bond (hereinafter also referred to as "(b1)"), a monomer (b2) having an oxetanyl group and an ethylenically unsaturated bond (hereinafter also referred to as "(b2)"), and a monomer (b3) having a tetrahydrofuryl group and an ethylenically unsaturated bond (hereinafter also referred to as "(b3)").

[0215] Examples of (b1) include a monomer (b1-1) (hereinafter also referred to as "(b1-1)") having a structure in which a linear or branched aliphatic unsaturated hydrocarbon is epoxidized, and a monomer (b1-2) (hereinafter also referred to as "(b1-2)") having a structure in which an alicyclic unsaturated hydrocarbon is epoxidized.

[0216] Examples of (b1-1) include glycidyl (meth)acrylate, β-methyl glycidyl (meth)acrylate, β-ethyl glycidyl (meth)acrylate, glycidyl vinyl ether, o-vinylbenzyl glycidyl ether, m-vinylbenzyl glycidyl ether, p-vinylbenzyl glycidyl ether, α-methyl-o-vinylbenzyl glycidyl ether, α-methyl-m-vinylbenzyl glycidyl ether, α-methyl-p-vinylbenzyl glycidyl ether, 2,3-bis(glycidyl Examples of such styrene include 2,4-bis(glycidyloxymethyl)styrene, 2,5-bis(glycidyloxymethyl)styrene, 2,6-bis(glycidyloxymethyl)styrene, 2,3,4-tris(glycidyloxymethyl)styrene, 2,3,5-tris(glycidyloxymethyl)styrene, 2,3,6-tris(glycidyloxymethyl)styrene, 3,4,5-tris(glycidyloxymethyl)styrene, and 2,4,6-tris(glycidyloxymethyl)styrene.

[0217] Examples of (b1-2) include vinylcyclohexene monoxide, 1,2-epoxy-4-vinylcyclohexane (e.g., Celloxide 2000; manufactured by Daicel Corporation), 3,4-epoxycyclohexylmethyl (meth)acrylate (e.g., Cyclomer A400; manufactured by Daicel Corporation), 3,4-epoxycyclohexylmethyl (meth)acrylate (e.g., Cyclomer M100; manufactured by Daicel Corporation), compounds represented by formula (R1), and compounds represented by formula (R2).

[0218] [ka] [In formula (R1) and formula (R2), R ra and R rb represents a hydrogen atom or an alkyl group having 1 to 4 carbon atoms, and the hydrogen atom contained in the alkyl group may be substituted with a hydroxy group. X ra and X rb is a single bond, *-R rc -, *-Rrc -O-, *-R rc -S- or *-R rc -NH-. R rc represents an alkanediyl group having 1 to 6 carbon atoms. * represents a bond to O.]

[0219] Examples of the alkyl group having 1 to 4 carbon atoms include a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, a sec-butyl group, and a tert-butyl group. Examples of the alkyl group in which a hydrogen atom is substituted with a hydroxy group include a hydroxymethyl group, a 1-hydroxyethyl group, a 2-hydroxyethyl group, a 1-hydroxypropyl group, a 2-hydroxypropyl group, a 3-hydroxypropyl group, a 1-hydroxy-1-methylethyl group, a 2-hydroxy-1-methylethyl group, a 1-hydroxybutyl group, a 2-hydroxybutyl group, a 3-hydroxybutyl group, and a 4-hydroxybutyl group. R ra and R rb Preferred examples of the alkyl group include a hydrogen atom, a methyl group, a hydroxymethyl group, a 1-hydroxyethyl group, and a 2-hydroxyethyl group, and more preferred examples include a hydrogen atom and a methyl group.

[0220] Examples of the alkanediyl group include a methylene group, an ethylene group, a propane-1,2-diyl group, a propane-1,3-diyl group, a butane-1,4-diyl group, a pentane-1,5-diyl group, and a hexane-1,6-diyl group. X ra and X rb Preferred examples of the group include a single bond, a methylene group, an ethylene group, *-CH2-O-, and *-CH2CH2-O-, and more preferred examples include a single bond and *-CH2CH2-O- (* represents a bond to O).

[0221] Examples of the compound represented by formula (R1) include compounds represented by any of formulas (R1-1) to (R1-15). Among them, compounds represented by formulas (R1-1), (R1-3), (R1-5), (R1-7), (R1-9), or (R1-11) to (R1-15) are preferred, and compounds represented by formulas (R1-1), (R1-7), (R1-9), or (R1-15) are more preferred.

[0222] [ka]

[0223] [ka]

[0224] Examples of the compound represented by formula (R2) include compounds represented by any of formulas (R2-1) to (R2-15). Among them, compounds represented by formulas (R2-1), (R2-3), (R2-5), (R2-7), (R2-9), or (R2-11) to (R2-15) are preferred, and compounds represented by formulas (R2-1), (R2-7), (R2-9), or (R2-15) are more preferred.

[0225] [ka]

[0226] [ka]

[0227] The compound represented by formula (R1) and the compound represented by formula (R2) may be used alone or in combination of two or more. When the compound represented by formula (R1) and the compound represented by formula (R2) are used in combination, the content ratio thereof [compound represented by formula (R1):compound represented by formula (R2)] is preferably 5:95 to 95:5, more preferably 20:80 to 80:20 on a molar basis.

[0228] As (b2), a monomer having an oxetanyl group and a (meth)acryloyloxy group is more preferable. As (b2), 3-methyl-3-methacryloyloxymethyloxetane, 3-methyl-3-acryloyloxymethyloxetane, 3-ethyl-3-methacryloyloxymethyloxetane, 3-ethyl-3-acryloyloxymethyloxetane, 3-methyl-3-methacryloyloxyethyloxetane, 3-methyl-3-acryloyloxyethyloxetane, 3-ethyl-3-methacryloyloxyethyloxetane, 3-ethyl-3-acryloyloxyethyloxetane, and the like can be mentioned.

[0229] As (b3), a monomer having a tetrahydrofuryl group and a (meth)acryloyloxy group is more preferable. Specific examples of (b3) include tetrahydrofurfuryl acrylate (e.g., Viscoat V#150, manufactured by Osaka Organic Chemical Industry Co., Ltd.), tetrahydrofurfuryl methacrylate, etc.

[0230] As (b), (b1) is preferable in that the reliability of the heat resistance, chemical resistance, etc. of the obtained color filter can be improved. Furthermore, (b1-2) is more preferable in that the storage stability of the colored curable resin composition is excellent.

[0231] Examples of (c) include (meth)acrylic acid ester monomers, unsaturated carboxylates such as unsaturated dicarboxylates, and vinyl monomers having an unsaturated aliphatic hydrocarbon ring, an unsaturated heterocycle, or an aromatic ring. Examples of the (meth)acrylic acid ester monomer include (meth)acrylic acid esters having a linear or branched aliphatic saturated hydrocarbon group, such as methyl (meth)acrylate, ethyl (meth)acrylate, n-butyl (meth)acrylate, sec-butyl (meth)acrylate, tert-butyl (meth)acrylate, 2-ethylhexyl (meth)acrylate, dodecyl (meth)acrylate, lauryl (meth)acrylate, stearyl (meth)acrylate, and cyclopentyl (meth)acrylate; (meth)acrylic acid esters having a linear or branched aliphatic unsaturated hydrocarbon group, such as allyl (meth)acrylate and propargyl (meth)acrylate; Cyclohexyl (meth)acrylate, 2-methylcyclohexyl (meth)acrylate, tricyclo[5.2.1.0 2,6 ](meth)acrylic acid esters having a cyclic saturated hydrocarbon group, such as decan-8-yl (meth)acrylate (commonly referred to in the technical field as "dicyclopentanyl (meth)acrylate" and also referred to as "tricyclodecyl (meth)acrylate"), isobornyl (meth)acrylate, and adamantyl (meth)acrylate; Tricyclo[5.2.1.0 2,6 ](meth)acrylic acid esters having a cyclic unsaturated aliphatic hydrocarbon group, such as decene-8-yl (meth)acrylate (commonly referred to as "dicyclopentenyl (meth)acrylate" in the technical field), and dicyclopentanyloxyethyl (meth)acrylate; (meth)acrylic acid esters having an aromatic ring, such as phenyl (meth)acrylate, naphthyl (meth)acrylate, benzyl (meth)acrylate, and phenoxybenzyl (meth)acrylate; Examples of the hydroxyl group-containing (meth)acrylic acid esters include 2-hydroxyethyl (meth)acrylate and 2-hydroxypropyl (meth)acrylate. Examples of the unsaturated dicarboxylic acid ester include dicarboxylic acid diesters such as diethyl maleate, diethyl fumarate, and diethyl itaconate.

[0232] Among these unsaturated carboxylates, C esters such as methyl methacrylate and 2-ethylhexyl acrylate are 1-10 Alkyl (meth)acrylate; Tricyclo[5.2.1.0 2,6 ](meth)acrylic acid esters having a cyclic saturated hydrocarbon group, such as decan-8-yl (meth)acrylate; Tricyclo[5.2.1.0 2,6 ](meth)acrylic acid esters having a cyclic unsaturated aliphatic hydrocarbon group, such as decene-8-yl (meth)acrylate; Preferred are (meth)acrylic acid esters having an aromatic ring, such as benzyl (meth)acrylate and phenoxybenzyl (meth)acrylate.

[0233] Examples of vinyl monomers having an unsaturated aliphatic hydrocarbon ring include bicyclo[2.2.1]hept-2-ene (also called 2-norbornene), 5-methylbicyclo[2.2.1]hept-2-ene, 5-ethylbicyclo[2.2.1]hept-2-ene, 5-hydroxybicyclo[2.2.1]hept-2-ene, 5-hydroxymethylbicyclo[2.2.1]hept-2-ene, 5-(2'-hydroxyphenyl)-2-phenyl ... 5,6-di(2'-hydroxyethyl)bicyclo[2.2.1]hept-2-ene, 5-methoxybicyclo[2.2.1]hept-2-ene, 5-ethoxybicyclo[2.2.1]hept-2-ene, 5,6-dihydroxybicyclo[2.2.1]hept-2-ene, 5,6-di(hydroxymethyl)bicyclo[2.2.1]hept-2-ene, 5,6-di(2'-hydroxyethyl)bicyclo[2.2.1]hept-2-ene, 5,6 -Dimethoxybicyclo[2.2.1]hept-2-ene, 5,6-diethoxybicyclo[2.2.1]hept-2-ene, 5-hydroxy-5-methylbicyclo[2.2.1]hept-2-ene, 5-hydroxy-5-ethylbicyclo[2.2.1]hept-2-ene, 5-hydroxymethyl-5-methylbicyclo[2.2.1]hept-2-ene, 5-tert-butoxycarbonylbicyclo[2.2.1 ]hept-2-ene, 5-cyclohexyloxycarbonylbicyclo[2.2.1]hept-2-ene, 5-phenoxycarbonylbicyclo[2.2.1]hept-2-ene, 5,6-bis(tert-butoxycarbonyl)bicyclo[2.2.1]hept-2-ene, and 5,6-bis(cyclohexyloxycarbonyl)bicyclo[2.2.1]hept-2-ene are examples of bicyclo unsaturated compounds. Examples of vinyl monomers having an unsaturated heterocycle include dicarbonyl imide derivatives such as N-phenylmaleimide, N-cyclohexylmaleimide, N-benzylmaleimide, N-succinimidyl-3-maleimidobenzoate, N-succinimidyl-4-maleimidobutyrate, N-succinimidyl-6-maleimidocaproate, N-succinimidyl-3-maleimidopropionate, and N-(9-acridinyl)maleimide. Examples of vinyl monomers having an aromatic ring include styrene-based monomers such as styrene, α-methylstyrene, m-methylstyrene, p-methylstyrene, vinyltoluene, and p-methoxystyrene. Other vinyl monomers include nitrile group-containing monomers such as acrylonitrile and methacrylonitrile; Halogen atom-containing monomers such as vinyl chloride and vinylidene chloride; Examples of the monomer include acrylamide, methacrylamide, vinyl acetate, 1,3-butadiene, isoprene, and 2,3-dimethyl-1,3-butadiene. Among these vinyl monomers, from the viewpoints of copolymerization reactivity and heat resistance, styrene-based monomers such as styrene and vinyltoluene, dicarbonyl imide derivatives such as N-phenylmaleimide, N-cyclohexylmaleimide and N-benzylmaleimide, and bicyclounsaturated compounds such as bicyclo[2.2.1]hept-2-ene (also called 2-norbornene) are preferred.

[0234] The structural unit obtained by adding (b) to a structural unit derived from (a) refers to a unit formed by bonding (b) to a structural unit derived from (a) constituting the main chain of the copolymer by addition, and has a pendant unsaturated group derived from (b). In this structural unit, (a) may be any of the above-mentioned examples, and (b) may also be any of the above-mentioned examples. As (a), an unsaturated monocarboxylic acid such as (meth)acrylic acid is preferable. As (b), a monomer (b1) having an oxiranyl group and an ethylenically unsaturated bond is preferable, and a monomer (b1-1) having a structure in which a linear or branched aliphatic unsaturated hydrocarbon is epoxidized is more preferable.

[0235] The structural unit obtained by adding (a) to a structural unit derived from (b) refers to a unit formed by bonding (a) to a structural unit derived from (b) constituting the main chain of the copolymer by addition, and has a pendant unsaturated group derived from (a). In this structural unit, (b) may be any of the above-mentioned examples, and (a) may also be any of the above-mentioned examples. As (b), a monomer (b1) having an oxiranyl group and an ethylenically unsaturated bond is preferable, and a monomer (b1-1) having a structure in which a linear or branched aliphatic unsaturated hydrocarbon is epoxidized is more preferable. As (a), an unsaturated monocarboxylic acid such as (meth)acrylic acid is preferable.

[0236] The structural unit obtained by adding (a) to a structural unit derived from (b) and further adding a carboxylic anhydride refers to a structural unit obtained by half-esterification of a carboxylic anhydride to a hydroxyl group generated by adding (a) to a structural unit derived from (b) constituting the main chain of the copolymer, and has a pendant carboxyl group derived from the carboxylic anhydride and a pendant unsaturated group derived from (a). In this structural unit, (b) may be any of the above-mentioned examples, and (a) may also be any of the above-mentioned examples. As (b), a monomer (b1) having an oxiranyl group and an ethylenically unsaturated bond is preferable, and a monomer (b1-1) having a structure in which a linear or branched aliphatic unsaturated hydrocarbon is epoxidized is more preferable. As (a), an unsaturated monocarboxylic acid such as (meth)acrylic acid is preferable. Examples of the carboxylic acid anhydride include saturated aliphatic polycarboxylic acid anhydrides such as malonic anhydride, succinic anhydride, glutaric anhydride, and adipic anhydride; unsaturated aliphatic polycarboxylic acid anhydrides such as maleic anhydride, citraconic anhydride, and itaconic anhydride; aromatic polycarboxylic acid anhydrides such as 3-vinylphthalic anhydride and 4-vinylphthalic anhydride; and alicyclic polycarboxylic acid anhydrides such as 3,4,5,6-tetrahydrophthalic anhydride, 1,2,3,6-tetrahydrophthalic anhydride, dimethyltetrahydrophthalic anhydride, and 5,6-dicarboxybicyclo[2.2.1]hept-2-ene anhydride.

[0237] In the resin [K1], the ratio of structural units derived from each of them is as follows among all structural units constituting the resin [K1]: Structural units derived from (a): 2 to 60 mol% Structural units derived from (b): 40 to 98 mol% It is preferred that Structural units derived from (a): 10 to 50 mol% Structural units derived from (b): 50 to 90 mol% It is more preferable that: It is also preferred that the polymer contains substantially no structural units derived from (c). The total of the structural units derived from (a) and the structural units derived from (b) is, for example, 90 mol % or more, preferably 95 mol % or more, more preferably 98 mol % or more, and particularly preferably 100 mol % of all the structural units constituting the resin [K1]. When the ratio of the structural units of the resin [K1] is within the above range, the colored curable resin composition tends to have excellent storage stability, developability when forming a colored pattern, and solvent resistance of the obtained color filter.

[0238] Resin [K1] can be produced, for example, by the method described in the literature "Experimental Methods of Polymer Synthesis" (written by Takayuki Otsu, published by Kagaku Dojin Co., Ltd., 1st edition, 1st printing, published on March 1, 1972) and by reference to the cited references described in said literature.

[0239] Specifically, a method is exemplified in which a predetermined amount of (a) and (b), a polymerization initiator, a solvent, etc. are placed in a reaction vessel, and the atmosphere is deoxygenated by, for example, replacing oxygen with nitrogen, and the mixture is heated and kept warm while stirring. The polymerization initiator and solvent used here are not particularly limited, and those commonly used in the field can be used. For example, the polymerization initiator includes an azo compound (2,2'-azobisisobutyronitrile, 2,2'-azobis(2,4-dimethylvaleronitrile), etc.) and an organic peroxide (benzoyl peroxide, etc.), and the solvent may be any one that dissolves each monomer, and examples of the solvent include the solvent described below as the solvent (E) of the colored curable resin composition of the present invention.

[0240] The obtained copolymer may be used as it is in the solution after the reaction, or may be used after being concentrated or diluted, or may be used as a solid (powder) extracted by a method such as reprecipitation. In particular, by using a solvent contained in the colored curable resin composition of the present invention as a solvent during this polymerization, the solution after the reaction can be used as it is for the preparation of the colored curable resin composition of the present invention, and therefore the manufacturing process of the colored curable resin composition of the present invention can be simplified.

[0241] In the resin [K2], the ratio of structural units derived from each of them is as follows among all structural units constituting the resin [K2]: Structural units derived from (a): 1 to 70 mol% Structural units derived from (b): 1 to 60 mol% Structural units derived from (c): 20 to 95 mol% It is preferred that Structural units derived from (a): 3 to 50 mol% Structural units derived from (b): 3 to 40 mol% Structural units derived from (c): 30 to 90 mol% It is more preferable that Structural units derived from (a): 5 to 40 mol% Structural units derived from (b): 5 to 30 mol% Structural units derived from (c): 40 to 80 mol% It is even more preferred that: The total of the structural units derived from (a), the structural units derived from (b), and the structural units derived from (c) is, for example, 90 mol % or more, preferably 95 mol % or more, more preferably 98 mol % or more, and particularly preferably 100 mol % of all the structural units constituting the resin [K2]. When the ratio of the structural units of the resin [K2] is within the above range, the colored curable resin composition tends to have excellent storage stability, developability when forming a colored pattern, and the obtained color filter tends to have excellent solvent resistance, heat resistance, and mechanical strength.

[0242] In the resin [K2], (a) is preferably an unsaturated monocarboxylic acid such as (meth)acrylic acid. (b) is preferably a monomer (b1) having an oxiranyl group and an ethylenically unsaturated bond, and more preferably a monomer (b1-2) having a structure in which an alicyclic unsaturated hydrocarbon is epoxidized. (c) is preferably a (meth)acrylic acid ester having a cyclic unsaturated aliphatic hydrocarbon group, a (meth)acrylic acid ester having an aromatic ring, or a dicarbonyl imide derivative.

[0243] Resin [K2] can be produced, for example, in the same manner as described above as the method for producing resin [K1].

[0244] In the resin [K3], the ratio of structural units derived from each of them is as follows among all structural units constituting the resin [K3]: Structural units derived from (a): 2 to 60 mol% Structural units derived from (c): 40 to 98 mol% It is preferred that Structural units derived from (a): 10 to 50 mol% Structural units derived from (c): 50 to 90 mol% It is more preferable that Structural units derived from (a): 35 to 45 mol% Structural units derived from (c): 55 to 65 mol% It is even more preferred that: In addition, it is preferable that the polymer contains substantially no structural units derived from (b). The total of the structural units derived from (a) and the structural units derived from (c) is, for example, 90 mol% or more, preferably 95 mol% or more, more preferably 98 mol% or more, and particularly preferably 100 mol% of all the structural units constituting the resin [K3].

[0245] In the resin [K3], (a) is preferably an unsaturated monocarboxylic acid such as (meth)acrylic acid, and (c) is preferably a (meth)acrylic acid ester having an aromatic ring. Resin [K3] can be produced, for example, in the same manner as described above as the method for producing resin [K1].

[0246] In the resin [K4], the ratio of structural units derived from each of them is as follows among all structural units constituting the resin [K4]: Structural units derived from (a) (without addition of (b)); 1 to 60 mol% Structural units obtained by adding (b) to structural units derived from (a): 1 to 50 mol% Structural units derived from (c): 30 to 90 mol% It is preferred that Structural units derived from (a) (without addition of (b)); 5 to 50 mol% Structural units obtained by adding (b) to structural units derived from (a): 5 to 40 mol% Structural units derived from (c): 35 to 80 mol% It is more preferable that Structural units derived from (a) (without (b) added): 10 to 40 mol% Structural units obtained by adding (b) to structural units derived from (a): 10 to 25 mol% Structural units derived from (c): 40 to 75 mol% It is even more preferred that: The total of the structural units derived from (a) (without the addition of (b)), the structural units obtained by adding (b) to the structural units derived from (a), and the structural units derived from (c) is, for example, 90 mol % or more, preferably 95 mol % or more, more preferably 98 mol % or more, and particularly preferably 100 mol % of all the structural units constituting the resin [K4].

[0247] As the structural unit derived from (a) (without addition of (b)), a structural unit derived from an unsaturated monocarboxylic acid such as (meth)acrylic acid is preferred. As the structural unit obtained by adding (b) to a structural unit derived from (a), a structural unit obtained by adding a monomer (b1-1) having a structure in which a linear or branched aliphatic unsaturated hydrocarbon is epoxidized to a structural unit derived from an unsaturated monocarboxylic acid such as (meth)acrylic acid is preferred. As the structural unit derived from (c), one or more types selected from (meth)acrylic acid esters having a linear or branched aliphatic saturated hydrocarbon group, (meth)acrylic acid esters having a cyclic saturated hydrocarbon group, (meth)acrylic acid esters having an aromatic ring, bicyclo unsaturated compounds, and styrene-based monomers are preferred, and two or more types are more preferred. When (c) has two types of structural units derived from (c), it is preferable to select two types from unsaturated carboxylic acid esters such as (meth)acrylic acid esters, (meth)acrylic acid esters having a cyclic saturated hydrocarbon group, and (meth)acrylic acid esters having an aromatic ring, and to select two or more types from bicyclo unsaturated compounds, and vinyl monomers such as styrene-based monomers.

[0248] Resin [K4] can be produced by obtaining a copolymer of (a) and (c), and then adding the cyclic ether having 2 to 4 carbon atoms contained in (b) to the carboxylic acid and / or carboxylic acid anhydride contained in (a). First, a copolymer of (a) and (c) is produced in the same manner as described for the production method of resin [K1]. In this case, the ratio of the structural units derived from each is preferably the same as that described for resin [K3].

[0249] Next, a part of the carboxylic acid and / or carboxylic acid anhydride derived from (a) in the copolymer is reacted with a cyclic ether having 2 to 4 carbon atoms contained in (b). Following the production of the copolymer of (a) and (c), the atmosphere in the flask is replaced with air from nitrogen, and (b), a reaction catalyst for the reaction of a carboxylic acid or a carboxylic acid anhydride with a cyclic ether (e.g., tris(dimethylaminomethyl)phenol, etc.), a polymerization inhibitor (e.g., hydroquinone, etc.), etc. are placed in the flask, and the mixture is reacted, for example, at 60 to 130°C for 1 to 10 hours to produce the resin [K4]. The amount of (b) used is preferably 5 to 80 mol, more preferably 10 to 75 mol, relative to 100 mol of (a). By using this range, the storage stability of the colored curable resin composition, the developability when forming a pattern, and the solvent resistance, heat resistance, mechanical strength, and sensitivity of the obtained pattern tend to be well-balanced. The amount of the reaction catalyst used is preferably 0.001 to 5 parts by mass per 100 parts by mass of the total amount of (a), (b), and (c).The amount of the polymerization inhibitor used is preferably 0.001 to 5 parts by mass per 100 parts by mass of the total amount of (a), (b), and (c). The reaction conditions such as the charging method, reaction temperature and time can be appropriately adjusted in consideration of the production equipment, the amount of heat generated by the polymerization, etc. As with the polymerization conditions, the charging method and reaction temperature can be appropriately adjusted in consideration of the production equipment, the amount of heat generated by the polymerization, etc.

[0250] In the resin [K4'], the ratio of the structural units derived from each of them is as follows among all the structural units constituting the resin [K4']: Structural units obtained by adding (b) to structural units derived from (a); 5 to 95 mol% Structural units derived from (c): 5 to 95 mol% It is preferred that Structural units obtained by adding (b) to structural units derived from (a): 15 to 90 mol% Structural units derived from (c): 10 to 85 mol% It is more preferable that Structural units obtained by adding (b) to structural units derived from (a): 20 to 80 mol% Structural units derived from (c): 20 to 80 mol% It is even more preferred that: In addition, it does not substantially include structural units derived from (a) to which (b) is not added. The total of the structural units obtained by adding (b) to the structural units derived from (a) and the structural units derived from (c) is, for example, 90 mol% or more, preferably 95 mol% or more, more preferably 98 mol% or more, and particularly preferably 100 mol% of all the structural units constituting the resin [K4'].

[0251] The structural unit obtained by adding (b) to the structural unit derived from (a) is preferably a structural unit obtained by adding a monomer (b1-1) having a structure in which a linear or branched aliphatic unsaturated hydrocarbon is epoxidized to a structural unit derived from an unsaturated monocarboxylic acid such as (meth)acrylic acid. The structural unit derived from (c) is preferably one or more selected from (meth)acrylic acid esters having a linear or branched aliphatic saturated hydrocarbon group and (meth)acrylic acid esters having a cyclic saturated hydrocarbon group, more preferably two or more. Resin [K4'] may be produced by referring to the production method of resin [K4] described above, and the amount of (b) used is preferably 100 mol per 100 mol of (a).

[0252] In resin [K5], the ratio of structural units derived from each of them is as follows among all structural units constituting resin [K5]: Structural units derived from (b) (without (a) added): 0 to 30 mol% Structural units obtained by adding (a) to structural units derived from (b); 5 to 95 mol% Structural units derived from (c): 5 to 95 mol% It is preferred that Structural units derived from (b) (without (a) added): 0 to 10 mol% Structural units obtained by adding (a) to structural units derived from (b): 15 to 90 mol% Structural units derived from (c): 10 to 85 mol% It is more preferable that Structural units derived from (b) (without (a) added): 0 to 5 mol% Structural units obtained by adding (a) to structural units derived from (b); 20 to 80 mol% Structural units derived from (c): 20 to 80 mol% It is even more preferred that: The total of the structural units derived from (b) (without (a) added), the structural units obtained by adding (a) to the structural units derived from (b), and the structural units derived from (c) is, for example, 90 mol % or more, preferably 95 mol % or more, more preferably 98 mol % or more, and particularly preferably 100 mol % of all the structural units constituting the resin [K5].

[0253] As the structural unit derived from (b) (without (a)), a structural unit derived from a monomer (b1-1) having a structure in which a linear or branched aliphatic unsaturated hydrocarbon is epoxidized is preferred. As the structural unit in which (a) is added to a structural unit derived from (b), a structural unit in which an unsaturated monocarboxylic acid such as (meth)acrylic acid is added to a structural unit derived from a monomer (b1-1) having a structure in which a linear or branched aliphatic unsaturated hydrocarbon is epoxidized is preferred. As the structural unit derived from (c), one or more types selected from (meth)acrylic acid esters having a linear or branched aliphatic saturated hydrocarbon group and (meth)acrylic acid esters having a cyclic saturated hydrocarbon group are preferred, and two or more types are more preferred.

[0254] Resin [K5] is produced in the first step by the same method as the above-mentioned resin [K1] to obtain a copolymer of (b) and (c). As in the above, the obtained copolymer may be used as it is in the form of a solution after the reaction, or may be a concentrated or diluted solution, or may be extracted as a solid (powder) by a method such as reprecipitation. The ratios of the structural units derived from (b) and (c) to the total number of moles of all structural units constituting the copolymer are, respectively, Structural units derived from (b): 5 to 95 mol% Structural units derived from (c): 5 to 95 mol% It is preferred that Structural units derived from (b): 10 to 90 mol% Structural units derived from (c): 10 to 90 mol% It is more preferable that:

[0255] Furthermore, under the same conditions as in the manufacturing method of resin [K4] or resin [K4'], resin [K5] can be obtained by reacting a cyclic ether derived from (b) contained in a copolymer of (b) and (c) with a carboxylic acid or carboxylic acid anhydride contained in (a). The amount of (a) reacted with the copolymer is preferably 5 to 100 moles per 100 moles of (b). Because the reactivity of cyclic ethers is high and unreacted (b) is unlikely to remain, (b1) is preferred as (b) used in resin [K5], and (b1-1) is more preferred.

[0256] In the resin [K6], the ratio of structural units derived from each of them is as follows among all structural units constituting the resin [K6]: Structural units derived from (b) (without (a) added): 0 to 30 mol% A structural unit obtained by adding (a) to a structural unit derived from (b) (no carboxylic acid anhydride is added); 20 to 85 mol% A structural unit obtained by adding (a) to a structural unit derived from (b) and further adding a carboxylic acid anhydride thereto: 2 to 40 mol% Structural units derived from (c): 10 to 60 mol% It is preferred that Structural units derived from (b) (without (a) added): 0 to 10 mol% A structural unit in which (a) is added to a structural unit derived from (b) (no carboxylic anhydride is added); 40 to 80 mol% A structural unit obtained by adding (a) to a structural unit derived from (b) and further adding a carboxylic acid anhydride thereto: 3 to 30 mol% Structural units derived from (c): 15 to 50 mol% It is more preferable that Structural units derived from (b) (without (a) added): 0 to 5 mol% A structural unit obtained by adding (a) to a structural unit derived from (b) (no carboxylic anhydride is added); 50 to 70 mol% A structural unit obtained by adding (a) to a structural unit derived from (b) and further adding a carboxylic acid anhydride thereto: 5 to 20 mol% Structural units derived from (c): 20 to 40 mol% It is even more preferred that:

[0257] The total of the structural units derived from (b) (to which (a) is not added), the structural units obtained by adding (a) to the structural units derived from (b) (to which carboxylic acid anhydride is not added), the structural units obtained by adding (a) to the structural units derived from (b) and further adding a carboxylic acid anhydride, and the structural units derived from (c) is, for example, 90 mol % or more, preferably 95 mol % or more, more preferably 98 mol % or more, and particularly preferably 100 mol % of all the structural units constituting the resin [K6].

[0258] As the structural unit derived from (b) (without (a) added), a structural unit derived from a monomer (b1-1) having a structure in which a linear or branched aliphatic unsaturated hydrocarbon is epoxidized is preferred. As the structural unit in which (a) is added to a structural unit derived from (b) (without carboxylic anhydride added), a structural unit in which an unsaturated monocarboxylic acid such as (meth)acrylic acid is added to a structural unit derived from a monomer (b1-1) having a structure in which a linear or branched aliphatic unsaturated hydrocarbon is epoxidized is preferred. As the structural unit in which (a) is added to a structural unit derived from (b) and a carboxylic anhydride is further added, a structural unit in which an unsaturated monocarboxylic acid such as (meth)acrylic acid is added to a structural unit derived from a monomer (b1-1) having a structure in which a linear or branched aliphatic unsaturated hydrocarbon is epoxidized and a saturated aliphatic polycarboxylic anhydride such as succinic anhydride is further added. The structural unit derived from (c) is preferably one or more types selected from (meth)acrylic acid esters having a linear or branched aliphatic saturated hydrocarbon group and (meth)acrylic acid esters having a cyclic saturated hydrocarbon group, and more preferably two or more types.

[0259] Resin [K6] is produced in the first step by the same method as the above-mentioned resin [K1] to obtain a copolymer of (b) and (c). As in the above, the obtained copolymer may be used as it is in the form of a solution after the reaction, or may be a concentrated or diluted solution, or may be extracted as a solid (powder) by a method such as reprecipitation. The ratios of the structural units derived from (b) and (c) to the total number of moles of all structural units constituting the copolymer are, respectively, Structural units derived from (b): 5 to 95 mol% Structural units derived from (c): 5 to 95 mol% It is preferred that Structural units derived from (b): 10 to 90 mol% Structural units derived from (c): 10 to 90 mol% It is more preferable that:

[0260] Further, under the same conditions as in the production method of the resin [K4], the cyclic ether derived from (b) contained in the copolymer of (b) and (c) is reacted with the carboxylic acid or carboxylic anhydride contained in (a). The amount of (a) used is preferably 80 to 100 moles per 100 moles of (b).

[0261] The hydroxyl group generated by the reaction of the cyclic ether with the carboxylic acid or carboxylic anhydride contained in (a) is reacted with the carboxylic anhydride. The amount of the carboxylic anhydride used is preferably 0.05 to 1 mol, more preferably 0.10 to 0.8 mol, and even more preferably 0.13 to 0.7 mol, per mol of the amount of (a) used (in other words, per mol of the hydroxyl group generated by the use of (a)).

[0262] Specific examples of the resin (B) include 3,4-epoxycyclohexylmethyl(meth)acrylate / (meth)acrylic acid copolymer, 3,4-epoxytricyclo[5.2.1.0 2,6 ] Decyl acrylate / (meth)acrylic acid copolymer and other resins [K1]; Glycidyl (meth)acrylate / benzyl (meth)acrylate / (meth)acrylic acid copolymer, glycidyl (meth)acrylate / styrene / (meth)acrylic acid copolymer, 3,4-epoxytricyclo[5.2.1.0 2,6 ]decyl acrylate / (meth)acrylic acid / N-cyclohexylmaleimide copolymer, 3,4-epoxytricyclo[5.2.1.0 2,6 ]decyl acrylate / (meth)acrylic acid / N-cyclohexylmaleimide / 2-hydroxyethyl (meth)acrylate copolymer, 3,4-epoxytricyclo[5.2.1.0 2,6 ]Decyl acrylate / (meth)acrylic acid / N-cyclohexylmaleimide / Tricyclo[5.2.1.0 2,6 ]Decen-8-yl (meth)acrylate copolymer, 3,4-epoxytricyclo[5.2.1.0 2,6 ] Decyl acrylate / (meth)acrylic acid / benzyl (meth)acrylate copolymer, 3,4-epoxytricyclo[5.2.1.0 2,6 ] Decyl acrylate / (meth)acrylic acid / phenoxybenzyl (meth)acrylate copolymer, 3-methyl-3-(meth)acryloyloxymethyloxetane / (meth)acrylic acid / styrene copolymer, and other resins [K2]; Resins such as benzyl (meth)acrylate / (meth)acrylic acid copolymer, styrene / (meth)acrylic acid copolymer [K3]; Resins in which glycidyl (meth)acrylate is added to a portion of the carboxylic acid groups of a benzyl (meth)acrylate / (meth)acrylic acid copolymer, resins in which glycidyl (meth)acrylate is added to a portion of the carboxylic acid groups of a tricyclodecyl (meth)acrylate / styrene / (meth)acrylic acid copolymer, resins in which glycidyl (meth)acrylate is added to a portion of the carboxylic acid groups of a tricyclodecyl (meth)acrylate / benzyl (meth)acrylate / (meth)acrylic acid copolymer, resins in which glycidyl (meth)acrylate is added to a portion of the carboxylic acid groups of a norbornene / vinyl toluene / (meth)acrylic acid copolymer, resins in which glycidyl (meth)acrylate is added to a portion of the carboxylic acid groups of a norbornene / styrene / (meth)acrylic acid copolymer, and the like [K4]; Resins such as a resin obtained by reacting a copolymer of tricyclodecyl (meth)acrylate / (meth)acrylic acid with glycidyl (meth)acrylate, and a resin obtained by reacting a copolymer of tricyclodecyl (meth)acrylate / styrene / (meth)acrylic acid with glycidyl (meth)acrylate [K4']; Resins obtained by reacting a copolymer of tricyclodecyl (meth)acrylate / glycidyl (meth)acrylate with (meth)acrylic acid, and resins obtained by reacting a copolymer of tricyclodecyl (meth)acrylate / styrene / glycidyl (meth)acrylate with (meth)acrylic acid [K5]; Resins obtained by reacting a copolymer of tricyclodecyl (meth)acrylate / glycidyl (meth)acrylate with (meth)acrylic acid and further reacting the resulting resin with tetrahydrophthalic anhydride, resins obtained by reacting a copolymer of 2-ethylhexyl (meth)acrylate / tricyclodecyl (meth)acrylate / glycidyl (meth)acrylate with (meth)acrylic acid and further reacting the resulting resin with succinic anhydride, resins obtained by reacting a copolymer of 2-ethylhexyl (meth)acrylate / tricyclodecyl (meth)acrylate / glycidyl (meth)acrylate with (meth)acrylic acid and further reacting some of the hydroxyl groups with succinic anhydride, resins obtained by reacting a copolymer of methyl (meth)acrylate / 2-ethylhexyl (meth)acrylate / tricyclodecyl (meth)acrylate / glycidyl (meth)acrylate with (meth)acrylic acid and further reacting the resulting resin with succinic anhydride [K6], and the like.

[0263] Resins [K1] to [K6] may be used alone or in combination of two or more. Among them, resin (B) is preferably at least one selected from the group consisting of resin [K1] and resin [K2], and particularly preferably contains resin [K1].

[0264] The polystyrene-equivalent weight average molecular weight of the resin (B) is preferably from 3,000 to 100,000, more preferably from 5,000 to 50,000, and even more preferably from 5,000 to 30,000. When the molecular weight is within the above range, the hardness of the color filter is improved, the residual film rate is high, the solubility of the unexposed portion in the developer is good, and the resolution of the colored pattern tends to be improved.

[0265] The polydispersity of the resin (B) [weight average molecular weight (Mw) / number average molecular weight (Mn)] is preferably 1.1 or more and 6 or less, and more preferably 1.2 or more and 4 or less.

[0266] The acid value of the resin (B) is preferably 20 mg-KOH / g or more and 170 mg-KOH / g or less, more preferably 25 mg-KOH / g or more and 150 mg-KOH / g or less, and even more preferably 73 mg-KOH / g or more and 135 mg-KOH / g or less, calculated as a solid content. The acid value is a value measured as the amount (mg) of potassium hydroxide required to neutralize 1 g of the resin (B), and can be determined, for example, by titration with an aqueous potassium hydroxide solution.

[0267] The content of resin (B) is preferably 7% by mass or more and 85% by mass or less, more preferably 13% by mass or more and 80% by mass or less, and even more preferably 15% by mass or more and 70% by mass or less, based on the total amount of solids. When the content of resin (B) is within the above range, a colored pattern can be formed, and the resolution and residual film rate of the colored pattern tend to be improved.

[0268] <Polymerizable compound (C)> The polymerizable compound (C) is a compound that can be polymerized by active radicals and / or acids generated from the polymerization initiator (D), and examples thereof include compounds having a polymerizable ethylenically unsaturated bond, and are preferably (meth)acrylic acid ester compounds.

[0269] Among them, the polymerizable compound (C) is preferably a polymerizable compound having three or more ethylenically unsaturated bonds. Examples of such polymerizable compounds include trimethylolpropane tri(meth)acrylate, pentaerythritol tri(meth)acrylate, pentaerythritol tetra(meth)acrylate, dipentaerythritol penta(meth)acrylate, dipentaerythritol hexa(meth)acrylate, tripentaerythritol octa(meth)acrylate, tripentaerythritol hepta(meth)acrylate, tetrapentaerythritol deca(meth)acrylate, tetrapentaerythritol nona(meth)acrylate, tri ... Examples of the acrylates include 2-(2-(meth)acryloyloxyethyl)isocyanurate, ethylene glycol modified pentaerythritol tetra(meth)acrylate, ethylene glycol modified dipentaerythritol hexa(meth)acrylate, propylene glycol modified pentaerythritol tetra(meth)acrylate, propylene glycol modified dipentaerythritol hexa(meth)acrylate, caprolactone modified pentaerythritol tetra(meth)acrylate, and caprolactone modified dipentaerythritol hexa(meth)acrylate. Among these, at least one selected from the group consisting of dipentaerythritol penta(meth)acrylate and dipentaerythritol hexa(meth)acrylate is preferred.

[0270] The weight average molecular weight of the polymerizable compound (C) is preferably 150 or more and 2,900 or less, and more preferably 250 or more and 1,500 or less.

[0271] The content of the polymerizable compound (C) is preferably 5% by mass or more and 75% by mass or less, more preferably 7% by mass or more and 70% by mass or less, and even more preferably 15% by mass or more and 70% by mass or less, based on the total amount of solids. When the content of the polymerizable compound (C) is within the above range, the residual film rate during color pattern formation and the chemical resistance of the color filter tend to be improved.

[0272] <Polymerization initiator (D)> The polymerization initiator (D) is not particularly limited as long as it is a compound that can generate active radicals, acids, etc. by the action of light or heat and initiate polymerization, and known polymerization initiators can be used. Examples of polymerization initiators that generate active radicals include alkylphenone compounds, triazine compounds, acylphosphine oxide compounds, O-acyloxime compounds, and biimidazole compounds.

[0273] The O-acyloxime compound is a compound having a partial structure represented by formula (d1): In the following, * represents a bond.

[0274] [ka]

[0275] Examples of the O-acyloxime compound include N-benzoyloxy-1-(4-phenylsulfanylphenyl)butan-1-one-2-imine, N-benzoyloxy-1-(4-phenylsulfanylphenyl)octan-1-one-2-imine, N-benzoyloxy-1-(4-phenylsulfanylphenyl)-3-cyclopentylpropan-1-one-2-imine, N-acetoxy-1-[9-ethyl-6-(2-methylbenzoyl)-9H-carbazol-3-yl]ethan-1-imine, N-acetoxy-1-[9-ethyl-6-{2-methyl-4-(3,3-dimethylphenyl)-1,2-diphenyl-2,3-diphenyl-2,4-diphenyl-2,5-diphenyl-2,6-diphenyl-2,7-diphenyl-2,7-diphenyl-2,8-diphenyl-2,9-diphenyl-2,8-diphenyl-2,9-diphenyl-2,7-diphenyl-2,8-diphenyl-2,9 ... Examples of the methyl-2,4-dioxacyclopentanylmethyloxy)benzoyl}-9H-carbazol-3-yl]ethane-1-imine, N-acetoxy-1-[9-ethyl-6-(2-methylbenzoyl)-9H-carbazol-3-yl]-3-cyclopentylpropan-1-imine, N-benzoyloxy-1-[9-ethyl-6-(2-methylbenzoyl)-9H-carbazol-3-yl]-3-cyclopentylpropan-1-one-2-imine, N-acetyloxy-1-(4-phenylsulfanylphenyl)-3-cyclohexylpropan-1-one-2-imine, etc. Commercially available products such as Irgacure (registered trademark) OXE01, OXE02 (all manufactured by BASF), N-1919 (manufactured by ADEKA), and PBG-327 (manufactured by Changzhou Strong Electronic New Materials Co., Ltd.) may also be used. Among them, the O-acyloxime compound is preferably at least one selected from the group consisting of N-benzoyloxy-1-(4-phenylsulfanylphenyl)butan-1-one-2-imine, N-benzoyloxy-1-(4-phenylsulfanylphenyl)octan-1-one-2-imine, N-acetyloxy-1-(4-phenylsulfanylphenyl)-3-cyclohexylpropan-1-one-2-imine, and N-benzoyloxy-1-(4-phenylsulfanylphenyl)-3-cyclopentylpropan-1-one-2-imine, and more preferably N-benzoyloxy-1-(4-phenylsulfanylphenyl)octan-1-one-2-imine and N-acetyloxy-1-(4-phenylsulfanylphenyl)-3-cyclohexylpropan-1-one-2-imine.These O-acyloxime compounds tend to give color filters with high brightness.

[0276] The alkylphenone compound is preferably a compound having a partial structure represented by formula (d2) or a partial structure represented by formula (d3). In these partial structures, the benzene ring may have a substituent.

[0277] [ka]

[0278] Examples of the compound having a partial structure represented by formula (d2) include 2-methyl-2-morpholino-1-(4-methylsulfanylphenyl)propan-1-one, 2-dimethylamino-1-(4-morpholinophenyl)-2-benzylbutan-1-one, 2-(dimethylamino)-2-[(4-methylphenyl)methyl]-1-[4-(4-morpholinyl)phenyl]butan-1-one, etc. Commercially available products such as Irgacure (registered trademark) 369, 907, and 379 (all manufactured by BASF) may also be used. Examples of compounds having a partial structure represented by formula (d3) include 2-hydroxy-2-methyl-1-phenylpropan-1-one, 2-hydroxy-2-methyl-1-[4-(2-hydroxyethoxy)phenyl]propan-1-one, 1-hydroxycyclohexyl phenyl ketone, oligomers of 2-hydroxy-2-methyl-1-(4-isopropenylphenyl)propan-1-one, α,α-diethoxyacetophenone, and benzyl dimethyl ketal. In terms of sensitivity, the alkylphenone compound is preferably a compound having a partial structure represented by formula (d2).

[0279] Examples of the triazine compound include 2,4-bis(trichloromethyl)-6-(4-methoxyphenyl)-1,3,5-triazine, 2,4-bis(trichloromethyl)-6-(4-methoxynaphthyl)-1,3,5-triazine, 2,4-bis(trichloromethyl)-6-piperonyl-1,3,5-triazine, 2,4-bis(trichloromethyl)-6-(4-methoxystyryl)-1,3,5-triazine, and 2,4-bis(trichloromethyl)-6-[ 2-(5-methylfuran-2-yl)ethenyl]-1,3,5-triazine, 2,4-bis(trichloromethyl)-6-[2-(furan-2-yl)ethenyl]-1,3,5-triazine, 2,4-bis(trichloromethyl)-6-[2-(4-diethylamino-2-methylphenyl)ethenyl]-1,3,5-triazine, 2,4-bis(trichloromethyl)-6-[2-(3,4-dimethoxyphenyl)ethenyl]-1,3,5-triazine, and the like.

[0280] The acylphosphine oxide compound may be 2,4,6-trimethylbenzoyldiphenylphosphine oxide, etc. Commercially available products such as Irgacure (registered trademark) 819 (manufactured by BASF) may also be used.

[0281] Examples of the biimidazole compound include 2,2'-bis(2-chlorophenyl)-4,4',5,5'-tetraphenylbiimidazole, 2,2'-bis(2,3-dichlorophenyl)-4,4',5,5'-tetraphenylbiimidazole (see, for example, JP-A-6-75372 and JP-A-6-75373), 2,2'-bis(2-chlorophenyl)-4,4',5,5'-tetra(alkoxyphenyl)biimidazole, and 2,2'-bis(2- 2,2'-bis(2-chlorophenyl)-4,4',5,5'-tetra(dialkoxyphenyl)biimidazole, 2,2'-bis(2-chlorophenyl)-4,4',5,5'-tetra(trialkoxyphenyl)biimidazole (see, for example, JP-B-48-38403 and JP-A-62-174204), and imidazole compounds in which the phenyl groups at the 4,4',5,5'-positions are substituted with carboalkoxy groups (see, for example, JP-A-7-10913).

[0282] Further, examples of the polymerization initiator (D) include benzoin compounds such as benzoin, benzoin methyl ether, benzoin ethyl ether, benzoin isopropyl ether, and benzoin isobutyl ether; benzophenone compounds such as benzophenone, o-benzoyl methyl benzoate, 4-phenylbenzophenone, 4-benzoyl-4'-methyldiphenyl sulfide, 3,3',4,4'-tetra(tert-butylperoxycarbonyl)benzophenone, and 2,4,6-trimethylbenzophenone; quinone compounds such as 9,10-phenanthrenequinone, 2-ethylanthraquinone, and camphorquinone; 10-butyl-2-chloroacridone, benzyl, methyl phenylglyoxylate, and titanocene compounds. These are preferably used in combination with the polymerization initiator aid (D1) (especially amines) described below.

[0283] Examples of the acid generator include onium salts such as 4-hydroxyphenyl dimethylsulfonium p-toluenesulfonate, 4-hydroxyphenyl dimethylsulfonium hexafluoroantimonate, 4-acetoxyphenyl dimethylsulfonium p-toluenesulfonate, 4-acetoxyphenyl methyl benzylsulfonium hexafluoroantimonate, triphenylsulfonium p-toluenesulfonate, triphenylsulfonium hexafluoroantimonate, diphenyliodonium p-toluenesulfonate, and diphenyliodonium hexafluoroantimonate; nitrobenzyl tosylates; and benzoin tosylates.

[0284] The polymerization initiator (D) is preferably a polymerization initiator containing at least one selected from the group consisting of an alkylphenone compound, a triazine compound, an acylphosphine oxide compound, an O-acyloxime compound, and a biimidazole compound, and more preferably a polymerization initiator containing an O-acyloxime compound.

[0285] The content of the polymerization initiator (D) is preferably 0.1 to 30 parts by mass, more preferably 1 to 20 parts by mass, based on 100 parts by mass of the total amount of the resin (B) and the polymerizable compound (C). When the content of the polymerization initiator (D) is within the above range, the sensitivity is increased and the exposure time tends to be shortened, thereby improving the productivity of the color filter.

[0286] <Polymerization initiator aid (D1)> The polymerization initiation aid (D1) is a compound used to promote the polymerization of a polymerizable compound whose polymerization has been initiated by a polymerization initiator, or a sensitizer. When the polymerization initiation aid (D1) is contained, it is usually used in combination with the polymerization initiator (D). Examples of the polymerization initiator aid (D1) include amine compounds, alkoxyanthracene compounds, thioxanthone compounds, and carboxylic acid compounds.

[0287] Examples of the amine compound include triethanolamine, methyldiethanolamine, triisopropanolamine, methyl 4-dimethylaminobenzoate, ethyl 4-dimethylaminobenzoate, isoamyl 4-dimethylaminobenzoate, 2-dimethylaminoethyl benzoate, 2-ethylhexyl 4-dimethylaminobenzoate, N,N-dimethyl-p-toluidine, 4,4'-bis(dimethylamino)benzophenone (commonly known as Michler's ketone), 4,4'-bis(diethylamino)benzophenone, 4,4'-bis(ethylmethylamino)benzophenone, etc., and among these, 4,4'-bis(diethylamino)benzophenone is preferred. Commercially available products such as EAB-F (manufactured by Hodogaya Chemical Co., Ltd.) may also be used.

[0288] Examples of the alkoxyanthracene compound include 9,10-dimethoxyanthracene, 2-ethyl-9,10-dimethoxyanthracene, 9,10-diethoxyanthracene, 2-ethyl-9,10-diethoxyanthracene, 9,10-dibutoxyanthracene, and 2-ethyl-9,10-dibutoxyanthracene.

[0289] Examples of the thioxanthone compound include 2-isopropylthioxanthone, 4-isopropylthioxanthone, 2,4-diethylthioxanthone, 2,4-dichlorothioxanthone, and 1-chloro-4-propoxythioxanthone.

[0290] Examples of the carboxylic acid compound include phenylsulfanylacetic acid, methylphenylsulfanylacetic acid, ethylphenylsulfanylacetic acid, methylethylphenylsulfanylacetic acid, dimethylphenylsulfanylacetic acid, methoxyphenylsulfanylacetic acid, dimethoxyphenylsulfanylacetic acid, chlorophenylsulfanylacetic acid, dichlorophenylsulfanylacetic acid, N-phenylglycine, phenoxyacetic acid, naphthylthioacetic acid, N-naphthylglycine, and naphthoxyacetic acid.

[0291] When these polymerization initiation aids (D1) are used, the content thereof is preferably 0.1 to 30 parts by mass, more preferably 1 to 20 parts by mass, based on 100 parts by mass of the total amount of the resin (B) and the polymerizable compound (C). When the amount of the polymerization initiation aid (D1) is within this range, a colored pattern can be formed with higher sensitivity, and the productivity of the color filter tends to improve.

[0292] <Solvent (E)> The solvent (E) is not particularly limited, and a solvent commonly used in the field can be used. For example, ester solvent (solvent containing -COO- in the molecule and not containing -O-), ether solvent (solvent containing -O- in the molecule and not containing -COO-), ether ester solvent (solvent containing -COO- and -O- in the molecule), ketone solvent (solvent containing -CO- in the molecule and not containing -COO-), alcohol solvent (solvent containing -OH in the molecule and not containing -O-, -CO-, and -COO-), aromatic hydrocarbon solvent, amide solvent, dimethyl sulfoxide, etc. can be mentioned.

[0293] Specific examples of the ester solvent include the same solvents as those exemplified as the ester solvent in the above solvent (Z).

[0294] Specific examples of the ether solvent include the same solvents as those exemplified as the ether solvent in the above solvent (Z).

[0295] Specific examples of the ether ester solvent include the same solvents as those exemplified as the ether ester solvent in the above solvent (Z).

[0296] Specific examples of the ketone solvent include the same solvents as those exemplified as the ketone solvent in the above solvent (Z).

[0297] Specific examples of the alcohol solvent include the same solvents as those exemplified as the alcohol solvent in the above solvent (Z).

[0298] Specific examples of the aromatic hydrocarbon solvent include the same solvents as those exemplified as the aromatic hydrocarbon solvent in the above solvent (Z).

[0299] Specific examples of the amide solvent include the same solvents as those exemplified as the amide solvent in the above solvent (Z).

[0300] Among the above solvents, from the viewpoint of coatability and drying property, preferred is an organic solvent having a boiling point at 1 atm of 120° C. or more and 180° C. or less. As the solvent (E), preferred is a solvent containing at least one selected from the group consisting of propylene glycol monomethyl ether acetate, ethyl lactate, propylene glycol monomethyl ether, ethyl 3-ethoxypropionate, ethylene glycol monomethyl ether, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, 4-hydroxy-4-methyl-2-pentanone, and N,N-dimethylformamide, and more preferred is a solvent containing at least one selected from the group consisting of propylene glycol monomethyl ether acetate, propylene glycol monomethyl ether, ethyl lactate, ethyl 3-ethoxypropionate, and 4-hydroxy-4-methyl-2-pentanone.

[0301] The content of the solvent (E) is preferably 55% by mass or more and 95% by mass or less, more preferably 60% by mass or more and 92% by mass or less, based on the total amount of the colored curable resin composition of the present invention. In other words, the total content of the solid content of the colored curable resin composition is preferably 5% by mass or more and 45% by mass or less, more preferably 8% by mass or more and 40% by mass or less. When the content of the solvent (E) is within the above range, the flatness during application is good, and the color density is not insufficient when a color filter is formed, so that the display characteristics tend to be good.

[0302] <Leveling agent (F)> Examples of the leveling agent (F) include silicone surfactants, fluorine surfactants, and silicone surfactants having fluorine atoms, which may have a polymerizable group in the side chain.

[0303] Examples of silicone surfactants include surfactants having a siloxane bond in the molecule.Specific examples include Toray Silicone DC3PA, SH7PA, DC11PA, SH21PA, SH28PA, SH29PA, SH30PA, and SH8400 (trade name: manufactured by Toray Dow Corning Co., Ltd.), KP321, KP322, KP323, KP324, KP326, KP340, and KP341 (manufactured by Shin-Etsu Chemical Co., Ltd.), TSF400, TSF401, TSF410, TSF4300, TSF4440, TSF4445, TSF4446, TSF4452, and TSF4460 (manufactured by Momentive Performance Materials Japan LLC).

[0304] The fluorine-based surfactant may include surfactants having a fluorocarbon chain in the molecule.Specific examples include Fluorad (registered trademark) FC430, FC431 (manufactured by Sumitomo 3M Limited), Megafac (registered trademark) F142D, F171, F172, F173, F177, F183, F554, R30, RS-718-K (manufactured by DIC Corporation), F-top (registered trademark) EF301, EF303, EF351, EF352 (manufactured by Mitsubishi Materials Electronic Chemicals Co., Ltd.), Surflon (registered trademark) S381, S382, SC101, SC105 (manufactured by Asahi Glass Co., Ltd.), and E5844 (manufactured by Daikin Fine Chemicals Research Institute Co., Ltd.).

[0305] Examples of the silicone surfactant having a fluorine atom include surfactants having a siloxane bond and a fluorocarbon chain in the molecule, such as Megafac (registered trademark) R08, BL20, F475, F477, and F443 (manufactured by DIC Corporation).

[0306] The content of the leveling agent (F) is preferably 0.00001% by mass or more and 0.2% by mass or less, more preferably 0.00005% by mass or more and 0.1% by mass or less, and even more preferably 0.0001% by mass or more and 0.05% by mass or less, based on the total amount of the colored curable resin composition. Note that this content does not include the content of the dispersant. When the content of the leveling agent (F) is within the above range, the flatness of the color filter can be improved.

[0307] <Other ingredients> The colored curable resin composition of the present invention may contain additives known in the technical field, such as a filler, another polymer compound, an adhesion promoter, an antioxidant, a light stabilizer, and a chain transfer agent, as necessary.

[0308] <Method for producing colored curable resin composition> The colored curable resin composition of the present invention can be prepared, for example, by mixing the azo dye (Aa), the resin (B), the polymerizable compound (C), the polymerization initiator (D), and the solvent (E), as well as the dye (A1-1), the pigment (A1-2), the leveling agent (F), and other components that are used as necessary. The mixing can be performed using known or conventional equipment and conditions.

[0309] The colorant (A1) may be mixed in advance with a part or all of the solvent (E) and dispersed using a bead mill or the like until the average particle size is about 0.2 μm or less. In this case, the dispersant and a part or all of the resin (B) may be mixed as necessary. It is preferable to prepare the desired colored curable resin composition by mixing the remaining components to the dispersion thus obtained to a predetermined concentration. When using a bead mill, the diameter of the beads is preferably 0.05 mm or more and 0.5 mm or less, and the material of the beads may be glass, ceramic, metal, etc.

[0310] <Manufacturing method of color filters> Examples of methods for producing a colored pattern of a color filter from the colored curable resin composition of the present invention include a photolithography method, an inkjet method, and a printing method. Among these, the photolithography method is preferred. The photolithography method is a method in which the colored curable resin composition is applied to a substrate, dried to form a composition layer, and the composition layer is exposed through a photomask and developed. In the photolithography method, a colored coating film, which is a cured product of the composition layer, can be formed by not using a photomask during exposure and / or not developing.

[0311] The thickness of the color filter (cured film) is not particularly limited and can be appropriately adjusted depending on the purpose or use, and is, for example, 0.1 μm or more and 30 μm or less, preferably 0.1 μm or more and 20 μm or less, and more preferably 0.5 μm or more and 6 μm or less.

[0312] The substrate may be a glass plate such as quartz glass, borosilicate glass, alumina silicate glass, or soda lime glass with a silica-coated surface, a resin plate such as polycarbonate, polymethylmethacrylate, or polyethylene terephthalate, silicon, or a substrate having a thin film of aluminum, silver, or a silver / copper / palladium alloy formed thereon. On these substrates, another color filter layer, a resin layer, a transistor, a circuit, or the like may be formed. A silicon substrate having an HMDS treatment may also be used.

[0313] Formation of each color pixel by photolithography can be performed with known or conventional equipment and conditions. For example, it can be produced as follows. First, a colored curable resin composition is applied onto a substrate, and volatile components such as a solvent are removed by heating and drying (pre-baking) and / or drying under reduced pressure to obtain a smooth composition layer. Examples of the application method include spin coating, slit coating, and slit and spin coating. The temperature when drying by heating is preferably 30° C. or more and 120° C. or less, more preferably 50° C. or more and 110° C. or less. The heating time is preferably 10 seconds or more and 60 minutes or less, more preferably 30 seconds or more and 30 minutes or less. When drying under reduced pressure, it is preferably performed under a pressure of 50 to 150 Pa at a temperature range of 20 to 25° C. The film thickness of the composition layer is not particularly limited and may be appropriately selected according to the film thickness of the desired color filter.

[0314] Next, the composition layer is exposed through a photomask for forming a desired colored pattern. The pattern on the photomask is not particularly limited, and a pattern according to the intended use is used. As the light source used for exposure, a light source that generates light with a wavelength of 250 to 450 nm is preferable. For example, light less than 350 nm may be cut using a filter that cuts this wavelength range, or light near 436 nm, near 408 nm, and near 365 nm may be selectively extracted using a bandpass filter that extracts these wavelength ranges. Specific examples include mercury lamps, light-emitting diodes, metal halide lamps, halogen lamps, and the like. It is preferable to use a mask aligner, a reduction projection exposure device such as a stepper, or a proximity exposure device, since it is possible to uniformly irradiate the entire exposure surface with parallel light rays and to accurately align the photomask and the substrate.

[0315] The composition layer after exposure is brought into contact with a developer for development, thereby forming a colored pattern on the substrate. The unexposed portion of the composition layer is dissolved in the developer and removed by development. The developer is preferably an aqueous solution of an alkaline compound such as potassium hydroxide, sodium bicarbonate, sodium carbonate, or tetramethylammonium hydroxide. The concentration of these alkaline compounds in the aqueous solution is preferably 0.01% by mass or more and 10% by mass or less, more preferably 0.03% by mass or more and 5% by mass or less. Furthermore, the developer may contain a surfactant. The development method may be any of a paddle method, a dipping method, and a spray method. Furthermore, the substrate may be tilted at any angle during development. After development, it is preferable to wash with water.

[0316] Furthermore, it is preferable to perform post-baking on the obtained colored pattern. The post-baking temperature is preferably from 80° C. to 250° C., and more preferably from 100° C. to 245° C. The post-baking time is preferably from 1 minute to 120 minutes, and more preferably from 2 minutes to 30 minutes.

[0317] The colored pattern and colored coating film thus obtained are useful as color filters, and the color filters are useful as color filters for use in display devices (e.g., liquid crystal display devices, organic EL devices, etc.), electronic paper, solid-state imaging devices, etc. EXAMPLES

[0318] The present invention will be described in more detail below with reference to examples, but the present invention is not limited to the following examples, and can be modified as long as it satisfies the spirit of the invention, and all such modifications are included in the technical scope of the present invention. In the following, unless otherwise specified, "parts" means "parts by mass" and "%" means "% by mass".

[0319] The chemical structures of the compounds were confirmed by mass spectrometry (LC; Agilent 1200 model, MASS; Agilent LC / MSD6130 model).

[0320] The crystal structure of the azo dye was identified by powder X-ray measurement. The conditions of the powder X-ray measurement were as follows. Aluminum oxide, which is an internal standard substance, was added at a ratio of 50 parts to 50 parts of the azo dye and mixed. Aluminum oxide manufactured by Fujifilm Wako Pure Chemical Industries, Ltd. was used as the aluminum oxide. The difference spectrum between the obtained X-ray diffraction spectrum and the X-ray diffraction spectrum of the glass sample plate alone was calculated. Furthermore, since the thickness of the sample depends on the intensity of the X-ray diffraction spectrum, each peak intensity was obtained from the X-ray diffraction spectrum normalized with the peak intensity I3 of aluminum oxide, which is an internal standard substance, set to 100,000. Equipment: RINT2000, Rigaku Internal standard: Aluminum oxide X-ray: Cu-Kα ray Device Control: Concentration Method Measurement angle: 5~50° Voltage: 40kV Current: 40mA

[0321] The polystyrene-equivalent weight average molecular weight (Mw) and number average molecular weight (Mn) of the resin were measured by GPC (gel permeation chromatography) under the following conditions. Equipment: HLC-8120GPC (Tosoh Corporation) Column: TSK-GELG2000HXL Column temperature: 40℃ Solvent: Tetrahydrofuran Flow rate: 1.0mL / min Solid concentration of the analytical sample: 0.001 to 0.01% by mass Injection volume: 50μL Detector: RI Calibration standard material: TSK STANDARD POLYSTYRENE F-40, F-4, F-288, A-2500, A-500 (manufactured by Tosoh Corporation) The ratio of the weight average molecular weight and the number average molecular weight (Mw / Mn) calculated in terms of polystyrene obtained above was taken as the dispersity.

[0322] <Synthesis Example 1> 2.0 parts of 3-amino-4-methoxybenzanilide was added with 33 parts of water and 3.3 parts of 35% hydrochloric acid and stirred. Under ice cooling, an aqueous solution of 0.7 parts of sodium nitrite dissolved in 1.8 parts of water was added to the reaction solution and stirred for 2 hours to obtain a suspension containing a diazonium salt. Meanwhile, 10 parts of acetic acid, 10 parts of water, and 55 parts of methanol were added to 30 parts of 3-methyl-1-phenyl-5-pyrazolone, and then 19 parts of 25% aqueous sodium hydroxide solution was added and stirred under ice cooling. The suspension containing the diazonium salt was added dropwise to this. After the dropwise addition was completed, the mixture was further stirred at room temperature for 1 hour to obtain a yellow suspension. The yellow solid obtained by filtration was dried at 60°C under reduced pressure to obtain 2.2 parts of azo dye (1-1) consisting of a compound represented by formula (AI-1) (yield 64%). MS (ESI) m / z=427.8[M] + The X-ray diffraction spectrum of the azo dye (1-1) is shown in FIG. 2, and the X-ray diffraction parameters are shown in Table 6. In the X-ray diffraction spectrum in FIG. 2, the peaks at diffraction angles (2θ±0.2°)=25.5, 35.1, 37.8, 43.3, and 43.4° are peaks derived from aluminum oxide, which is an internal standard substance (the same applies to FIGS. 1 and 3 to 10). Also, FIG. 2 shows a difference spectrum between the azo dye and the glass sample plate, and is normalized with the peak intensity at a diffraction angle (2θ±0.2°)=35.1° derived from aluminum oxide, which is an internal standard substance, set to 100,000 (the same applies to FIGS. 1 and 3 to 10).

[0323] [ka]

[0324] <Example 1> 0.5 parts of the azo dye (1-1) obtained in Synthesis Example 1, 3.0 parts of N-methylpyrrolidone, and 10.5 parts of xylene were mixed, and the mixture in a slurry state was stirred for 3 hours at an internal temperature of 125° C. After cooling to room temperature, the mixture was filtered, and the resulting residue was dried under reduced pressure at 60° C. to obtain 0.39 parts of azo dye (1) consisting of a compound represented by formula (AI-1) (yield 78%). The X-ray diffraction spectrum of the azo dye (1) is shown in FIG. 1, and the X-ray diffraction parameters are shown in Table 6.

[0325] <Synthesis Example 2> 24 parts of acetic acid, 81 parts of water, and 8.2 parts of 35% hydrochloric acid were added to 4.4 parts of 4,4'-diaminobenzophenone and stirred. An aqueous solution of 3.6 parts of sodium nitrite dissolved in 5.3 parts of water was added to the reaction solution under ice cooling and stirred for 2 hours to obtain a suspension containing a diazonium salt. Meanwhile, 132 parts of methanol was added to 7.2 parts of 3-methyl-1-phenyl-5-pyrazolone, and then 69 parts of a 25% aqueous sodium hydroxide solution was added under ice cooling and stirred. The suspension containing the diazonium salt was added dropwise to this. After the dropwise addition was completed, the mixture was further stirred at room temperature for 1 hour to obtain a yellow suspension. The yellow solid obtained by filtration was dried at 60°C under reduced pressure to obtain 10 parts of azo dye (2-1) consisting of a compound represented by formula (AI-274) (yield 86%). MS (ESI) m / z = 581.0 [MH] - The X-ray diffraction spectrum of the azo dye (2-1) is shown in FIG. 4, and the X-ray diffraction parameters are shown in Table 6.

[0326] [ka]

[0327] <Example 2> 0.9 parts of the azo dye (2-1) obtained in Synthesis Example 2 and 24 parts of xylene were mixed, and the mixture in a slurry state was stirred at an internal temperature of 125° C. for 3 hours. After cooling to room temperature, 21 parts of methanol were added dropwise and stirred for 1 hour. The resulting mixture was filtered, and the resulting residue was dried under reduced pressure at 60° C. to obtain 0.8 parts of azo dye (2) consisting of a compound represented by formula (AI-274) (yield 89%). The X-ray diffraction spectrum of the azo dye (2) is shown in FIG. 3, and the X-ray diffraction parameters are shown in Table 6.

[0328] <Synthesis Example 3> 1.0 part of 4,4'-diaminodiphenyl ether was added with 20 parts of water and 2.0 parts of 35% hydrochloric acid and stirred. Under ice cooling, an aqueous solution of 0.9 parts of sodium nitrite dissolved in 1.1 parts of water was added to the reaction solution and stirred for 2 hours to obtain a suspension containing a diazonium salt. Meanwhile, 34 parts of methanol, 6.0 parts of acetic acid, and 6.5 parts of water were added to 1.8 parts of 3-methyl-1-phenyl-5-pyrazolone, and then 12 parts of 25% aqueous sodium hydroxide solution were added and stirred under ice cooling. The suspension containing the diazonium salt was added dropwise to this. After the dropwise addition was completed, the mixture was further stirred at room temperature for 1 hour to obtain a yellow suspension. The yellow solid obtained by filtration was dried at 60°C under reduced pressure to obtain 2.9 parts of azo dye (3-1) consisting of a compound represented by formula (AI-169) (yield 98%). MS (ESI) m / z=569.2[MH] - The X-ray diffraction spectrum of the azo dye (3-1) is shown in FIG. 6, and the X-ray diffraction parameters are shown in Table 6.

[0329] [ka]

[0330] <Example 3> 0.5 parts of the azo dye (3-1) obtained in Synthesis Example 3, 3.0 parts of N-methylpyrrolidone, and 10.5 parts of xylene were mixed, and the mixture in a slurry state was stirred at an internal temperature of 125° C. for 3 hours. After cooling to room temperature, 5 parts of acetonitrile were added dropwise and stirred for 1 hour. The resulting mixture was filtered, and the resulting residue was dried under reduced pressure at 60° C. to obtain 0.4 parts of the azo dye (3) consisting of a compound represented by formula (AI-169) (yield 71%). The X-ray diffraction spectrum of the azo dye (3) is shown in FIG. 5, and the X-ray diffraction parameters are shown in Table 6.

[0331] <Synthesis Example 4> 2.0 parts of 2,5-dichloro-4-nitroaniline were added with 20 parts of water, 8.0 parts of methanol, 2.0 parts of acetic acid, and 5.0 parts of 98% sulfuric acid, and the mixture was stirred. Under ice cooling, an aqueous solution of 1.2 parts of sodium nitrite dissolved in 1.8 parts of water was added to the reaction solution, and the mixture was stirred for 2 hours to obtain a suspension containing a diazonium salt. Meanwhile, 11 parts of methanol were added to 1.8 parts of 3-cyano-1-butyl-6-hydroxy-4-methyl-2-pyridone, and then 14 parts of a 25% aqueous sodium hydroxide solution were added under ice cooling and stirred. The suspension containing the diazonium salt was added dropwise to the mixture. After the dropwise addition, the mixture was further stirred at room temperature for 1 hour to obtain an orange suspension. The orange solid obtained by filtration was dried at 60° C. under reduced pressure to obtain a compound represented by formula (b).

[0332] [ka]

[0333] Next, 39 parts of water, 8.0 parts of methanol, 1.6 parts of sodium hydrogen carbonate, and 4.7 parts of sodium sulfide nonahydrate were added to 4.1 parts of the compound represented by formula (b), and the mixture was stirred at 85° C. for 2 hours. After cooling the reaction solution to room temperature, the reaction solution was neutralized to pH 6 with 35% hydrochloric acid, and the precipitated solid was collected by filtration. The solid obtained was washed with water, and the red solid obtained by filtration was dried at 60° C. under reduced pressure to obtain the compound represented by formula (c).

[0334] [ka]

[0335] Next, 16 parts of water, 3.8 parts of acetic acid, and 19 parts of 98% sulfuric acid were added to 3.8 parts of the compound represented by formula (c) and stirred. Under ice cooling, an aqueous solution in which 2.0 parts of sodium nitrite was dissolved in 3.0 parts of water was added to the reaction solution and stirred for 2 hours to obtain a suspension containing a diazonium salt. Meanwhile, 11 parts of methanol was added to 1.4 parts of 3-cyano-1-butyl-6-hydroxy-4-methyl-2-pyridone, and then 54 parts of a 25% aqueous sodium hydroxide solution was added under ice cooling and stirred. The suspension containing the diazonium salt was added dropwise to this. After the dropwise addition was completed, the mixture was further stirred at room temperature for 1 hour to obtain a red suspension. The red solid obtained by filtration was dispersed and washed with water and methanol for 30 minutes each, then filtered and dried at 60°C under reduced pressure to obtain 3.9 parts of azo dye (4-1) consisting of a compound represented by formula (AI-22) (yield 66%). MS (ESI) m / z=609.2[MH] - The X-ray diffraction spectrum of the azo dye (4-1) is shown in FIG. 8, and the X-ray diffraction parameters are shown in Table 6.

[0336] [ka]

[0337] <Example 4> 0.5 parts of the azo dye (4-1) obtained in Synthesis Example 4, 3.0 parts of N-methylpyrrolidone, and 10.5 parts of xylene were mixed, and the mixture in a slurry state was stirred for 3 hours at an internal temperature of 125° C. After cooling to room temperature, the mixture was filtered, and the resulting residue was dried under reduced pressure at 60° C. to obtain 0.4 parts of the azo dye (4) composed of a compound represented by formula (AI-22) (yield 75%). The X-ray diffraction spectrum of the azo dye (4) is shown in FIG. 7, and the X-ray diffraction parameters are shown in Table 6.

[0338] <Synthesis Example 5> 90 parts of methanol, 60 parts of acetic acid, 194 parts of 35% hydrochloric acid, and 150 parts of water were added to 30 parts of 2,5-dichloro-1,4-phenylenediamine and stirred. An aqueous solution of 14 parts of sodium nitrite dissolved in 21 parts of water was added to the reaction solution under ice cooling and stirred for 2 hours to obtain a suspension containing a diazonium salt. Meanwhile, 105 parts of methanol was added to 30 parts of 3-methyl-1-phenyl-5-pyrazolone, and then 412 parts of a 25% aqueous sodium hydroxide solution was added under ice cooling and stirred. The suspension containing the diazonium salt was added dropwise to this. After the dropwise addition, the mixture was further stirred at room temperature for 1 hour to obtain an orange suspension. The orange solid obtained by filtration was dried at 60°C under reduced pressure to obtain a compound represented by formula (d).

[0339] [ka]

[0340] Next, 20 parts of water, 6.7 parts of acetic acid, and 3.3 parts of 98% sulfuric acid were added to 2.1 parts of the compound represented by formula (d) and stirred. An aqueous solution of 0.6 parts of sodium nitrite dissolved in 3.3 parts of water was added to the reaction solution under ice cooling and stirred for 2 hours to obtain a suspension containing a diazonium salt. Meanwhile, 0.8 parts of methanol was added to 3-methyl-1-phenyl-5-pyrazolone, and then 15 parts of a 25% aqueous sodium hydroxide solution was added under ice cooling and stirred. The suspension containing the diazonium salt was added dropwise to this. After the dropwise addition was completed, the mixture was further stirred at room temperature for 1 hour to obtain a red suspension. The red solid obtained by filtration was dispersed and washed with water and methanol for 30 minutes each, then filtered and dried at 60°C under reduced pressure to obtain 0.8 parts of azo dye (5-1) consisting of a compound represented by formula (AI-19) (yield 53%). MS (ESI) m / z=545.0[MH] - The X-ray diffraction spectrum of the azo dye (5-1) is shown in FIG. 14, and the X-ray diffraction parameters are shown in Table 6.

[0341] [ka]

[0342] <Synthesis Example 6> 10 parts of the azo dye (5-1) obtained in Synthesis Example 5, 23 parts of tetramethylammonium hydroxide (25% aqueous solution), and 70 parts of methanol were mixed and stirred at room temperature for 1 hour. Meanwhile, 24 parts of methanol were added to 7.3 parts of 35% hydrochloric acid and stirred under ice cooling. The solution containing the azo dye was added dropwise to the mixture. After the dropwise addition was completed, the mixture was stirred at room temperature for another 1 hour to obtain an orange suspension. The orange solid obtained by filtration was dispersed and washed with water, filtered, and dried at 60°C under reduced pressure to obtain 9.8 parts of azo dye (5-2) consisting of a compound represented by formula (AI-19) (yield 98%). The X-ray diffraction parameters of the azo dye (5-2) are shown in Table 6.

[0343] <Synthesis Example 7> 3.0 parts of the azo dye (5-1) obtained in Synthesis Example 5, 12.7 parts of tetraethylammonium hydroxide (35% aqueous solution), and 51.0 parts of methanol were mixed and stirred at room temperature for 1 hour. Meanwhile, 7.2 parts of methanol were added to 3.4 parts of 35% hydrochloric acid and stirred under ice cooling. The solution containing the azo dye was added dropwise to the mixture. After the dropwise addition was completed, the mixture was stirred at room temperature for another 1 hour to obtain an orange suspension. The orange solid obtained by filtration was dispersed and washed with water, then filtered and dried at 60°C under reduced pressure to obtain 2.8 parts of azo dye (5-3) consisting of a compound represented by formula (AI-19) (yield 94%). The X-ray diffraction parameters of the azo dye (5-3) are shown in Table 6.

[0344] <Synthesis Example 8> 2.0 parts of the azo dye (5-1) obtained in Synthesis Example 5, 4.7 parts of tetramethylammonium hydroxide (25% aqueous solution), and 14 parts of acetonitrile were mixed and stirred at room temperature for 1 hour. Meanwhile, 4.8 parts of water were added to 1.5 parts of 35% hydrochloric acid and stirred under ice cooling. The solution containing the azo dye was added dropwise to the mixture. After the dropwise addition was completed, the mixture was stirred at room temperature for another 1 hour to obtain an orange suspension. The orange solid obtained by filtration was dispersed and washed with water, then filtered and dried at 60°C under reduced pressure to obtain 1.9 parts of azo dye (5-4) consisting of a compound represented by formula (AI-19) (yield 96%). The X-ray diffraction parameters of the azo dye (5-4) are shown in Table 6.

[0345] <Synthesis Example 9> 1 part of the azo dye (5-1) obtained in Synthesis Example 5 and 40 parts of 90% sulfuric acid were mixed and stirred at 23° C. for 1 hour. 45 parts of acetonitrile were added thereto and stirred at the same temperature for 1 hour to obtain a suspension. The solid obtained by filtration was dispersed and washed with water, then filtered and dried at 60° C. under reduced pressure to obtain 0.9 parts of the azo dye (5-5) consisting of the compound represented by formula (AI-19) (yield 90%). The X-ray diffraction parameters of the azo dye (5-5) are shown in Table 6.

[0346] <Synthesis Example 10> 1.3 parts of the azo dye (5-1) obtained in Synthesis Example 5 and 19.6 parts of trifluoroacetic acid were mixed, heated to 40° C., and stirred for 1 hour. 5.2 parts of methanol were added thereto and stirred for 0.5 hours, then cooled to room temperature, 15.6 parts of methanol were added and stirred to obtain an orange suspension. The orange solid obtained by filtration was dispersed and washed with water, filtered, and dried at 60° C. under reduced pressure to obtain 1.2 parts of azo dye (5-6) consisting of a compound represented by formula (AI-19) (yield 92%). The X-ray diffraction parameters of the azo dye (5-6) are shown in Table 6.

[0347] <Example 5> 0.5 parts of the azo dye (5-2) obtained in Synthesis Example 6, 3.0 parts of N-methylpyrrolidone, and 10.5 parts of xylene were mixed, and the mixture in a slurry state was stirred for 3 hours at an internal temperature of 125° C. After cooling to room temperature, the mixture obtained was filtered, and the resulting residue was dried under reduced pressure at 60° C. to obtain 0.45 parts of the azo dye (5a) consisting of a compound represented by formula (AI-19) (yield 90%). The X-ray diffraction spectrum of the azo dye (5a) is shown in FIG. 9, and the X-ray diffraction parameters are given in Table 6.

[0348] <Example 6> 0.5 parts of the azo dye (5-2) obtained in Synthesis Example 6, 0.5 parts of N-methylpyrrolidone, 5.0 parts of xylene, and 0.5 parts of ethanolamine were mixed, and the mixture in a slurry state was stirred at an internal temperature of 125° C. for 3 hours. After cooling to room temperature, 1 part of methanol was added dropwise and stirred for 1 hour. The resulting mixture was filtered, and the resulting residue was dried under reduced pressure at 60° C. to obtain 0.4 parts of the azo dye (5b) consisting of a compound represented by formula (AI-19) (yield 88%). The X-ray diffraction spectrum of the azo dye (5b) is shown in FIG. 10, and the X-ray diffraction parameters are given in Table 6.

[0349] <Example 7> 1.4 parts of the azo dye (5-1) obtained in Synthesis Example 5 and 84 parts of N-methylpyrrolidone were mixed, and the mixture in a slurry state was stirred at an internal temperature of 125° C. for 3 hours. After cooling to an internal temperature of 60° C., 6 parts of acetonitrile were added dropwise, and after further cooling to room temperature, 30 parts of acetonitrile were added dropwise and stirred for 1 hour. The resulting mixture was filtered, and the resulting residue was dried under reduced pressure at 60° C. to obtain 1.2 parts of azo dye (5c) consisting of a compound represented by formula (AI-19) (yield 86%). The X-ray diffraction spectrum of the azo dye (5c) is shown in FIG. 11, and the X-ray diffraction parameters are given in Table 6.

[0350] <Example 8> 25 parts of the azo dye (5-1) obtained in Synthesis Example 5 and 375 parts of xylene were mixed, and the mixture in a slurry state was stirred for 3 hours at an internal temperature of 125° C. After cooling to room temperature, the resulting mixture was filtered, and the resulting residue was dried under reduced pressure at 60° C. to obtain 22 parts of an azo dye (5d) composed of a compound represented by formula (AI-19) (yield 90%). The X-ray diffraction spectrum of the azo dye (5d) is shown in FIG. 12, and the X-ray diffraction parameters are given in Table 6.

[0351] <Example 9> 1 part of the azo dye (5-1) obtained in Synthesis Example 5 and 100 parts of toluene were mixed, and the mixture in a slurry state was stirred for 3 hours at an internal temperature of 100° C. After cooling to room temperature, the resulting mixture was filtered, and the resulting residue was dried under reduced pressure at 60° C. to obtain 0.9 parts of the azo dye (5e) composed of a compound represented by formula (AI-19) (yield 90%). The X-ray diffraction spectrum of the azo dye (5e) is shown in FIG. 13, and the X-ray diffraction parameters are given in Table 6.

[0352] <Example 10> 1.0 part of the azo dye (5-2) obtained in Synthesis Example 6, 1.7 parts of N-methylpyrrolidone, 10.0 parts of xylene, and 0.3 parts of ethanolamine were mixed, and the mixture in a slurry state was stirred at an internal temperature of 125° C. for 3 hours. After cooling to room temperature, 2 parts of methanol were added dropwise and stirred for 1 hour. The resulting mixture was filtered, and the resulting residue was dried under reduced pressure at 60° C. to obtain 0.78 parts of the azo dye (5f) consisting of a compound represented by formula (AI-19) (yield 78%). The X-ray diffraction spectrum of the azo dye (5f) is shown in FIG. 14, and the X-ray diffraction parameters are given in Table 6.

[0353] <Example 11> 1.0 part of the azo dye (5-2) obtained in Synthesis Example 6, 3.4 parts of N-methylpyrrolidone, 10.0 parts of xylene, and 0.6 parts of ethanolamine were mixed, and the mixture in a slurry state was stirred at an internal temperature of 125°C for 3 hours. After cooling to room temperature, 2 parts of methanol were added dropwise and stirred for 1 hour. The resulting mixture was filtered, and the resulting residue was dried under reduced pressure at 60°C to obtain 0.76 parts of an azo dye (5g) consisting of a compound represented by formula (AI-19) (yield 76%). The X-ray diffraction spectrum of the azo dye (5g) is shown in FIG. 15, and the X-ray diffraction parameters are given in Table 6.

[0354] <Example 12> 0.5 parts of the azo dye (5-2) obtained in Synthesis Example 6, 1.0 parts of cyclohexanone, 5.0 parts of xylene, and 1.0 parts of ethanolamine were mixed, and the mixture in a slurry state was stirred for 3 hours at an internal temperature of 125° C. After cooling to room temperature, the mixture obtained was filtered, and the residue obtained was dried under reduced pressure at 60° C. to obtain 0.44 parts of the azo dye (5h) consisting of a compound represented by formula (AI-19) (yield 88%). The X-ray diffraction spectrum of the azo dye (5h) is shown in FIG. 16, and the X-ray diffraction parameters are given in Table 6.

[0355] <Example 13> 1.0 part of the azo dye (5-3) obtained in Synthesis Example 7, 6.0 parts of N-methylpyrrolidone, and 21.0 parts of xylene were mixed, and the mixture in a slurry state was stirred for 3 hours at an internal temperature of 125° C. After cooling to room temperature, the mixture obtained was filtered, and the resulting residue was dried under reduced pressure at 60° C. to obtain 0.8 parts of the azo dye (5i) consisting of a compound represented by formula (AI-19) (yield 80%). The X-ray diffraction spectrum of the azo dye (5i) is shown in FIG. 17, and the X-ray diffraction parameters are given in Table 6.

[0356] <Example 14> 1.5 parts of the azo dye (5-4) obtained in Synthesis Example 8, 1.5 parts of N-methylpyrrolidone, 15.0 parts of xylene, and 1.5 parts of ethanolamine were mixed, and the mixture in a slurry state was stirred at an internal temperature of 125° C. for 3 hours. After cooling to room temperature, 3 parts of methanol were added dropwise and stirred for 1 hour. The resulting mixture was filtered, and the resulting residue was dried under reduced pressure at 60° C. to obtain 1.3 parts of the azo dye (5j) consisting of a compound represented by formula (AI-19) (yield 87%). The X-ray diffraction spectrum of the azo dye (5j) is shown in FIG. 18, and the X-ray diffraction parameters are given in Table 6.

[0357] <Example 15> 1.0 part of the azo dye (5-5) obtained in Synthesis Example 9 and 60 parts of N-methylpyrrolidone were mixed, and the mixture in a slurry state was stirred at an internal temperature of 125°C for 3 hours. After cooling to 60°C, 5.0 parts of acetonitrile were added dropwise and stirred for 1 hour. After cooling to room temperature, 25.0 parts of acetonitrile were added dropwise and stirred for 1 hour. The resulting mixture was filtered, and the resulting residue was dried under reduced pressure at 60°C to obtain 0.75 parts of azo dye (5k) consisting of a compound represented by formula (AI-19) (yield 75%). The X-ray diffraction spectrum of the azo dye (5k) is shown in FIG. 19, and the X-ray diffraction parameters are given in Table 6.

[0358] <Example 16> 0.5 parts of the azo dye (5-6) obtained in Synthesis Example 10 and 15.0 parts of N-methylpyrrolidone were mixed, and the mixture in a slurry state was stirred at an internal temperature of 125°C for 3 hours. After cooling to 60°C, 2.4 parts of acetonitrile were added dropwise and stirred for 1 hour. After cooling to room temperature, 19.9 parts of acetonitrile were added dropwise and stirred for 1 hour. The resulting mixture was filtered, and the resulting residue was dried under reduced pressure at 60°C to obtain 0.38 parts of azo dye (51) consisting of a compound represented by formula (AI-19) (yield 75%). The X-ray diffraction spectrum of the azo dye (5l) is shown in FIG. 20 and the X-ray diffraction parameters are given in Table 6.

[0359] [Table 6]

[0360] In Table 6, 2θmax is the diffraction angle at which the maximum peak is detected in the diffraction angle range (2θ±0.2°)=5° to 25°.

[0361] <Synthesis Example 11> <Synthesis of colorant (a)> A compound represented by formula (a) was synthesized according to the method described in JP-A-2002-179979.

[0362] [ka]

[0363] <Synthesis Example 12> A suitable amount of nitrogen was flowed into a flask equipped with a reflux condenser, a dropping funnel, and a stirrer to create a nitrogen atmosphere, 280 parts of propylene glycol monomethyl ether acetate was added, and the mixture was heated to 80°C with stirring. Next, 38 parts of acrylic acid, 3,4-epoxytricyclo[5.2.1.0 2,6 ]decan-8-yl acrylate and 3,4-epoxytricyclo[5.2.1.0 2,6 ] A mixture of 289 parts of a mixture of decan-9-yl acrylate (content ratio 1:1 by molar ratio) and 125 parts of propylene glycol monomethyl ether acetate was added dropwise over 5 hours. Meanwhile, a solution of 33 parts of 2,2'-azobis(2,4-dimethylvaleronitrile) dissolved in 235 parts of propylene glycol monomethyl ether acetate was added dropwise over 6 hours. After the completion of the dropwise addition, the mixture was kept at 80°C for 4 hours and then cooled to room temperature to obtain a copolymer (resin B-1) solution with a solid content of 35.1% and a viscosity of 125 mPas measured with a B-type viscometer (23°C). The weight average molecular weight Mw of the resulting copolymer was 9200, the degree of dispersion was 2.08, and the acid value converted to solid content was 77 mg-KOH / g. Resin B-1 has the following structural units.

[0364] [ka]

[0365] <Examples 17 to 21 and Comparative Examples 1 to 5> (1) Preparation of dispersion (Dispersion Liquid Preparation Example 1) 4.5 parts of the azo dye (1) obtained in Example 1, 0.5 parts of the compound represented by formula (a), 3.5 parts of a dispersant (BYKLPN-6919 manufactured by BYK) (solid content equivalent), 3.5 parts of resin B-1 (solid content equivalent), 83 parts of propylene glycol monomethyl ether acetate, and 5.0 parts of diacetone alcohol were mixed, and 300 parts of 0.2 mm zirconia beads were added and shaken, and the zirconia beads were removed by filtration to obtain a dispersion (P-1).

[0366] (Dispersion Liquid Preparation Examples 2 to 10) Dispersions (P-2) to (P-10) were obtained in the same manner as in Dispersion Preparation Example 1, except that the azo dye (1) in Dispersion Preparation Example 1 was changed to the following azo dyes. Dispersion (P-2): Azo dye (1-1) obtained in Synthesis Example 1 Dispersion (P-3): Azo dye (2) obtained in Example 2 Dispersion (P-4): Azo dye (2-1) obtained in Synthesis Example 2 Dispersion (P-5): Azo dye (3) obtained in Example 3 Dispersion (P-6): Azo dye (3-1) obtained in Synthesis Example 3 Dispersion (P-7): Azo dye (4) obtained in Example 4 Dispersion (P-8): Azo dye (4-1) obtained in Synthesis Example 4 Dispersion (P-9): Azo dye (5a) obtained in Example 5 Dispersion (P-10): Azo dye (5-1) obtained in Synthesis Example 5

[0367] (2) Preparation of Colored Curable Resin Composition The components of the dispersion liquid (P), resin (B), polymerizable compound (C), polymerization initiator (D), solvent (E), and leveling agent (F) were mixed so as to obtain the composition shown in Table 7, thereby obtaining a colored curable resin composition.

[0368] [Table 7]

[0369] In Table 7, each component represents the following compound. Resin (B-1): Resin B-1 (solid content equivalent) Polymerizable compound (C-1): dipentaerythritol polyacrylate (product name "A-9570", manufactured by Shin-Nakamura Chemical Co., Ltd.) Polymerization initiator (D-1): N-acetyloxy-1-(4-phenylsulfanylphenyl)-3-cyclohexylpropan-1-one-2-imine (trade name "PBG-327"; O-acyloxime compound, manufactured by Changzhou Strong Electronic New Materials Co., Ltd.) Solvent (E-1): Propylene glycol monomethyl ether acetate Leveling agent (F-1): Polyether modified silicone oil (product name "TORAY SILICONE SH8400", manufactured by Toray Dow Corning Co., Ltd.)

[0370] (3) Preparation of colored coating film A colored curable resin composition was applied by spin coating onto a 5 cm square glass substrate (Eagle XG; Corning) so that the film thickness after post-baking was 2 μm, and then pre-baked at 100° C. for 3 minutes to form a colored composition layer. After cooling, the colored composition layer formed on the substrate was exposed to 80 mJ / cm 2 under air atmosphere using an exposure machine (TME-150RSK; Topcon). 2 After the light irradiation, the coating was post-baked in an oven at 230° C. for 30 minutes to obtain a colored coating film. The thickness of the obtained colored coating film was measured using DEKTAK3 (manufactured by ULVAC, Inc.).

[0371] (4) Heat resistance evaluation The obtained colored coating film was heated in an oven at 230° C. for 120 minutes. For the colored coating film before and after heating, the xy chromaticity coordinates (x, y) and the stimulus value Y were measured from the spectral data measured with a colorimeter (OSP-SP-200; manufactured by Olympus Corporation), and the color difference ΔE was calculated from the measured values ​​according to the method described in JIS Z 8730:2009 (7. Calculation method of color difference). * ab was calculated. △E * The smaller the ab, the smaller the color change. The results are shown in Table 8.

[0372] (5) Light resistance evaluation An ultraviolet ray cut filter (COLORED OPTICAL GLASS L38: manufactured by Hoya Co., Ltd.; cuts light of 380 nm or less) was placed on the obtained colored coating film, and the upper surface of the filter was irradiated with xenon lamp light for 48 hours using a light resistance tester (SUNTEST CPS+: manufactured by Toyo Seiki Co., Ltd.). For the colored coating film before and after the light irradiation, the xy chromaticity coordinates (x, y) and the stimulus value Y were measured from the spectral data measured with a colorimeter (OSP-SP-200; manufactured by Olympus Co., Ltd.), and the color difference ΔE was calculated from the measured values ​​according to the method described in JIS Z 8730:2009 (7. Calculation method of color difference). * ab was calculated. △E * The smaller the ab, the smaller the color change. The results are shown in Table 8.

[0373] [Table 8]

[0374] From the results of Examples 17 to 21 and Comparative Examples 1 to 5, it was possible to form a color filter having improved heat resistance and light resistance by using an azo dye having the same chemical structure as that of the present invention, since the dye has the specified crystal structure of the present invention.

Claims

1. An azo dye represented by the following formula (I): The azo dye has a powder X-ray diffraction pattern obtained by using CuKα radiation for a mixture of 50 parts of the azo dye and 50 parts of aluminum oxide. A peak exists in the range of diffraction angle (2θ±0.2°)=5° to 25°, At 9.8° to 16.0°, there is a maximum peak at 5° to 25°, At least one peak is present between 11.0° and 11.8°, Maximum peak intensity at 9.8° to 16.0° (I 1 ) and the maximum peak intensity at 11.0° to 11.8° (I 2 ) between I 2 / I 1 ≧0.05 and The peak intensity (I) at the diffraction angle (2θ±0.2°)=35.1° due to aluminum oxide 3 ) and said I 1 Between I 1 / I 3 ≧0.35 Azo dyes. 【Chemistry 1】 [In formula (I), L 1 represents a group represented by formula (ph1-1), formula (ph1-2), formula (ph11-1), or formula (ph11-2), A represents a group represented by formula (ia). 【Chemistry 2】 [In formula (ph1-1), formula (ph1-2), formula (ph11-1), and formula (ph11-2), X 1a , X 1b , X 10 , X 11a , X 11b each independently represents a substituent or a hydrocarbon group which may have a substituent. n1 represents an integer of 0 to 5, and n2 represents an integer of 0 to 4. When n1 represents an integer of 2 or more, a plurality of X 1a may be the same or different, and when n2 represents an integer of 2 or more, a plurality of X 1b may be the same or different. n1 represents an integer of 2 or more, and X 1a is bonded to an adjacent carbon atom, X bonded to the adjacent carbon atom 1a may be bonded to each other to form a ring, n2 represents an integer of 2 or more, and X 1b is bonded to an adjacent carbon atom, X bonded to the adjacent carbon atom 1b may be bonded to each other to form a ring. p represents an integer of 0 to 4. When p represents an integer of 2 or more, a plurality of X 10 may be the same or different. p represents an integer of 2 or more, and X 10 is bonded to an adjacent carbon atom, X bonded to the adjacent carbon atom 10 may be bonded to each other to form a ring. q1 represents an integer of 0 to 5, and q2 represents an integer of 0 to 4. When q1 represents an integer of 2 or more, a plurality of X 11a may be the same or different, and when q2 represents an integer of 2 or more, 11b may be the same or different. q1 represents an integer of 2 or more, and X 11a is bonded to an adjacent carbon atom, X bonded to the adjacent carbon atom 11a may be bonded to each other to form a ring, q2 represents an integer of 2 or more, and X 11b is bonded to an adjacent carbon atom, X bonded to the adjacent carbon atom 11b may be bonded to each other to form a ring. Y is -O-, -CO-, -SO 2 -, or -C(CF 3 ) 2 Represents -. * represents a bond to A. ** represents a bond to the group represented by formula (ib). 【Chemistry 3】 [In formula (ia) and formula (ib), X 6 ~X 9 each independently represents a hydrocarbon group which may have a substituent, and —CH 2 - may be replaced by -O-, -CO-, or -NH-, -CH= contained in the hydrocarbon group may be replaced by -N=, and -C< contained in the hydrocarbon group may be replaced by -N<. X 6 and X 7 may be bonded to each other to form a ring, X 8 and X 9 may be bonded to each other to form a ring. * is L 1 It represents a bond with .

2. The group represented by formula (ph1-2) is a group represented by formula (ph2-2), The group represented by formula (ph11-1) is a group represented by formula (ph12-1), The azo dye according to claim 1, wherein the group represented by formula (ph11-2) is a group represented by formula (ph12-2): 【Chemistry 4】 [In formula (ph2-2), formula (ph12-1), and formula (ph12-2), X 2b ~X 5b , X 12a ~X 15a , X 21a ~X 25a , X 12b ~X 15b , X 22b ~X 25b each independently represents a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, an amino group, an amide group, a carboxylic acid amide group, a carboxyl group, an alkoxy group having 1 to 4 carbon atoms, an alkylthio group having 1 to 4 carbon atoms, a cyano group, or a halogen atom. X 2b and X 3b , X 4b and X 5b , X 12a and X 13a , X 14a and X 15a , X 22a and X 23a , X 21a and X 23a , X 21a and X 25a , X 24a and X 25a , X 12b and X 13b , X 14b and X 15b , X 22b and X 23b , X 24b and X 25b may be bonded to each other to form a ring. Y has the same meaning as above. * represents a bond to A. ** represents a bond to the group represented by formula (ib).

3. The azo dye according to claim 1, wherein the groups represented by formula (ia) and formula (ib) are each independently any of the groups represented by formulas (t1) to (t5). 【Chemistry 5】 [In formulas (t1) to (t5), R 1 ~R 16 each independently represents a hydrogen atom, an optionally substituted hydrocarbon group, a heterocyclic group, a cyano group, or a halogen atom. * is L 1 represents a bond with . ]

4. A colored curable resin composition comprising the azo dye according to any one of claims 1 to 3, a resin, a polymerizable compound, a polymerization initiator, and a solvent.

5. A color filter formed from the colored curable resin composition according to claim 4.

6. A display device comprising the color filter according to claim 5 .

7. A solid-state imaging device comprising the color filter according to claim 5 .

8. A method for producing an azo dye, comprising: a contacting step of contacting an azo dye (A) in a slurry state with a solvent (Z) at a temperature of 80 to 200°C; and a separation step of extracting the azo dye (A) contacted with the solvent (Z) by solid-liquid separation, wherein the solvent (Z) comprises at least one solvent selected from the group consisting of ester solvents, ether solvents, ether ester solvents, ketone solvents, nitrile solvents, alcohol solvents, amide solvents, aromatic hydrocarbon solvents, sulfoxide solvents, sulfone solvents, halogenated solvents, and amine solvents, and the amount of the solvent (Z) in the contacting step is 0.1 to 120.0 times by mass relative to the azo dye (A).

Images