Colored photosensitive resin composition and its uses

Abstract

An object of the present invention is to provide a colored photosensitive resin composition that has high brightness, good color properties, and excellent solvent resistance, and to provide a high-brightness color filter that has excellent color tones, particularly a color filter that can be used in a liquid crystal display. [Solution] A colored photosensitive resin composition includes a colorant containing a phthalocyanine dye of a specific structure, an alkali-soluble resin, and a photopolymerization initiator. The phthalocyanine dye preferably has a light transmittance of 85% or more at a wavelength of 480 nm when the absorbance at the maximum absorption wavelength is taken as 1. Furthermore, the colorant preferably contains an azo yellow dye or an azo yellow pigment. Furthermore, the above-mentioned problems can be solved by a cured film obtained by curing the colored photosensitive resin composition.

Description

[Technical Field]

[0001] The present invention relates to a colored photosensitive resin composition and a cured film formed therefrom, as well as to a member for a display device and a display device having the cured film. [Background technology]

[0002] Photosensitive resin compositions are compositions whose physical properties change when a coating film is irradiated with light or an electron beam, i.e., compositions that have the property that, for example, the exposed portion hardens and the remaining portion remains soluble. Taking advantage of these properties, they are used in various fields, such as electronic information materials and optical materials, and one of their main applications is color filters. Color filters are a key component of liquid crystal display devices and image pickup tube elements.

[0003] Color filters used in liquid crystal displays (LCDs) and the like are generally manufactured by forming, on a substrate such as glass, plastic, an image sensor, or a thin-film transistor, three primary color pixels of red (R), green (G), and blue (B) arranged in a pattern of fine colored pixels on the substrate, and a black matrix, which is a light-shielding layer, provided between these pixels. These pixels and black matrix are formed by applying a colored photosensitive resin composition containing an alkali-soluble resin and a colorant onto the substrate, heating and drying (pre-baking) to form a coating film, exposing this coating film to ultraviolet light, developing it, removing the unexposed parts by alkaline washing, and then post-curing (post-baking). Competition in the color filter LCD market is intensifying, and there is a strong demand for improved quality in color filters, such as better color tone, higher brightness, and color reproducibility. For example, a pigment dispersion composition for color filters has been proposed that uses a finely divided pigment and a specific alkali-soluble resin as a colorant to improve brightness, thereby achieving excellent dispersion stability of the colorant (Patent Document 1). Also, a coloring composition for color filters has been proposed that uses CI Pigment Green 58 and a specific yellow dye, thereby achieving high brightness and high color purity of green pixels (Patent Document 2). Although various compositions have been proposed so far, there is still room for further improvement in order to improve brightness. [Prior art documents] [Patent documents]

[0004] [Patent Document 1] Japanese Patent Application Publication No. 2017-138503 [Patent Document 2] Japanese Patent Application Laid-Open No. 2012-194200 Summary of the Invention [Problem to be solved by the invention]

[0005] In recent years, with the demand for higher performance of image display devices, improvements in brightness and contrast have been required. Methods for forming a color filter with high brightness include finer pigments and more uniform dispersion. However, the present inventors have noticed that finer color materials have poor dispersion stability, which can cause problems such as deterioration in color reproducibility and brightness over time. They have found that a colored photosensitive resin composition containing a specific color material is important. Therefore, the present invention has been made in view of the above circumstances, and an object of the present invention is to provide a colored photosensitive resin composition that has high brightness, good color characteristics, and excellent solvent resistance. Another object of the present invention is to provide a color filter having excellent color tone and high brightness, particularly a color filter for use in a liquid crystal display. [Means for solving the problem]

[0006] As a result of extensive investigations, the present inventors have found a colored photosensitive resin composition and a cured film suitable for color filters. That is, the objects of the present invention are achieved by the following (1) to (11). (1) A colored photosensitive resin composition comprising a colorant, an alkali-soluble resin, and a photopolymerization initiator, wherein the colorant is a compound represented by the following general formula (I):

[0007] [ka]

[0008] (However, Z1~Z 16 is a hydrogen atom, SR 1 , OR 2 or a halogen atom, R 1 and R 2 each independently represent a phenyl group which may have a substituent, a naphthyl group which may have a substituent, an aralkyl group which may have a substituent, or an alkyl group having 1 to 20 carbon atoms which may have a substituent, and M represents a metal atom, a metal oxide, or a metal halide. (2) The phthalocyanine dye is represented by the following general formula (IV):

[0009] [ka]

[0010] (wherein M represents a metal atom, a metal oxide, or a metal halide; X 1 ~X 4 and Y 1 ~Y 4 are the same or different and represent a hydrogen atom (H), a fluorine atom (F), or an OR group which may have a substituent. 8 represents the group OR 8 The group represents an alkoxy group, a phenoxy group, or a naphthoxy group, provided that X 1 and Y 1 At least one of X 2 and Y 2 At least one of X3 and Y 3 At least one of, and X 4 and Y 4 At least one of the OR groups may have a substituent. 8 (1) The colored photosensitive resin composition according to (1), wherein the dye is a phthalocyanine dye represented by the formula (I) (3) The colored photosensitive resin composition according to claim 1 or 2, wherein M in the structural formula of the phthalocyanine dye is a metal atom selected from Co, Ni, Cu, and Zn. (4) The colored photosensitive resin composition according to any one of (1) to (3), wherein the phthalocyanine dye has a light transmittance of 85% or more at a wavelength of 480 nm when the absorbance at the absorption maximum wavelength is taken as 1. (5) The colored photosensitive resin composition according to any one of (1) to (4), wherein the coloring material further contains a yellow coloring material. (1) The colored photosensitive resin composition according to (5), wherein the yellow coloring material is an azo yellow dye or an azo yellow pigment. (7) The colored photosensitive resin composition according to any one of (1) to (6), further comprising a polymerizable monomer. (8) A cured film obtained by curing the colored photosensitive resin composition according to any one of (1) to (7) above. (9) A member for a display device having the cured film according to (8) above. (10) A color filter having the cured film according to (8) on a substrate. (11) A display device having the member for a display device according to (9) above or the color filter according to (10). [Effects of the Invention]

[0011]

[0023] By using the colored photosensitive resin composition of the present invention, it is possible to obtain a cured film having high luminance, which exhibits solvent resistance and is sufficiently inhibited from bleeding out of the coloring material, and by combining it with a yellow coloring material, the effect of improving luminance can be further enhanced. Color filters and display device members having such cured films are very useful as electronic information materials. [Brief explanation of the drawings]

[0012] [Figure 1] 1 is an example of an absorption spectrum of a coating film containing the phthalocyanine dye of the present invention. [Figure 2] 1 is a graph showing the relationship between the chromaticity coordinate values ​​(x, y) when the film thickness of the coating film obtained from the colored photosensitive resin compositions of Example 1 and Comparative Example 1 is changed. [Figure 3] 10 is a graph showing the relationship between the luminance difference ΔY in the colored photosensitive resin compositions of Table 8, ΔY in a composition containing only a yellow coloring material, and ΔY in a composition containing both a green coloring material and a yellow coloring material. DETAILED DESCRIPTION OF THE INVENTION

[0013] The present invention will be described in detail below. In addition, a combination of two or more of the individual preferred embodiments of the present invention described below is also a preferred embodiment of the present invention. In addition, in this specification, "(meth)acrylic acid" means "acrylic acid and / or methacrylic acid", and "(meth)acrylate" means "acrylate and / or methacrylate". In this specification, the numerical range "Min to Max" means a range equal to or greater than the minimum value Min and equal to or less than the maximum value Max. Furthermore, when preferred numerical values ​​are given in stages for the upper and lower limit values, a numerical range obtained by appropriately combining the separately given upper and lower limit values ​​is also a preferred numerical range. As described above, the colored photosensitive resin composition of the present invention contains a colorant with a specific structure, an alkali-soluble resin, and a photopolymerization initiator. The inclusion of these components makes the colored photosensitive resin composition suitable for use in optical materials, and it can provide, for example, a cured film with high brightness as a colored photosensitive resin composition for color filters. One or more of these components may be used. If necessary, the composition may further contain one or more other components. In the present invention, the term "optical material" refers to a material used in photolithography, such as a component of a device in the optical or electrical / electronic fields. For example, the term refers to a component of a color filter, black matrix, black column spacer, optical lens, ink, printing plate, printed wiring board, semiconductor element, photoresist, insulating film, etc., used in liquid crystal, organic electroluminescence (EL), quantum dot, or micro LED display devices, solid-state imaging devices, touch panel display devices, etc. In particular, a colored photosensitive resin composition for color filters is preferred because it has good solvent resistance and can produce a cured film with high brightness. Examples of the color filter include various color filters such as color filters for color liquid crystal display elements, color filters for color separation in solid-state imaging elements, and color filters for organic EL display elements.

[0014] Each component contained in the colored photosensitive resin composition of the present invention will be described below. In this specification, the term "total solid content" refers to the total amount of components that form a cured film, excluding the solvent and other volatile components. Furthermore, the term "solid content ratio" refers to the weight ratio of each solid content of the colorant, alkali-soluble resin, polymerizable monomer, and photopolymerization initiator. [Colorant] The colored photosensitive resin composition of the present invention is characterized by containing a specific phthalocyanine dye, that is, a compound represented by the following formula (I), as a coloring material.

[0015] [ka]

[0016] (However, Z1~Z16 is a hydrogen atom, SR 1 , OR 2 or a halogen atom, R 1 and R 2 each independently represents an optionally substituted phenyl group, an optionally substituted naphthyl group, an optionally substituted aralkyl group, or an optionally substituted alkyl group having 1 to 20 carbon atoms, and M represents a metal atom, a metal oxide, or a metal halide. Above R 1 and R 2 each independently represents a phenyl group which may have a substituent, a naphthyl group which may have a substituent, an aralkyl group which may have a substituent, or an alkyl group having 1 to 20 carbon atoms which may have a substituent. In the present specification, examples of the substituent "optionally having a substituent" include, but are not limited to, a halogen atom, an acyl group, an alkyl group, a phenyl group, an alkoxyl group, a halogenated alkyl group, a halogenated alkoxyl group, a nitro group, an amino group, an alkylamino group, an alkylcarbonylamino group, an arylamino group, an arylcarbonylamino group, a carbonyl group, an alkoxycarbonyl group, an alkylaminocarbonyl group, an alkoxysulfonyl group, an alkylthio group, a carbamoyl group, an aryloxycarbonyl group, an oxyalkyl ether group, and a cyano group. When a plurality of these substituents are present, they may be the same or different.

[0017] The aralkyl group refers to a group in which a hydrogen atom of an alkyl group is substituted with an aryl group, and the aryl group is not particularly limited, and examples thereof include a phenyl group, a benzyl group, a phenethyl group, an o-, m-, or p-tolyl group, a 2,3- or 2,4-xylyl group, a mesityl group, a naphthyl group, an anthryl group, a phenanthryl group, a biphenylyl group, a benzhydryl group, a trityl group, and a pyrenyl group.

[0018] Furthermore, the alkyl group having 1 to 20 carbon atoms is not particularly limited and may be a straight-chain, branched-chain, or cyclic alkyl group having 1 to 20 carbon atoms, and specific examples thereof include a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group, a sec-butyl group, a tert-butyl group, an n-pentyl group, an isopentyl group, a neopentyl group, a 1,2-dimethylpropyl group, an n-hexyl group, a cyclohexyl group, a 1,3-dimethylbutyl group, a 1-isopropylpropyl group, a 1,2-dimethylbutyl group, an n-heptyl group, a 1,4-dimethylpentyl group, a 2-methyl-1-isopropylpropyl group, a 1-ethyl-3-methylbutyl group, an n-octyl group, and a 2-ethylhexyl group. M represents a metal atom, metal oxide, or metal halide. Examples of metal atoms include iron, magnesium, nickel, cobalt, copper, palladium, zinc, vanadium, titanium, indium, and tin. Examples of metal oxides include titanyl and vanadyl. Examples of metal halides include aluminum chloride, indium chloride, germanium chloride, tin(II) chloride, tin(IV) chloride, and silicon chloride. Preferred are copper, zinc, cobalt, nickel, iron, vanadyl, titanyl, and tin(II) chloride, more preferably copper, zinc, cobalt, and nickel, and particularly preferably zinc and copper. Zinc and copper offer excellent heat resistance and light resistance. When the colored photosensitive resin composition of the present invention is used in LCD filters, high optical properties (transparency) are particularly required. Therefore, for the above applications, phthalocyanine compounds with zinc as the central metal, which have excellent optical properties (transparency), are particularly preferred. From the viewpoint of improving solubility, the above M is preferably a metal atom (preferably Co, Ni, Cu or Zn), a metal oxide or a metal halide. 1 , Z 4 , Z 5 , Z 8 , Z 9 , Z 12 , Z 13 , Z 16 ), and the β-position atom (Z 2 , Z 3 , Z 6, Z 7 , Z 10 , Z 11 , Z 14 , Z 15 ) may be substituted with a substituent represented by the following formula (II-a), (II-b) or (II-c), a halogen atom, or may be a hydrogen atom.

[0019] [ka]

[0020] In formula (II-a), Q 1 represents an oxygen atom or a sulfur atom. 3 are the same or different and each represents a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, a nitro group, a cyano group, an aryl group having 6 to 20 carbon atoms which may have a substituent, an alkyl group having 1 to 20 carbon atoms which may have a substituent, an alkoxy group having 1 to 20 carbon atoms which may have a substituent, or -COOR 4 Represents R 4 represents an alkyl group having 1 to 20 carbon atoms which may have a substituent. 1 is an integer between 0 and 5. In formula (II-b), Q 2 represents an oxygen atom or a sulfur atom. 5 are the same or different and each represent a fluorine atom, a chlorine atom, a bromine atom, a nitro group, a cyano group, an aryl group having 6 to 20 carbon atoms which may have a substituent, an alkyl group having 1 to 20 carbon atoms which may have a substituent, an alkoxy group having 1 to 20 carbon atoms which may have a substituent, or -COOR 6 Represents R 6 represents an alkyl group having 1 to 20 carbon atoms which may have a substituent. 2 is an integer between 0 and 7. In formula (II-c), Q 3 represents an oxygen atom or a sulfur atom. 7 represents an alkoxy group having 1 to 20 carbon atoms which may have a substituent. The substituent at the β-position is effective in improving heat resistance, and the substituent at the α-position is effective in improving solvent solubility, so it is preferable to combine both in a balanced manner. In addition, in the above formula (I), Z1 to Z 16 are each independently a halogen atom or the following formula (II-d):

[0021] [ka] In the above formula (II-d), R8 represents a halogen atom, an alkyl group having 1 to 20 carbon atoms, an alkoxy group having 1 to 20 carbon atoms, a cyano group, a nitro group, or an ester group (-COOR9: R9 is an alkyl group having 1 to 20 carbon atoms), and n is an integer of 0 to 5; 16 It is more preferable that 3 to 16 of these groups are substituted phenoxy groups (II-d) and the remainder are halogen atoms. When M is copper or zinc, the greater the number of substituted phenoxy groups (II-d), the greater the conjugation, and the greater the shift of the maximum absorption wavelength of the phthalocyanine dye to the longer wavelength side, thereby making it possible to obtain a colored photosensitive resin composition suitable for use in green color filters. 16 Among these, it is particularly preferable that the number of the substituted phenoxy groups (II-d) is 6 to 16. In terms of improving color properties, the phthalocyanine dye is preferably a phthalocyanine dye (also referred to as dye α) that exhibits an absorption maximum in the wavelength range of 640 to 750 nm when the absorption spectrum of a solution of the phthalocyanine dye dissolved in a solvent is measured. Here, in order to exhibit an absorption maximum in the wavelength region of 700 to 750 nm, it is preferable that the atom at the α-position is substituted. When the substituent is (II-a), R 3 , R 5 At least one of them is preferably bonded to the ortho or meta position, more preferably to the ortho position. When the substituent is (II-c), Z 1 ~Z 16Of the 16 atoms, the number of atoms substituted with (II-c) is preferably 4 to 16, more preferably 8 to 16, and even more preferably 12 to 16. The atom at the β-position may be substituted or unsubstituted (remaining as a hydrogen atom), but from the viewpoint of solubility, it is preferably substituted with a substituent represented by (II-a), (II-b), or (II-c), or a halogen atom, and from the viewpoint of disrupting the planarity of the molecule and suppressing the degree of association, a substituent represented by (II-c) or a halogen atom is more preferred. As a result, the specific phthalocyanine dye (also referred to as dye α) is less likely to form aggregates, and therefore, when the absorption spectrum of a solution containing dye α is measured, it is more likely to show an absorption maximum in the wavelength range of 700 to 750 nm. Next, in order to exhibit an absorption maximum in the wavelength region of 640 to 700 nm, it is preferable that the atom at the β-position is substituted. When the substituent is (II-a), R 3 , R 5 At least one of the substituents is preferably bonded to the para position. 1 ~Z 16 Of the 16 atoms, the number of atoms substituted with (II-b) is preferably 4 to 10, more preferably 4 to 9, and even more preferably 4 to 8. The atom at the α-position may be substituted or unsubstituted (remaining as a hydrogen atom), but in order to have a steep absorption peak with a reduced shoulder peak when added to a resin or the like, it is preferable that the atom at the α-position be a hydrogen atom or be substituted with a halogen atom. As a result, the dye α is more likely to form aggregates, and when a solution or resin composition containing the dye α is produced, it is more likely to exhibit an absorption maximum in the wavelength range of 640 to 700 nm. In terms of improving brightness, when the absorbance at the maximum absorption wavelength is taken as 1, the light transmittance at a wavelength of 480 nm is preferably 85% or more, more preferably 90% or more, and most preferably 95% or more. In order to increase the light transmittance at a wavelength of 480 nm, it is necessary to increase the aggregation of the dye to have a steep (sharp) absorption peak. For this purpose, in the phthalocyanine dye represented by the above formula (I), 10 ,Z 11 ,Z 14 ,Z 15 ) is an OR group which may have a substituent. 10 As the substituent, an electron-withdrawing group is particularly preferred.

[0022] Here, a phthalocyanine dye suitable for increasing the transmittance of light having a wavelength of 480 nm and a method for producing the same will be described below. The phthalocyanine dye is represented by the following general formula (IV):

[0023] [ka] (wherein M represents a metal atom, a metal oxide, or a metal halide; X 1 ~X 4 and Y 1 ~Y 4 are the same or different and represent a hydrogen atom (H), a fluorine atom (F), or an OR group which may have a substituent. 10 represents the group OR 10 The group represents an alkoxy group, a phenoxy group, or a naphthoxy group, provided that X 1 and Y 1 At least one of X 2 and Y 2 At least one of X 3 and Y 3 At least one of, and X 4 and Y 4 At least one of the OR groups may have a substituent. 10 represents a group. In the above general formula (IV), OR 10 R that constitutes the group 10is an alkyl group, a phenyl group, or a naphthyl group, and may have a substituent. The alkyl group is, for example, preferably an alkyl group having 1 to 20 carbon atoms, more preferably an alkyl group having 1 to 8 carbon atoms, still more preferably an alkyl group having 1 to 6 carbon atoms, and particularly preferably an alkyl group having 1 to 4 carbon atoms. 10 Among these, a phenyl group or a phenyl group having a substituent is preferred. 1 ~X 4 and Y 1 ~Y 4 It is preferable that at least one of X in the general formula (IV) represents a phenoxy group which may have a substituent. This increases the aggregation property of the phthalocyanine dye, which allows the dye to sharply block the wavelength range it is desired to block, while exhibiting high transmittance in the wavelength range it is desired to transmit, thereby exhibiting light selective transmission properties (blocking and transmitting properties). In this way, the phthalocyanine dye can be formed by the X in the general formula (IV) above. 1 ~X 4 and Y 1 ~Y 4 In a particularly preferred embodiment, at least one of the groups represents a phenoxy group which may have a substituent.

[0024] Above OR 10 Examples of the substituent that the group may have include an alkoxycarbonyl group (-COOR 11 ), electron-withdrawing groups such as halogen groups (halogen atoms), cyano groups (-CN), and nitro groups (-NO2); alkyl groups (-R 12 ), alkoxy group (-OR 13 ) and other electron-donating groups; and the compound may contain one or more of these. Among these, electron-withdrawing groups are preferred from the viewpoint of improving the light selective transmission due to the fact that an associated molecular structure is easily formed. The electron-withdrawing group is preferably an alkoxycarbonyl group, a chlorine group (chlorine atom), or a cyano group, and more preferably a methoxycarbonyl group, a methoxyethoxycarbonyl group, a chlorine group, or a cyano group. In addition, the alkoxycarbonyl group (-COOR 11 ) that constitutes R 11is preferably an alkyl group or an alkoxy group having 1 to 8 carbon atoms, and the alkyl group (-R 12 ) that constitutes R 12 is preferably an alkyl group having a carbon number of 1 to 8. The alkoxycarbonyl group is preferably a methoxycarbonyl group or a methoxyethoxycarbonyl group, and the alkyl group is preferably a methyl group or a dimethyl group. Above OR 10 When the group has a substituent, the number of the substituents is not particularly limited, but is preferably, for example, 1 to 4. More preferably, it is 1 or 2. In addition, one OR 10 When a group has two or more substituents, the substituents may be the same or different. 10 The position of the substituent in the group is not particularly limited. Above X 1 and Y 1 At least one of X 2 and Y 2 At least one of X 3 and Y 3 At least one of, and X 4 and Y 4 At least one of the OR groups may have a substituent. 10 represents a group. Preferably, it is a phenoxy group which may have a substituent (i.e., a phenoxy group or a phenoxy group having a substituent). More preferably, X 1 ~X 4 and Y 1 ~Y 4 represents a phenoxy group which may have a substituent. Of these, a phenoxy group having a substituent is preferred, and the substituent is preferably an electron-withdrawing group as described above. In the general formula (IV), M represents a metal atom, a metal oxide, or a metal halide. The metal atom and the metal atoms constituting the metal oxide or metal halide are the same as those described above for M. Phthalocyanine compounds having copper, vanadium, or zinc as the central metal are preferred because they have superior solubility or dispersibility in solvents and resin components, visible light transmittance, and light resistance. Copper or zinc is more preferred. Phthalocyanine compounds having copper as the central metal are not subject to deterioration by light even when dispersed in any resin component (binder resin), and have extremely excellent light resistance. Phthalocyanine complexes (phthalocyanine compounds) having zinc as the central metal are preferred because they have excellent solubility in solvents and resin components, and can easily produce cured films and display device components with higher selective light transmittance. The halogen atoms constituting the metal halide are not particularly limited, and examples thereof include fluorine atoms, chlorine atoms, bromine atoms, and iodine atoms. The compound represented by the general formula (IV) can be synthesized by a conventional method described in, for example, Japanese Patent Publication No. 6-31239 etc. Specifically, the compound can be synthesized by reacting one selected from the group consisting of a metal, a metal oxide, a metal carbonyl, a metal halide and an organic acid metal (these are also collectively referred to as "metal compound") with a compound represented by the following general formula (III):

[0025] [ka] (In the formula, X a and Y a are the same or different and represent a hydrogen atom (H), a fluorine atom (F), or an OR group which may have a substituent. 10 represents the group OR 10 The group represents an alkoxy group, a phenoxy group, or a naphthoxy group. It is preferable to heat a phthalonitrile derivative represented by the formula (I) in the presence of an organic solvent to cause a cyclization reaction. The cyclization reaction of the phthalonitrile derivative is not particularly limited, and conventionally known methods described in JP-B-6-31239, Japanese Patent No. 3721298, Japanese Patent No. 3226504, Japanese Patent Laid-Open No. 2010-77408, etc., can be applied alone or with appropriate modifications. The substituents and OR 10The specific form of the group is as described above in relation to the general formula (IV). In the above general formula (III), X a and Y a Preferably, at least one of these is an OR which may have a substituent. 10 More preferably, X a and Y a and each of the OR groups may be the same or different and may have a substituent. 10 It is to represent a group. In the above reaction, the phthalonitrile derivative represented by the general formula (III) is X a and Y a and at least one of the OR groups may have a substituent. 10 It is preferable to use at least a compound in the form of a group. a and Y a any of which may have a substituent OR 10 Compounds in the form of groups (atoms) other than the X group a and Y a and at least one of the OR groups may have a substituent. 10 A compound in the form of a group may be used in combination. The metal compound is not particularly limited as long as it reacts with the phthalonitrile derivative to give the compound represented by general formula (IV). Examples include metals such as iron, copper, zinc, vanadium, titanium, indium, and tin; metal halide compounds of the metals such as chlorides, bromides, and iodides; metal oxides of the metals such as vanadium oxide, titanyl oxide, and copper oxide; organic acid metals such as acetates; complex compounds of the metals such as acetylacetonates, and metal carbonyls such as iron carbonyl; and the like. As described above, among the above metal compounds, metal halides are more preferred, vanadium iodide, copper iodide, and zinc iodide are even more preferred, and zinc iodide is particularly preferred. When zinc iodide is used, the central metal in the above general formula (IV) is zinc. When the reaction between the metal compound and the phthalonitrile derivative (phthalonitrile compound) represented by general formula (III) is carried out in an organic solvent, the organic solvent used as the main component can be one or more of the following: inert solvents such as benzene, toluene, xylene, nitrobenzene, monochlorobenzene, dichlorobenzene, trichlorobenzene, 1-chloronaphthalene, 1-methylnaphthalene, ethylene glycol, and benzonitrile; and aprotic polar solvents such as pyridine, N,N-dimethylformamide, N-methyl-2-pyrrolidinone, N,N-dimethylacetophenone, triethylamine, tri-n-butylamine, dimethyl sulfoxide, dimethyl sulfone, and sulfolane. Among these, 1-chloronaphthalene, N-methyl-2-pyrrolidone, 1-methylnaphthalene, trimethylbenzene, benzonitrile, nitrobenzene, and ethylene glycol are preferred. Trimethylbenzene and benzonitrile are more preferred. The total amount of solvent used in the cyclization reaction is preferably an amount such that the concentration of the phthalonitrile compound represented by general formula (III) is 1 to 50 mass %, more preferably 10 to 40 mass %, and particularly preferably 20 to 40 mass %. Regarding the above cyclization reaction, the reaction temperature is not necessarily constant depending on the types of raw materials, the type of solvent, and other conditions, but is usually preferably 100 to 300°C. It is more preferably 120°C or higher, and even more preferably 130°C or higher. It is also more preferably 260°C or lower, even more preferably 240°C or lower, and particularly preferably 200°C or lower. The temperature may be increased in stages to control the exothermic reaction. The reaction time is not particularly limited, but is usually preferably within 72 hours, more preferably within 48 hours, even more preferably within 36 hours, and particularly preferably within 24 hours. The phthalocyanine dye obtained by the above-described production method preferably exhibits an absorption maximum in the wavelength range of 640 to 750 nm when the absorption spectrum of a solution containing the phthalocyanine dye is measured. Furthermore, the transmittance at a wavelength of 430 nm is preferably 80% or higher, more preferably 83% or higher, even more preferably 85% or higher, and most preferably 87% or higher. Furthermore, the transmittance at the absorption maximum wavelength in the wavelength range of 640 to 750 nm is preferably 60% or lower, more preferably 50% or lower, even more preferably 40% or lower, and even more preferably 30% or lower. Satisfying these numerical values ​​results in good optical properties, making the dye suitable for use in optical filters. In order to further improve the optical properties, the post-processing steps after the cyclization reaction will be described. Regarding the conditions for introducing a substituent in a reaction in a later step, for example, when a phthalocyanine dye having a substituted amino group is desired, the phthalocyanine dye obtained by the above-mentioned cyclization reaction can be reacted with an aromatic amine such as aniline or benzylamine, or an aliphatic amine such as n-butylamine, n-hexylamine or 2-ethylhexylamine (hereinafter also referred to as an "amino compound"). The amount of the amino compound used is appropriately selected depending on the structure of the target phthalocyanine dye, and is not particularly limited as long as it is an amount that allows the reaction to proceed and the desired phthalonitrile compound to be produced. The amount is usually 1 to 50 mol, preferably 2 to 40 mol, and more preferably 3 to 20 mol, relative to 1 mol of the raw material phthalonitrile compound. The conditions for the substitution reaction with an amino compound are not particularly limited as long as an optimal range is appropriately selected so that the desired substituent can be introduced as designed. For example, the substitution reaction can be carried out by mixing the compounds used in the reaction in the presence of an inert liquid that is not reactive with the compounds used in the reaction, if necessary, and heating to a certain temperature. Preferably, the reaction is carried out by heating to a certain temperature in the amino compound to be reacted. As the inert liquid, for example, nitriles such as benzonitrile and acetonitrile, amides such as N-methylpyrrolidone and dimethylformamide, or halogenated hydrocarbons such as o-chlorotoluene can be used alone or in the form of a mixture of two or more kinds. Furthermore, the amino compound itself can also be used as a solvent for the substitution reaction. The reaction temperature and time for the substitution reaction are not particularly limited as long as they allow the substitution reaction to proceed sufficiently, but the reaction temperature is preferably 40 to 250°C, more preferably 50 to 200°C, even more preferably 60 to 180°C, particularly preferably 60 to 150°C, and most preferably 60 to 120°C, and the reaction time is preferably within 72 hours, more preferably within 48 hours, even more preferably within 36 hours, particularly preferably within 24 hours, and most preferably within 12 hours. After the reaction, the compound can be synthesized by a conventional method using a substitution reaction of a phthalocyanine compound. By filtering out inorganic components and distilling off (washing) the amino compound, the desired phthalocyanine dye can be obtained efficiently and with high purity without going through complicated manufacturing processes. Furthermore, the optical filter containing the phthalocyanine dye obtained by the above-mentioned production method has excellent light selective transmittance and solubility in organic solvents, as described above, and is therefore useful as a green coloring dye for use in the coloring pattern of optical filters, particularly color filters. It is generally difficult to obtain a spectral transmittance spectrum for each colored pattern (pixel) of a color filter using a single material. Therefore, two or more pigments or dyes are often used to obtain a colorant composition. To achieve a bright, high-quality image with a wide color reproduction range, the pigments or dyes must be selected to match the light transmission characteristics of the backlight and must be toned in a certain ratio. For example, the green (G) pixel of a color filter uses a colorant composition toned by selecting two or more green and yellow colorants. Therefore, it is preferable that the colorant contains other colorants in addition to the phthalocyanine dye. Examples of other colorants include pigments and other dyes. Among these, green pigments, green dyes, yellow pigments, yellow dyes, etc. are preferably used for green pixel applications. When combined with a phthalocyanine dye, yellow colorants are particularly preferred, and yellow pigments and / or yellow dyes are even more preferred. It is particularly preferable that the yellow colorant be an azo yellow pigment or an azo yellow dye. Examples of green pigments include CI Pigment Green 7, 36, 58, 59, 62, and 63, with CI Pigment Green 58 being preferred in terms of its ability to enhance brightness. Green dyes, classified as dyes in the Color Index, include CI Solvent Green 1, 3, 4, 5, 7, 28, 29, 32, 33, 34, and 35 as CI Solvent dyes, and CI Acid Green 1, 3, 5, 9, 16, 25, 27, 50, 58, 63, 65, 80, 104, 105, 106, and 109 as CI Acid dyes, and CI Mordant Green 1, 3, 4, 5, 10, 15, 19, 26, 29, 33, 34, 35, 41, 43, and 53 as CI Acid dyes. Yellow pigments include CI Pigment Yellow 1, 1:1, 2, 3, 4, 5, 6, 9, 10, 12, 13, 14, 16, 17, 20, 24, 31, 32, 34, 35, 35: 1, 36, 36:1, 37, 37:1, 40, 41, 42, 43, 48, 53, 55, 61, 62, 62:1, 63, 65, 73, 74, 75, 81, 83, 86, 87, 93, 94, 95, 97, 100, 101, 104, 105, 108, 109, 110, 111, 116, 117, 119, 120, 125, 126, 127, 127:1, 128, 129, 133, 134, 136, 137, 138, 139, 142, 147, 148, 150, 151, 153, 154, 155 , 157, 158, 159, 160, 161, 162, 163, 164, 165, 166, 167, 168, 169, 170, 172, 173, 174, 175, 176, 180, 181, 182, 183, 184, 185, 188, 189, 190, 191, 191:1, 192, 193, 194, 195, 196, 197, 198, 199, 200, 202, 203, 204, 205, 206, 207, 208, and nickel azo yellow pigments represented by the following formula (V):

[0026] [ka] Among these, CI Pigment Yellow 83, 117, 129, 138, 139, 154, 155, 180, 185, and nickel azo yellow pigments represented by formula (V) are preferred in terms of increasing brightness. The yellow dye is preferably at least one dye selected from the group consisting of barbituric acid azo dyes, pyridone azo dyes, pyrazolone azo dyes, quinophthalone dyes, and cyanine dyes, examples of which include the yellow dyes exemplified in JP-A Nos. 2015-61907 and 2012-42898.

[0027] The barbituric acid azo dye is not particularly limited, and known substances can be used, but preferably a barbituric acid azo dye represented by formula (VI) is used.

[0028] [ka] [In formula (VI), T1 and T 2 each independently represents an oxygen atom or a sulfur atom. R 31 ~R 34 each independently represents a hydrogen atom, an aliphatic hydrocarbon group of 1 to 10 carbon atoms which may have a substituent, an aryl group of 6 to 20 carbon atoms which may have a substituent, an aralkyl group of 7 to 20 carbon atoms which may have a substituent, or an acyl group of 2 to 10 carbon atoms which may have a substituent. R 35 ~R 42 each independently represents a hydrogen atom, an aliphatic hydrocarbon group having 1 to 10 carbon atoms, an alkoxyl group having 1 to 8 carbon atoms, a carboxyl group, a sulfo group, a sulfamoyl group, or an N-substituted sulfamoyl group. The hydrogen atom contained in the aliphatic hydrocarbon group may be substituted with a halogen atom.] The pyridone azo dye is not particularly limited, and known substances can be used, but preferably those represented by formula (VII) are used.

[0029] [ka] [In formula (VII), Za represents a phenyl group having one or two substituents selected from the group consisting of a halogen atom, an aliphatic hydrocarbon group having 1 to 12 carbon atoms which may have a substituent, an alkoxyl group having 1 to 8 carbon atoms, a hydroxyl group, a carboxyl group, a carbamoyl group, a sulfo group, a sulfamoyl group, and an N-substituted sulfamoyl group, or a naphthyl group having one to three substituents selected from the group consisting of a halogen atom, an aliphatic hydrocarbon group having 1 to 12 carbon atoms which may have a substituent, an alkoxyl group having 1 to 8 carbon atoms, a hydroxyl group, a carboxyl group, a carbamoyl group, a sulfo group, a sulfamoyl group, and an N-substituted sulfamoyl group. R 21 represents a hydrogen atom, a linear, branched or cyclic aliphatic hydrocarbon group having 1 to 10 carbon atoms, a carboxyl group or a trifluoromethyl group. R 22represents a hydrogen atom, a cyano group, a carbamoyl group, an N-substituted carbamoyl group, a sulfamoyl group, or a sulfo group. R 23 represents a hydrogen atom, a linear, branched or cyclic aliphatic hydrocarbon group of 1 to 10 carbon atoms which may have a substituent, an aryl group of 6 to 30 carbon atoms which may have a substituent, an aralkyl group of 7 to 20 carbon atoms which may have a substituent, a heterocyclic group of 3 to 20 carbon atoms which may have a substituent, a carbamoyl group, an N-substituted carbamoyl group, an alkyloxycarbonyl group of 2 to 20 carbon atoms which may have a substituent, an aryloxycarbonyl group of 7 to 30 carbon atoms which may have a substituent, an acyl group of 2 to 20 carbon atoms which may have a substituent, an aliphatic sulfonyl group of 1 to 30 carbon atoms which may have a substituent, or an arylsulfonyl group of 6 to 30 carbon atoms which may have a substituent. In formula (VII), the aliphatic hydrocarbon group having 1 to 12 carbon atoms represented by Za may be linear, branched, or cyclic. The number of carbon atoms in the aliphatic hydrocarbon group includes the number of carbon atoms of all substituents, and is generally 1 to 12, preferably 2 to 11. Examples of the aliphatic hydrocarbon group include an n-octyl group, a methylhexyl group (e.g., 1,5-dimethylhexyl group), an ethylhexyl group (e.g., 2-ethylhexyl group), a cyclooctyl group, a methylcyclohexyl group (e.g., 2,2-dimethylcyclohexyl group), and a cyclohexylalkyl group. A hydrogen atom contained in the aliphatic hydrocarbon group may be substituted with an alkoxyl group or a carboxyl group having 1 to 8 carbon atoms. Examples of the substituted aliphatic hydrocarbon group include an alkoxypropyl group (e.g., 3-(2'-ethylhexyloxy)propyl group) and an 8-(carboxy)octyl group. Examples of the alkoxyl group having 1 to 8 carbon atoms for Za include a methoxy group, an ethoxy group, an isopropoxy group, an n-propoxy group, an n-butoxy group, an isobutoxy group, a sec-butoxy group, and a tert-butoxy group. Examples of the halogen atom in Za include a fluorine atom, a bromine atom, a chlorine atom, and an iodine atom. The N-substituted sulfamoyl group in Za is -SO2N(R24 )R 25 It is expressed as: R 24 and R 25 each independently represents a hydrogen atom, an aliphatic hydrocarbon group having 1 to 16 carbon atoms which may have a substituent, an aryl group having 6 to 20 carbon atoms which may have a substituent, an aralkyl group having 7 to 20 carbon atoms which may have a substituent, or an acyl group having 2 to 15 carbon atoms which may have a substituent (provided that R 24 and R 25 but never simultaneously be a hydrogen atom). The aliphatic hydrocarbon group having 1 to 16 carbon atoms may be linear, branched, or cyclic, and the aliphatic hydrocarbon group preferably has 6 to 16 carbon atoms. R 24 and R 25 The aliphatic hydrocarbon group having 1 to 16 carbon atoms may be linear, branched, or cyclic. The number of carbon atoms in the aliphatic hydrocarbon group does not include the number of carbon atoms in the substituents, and the number is usually 1 to 16, preferably 6 to 10. Examples of the aliphatic hydrocarbon group include a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group, a sec-butyl group, a tert-butyl group, a methylbutyl group (e.g., a 1,1,3,3-tetramethylbutyl group), a methylhexyl group (e.g., a 1,5-dimethylhexyl group), an ethylhexyl group (e.g., a 2-ethylhexyl group), a cyclopentyl group, a cyclohexyl group, a methylcyclohexyl group (e.g., a 2-methylcyclohexyl group), and a cyclohexylalkyl group. A hydrogen atom contained in the aliphatic hydrocarbon group may be substituted with an alkoxyl group or a carboxyl group having 1 to 8 carbon atoms. Examples of the substituted aliphatic hydrocarbon group include a propoxypropyl group (such as a 3-(isopropoxy)propyl group), a 2-(carboxy)ethyl group, a 3-(carboxy)ethyl group, and a 4-carboxyethyl group. R 24 and R 25In the above formula, the aryl group having 6 to 20 carbon atoms may have a substituent such as an aliphatic hydrocarbon group or a hydroxyl group. The number of carbon atoms in the aryl group, counted including the number of carbon atoms in the substituent, is usually 6 to 20, and preferably 6 to 10. Examples of the aryl group include a phenyl group, a carboxyphenyl group (such as a 2-carboxyphenyl group or a 2,4-carboxyphenyl group), a hydroxyphenyl group (such as a 4-hydroxyphenyl group), a trifluoromethylphenyl group (such as a 4-trifluoromethylphenyl group), and a methoxyphenyl group (such as a 4-methoxyphenyl group). R 24 and R 25 The alkyl moiety of the aralkyl group having 7 to 20 carbon atoms in the formula (I) may be either linear or branched. The number of carbon atoms in the aralkyl group is usually 7 to 20, and preferably 7 to 10. Examples of aralkyl include benzyl group, phenylethyl group (2-phenylethyl group, 2-(4-hydroxyphenyl)ethyl group, etc.), phenylethylene group (2-phenylethyl group, 2-(4-hydroxyphenyl)ethyl group, etc.), and the like. phenylalkyl groups such as phenylethylene groups, phenylpropyl groups (1-methyl-3-phenylpropyl groups, etc.), and phenylbutyl groups (3-amino-1-phenylbutyl groups, etc.). R 24 and R 25 The acyl group having 2 to 15 carbon atoms in the formula (I) may be unsubstituted or may have a substituent such as an aliphatic hydrocarbon group, an alkoxyl group, or a carboxyl group. The number of carbon atoms in the acyl group is counted including the number of carbon atoms in the substituent, and is usually 2 to 15, and preferably 6 to 10. Examples of the acyl group include an acetyl group, a benzoyl group, a methoxybenzoyl group (such as a p-methoxybenzoyl group), a carboxyacetyl group, a 2-carboxypropionyl group, a 3-carboxypropionyl group, a 2-carboxybutyryl group, a 3-carboxybutyryl group, and a 4-carboxybutyryl group. R 21 represents a hydrogen atom, a linear, branched or cyclic aliphatic hydrocarbon group having 1 to 10 carbon atoms, a carboxyl group or a trifluoromethyl group. R 21The number of carbon atoms in the aliphatic hydrocarbon group having 1 to 10 carbon atoms in the formula does not include the number of carbon atoms in the substituent. The number of carbon atoms is preferably 2 to 8, and more preferably 3 to 6. Examples of the aliphatic hydrocarbon group include a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group, a sec-butyl group, a tert-butyl group, a cyclopentyl group, and a cyclohexyl group. R 22 represents a hydrogen atom, a cyano group, a carbamoyl group or an N-substituted carbamoyl group, a sulfamoyl group or a sulfo group. R 22 The N-substituted carbamoyl group in 26 )R 27 Examples include: R 26 and R 27 each independently represents a hydrogen atom, an aliphatic hydrocarbon group of 1 to 10 carbon atoms which may have a substituent, an aryl group of 6 to 20 carbon atoms which may have a substituent, an aralkyl group of 7 to 20 carbon atoms which may have a substituent, or an acyl group of 2 to 10 carbon atoms which may have a substituent. R 26 and R 27 The explanation and specific examples of the aliphatic hydrocarbon group, aryl group, aralkyl group and acyl group are given in the above R 24 and R 25 The acyl group may have a halogen atom. Examples of the acyl group having a halogen atom include a bromobenzoyl group (e.g., a p-bromobenzoyl group). R 23represents a hydrogen atom, a linear, branched or cyclic aliphatic hydrocarbon group of 1 to 10 carbon atoms which may have a substituent, an aryl group of 6 to 30 carbon atoms which may have a substituent, an aralkyl group of 7 to 20 carbon atoms which may have a substituent, a heterocyclic group of 3 to 20 carbon atoms which may have a substituent, a carbamoyl group, an N-substituted carbamoyl group, an alkyloxycarbonyl group of 2 to 20 carbon atoms which may have a substituent, an aryloxycarbonyl group of 7 to 30 carbon atoms which may have a substituent, an acyl group of 2 to 20 carbon atoms which may have a substituent, an aliphatic sulfonyl group of 1 to 30 carbon atoms which may have a substituent, or an arylsulfonyl group of 6 to 30 carbon atoms which may have a substituent. R 23 The aliphatic hydrocarbon group in 21 The aliphatic hydrocarbon groups are the same as those in the above. R 23 The aryl group in the formula (I) has usually 6 to 30 carbon atoms, preferably 6 to 20 carbon atoms, and more preferably 6 to 16 carbon atoms. Specific examples of the aryl group include a phenyl group, a 4-nitrophenyl group, a 2-nitrophenyl group, a 2-chlorophenyl group, a 2,4-dichlorophenyl group, a 2,4-dimethylphenyl group, a 2-methylphenyl group, a 4-methanphenyl group, a 2-isopropyl ... Examples include a 2-methoxyphenyl group, a 2-methoxycarbonyl-4-nitrophenyl group, and the like. R 23 The aralkyl group in may be either linear or branched, and the number of carbon atoms is preferably 7 to 10. Specific examples of the aralkyl include phenylalkyl groups such as benzyl group, phenylpropyl group (e.g., 1-methyl-3-phenylpropyl group), and phenylbutyl group (e.g., 3-amino-1-phenylbutyl group). R 23The heterocyclic group having 3 to 20 carbon atoms in the formula (I) may be saturated or unsaturated, and preferably has 3 to 20 carbon atoms, more preferably 5 to 15. Specific examples of the heterocyclic group include a pyrazole group, a 1,2,4-triazole group, an isothiazole group, a benzisothiazole group, a thiazole group, a benzothiazole group, an oxazole group, and a 1,2,4-thiadiazole group. Furthermore, the heterocyclic group may further have a substituent. R 23 The N-substituted carbamoyl group in 22 is the same as the N-substituted carbamoyl group described above. R 23 The alkyloxycarbonyl group in the formula (I) may be unsubstituted or substituted, and may be cyclic. The number of carbon atoms in the alkyloxycarbonyl group is usually 2 to 20, preferably 2 to 16, and more preferably 2 to 10. Examples of the alkyloxycarbonyl group include a methoxycarbonyl group, an ethoxycarbonyl group, and a butoxycarbonyl group. R 23 The aryloxycarbonyl group in the formula (I) may be unsubstituted or substituted, and has a carbon number of usually 7 to 30, preferably 7 to 20, and more preferably 7 to 16. Examples of the aryloxycarbonyl group include a phenoxycarbonyl group and a 4-methylphenoxycarbonyl group. R 23 The acyl group in may be an aliphatic carbonyl group or an arylcarbonyl group, may be saturated or unsaturated, may be cyclic, and may further have a substituent. The number of carbon atoms is usually 2 to 20, preferably 2 to 15, and more preferably 2 to 10. Examples of the acyl group include an acetyl group, a propionyl group, a butyryl group, an isobutyryl group, a valeryl group, an isovaleryl group, a pivaloyl group, and a benzoyl group. R 23The aliphatic sulfonyl group in may be saturated or unsaturated, and may be cyclic. The number of carbon atoms is usually 1 to 30, preferably 1 to 20, and more preferably 1 to 16. Examples of the aliphatic sulfonyl group include a methanesulfonyl group, a butanesulfonyl group, a methoxymethanesulfonyl group, a methoxyethanesulfonyl group, and an ethoxyethanesulfonyl group. R 23 The arylsulfonyl group in the formula (I) may have a substituent, and has usually 6 to 30 carbon atoms, preferably 6 to 20, and more preferably 6 to 18. Examples of the arylsulfonyl group include a benzenesulfonyl group and a toluenesulfonyl group. The compound represented by formula (VII) may form any of an ammonium salt, a lithium salt, a sodium salt, and a potassium salt. The compound represented by formula (VII) may form a dimer or higher multimer. Specifically, examples of pyridone azo dyes include the compounds described in JP-A No. 2015-61907 (paragraphs 0070 to 0072). In addition, the pyrazolone azo dye is not particularly limited, and known substances can be used. For example, pyrazolone azo dyes described in JP-A Nos. 2006-276512, 2005-263926, and 2006-015669 can be used. The quinophthalone dye is not particularly limited, and known substances can be used, such as the quinophthalone dyes described in JP-A Nos. 5-39269, 6-220339, and 8-171201. Furthermore, the cyanine dye is not particularly limited, and known substances can be used, such as cyanine dyes described in JP-A Nos. 2005-194509, 2007-131818, and 2005-297406. Among these, pyridone azo dyes (yellow) are preferred from the viewpoint of improving brightness, as will be described in detail below. The number of azo groups (-N=N-) contained in the pyridone azo (yellow) dye is preferably 1 to 3, more preferably 1 to 2, and even more preferably 1, and it is preferable that the azo group be present in the structure of the pyridone azo colorant. Furthermore, in the colored photosensitive resin composition of the present invention, a pyridone azo yellow colorant represented by the following chemical formula (VII-1) or (VII-2) is most preferably used, which, when toned with the above-mentioned phthalocyanine dye, improves the brightness of green pixels in LCD televisions. When the following pyridone azo yellow colorant is used, a colored photosensitive resin composition with high colorfastness can be obtained. Furthermore, the spectrum has a sharp rise in the vicinity of 450 to 500 nm, which is preferable from the viewpoint of high yellow color purity. The pyridone azo yellow dyes (VII-1) and (VII-2) are specifically shown below. Chemical formula (VII-1):

[0030] [ka] (In the formula, R 43 ~R 47 and each independently represent a hydrogen atom, or an alkyl group having 1 to 21 carbon atoms, an alkenyl group having 2 to 21 carbon atoms, an aryl group having 6 to 21 carbon atoms, or an aralkyl group having 7 to 21 carbon atoms, which may have a substituent. Chemical formula (VII-2):

[0031] [ka] (In the formula, R 43 ~R 47 and each independently represent a hydrogen atom, or an alkyl group having 1 to 21 carbon atoms, an alkenyl group having 2 to 21 carbon atoms, an aryl group having 6 to 21 carbon atoms, or an aralkyl group having 7 to 21 carbon atoms, which may have a substituent. In the above formulas (VII-1) and (VII-2), R 43 ~R 47are each independently a hydrogen atom, or an alkyl group having 1 to 21 carbon atoms, an alkenyl group having 2 to 21 carbon atoms, an aryl group having 6 to 21 carbon atoms, or an aralkyl group having 7 to 21 carbon atoms, which may have a substituent.

[0032] In the present invention, the sulfonamide group in formula (VII-1) and the carboxamide group in formula (VII-2) may be bonded to the -N=N- double bond group (azo group) in the benzene ring to which they are bonded, at any of the ortho, para, or meta positions. From the viewpoint of solvent solubility, the para position is preferred, and from the viewpoint of shortening the wavelength of the waveform and improving color purity, the ortho or meta position is preferred.

[0033] In the present invention, R in formula (VII-1) and formula (VII-2) 47 may be bonded to any of the ortho, para, or meta positions of the -N=N- double bond group (azo group) in the benzene ring to which it is bonded. From the viewpoint of solvent solubility, however, the ortho or para position is preferred, and the ortho position is more preferred.

[0034] In the present invention, R 43 ~R 47 The alkyl group having 1 to 21 carbon atoms represented by the following formula may be unsubstituted or may have a substituent. The alkyl group is preferably an alkyl group having 1 to 15 carbon atoms, and more preferably an alkyl group having 1 to 10 carbon atoms.

[0035] R 43 ~R 47The alkyl group having 1 to 21 carbon atoms, represented by the formula (I), may be any of a linear, branched, or cyclic alkyl group, and examples thereof include a methyl group, an ethyl group, an n-propyl group, an n-butyl group, an n-amyl group, an n-hexyl group, an n-heptyl group, an n-octyl group, an n-nonyl group, an n-decyl group, an n-undecyl group, an n-dodecyl group, an n-tridecyl group, an n-tetradecyl group, an n-pentadecyl group, an n-hexadecyl group, an n-heptadecyl group, an n-octadecyl group, an n-nonadecyl group, an n-eicosanyl group, an i-propyl group, a sec-butyl group, an i-butyl group, a t-butyl group, a 1-methylbutyl group, a 1-ethylpropyl group, a 2-methylbutyl group, an i-amyl group, a neopentyl group, a 1,2-dimethylpropyl group, a 1,1-dimethylpropyl group, a t-amyl group, a 1,3-dimethylbutyl group, a 3,3-dimethyl Preferred examples of the alkyl group include linear, branched, and cyclic hydrocarbon groups such as a butyl group, a 2-ethylbutyl group, a 2-ethyl-2-methylpropyl group, a 1-methylheptyl group, a 2-ethylhexyl group, a 1,5-dimethylhexyl group, a t-octyl group, a branched nonyl group, a cyclopropyl group, a cyclopropylmethyl group, a cyclobutyl group, a cyclobutylmethyl group, a cyclopentyl group, a cyclohexyl group, a cyclohexylmethyl group, a cycloheptyl group, a cyclooctyl group, a cyclohexylpropyl group, a cyclododecyl group, a norbornyl group, a bornyl group, a cis-myrtanyl group, an isopinocamphenyl group, a noradamantyl group, an adamantyl group, an adamantylmethyl group, a 1-(1-adamantyl)ethyl group, a 3,5-dimethyladamantyl group, a quinuclidinyl group, a cyclopentylethyl group, and a bicyclooctyl group.

[0036] In the present invention, R 43 ~R 47 The alkenyl group having 2 to 21 carbon atoms represented by the following formula may be unsubstituted or may have a substituent. The alkenyl group is preferably an alkenyl group having 2 to 15 carbon atoms, and more preferably an alkenyl group having 2 to 10 carbon atoms.

[0037] R 43 ~R 47Examples of the alkenyl group having 2 to 21 carbon atoms represented by the formula (I) include a vinyl group, an isopropenyl group, a 2-propenyl group, a 2-methyl-propenyl group, a 1-methyl-1-propenyl group, a 1-butenyl group, a 3-butenyl group, a 1-methyl-1-butenyl group, a 1,1-dimethyl-3-butenyl group, a 1-pentenyl group, a 2-pentenyl group, a 1-ethyl-1-pentenyl group, a 1-hex ... Preferred examples thereof include butenyl group, 2,6-dimethyl-5-heptenyl group, 9-decenyl group, 1-cyclopentenyl group, 2-cyclopentenylmethyl group, cyclohexenyl group, 1-methyl-2-cyclohexenyl group, 1,4-dihydro-2-methylphenyl group, octenyl group, citronellyl group, oleyl group, geranyl group, farnesyl group, and 2-(1-cyclohexenyl)ethyl group. In the present invention, R 43 ~R 47 The aryl group having 6 to 21 carbon atoms, represented by the following formula (I), may be unsubstituted or may have a substituent. The aryl group is preferably an aryl group having 6 to 15 carbon atoms, more preferably an aryl group having 6 to 10 carbon atoms.

[0038] Suitable examples of the aryl group having 6 to 21 carbon atoms include a phenyl group, a naphthyl group, a biphenylenyl group, an acenaphthenyl group, a fluorenyl group, an anthracenyl group, an anthraquinonyl group, and a pyrenyl group. Among these, a phenyl group, a naphthyl group, a biphenylenyl group, an acenaphthenyl group, a fluorenyl group, and an anthracenyl group are more preferred, and a phenyl group, a naphthyl group, a biphenylenyl group, and a fluorenyl group are particularly preferred.

[0039] In the present invention, R 43 ~R 47 The aralkyl group having 7 to 21 carbon atoms, represented by the following formula (I), may be unsubstituted or may have a substituent. As the aralkyl group, an aralkyl group having 7 to 15 carbon atoms is preferable, and an aralkyl group having 7 to 10 carbon atoms is more preferable.

[0040] R 43 ~R 47Suitable examples of the aralkyl group having 7 to 21 carbon atoms represented by the formula (I) include a benzyl group, a diphenylmethyl group, a 1,2-diphenylethyl group, a phenylcyclopentylmethyl group, an α-methylbenzyl group, a phenylethyl group, an α-methylphenylethyl group, a β-methylphenylethyl group, a 3-phenylpropyl group, a 3,3-diphenylpropyl group, a 4-phenylbutyl group, a naphthylmethyl group, a styryl group, a cinnamyl group, a fluorenyl group, a 1-benzocyclobutenyl group, a 1,2,3,4-tetrahydronaphthyl group, an indanyl group, a piperonyl group, and a pyrenemethyl group.

[0041] R 43 ~R 47 When the group represented by the formula (I) has a substituent, the substituent may be an acyl group, an acylamino group, an acylaminocarbonylamino group, an aralkylaminocarbonylamino group, an arylaminocarbonylamino group, a methacryloylaminocarbonylamino group, an alkoxycarbonyl group, a hydroxyalkyloxy group (-O-(CH2) n —OH), trifluoromethyl group, fluoro group, chloro group, bromo group, iodo group, hydroxy group, nitro group, methyl group, ethyl group, n-propyl group, i-propyl group, n-butyl group, i-butyl group, sec-butyl group, t-butyl group, pentyl group, hexyl group, heptyl group, octyl group, vinyl group, methoxy group, ethoxy group, butoxy group, isopropoxy group, t-butoxy group, cyclohexyloxy group, vinyloxy group, methylthio group, ethylthio group, pyrrolidinyl group, piperidinyl group, piperazinyl group, amino group, dimethylamino group, diethylamino group, phenyl group, —SOM group, and —COOM group (wherein M represents a hydrogen atom, a metal atom, or a cation composed of a nitrogen-containing compound) are preferred. Among these, the substituent is preferably a hydroxyalkyloxy group, a fluoro group, a chloro group, a bromo group, an iodo group, a hydroxy group, a nitro group, a methyl group, an ethyl group, an n-propyl group, an i-propyl group, an n-butyl group, an i-butyl group, a sec-butyl group, a t-butyl group, a pentyl group, a hexyl group, a heptyl group, an octyl group, a methoxy group, an ethoxy group, a butoxy group, an isopropoxy group, a t-butoxy group, or a phenyl group, and more preferably a hydroxyalkyloxy group, a hydroxy group, a methyl group, an ethyl group, an n-propyl group, an i-propyl group, an n-butyl group, an i-butyl group, a sec-butyl group, a t-butyl group, a pentyl group, a hexyl group, a heptyl group, an octyl group, a methoxy group, an ethoxy group, a butoxy group, an isopropoxy group, a t-butoxy group, or a phenyl group.

[0042] The above-mentioned substituents may be further substituted multiple times with the same substituents. In the sulfamoyl compound of formula (VII-1), R 45 and R 46 A straight or branched alkyl chain having a total carbon number of preferably 4 or more, more preferably 6 or more, even more preferably 8 or more, and particularly preferably 8 to 14 is preferred in terms of high solubility in solvents.

[0043] Also, R 45 or R 46 It is also preferable that R contains an ether bond, since it has high solubility in solvents. 45 or R 46 When an ether bond is contained in the alkyl chain, it is preferable that the linear or branched alkyl chains are mutually bonded via an ether bond (-O-). In this case, the alkyl chain is expressed as "-X1-O-X2," where X1 represents an alkylene group and X2 represents an alkyl group. In this case, the total number of carbon atoms in the alkyl chains bonded via the ether bond (the total number of carbon atoms in X1 and X2) is preferably 3 or more, more preferably 4 or more. In this case, the total number of carbon atoms is preferably 21 or less, more preferably 16 or less, even more preferably 14 or less, and particularly preferably 10 or less.

[0044] In addition, since the colorfastness improves as the alkyl chain becomes longer, R 45 and R 46 The total number of carbon atoms is preferably 4 or more, more preferably 6 or more, even more preferably 8 or more, and particularly preferably 8 to 14, and is a straight or branched alkyl chain.

[0045] Furthermore, in the sulfamoyl compound of formula (VII-1), R 43 is preferably a linear or branched alkyl chain having 2 or more carbon atoms, particularly preferably 4 to 8 carbon atoms, from the viewpoint of high solubility in solvents. It is also preferable if this alkyl chain contains an ether bond (-O-) or a hydroxyl group (-OH).

[0046] In addition, in the sulfamoyl compound of chemical formula (VII-1), R 44 is a straight or branched alkyl chain having 1 or more carbon atoms, particularly preferably 1 to 6 carbon atoms, from the viewpoint of high solubility in solvents. In the composition of the present invention, the yellow coloring compound preferably used is a compound represented by the following formula: It goes without saying that the yellow coloring compound is not limited to this.

[0047] [ka]

[0048] [ka] The content of the colorant in the colored photosensitive resin composition of the present invention is not particularly limited, but is preferably 5% by mass or more, more preferably 10% by mass or more, even more preferably 15% by mass or more, even more preferably 20% by mass or more, and particularly preferably 30% by mass or more, and is preferably 70% by mass or less, more preferably 60% by mass or less, even more preferably 50% by mass or less, even more preferably 45% by mass or less, and particularly preferably 40% by mass or less, based on the total solid content of the colored photosensitive resin composition. By setting the content at or above the lower limit, color properties tend to be improved, and by setting the content at or below the upper limit, pattern formability tends to be good. The content of the phthalocyanine dye, an essential component of the colorant, is not particularly limited, but is preferably 4% by mass or more, more preferably 6% by mass or more, even more preferably 8% by mass or more, particularly preferably 10% by mass or more, and is preferably 45% by mass or less, more preferably 40% by mass or less, even more preferably 35% by mass or less, even more preferably 30% by mass or less, and particularly preferably 25% by mass or less, relative to 100% by mass of the total solids content of the colored photosensitive resin composition. Setting the content at or above the lower limit tends to improve color characteristics such as brightness, while setting the content at or below the upper limit tends to ensure sufficient solubility and good pattern formability. When using a phthalocyanine dye alone as a colorant, this is preferred because it results in high color purity. When using other colorants to be toned, this is preferred because it makes it easier to adjust the chromaticity coordinates (x, y) in the CIE color system to the desired values. When other colorants are contained, their content is not particularly limited, but is preferably 1% by mass or more, more preferably 4% by mass or more, even more preferably 6% by mass or more, even more preferably 8% by mass or more, particularly preferably 10% by mass or more, and preferably 40% by mass or less, more preferably 35% by mass or less, even more preferably 30% by mass or less, and particularly preferably 25% by mass or less, based on the total solid content of the colored photosensitive resin composition. By setting the content at or above the lower limit, it becomes easy to adjust the chromaticity coordinate values ​​(x, y) in the CIE color system to the desired values, and by setting the content at or below the upper limit, compatibility can be maintained and pattern formability tends to be good. The amount of the yellow colorant compound (yellow colorant) preferably contained in the present invention is not particularly limited, but is preferably 0.01 to 50 parts by mass, more preferably 0.5 to 40 parts by mass, and even more preferably 1 to 30 parts by mass, relative to 100% by mass of the total solid content of the colored photosensitive resin composition. The blending amounts of the phthalocyanine dye and the yellow coloring compound (yellow coloring material) are not particularly limited, but when the phthalocyanine dye used in the present invention is taken as 100 parts by mass, the yellow coloring compound is preferably 0.01 to 400 parts by mass, more preferably 1 to 300 parts by mass, even more preferably 5 to 250 parts by mass, and particularly preferably 10 to 200 parts by mass. When the phthalocyanine dye is a mixture of two or more kinds, the total amount is taken as the mass of the phthalocyanine dye.

[0049] The above yellow colorant compounds (yellow colorants) may be used alone or in combination of two or three. Using two or three types of colorants improves the solubility of each of the colorants, which may result in improved color purity and improved brightness as a color filter. [Alkali-soluble resin] The alkali-soluble resin used in the present invention is preferably a polymer exhibiting alkali solubility, and particularly preferably one having a weight-average molecular weight of 5,000 or more. Use of one having a weight-average molecular weight of 5,000 or more significantly improves developability. The weight-average molecular weight is preferably 7,000 or more, more preferably 10,000 or more, and even more preferably 12,000 or more. Furthermore, from the viewpoint of viscosity and the like, the weight-average molecular weight is preferably 250,000 or less. The weight-average molecular weight is more preferably 100,000 or less, even more preferably 50,000 or less, particularly preferably 30,000 or less, and most preferably 20,000 or less. When the alkali-soluble resin has a high molecular weight, the higher the acid value, the easier it is to develop. The weight average molecular weight can be determined, for example, by GPC (gel permeation chromatography) using polystyrene as a standard substance, tetrahydrofuran as an eluent, HLC-8320GPC (manufactured by Tosoh Corporation) and a column TSKgel SuperHZM-M (manufactured by Tosoh Corporation).

[0050] The alkali-soluble resin (preferably an alkali-soluble polymer) is also preferably a polymer having an acid group in the molecule (also referred to as an "acid group-containing polymer"). Examples of the acid group include functional groups that undergo a neutralization reaction with alkaline water, such as a carboxyl group, a phenolic hydroxyl group, a carboxylic anhydride group, a phosphoric acid group, and a sulfonic acid group, and the resin may have only one of these groups or two or more of these groups. Among these, a carboxyl group or a carboxylic anhydride group is preferred, and a carboxyl group is more preferred. When the alkali-soluble polymer is a polymer having an acid group, the acid value (AV) of the alkali-soluble polymer is not particularly limited, but is preferably, for example, 20 mgKOH / g or more and less than 300 mgKOH / g. This allows for more sufficient alkali solubility to be exhibited, making it possible to obtain a cured film with better developability. The lower limit of the acid value is more preferably 30 mgKOH / g or more, even more preferably 40 mgKOH / g or more, and most preferably 100 mgKOH / g or more. It is more preferably 250 mgKOH / g or less, even more preferably 200 mgKOH / g or less. The acid value of the polymer can be determined, for example, by measuring the acid value of the polymer solution using a 0.1N KOH aqueous solution as a titrant with an automatic titrator (manufactured by Hiranuma Sangyo Co., Ltd., product name "COM-1700A") and calculating the acid value per solid content from the acid value of the solution and the solid content of the solution. The solid content of the polymer solution can also be determined as follows. Approximately 0.3 g of the polymer solution was weighed out into an aluminum cup, and approximately 1 g of acetone was added to dissolve the solution, followed by natural drying at room temperature. The solution was then dried at 140°C for 3 hours using a hot air dryer (manufactured by Espec Corporation, product name "PHH-101"), and then allowed to cool in a desiccator, after which the mass was measured. The solids concentration of the polymer solution was calculated from the amount of mass loss. Evaluations were performed according to the methods described in the evaluation methods (1) to (3) in the Examples. The alkali-soluble polymer is preferably, for example, a polymer (also referred to as a base polymer) obtained by polymerizing a monomer component containing a monomer having an acid group and a polymerizable double bond, or a polymer (also referred to as a side-chain double-bond-containing polymer) obtained by reacting the base polymer with a compound having a functional group capable of bonding to an acid group and a polymerizable double bond, as described below. More preferably, it is a polymer having a polymerizable double bond in the side chain (side-chain double-bond-containing polymer). Each of the monomers used may be used alone or in combination of two or more. The alkali-soluble polymer is particularly preferably a polymer having a ring structure in the main chain. When a polymer having a ring structure in the main chain is used as the alkali-soluble polymer, a cured film can be obtained that is more excellent in heat resistance, surface hardness, and adhesion, and can more stably exhibit various physical properties. Thus, an embodiment in which the alkali-soluble polymer is a polymer having a ring structure in the main chain is also one of the preferred embodiments of the present invention. Therefore, it is preferable that the monomer components forming the base polymer contain, in addition to a monomer having an acid group and a polymerizable double bond, one or more monomers capable of introducing a ring structure into the main chain skeleton of the polymer. Examples of the monomer capable of introducing a ring structure into the main chain skeleton of the polymer include a monomer having a double bond-containing ring structure in the molecule and a monomer that undergoes cyclopolymerization to form a polymer having a ring structure in the main chain.

[0051] Examples of the monomer having an acid group and a polymerizable double bond include unsaturated monocarboxylic acids such as (meth)acrylic acid, crotonic acid, cinnamic acid, and vinylbenzoic acid; unsaturated polycarboxylic acids such as maleic acid, fumaric acid, itaconic acid, citraconic acid, and mesaconic acid; unsaturated monocarboxylic acids in which the unsaturated group and the carboxyl group are chain-extended, such as mono(2-acryloyloxyethyl) succinate and mono(2-methacryloyloxyethyl) succinate; unsaturated acid anhydrides such as maleic anhydride and itaconic anhydride; and phosphoric acid group-containing unsaturated compounds such as Light Ester P-1M (manufactured by Kyoeisha Chemical Co., Ltd.). Among these, from the viewpoints of versatility, availability, and the like, it is preferable to use carboxylic acid-based monomers (unsaturated monocarboxylic acids, unsaturated polycarboxylic acids, and unsaturated acid anhydrides). More preferably, in terms of reactivity, alkali solubility, etc., it is preferable to use unsaturated monocarboxylic acids, and even more preferably (meth)acrylic acid (i.e., acrylic acid and / or methacrylic acid), and among these, methacrylic acid is particularly preferred. That is, an alkali-soluble polymer having a structural unit derived from methacrylic acid is particularly preferred. The structural unit derived from methacrylic acid refers to a site in a polymer into which a structure derived from methacrylic acid has been introduced by a polymerization reaction or addition reaction of methacrylic acid. The content of the monomer having an acid group and a polymerizable double bond is preferably, for example, 5% by mass or more relative to 100% by mass of the base polymer component. This provides sufficient alkali solubility, resulting in a colored photosensitive resin composition useful as a color filter resist, which requires developability. Furthermore, in order to further maintain the excellent appearance and adhesion of the cured film, the content is preferably 85% by mass or less. It is more preferably 10 to 80% by mass, and even more preferably 15 to 75% by mass. The monomer component may contain, in addition to the above-mentioned monomer having an acid group and a polymerizable double bond, other radically polymerizable monomers (hereinafter also referred to as "other monomers"). As the other monomer, for example, as described above, one or more monomers capable of introducing a ring structure into the main chain skeleton of the polymer, such as a monomer having a double bond-containing ring structure in the molecule or a monomer that undergoes cyclopolymerization to form a polymer having a ring structure in the main chain, are suitable. As such a monomer, it is preferred to use at least one selected from the group consisting of N-substituted maleimide monomers, dialkyl-2,2'-(oxydimethylene)diacrylate monomers, and α-(unsaturated alkoxyalkyl)acrylates. A preferred embodiment of the present invention is one in which the alkali-soluble resin (alkali-soluble polymer) is a polymer having N-substituted maleimide monomer units, dialkyl-2,2'-(oxydimethylene)diacrylate monomer units, and / or α-(unsaturated alkoxyalkyl)acrylate monomer units. As the other monomer, one or more of other (meth)acrylic acid ester-based monomers and aromatic vinyl-based monomers can also be suitably used. In particular, a polymer containing an N-substituted maleimide monomer unit and / or a dialkyl-2,2'-(oxydimethylene)diacrylate monomer unit can provide a cured film having excellent heat resistance and improved hardness, etc. The polymer containing the above-mentioned monomer unit means, for example, a polymer containing a structural unit derived from the monomer through a polymerization reaction or crosslinking reaction of the monomer. In the above-mentioned monomer component, examples of the N-substituted maleimide monomer include N-cyclohexylmaleimide, N-phenylmaleimide, N-methylmaleimide, N-ethylmaleimide, N-isopropylmaleimide, Nt-butylmaleimide, N-dodecylmaleimide, N-benzylmaleimide, and N-naphthylmaleimide, and one or more of these can be used. Among them, N-cyclohexylmaleimide, N-phenylmaleimide, and N-benzylmaleimide are preferred, and N-benzylmaleimide is particularly preferred, in terms of low coloration and excellent dispersibility. Examples of the N-benzylmaleimide include benzylmaleimide; alkyl-substituted benzylmaleimides such as p-methylbenzylmaleimide and p-butylbenzylmaleimide; phenolic hydroxyl group-substituted benzylmaleimides such as p-hydroxybenzylmaleimide; and halogen-substituted benzylmaleimides such as o-chlorobenzylmaleimide, o-dichlorobenzylmaleimide and p-dichlorobenzylmaleimide. As the dialkyl-2,2'-(oxydimethylene)diacrylate monomer, it is preferable to use, for example, dimethyl-2,2'-[oxybis(methylene)]bis-2-propenoate, etc., from the viewpoints of low coloration, dispersibility, ease of industrial availability, etc. Examples of the α-(unsaturated alkoxyalkyl)acrylate include α-allyloxymethylacrylic acid, methyl α-allyloxymethylacrylate, ethyl α-allyloxymethylacrylate, n-propyl α-allyloxymethylacrylate, i-propyl α-allyloxymethylacrylate, n-butyl α-allyloxymethylacrylate, s-butyl α-allyloxymethylacrylate, t-butyl α-allyloxymethylacrylate, n-amyl α-allyloxymethylacrylate, s-amyl α-allyloxymethylacrylate, t-amyl α-allyloxymethylacrylate, neopentyl α-allyloxymethylacrylate, n-hexyl α-allyloxymethylacrylate, s-hexyl α-allyloxymethylacrylate, n-heptyl α-allyloxymethylacrylate, n-octyl α-allyloxymethylacrylate, s-octyl α-allyloxymethylacrylate, Preferred are α-(allyloxymethyl)acrylates containing a chain saturated hydrocarbon group, such as t-octyl α-allyloxymethylacrylate, 2-ethylhexyl α-allyloxymethylacrylate, capryl α-allyloxymethylacrylate, nonyl α-allyloxymethylacrylate, decyl α-allyloxymethylacrylate, undecyl α-allyloxymethylacrylate, lauryl α-allyloxymethylacrylate, tridecyl α-allyloxymethylacrylate, myristyl α-allyloxymethylacrylate, pentadecyl α-allyloxymethylacrylate, cetyl α-allyloxymethylacrylate, heptadecyl α-allyloxymethylacrylate, stearyl α-allyloxymethylacrylate, nonadecyl α-allyloxymethylacrylate, eicosyl α-allyloxymethylacrylate, ceryl α-allyloxymethylacrylate, and melissyl α-allyloxymethylacrylate. Among these, methyl α-allyloxymethylacrylate (also referred to as "α-(allyloxymethyl)methyl acrylate") is particularly suitable. The above-mentioned α-(unsaturated alkoxyalkyl)acrylate can be produced, for example, by the production method disclosed in WO 2010 / 114077. The content of the N-substituted maleimide monomer, dialkyl-2,2'-(oxydimethylene)diacrylate monomer, and / or α-(unsaturated alkoxyalkyl)acrylate (the total content when two or more types are used) is, for example, preferably 1% by mass or more and 40% by mass or less, based on 100% by mass of the base polymer component. Within this range, a cured film with improved heat resistance, dispersibility, surface hardness, and the like can be obtained. Increasing the content of the main chain ring structure derived from these monomer components tends to improve adhesion. Furthermore, increasing the amount of N-substituted maleimide monomer added results in a cured film with superior hardness, and the use of dialkyl-2,2'-(oxydimethylene)diacrylate monomer results in a cured film with superior heat discoloration resistance. If the content of the N-substituted maleimide monomer is too high, the development speed may not be optimal. The content of the structural units derived from the N-substituted maleimide monomer, the structural units derived from the dialkyl-2,2'-(oxydimethylene)diacrylate monomer, and / or the structural units derived from the α-(unsaturated alkoxyalkyl)acrylate relative to 100% by mass of all monomer units is more preferably 2 to 40% by mass, and even more preferably 3 to 35% by mass.

[0052] The other (meth)acrylic acid ester monomers mentioned above mean (meth)acrylic acid ester monomers other than dialkyl-2,2'-(oxydimethylene)diacrylate monomers and α-(unsaturated alkoxyalkyl)acrylates, and include, for example, methyl (meth)acrylate, ethyl (meth)acrylate, n-propyl (meth)acrylate, i-propyl (meth)acrylate, n-butyl (meth)acrylate, s-butyl (meth)acrylate, t-butyl (meth)acrylate, n-amyl (meth)acrylate, s-amyl (meth)acrylate, (meth)acrylic acid ester monomers, methyl (meth)acrylate, ethyl (meth)acrylate, n-propyl (meth)acrylate, i-propyl (meth)acrylate, n-butyl (meth)acrylate, s-butyl (meth)acrylate, t-butyl (meth)acrylate, n-amyl (meth)acrylate, s-amyl (meth)acrylate, methyl (meth)acrylate, ethyl (meth)acrylate, n-butyl (meth)acrylate, ethyl ... p) t-Amyl acrylate, n-hexyl (meth)acrylate, 2-ethylhexyl (meth)acrylate, isodecyl (meth)acrylate, tridecyl (meth)acrylate, cyclohexyl (meth)acrylate, cyclohexylmethyl (meth)acrylate, octyl (meth)acrylate, isooctyl (meth)acrylate, lauryl (meth)acrylate, stearyl (meth)acrylate, benzyl (meth)acrylate, phenyl (meth)acrylate, isobornyl (meth)acrylate, adamantyl (meth)acrylate, tricyclo (meth)acrylate Decanyl, 2-hydroxyethyl (meth)acrylate, 2-hydroxypropyl (meth)acrylate, 3-hydroxypropyl (meth)acrylate, 2-hydroxybutyl (meth)acrylate, 3-hydroxybutyl (meth)acrylate, 4-hydroxybutyl (meth)acrylate, 2-methoxyethyl (meth)acrylate, 2-ethoxyethyl (meth)acrylate, phenoxyethyl (meth)acrylate, tetrahydrofurfuryl (meth)acrylate, glycidyl (meth)acrylate, β-methylglycidyl (meth)acrylate, (meth)acrylic acid β-Ethylglycidyl, (3,4-epoxycyclohexyl)methyl (meth)acrylate, N,N-dimethylaminoethyl (meth)acrylate, methyl α-hydroxymethylacrylate, ethyl α-hydroxymethylacrylate, etc., as well as 1,4-dioxaspiro[4,5]dec-2-ylmethacrylic acid, (meth)acryloylmorpholine, tetrahydrofurfuryl acrylate, 4-(meth)acryloyloxymethyl-2-methyl-2-ethyl-1,3-dioxolane, 4-(meth)acryloyloxymethyl-2-methyl-2-isobutyl-1,Examples of such compounds include 3-dioxolane, 4-(meth)acryloyloxymethyl-2-methyl-2-cyclohexyl-1,3-dioxolane, 4-(meth)acryloyloxymethyl-2,2-dimethyl-1,3-dioxolane, and alkoxylated phenylphenol (meth)acrylate. Commercially available products of these compounds include MMDOL30, MEDOL30, MIBDOL30, CHDOL30, MEDOL10, MIBDOL10, MIBDOL10, CHDOL10, Viscoat 150, and Viscoat 160 (all manufactured by Osaka Organic Chemical Industry Ltd.), ACMO (manufactured by Kohjinsha), and A-LEN-10 (manufactured by Shin-Nakamura Chemical Co., Ltd.). Among these, methyl (meth)acrylate, ethyl (meth)acrylate, butyl (meth)acrylate, cyclohexyl (meth)acrylate, benzyl (meth)acrylate, and alkoxylated phenylphenol (meth)acrylate are preferred due to their excellent heat resistance. It is more preferable to use methyl (meth)acrylate, benzyl (meth)acrylate, cyclohexyl (meth)acrylate, and / or alkoxylated phenylphenol (meth)acrylate, because they have excellent heat resistance, adhesion, and developability. Furthermore, from the viewpoint of compatibility, alicyclic hydrocarbon group-containing monomers (units), particularly alicyclic (meth)acrylate-derived structural units are preferred. Examples of the aromatic vinyl monomer include styrene, vinyltoluene, α-methylstyrene, methoxystyrene, etc. Among them, styrene and vinyltoluene are preferred in terms of solubility, heat discoloration resistance and heat decomposition resistance of the polymer. The content of the other (meth)acrylic acid ester monomer and / or aromatic vinyl monomer (the total content when two or more types are used) is preferably, for example, 1 to 80% by mass relative to 100% by mass of the base polymer component. Within this range, a cured film with superior heat discoloration resistance, compatibility, alkali solubility, etc. can be obtained. The content is more preferably 5 to 75% by mass, and even more preferably 10 to 70% by mass. The other monomer may also be, for example, one or more of the following compounds, and the content thereof is preferably 20% by mass or less, and preferably 10% by mass or less, based on 100% by mass of the base polymer component: (meth)acrylamides such as N,N-dimethyl(meth)acrylamide and N-methylol(meth)acrylamide; macromonomers having a (meth)acryloyl group at one end of the polymer molecular chain, such as polystyrene, polymethyl(meth)acrylate, polyethylene oxide, polypropylene oxide, polysiloxane, polycaprolactone, and polycaprolactam; conjugated dienes such as 1,3-butadiene, isoprene, and chloroprene; vinyl esters such as vinyl acetate, vinyl propionate, vinyl butyrate, and vinyl benzoate; methyl vinyl ether, ethyl vinyl ether, propyl vinyl ether, butyl vinyl ether, 2-ethyl vinyl ether, ... Vinyl ethers such as hexyl vinyl ether, n-nonyl vinyl ether, lauryl vinyl ether, cyclohexyl vinyl ether, methoxyethyl vinyl ether, ethoxyethyl vinyl ether, methoxyethoxyethyl vinyl ether, methoxypolyethylene glycol vinyl ether, 2-hydroxyethyl vinyl ether, and 4-hydroxybutyl vinyl ether; N-vinyl compounds such as N-vinylpyrrolidone, N-vinylcaprolactam, N-vinylimidazole, N-vinylmorpholine, and N-vinylacetamide; unsaturated isocyanates such as isocyanatoethyl (meth)acrylate and allyl isocyanate. As a method for polymerizing the above-mentioned monomer components, commonly used techniques such as bulk polymerization, solution polymerization, emulsion polymerization, etc. can be used, and may be appropriately selected depending on the purpose and application. Among them, solution polymerization is preferred because it is industrially advantageous and allows easy structural adjustment such as molecular weight. Furthermore, as a polymerization mechanism for the above-mentioned monomer components, polymerization methods based on mechanisms such as radical polymerization, anionic polymerization, cationic polymerization, and coordination polymerization can be used, but polymerization methods based on a radical polymerization mechanism are preferred because they are industrially advantageous. The polymerization initiation method for the above polymerization reaction can be achieved by supplying the energy required to initiate polymerization to the monomer components from an active energy source such as heat, electromagnetic waves (infrared rays, ultraviolet rays, X-rays, etc.), or electron beams, and the use of a polymerization initiator in combination is preferable because it can significantly reduce the energy required to initiate polymerization and also facilitates reaction control. The molecular weight of the polymer obtained by polymerizing the above monomer components can be controlled by adjusting the amount and type of polymerization initiator, the polymerization temperature, the type and amount of chain transfer agent, etc. When the monomer components are polymerized by solution polymerization, the solvent used for polymerization is not particularly limited as long as it is inert to the polymerization reaction, and may be appropriately selected depending on polymerization conditions such as the polymerization mechanism, the type and amount of the monomers used, the polymerization temperature, and the polymerization concentration. However, when a solvent is used as a diluent or the like when a colored photosensitive resin composition is subsequently produced, it is efficient and preferable to use a solvent containing the solvent for solution polymerization of the monomer components. Suitable examples of the solvent include the following compounds, and one or more of these can be used. Monoalcohols such as methanol, ethanol, isopropanol, n-butanol, and s-butanol; glycols such as ethylene glycol and propylene glycol; cyclic ethers such as tetrahydrofuran and dioxane; glycol monoethers such as ethylene glycol monomethyl ether, ethylene glycol monoethyl 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 monobutyl ether, and 3-methoxybutanol; glycol ethers such as ethylene glycol dimethyl ether, ethylene glycol diethyl ether, ethylene glycol ethyl methyl ether, diethylene glycol dimethyl ether, diethylene glycol diethyl ether, diethylene glycol ethyl methyl ether, propylene glycol dimethyl ether, and propylene glycol diethyl ether; ethylene glycol monomethyl ether acetate glycol monoether esters such as ethylene glycol monoethyl ether acetate, ethylene glycol monobutyl ether acetate, diethylene glycol monomethyl ether acetate, diethylene glycol monoethyl ether acetate, diethylene glycol monobutyl ether acetate, propylene glycol monomethyl ether acetate, propylene glycol monoethyl ether acetate, propylene glycol monobutyl ether acetate, dipropylene glycol monomethyl ether acetate, dipropylene glycol monoethyl ether acetate, dipropylene glycol monobutyl ether acetate, and 3-methoxybutyl acetate; alkyl esters such as methyl acetate, ethyl acetate, propyl acetate, isopropyl acetate, butyl acetate, methyl propionate, ethyl propionate, butyl propionate, methyl lactate, ethyl lactate, butyl lactate, methyl 3-methoxypropionate, ethyl 3-methoxypropionate, methyl 3-ethoxypropionate, ethyl 3-ethoxypropionate, methyl acetoacetate, and ethyl acetoacetate;Ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone, cyclohexanone, etc.; aromatic hydrocarbons such as benzene, toluene, xylene, ethylbenzene, etc.; aliphatic hydrocarbons such as hexane, cyclohexane, octane, etc.; amides such as dimethylformamide, dimethylacetamide, N-methylpyrrolidone, etc.; Among these solvents, it is more preferable to use propylene glycol monomethyl ether, propylene glycol monomethyl ether acetate, diethylene glycol dimethyl ether, diethylene glycol ethyl methyl ether, and ethyl lactate in view of the solubility of the resulting polymer, the surface smoothness when a coating film is formed, the small impact on the human body and the environment, and the ease of industrial availability. The amount of the solvent used is preferably 50 to 1000 parts by mass, and more preferably 100 to 500 parts by mass, per 100 parts by mass of the base polymer component. When the monomer components are polymerized by a radical polymerization mechanism, it is industrially advantageous and preferable to use a polymerization initiator that generates radicals by heat. Such a polymerization initiator is not particularly limited as long as it generates radicals by supplying thermal energy, and may be appropriately selected depending on the polymerization conditions, such as the polymerization temperature, solvent, and type of monomer to be polymerized. In addition, a reducing agent such as a transition metal salt or an amine may be used in combination with the polymerization initiator. Examples of the polymerization initiator include peroxides and azo compounds that are typically used as polymerization initiators, such as cumene hydroperoxide, diisopropylbenzene hydroperoxide, di-t-butyl peroxide, lauroyl peroxide, benzoyl peroxide, t-butylperoxyisopropyl carbonate, t-butylperoxy-2-ethylhexanoate, azobisisobutyronitrile, 1,1′-azobis(cyclohexanecarbonitrile), 2,2′-azobis(2,4-dimethylvaleronitrile), dimethyl 2,2′-azobis(2-methylpropionate), hydrogen peroxide, and persulfates, and these may be used alone or in combination of two or more thereof. The amount of the polymerization initiator used is not particularly limited and may be appropriately determined depending on the type and amount of monomer used, polymerization conditions such as polymerization temperature and polymerization concentration, and the molecular weight of the target polymer. For example, to obtain a polymer with a weight-average molecular weight of several thousand to several tens of thousands, the amount is preferably 0.1 to 20 parts by mass, and more preferably 0.5 to 15 parts by mass, per 100 parts by mass of the base polymer component. In order to reduce the concentration of oligomers (e.g., molecular weights of 500 or less) and obtain a polymer with a narrow molecular weight distribution, the amount is preferably 0.1 to 10 parts by mass, and more preferably 0.5 to 3 parts by mass, per 100 parts by mass of all monomer components (total amount of all monomers: 100 parts by mass). In the polymerization, a commonly used chain transfer agent may be used as needed. Preferably, a polymerization initiator and a chain transfer agent are used in combination. The use of a chain transfer agent during polymerization tends to suppress an increase in molecular weight distribution and gelation. Examples of the chain transfer agent include mercaptocarboxylic acids such as mercaptoacetic acid and 3-mercaptopropionic acid; mercaptocarboxylic acid esters such as methyl mercaptoacetate, methyl 3-mercaptopropionate, 2-ethylhexyl 3-mercaptopropionate, n-octyl 3-mercaptopropionate, methoxybutyl 3-mercaptopropionate, stearyl 3-mercaptopropionate, trimethylolpropane tris(3-mercaptopropionate), pentaerythritol tetrakis(3-mercaptopropionate), and dipentaerythritol hexakis(3-mercaptopropionate); ethyl mercaptan, t-butyl mercaptan, and n-dodecyl Examples of suitable mercaptans include alkyl mercaptans such as mercaptan and 1,2-dimercaptoethane; mercaptoalcohols such as 2-mercaptoethanol and 4-mercapto-1-butanol; aromatic mercaptans such as benzenethiol, m-toluenethiol, p-toluenethiol, and 2-naphthalenethiol; mercaptoisocyanurates such as tris[(3-mercaptopropionyloxy)-ethyl]isocyanurate; disulfides such as 2-hydroxyethyl disulfide and tetraethyl thiuram disulfide; dithiocarbamates such as benzyl diethyl dithiocarbamate; monomer dimers such as α-methylstyrene dimer; and alkyl halides such as carbon tetrabromide. These may be used alone or in combination of two or more. Among these, compounds having a mercapto group such as mercaptocarboxylic acids, mercaptocarboxylic acid esters, alkyl mercaptans, mercaptoalcohols, aromatic mercaptans, and mercaptoisocyanurates are preferably used in terms of availability, crosslinking prevention ability, small degree of decrease in polymerization rate, etc. Alkyl mercaptans, mercaptocarboxylic acids, and mercaptocarboxylic acid esters are more preferred, and n-dodecyl mercaptan and mercaptopropionic acid are even more preferred. The amount of the chain transfer agent used is not particularly limited and may be appropriately determined depending on the type and amount of the monomer used, polymerization conditions such as polymerization temperature and polymerization concentration, the molecular weight of the target polymer, etc., but to obtain a polymer having a weight-average molecular weight of several thousand to several tens of thousands, the amount is preferably 0.1 to 20 parts by mass, more preferably 0.5 to 15 parts by mass, per 100 parts by mass of the base polymer component. Regarding the polymerization conditions, the polymerization temperature may be appropriately set depending on the type and amount of the monomer used, the type and amount of the polymerization initiator, etc., and is, for example, preferably 50 to 150° C., more preferably 70 to 120° C. Similarly, the polymerization time may also be appropriately set, and is, for example, preferably 1 to 5 hours, more preferably 2 to 4 hours. The alkali-soluble polymer also preferably has a double bond in the side chain, specifically, a polymer (also referred to as a polymer having a polymerizable double bond in the side chain) obtained by reacting a polymer (base polymer) obtained by polymerizing the monomer components with a compound having a functional group capable of bonding to an acid group and a polymerizable double bond. In the compound having a functional group capable of bonding to an acid group and a polymerizable double bond, examples of the polymerizable double bond include a (meth)acryloyl group, a vinyl group, an allyl group, and a methallyl group, and the compound preferably has one or more of these. Among these, a (meth)acryloyl group is preferred in terms of reactivity. Furthermore, examples of the functional group capable of bonding to an acid group include a hydroxy group, an epoxy group, an oxetanyl group, an isocyanate group, and an oxazoline group, and the compound preferably has one or more of these. Among these, an epoxy group (including a glycidyl group) is preferred in terms of the speed of the modification treatment reaction, heat resistance, and compatibility. When a double bond is introduced into a side chain, it is particularly preferred to add a compound containing at least one selected from an epoxy group, an oxazoline group, an isocyanate group, and a hydroxy group and a polymerizable unsaturated double bond, preferably in an amount of 5 to 120% by mass, more preferably 5 to 80% by mass, and particularly preferably 5 to 60% by mass, based on the polymer (base polymer). By adjusting the amount within the above range, the exposure sensitivity, developability, and storage stability become good. The compound having a functional group capable of bonding to an acid group and a polymerizable double bond is preferably glycidyl (meth)acrylate, β-methylglycidyl (meth)acrylate, β-ethylglycidyl (meth)acrylate, vinylbenzyl glycidyl ether, allyl glycidyl ether, (3,4-epoxycyclohexyl)methyl (meth)acrylate, vinylcyclohexene oxide, etc., and one or more of these can be used. Among these, it is preferable to use a compound (monomer) having an epoxy group and a (meth)acryloyl group. Examples of methods for obtaining the side-chain double bond-containing polymer include a method in which, when the base polymer component is reacted with a compound having a functional group capable of bonding to an acid group and a polymerizable double bond, the amount of acid groups (preferably carboxyl groups) in the base polymer component is in excess of the amount of the compound having a functional group capable of bonding to an acid group and a polymerizable double bond; and a method in which, after reacting the base polymer component with a compound having a functional group capable of bonding to an acid group and a polymerizable double bond, the compound is further reacted with a compound having a polybasic acid anhydride group. The step of reacting the base polymer component (preferably a polymer having a carboxyl group) with the compound having a functional group capable of bonding to an acid group and a polymerizable double bond is preferably carried out at a temperature in the range of 50 to 160°C to ensure a good reaction rate and prevent gelation. The temperature is more preferably 70 to 140°C, and even more preferably 90 to 130°C. To improve the reaction rate, a basic catalyst or acidic catalyst commonly used for esterification or transesterification can be used as a catalyst. Among these, the use of a basic catalyst is preferred because it reduces side reactions. Examples of the basic catalyst include tertiary amines such as dimethylbenzylamine, triethylamine, tri-n-octylamine, and tetramethylethylenediamine; quaternary ammonium salts such as tetramethylammonium chloride, tetramethylammonium bromide, tetrabutylammonium bromide, and n-dodecyltrimethylammonium chloride; urea compounds such as tetramethylurea; alkylguanidines such as tetramethylguanidine; amide compounds such as dimethylformamide and dimethylacetamide; tertiary phosphines such as triphenylphosphine and tributylphosphine; and quaternary phosphonium salts such as tetraphenylphosphonium bromide and benzyltriphenylphosphonium bromide. One or more of these may be used. Among these, dimethylbenzylamine, triethylamine, tetramethylurea, and triphenylphosphine are preferred in terms of reactivity, ease of handling, and halogen-free properties. The amount of the catalyst used is preferably 0.01 to 5.0 parts by mass, more preferably 0.1 to 3.0 parts by mass, per 100 parts by mass of the total amount of the base polymer component and the compound having a functional group capable of bonding to an acid group and a polymerizable double bond group. The step of reacting the base polymer component with the compound having a polymerizable double bond and a functional group capable of bonding to an acid group is preferably carried out in the presence of a molecular oxygen-containing gas, typically air or oxygen gas diluted with an inert gas such as nitrogen, in order to prevent gelation. The polymerization inhibitor may be a polymerization inhibitor commonly used for radically polymerizable monomers, such as hydroquinone, methylhydroquinone, trimethylhydroquinone, t-butylhydroquinone, methoquinone, 6-t-butyl-2,4-xylenol, 2,6-di-t-butylphenol, 2,6-di-t-butyl-4-methoxyphenol, or 2,2'-methylenebis(4-methyl-6-t-butylphenol), or a copper salt of an organic acid or a phenothiazine. One or more of these may be used. Among these, phenolic inhibitors are preferred in terms of low coloration and polymerization-inhibiting ability, and 2,2'-methylenebis(4-methyl-6-t-butylphenol), methoquinone, 6-t-butyl-2,4-xylenol, or 2,6-di-t-butylphenol are more preferred in terms of availability and economy. The amount of the polymerization inhibitor used is preferably 0.001 to 1.0 part by mass, more preferably 0.01 to 0.5 part by mass, relative to 100 parts by mass of the total amount of the base polymer component and the compound having a functional group capable of bonding to an acid group and a polymerizable double bond, from the viewpoints of ensuring a sufficient polymerization-inhibiting effect and curing properties when the curable resin composition is prepared. Examples of the compound having a polybasic acid anhydride group include succinic anhydride, dodecenylsuccinic acid, pentadecenylsuccinic acid, octadecenylsuccinic acid, tetrahydrophthalic anhydride, methyltetrahydrophthalic anhydride, hexahydrophthalic anhydride, methylhexahydrophthalic anhydride, endomethylenetetrahydrophthalic anhydride, methylendomethylenetetrahydrophthalic anhydride, maleic anhydride, itaconic anhydride, phthalic anhydride, glutaric anhydride, phthalic anhydride, trimellitic anhydride, and pyromellitic anhydride, and one or more of these can be used. The alkali-soluble polymer having a polymerizable double bond in its side chain (side-chain double-bond-containing polymer) preferably contained in the composition of the present invention has a double bond equivalent of 200 to 10,000 (g / mol). By setting the double bond equivalent within this range, it is expected that both sufficient storage stability of the polymer and solvent resistance of the colored photosensitive resin composition of the present invention can be achieved at an even higher level. The double bond equivalent is more preferably 250 or more, even more preferably 300 or more, particularly preferably 350 or more, and even more preferably 400 or more. It is also more preferably 5,000 or less, even more preferably 4,000 or less, particularly preferably 3,000 or less, even more preferably 2,000 or less, even more preferably 1,000 or less, and most preferably 800 or less. The double bond equivalent is the mass (g) of the solid content of the polymer solution per 1 mol of double bonds in the polymer. The mass of the solid content of the polymer solution is the sum of the mass of the monomer components constituting the polymer and the mass of the chain transfer agent (the mass of the base polymer component, the mass of the compound having a functional group capable of bonding to an acid group and a polymerizable double bond group, and the mass of the chain transfer agent). The double bond equivalent can be calculated by dividing the mass (g) of the polymer solid content of the polymer solution by the amount of double bonds (mol) in the polymer. The amount of double bonds in the polymer can be determined by confirming the structures of the acid group-containing monomer and the compound having a polymerizable double bond (the compound having a functional group capable of bonding to an acid group and a polymerizable double bond) used in the polymerization and determining their amounts. It can also be measured using various analyses such as titration, elemental analysis, NMR, and IR, or differential scanning calorimetry. For example, it can be calculated by measuring the number of ethylenic double bonds contained per gram of polymer in accordance with the iodine value test method described in JIS K 0070:1992. Furthermore, the glass transition temperature (Tg) of the side chain double bond-containing polymer is preferably 80°C or lower. This improves adhesion. It is more preferably 70°C or lower, even more preferably 60°C or lower, particularly preferably 50°C or lower, and most preferably 40°C or lower. There are no particular restrictions on the lower limit, but from the viewpoint of heat resistance, it is preferably -10°C or higher, and more preferably 0°C or higher. The glass transition temperature (Tg) can be measured, for example, by the following method. The copolymer solution is applied to a 5cm square glass substrate, spin-coated onto the glass substrate, and dried at room temperature under reduced pressure for 4 hours to form a thin film with a mass of 30mg or less, thereby removing volatile components and obtaining a solid content. The obtained solid content is measured using a DSC (differential scanning calorimeter, measuring device: Netsch DSC3500) in a nitrogen stream at a heating rate of 10°C / min in accordance with JIS-K7121. In the colored photosensitive resin composition, the content of the alkali-soluble resin (preferably an alkali-soluble polymer) is preferably 5% by mass or more and suitably 70% by mass or less, relative to 100% by mass of the total solid content of the colored photosensitive resin composition. By being in this range, the effects of the present invention can be more significantly exhibited. The content is more preferably 10 to 65% by mass, even more preferably 10 to 50% by mass, particularly preferably 10 to 40% by mass, even more preferably 15 to 40% by mass, and most preferably 18 to 40% by mass. [Polymerizable monomer] The polymerizable monomer is a low molecular weight compound having a polymerizable unsaturated bond (also referred to as a polymerizable unsaturated group) that can be polymerized by irradiation with active energy rays such as free radicals, electromagnetic waves (e.g., infrared rays, ultraviolet rays, X-rays, etc.), and electron beams. Examples include monofunctional compounds having one polymerizable unsaturated group in the molecule and polyfunctional compounds having two or more polymerizable unsaturated groups. The molecular weight is not particularly limited, but from the viewpoint of ease of handling, it is preferably 3000 or less, and more preferably 2000 or less. Examples of the monofunctional polymerizable monomer include, among the compounds exemplified as other monomers preferably contained in the monomer component of the alkali-soluble polymer, N-substituted maleimides and (meth)acrylic acid esters; (meth)acrylamides; unsaturated monocarboxylic acids; unsaturated polycarboxylic acids; unsaturated monocarboxylic acids in which the unsaturated group and the carboxyl group are chain-extended; unsaturated acid anhydrides; aromatic vinyls; conjugated dienes; vinyl esters; vinyl ethers; N-vinyl compounds; and unsaturated isocyanates. Examples of the polyfunctional polymerizable monomer include the following compounds. Bifunctional (meth)acrylates such as ethylene glycol di(meth)acrylate, diethylene glycol di(meth)acrylate, polyethylene glycol di(meth)acrylate, propylene glycol di(meth)acrylate, butylene glycol di(meth)acrylate, hexanediol di(meth)acrylate, cyclohexanedimethanol di(meth)acrylate, bisphenol A alkylene oxide di(meth)acrylate, and bisphenol F alkylene oxide di(meth)acrylate Acrylate compounds; trimethylolpropane tri(meth)acrylate, ditrimethylolpropane tetra(meth)acrylate, glycerin tri(meth)acrylate, pentaerythritol tri(meth)acrylate, pentaerythritol tetra(meth)acrylate, dipentaerythritol penta(meth)acrylate, dipentaerythritol hexa(meth)acrylate, tripentaerythritol hepta(meth)acrylate, tripentaerythritol octa(meth)acrylate, ethylenediamine Ethylene oxide-added trimethylolpropane tri(meth)acrylate, Ethylene oxide-added ditrimethylolpropane tetra(meth)acrylate, Ethylene oxide-added pentaerythritol tetra(meth)acrylate, Ethylene oxide-added dipentaerythritol hexa(meth)acrylate, Propylene oxide-added trimethylolpropane tri(meth)acrylate, Propylene oxide-added ditrimethylolpropane tetra(meth)acrylate, Propylene oxide-added pentaerythritol hexa(meth)acrylate tri- or higher functional polyfunctional (meth)acrylate compounds such as erythritol tetra(meth)acrylate, propylene oxide-added dipentaerythritol hexa(meth)acrylate, ε-caprolactone-added trimethylolpropane tri(meth)acrylate, ε-caprolactone-added ditrimethylolpropane tetra(meth)acrylate, ε-caprolactone-added pentaerythritol tetra(meth)acrylate, and ε-caprolactone-added dipentaerythritol hexa(meth)acrylate; Ethylene glycol divinyl ether, diethylene glycol divinyl ether, polyethylene glycol divinyl ether, propylene glycol divinyl ether, butylene glycol divinyl ether, hexanediol divinyl ether, bisphenol A alkylene oxide divinyl ether, bisphenol F alkylene oxide divinyl ether, trimethylolpropane trivinyl ether, ditrimethylolpropane tetravinyl ether, glycerin trivinyl ether, pentaerythritol tetravinyl ether, dipentaerythritol pentavinyl ether, dipentaerythritol hexavinyl ether, ethylene oxide-added trimethylolpropane trivinyl ether, ethylene oxide-added ditrimethylolpropane tetravinyl ether, ethylene oxide-added pentaerythritol tetravinyl ether polyfunctional vinyl ethers such as dipentaerythritol vinyl ether and ethylene oxide-added dipentaerythritol hexavinyl ether; vinyl ether group-containing (meth)acrylic acid esters such as 2-vinyloxyethyl (meth)acrylate, 3-vinyloxypropyl (meth)acrylate, 1-methyl-2-vinyloxyethyl (meth)acrylate, 2-vinyloxypropyl (meth)acrylate, 4-vinyloxybutyl (meth)acrylate, 4-vinyloxycyclohexyl (meth)acrylate, 5-vinyloxypentyl (meth)acrylate, 6-vinyloxyhexyl (meth)acrylate, 4-vinyloxymethylcyclohexylmethyl (meth)acrylate, p-vinyloxymethylphenylmethyl (meth)acrylate, 2-(vinyloxyethoxy)ethyl (meth)acrylate, and 2-(vinyloxyethoxyethoxyethoxy)ethyl (meth)acrylate; Ethylene glycol diallyl ether, diethylene glycol diallyl ether, polyethylene glycol diallyl ether, propylene glycol diallyl ether, butylene glycol diallyl ether, hexanediol diallyl ether, bisphenol A alkylene oxide diallyl ether, bisphenol F alkylene oxide diallyl ether, trimethylolpropane triallyl ether, ditrimethylolpropane tetraallyl ether, glycerin triallyl ether, pentaerythritol tetraallyl ether, dipentaerythritol pentaallyl ether, dipentaerythritol hexaallyl ether, ethylene oxide-added trimethylolpropane triallyl ether, ethylene oxide-added ditrimethylolpropane tetraallyl ether, ethylene oxide-added pentaerythritol tetraallyl ether, ethylene oxide-added dipentaerythritol hexaallyl ether polyfunctional allyl ethers such as allyl ether; allyl group-containing (meth)acrylic acid esters such as allyl (meth)acrylate; polyfunctional (meth)acryloyl group-containing isocyanurates such as tri(acryloyloxyethyl)isocyanurate, tri(methacryloyloxyethyl)isocyanurate, alkylene oxide-added tri(acryloyloxyethyl)isocyanurate, and alkylene oxide-added tri(methacryloyloxyethyl)isocyanurate; polyfunctional allyl group-containing isocyanurates such as triallyl isocyanurate; polyfunctional urethane (meth)acrylates obtained by reacting polyfunctional isocyanates such as tolylene diisocyanate, isophorone diisocyanate, and xylylene diisocyanate with hydroxyl group-containing (meth)acrylic acid esters such as 2-hydroxyethyl (meth)acrylate and 2-hydroxypropyl (meth)acrylate; polyfunctional aromatic vinyls such as divinylbenzene; and the like. A particularly preferred polymerizable monomer, a polyfunctional (meth)acrylate compound having two or more functional groups, will be described in detail below. A difunctional or higher polyfunctional (meth)acrylate compound (hereinafter simply referred to as a "polyfunctional (meth)acrylate compound") is a compound having two or more (meth)acryloyl groups in one molecule. By including such a compound, the colored photosensitive resin composition has excellent photosensitivity and curability, and it is possible to obtain a cured film with extremely high hardness and transparency. The functionality of the polyfunctional (meth)acrylate compound is preferably 3 or more, more preferably 4 or more, and even more preferably 5 or more. Furthermore, from the viewpoint of further suppressing cure shrinkage, the functionality is preferably 10 or less, more preferably 8 or less, and even more preferably 6 or less. The (meth)acryloyl group refers to a methacryloyl group and / or an acryloyl group, with an acryloyl group being preferred from the viewpoint of superior reactivity. That is, it is particularly preferable that the polyfunctional (meth)acrylate compound is a polyfunctional acrylate compound having two or more acryloyl groups. The content of the polymerizable monomer may be appropriately set depending on the type of polymerizable monomer and alkali-soluble polymer used, as well as the purpose and application, but from the viewpoint of superior developability and solvent resistance, it is preferably 2% by mass or more and suitably 85% by mass or less, relative to 100% by mass of the total solids content of the colored photosensitive resin composition. The lower limit is more preferably 5% by mass or more, even more preferably 10% by mass or more, and particularly preferably 15% by mass or more, and the upper limit is more preferably 75% by mass or less, even more preferably 60% by mass or less, particularly preferably 50% by mass or less, and most preferably 45% by mass or less. The content of the polymerizable monomer is preferably 50 to 500 parts by mass relative to 100 parts by mass of the alkali-soluble polymer. A polymerizable monomer content within this range not only provides a cured film with higher surface hardness, but also, combined with the alkali-soluble polymer having a preferred weight-average molecular weight of 5,000 or more, improves developability and solvent resistance. The content is more preferably 80 parts by mass or more, even more preferably 90 parts by mass or more, and particularly preferably 100 parts by mass or more. From the viewpoint of further improving developability, the content is more preferably 400 parts by mass or less. The content is even more preferably 300 parts by mass or less, particularly preferably 200 parts by mass or less, and most preferably 150 parts by mass or less. [Photopolymerization initiator] The colored photosensitive resin composition preferably further contains a photopolymerization initiator. The photopolymerization initiator is preferably a radically polymerizable photopolymerization initiator. The radically polymerizable photopolymerization initiator generates polymerization-initiating radicals upon irradiation with active energy rays such as electromagnetic waves or electron beams, and one or more commonly used initiators can be used. Furthermore, one or more photosensitizers, photoradical polymerization accelerators, etc. may be used in combination, as needed. Sensitivity and curability are further improved by using a photosensitizer and / or a photoradical polymerization accelerator together with the photopolymerization initiator. Specific examples of the photopolymerization initiator include the following compounds. alkylphenone compounds such as 2,2-diethoxyacetophenone, 2,2-dimethoxy-2-phenylacetophenone, 1-hydroxycyclohexyl phenyl ketone, 2-hydroxy-2-methyl-1-phenylpropan-1-one, 1-[4-(2-hydroxyethoxy)phenyl]-2-hydroxy-2-methyl-1-propan-1-one, 2-hydroxy-1-{4-[4-(2-hydroxy-2-methylpropionyl)benzyl]phenyl}-2-methylpropan-1-one, 2-methyl-1-(4-methylthiophenyl)-2-morpholinopropan-1-one, 2-benzyl-2-dimethylamino-1-(4-morpholinophenyl)-butanone-1, 2-(dimethylamino)-2-[(4-methylphenyl)methyl]-1-[4-(4-morpholinyl)phenyl]-1-butanone; Benzophenone compounds such as benzophenone, 4,4'-bis(dimethylamino)benzophenone, and 2-carboxybenzophenone; benzoin compounds such as benzoin methyl ether, benzoin ethyl ether, benzoin isopropyl ether, and benzoin isobutyl ether; Thioxanthone compounds such as thioxanthone, 2-ethylthioxanthone, 2-isopropylthioxanthone, 2-chlorothioxanthone, 2,4-dimethylthioxanthone, and 2,4-diethylthioxanthone; halomethylated triazine compounds such as 2-(4-methoxyphenyl)-4,6-bis(trichloromethyl)-s-triazine, 2-(4-methoxynaphthyl)-4,6-bis(trichloromethyl)-s-triazine, 2-(4-ethoxynaphthyl)-4,6-bis(trichloromethyl)-s-triazine, and 2-(4-ethoxycarboxynylnaphthyl)-4,6-bis(trichloromethyl)-s-triazine; halomethylated oxadiazole compounds such as 2-trichloromethyl-5-(2'-benzofuryl)-1,3,4-oxadiazole, 2-trichloromethyl-5-[β-(2'-benzofuryl)vinyl]-1,3,4-oxadiazole, 4-oxadiazole, and 2-trichloromethyl-5-furyl-1,3,4-oxadiazole; biimidazole compounds such as 2,2'-bis(2-chlorophenyl)-4,4',5,5'-tetraphenyl-1,2'-biimidazole, 2,2'-bis(2,4-dichlorophenyl)-4,4',5,5'-tetraphenyl-1,2'-biimidazole, and 2,2'-bis(2,4,6-trichlorophenyl)-4,4',5,5'-tetraphenyl-1,2'-biimidazole; Oxime ester compounds such as 1,2-octanedione, 1-[4-(phenylthio)-, 2-(O-benzoyloxime)], ethanone, 1-[9-ethyl-6-(2-methylbenzoyl)-9H-carbazol-3-yl]-, 1-(O-acetyloxime); Titanocene compounds such as bis(η5-2,4-cyclopentadien-1-yl)-bis(2,6-difluoro-3-(1H-pyrrol-1-yl)-phenyl)titanium; Benzoic acid ester compounds such as p-dimethylaminobenzoic acid and p-diethylaminobenzoic acid; Acridine compounds such as 9-phenylacridine; benzyl ketal compounds such as 2,2-dimethoxy-1,2-diphenylethan-1-one ("Omnirad651", manufactured by BASF) and phenylglyoxylic acid methyl ester ("DAROCUR MBF", manufactured by BASF); hydroketone compounds such as 1-hydroxycyclohexylphenyl ketone ("Omnirad184", BASF), 2-hydroxy-2-methyl-1-phenylpropan-1-one ("DAROCUR1173", BASF), 1-[4-(2-hydroxyethoxy)phenyl]-2-hydroxy-2-methyl-1-propan-1-one ("Omnirad2959", BASF), 2-hydroxy-1-{4-[4-(2-hydroxy-2-methylpropionyl)benzyl]phenyl}-2-methylpropan-1-one ("Omnirad127", BASF), and [1-hydroxycyclohexylphenyl ketone + benzophenone] ("Omnirad500", BASF); phosphine oxide compounds such as 2,4,6-trimethylbenzoyl-diphenyl-phosphine oxide ("LUCIRIN TPO", manufactured by BASF) and bis(2,4,6-trimethylbenzoyl)-phenylphosphine oxide ("Omnirad819", manufactured by BASF); aminoketone compounds such as 2-methyl-1-[4-(methylthio)phenyl]-2-morpholinopropan-1-one ("Omnirad907", manufactured by BASF), 2-benzyl-2-dimethylamino-1-(4-morpholinophenyl)-butanone-1 ("Omnirad369", manufactured by BASF), and 2-dimethylamino-2-(4-methyl-benzyl)-1-(4-morpholin-4-yl-phenyl)-butan-1-one ("Omnirad379", manufactured by BASF); titanocene compounds such as bis(η5-2,4-cyclopentadien-1-yl)-bis(2,6-difluoro-3-(1H-pyrrol-1-yl)-phenyl)titanium ("Omnirad784", manufactured by BASF); Oxime ester compounds such as 1,2-octanedione, 1-[4-(phenylthio)-, 2-(O-benzoyloxime)] ("IRGACURE OXE01", manufactured by BASF); Among the above photopolymerization initiators, it is particularly preferable to use at least an aminoketone-based compound (also referred to as an aminoketone-based polymerization initiator). That is, it is preferable that the colored photosensitive resin composition further contains an aminoketone-based polymerization initiator. This results in better hardness, developability, and solvent resistance. It is also preferable to use a hydroketone-based compound (also referred to as a hydroketone-based polymerization initiator) or a benzyl ketal-based compound (also referred to as a benzyl ketal-based polymerization initiator). Examples of the photosensitizer or photoradical polymerization accelerator that may be used in combination with the photopolymerization initiator include dye compounds such as xanthene dyes, coumarin dyes, 3-ketocoumarin compounds, and pyrromethene dyes; dialkylaminobenzene compounds such as ethyl 4-dimethylaminobenzoate and 2-ethylhexyl 4-dimethylaminobenzoate; and mercaptan hydrogen donors such as 2-mercaptobenzothiazole, 2-mercaptobenzoxazole, and 2-mercaptobenzimidazole. The content of the photopolymerization initiator may be appropriately set depending on the purpose, application, etc., and is not particularly limited, but is preferably 0.5 parts by mass or more relative to 100 parts by mass of the total solid content of the colored photosensitive resin composition. This allows for the production of a cured film with superior solvent resistance. The content is more preferably 1 part by mass or more, and even more preferably 2 parts by mass or more. Furthermore, in consideration of the balance between the effects of decomposition products of the photopolymerization initiator and economic efficiency, the content is preferably 35 parts by mass or less. The content is more preferably 25 parts by mass or less, and even more preferably 20 parts by mass or less. In the present invention, it is also preferable to use an aminoketone polymerization initiator as the polymerization initiator as described above. In this case, the aminoketone polymerization initiator is preferably 20% by mass or more and 100% by mass or less relative to 100% by mass of the total amount of polymerization initiators (i.e., the total amount of the aminoketone polymerization initiator and other polymerization initiators). It is more preferably 30% by mass or more, even more preferably 50% by mass or more, and particularly preferably 55% by mass or more and 100% by mass or less. In the present invention, it is preferable to use 100% by mass, which means no other polymerization initiators are used. The content (total amount) of the photosensitizer and photoradical polymerization accelerator may be appropriately set depending on the purpose and application and is not particularly limited, but from the viewpoint of balancing curability, the effects of decomposition products, and economic efficiency, it is preferably 0.001 to 20 mass%, more preferably 0.01 to 15 mass%, and even more preferably 0.05 to 10 mass%, relative to 100 mass% of the total solid content of the curable resin composition of the present invention. [Dispersant] The colored photosensitive resin composition of the present invention preferably contains a dispersant. Since dyes are usually dissolved in resins, dispersants are not essential. However, dyes are generally present at high concentrations (10 to 30% by mass) in color filters, and aggregation and precipitation can lead to reduced contrast and brightness. To prevent this, it is effective to use a specific dispersant. Furthermore, when dyes and pigments are used in combination, the inclusion of a dispersant increases dispersion stability, prevents precipitation in the color filter, and suppresses reduced contrast and brightness. As the dispersant, anionic dispersants, nonionic dispersants, cationic dispersants, polymer (resin type) dispersants, etc. can be used. Among the above dispersants, dispersants having an amine value of 5 to 150 mgKOH / g are preferred. From the viewpoints of dispersibility and developability, the amine value is preferably 30 mgKOH / g or more, more preferably 50 mgKOH / g or more, even more preferably 70 mgKOH / g or more, and even more preferably 80 mgKOH / g or more, and is preferably 140 mgKOH / g or less, more preferably 130 mgKOH / g or less. The dispersant having an amine value refers to a dispersant having primary, secondary, or tertiary amino groups. The term "amine value" refers to the amine value calculated on an effective solids basis unless otherwise specified, and is a value expressed as the weight of KOH equivalent to the amount of base per gram of solids in the dispersant. The measurement method will be described later. The term "acid value" refers to the acid value calculated on an effective solids basis unless otherwise specified, and is calculated by neutralization titration. Specifically, a suitable dispersant is a polymer having a functional group containing a nitrogen atom, and its amine value, calculated as effective solid content, is preferably 5 to 100 mgKOH / g, more preferably 5 to 80 mgKOH / g. The amine value indicates the effective amount of groups adsorbed to pigments or dyes, and within the above range, the function of preventing aggregation of pigments or dyes can be exhibited, and sufficient dispersion stability can be achieved. Furthermore, it is preferable that the dispersant further has an acid value. The acid value of the dispersant, although depending on the presence and type of acidic group that is the source of the acid value, is more preferably 30 to 200 mgKOH / g, and even more preferably 50 to 150 mgKOH / g. Furthermore, the dispersant preferably has an amine value and an acid value, and further has a salt structure. The salt structure refers to a structure having a salt form such as an ammonium salt, a carboxylate salt, a phosphate ester salt, or a salt of a polyaminoamide and an acid polymer. The hydrophilic portion of the salt structure acts as an adsorption group for pigments and dyes, thereby increasing dispersibility and stability. Furthermore, the dispersant is preferably a polymeric dispersant. The term "polymeric dispersant" refers to a dispersant with a weight-average molecular weight of 1,000 or more. The molecular weight is preferably in the range of 1,000 to 100,000. By using a dispersant in the above range, both dispersion stability and developability can be achieved. Furthermore, in the present invention, unless otherwise specified, the weight-average molecular weight refers to the weight-average molecular weight (Mw) calculated in terms of polystyrene by GPC (gel permeation chromatography). Examples of dispersants include ANTI-TERRA (registered trademark)-U, U100, 204, and 205 from the ANTI-TERRA (registered trademark) series manufactured by BYK Chemie, DISPERBYK (registered trademark)-106, 108, 109, 112, 116, 140, 142, 145, 161, 162, 163, 166, 167, 168, 180, 182, 183, 185, 184, 2001, 2020, 2025, 2050, 2070, and 2150 from the DISPERBYK (registered trademark) series, and BYK (registered trademark)-9076 and 9077 from the BYK (registered trademark) series. Among these, ANTI-TERRA (registered trademark)-U, U100, 204, 205, and DISPERBYK (registered trademark)-101 are preferred because they have an amine value and an acid value. , 106, 140, 142, 145, 180, 2001, 2020, 2025, 2070, BYK (registered trademark)-9076 are preferred. Among these, ANTI-TERRA (registered trademark)-U, U100, 204, 205, DISPERBYK (registered trademark)-101, 106, 140, 142, 145, 180, and BYK (registered trademark)-9076 are more preferred because they have an amine value and an acid value and further have a salt structure. Of these, DISPERBYK (registered trademark)-106 is particularly preferred. By using the dispersant as described above, a colored photosensitive resin composition that can achieve high brightness can be obtained. In the colored photosensitive resin composition of the present invention, the content of the dispersant is not particularly limited and may be appropriately set depending on the purpose and application, but considering the balance between dispersion stability, durability (heat resistance, light resistance, weather resistance, etc.), transparency, etc., the content of the dispersant is preferably 1 to 30 parts by mass per 100 parts by mass of the total of the above-mentioned coloring materials. The content of the dispersant is preferably 3 to 25 parts by mass, more preferably 5 to 20 parts by mass. The amine value of a dispersant (based on effective solids) is expressed as the weight of KOH equivalent to the amount of base per gram of solids in the dispersant sample, excluding the solvent, and is measured using the following method: 0.5 to 1.5 g of dispersant sample is accurately weighed into a 100 mL beaker and dissolved in 50 mL of acetic acid. Using an automatic titrator equipped with a pH electrode, this solution is neutralized with a 0.1 mol / L HClO4 acetic acid solution. The inflection point on the titration pH curve is used as the titration endpoint, and the amine value is calculated using the following formula: Amine value [mgKOH / g] = (561 x V) / (W x S) (W: weight of dispersant sample [g], V: titration volume at the end of titration [mL], S: solids concentration of dispersant sample [wt%].) [solvent] The colorant used in the present invention preferably contains a solvent. The amount of the solvent in the colorant composition (colorant solution) is not particularly limited, but is preferably 20 to 95 parts by mass, more preferably 30 to 85 parts by mass, per 100 parts by mass of the colorant composition. The colored photosensitive resin composition preferably contains a solvent. The solvent is preferably used as a diluent or the like. Specifically, the solvent is preferably used to reduce viscosity and improve handling; to form a coating film by drying; as a dispersion medium for a colorant; and the like, and is a low-viscosity organic solvent or water that can dissolve or disperse each component contained in the colored photosensitive resin composition. The solvent may be any commonly used solvent and may be appropriately selected depending on the purpose and application, and is not particularly limited, but examples thereof include the following compounds, which may be used alone or in combination of two or more:Monoalcohols such as methanol, ethanol, isopropanol, n-butanol, and s-butanol; glycols such as ethylene glycol and propylene glycol; cyclic ethers such as tetrahydrofuran and dioxane; glycol monoethers such as ethylene glycol monomethyl ether, ethylene glycol monoethyl 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 monobutyl ether, and 3-methoxybutanol; glycol ethers such as ethylene glycol dimethyl ether, ethylene glycol diethyl ether, ethylene glycol ethyl methyl ether, diethylene glycol dimethyl ether, diethylene glycol diethyl ether, diethylene glycol ethyl methyl ether, propylene glycol dimethyl ether, and propylene glycol diethyl ether; ethylene glycol monomethyl ether acetate glycol monoether esters such as ethylene glycol monoethyl ether acetate, ethylene glycol monobutyl ether acetate, diethylene glycol monomethyl ether acetate, diethylene glycol monoethyl ether acetate, diethylene glycol monobutyl ether acetate, propylene glycol monomethyl ether acetate, propylene glycol monoethyl ether acetate, propylene glycol monobutyl ether acetate, dipropylene glycol monomethyl ether acetate, dipropylene glycol monoethyl ether acetate, dipropylene glycol monobutyl ether acetate, and 3-methoxybutyl acetate; alkyl esters such as methyl acetate, ethyl acetate, propyl acetate, isopropyl acetate, butyl acetate, methyl propionate, ethyl propionate, butyl propionate, methyl lactate, ethyl lactate, butyl lactate, methyl 3-methoxypropionate, ethyl 3-methoxypropionate, methyl 3-ethoxypropionate, ethyl 3-ethoxypropionate, methyl acetoacetate, and ethyl acetoacetate;Ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone, cyclohexanone, etc.; aromatic hydrocarbons such as benzene, toluene, xylene, ethylbenzene, etc.; aliphatic hydrocarbons such as hexane, cyclohexane, octane, etc.; amides such as dimethylformamide, dimethylacetamide, N-methylpyrrolidone, etc.; water, etc.

[0053] When forming pixels of a color filter, it is preferable to select a solvent having a boiling point in the range of 100 to 250° C. (under a pressure of 1013.25 [hPa]), and among these, glycol alkyl ether acetates are preferred. The amount of the solvent used may be appropriately determined depending on the purpose and application and is not particularly limited, but is preferably 10 to 90 mass % and more preferably 30 to 85 mass % relative to 100 mass % of the total amount of the colored photosensitive resin composition of the present invention. [Other ingredients] The colored photosensitive resin composition may further contain, depending on the required properties of the intended application, one or more of the following: dispersing aids; surfactants; heat resistance improvers; leveling agents; coupling agents; developing aids; fillers; thermosetting resins such as epoxy resins, phenolic resins, and polyvinylphenols; curing agents; release agents; reactive diluents; stabilizers; polymerization inhibitors; flame retardant aids; curing aids such as polyfunctional thiol compounds; chain transfer agents; fluorine-based additives; plasticizers; UV absorbers; antioxidants; matting agents; antifoaming agents; antistatic agents; slip agents; surface modifiers; thixotropic agents; thixotropic aids; quinone diazide compounds; polyphenol compounds; cationic polymerizable compounds; acid generators; quantum dot particles; other polymerizable monomers; crosslinking agents. The content ratio can be set depending on the required properties, but it is preferable that the content be 0.001 to 30% by mass of the total amount (100% by mass) of the colored photosensitive resin composition of the present invention. [Method for producing colored photosensitive resin composition] The colored photosensitive resin composition can be prepared by mixing and dispersing the above-described components using various conventional mixers or dispersers. In particular, it is preferable to first dissolve or disperse the colorant in a solvent (dispersion medium) to obtain a colorant solution (or a colorant dispersion if the colorant contains a pigment), and then mix the colorant solution with an alkali-soluble resin (preferably an alkali-soluble polymer), a photopolymerization initiator, and other components as needed to obtain a colored photosensitive resin composition. The colored photosensitive resin composition obtained in this manner further exhibits the effects of the present invention. This method includes a step of dissolving or dispersing the colorant in a solvent to obtain a colorant dispersion solution (also referred to as the "dispersion step"), and a step of mixing the dispersion solution with other components, such as an alkali-soluble polymer (also referred to as the "mixing step"). The dispersing step and the mixing step are not particularly limited and may be carried out by a conventional method, and may further include other steps that are conventionally carried out.

[0054] For example, predetermined amounts of colorant, solvent, and dispersant are weighed, and the colorant is dispersed in a dispersion process to prepare a colorant dispersion solution. This dispersion process can use a paint conditioner, sand grinder, ball mill, bead mill, roll mill, stone mill, jet mill, homogenizer, kneader, blender, or the like. This dispersion process microparticulates the colorant, improving its coating properties and, when the final product is a pixel on a color filter substrate, improving its transmittance. When dispersing the colorant, as described above, it is preferable to use a dispersant or dispersion aid as appropriate. When dispersing using a sand grinder, it is preferable to use glass beads or zirconia beads with a diameter of 0.1 to several mm. The temperature during dispersion is usually set to 0°C or higher, preferably room temperature or higher, and usually 100°C or lower, preferably 80°C or lower. The appropriate dispersion time varies depending on the composition of the colorant dispersion solution and the size of the sand grinder, so it can be adjusted appropriately. The dispersion step preferably involves kneading and dispersing the material using a roll mill, kneader, blender, or the like, followed by fine dispersion using a media mill, such as a bead mill filled with 0.01 to 1 mm beads. A composition (preferably a transparent liquid) containing an alkali-soluble resin, a polymerizable monomer, a photopolymerization initiator, and, if necessary, a solvent or leveling agent, which has been separately stirred and mixed, is added to the colorant dispersion solution (mill base) obtained by the dispersion step, and mixed to form a uniform dispersion solution, thereby obtaining a colored photosensitive resin composition. Since fine dust particles may be mixed in during the dispersion and mixing steps, it is preferable to filter the obtained colorant dispersion solution using a filter or the like. [Cured film] Next, the cured film formed using the colored photosensitive resin composition of the present invention will be described. The colored photosensitive resin composition of the present invention can form a cured film by irradiating (exposing) it with active energy rays. Specifically, for example, it is preferable to form a cured film by applying the colored photosensitive resin composition to a substrate, drying it, and irradiating (exposing) the coated surface with active energy rays. Thus, the cured film formed by the colored photosensitive resin composition also constitutes one aspect of the present invention. The shape of the cured film is not particularly limited, and it may be formed into a molded article such as a plate, sheet, film, or fiber. The film thickness is preferably 0.1 to 20 μm. When the film thickness is in this range, the film can be excellent in solvent resistance, image forming properties, and surface smoothness. The film thickness is more preferably 0.5 to 15 μm, and even more preferably 1 to 10 μm. The method for obtaining a cured film using the colored photosensitive resin composition of the present invention is not particularly limited, and any known method may be used. For example, a method may be used in which the above-described colored photosensitive resin composition is applied to a substrate, and the applied composition is dried, heated, or irradiated with energy rays such as ultraviolet rays to cure the composition, thereby obtaining a cured film. The substrate is not particularly limited and may be appropriately selected depending on the purpose and application. Examples include substrates made of various materials such as glass plates and plastic plates. The method for forming a coating film by applying the colored photosensitive resin composition is not particularly limited, and can be performed by a known method such as spin coating, slit coating, roll coating, or cast coating. After forming the coating film, the method includes a step of irradiating the coating film with light. The light irradiation method is not particularly limited and can be performed by a known method. Specifically, it can be performed by a method similar to the method described in the "Light irradiation step" of the "Color filter manufacturing method" described below. When the coating film is irradiated with light, the light irradiation may be carried out through a photomask. As the photomask, a mask having a light-shielding portion formed thereon according to the desired pattern may be used. When the light irradiation is carried out through a photomask, it is preferable to carry out a development step thereafter. By carrying out the development step, the desired pattern can be formed in the coating film. The development method is not particularly limited and can be carried out by a known method, and specifically, can be carried out by a method similar to the method described in the "development step" of the "method for producing a color filter" described below. After the light irradiation, the irradiated coating film is preferably heated to form a cured film. The heating temperature is preferably a low temperature at which the colorant (particularly the dye) is unlikely to decompose, and is preferably 200° C. or lower, more preferably 180° C. or lower. The lower limit of the heating temperature is preferably 85° C. or higher, more preferably 90° C. or higher, in order to maintain curability. The heating method other than the temperature is not particularly limited and can be performed by a known method, for example, a method similar to the method described in the "Heating step" of the "Color filter manufacturing method" described below. The cured film obtained by curing the colored photosensitive resin composition of the present invention and display device members having the cured film are preferably used in various optical components and electric / electronic devices, such as color filters, black matrices, photospacers, black column spacers, inks, printing plates, printed wiring boards, semiconductor elements, photoresists, insulating films, etc. used in liquid crystal, organic EL, quantum dot, and micro LED liquid crystal displays, solid-state imaging devices, touch panel type displays, etc. Among these, use in color filters is preferred. The present invention also includes a color filter having a cured film of the colored photosensitive resin composition on a substrate. The color filter will be described below. [Color filter] The color filter of the present invention has a configuration in which the above-described cured film is provided on a substrate. In the color filter, for example, a cured film formed from the above-described colored photosensitive resin composition is particularly suitable as a segment that requires coloring, such as a black matrix or each pixel of red, green, blue, yellow, etc. Substrates used in the color filters include, for example, glass substrates such as white plate glass, blue plate glass, alkali-strengthened glass, and silica-coated blue plate glass; sheets, films, or substrates made of thermoplastic resins such as polyester, polycarbonate, polyolefin, polysulfone, ring-opening polymers of cyclic olefins, and hydrogenated products thereof; sheets, films, or substrates made of thermosetting resins such as epoxy resins and unsaturated polyester resins; metal substrates such as aluminum plates, copper plates, nickel plates, and stainless steel plates; ceramic substrates; semiconductor substrates having photoelectric conversion elements; and components made of various materials such as glass substrates having a colorant layer on their surface (e.g., color filters for LCDs). Among these, glass substrates and sheets, films, or substrates made of heat-resistant resins are preferred from the standpoint of heat resistance. It is also preferred that the substrates be transparent. If necessary, the substrate may be subjected to corona discharge treatment, ozone treatment, or chemical treatment using a silane coupling agent or the like. [Color filter manufacturing method] To obtain the color filter, for example, it is preferable to employ a manufacturing method that includes, for each pixel color (i.e., for each pixel color), a step of disposing the colored photosensitive resin composition on a substrate (also referred to as a disposing step), a step of irradiating the colored photosensitive resin composition disposed on the substrate with light (also referred to as a light irradiation step), a step of developing with a developer (also referred to as a developing step), and a step of heat treatment (also referred to as a heat treatment step), and that repeats this same procedure for each color. Note that the order in which the pixels of each color are formed is not particularly limited. (1) Placement step (preferably application step) The disposing step is preferably carried out by coating. Examples of a method for coating the colored photosensitive resin composition on a substrate include spin coating, slit coating, roll coating, and cast coating, and any of these methods can be preferably used. In the disposing step, it is also preferable to dry the coating film after applying the colored photosensitive resin composition onto the substrate. The coating film can be dried using, for example, a hot plate, an IR oven, a convection oven, etc. The drying conditions are appropriately selected depending on the boiling point of the solvent components contained, the type of curable component, the film thickness, the performance of the dryer, etc., but it is usually preferable to perform the drying at a temperature of 50 to 160°C for 10 to 300 seconds. (2) Light irradiation process Examples of the light source for the actinic ray used in the light irradiation step include lamp light sources such as xenon lamps, halogen lamps, tungsten lamps, high-pressure mercury lamps, ultra-high-pressure mercury lamps, metal halide lamps, medium-pressure mercury lamps, low-pressure mercury lamps, carbon arcs, and fluorescent lamps, and laser light sources such as argon ion lasers, YAG lasers, excimer lasers, nitrogen lasers, helium cadmium lasers, and semiconductor lasers. Examples of the exposure system include the proximity system, mirror projection system, and stepper system, with the proximity system being preferred. In the step of irradiating with active energy rays, depending on the application, the active energy rays may be irradiated through a predetermined mask pattern. In this case, the exposed area is cured, and the cured area is made insoluble or hardly soluble in a developer. (3)Developing process The development step is a step in which, after the light irradiation step described above, development is performed with a developer to remove unexposed areas and form a pattern. This allows a patterned cured film to be obtained. The development treatment can usually be performed at a development temperature of 10 to 50°C by a method such as immersion development, spray development, brush development, or ultrasonic development. The developer used in the developing step is not particularly limited as long as it dissolves the colored photosensitive resin composition of the present invention, but an organic solvent or an alkaline aqueous solution is usually used, and a mixture thereof may also be used. When an alkaline aqueous solution is used as the developer, it is preferable to wash with water after development. Examples of organic solvents and alkaline aqueous solutions include those described in JP-A-2015-157909. (4)Heating process The heating step is a step (also referred to as a post-curing step) in which the exposed area (cured area) is further cured by baking after the above-mentioned development step. For example, a light source such as a high-pressure mercury lamp is used, and the cured area is further cured by baking at a temperature of, for example, 0.5 to 5 J / cm. 2 and a step of post-heating at a temperature of, for example, 60 to 200° C. for 10 seconds to 120 minutes. By carrying out such a post-curing step, it is possible to further increase the hardness and solvent resistance of the patterned cured film. The heating step is generally carried out at a temperature of about 200 to 260° C., but in the case of the colored photosensitive resin composition of the present invention, it is preferable to carry out sufficient curing under relatively low temperature conditions of 200° C. or less. As a result, it is possible to obtain a colorant containing a phthalocyanine dye that has excellent solvent resistance without impairing the color properties of the colorant. In the heating step, the heating temperature is preferably 180° C. or lower, and more preferably 130° C. or higher, more preferably 140° C. or higher, and even more preferably 150° C. or higher. The heating time in the heating step is not particularly limited, but is preferably 5 to 60 minutes, for example. The heating method is also not particularly limited, but can be performed using a heating device such as a hot plate, a convection oven, or a high-frequency heater. After going through this series of steps, the formation of a patterned image of one color is completed. This process is repeated in order to pattern black, red, green, and blue to form a color filter. Note that the order of patterning the four colors is not limited to the order described above. The thickness of the cured film obtained by the heating step (i.e., the colored cured coating film obtained by thermally curing the colored photosensitive resin composition) is preferably 0.1 to 20 μm, more preferably 0.5 to 15 μm, and even more preferably 1 to 10 μm. The color filter and its manufacturing method can be the method described in paragraphs 0066 to 0071 of JP-A No. 2013-130632. [Display device] The present invention also provides a display device comprising the above-described color filter. In addition, a display device member and a display device having a cured film formed from the colored photosensitive resin composition are also included in preferred embodiments of the present invention. The cured film formed from the colored photosensitive resin composition is stable and has good solvent resistance, as well as exhibits high smoothness, high transmittance, and can exhibit high brightness, making it particularly suitable as a colored cured film and resulting in excellent color characteristics for each pixel of a color filter.

[0055] As the display device, for example, a liquid crystal display device, a solid-state image pickup device, a touch panel display device, etc. are suitable. When the cured film is used as a member for a display device, the member may be a film-like single-layer or multi-layer member constituted by the cured film, or may be a member in which another layer is further combined with the single-layer or multi-layer member, or may be a member containing the cured film in its configuration.

[0056] As described above, the colored photosensitive resin composition of the present invention exhibits its functions by containing the above-mentioned specific components, and can provide a cured film that has good solvent resistance and high brightness. In particular, a synergistic effect is achieved by combining a phthalocyanine dye with a yellow colorant.

[0057] Therefore, the present invention can be suitably used for various applications in electrical and electronic equipment, such as various optical components and components used in liquid crystal, organic EL, quantum dot, and micro LED liquid crystal displays, solid-state imaging devices, and touch panel display devices. [Example]

[0058] The present invention will be described in further detail below with reference to examples and comparative examples. However, the following examples do not limit the present invention, and all modifications and variations within the scope of the present invention are included within the technical scope of the present invention. Unless otherwise specified, % means % by mass, and parts means parts by mass. Synthesis examples, preparation examples, evaluation methods, and results are specifically shown below. The physical properties of the alkali-soluble resin were evaluated as follows. [Evaluation method] (1) Weight average molecular weight (Mw) The weight average molecular weight (Mw) was measured by GPC (gel permeation chromatography) using polystyrene as a standard substance and tetrahydrofuran as an eluent on an HLC-8320GPC (manufactured by Tosoh Corporation) column: TSKgel SuperHZM-M (manufactured by Tosoh Corporation). (2) Acid value (AV) 3 g of the polymer solution was precisely weighed and dissolved in a mixed solvent of 90 g of acetone and 10 g of water, and titrated using a 0.1 N KOH aqueous solution as a titrant. The titration was carried out using an automatic titrator (product name: COM-1700A, manufactured by Hiranuma Sangyo Co., Ltd.), and the acid value per 1 g of solid content (mg KOH / g) was calculated from the acid value of the solution and the solid content of the solution. (3) Solid content (NV) Approximately 1 g of the polymer solution was weighed into an aluminum cup, dissolved in approximately 3 g of acetone, and then air-dried at room temperature. The solution was then dried in a hot air dryer (product name: PHH-101, manufactured by Espec Corporation) at 140°C under vacuum for 1.5 hours, cooled in a desiccator, and weighed. The solid content (% by mass) of the polymer solution was calculated from the mass loss. Synthesis Example 1 (Preparation of pigment dispersing resin) A separable flask equipped with a condenser was prepared as a reaction vessel. Meanwhile, 15 g of methyl (α-allyloxymethyl)acrylate (AMA), 31.5 g of MAA, 47 g of CHMA, 6.5 g of MMA, and 2 g of PBO were added as a monomer composition to a monomer dropping vessel and mixed with stirring. Furthermore, 3.2 parts of n-DM, 10.5 g of PGMEA, and 4.5 g of PGME were added as a chain transfer agent solution to a chain transfer agent dropping vessel and mixed with stirring. 130 g of PGMEA and 55.7 g of PGME were charged into the reaction vessel, and after purging with nitrogen, the reaction vessel was heated in an oil bath with stirring until the temperature reached 90°C. After the temperature of the reaction vessel stabilized at 90°C, the monomer composition and chain transfer agent solution were added dropwise. While maintaining the temperature at 90°C, the monomer composition was added dropwise over 180 minutes, and the chain transfer agent solution was added dropwise over 210 minutes. After the chain transfer agent solution had been added dropwise, 0.5 g of PBO was added. After another 30 minutes, the vessel was heated to 115°C. After maintaining the temperature at 115°C for 1 hour, a gas inlet tube was attached to the separable flask, and bubbling of a 7:93 (v / v) oxygen / nitrogen mixed gas began. Next, 33 g of GMA, 0.04 g of topanol as a polymerization inhibitor, and 0.4 g of DMBA as a catalyst were charged to the reaction vessel, and the mixture was reacted at 110°C for 1 hour and then at 115°C for 7 hours. After that, 38.2 g of PGMEA and 16.4 g of PGME were added, stirred, and cooled to room temperature to obtain a pigment dispersion resin containing 35.0 wt% resin. The pigment dispersion resin had a weight-average molecular weight (Mw) of 9000 and an acid value of 100 mgKOH / g. [Synthesis (preparation) of coloring materials] <Synthesis Example 2> (Synthesis of phthalocyanine green dye) (1) Process 1 A 2000 ml four-neck separable flask was charged with 108 g (0.54 mol) of tetrafluorophthalonitrile, 69.0 g (1.18 mol) of potassium fluoride, and 252 g of acetone. A dropping funnel was then charged with 254 g (1.1 mol) of 3-chloro-4-hydroxybenzoic acid methoxyethyl ester and 432 g of acetone. The reaction vessel was cooled on ice and stirred, and the 3-chloro-4-hydroxybenzoic acid methoxyethyl ester solution was added dropwise from the dropping funnel over approximately 2 hours. Stirring was then continued for another 2 hours. The reaction temperature was then slowly raised to room temperature while stirring overnight. The reaction solution was filtered, and the acetone was removed from the filtrate using a rotary evaporator. Methanol was added and recrystallization was carried out. The resulting crystals were filtered and dried in vacuo to obtain 217.4 g of intermediate (1) (yield: 64.8%). The reaction in step 1 is shown below in brief.

[0059] [ka] (2) Process 2 A 500 ml flat-bottom flask was charged with 150.0 g (0.2414 mol) of intermediate (1) obtained in step 1, 19.26 g (0.0603 mol) of zinc(II) iodide, and 225.0 g of benzonitrile. Then, under a nitrogen flow (10 ml / min), the reaction solution was stirred at 200 rpm using a flat stirring blade (2 cm length x 4 cm width x 2 mm width). The oil bath in which the flask was immersed was heated to 160 °C, and the phthalocyaninization reaction was carried out at that temperature. After the reaction was completed, 470 g of methyl cellosolve was added to the reaction solution, which was then added dropwise to a mixed solution of 3.8 kg of methanol and 0.6 kg of water to precipitate crystals. After suction filtration, a wet cake was obtained. The resulting cake was again stirred and washed with a mixed solution of 1.9 kg of methanol and 0.3 kg of water, and then suction filtered. The resulting cake was dried at 90° C. for 24 hours using a vacuum dryer, yielding 137.0 g (yield 89.1%) of the target phthalocyanine green dye. The reaction in step 2 is shown below in brief.

[0060] [ka] The phthalocyanine green dye obtained in Synthesis Example 2 (phthalocyanine (1) obtained by the above reaction) has a structure in which each of the moieties (total of eight) marked with "*" in the main skeleton in the above structure is substituted with the substituent shown on the right. Synthesis Example 3 (Preparation of Phthalocyanine Green Pigment Dispersion) 3.5 g of pigment dispersion resin (solids equivalent), 1.3 g of dispersant (manufactured by BYK-Chemie Japan, trade name "DISPERBYK-2001"; hereafter referred to as byk2001) (solids equivalent), and 8.0 g of pigment (manufactured by Heubach, trade name "CI Pigment Green 36") were weighed into a mayonnaise bottle and diluted with PGMEA to a solids concentration of 20% by mass. 64.0 g of zirconia beads with a diameter of 1 mm were added, the bottle was capped, and the mixture was shaken for 3 hours on a paint shaker to prepare a phthalocyanine green pigment dispersion. Synthesis Example 4 (Preparation of Nickel Azo Yellow Pigment Dispersion) 3.5 g of pigment dispersion resin (solids equivalent), 1.3 g of dispersant (manufactured by BYK-Chemie Japan, trade name "DISPERBYK-2001"; hereafter referred to as byk2001) (solids equivalent), and 8.0 g of pigment (manufactured by Lanxess, trade name "CI Pigment Yellow 150") were weighed into a mayonnaise bottle and diluted with PGMEA to a solids concentration of 20% by mass. 64.0 g of zirconia beads with a diameter of 1 mm were added, the bottle was capped, and the mixture was shaken for 3 hours on a paint shaker to prepare a nickel azo yellow pigment dispersion. <Synthesis Example 5> (Synthesis of pyridone azo yellow dye A) (1) Synthesis of azo dye intermediate (VIII) 37.0 g of sulfanilic acid was thoroughly stirred with 150 g of water and 32 g of concentrated hydrochloric acid, and then diazotized using 25 g of 4N sodium nitrite at 5-10°C. Next, 42 g of 1-butyl-1,2-dihydro-6-hydroxy-4-methyl-2-oxo-3-pyridinecarbonitrile was added to 370 g of water, and a solution adjusted to pH 8 with 2N sodium hydroxide was added to the coupling component while maintaining the temperature below 10°C. The pH was adjusted to 5.0 with sodium hydroxide to complete the coupling reaction. After the reaction was completed, the reaction was salted out using 100 g of sodium chloride. The precipitated product was filtered and dried to obtain 42.3 g (55 mol % based on sulfanilic acid) of the azo dye intermediate (VIII) shown below.

[0061] [ka] (2) Synthesis of sulfonic acid chloride (IX) Thionyl chloride was added dropwise to a suspension of 35 g of azo dye intermediate (VIII) in a mixed solvent of 15.6 g of dimethylformamide and 215.5 g of acetonitrile, which was stirred under ice cooling. After a while, the temperature was raised to 40°C and the suspension was stirred for an additional 4 hours. The suspension was then poured into 525 g of water with stirring and stirred for an additional 10 minutes. The resulting precipitate was collected by filtration and dried in vacuo at 60°C for several hours to obtain 20.4 g (56 mol % based on the azo dye intermediate) of the sulfonic acid chloride (IX) shown below.

[0062] [ka] (3) Synthesis of pyridone azo yellow dye A 20.4 g of sulfonic acid chloride (IX) was suspended in chloroform under ice cooling, and a mixed solution of 10.4 g of 2-ethylhexylamine and 27.2 g of triethylamine was slowly added dropwise. The mixture was warmed to room temperature and stirred for 10 minutes, after which the reaction solution was concentrated. The concentrated solution was dissolved in 105 g of acetone and poured into 420 g of 1 M hydrochloric acid, and the resulting precipitate was collected by filtration. This precipitate was dissolved in 280 g of methanol under reflux and slowly cooled to room temperature. The resulting precipitate was collected by filtration and then vacuum dried at 60°C for several hours to obtain 19.9 g (55 mol % based on the sulfonic acid chloride) of the following pyridone azo yellow dye A.

[0063] [ka] <Synthesis Example 6> (Synthesis of pyridone azo yellow dye B) The following pyridone azo yellow dye B was synthesized in the same manner as in the synthesis of the above yellow dye A, except that 1-butyl-1,2-dihydro-6-hydroxy-4-methyl-2-oxo-3-pyridinecarbonitrile was replaced with 1-ethyl-1,2-dihydro-6-hydroxy-4-methyl-2-oxo-3-pyridinecarbonitrile.

[0064] [ka] [Synthesis of alkali-soluble resin (alkali-soluble polymer)] <Synthesis Example 7> (Synthesis of alkali-soluble resin (A-1)) A separable flask equipped with a condenser was prepared as a reaction vessel. Meanwhile, 15 g of dimethyl-2,2'-[oxybis(methylene)]bis-2-propenoate (MD), 50.5 g of BzMA, 1 g of MMA, 33.5 g of MAA, 2 g of PBO, and 3.4 g of PGMEA were added as a monomer composition to a monomer dropping vessel and mixed with stirring. Furthermore, 2.3 g of n-DM and 13.4 g of PGMEA were added as a chain transfer agent solution to a chain transfer agent dropping vessel and mixed with stirring. 150 g of PGMEA was charged into the reaction vessel, and after purging with nitrogen, the reaction vessel was heated in an oil bath with stirring to raise the temperature to 90°C. After the temperature of the reaction vessel stabilized at 90°C, the monomer composition and chain transfer agent solution were added dropwise. The monomer composition and chain transfer agent solution were each added dropwise over 180 minutes while maintaining the temperature at 90°C. Thirty minutes after the dropwise addition was complete, 0.5 g of PBO was added. After another 30 minutes, the reactor was heated to 115°C. After maintaining the temperature at 115°C for 1.5 hours, a gas inlet tube was attached to the separable flask, and bubbling of a 7:93 (v / v) oxygen / nitrogen mixed gas began. Next, 33 g of GMA, 0.04 g of topanol as a polymerization inhibitor, and 0.4 g of DMBA as a catalyst were charged to the reactor, and the reaction was carried out at 110°C for 1 hour and at 115°C for 7 hours. 93.3 g of PGMEA was then added, stirred, and cooled to room temperature to obtain an alkali-soluble resin solution (A-1) with a double bond equivalent of 587 g / mol. Various physical properties (weight average molecular weight Mw, solids concentration NV, acid value per solid AV) of the resulting resin solution A-1 were measured. The results are shown in Table 1. <Synthesis Example 8> (Synthesis of alkali-soluble resin (A-2)) A separable flask equipped with a condenser was prepared as a reaction vessel. Meanwhile, 15 g of BzMI, 41.2 g of BzMA, 42.8 g of MAA, 1 g of MMA, 2 g of PBO, 10.5 g of PGMEA, and 4.5 g of PGME were added to the monomer addition vessel and stirred. 2.4 g of nDM, 1.7 g of PGMEA, and 0.7 g of PGME were added to the chain transfer agent addition vessel and stirred.

[0065] A reactor was charged with 130 g of PGMEA and 55.7 g of PGME, and the atmosphere was replaced with nitrogen. The reactor was then heated in an oil bath with stirring until the temperature reached 90°C. After the reactor temperature stabilized at 90°C, the monomer composition and chain transfer agent solution were added dropwise. The monomer composition and chain transfer agent solution were added dropwise over 180 minutes while maintaining the temperature at 90°C. Thirty minutes after the addition was complete, 0.5 g of PBO was added. After another 30 minutes, the reactor was heated to 115°C. After maintaining the temperature at 115°C for 1.5 hours, a gas inlet tube was attached to the separable flask, and bubbling with a 7 / 93 (v / v) oxygen / nitrogen mixed gas began. Next, 33 g of GMA, 0.04 g of topanol as a polymerization inhibitor, and 0.4 g of DMBA as a catalyst were added to the reactor, and the reaction was carried out at 110°C for 1 hour and then at 115°C for 7 hours. After that, 37.8 g of PGMEA and 16.2 g of PGME were added, and the mixture was stirred and mixed, then cooled to room temperature to obtain an alkali-soluble resin solution (A-2) with a double bond equivalent of 587 g / mol. Various physical properties (weight average molecular weight Mw, solids concentration NV, acid value per solid AV) of the resulting resin solution A-2 were measured. The results are shown in Table 1. <Synthesis Example 9> (Synthesis of alkali-soluble resin (A-3)) A separable flask equipped with a condenser was prepared as a reaction vessel. Meanwhile, 15 g of AMA, 41.2 g of BzMA, 1 g of MMA, 42.8 g of MAA, 2 g of PBO, 10.5 g of PGMEA, and 4.5 g of PGME were added to the monomer dropping vessel as a monomer composition and mixed with stirring. Furthermore, 2.4 g of n-DM, 1.7 g of PGMEA, and 0.7 g of PGME were added to the chain transfer agent dropping vessel as a chain transfer agent solution and mixed with stirring.

[0066] A reactor was charged with 130 g of PGMEA and 55.7 g of PGME. The reactor was then purged with nitrogen and heated in an oil bath with stirring until the temperature reached 90°C. After the reactor temperature stabilized at 90°C, the monomer composition and chain transfer agent solution were added dropwise. The monomer composition and chain transfer agent solution were added dropwise over 180 minutes while maintaining the temperature at 90°C, and the chain transfer agent solution was added dropwise over 210 minutes. Thirty minutes after the addition was complete, 0.5 g of PBO was added. After another 30 minutes, the reactor was heated to 115°C. After maintaining the temperature at 115°C for 1.5 hours, a gas inlet tube was attached to the separable flask, and bubbling with a 7 / 93 (v / v) oxygen / nitrogen mixed gas began. Next, 33 g of GMA, 0.04 g of topanol as a polymerization inhibitor, and 0.4 g of DMBA as a catalyst were added to the reactor, and the reaction was carried out at 110°C for 1 hour and then at 115°C for 7 hours. After that, 37.8 g of PGMEA and 16.2 g of PGME were added, and the mixture was stirred and mixed, then cooled to room temperature to obtain an alkali-soluble resin solution (A-3) with a double bond equivalent of 587 g / mol. Various physical properties (weight average molecular weight Mw, solids concentration NV, acid value per solid AV) of the resulting resin solution A-3 were measured. The results are shown in Table 1. <Synthesis Example 10> (Synthesis of alkali-soluble resin (A-4)) A separable flask equipped with a condenser was prepared as a reaction vessel. Meanwhile, 56.2 g of BzMA, 1 g of MMA, 42.8 g of MAA, 2 g of PBO, 19.7 g of PGMEA, and 8.4 g of PGME were added to the monomer dropping vessel as a monomer composition and mixed with stirring. 2.4 g of nDM, 1.7 g of PGMEA, and 0.7 g of PGME were added to the chain transfer agent dropping vessel as a chain transfer agent solution and mixed with stirring.

[0067] A reactor was charged with 130 g of PGMEA and 55.7 g of PGME, and the atmosphere was replaced with nitrogen. The reactor was then heated in an oil bath with stirring until the temperature reached 90°C. After the reactor temperature stabilized at 90°C, the monomer composition and chain transfer agent solution were added dropwise. The monomer composition and chain transfer agent solution were added dropwise over 180 minutes while maintaining the temperature at 90°C. Thirty minutes after the addition was complete, 0.5 g of PBO was added. After another 30 minutes, the reactor was heated to 115°C. After maintaining the temperature at 115°C for 1.5 hours, a gas inlet tube was attached to the separable flask, and bubbling with a 7 / 93 (v / v) oxygen / nitrogen mixed gas began. Next, 41 g of GMA, 0.2 g of topanol as a polymerization inhibitor, and 0.4 g of DMBA as a catalyst were added to the reactor, and the reaction was carried out at 110°C for 1 hour and then at 115°C for 7 hours. After that, 28.7 g of PGMEA and 12.3 g of PGME were added, and the mixture was stirred and mixed, then cooled to room temperature to obtain an alkali-soluble resin solution (A-4) with a double bond equivalent of 587 g / mol. Various physical properties (weight average molecular weight Mw, solids concentration NV, acid value per solid AV) of the resulting resin solution A-4 were measured. The results are shown in Table 1.

[0068] [Table 1] The abbreviations are as follows: BzMI: benzylmaleimide MD: dimethyl-2,2'-[oxybis(methylene)]bis-2-propenoate AMA: α-allyloxymethyl acrylate CHMA: Cyclohexyl methacrylate BzMA: benzyl methacrylate MAA: methacrylic acid MMA: Methyl methacrylate GMA: Glycidyl methacrylate DMBA: N,N-dimethylbenzylamine PBO: Perbutyl O n-DM: n-dodecyl mercaptan PGMEA: Propylene glycol monomethyl ether acetate PGME: Propylene glycol monomethyl ether [Preparation of Colored Photosensitive Resin Compositions Y-1 to Y-3] In all cases, the solids content (mass%) was 37.5 mass% of the alkali-soluble resin A-1, 37.5 mass% of dipentaerythritol hexaacrylate (DPHA) as a polymerizable monomer, 10 mass% of Omnirad907 (manufactured by BASF Japan Ltd.) as a photopolymerization initiator, 15 mass% of the yellow colorant obtained above, and further, PGMEA dilution solvent was added so that the solids content concentration of the colored photosensitive resin composition became 22 mass%, and the mixture was stirred to obtain colored photosensitive resin compositions (colored resin compositions) Y-1 to Y-3. [Evaluation of optical properties (brightness)] Each of the colored resin compositions Y-1 to Y-3 was applied to a 5 cm square glass substrate using a spin coater, dried at 90°C for 3 minutes, and then irradiated with 100 mJ / cm 2 of a high-pressure mercury lamp. 2 The resulting colored substrate was exposed to light at a 365 nm illuminance (equivalent to a 365 nm illuminance) and then heat-treated at 230°C for 30 minutes. The transmission spectrum of the resulting colored substrate was measured using a spectrophotometer, and the brightness evaluation results (comparison) when the chromaticity coordinate values ​​(x, y) in the CIE color system were adjusted to (x=0.410, y=0.490) using a D65 light source and a viewing angle of 10° are shown in Table 2.

[0069] [Table 2] *ΔY: (luminance of each thin film) - (luminance of thin film consisting of Y-1) <standard>) From the results of the luminance measurements, the coating film made of Y-3 had the largest ΔY, which means that the use of Y-3 as a yellow coloring material results in the highest luminance and a high light transmittance. [Preparation of Colored Photosensitive Resin Compositions G-1 to G-7] In each case, the solids content (mass%) was 37.5 mass% of the alkali-soluble resin, 37.5 mass% of dipentaerythritol hexaacrylate (DPHA) as a polymerizable monomer, 10 mass% of Omnirad907 (BASF Japan) as a photopolymerization initiator, 15 mass% of the green colorant obtained by the synthesis (preparation) described above, and a dilution solvent, PGMEA (propylene glycol monomethyl ether acetate), was added to the mixture so that the solids content of the colored photosensitive resin composition was 22 mass%. The colored photosensitive resin compositions G-1 to G-7 of Examples 1 to 4 and Comparative Examples 1 to 3 were obtained by stirring. The composition and composition ratio of each component are shown in Table 3.

[0070] [Table 3] *Omn907: Omnirad907, 2-methyl-1-[4-(methylthio)phenyl]-2-morpholinopropan-1-one *DPHA: Dipentaerythritol hexaacrylate [Evaluation of solvent resistance] The obtained colored photosensitive resin compositions G-1 to G-7 were spin-coated onto a 5 cm square glass substrate, dried at 90°C for 3 minutes, and then irradiated with 100 mJ / cm 2 of a high-pressure mercury lamp. 2 The coating was exposed to light at a 365 nm illuminance (equivalent to a 365 nm illuminance) and then heat-treated at 230°C for 30 minutes to obtain a 3 μm-thick thin film. The coating was then immersed in 20 g of 1-methyl-2-pyrrolidone (NMP) at 50°C for 10 minutes, and the hue of the NMP eluted from the coating was measured using a UV-3600 spectrophotometer (Shimadzu Corporation) to determine the absorbance at 697 nm (dye systems in Examples 1 to 4) or 716 nm (pigment systems in Comparative Examples 1 to 3). The amount of colorant leaching from the glass substrate was evaluated by measuring the absorbance of the NMP immersion solution after the test. The results are shown in Table 4. A lower measured value indicated less leaching of the colorant component and was evaluated as having good solvent resistance.

[0071] [Table 4] [Evaluation of optical properties (xy values)] The obtained colored photosensitive resin compositions G-1 to G-7 were applied onto a 5 cm square glass substrate in an amount of 0.1 to 0.8 mg / cm in terms of solid content. 2 After drying at 90°C for 3 minutes, the coating was irradiated with a high-pressure mercury lamp at 100 mJ / cm 2 The thin films were exposed to a 365 nm illuminance and then heat-treated at 230°C for 30 minutes to obtain thin films with different thicknesses. The chromaticity coordinates (x, y) of the thin films in the CIE color system were measured using a spectrophotometer CM-3700A (Konica Minolta) under a D65 light source and a viewing angle of 10°. Table 5 shows the chromaticity coordinates, and Figure 2 shows the xy plot.

[0072] [Table 5] [xy plot] From the xy plots (FIG. 2) of Example 1 and Comparative Example 1, it was confirmed that the y value of the phthalocyanine dye of the present invention does not change depending on the film thickness. In the xy chromaticity diagram of the CIE color system, the larger the value on the y axis, the higher the proportion of "greenness," and the smaller the value, the higher the proportion of "blueness." Incidentally, since the green component can be divided into a blue component and a yellow component, it was confirmed that the phthalocyanine dye of the present invention has a lower proportion of yellow component than the phthalocyanine pigment of Comparative Example 1. From this, it is possible to increase the brightness of a colored photosensitive resin composition by combining a phthalocyanine dye with a highly bright yellow colorant. [Preparation of Colored Photosensitive Resin Compositions GY-1 to GY-21] In all cases, the solids content (mass%) was 37.5 mass% of the alkali-soluble resin, 37.5 mass% of dipentaerythritol hexaacrylate (DPHA) as a polymerizable monomer, 10 mass% of Omnirad907 (BASF Japan) as a photopolymerization initiator, and 15 mass% of the total amount of the coloring materials obtained above. Furthermore, a dilution solvent, PGMEA (propylene glycol monomethyl ether acetate), was added so that the solids content of the colored photosensitive resin composition became 22 mass%, and the mixture was stirred to obtain the colored photosensitive resin compositions of Examples 5 to 16 and Comparative Examples 4 to 12. The composition and composition ratio of each component are shown in Tables 6 and 7.

[0073] [Table 6]

[0074] [Table 7] [Evaluation of optical properties (brightness)] The obtained colored photosensitive resin compositions GY-1 to GY-21 were spin-coated onto a 5 cm square glass substrate, dried at 90°C for 3 minutes, and then irradiated with 100 mJ / cm 2 of a high-pressure mercury lamp. 2 The thin film was exposed to light at a 365 nm illuminance (equivalent to a 365 nm illuminance) and then heat-treated at 230°C for 30 minutes to obtain a 3 μm-thick thin film. The thin film was measured using a spectrophotometer CM-3700A (Konica Minolta) with a D65 light source and a viewing angle of 10°, and the chromaticity coordinates (x, y) in the CIE color system were set to (x = 0.295, y = 0.595). The luminance evaluation results (comparison) are shown in Table 8, and the ΔY plot is shown in Figure 3. *ΔY: (brightness of each thin film) - (brightness of each standard thin film) The greater the ΔY is from the standard, the higher the brightness (light transmittance).

[0075] [Table 8] The evaluation results (Tables 4, 5, and 8) of the thin films obtained by curing each of the colored photosensitive resin compositions of the Examples and Comparative Examples (Tables 3, 6, and 7) confirmed the superiority of the colored photosensitive resin composition of the present invention. In particular, a comparison of Examples 1 to 4 with Comparative Examples 1 to 3 in Table 4 confirmed that a phthalocyanine dye (phthalocyanine-based green dye) used as a colorant, rather than a green pigment, in combination with an alkali-soluble resin can form a cured film with less colorant bleeding and excellent solvent resistance. Furthermore, a comparison of Examples (7, 10, and 13) with Comparative Examples (6, 9, and 12) in Table 8 confirmed that a phthalocyanine dye used as a colorant, rather than a green pigment, in combination with an azo-based yellow colorant can form a cured film with high brightness and excellent light transmittance. This tendency was also confirmed in Examples (5, 8, and 11) and Examples (6, 9, and 12) containing other alkali-soluble resins. It should be noted that combining the azo-based yellow coloring material with yellow dye A or yellow dye B was more effective in increasing brightness than using a pigment. Furthermore, by comparing yellow dye A and yellow dye B, it was confirmed that the higher the brightness of the yellow colorant combined with the phthalocyanine dye, the larger ΔY becomes, and the greater the effect of improving brightness becomes. Figure 1 shows an example of the absorption spectrum of a coating film containing only a phthalocyanine green dye as a colorant. Compared to the absorption spectrum containing a commercially available green pigment, it shows a high transmittance in the region of 480 to 520 nm (calculated from absorbance). These optical characteristics make it easy to achieve improved brightness as a color filter (green pixel) when combined with a yellow colorant or depending on the backlight specifications. The phthalocyanine dye of the present invention has a specific structure, and when the absorbance at the absorption maximum wavelength is taken as 1, the light transmittance at a wavelength of 480 nm is 85% or more, which is thought to result in a bright green pixel. [Industrial Applicability]

[0076] Display device members such as color filters having a highly luminous colored cured film formed from the colored photosensitive resin composition of the present invention can be suitably used in the fields of optics and electrical and electronics.< / standard>

Claims

1. A colored photosensitive resin composition comprising a colorant, an alkali-soluble resin, and a photopolymerization initiator, The colorant is represented by the following general formula (IV): 【Chemistry 1】 (In formula (IV), M represents a metal atom, a metal oxide, or a metal halide. X １ ~X ４ and Y １ ~Y ４ are the same or different and each represents a fluorine atom or an OR １０ represents a group, provided that X １ and Y １ At least one of X ２ and Y ２ At least one of X ３ and Y ３ and at least one of X ４ and Y ４ At least one of １０ represents a group. １０ is a phenyl group, and the phenyl group has a substituent selected from a methoxyethoxycarbonyl group, a halogen group, a cyano group, and a nitro group. The phthalocyanine dye is represented by The alkali-soluble resin is a polymer having a monomer unit capable of introducing a ring structure into the main chain skeleton, the monomer unit being selected from an N-substituted maleimide monomer unit, a dialkyl-2,2'-(oxydimethylene)diacrylate monomer unit, and an α-(unsaturated alkoxyalkyl)acrylate monomer unit.

2. 2. The colored photosensitive resin composition for color filters according to claim 1, wherein M in the structural formula of the phthalocyanine dye is a metal atom selected from Co, Ni, Cu, and Zn.

3. 3. The colored photosensitive resin composition for color filters according to claim 1, wherein the phthalocyanine dye has a light transmittance of 85% or more at a wavelength of 480 nm when the absorbance at the absorption maximum wavelength is taken as 1.

4. 4. The colored photosensitive resin composition for color filters according to claim 1, wherein the coloring material further comprises a yellow coloring material.

5. 5. The colored photosensitive resin composition for color filters according to claim 4, wherein the yellow coloring material is an azo-based yellow dye or an azo-based yellow pigment.

6. 6. The colored photosensitive resin composition for color filter according to claim 1, wherein the content of the monomer unit capable of introducing a ring structure into the main chain skeleton in the alkali-soluble resin is 2 to 40 mass% relative to 100 mass% of all monomer units.

7. 7. The colored photosensitive resin composition for color filters according to claim 1, further comprising a polymerizable monomer.

8. A cured film obtained by curing the colored photosensitive resin composition for color filters according to any one of claims 1 to 7.

9. A member for a display device, comprising the cured film according to claim 8 .

10. A color filter having the cured film according to claim 8 on a substrate.

11. A display device comprising the member for a display device according to claim 9 or the color filter according to claim 10.

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