TW201235784A - Coloring photosensitive resin composition - Google Patents

Abstract

Disclosed is a coloring photosensitive resin composition, containing a colorant, resin, a polymerizable compound, a polymerization initiator and a solvent, where the colorant contains dyes and pigments, the solvent contains dipropylene glycol monomethyl ether acetate; decompression drying is performed after the coloring photosensitive resin composition of the present invention is applied on a substrate, so as to reduce formation of crater defects on the dried coating film as manufactured.

Description

201235784 6. Description of the Invention: [Technical Field of the Invention] The present invention relates to a colored photosensitive resin composition. [Prior Art] The colored photosensitive resin composition is used for the production of a color filter used in a display device such as a liquid crystal display panel, an electroluminescence panel, or a plasma display panel. In Japanese Patent Laid-Open Publication No. 2010-32999, it is known to contain a ruthenium P star dye and a pigment as a colorant, and to contain propylene glycol monomethyl ether acetate and 4-hydroxy-4-methyl-2-pentanone. A colored photosensitive resin composition as a solvent. SUMMARY OF THE INVENTION When a colored photosensitive resin composition is applied onto a substrate and then dried under reduced pressure to form a dried coating film, a crater-like defect may occur. SUMMARY OF THE INVENTION An object of the present invention is to provide a colored photosensitive resin composition which produces less crater-like defects. [Technical means for solving the problem] The present invention provides the following [1] to [5]. [1] A colored photosensitive resin composition containing a colorant, a resin, a polymerizable compound, a polymerization initiator, and a solvent, wherein the colorant contains xanthenedye and a pigment, and the solvent contains two Dipp〇pylene glyc〇1 monomethylether acetate. [2] The colored photosensitive resin composition according to the above [1], wherein the content of dipropylene glycol mono 161707.doc 201235784 formazan acetate in the solvent is 〇.丨% by mass or more and 3% by mass or less. [3] The colored photosensitive resin composition according to the above [1] or [2] wherein the solvent further contains ethyl lactate. [4] The colored photosensitive resin composition according to the above [3], wherein the solvent further contains propylene glycol monoterpene ether and/or propylene glycol monomethyl ether acetate. [5] The colored photosensitive resin composition according to any one of the above [4], wherein the resin is a soluble resin. [6] The colored photosensitive resin composition according to any one of [1] to [5] wherein the polymerizable compound is (meth) acrylate. [7] A color filter formed by the color photosensitive resin composition according to any one of the above (1) to [6]. [8] A display device which contains the color filter as described in [7] above. Even if the colored photosensitive resin composition of the present invention is applied onto a substrate and dried under reduced pressure and dried to prepare a coating film, the occurrence of crater-like defects is less. [Embodiment] The colored photosensitive resin composition of the present invention contains a colorant (4), a resin (8), a polymerizable compound (rhodium, a polymerization initiator (9), and a solvent (8), and the colorant (4) contains a pigment and a dye, and the solvent contains Diethylene glycol monomethyl ether acetate. The coloring photosensitive resin of the present invention is a pigment and a bismuth dye. The coloring agent (Α) used in the composition of the pigment is exemplified as an organic pigment and an inorganic pigment. Refers to the compound classified as a pigment in 161707.doc 201235784 (published by The Society of Dyers and Colourists), wherein 'preferably an organic pigment. As the organic pigment, specifically, for example, C I. (c〇l〇ur Index, color index) Pigment Yellow 1, 3, 12, 13, 14, 15, 16, 17, 2, 24, 31, 53, 83, 86, 93, 94, 1〇9, Yellow pigments such as 110, 117, 125, 128, 137, 138, 139, 147, 148, 150, 153, 154, 166, 173, 194, 214; C·1. Pigment orange 13, 31, 36, 38, 40 , 42, 43, 51, 55, 59 61, 64, 65, 71, 73, etc. Pigment; C-Ι. Pigment Red 9, 97, 105, 122, 123, 144, 149, 166 (10), 175, 176, 177, 180, 192, 209, 215, 216, 224, 242, 254 '255, 264 , 265 and other red pigments; CI pigment blue 15, 15: 3, 15: 4, 15: 6, 6 〇, 8 〇 and other blue pigments 'ci pigment purple】, 19, 23, 29, 32, 36, 38, etc. Purple pigment; C-Ι. Pigment green 7,36,58 and other green pigments; CJ. Pigment brown 23,25 and other brown pigments; and CI pigment black 1,7 and other black pigments. # Among them, preferably ci pigment blue 15 , 15 : 3, 15 : 4, 15 : 6, 60, 80 and other blue pigments, α i pigment purple i, 19, 23, 29, 32, ^, and other purple pigments, more preferably containing selected from [• pigment purple 23, c work. Pigment blue 15: 3 and c · 1. Pigment blue 15: 6 of the group of at least a kind of pigment, and further preferably contains C.1. Pigment blue 15: 6 pigment. These pigments and hawthorn dye combinations can be used to obtain color calenders having excellent heat resistance and color properties. These pigments can be used singly or in combination of two or more. 16l707.doc 201235784 The above pigments can also be carried out as needed. a surface treatment such as a fat treatment, a pigment derivative or a pigment dispersant introduced with an acidic group or a basic group, a graft treatment of a pigment surface by a polymer compound or the like, a micronization treatment by a sulfuric acid micronization method, or the like, Alternatively, the cleaning treatment using an organic solvent or water for removing impurities, the ionic impurities, the removal treatment by an ion exchange method or the like may be employed. X ' is preferably such that the particle diameter of the pigment is uniform. By performing a dispersion treatment by containing a pigment dispersant, a pigment dispersion liquid in which the pigment is uniformly dispersed in a solution can be obtained. As the pigment dispersant, a commercially available surfactant can be used, and examples thereof include polyfluorene-based, fluorine-based, ester-based, cationic, anionic, nonionic, amphoteric, polyester, and polyamine. , surfactants such as acrylics, etc. As the above surfactant, in addition to polyoxyethylene alkyl ethers, polyoxyethylene alkyl benzene, polyethylene glycol s, sorbitol liver fatty acid esters, fatty acid modified polyesters, tertiary amines Others, such as modified polyurethanes, polyethyleneimine, etc., can be listed by brand name: κρ (manufactured by Shinji Shogi Co., Ltd.) Fl〇wlen (manufactured by Kyoeisha Chemical Co., Ltd.), S〇lsperse (made by Zeneca Co., Ltd.), manufactured by efka (1), Ajisper (Ajinomoto Precision Technology (Ajin〇m〇t〇)

Techno) Co., Ltd.), msperbyk (BYK Chemical (7)

Chemie) manufactured by the company). These may be used alone or in combination of two or more. In the case of using a pigment dispersant, the amount thereof is preferably 100 parts by mass or less, more preferably 5 to 5 parts by mass, per part by mass of the pigment. When the amount of the pigment dispersant used is in the above range, there is a tendency to obtain a uniform dispersion of the pigment dispersion in the state of 161707.doc 201235784. The Yamaguchi star dye contains a dye having a compound called a skeleton. As the star dye, for example, CI. Acid Mm "; 94 "89' U-Rhodan 6G), 2, 3, 4, S η Τ Red, C.1·Basic Red 10 (Rudan)明Β), ”'^.Experimental Violet 1., 11, 25, 0.1.^...,..^” 2 To 7 Straight C.1. Reactive Red 36 (Bangladesh Rose Soul... Item Ji Ruo Danming G, ^ 特 开 · 32 32 32 32 32 32 32 32 32 32 32 32 32 32 32 32 32 32 32 32 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 a dye (hereinafter sometimes referred to as "compound (1)"). Compound (1) is also a tautomer thereof. In the case of using compound (1), the content of compound (1) is preferably relative to the total amount of star dye 5 % by mass or more, more preferably: 〇 by mass or more, further preferably 90% by mass or more, and particularly preferably: substantially only the compound (1) is used as the ρ-Hawthorn dye.

A® (1) a (Xe) [In the formula (1), Ri to R4 each independently represent a hydrogen atom, a carbon number (tetra), a valence saturated hydrocarbon group or a carbon number of 6 to Η). The aldehyde group of the valence group, the hydrogen atom contained in the aromatic smog group can be _ 素 atoms, _R8, _〇H, _〇R8, -S03H, -SCVM+, -C〇2H, .c〇2-M+ , _c〇2R8, _sr38, -SOW, ·δ〇3ι^_δ〇2ΝιΛΐ0 replaced. The saturated atomic group containing 16l707.doc 201235784 may be replaced by an aromatic hydrocarbon group or a functional atom having 6 to 10 carbon atoms, and the hydrogen atom contained in the aromatic hydrocarbon group may be substituted by an alkoxy group having a carbon number of 丨3. The above saturated hydrocarbon group may be substituted by VII, {small or 氺.... R1 and R2 may together form a ring containing a nitrogen atom, and r3&r4 may also form a ring containing a nitrogen atom. -C02H, -CO: R represents -OH, -S03-, -S03H, -S03.M+, M+, -C02R8, _s〇3R8 or -so2nr9r10 〇 m represents an integer of 〇 5. In the case where the claw is 2 or more, the plurality of r5s are the same or different from each other. R and R7 each independently represent a hydrogen atom or an alkyl group having 1 to 6 carbon atoms. M+ represents +N(RU)4, Na+ or K+»X represents a halogen atom. a represents an integer of 0 or 1. R represents a monovalent saturated hydrocarbon group having 1 to 20 carbon atoms, and the hydrogen atom contained in the saturated hydrocarbon group may be substituted by a halogen atom. R11 each independently represents a hydrogen atom, an i-valent saturated hydrocarbon group having a carbon number of 丨2 or 2, or an aralkyl group having a carbon number of 7 to 10. R and R1G each independently represent a hydrogen atom or a valence saturated hydrocarbon group having a carbon number of (~(10), and the hydrogen atom contained in the saturated hydrocarbon group may be substituted by a hydroxyl group or a dentate atom. _CIl2 contained in the saturated aliphatic hydrocarbon group It may be substituted by _〇_, _c〇_, -NH- or -NR8-, and R9 and Ri〇 may be bonded to each other to form a heterocyclic ring of a 3 to 10 member ring containing a nitrogen atom]. Examples of the monovalent aromatic hydrocarbon group having a carbon number of 6 to 中 in R to R include, for example, a phenyl group, an anthranilyl group, a xylyl group, a propylphenyl group, and a butylbenzene 161707.doc 201235784 Wait. The monovalent aromatic hydrocarbon group having 6 to 10 carbon atoms in R1 to R 4 is preferably selected from the group consisting of -so3, _s〇3h, _s〇3.m+&_s〇2Nr9r1. At least one of the constituent groups is preferably a substituent selected from the group consisting of _sc^.M+& ♦nry. At least one of the constituent groups is a substituent. In this case, _S03·Μ is preferably _S〇3-+N(Rll)4. When R1 to R4 are these groups, a color filter which is less likely to be formed into a foreign color of the coloring photosensitive resin composition of the present invention containing the object (1) and which is excellent in heat can be used. Examples of the ring formed by R1 and R2- and the ring formed by the same as RW may be exemplified by the following. ^ Ρ -Ο X) X}

乍 is a monovalent saturated hydrocarbon group of 碳 之 RR in RR, and examples thereof include methyl 'ethyl, propyl, isopropyl, butyl, isobutyl, pentyl, isopentyl, neopentyl, hexyl, Heptyl, octyl, 2-ethylhexyl, decyl, decyl, dodecyl, hexadecyl, eicosyl, etc., alkyl having 1 to 20 carbon atoms, cyclopropyl, cyclopentyl, An alicyclic saturated hydrocarbon group having 3 to 20 carbon atoms such as a cyclohexyl group, a cycloheptyl group, a cyclooctyl group or a tricyclodecyl group. Examples of -OR8' include a decyloxy group, an ethoxy group, a propoxy group, a butoxy group, a pentyloxy group, a hexyloxy group, a heptyloxy group, an octyloxy group, a 2-ethylhexyloxy group, and Alkoxy group and the like. 161707.doc 201235784 Examples of -co2r include, for example, a methoxy group, an ethoxy group, a propoxy group, a third butoxy group, a hexyloxy group, and a hexyloxycarbonyl group. Wait. Examples of -SR8' include a methylthio group, an ethylthio group, a butylthio group, a hexylthio group, a mercaptothio group, and an eicosylthio group. Examples of -S〇2R8 include a methylsulfonyl group, an ethylsulfonyl group, a butyl group, a hexyl sulfonyl group, a decylsulfonyl group, and an eicosylsulfonyl group. Examples of -SC^R8 include a decyloxysulfonyl group, an ethoxysulfonyl group, a propoxysulfonyl group, a third butoxysulfonyl group, a hexyloxysulfonyl group, and an eicosane. Oxysulfonyl and the like. As -S〇2NR9Rl(), for example, an amine sulfonyl group; N-methylamine sulfonyl group, N-ethylamine sulfonyl group, N-propylamine sulfonyl group, N-isopropylamine Sulfonyl, ν·butylamine sulfonyl, N-isobutylamine sulfonyl 'N-t-butylamine sulfonyl' N-t-butylamine sulfonyl, N-pentylamine Sulfonyl, N-(l-ethylpropyl)amine sulfonyl, dimethyl propyl) sulfonyl, N-(l,2-dimethylpropyl)amine sulfonyl, N_( 2,2_Dimercaptopropyl)aminesulfonyl, N-(l-methylbutyl)aminesulfonyl, n-(2-mercaptobutyl)aminesulfonyl, N-(3-A Alkyl butyl) sulfonyl sulfonyl, fluorene cyclopentylamine sulfonyl sulfonyl, fluorenyl-hexylamine sulfonyl sulfhydryl, N-(l,3-dimethylbutyl)amine sulfonyl hydrazine Ν (3,3 - Dimercaptobutyl)amine fluorenyl, hydrazine-heptylamine fluorenyl' ν·(ι_曱ylhexyl)amine sulfonyl, N-(l,4-didecylpentyl)amine sulfonate Sulfhydryl, Ν-octylamine hydrazino, Ν-(2-ethylhexyl)amine sulfhydryl, N-(l,5-dimethyl)hexylamine sulfonyl, >^-(1, 1,2,2-tetramethylbutylamine sulfonyl group, etc. 1^_1 substituted amine 161707.doc -10- 201235784 醢基基; and N , N--decylamine sulfonyl, N,N-ethylmethylamine sulfonyl, n,n-diylamine κ, n,N-propylmethylamine, n, N-isopropyl decylamine sulfonyl, N, N't-butyl decyl sulfonyl sulfonyl, N, N-butyl ethylamine n soil N'N-bis (1-methyl propyl) An amine sulfonyl group substituted with an N, N-2 or the like such as an amine fluorenyl group or an n,N-heptylmethylamine sulfonyl group. In the monovalent saturated hydrocarbon group having 1 to 20 carbon atoms of R and R, the hydrogen atom contained in the saturated hydrocarbon group may be substituted by _〇H or a halogen atom, and the -CH2- contained in the saturated hydrocarbon group may be _〇_, _c〇_, _NH• or _nr8_ replaced. R and R may be bonded to each other to form a heterocyclic ring containing a 3 to 1 member ring of a nitrogen atom. As the heterocyclic ring, for example, the following may be mentioned.

/ Θ - O JO R5 is preferably -co2H, -co2r8, -so3-, -so3 M+, -so3H or S02NHR9, more preferably S03-, -SO/M+, -so3h or S02NHR9. m is preferably from 1 to 4, more preferably 1 or 2. Examples of the alkyl group having 1 to 6 carbon atoms in R6 and R7 include the above-mentioned alkyl group t having 1 to 6 carbon atoms. Examples of the aralkyl group having 7 to 10 carbon atoms in R11 include a benzyl group, a phenylethyl group, and a phenylbutyl group. M+ is +N(Rn)4, Na+ or K+, preferably +N(Rn)4 〇 as +N(Rn)4' is preferably 4 R1^, at least 2 are carbon number 5~2〇 A monovalent saturated hydrocarbon group. Further, the total carbon number of the four R11 is preferably from 20 to 80, more preferably from 20 to 60. In the case where the compound (1) is present, if R11 is a color-sensitive photosensitive resin of I6l707.doc -11 - 201235784, the base material of the present invention contains a color filter having less foreign matter from the composition of the present invention containing the compound (1). The compound (1) is preferably a compound (7) represented by the formula (2), which is called (four), and is sometimes referred to as the author. The character mu & Gan is preferably contained in the compound (2). When the compound (7) is used, the content of the compound (7) in the dye is preferably 50% by mass or more, more preferably 70% by mass or more, and still more preferably 90% by mass or more. For this, only compound (2) was used as the yaw dye.

[In the formula (2), R 2i to R24 each independently represent a hydrogen atom +, _r26 or a monovalent aromatic hydrocarbon group having 6 to 1 carbon atoms, and the hydrogen atom contained in the aromatic hydrocarbon group may be -so3·, -so3 Ma+, -so3H, -so3R26 or -S〇2NHR26 are substituted.乂3 represents a halogen atom. Al represents an integer of 〇 or 1. Ml represents an integer of 〇~5. In the case where mi is an integer of 2 or more, plural R25s are the same or different from each other.

Ma+ represents +N(R27)4, Na+ or K+. R25 represents -S03·, -SO/Ma+, -so3h or S02NHR26. R26 represents a monovalent saturated hydrocarbon group having 1 to 20 carbon atoms. R27 each independently represents a monovalent saturated hydrocarbon group or a benzyl group having 1 to 20 carbon atoms. 161707.doc -12-201235784 A monovalent aromatic nicotinyl group having 6 to 10 carbon atoms in R21 to R24 is the same as those exemplified as the aromatic hydrocarbon group in R1 to R4. Wherein, the combination of R21 to R24 is preferably a ruler 2 and the group 23 is a nitrogen atom, and R22 and R24 are an valence-valent aromatic hydrocarbon group having a carbon number of (7), and the hydrogen atom contained in the aromatic hydrocarbon group can be -S〇3·, -SCVM+, -S〇3H, ·8〇3Κ26 or -so2nhr26 are substituted. More preferably, R2i & R23 is a hydrogen atom, and r22 and R24 are a monovalent aromatic hydrocarbon group having 6 to 10 carbon atoms, and the hydrogen atom contained in the aromatic hydrocarbon group may be substituted by -SCVM+ or SOZNHR26. When the ruler 2 is a base, the colored photosensitive resin composition of the present invention containing the compound (7) can be used to form a color filter excellent in heat resistance. Examples of the carbon number 1 to "the valence-saturated hydrocarbon group in R26 and R27 include the same groups as those of the saturated hydrocarbon group in R8 to R11. When R21 to R24 are -R26, it is preferably inferior. 26 is independently a hydrogen atom, a methyl group or an ethyl group. R26 of -S〇3R26 and -SOAhr26 is preferably a branched alkyl group having a carbon number of 3 to 2 Å, more preferably a carbon number of 6 to 12. The branched alkyl group is more preferably a 2-ethylhexyl group. When R26 is such a group, the colored photosensitive resin composition containing the compound (2) can form a color filter having less foreign matter generation.

Ma+ is +N(R27)4, Na+ or K+, preferably +N(R27)4. Preferably, at least two of the carbon atoms of +N(R27)4' are a valence saturated hydrocarbon group. Further, the total carbon number of the four r27 is preferably from 20 to 80, more preferably from 20 to 60. In the case where +N(R27)4 is present in the compound (2), the colored photosensitive resin composition of the present invention containing the compound (2) having R as the group can form a color filter having less generation of foreign matter. I6I707.doc • Π· 201235784 As a compound (1, for example, a servant 铷 举 举 举 举 举 举 举 举 举 举 举 举 举 举 举 举 举 举 举 举 举 举 举 举 举 举 举 举 举 举 举 举

The Ka-representing number 1 to 20 monovalent saturated group' preferably represents a carbon number of 6 to 12 and is further a chain alkyl group, and more preferably represents a 2-ethylhexyl group. Among these, it is preferably a CL acid red 289 bismuth amide, a CI acid red 289 quaternary salt, a C J acid violet 〇2 continuation aminide or a C_I. acid violet 102 quaternary ammonium salt. Examples of such a compound include a compound represented by the formula U·1) to the formula (1-8), the formula (1-U) or the formula 2).

(1-7) (1-8) 161707.doc • 14- 201235784

(1-10)

(1-9) HO3S

Θ S〇3 (1-11)

^so! A

(1-14)

(1-15)

C12H25 (1-16)

(Bu 17) 161707.doc •15· 201235784

(1-22) (1-21)

Λ (1-23)

Η

161707.doc -16- 201235784

The dye preferably contains a compound represented by the formula (3) (hereinafter sometimes referred to as "compound (3)"). The 5 (3) can also be a tautomeric isomer. The content of the compound (3) in the ^ f P hawmin dye of the compound (3) is preferably 50% by mass or more, and the amount of the scale is 70% by mass or more, and more preferably 90% by mass. /. the above. ?31 浐

JyS〇3e (3) [In the formula (3), R and R each independently represent an alkyl group having a carbon number of ^. π and R34 independently of each other represent an alkyl group having a carbon number of 44, a calcined base of carbon number, or an alkylsulfonyl group having a carbon number of 丨4. And r33 may also form a ring containing an atom, and R32 and R34 may together form a ring containing a nitrogen atom. P and q independently represent the integers of 〇~5, as in ? In the case of 2 or more, a plurality of R33s may be the same or different. When 9 is 2 or more, a plurality of R34s may be the same or different; I6J707.doc -17- 201235784 As the alkyl group having a carbon number of 0 and R32, a methyl group, an ethyl group, a propyl group, a butyl group, an isopropyl group, an isobutyl group, a second butyl group, and a third group are exemplified. Butyl 'hexyl' 2-ethylhexyl, decyl, decyl and the like. Examples of the alkyl group having 1 to 4 carbon atoms of R33 and R34 include those having a carbon number of up to 4. Examples of the alkylthio group having 1 to 4 carbon atoms of R33 and R34 include a mercaptothio group 'ethylthio group, a propylthio group, a butylthio group and an isopropylthio group. Examples of the alkyl group having a carbon number of 1 to 4 of R and R include a fluorenyl group, an ethyl group, a propyl group, a butyl group, and an isopropyl sulfonyl group. Preferably, R" and R32 are independently methyl, ethyl, propyl or isopropyl. R33 and R34 are preferably a carbon number of 4, more preferably a methyl group. Preferably, p and q are mutually Independently, it is an integer of 〇~2, and more preferably 丨 or 2. As the compound (7)', for example, the formula ("Μ"~ ((113)) is represented by the formula: In view of the fact that the solubility in the organic solvent is excellent, L' is preferably a compound represented by the formula (1·31) to the formula (1_4G).

161707.doc 201235784

16l707.doc •19- 201235784 As an anthraquinone dye, commercially available 咄Λ·························································································· The "Rh-in" manufactured by Chemical Industry Co., Ltd. can also be used as a starting material in the commercially available (4) dyes, and can be synthesized by referring to the Japanese Patent Publication No. 2〇1〇_32999. The coloring agent (4) can also be used. Containing a dye different from the cap material. As such =, for example, an azo dye, a metal mis-salt azo dye, a scallion, a benzotriene dye, a cyanine dye, a naphthalene dye, a brewing imine dye, Amethyst dye, squaric acid dye and phthalocyanine dye. Colorant (8) can be selected according to the color of the desired color filter. A plurality of the above dyes and pigments can also be used in combination. Colorant (4) "Mountain, Star The content of the dye is preferably from 1 to 80% by mass, more preferably from 3 to 5% by mass, still more preferably from 3 to 35% by mass, based on the total amount of the coloring agent (VIII). The content of the pigment is relative to the coloring agent (a) ) preferably 2〇~99 mass 0/., It is preferably 50 to 97% by mass, and more preferably 65 to 97% by mass. If the content of the heart dye and the pigment is within the above range, a color filter excellent in heat resistance and color performance can be obtained. The content of the (A) is preferably from 5 to 60% by mass, more preferably from 8 to 55% by mass, even more preferably from 10 to 50% by mass, based on the solid content of the colored photosensitive resin composition of the present invention. When the content of the coloring agent (A) is within the above range, the color density when the color filter is formed is sufficient, and the necessary amount of the resin can be contained in the composition, so that the tendency to form a pattern having sufficient mechanical strength is obtained. Preferably, the solid content means that the solvent is removed from the total amount of the colored photosensitive resin composition of the present invention to obtain an amount of I61707.doc -20-201235784 201235784. The colored photosensitive resin composition of the present invention may contain a resin resin (8) by the liquid chromatography or the amount of each component, and a known analytical method such as gas chromatography. (4) Limited, preferably Soluble resin. # As a tree Θ (Β), for example, the following resins [Κ1ΗΚ4] and the like are exemplified. [Κ1] A monomer having a cyclic oxime structure of 2 to 4 and an ethylenically unsaturated bond (4) (hereinafter) At the time, it is called "(4)"), and at least one type (b) (hereinafter sometimes referred to as "(8)") which is selected from the group consisting of unsaturated acid-lowering acid and unsaturated acid-reducing needles [K2] (a And (8) and a copolymer which can be copolymerized with (a) a monomer (4) (other than (4) and (8)) (hereinafter sometimes referred to as "(c)"). [K3] (b) and (c) Copolymer [K4] A resin obtained by reacting the copolymer of (b) and (c) with (a). [K5] A resin obtained by reacting the copolymer of (a) and (c) with (b). [K6] A resin obtained by reacting the copolymer of (a) and (c) with (b) and further reacting with phthalic anhydride, (a) is, for example, a cyclic ether structure having a carbon number of 2 to 4 ( For example, a polymerizable compound selected from the group consisting of at least one of an oxirane ring, an oxetan ring and a tetrahydrofuran ring, and an ethylenically unsaturated bond. Preferably, (a) is a monomer having a cyclic ether having 2 to 4 carbon atoms and a (fluorenyl) acryloxy group. In the present specification, the term "(fluorenyl)acrylic acid" means at least one selected from the group consisting of acrylic acid and mercaptoacrylic acid. The notation such as "(meth) propyl thiol" and "(meth) acrylate" has the same meaning. 161707.doc 201235784 (a), for example, a monomer (al) having an oxirane group and an ethylenically unsaturated bond (hereinafter sometimes referred to as r(al)"), having an oxetanyl group And a monomer having an ethylenically unsaturated bond (a2) (hereinafter sometimes referred to as "(a2)"), a monomer having a tetrahydrofuranyl group and an ethylenically unsaturated bond may be referred to as "(4))" )Wait. (al) ', for example, a monomer (al-1) having a structure in which a linear or branched aliphatic unsaturated smoke is epoxidized and an ethylenically unsaturated bond (hereinafter sometimes referred to as r) (a 1 ·]))), and a monomer (al_2) having a structure in which an alicyclic unsaturated hydrocarbon is epoxidized and an ethylenically unsaturated bond (hereinafter sometimes referred to as "(al-2)") . Examples of (al-Ι)' include glycidyl (meth)acrylate, β-methylglycidyl (meth)acrylate, p-ethylglycidyl (meth)acrylate, and glycidyl vinyl ether. , o-vinylbenzyl glycidyl ether, m-vinylbenzyl glycidyl ether, p-vinylbenzyl glycidyl ether, cardiomethyl-o-vinylbenzyl glycidyl ether, α-methyl-m-vinyl benzyl ether Glycidyl ether α-methyl-p-ethylene benzyl glycidyl ether, 2,3-bis(glycidoxymethyl)styrene, 2,4·bis(glycidoxymethyl)benzene Dilute 2'5-bis(glycidoxymethyl)styrene, 2,6-bis(glycidoxymethyl)styrene, 2,3,4-tris(glycidoxymethyl)benzene Ethylene, 2'3'5·tris(glycidoxymethyl)styrene, 2,3,6-tris(glycidoxycarbonyl), stupid ethylene, 3,4,5·3 (shrinkage) Glyceroxymethyl) styrene, 2,4,6-di(glycidoxymethyl)styrene, and the like. As (al-2), there may be mentioned: acetylcyclohexanone monooxide, ^-epoxy-4-vinylcyclohexane (for example, CelI〇xide 2〇〇〇, Daicel Chemicals = 161707.doc •22·201235784 (manufactured by Co., Ltd.), 3,4-epoxycyclohexyl decyl (meth)acrylate (for example, CyClomer A400, manufactured by Daicel Chemical Industry Co., Ltd.), M-ring (meth) acrylate Oxycyclohexyl decyl ester (for example, Cyci〇mer M1〇〇, manufactured by Daicel Chemical Industry Co., Ltd.), a compound represented by the formula (1), a compound represented by the formula (II), and the like.

(1) (II) [In the formula (I) and the formula (II), Rf> independently represents a hydrogen atom or an alkyl group having 1 to 4 carbon atoms, and a hydrogen atom contained in the alkyl group may be substituted with a hydroxyl group. X1 and X2 independently represent a single bond, _Re...*_Re_〇_, *_Re_s_, *-Re-NH-.

Re represents a calcined diyl group having a carbon number of 1 to 6. * indicates the key with the key]. Examples of the hospital base having a carbon number of 1 to 4 include an f group, an ethyl 'n-propyl group, an isopropyl group, a n-butyl group, a second butyl group, and a third butyl group. Examples of the hospital group in which a hydrogen atom is substituted by a radical are exemplified by methyl, 1·ethyl, 2-ethyl, propyl, 2-propyl, 3-propyl, and Hydroxy-1-methylethyl, 2•transmethyl, methylethyl, butyl, 2-butyl, 3-hydroxybutyl, 4-hydroxybutyl, and the like. The Ra and Rb' are preferably a hydrogen atom, a methyl group, a methyl group, a 1-hydroxyethyl group or a 2-hydroxyethyl group, and more preferably a hydrogen atom or a methyl group. As the second base of the hospital, there are mentioned: methylene, exoethyl, propylamine 2•two 16J707.doc •23· 201235784 alkyl-1,4-diyl, pentane-1,5-base, propane_1 , 3-diyl, etc. X1Υ 2 ', preferably, a single bond, a methylene group, an ethylidene group, a bond group which does not bond with fluorene, and a *-CH2CH2-〇- group, more preferably a single bond, * _CH2CH2_0 base. The compound represented by the formula (I) is exemplified by the formula (1) (5). Things and so on. Preferably, the compound represented by the formula, the formula (1) 3), the formula (U), the formula (17), the formula (1-9) or the formula (M1) to the formula (115) is more preferably a formula (I_n, formula ^) The compound represented by the formula (1-7), the formula (!·9) or the formula (1-15).

I61707.doc -24- 201235784 The compound represented by the formula (II) may, for example, be a compound represented by the formula (π_15). Preferably, it is a compound represented by the formula, the formula (11_3), the formula (π_5), the formula (11-7), the formula (ΙΙ-9) or the formula (Π-ll) to the formula (π-15). More preferably, it is a compound represented by the formula (ΙΙ-1), the formula (n-7), the formula (ΙΙ-9) or the formula (ΙΙ-15). H2c:ch~ ?H3〇H2C==c- H2C:CH—C—0 H2C=CH—C—〇—ch2 co-c2h, H2C=CH—C~0-C2H4-0 CH3 0 H2C=C-c —o CH3 0 H2C=C—c~o—ch2 CH3 0 H2C==C—C-〇-c2H4

o II Η2〇:ΟΗ"·0—O—C2H4—s i? —c one o-c2h4-o

(Π-15) h2c=c (Π-2) Η2〇:ΟΗC~0—C2H4—N ch3〇., I 11 H;jC=0—C—O_C2H4—S CH30 I II h2c=c—co -c2h4- η20=Π-0 ch2oh 0 I 11 h2c=cc—0 c2h4oh o —co

The compound represented by the formula (1) and the compound represented by the formula (II) can be used singly. Also, these can be mixed in any ratio. In the case of mixing, the mixing ratio is in molar ratio, and the formula (1): formula (11) is preferably 5:95 to 95:5, more preferably 10:90 to 90:10, and particularly preferably 20:80~80:20. 16l707.doc -25· 201235784 The monomer (a2) having an oxetanyl group and an ethylenically unsaturated bond is more preferably a monomer having a xanthene butyl group and a (meth) acryloxy group. (10) can be exemplified by: 3-methyl- 3 - mercapto propylene fluorenyloxy oxetane: 3-mercapto-3-propenyloxymethyl oxetane, Hong B: oxime Methyloxetane, 3·ethyl_3_acryloxymethyloxetane, 3-methyl·3_mercaptopropenyloxyethyloxetane,甲基Methyl-3-propenyloxyethyloxetane, 3-ethyl-mercaptopropenyloxyethyloxetane,3·ethyl_3·acryloxyethyl Oxetane and the like. The monomer (a3) having a tetrahydrofuranyl group and an ethylenically unsaturated bond is more preferably a monomer having a tetrahydrofuranyl group and a (fluorenyl)acryloxy group. Specific examples of (a3) include tetrahydrofurfuryl acrylate (for example, Viscoat V# 150, manufactured by Osaka Organic Chemical Co., Ltd.), and tetrahydrofurfuryl methacrylate. (a) ' is preferably (al) from the viewpoint of higher reliability such as heat resistance and chemical resistance of the obtained color filter. Further, from the viewpoint of excellent storage stability of the colored photosensitive resin composition, (a 1 - 2 ) is more preferable. Specific examples of (b) include, for example, acrylic acid, methacrylic acid, butyric acid, o-bromobenzoic acid, m-phenylbenzoic acid, and ethylidenebenzoic acid. Carboxylic acid; maleic acid, fumaric acid, citraconic acid, mesaconic acid, itaconic acid '3-vinylphthalic acid, 4-vinylphthalic acid, 3,4,5 ,6-tetraqiphthalic acid, 1,2,3,6-tetrahydrophthalic acid, dimercaptotetrahydroortylene 161707.doc -26- 201235784 dicapric acid, 1,4-ring Unsaturated ditoxaic acid such as hexene dicapric acid; 5-decalin-2,3-didecanoate, 5-carboxybicyclo[2 21]hept-2-ene, 5,6-dicarboxybicyclo[ 2.2.1] hept-2-ene, 5-carboxy-5-fluorenylbicyclo[2.2.1]hept-2-ene, 5-carboxy-5-ethylbicyclo[221]hept-2-ene, 5_ a bicyclic unsaturated compound containing a buffer group such as a carboxyl group of 6-fluorenylbicyclo[2.2.1]hept-2-ene or 5-carboxy-6-ethylbicyclo[2·2.1]hept-2-ene; Adipic anhydride, tococanic anhydride, itaconic anhydride, 3-vinylphthalic anhydride, 4-vinylphthalic anhydride, 3,4,5,6-tetrahydrophthalic acid needle, 1, 2,3,6-tetrahydroortylene An unsaturated dicarboxylic acid anhydride such as an acid anhydride, dimercaptotetrahydrophthalic anhydride or 5,6-dicarboxybicyclo[2.2.1]heptan-2-ene anhydride; succinic acid mono [2-(methyl)] Unsaturated mono[(methyl) propylene oxime of a polyvalent carboxylic acid having two or more valences such as propylene methoxyethyl ester and phthalic acid mono [2-(indenyl) propylene oxyethyl] ester; An alkyl group] ester; and an unsaturated acrylate having a hydroxyl group and a carboxyl group in the same molecule as the α-(hydroxymethyl)acrylate. Among the above, from the viewpoint of the copolymerization reactivity or the solubility of the obtained resin to the alkali/liquid/liquid mixture, acrylic acid, methacrylic acid, maleic anhydride or the like is preferable. Examples of (c) include (fluorenyl)acrylic acid, (fluorenyl)acrylonitrile, n-butyl (meth)acrylate, and dibutyl (meth)acrylate, (methyl). Acetic acid third butyl vinegar, (methyl) acrylic acid 2-ethylhexyl vinegar, (methyl) acrylic acid dodecapine S|, (mercapto) acrylic acid Laurel S, (mercapto) C Stearyl phthalate, cyclopentyl (meth)acrylate, cyclohexyl (meth)acrylate, 2-nonylcyclohexyl acrylate, (meth)acrylic acid Cyclo [5·21 〇 2 6] decane-8-yl ester (referred to in the art as a customary name (diyl) dicyclopentanyl acrylate), (fluorenyl) biscyclopentyloxyethyl acrylate (indenyl) acrylic acid bicyclo [5.2.1 · 02'6] decene-8-yl ester (referred to in the technical field as (fluorenyl) dicyclopentenyl acrylate) , (meth) isopropyl isopropionate, (amyl) adamantyl acrylate, allyl (meth) acrylate, propargyl (meth) acrylate, phenyl (meth) acrylate, (meth) acrylates such as naphthyl acrylate, benzyl (meth) acrylate, 2-hydroxyethyl (meth) acrylate, 2-hydroxypropyl (meth) acrylate, etc. Acrylates; dicarboxylic acid diesters such as diethyl maleate, diethyl fumarate, diethyl itaconate; bicyclo [2.2.1] hept-2-ene, 5 - indenylbicyclo[2 2 heptyl-2-ene, 5•ethylbicyclo[2.2.1]hept-2-ene, 5-hydroxybicyclo[2.21]hept-2-ene, 5-hydroxymethylbicyclo[2.2 .1]hept-2-ene, 5-(2'-ethyl)bicyclo[2 2"]hept-2-ene, % methoxybicyclo[2.2.1]hept-2-ene' 5_B Oxybicyclo[22丨]hept-2-ene, 5,6-dihydroxybicycloalken, 5,6•bis(hydroxyindenyl)bicyclo[22 hept-2-ene, 5,6-di(2'- Hydroxyethyl)bicyclo[221]hept-2-ene, 5,6•dimethoxybicyclo[2.2.1]hept-2-ene, 5,6-diethoxybicyclo[2.21]hept-2· Alkene, 5-hydroxy-5.methylbicycloalkenene, 5-hydroxy-5-ethylbicyclo[2.2.1]hept-2-diene, 5-methyl-5-methylbicyclo[221]hept_2 _ene, 5_ first butoxycarbonylbicyclo[2.2.1]hept-2-ene, 5-cyclohexyloxycarbonylbicyclo[2.2·1]hept-2-ene 5-phenoxycarbonylbicyclo[2.2.1]hept-2-ene, 5,6-bis(t-butoxycarbonyl)bicyclo[2.2·!]hept-2-ene, 5,6-bis (cyclic Hexyloxycarbonyl 161707.doc •28·201235784 base) bicyclo[2.2.1]hept-2-ene and other bicyclic unsaturated compounds; N-phenyl maleimide, N-cyclohexylpentene Dimethyleneimine, N-n-butylsuccinimide, N-butylenedimino-3-butylbutenylene benzoate, N-butanediamine-4- Maleic acid imide butyl phthalate N-butyl ketone imine-6-m-butylene hexanoic acid hexanoic acid vinegar, N-butyl diimide imino-3-butylene Dicarbonyl quinone imine derivatives such as amine propionate, Ν_(9. acridinyl) maleimide, styrene, α-methyl styrene, m-methyl styrene, p-methyl benzene Ethylene, vinyl toluene, p-methoxystyrene, acrylonitrile, methacrylonitrile, vinyl chloride, vinylidene chloride, acrylamide, methacrylamide, vinyl acetate, 1,3-butadiene , isoprene and 2,3-dimethyl-oxime, 3-butadiene, and the like. In the viewpoint of copolymerization reactivity and heat resistance, it is preferably styrene, vinyl toluene, phenyl butyl succinimide, Μ·cyclohexyl cis-butane dioxime. Imine, Ν•节基顺丁晞晞iimine, bicyclo [2.2.1] hept-2-thene, etc. In Yu Shuzhi [κι], the ratio of the structural unit of each source to the total structural unit constituting the resin [κ丨] is preferably in the following range. From the structural unit of (a) '5〇~98 mol% (more preferably (9) ~ (10) Moer (6) from the structural unit of (b), 2~5G mol% (more preferably 丨(四)莫耳. If resin When the ratio of the structural unit of [K1] is within the above range, the storage stability, the developability, and the solvent resistance of the color filter of the colored photosensitive resin are preferably good. Resin [Κ1] For example, you can read _ #士占,Γ 参考 "Research method for polymer synthesis" 16l707.doc -29· 201235784 (Otsu Takayuki, 'issuing company, chemical co-owner, first edition, first print, In the method described in the above-mentioned publication, the method described in the above-mentioned document, and the reference to the literature, the production of β, specifically, the specific amount of (a) and (15), a polymerization initiator, a solvent, etc. In the reaction vessel, for example, a method of heating and holding the oxygen in a deoxidizing atmosphere by a nitrogen gas is formed by stirring, and the polymerization initiator, the solvent, and the like used herein are not particularly limited, and any of them may be used. User in the field. As a polymerization initiator For example, an azo compound (2,2,-azobisisobutyronitrile, 2,2, azobis(2,4-dimethylvaleronitrile), etc.) or an organic peroxide (benzoate) As the solvent, ruthenium or the like can be used as the solvent (E) of the colored photosensitive resin composition of the present invention, as long as it can dissolve each monomer. Further, the copolymer obtained in (4) can be directly used. As the solution after the reaction, a concentrated or diluted solution may be used, or a method of extracting in the form of a solid (powder) by reprecipitation or the like may be used. In particular, at the time of the polymerization, the present invention is used. The solvent contained in the colored photosensitive resin composition is used as a solvent, and the colored photosensitive resin composition of the present invention can be directly used as the solution after the reaction. Thus, the coloring photosensitive resin composition of the present invention can be easily formed. In the resin [K2], the ratio of the structural unit of each source to the total structural unit constituting the resin (10) is preferably in the following range. " Structural unit derived from (a), 2 to 95 mol% (more preferably 5) ~8〇莫耳from the structural unit of (b) ' 4 45% by mole (more preferably 丨q~Μ莫耳called the structural unit from (c), 丨~65mol% (more preferably 5~6〇%) 161707.doc 30· 201235784 If resin [ When the ratio of the κ structural unit is the above-mentioned criterion (4), the storage stability and developability of the colored photosensitive resin composition, and the solvent resistance, heat resistance and mechanical strength of the color filter tend to be good. Κ2] can be produced, for example, in the same manner as described for the production method of the resin. Specifically, a specific amount of (4), (b), and (4), a polymerization initiator, and a solvent are introduced into the reaction container towel. For example, (4) a method in which nitrogen is replaced with oxygen and the shape of the oxygen is deoxidized, thereby heating and keeping warm while stirring. The obtained copolymer may be directly used as a solution after the reaction, or may be a cold liquid which is diluted or diluted, or may be extracted as a solid (powder) by a method such as re-sinking. In the resin (4), the ratio of the structural unit of each source to the total structural unit constituting the resin is preferably in the following range. 0) 2 to 50 mol%, more preferably 5 to 4 〇 mol% (c) 5 0 to 98 mol% 'better than 6 〇 to 95 mol% Resin [K3] can be used as a resin, for example [ The manufacturing method of Kl] is produced in the same manner as described. The resin [Κ4] can be obtained by obtaining a copolymer of sand and (〇), and (a) having a cyclic ether having 2 to 4 carbon atoms and (b) having a carboxyl group or a carboxylic anhydride; First, the copolymer of (8) and (4) is produced in the same manner as described in the production method of [K1]. In this case, the structural unit derived from cerium is copolymerized in the structures (b) and (c). The ratio in the total structural unit of the substance is preferably in the following range. 161707.doc 31 201235784 (b) 5 to 50 moles/〇, more preferably 10 to 45 moles (C) 50 to 95 moles /β, more preferably 55 to 90 mol%, which is - a human 'the part of the copolymer derived from the structural unit derived from (b) and/or the portion of the hydrocarbon anhydride and the carbon number of (4) The ring bond of 4 is reacted. After the copolymer of (b) and (e) is produced, the environment in the flask is replaced with air from nitrogen, and the reaction catalyst of (4), carboxyl group and cyclic ether is put into the flask. For example, it is 6 〇 to 130. (: The reaction is carried out for 1 hour, whereby the resin [K4] is obtained. As the above reaction catalyst, for example, tris(dimethylamino) can be cited. The amount of the above-mentioned reaction catalyst is 0 to 5% by mass based on the total amount of the catalysts of (4) to (4). Examples of the polymerization inhibitor include p-phenylene phenol and the like. The amount of use relative to the total amount of (a) to (c) is preferably 0. _ to 5 mass%. The method of loading, the reaction temperature, and the reaction conditions of the material can be appropriately adjusted in consideration of the manufacturing equipment or the polymerization enthalpy (4). In the same manner as the polymerization conditions, the charging method or the reaction temperature may be appropriately adjusted in consideration of the heat generated by the production equipment or the polymerization, etc. The amount of use of (4) is preferably (b) 1 mol, preferably 5 to 8 〇 Mo Er, more preferably H) 〜 75 摩尔, and particularly preferably 15 to 7 〇 Mo. By setting it as the range, there is storage stability and developability of the I color photosensitive resin composition. And the sensitivity of the sensitivity and the heat resistance and the mechanical strength of the color-sensitive film are improved. The resin [K5] is the first stage in the same manner as the above-mentioned method of producing the resin [κυ]. A copolymer of (a) and (c) is obtained. The same as above, obtained The polymer may be directly used as a solution after the reaction, or a solution diluted or diluted by 161707.doc -32-201235784 may be used. It may also be extracted as a solid (powder) by reprecipitation or the like. Preferably, the ratio of the structural units from (4) and (4) to the total number of moles of the total structure of the above-mentioned copolymers 7C is the following range. The structural unit derived from (a) is 5 to 95% by mole ( More preferably, it is 1〇~9〇mol%). The structural unit derived from (c), 5 to 95% by mole (more preferably 1〇~9〇% by mole) Further, it can be manufactured with resin [K4] Under the same conditions, the copolymer of (a) and (c) has a cyclic ether derived from (a) and (b) a carboxylic acid or a carboxylic anhydride, thereby obtaining a resin [艮5] ]. The amount of (b) used for the reaction with the above copolymer is preferably from 5 to 80 moles per mol of (a). In view of the fact that the cyclic ether is highly reactive and does not easily remain unreacted (a), it is preferably (al), more preferably (al-1), used as the resin [K5]. The resin [K6] is a resin formed by reacting a citrate liver with a resin [K5]. The reaction group produced by the reaction of a cyclic acid or a slow acid acid is reacted with a carboxylic acid anhydride. As the acid-reducing if ’, there may be mentioned cis-butyl succinate, citraconic acid, and itaconic acid. -ethylene phthalic acid, 4_ethyl phthalic phthalic anhydride, M, 5,6-tetrahydrophthalic anhydride, 3,6-tetrahydrophthalic acid, dimethyl Tetrahydrophthalic acid, 5'6-dimercaptobicyclo[2 2 ·]]heptanoic anhydride, and the like. As the resin (B) 'specific cyclohexyl methyl ester / (methyl) C, (meth)acrylic acid 3,4•epoxy enoic acid copolymer, acrylic 3,4-epoxy tricyclic 16f707.doc •33· 201235784 [5.2.1.02 6]Resin such as oxime ester/(meth)acrylic acid copolymer [K1]; (meth) glycidyl acrylate / benzyl (meth) acrylate / (meth) acrylate copolymer , (fluorenyl) glycidyl acrylate / styrene / (mercapto) acrylic copolymer, 3,4-cyclopyrene tricyclo[3.2.1.02.6] oxime ester / (fluorenyl) acrylic acid / N_ ring Hexyl cis-butyl diimide copolymer, 3,4-epoxytricyclo[5.2.1.02 6]decyl acrylate / (meth) acrylate / vinyl toluene copolymer, 3 曱 _ 3- (A Resin such as fluorenylmethyl oxetane/(mercapto)acrylic acid/styrene copolymer [K2]; benzyl (meth) acrylate/(meth) acrylate copolymer, a resin such as a styrene/(meth)acrylic copolymer [K3]; a resin obtained by adding a (benzyl) methacrylate/(meth)acrylic copolymer and a glycidyl (mercapto)acrylate to form a resin. (Methacrylate A resin formed by addition of a tricyclodecyl ester/styrene/(meth)acrylic acid copolymer and glycidyl (meth)acrylate to give tricyclode(meth)acrylate/benzyl (meth)acrylate a resin such as a resin formed by addition of a /(meth)acrylic acid copolymer and glycidyl (meth)acrylate [Κ4]; copolymerization of dicyclopentanyl (meth)acrylate/glycidyl (meth)acrylate a resin formed by reacting a substance with (meth)acrylic acid, and a resin such as a resin obtained by reacting a copolymer of dicyclopentyl (meth)acrylate/glycidylmethyl methacrylate with (meth)acrylic acid [Κ5]; a resin formed by reacting a copolymer of dicyclopentyl (meth)acrylate/glycidyl (meth)acrylate with (meth)acrylic acid and further reacting with tetrahydrophthalic anhydride Resin such as resin [Κ6]. Among them, a resin [Κ1] and a resin [κ2] are preferable, and a resin [Κ1] is more preferable, and a 3,4-epoxytricyclo[5.2 1 Μ' oxime/(meth)acrylic acid copolymer is further preferred. Things. If the resin (Β) contains the structure of the structure I61707.doc -34 - 201235784 from (a), the reliability of the heat resistance and chemical resistance of the obtained color filter can be further improved. The weight average molecular weight of the resin (B) in terms of polystyrene is preferably 3,000 to 100, more preferably 5, 〇〇〇 50, 〇〇〇, and further preferably 5 〇〇〇 to 35, 〇 Hey, especially good for 6, _,, just, especially good for 7, _~28, _. When the molecular weight is in the above range, the coating film hardness is improved, and the residual film ratio is also high, and the solubility of the unexposed portion in the developer is good, and the resolution tends to be improved. The molecular weight distribution [weight average molecular weight (Mw) / number average molecular weight (?η)] of the resin (B) is preferably L1 to 6, more preferably 〖2 + the acid value of the tree (B) is preferably 5 〇 15G mg K〇H/g is more preferably ~(1) mg-K〇H/g' and further preferably 7〇~135mg_K〇H/g. Here, the acid value is neutralized! The value measured by the amount of gas oxidative removal required for the resin (4) can be determined, for example, by enthalpy of the (iv) hydroxide solution. The content of the resin (B) is preferably 7 to 65 mass%, more preferably 3 to 6 mass%, still more preferably 17 to 55 mass, based on the solid content of the colored photosensitive resin composition of the present invention. %. When the content of the resin (8) is in the above range, the colored pattern ’ can be formed, and the resolution and the residual film ratio tend to be improved. The color photosensitive resin composition of the present invention contains a polymerizable compound: the dimerizable compound (C) is a compound which can be polymerized by an active radical derived from a polymerization initiator (9), an acid or the like, for example, can be classified. And the like, the first two: the polymerizable compound (C), preferably having three or more ethyl hydrazides in the unsaturated bond. Examples of such a polymerizable compound include, for example, Quarter I61707.doc -35 - 201235784 Pentaerythritol Tetramethyl (meth)acrylate Dipentaerythritol Penta(methyl)acrylate, Dipentaerythritol Hexa(propyl)propyl Dilute ester, tripentaerythritol octa (meth) acrylate, tripentaerythritol hepta (meth) acrylate, pentaerythritol deca (meth) acrylate, pentaerythritol 九 (meth) acrylate, isocyanuric acid three (2 -(Methyl)acryloxyethyl)g, ethylene glycol modified pentaerythritol tetra(meth)acrylate, ethylene glycol modified dipentaerythritol hexa(methyl) acrylate, propylene glycol modified pentaerythritol Tetrakis(yl) acrylate, propylene glycol modified dipentaerythritol hexa(meth) acrylate, caprolactone modified pentaerythritol tetra(meth) acrylate, and caprolactone modified dipentaerythritol hexa(meth) acrylate vinegar . Among them, dipentaerythritol penta (meth) acrylate, dipentaerythritol hexakisyl acrylate, and the like are preferable. The polymerizable compound may be used singly or in combination of two or more. The weight average molecular weight of the polymerizable compound (C) is preferably io 5 Å or more and 2,900 or less, more preferably 250 Å or less. The content of the polymerizable compound (C) is preferably 7 to 65 mass%, more preferably 13 to 60 mass%, and further preferably 17 to 55 mass, based on the solid content of the coloring photosensitive resin composition of the present invention. %. When the content of the polymerizable compound (C) is within the above range, the curing is sufficiently performed, the residual film ratio during development is improved, and undercut is less likely to occur in the colored pattern, and the adhesion tends to be good. . The colored photosensitive resin composition of the present invention contains a polymerization initiator (D). The polymerization initiator (D) is not particularly limited as long as it is a compound capable of generating a living radical, an acid or the like by the action of light or heat, and a known polymerization initiator can be used. 16l707.doc •36- 201235784 As the polymerization initiator (D) 'It is preferred to generate active radicals by the action of light, more preferably an alkyl ketone compound, a tri-nized compound, a fluorenyl phosphine oxide compound, The hydrazine compound and the biimidazole compound are further preferably an anthracene compound. The above alkylphenone compound is a compound having a partial structure represented by the formula (d2) or a partial structure represented by the formula (d3). In these partial structures, the benzene ring may have a substituent.

4 is a compound having a partial structure represented by the formula (d2), and, for example, '2-mercapto-2-morpholinyl-fluorene-methyl thiophenyl)propane oxime ketone, 2-dimethyl dimethyl ketone Amino-1-(4-morpholinylphenyl)-2-benzylbutane-indoleone and 2-(diamino)-2-[(4-indolylphenyl)indenyl] Polinyl) phenyl] butyl saponin and the like. Commercial products such as Irgacure (registered trademark) 369, 907, and 3-9 (manufactured by BASF Corporation) can also be used. Examples of the compound having a partial structure represented by the formula (d3) include 2-hydroxy-2-mercapto-1-indolyl propane ketone, 2-hydroxy-2-indolyl-indole-? (2-hydroxyethoxy)phenyl]propane oxime ketone, hydrazine-hydroxycyclohexyl phenyl ketone, 2-hydroxy-2-mercapto-1-(4-isopropenylphenyl)propane 丨Olefin oligomers, gastric diacetyl acetophenone and benzoic dinonyl ketals. From the viewpoint of sensitivity, as the alkylphenone compound, a compound having a partial structure represented by the formula (d2) is preferred, and more preferably a quinolylmorpholin-1-(4-methylsulfide). Phenyl phenyl) propane _ 丨 ketone and 2 dioxin 丨 I I61707.doc • 37· 201235784 phenyl phenyl)-2-pyrylbutane-1-one. Examples of the above-mentioned three-till compound include 2,4-bis(trimethylmethyl)_6_(4·decyloxyphenyl)-1,3,5-three tillage, and 2,4·bis(trichloroindenyl). )-6-(4-decyloxynaphthyl)-1,3,5-di-11, 2,4-bis(trimethylmethyl)-6-to-caiji_1,3,5-three Tillage, 2,4·bis(trimethylmethyl)-6-(4-methoxystyryl)_i, 3,5•three, well, 2,4-bis(trimethyl)methyl-6-[ 2-(5-methylfuran-2-yl)vinyl]_ι,3,5·三井' 2,4-bis(dioxamethyl)_6-[2-(.f.nan-2-yl) Ethyl]_ι,3,5·three tillage, 2,4-bis(trichloromethyl)-6-[2-(4-diethylamino-2-methylphenyl)vinyl]-1 '3,5-three tillage, 2,4-bis(trimethyl)-6-[2-(3,4-dimethoxyphenyl)vinyl]-1,3,5-three tillage, etc. . The above fluorenylphosphine oxide compound may, for example, be 2,4,6-trimethylbenzylidenediphenylphosphine oxide. Commercial products such as Irgacure (registered trademark) 819 (manufactured by BASF Corporation) can also be used. The above compound is a compound having a partial structure represented by the formula (d 1). Hereinafter, * indicates a keying key.

Examples of the above hydrazine compound include N-benzoquinoneoxy-hydrazine-(4-phenylthiol basic) butyl-1-keto-2-imine, N-benzoquinone-1-( 4-phenylthiophenyl)octane-1-one-2-imine, N-benzylideneoxy-1-(4-phenylthiophenyl)-3-cyclopentylpropane-1 Ketone-2-imine, N-acetoxy-i-[9-ethyl-6-(2-methylphenylhydrazone)·9Η-flavor. -3-K]B--1-imine, N-acetoxyethyl·6-{2-methyl-4-(3,3-dimercapto-2,4-di) Cyclopentyl 161707.doc • 38 · 201235784 oxy)benzimidyl 9H-carbazol-3-yl]ethane-1-imine, N-ethoxycarbonyl. N[9-ethyl- 6-(2-methylbenzylidenyl)-9Η·oxazol-3-yl]-3-cyclopentylpropane-1-imine, Ν-benzylideneoxy 4_[9_ethyl_6_ (2-Methylbenzylidene)_9Η-carbazolyl]_3_cyclopentylpropane_丨-ketone-2-imine. Commercial products such as IrgaCUre (registered trademark) 〇ΧΕ01, 〇ΧΕ02 (manufactured by BASF Corporation), and N-1919 (made by ADEKA Co., Ltd.) can be used. In the case where the colored photosensitive resin composition of the present invention is a blue colored photosensitive resin composition, since the brightness of the obtained color filter becomes high, it is preferred to use a material selected from N-Benyl. Oxyl (4) phenylthiophenyl) butyl ketimine, N-benzylideneoxy-1-(4-phenylthiophenyl)octane oxime ketone 2-imine and N_benzhydryloxy_丨_(4_phenylthiophenyl•cyclopentylpropanol 1鲷2-imine group of at least one species of the above-mentioned car compound. As the biimidazole compound, a :2,2,_bis(2_chlorophenyl::4',5,5'-tetraphenylbiimidazole, 2,2ι·bis(2,3-diphenyl)-4,4|, 5,5,-tetraphenyl-based taste. Sitting (for example, see Japanese Patent Laid-Open No. Hei 6-75372, Japanese Patent Application Laid-Open No. Hei No. Hei 6-75373, etc.), 2, 2ι_double (2_gasphenyl)_4,4 ',5,5|-Tetraphenyl hydrazine, 2,2,·bis(2- phenyl)-4,4|,5,5,_tetra(indolyloxyphenyl)biimidazole, 2 , 21_bis(2_chlorophenyl)·4,4ι,5,5,_tetrakis(dialkyloxy$phenyl)-linked oxazole, 2,2, bis(2-chlorophenyl)_4,4, ,5,5ι_tetrakis Benzene) 联米坐 (for example, 'refer to Japanese Patent Special Publication No. 48_384 () No. 3, Japanese Patent Laid-Open No. 74204, etc.), 4, 4, 5, 5, _ position of phenyl by the hospital oxygen The m-substituted ruthenium compound (for example, refer to Japanese Patent Laid-Open No. Hei. No. 913), etc., etc., preferably, bis(2-phenylphenyl)-MW.tetraphenylene is exemplified. , 2, 2, bis(2,3-dichlorophenyl)·161707.doc -39- 201235784, 2,2'·double (2,4-two gas base)_4,4,,5,5, _4,4',5,5'-tetraphenylbiimidazolium phenyl carbene. Sit.:: as a polymerization initiator (9), which can be enumerated: benzoin, benzoin, scent, scent, scent, scent Isoproterenol, benzoin, etc., benzoin, etc., 'diphenylene _, o-benzoylbenzoic acid, A, 4 phenyl dibenzophenone, benzoyl ketone, methyl diphenyl sulfide, 3, Dibenzophenones such as 3,4,4,_tetra (p.: butylperoxycarbonyl) dimercapto ketone, 2,4,6•trimethyldibenzophenone, 9'10-phenanthrene醌, 2_ethyl hydrazine, camphor quinone and other hydrazine compounds; 10-butyl 2 - gas. 丫 phase, benzoin oxime, ethoxylated acid, gluten vinegar, dioxin Preferably, these are used in combination with the following polymerization initiation assistant (D1) (especially guanamine). As the acid generator which generates an acid by light, for example, 4-hydroxyphenyl group is exemplified. Methyl (tetra) toluene salt, 4 _ phenyl dimethyl sulfonium hexahydrate, 4 ethoxylated phenyl diphenyl sulfonium p-toluate, ethoxylated benzyl-methyl-benzyl fluorene Fluoride, triphenylsulfonium sulfonate, triphenylsulfonium hexafluoroate, diphenylphosphonium toluene salt, diphenylphosphonium hexafluoroantimonate, etc., or Nitro-succinyl tosylate, and benzoin tosylate. The content of the polymerization initiator (D) is preferably 0.1 part by mass, more preferably 0 parts by mass, based on 100 parts by mass of the total of the resin (B) and the polymerizable compound (c). When the content of the initiator is within the above range, the sensitivity is improved and the exposure time is shortened to improve productivity. The colored photosensitive resin composition of the present invention may further contain a polymerization initiation aid (D1). The agent (D1) is a compound for promoting polymerization of a polymerizable compound which is polymerized by a polymerization initiator 161707.doc • 40· 201235784, or a sensitizer, usually used in combination with a polymerization initiator (D). Examples of the polymerization initiation aids include an amine compound, a oxy-onion compound, a oxonium sulfonium compound, and a carboxylic acid compound. Examples of the amine compound 'triethanolamine, methyldiethanolamine, and three= Propylamine, methyl 4-diaminoaminobenzoate, ethyl 4-dimethylaminobenzoate, 4-dimethylaminobenzoic acid, isoamyl, 2-diamylamine acetoacetate, 4 -dimethylaminobenzoic acid 2-ethylhexyl, dimethylpara-toluidine, 4,4,_ (Diammonium) benzophenone (commonly known as Michele _), 4,4·-bis(diethylamino)diphenylmethylamine, 4,4,·bis(ethylmethylamino)diphenyl A ketone or the like is preferred, and 4'4-bis(diethylamino)benzophenone is preferred. Commercial products such as eaB-F (manufactured by Hodogaya Chemical Co., Ltd.) can also be used. The compound may, for example, be 9,1 〇dimethoxy oxime, 2 ethane bromide, 10-methoxy oxime, 9,10-diethoxy onion, 2•ethyl·9,1〇_2B. Oxime, 9,1〇-dibutoxyanthracene, 2.ethyl_9,1〇-dibutoxy onion, etc. As the 9-oxosulfonium compound, 2: isopropyl winter Oxime, isopropyl oxalate, mountain, star, 2,4_diethyl_9_oxythioxin, κ dichloro-9-oxopurine, star,;[_氯_4_ Propyloxy-9-oxopurine, etc., as the acid compound, phenylthioacetic acid, methylphenylthioacetic acid, ethylphenylthioacetic acid, mercaptoethylphenylsulfide Acetic acid, two

Methylphenylthioacetic acid, methoxyphenylthioacetic acid 'dimethoxy stupyl I thioacetic acid, chlorophenylthioacetic acid, dichlorophenylthioacetic acid 'cardiamine, phenoxyacetic acid , naphthylthioacetic acid, indole naphthylamine

Acetic acid and the like. I I61707.doc 201235784 The polymerization start (4) can be used alone or in combination of two or more. In the case of using the polymerization initiation aid (D1), the amount of use thereof is preferably 0.1 to 30 parts by mass based on the total amount of the resin (B) and the polymerizable compound (C). More preferably 丨~2〇 parts by mass. In the range of the summer start polymerization aid (D1), it is possible to enter a boat to form a round shape with a sensitivity to improve the productivity of the pattern. The colored photosensitive resin composition of the present invention contains a solvent (8). The solvent (8) is one containing dipropylene glycol monomethyl ether acetate. The content of monopropanol monomethyl ether acetate is preferably 0.1 mass based on the total amount of the solvent (E); t% or more and 30% by mass or less, more preferably hydrazine. /. The above 2% by mass or less, more preferably 2% by mass or more and 15% by mass or less. The solvent (E) may also contain a solvent other than dipropylene glycol monoterpene ether acetate. The solvent is not particularly limited, and a solvent which is usually used in the field can be used. For example, an ester solvent (a solvent containing a &lt;〇〇_ structure in the molecule and not containing a -〇· structure)] an ether solvent (a solvent containing a structure in a molecule and not containing a -COO-structure), an ether Ester solvent (solvent containing _COO-structure and _〇_ structure in the molecule), ketone solvent (solvent containing structure 'in the molecule without _coo_ structure), alcohol solvent (containing OH group in the molecule) It does not contain a structure, a solvent of -C〇·structure and _c〇〇_ structure, an aromatic hydrocarbon solvent, a guanamine solvent, and dimethyl sulfoxide. Examples of the vinegar solvent include: decyl lactate, ethyl lactate, butyl sulphate 2-iso-p-isobutyrate, ethyl acetate, n-butyl acetate, isobutyl acetonate, amyl formate, and acetic acid Amyl ester, butyl propionate, isopropyl butyrate, butyl k ethyl ester, butyl butyrate, methyl pyruvate, ethyl pyruvate, pyruvic acid I61707.doc • 42· 201235784 propyl ester, acetamidine acetate Ester, ethyl acetate, cyclohexanol acetate, γ-butyrolactone, and the like. Examples of the ether solvent include ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, ethylene glycol monopropyl ether, ethylene glycol monobutyl ether, diethylene glycol monoterpene ether, diethylene glycol monoethyl ether, and Ethylene glycol monobutyl ether, propylene glycol monomethyl ether, propylene glycol monoethyl ether, propylene glycol monopropyl ether, propylene glycol monobutyl ether, 3-methoxy-1-butanol, 3-decyloxy-3-mercaptobutyl Alcohol 'tetrahydrofuran, tetrahydrofuran, 1,4-diox' pit, diethylene glycol dimethyl ether, diethylene glycol diethyl ether, diethylene glycol decyl ether, diethylene glycol dipropyl ether, Diethylene glycol dibutyl ether, phenyl ether, phenethyl ether, methylbenzene shunt and so on. Examples of the ether ester solvent include methyl methoxyacetate, methoxyacetic acid, butyl oxyacetate, methyl ethoxyacetate, and ethoxyacetic acid vinegar '3-methoxypropionic acid. Ester ester, ethyl 3-methoxypropionate, decyl 3-ethoxypropionate, ethyl 3-ethoxypropionate, decyl 2-methoxypropionate, 2-nonoxypropionic acid Ethyl propyl 2-methoxypropionate, methyl 2-ethoxypropionate, ethyl 2-ethoxypropionate, methyl 2-methoxy-2-methylpropionate, 2- Ethyl ethoxy-2-mercaptopropionate, 3·methoxybutyl acetate, 33-yl-3-methoxybutane acetate, propylene glycol monoterpene ether acetate, propylene glycol monoethyl ether acetate Ester, propylene glycol monopropylene acetic acid, ethylene glycol monomethyl ether acetate, ethylene glycol monoethyl ether, ethylene glycol monoethyl ether acetate, diethylene glycol monobutyl ether acetate, and the like. As the granule, 4-carbyl-4-methyl-2-pentanone, acetone, 2-butyl-, 2-heptanone, 3-heptanone, 4-heptanone, 4-methyl-2_ Ethyl, cyclopentanone, cyclohexanone, isophora, etc. 161707.doc .43- 201235784 Alcohol, hexanol, methyl benzene, and mesitylene. Examples of the alcohol solvent include decyl alcohol, ethanol, propanol cyclohexanol, ethylene glycol, propylene glycol, and glycerin. Examples of the aromatic hydrocarbon solvent include benzene, methyl benzene, and benzene. Examples of the guanamine solvent 'N n τ 丞 醯 醯 amine, ν, ν-dimethyl ethaneamine, Ν-methyl pirenone, and the like. These solvents may be used alone or in combination of two or more. From the viewpoint of coatability and dryness, it is preferred that the boiling point at (4) quasi-atmospheric pressure (1 atm) is 12 passages or more (10). 〇The right machine/grain below. Among them, preferred is propylene glycol monomethyl saponin 7 in fresh soap f ether acetate, ethyl lactate, lactic acid butyl vinegar, propylene glycol monomethyl (tetra), 3-ethoxypropionic acid ethyl acetonate, ethylene glycol mono sulphur, Diethylene glycol monomethyl (tetra), diethylene glycol monoethyl hydrazine, 4_ylidyl-2-pentanone, hydrazine, hydrazine dimethylformamide, n-methylpyrrolidone, etc., more preferably propylene glycol A-acetic acid series, propylene glycol monomethyl _, lactic acid ethyl acetonate, ethyl ethoxy propionate and the like. Preferably, the solvent (E) contains dipropylene glycol monomethyl ether acetate and ethyl lactate. In this case, the content of the ethyl lactate relative to the total amount of the solvent (E) is preferably 5% by mass or more and 90% by mass or less, more preferably 2% by mass or more and 8% by mass or less, and further preferably 4%. The mass% or more is 7 〇 mass% or less. Further, the solvent (E) is preferably a mixture of three or more kinds of dipropylene glycol monoterpene ether acetate, and more preferably a mixed solvent of four or more. When the solvent (E) is a mixed solvent of three or more kinds of dipropylene glycol monoterpene ether acetate, it is preferred that the solvent (E) contains dipropylene glycol monoterpene ether acetate, ethyl lactate, and propylene glycol. Ether ether and / or propylene glycol monoterpene ether E I61707.doc • 44 · 201235784 Acid vinegar, more preferably contains dipropylene glycol monoacetic acid vinegar, lactic acid ethyl acetate, propylene glycol single test and propylene glycol mono-acetic acid. Further, it is preferable to contain the above, and the dipropylene glycol monoacetic acid vinegar, the lactic acid vinegar, the propylene glycol monomethyst, and the propylene glycol monomethyl acetonitrile, the total content of the G 骎 from the total amount of the solvent (E) The amount is 90% by mass or more, and more preferably 95% by mass or more. In the case where the solvent (6) contains propylene glycol monoterpene, the content thereof is preferably 4% by mass or less, more preferably 5% by mass or more and 30% by mass or less based on the total amount of the solvent (8). In the case where the solvent (Ε) contains propylene glycol mono-f-acetic acid, the content thereof is preferably 7% by mass or more, more preferably 40% by mass or less, more preferably 5% by mass based on the total amount of the solvent (8). /. The above 3〇% by mass or less. When the right solvent (E) is the above solvent, the film produced by drying under reduced pressure is less likely to generate crater defects, and the occurrence of unevenness can be suppressed. The content of the solvent (8) is preferably 70 to 95% by mass, more preferably 5% by mass based on the total mass of the colored photosensitive resin composition of the present invention. In other words, the solid content component of the colored photosensitive resin composition of the present invention is preferably 5:30% by mass or more preferably 8 to 25% by mass. When the content of the solvent (8) is within the above range, the flatness at the time of coating becomes good, and the color density is sufficient when the color light-emitting sheet is formed, so that the display characteristics tend to be good. The colored photosensitive resin composition of the moon may further contain a surfactant (G). Examples of the surfactant (G) include a polyfluorene-based surfactant, a fluorine-based surfactant, and a polyfluorene-based surfactant having a fluorine atom. These may also have a polymerizable group on the branch. . Examples of the polyoxymethylene surfactant include an interface having a decane bond, 161707.doc -45 - 201235784, and the like. Specifically, Toray Silicone (trade name) DC3PA 'Toray Silicone SH7PA, Toray Silicone DC11PA, Toray Silicone SH21PA, Toray Silicone SH28PA, Toray Silicone SH29PA, Toray Silicone SH30PA, Toray Silicone 8400 (Manufactured by Toray Dow Corning Co., Ltd.) ), KP321, KP322 'KP323, KP324, KP326, KP340, KP341 (manufactured by Shin-Etsu Chemical Co., Ltd.), TSF400, TSF401, TSF410, TSF4300, TSF4440, TSF4445, TSF-4446, TSF4452, TSF4460 (Momentive Performance Materials Japan Manufacturing) and so on. The fluorine-based surfactant may, for example, be an interface active agent having a fluorocarbon chain. Specifically, Fluorad (registered trademark) FC430, Fluorad FC431 (manufactured by Sumitomo 3M Co., Ltd.), MEGAFAC (registered trademark) F142D, MEGAFAC F171, MEGAFAC F172, MEGAFAC F173, MEGAFAC F177, MEGAFAC F183, MEGAFAC F554 MEGAFAC R30, MEGAFAC RS-718-K (manufactured by DIC Corporation), Eftop (registered trademark) EF301, Eftop EF303, Eftop EF351, Eftop EF352 (manufactured by Mitsubishi Materials Electronic Chemicals Co., Ltd.) Surflon (registered trademark) S381 ' Surflon S382, Surflon SC101, Surflon SC105 (manufactured by Asahi Glass Co., Ltd.), E5844 (manufactured by Daikin Fine Chemical Co., Ltd.), and the like. Examples of the polyfluorene-based surfactant having a fluorine atom include a surfactant having a cerium oxide bond and a fluorocarbon bond in I61707.doc - 46 - 201235784. Specifically, it can be listed as MEGAFAC (registered trademark) R08, MEGAFAC BL20, MEGAFAC F475 'MEGAFAC F477' MHGAFAC F443 (manufactured by DIC Corporation). These surfactants may be used singly or in combination of two or more. The content of the surfactant (G) is preferably 0.001% by mass or more and 〇2% by mass or less based on the total amount of the colored photosensitive resin composition of the present invention, and is preferably 0-002% by mass or more. In the following, it is more preferably 1% by mass or more and 0.05% by mass or less. When the content of the surfactant (F) is in the above range, the flatness of the coating film can be improved. The coloring property of the present invention is also Various additives such as a filler, another polymer compound, an adhesion promoter, an antioxidant, an ultraviolet inhibitor, a light stabilizer, and a chain transfer agent (hereinafter sometimes referred to as "other components") may be contained as needed. The coloring photosensitive resin composition can be used, for example, by using a coloring agent (A), a resin (8), a polymerizable compound (c), a polymerization initiator (9), a solvent (8)', and a polymerization initiator which is used as needed. The surfactant (G) and other components are prepared by mixing. It is preferred to previously mix the pigment with a part or all of the solvent (8) and disperse it using a bead mill or the like until the average particle diameter of the pigment is Μ(4) or less. In the case of the second time, the pigment dispersant, the tree 9 or all of the above may be blended as needed, and the remaining component of the obtained pigment dispersion liquid may be a specific concentration of the photosensitive resin composition. Prepare the color 161707.doc •47- 201235784, to prepare a cold liquid in part or all of the P mountain P star dye dissolved in the solvent (E) in advance. It is preferably a filter using a pore size of G.G1~1 μηη. The solution is filtered. It is preferred to filter the colored photosensitive resin composition prepared as described above by using a filter having a pore size of 〜1 to 1 around the squeaking. The coloring resin composition of the present invention is used to form the photosensitive resin composition. The method of coloring the color filter is exemplified by a lithography method and a method using an inkjet apparatus, etc. The lithography method is a method of forming a pattern by the following method: coloring the photosensitive resin composition of the present month Applying to a substrate or another resin layer (for example, a layer of another colored light-sensitive resin composition formed on the substrate), removing or drying a volatile component such as a solvent to form a dried coating film, and blocking the light. The dried coating film is exposed and developed. In the lithography method, a color filter film can be formed without using a photomask and/or development without developing, and a color filter can be produced. The film thickness of the filter is not particularly limited, and can be appropriately adjusted according to the material to be used, the use, etc., for example, 〇1 to 3〇μηι, preferably 1 to 20 μmη, and more preferably 1 to 6. The photosensitive resin composition is applied onto a substrate, and the solvent is removed by heat drying (pre-baking) and/or drying under reduced pressure to obtain a smooth dried coating film. As the substrate, quartz glass, borosilicate glass, or aluminum can be used. a glass plate such as a soda lime glass coated with cerium oxide on the surface, or a resin plate such as polycarbonate, polymethyl methacrylate or polyethylene terephthalate, on the substrate Aluminum, silver, silver/copper/kid alloy thin films are formed thereon. 161707.doc -48- 201235784 The coating method is exemplified by a spin coating method, a slit coating method, a slit &amp; spin coating method, and the like. The heat drying is preferably 30 to 2 〇 t &gt; c, more preferably 4 Å to 1 Torr. Hey. Further, as the heating time, it is preferably from 10 seconds to 60 minutes, more preferably from 30 seconds to 3 minutes. Preferably, the drying under reduced pressure is carried out under a temperature range of 5 Torr to 15 Torr. When the colored photosensitive resin composition of the present invention is subjected to drying under reduced pressure under such conditions, a volcano may be generated. Shape defects produce less effect. The film thickness of the coating film after drying is not particularly limited to $, and may be appropriately adjusted depending on the materials to be used, the use, and the like. After drying, the coating film is exposed through a reticle that forms a target pattern. At this time, the pattern on the photomask is not particularly limited, and those corresponding to the intended use can be used. As the light source used for the exposure, it is preferable to generate light having a wavelength of 25 〇 to 45 〇 nm. For example, a filter that can cut off this band can be used for the light of less than 35〇ηηΐ2, and a band pass filter that can extract the bands can be used for light of about 436 nm, about 4 〇 8 nm, and about 365 nm. The extraction is selectively performed. Specifically, a mercury lamp, a light emitting diode, a metal halide lamp, a halogen lamp, etc. are mentioned. Since the entire exposed surface can be uniformly irradiated with parallel rays, or the position of the mask and the substrate on which the dried coating film is formed can be prepared, it is preferable to use a mask alignment exposure machine, a stepper, or the like. . After the exposure, the colored portion can be obtained by dissolving and removing (i.e., developing) the unexposed portion by bringing it into contact with the developing solution. As the developer, for example, I61707.doc -49 - 201235784 dipotassium hydride, sodium bismuth carbonate or tetramethyl hydroxide is preferred. An aqueous solution of the substance. The test compound is in an aqueous solution = normalized 〇.〇1~10 mass. /. 'More preferably 0 / agricultural degree is better to contain interface activity (four) Bu W 'developing solution can also be 'Yang method can be material method, impregnation method, spray method, etc.' can be tilted to the substrate during development Any angle. It is preferred to carry out water washing after development. The post-baking temperature is preferably post-bake time preferably </ RTI> and may be post-baked as needed to be 150 to 250 ° C, more preferably 160 to 220 ° C. 1 to 120 minutes' is better for 10 to 60 minutes. According to the colored photosensitive resin composition of the present invention, a color light-receiving sheet having particularly few defects can be produced. The color light-emitting sheet is used as a display device (for example, a liquid crystal display device, an organic EL (e.g., electroluminescent) device, and an electronic paper) or a color filter used for a solid-state image sensor. EXAMPLES Hereinafter, the "%" and "parts" in the examples of the coloring photosensitive resin composition of the present invention will be described in more detail by way of examples, and unless otherwise specified, the amounts are % by mass and parts by mass. Synthesis Example 1 Into a flask equipped with a cooling tube and a stirring device, a mixture of a compound represented by the formula (A〇_1} and a compound represented by the formula (A0-2) (manufactured by a Chinese company) was introduced. 〇份 and 8.9 parts of N,N-dimethyl decylamine, while mixing and maintaining below 20 ° C, add 10.9 parts of sulfite gas. After the end of the dropwise addition, the temperature is raised to 50 ° C. The temperature was maintained and reacted for 5 hours, after which 161707.doc • 50·201235784 was cooled to 20 ° C. The cooled reaction solution was stirred and maintained at 20 ° C or lower, and 2-ethylhexylamine 12.5 was added dropwise. And 22.1 parts of triethylamine in the exhibition liquid. Thereafter, search at 20 C; mix and react for 5 hours. Then, the obtained reaction mixture is subjected to solvent distillation in a rotary evaporator, and then a small amount of sterol is added. The mixture was stirred vigorously, and the mixture was added to a mixed solution of 375 parts of ion-exchanged water to cause precipitation of crystals. The precipitated precipitate was filtered off, washed thoroughly with ion-exchanged water, and dried under reduced pressure at 6 Torr. Obtaining dye Al (compound of compound (1_υ~ compound (1_8)) u 3 parts

16l707.doc •51- 201235784

Synthesis Example 2 The compound obtained by the formula (1 χ) was mixed with 2 parts of N-ethyl o-toluidine (manufactured by Wako Pure Chemical Industries, Ltd.) under a light-shielding condition, and the obtained solution was mixed. Stir at 110 ° C for 6 hours. After the obtained reaction liquid was cooled to room temperature, the mixture was added to a mixture of 800 parts of water and 50 parts of 35% hydrochloric acid, and the mixture was stirred at room temperature for 1 hour to precipitate crystals. The precipitated crystals were suction-filtered to obtain a residue, which was then dried to obtain 24 parts of the compound represented by the formula (1_31). The yield was 80%.

Exact mass: 602.2 Synthesis Example 3 A formula (1-39) was obtained in the same manner as in Synthesis Example 1 except that N-propyl-2,6-dimercaptoaniline was used instead of N-ethyl-o-methylamine. Represented as compound 0 I6l707.doc •52· 201235784

Identification of the compound represented by the formula (丨-39) (mass analysis) ionization mode = ESI + : m / z = [M + H] + 659.9 Exact mass : 658.9 Synthesis Example 4 With a reflux cooler, a dropping funnel and In a flask of a stirrer, nitrogen gas was introduced at L2 L/min to form a nitrogen atmosphere, and 5 parts by mass of ethyl lactate was added thereto, and the mixture was heated to 7 (TC) while stirring. Then, 60 parts by mass of methacrylic acid and acrylic acid were added. 3,4-epoxytricyclo[5·21 〇2.6] oxime ester (the compound represented by the formula (M) and the compound represented by the formula (II-1) are mixed in a molar ratio of 50:50) A solution was prepared by dissolving 240 parts by mass and 4 parts by mass of ethyl lactate, and the solution was dropped into a flask kept at 70 ° C for 4 hours using a dropping funnel.

Obtaining a weight average molecular weight "...9" xlO3, molecular weight distribution of 2.5, solid I6I707.doc -53·201235784 Shape component 33% by mass 'Solvent B1 solution of acid value 34 mg-KOH/g. According to the above solid matter The composition and the acid value of the solution were calculated, and the acid value of the solid content of the resin B was 100 mg-KOH/g. The resin B 1 had the structural unit shown below.

Synthesis Example 4 182 g of propylene glycol monoterpene ether acetate was introduced into a flask equipped with a stirrer, a thermometer, a reflux cooling tube, a dropping funnel, and a nitrogen introduction tube, and the temperature in the flask was changed from air to nitrogen, and then the temperature was raised to 100°. After C, it will contain 70.5 g (0.40 mol) of benzyl methacrylate, 43 g of methacrylic acid (〇5 mol), and dicyclopentanyl thioglycolate (FA-513M manufactured by Hitachi Chemical Co., Ltd.) A mixture of 22.0 g (0.10 mol) and 136 g of propylene glycol monoterpene ether acetate was added dropwise with a solution of 3.6 g of 2,2'-azobisisobutyronitrile, and stirring was continued at 100 °C. Then, the atmosphere in the flask was changed from nitrogen to air, and glycidyl methacrylate was 35.5 g [0.25 mol' (50 mols relative to the carboxyl group of the mercaptoacrylic acid used in the reaction). (diammonium) 0.9 g of nonylphenol and 0.145 g of hydroquinone were placed in a flask, and the reaction was continued at U〇〇CT to obtain a resin B2 having a solid content of 32% and a solid content of 79 mgKOH/g. Solution. Measured by GPC (gel permeation chromatography) in terms of polystyrene. 161707.doc • 54· 201235784 The weight average molecular weight is 30,000. The weight average molecular weight (Mw) and the number average molecular weight (??) of the resin obtained in the synthesis example were measured by the GPC method under the following conditions. Device: Κ2479 (made by Shimadzu Corporation)

- Column: SHIMADZU Shim-pack GPC-80M

Column temperature: 40 ° C Solvent: THF (Tetrahydrofuran, tetrahydrofuran)

Flow rate: 1 · 0 mL / min. Detector: RI calibration standard substance · TSKSTANDARDPOLYSTYRENEF-40, F-4, F-288, A-2500, A-500 (manufactured by Tosoh Co., Ltd.) The ratio of the weight average molecular weight and the number average molecular weight (Mw/Mn) in terms of polystyrene is taken as the molecular weight distribution. Examples 1 to 12 and Comparative Example 1 The components were mixed so as to have the compositions shown in Tables 1 and 2 to obtain a colored photosensitive resin composition. 161707.doc -55- 201235784 Table 1 Units are (parts) Example Comparative Example 1 2 3 4 5 6 1 Colorant (Α) (A-1V) 23 23 23 23 23 23 20 (Α-2) 7 7 7 7 7 7 3.5 Acrylic dispersant 9 9 9 9 9 9 5 Resin (Β) (Β-1) 40 40 40 40 40 40 (in terms of solid content) (Β-2) 50 Polymerizable compound (C) ( C-1) 60 60 60 60 60 60 50 Polymerization initiator (D) (D-1) 10 10 10 10 10 10 15 (ED 44 62 79 84 89 93 (Ε-2) 149 149 149 149 149 149 Solvent (Ε) (Ε-3) 560 542 524 520 515 511 (Ε-4) 131 131 131 131 131 131 244 (Ε-5) 289 Table 2 Units are (parts) Example 7 8 9 10 11 12 Colorant ( Α) (A-1), J 23 23 23 23 23 23 (A-3) 7 7 7 7 7 7 Acrylic dispersant 9 9 9 9 9 9 Resin (Β) (in terms of solid content) (B- 1) 40 40 40 40 40 40 (B-2) Polymerizable compound (C) (C-1) 60 60 60 60 60 60 Polymerization initiator (D) (D-1) 10 10 10 10 10 10 Solvent ( Ε) (E-1) 44 62 79 84 89 93 (E-2) 149 149 149 149 149 149 (E-3) 560 542 524 520 515 511 (E-4) 131 131 131 131 131 131 Surfactant ( G) (G-1) 0. 21 0.21 0.21 0.21 0.21 0.21 In Tables 1 and 2, (A-1) fluorene was mixed with an acrylic dispersant and a total amount of propylene glycol monoterpene ether acetate, and dispersed and used in advance. In (1), the acrylic dispersing agent and 137 parts of propylene glycol monoterpene ether acetate were mixed and used previously, and the components are shown in Table 1 and Table 2 below. (A), (Al) : CI Pigment Blue 15 : 6 (Pigment) 161707.doc • 56- 201235784 Colorant (A), (A-2). Dye A1 (p-mountain dye) Colorant (A) (A-3): a compound represented by the formula (1-39) (anthraquinone dye) Resin (B), (B-1): Resin B1, which shows the parts by mass in terms of solid content. Resin (B) '(B-2): Resin B2, which shows the parts by mass of the solid content. Polymerizable compound (C) '(C-1): dipentaerythritol hexaacrylate (KAYARAD DPHA, manufactured by Nippon Kayaku Co., Ltd.) Polymerization initiator (D) '(Dl) : N·benzoquinone 4 -(4-phenylthiophenyl)octane-1-one-2-imine (Irgacure OXE 01, manufactured by BASF JAPAN Co., Ltd.) Solvent (E), (E-1): Dipropylene glycol monoterpene ether acetate vinegar Solvent (E), (E-2): propylene glycol monomethyl ether solvent (E), (E-3): ethyl lactate solvent (E), (E-4): propylene glycol monomethyl ether acetate solvent (E) ) '(E-5) : 4-hydroxy-4-indolyl-2-pentanone surfactant (G), (G-1): polyether modified polysiloxane (T〇ray)

Silicone SH8400 . manufactured by Toray Dow Corning Co., Ltd. &lt;Production of coloring pattern&gt; Coating coloring on a 2 inch square glass substrate (Eagie 2®, manufactured by Corning) by spin coating After the photosensitive resin composition, it was prebaked at 100 C for 3 minutes to form a dried coating film. After being left to cool, the interval between the substrate on which the dried coating is formed and the quartz glass mask having the pattern (twisted line and gap pattern) is set to 1 μm, and 161707.doc • 57· 201235784 Light exposure was carried out in an atmospheric environment at an exposure amount of 150 mJ/cm 2 (365 nm basis) using an exposure machine (TME-150RSK 'TOPCON Co., Ltd.). The coating film was allowed to contain 0.12 Å/min of a nonionic surfactant at 23 ° C after light irradiation. The solution was immersed and developed in an aqueous developing solution of 0.04% of potassium aroxide for 80 seconds, washed with water, and then baked in an oven at 22 ° C for 2 minutes to obtain a colored pattern. After the film was allowed to stand for cooling, the film thickness of the obtained color pattern was measured to be 2.2 μηι using a film thickness measuring device (DEKTAK3, manufactured by 曰本 Vacuum Technology Co., Ltd.). &lt;Chroma evaluation&gt; The color separation pattern obtained was measured by a color measuring machine (〇Sp_Sp_2〇〇, manufactured by Olympus Co., Ltd.), and the characteristic function of the C light source was used to measure the XYZ color system of CIE. The xy chromaticity coordinates (Βχ, By) and the tristimulus value Y. A larger Y value indicates a higher brightness. The results are shown in Tables 3 and 4 〇 &lt;Defect Evaluation&gt; The colored photosensitive resin composition was applied onto a 3 inch square glass substrate (Eagle 2®, manufactured by Corning Incorporated) by a spin coating method. It was dried in a vacuum dryer (manufactured by VCD MICROTEK Co., Ltd.) until the degree of decompression reached 0_5 torr. Then, in a dust-free supply box, the coating film after drying was formed on the substrate by prebaking for 3 minutes. The surface shape optical microscope (magnification 250 times 'VF-75 10 ' manufactured by KEYENCE Co., Ltd.) was observed to observe that the dried coating film was counted as the whole of the substrate except for a range of 1 cm from the end of the substrate. The number of defects in the shape of a crater. The results are shown in Tables 3 and 4. I61707.doc •58·201235784 &lt;Heat resistance evaluation&gt; A colored coating film was produced in the same manner as in the patterning except that the mask was not used at the time of exposure. The coloring film and the tristimulus value γ were measured in the same manner as above by heating the colored coating film for 2 hours in an oven at 23 Torr. The color difference AEab氺 is calculated from the chromaticity before and after the heating and the tristimulus value Y. The smaller the color difference ^Eab*, the smaller the color change before and after heating, and the better the heat resistance. The value of the obtained color difference AEab* is shown in the "heat resistance" of Tables 3 and 4. table 3

Bx Example I 0.150 Example 2 Example 3 0.150 Example 4 0.150 Example 5 0.150 Example 6 0.150 Comparative Example 1 0.150 0 150 By 0.087 0.087 0.087 0.087 0.087 0.087 0 087 Y 9.9 9.9 9.9 9.9 9.9 9.9 9 〇 Defects ( 8) 5 7 5 4 2 55 Heat resistance 3.2 3.1 3.3 3.3 3,1 3.2 •jj 3.3 Table 4

(Examples 13 to 18) A coloring photosensitive resin composition was obtained in the same manner as in Example 丨6 except that the compound represented by the formula (1-31) was used instead of the dye A1. The same operation as above was carried out to obtain a dry after-coating with less defects. 161707.doc •59·201235784 The film was dyed with a color pattern excellent in brightness or heat resistance. According to the above results, it is understood that the colored photosensitive resin composition of Example 12 can obtain a post-drying coating film having few defects without lowering the brightness or the heat of the obtained color filter. By forming the dried coating film from the colored photosensitive resin composition of the present invention and forming the colored pattern obtained from the dried coating film into a color filter ', a display device can be manufactured with high yield. Industrial Applicability The colored photosensitive resin composition of the present invention is dried under reduced pressure after being applied onto a substrate, and the occurrence of crater-like defects on the coating film after drying is small. I61707.doc 60-

Claims (1)

201235784 VII. Patent application scope: 1_ A colored photosensitive resin composition containing a coloring agent, a resin, a polymerizable compound, a polymerization initiator and a solvent, the coloring agent containing an anthraquinone dye and a pigment, and the solvent containing dipropylene glycol Monomethyl ether acetate. 2. The colored photosensitive resin composition according to claim 1, wherein the content of the dipropylene glycol monomethylhydrazine acetic acid® in the solvent is 0.1% by mass or more and 30% by mass or less. A colored photosensitive resin composition according to the item 1 or 2, wherein the solvent is added to contain ethyl lactate. The coloring photosensitive resin composition of Claim 3, wherein the solvent further contains propylene glycol monoterpene ether and/or propylene glycol monomethyl ether acetate. 5. The colored photosensitive resin composition according to item 1, wherein the resin is an alkali-soluble resin. 6. The colored photosensitive resin composition of claim 1, wherein the polymerizable compound is (mercapto) acrylate. A color light-passing sheet formed of the colored photosensitive resin composition of claim 1. 8. A display device comprising a color filter as claimed in claim 7. 161707.doc 201235784 IV. Designated representative map: (1) The representative representative of the case is: (none) (2) The symbolic symbol of the representative figure is simple: 5. If there is a chemical formula in this case, please reveal the best indication of the characteristics of the invention. Chemical formula: (none) 161707.doc