TW201037458A - Colored photosensitive resin composition - Google Patents

Abstract

The colored photosensitive resin composition of this invention comprises: coloring agent (A), alkali-soluble resin (B), photopolymerizable compound (C), photopolymerization initiator (D), solvent (E), and surfactant (F), wherein the coloring agent (A) comprises dye (A-1) and pigment (A-2) comprising compound represented by formula (1), the surfactant (F) comprises fluorine atom and/or silicon atom, and in 100 parts by mass of the colored photosensitive resin composition, the amount of the surfactant (F) is greater than 0.0005 part by mass and less than 0.3 part by mass.

Description

201037458 VI. Description of the Invention: [Technical Field of the Invention] The present invention relates to a colored photosensitive resin composition. [Prior Art] The photosensitive resin composition of the prior art contains a quinone squaraine compound as a dye and a blue pigment Pigment BiUe (p.B) 15 : 6 (for example, Patent Document 1). However, the coating film obtained by using the photosensitive resin composition may have insufficient brightness and flatness. [Patent Document 1] JP-A-2006-79012 SUMMARY OF THE INVENTION An object of the present invention is to provide a colored photosensitive resin composition which can further improve the brightness and flatness of a coating film. [1]. A coloring photosensitive resin composition comprising: a coloring agent (a), a solvent-soluble resin (B), a photopolymerizable compound (c), a photopolymerization initiator (D), a solvent (E), And a surfactant, and the colorant (A) comprises both a dye (A-1) and a pigment (A-2) containing a compound represented by the formula (1), and the surfactant (F) has a fluorine atom and/or Or a surfactant of a ruthenium atom, the content of the surfactant (F) is 0.0005 parts by mass or more and 〇3 parts by mass or less in 100 parts by mass of the colored photosensitive resin composition; 146511.doc (1) 201037458

(In the formula (1), each independently represents a hydrogen atom, 'R6 or a valence ring having a carbon number of 6 to 10: a hydrogen contained in an aromatic smoky group having a stone anisotropy of 6 to 1 Å Atomic atom n0H, collar 6, _s〇3_, s〇3H Zheng, 2, -C〇2R6 ' _S〇3R6 or -S〇2N (R8) RV kg substitution; R51 shows · S (V, -S〇3H '-so淞, -c〇2H, _c〇2R6, ~S〇3R or 4〇2; ^(118) feet 9; two means an integer from 0 to 5; in the case of the above integer, a plurality of R can The same 'may be different; X means _ prime atom; a means an integer of 0 or 1; R6 means a carbon number is a wou valence saturated hydrocarbon group; the carbon number is a hydrogen atom contained in the saturated group. Or the carbon number is replaced by an alkoxy group; the carbon number is A. which may be substituted by -〇-, -co- or _;^尺7_; R7 represents carbon number (7) The valence of a saturated hydrocarbon group; the hydrogen atom contained in the saturated smoky group having a carbon number of 卜1〇 may be substituted by a sulfonium atom or a ruthenium group having a carbon number of 1 to 1 (); R8 and R9 are each independently A hydrogen atom, a carbon group having a carbon number of 2, a cycloalkyl group having a carbon number of 3 to 30 or _Q; or a core 9 may be bonded to each other And forming a heterocyclic ring having a carbon number of H0; the hydrogen atom contained in the silk and the (tetra) group may be substituted by 1465l U 〇c 201037458 dentate atom OH Q, _ch=CH4_Ch=; Chr6; the alkyl group and the naphthenic group The _CH2_ contained in the group may be substituted by _〇_, _c〇·, _NH_ or -NR6-; the hydrogen atom contained in the heterocycle having a carbon number of n opposite von 1~10 may pass through -R6, -OH or -Q is substituted; Q represents an old aromatic hydrocarbon group having a carbon number of 6 1 或 or a valence Ο Ο 香 族 aromatic heterocyclic group of the ring of the member, the hydrocarbon group of the group and the heterocyclic group of the group The nitrogen atom contained in the towel may be substituted by a functional atom, rhyme, _r6, _〇r6, _n〇2, _cH=cH2 or -CH=CHR6; Μ represents a nano atom or a potassium atom; wherein, by formula (1) [2] The composition of [1], wherein the ratio of the content of the dye (Α-1) to the content of the pigment (eight_2) is 1: 99~99 : 1. [3] . The composition of [1] or [2] wherein the pigment (Α2) is a pigment containing ci (c〇i eye Index 'dye index) Pigment Blue 15: 6. [4] The composition of any one of [1] to [3], wherein the solvent (8) is a hydroxy group containing hydrazine Solvent solvent [5] · A coloring pattern 'formed using a composition such as [1] to [4] towel. [6] . A color filter comprising [5] [7] A color filter such as [6], which is formed by photolithography. The m·-m display device 'includes a color calender as in [6] or [7]. [9] Use of a composition according to any one of [1] to produce a color filter. 1465Il.doc 201037458 [Embodiment] The colored photosensitive resin composition of the present invention comprises a coloring agent (a), an alkali-soluble resin (B), a photopolymerizable compound (c), a photopolymerization initiator (1), and a solvent ( E), and surfactant (ρ). In the present specification, the following substituents differ depending on the carbon number. However, unless otherwise specified, the same ones are exemplified in any of the chemical structural formulae. Further, a substituent which may take both a straight chain or a branched chain includes a substituent which takes a linear chain and a substituent which takes a branch. The colorant (A) contains both the dye 1) and the pigment (A-2) containing the compound represented by the formula (I). R2 R3

(In the formula (1), R to R each independently represent a hydrogen atom, _R6 or an valence-valent aromatic hydrocarbon group having a carbon number of 6 to 1 Å, and a hydrogen atom contained in the aromatic hydrocarbon group having 6 to 10 carbon atoms; Substituted by an atom of an atom, -R6, -_0H, _〇r6, _s〇., s〇3H, s〇3M, -C〇2H, -C02R6, -S03R6 or _s〇2N(R8)R9; Table -S03·, -S03n, _s〇3M, .C02H, -C〇2R6, -S〇3R6 or _s〇2N(R8)R9; m represents an integer from 0 to 5; In the case of a case, a plurality of R5s may be the same or different; X represents a halogen atom; a represents an integer of 〇 or 1; 146511 .doc 201037458 The rhyme of the heart is (a) ... recharge (four): the carbon number is (4) the saturated base Yin The hydrogen atom contained may be replaced by a dentate atom or a carbon number, which is a sulphuroxy group, and the mother contained in the saturated tobacco group having a carbon number of H0 may be via _〇-, -CO- or - Substituted by NR7-; R indicates that the number of rabbits is a valence saturated nicotine group, and the carbon number contained in the saturated nicotine group can be replaced by a dentate atom or a decyloxy group having a carbon number of ruthenium; R8 and R9 independently represents a hydrogen atom, a carbon number of (10), and a carbon number of 3 to 3 a cyclization group or _Q; or may be bonded to each other to form a heterocyclic ring having a carbon number of 1 to 1 Å; the alkyl group contained in the alkyl group and the ring-burning group may be added to the atom of the element ,,, or 2, substituted by heart = coffee 6; the alkyl group and the _CH2_ contained in the alkyl group may be replaced by _〇_, -CO·, 丽_ or NR6_; The chlorine atom contained in the hetero ring of H0 may be substituted by -OH or -Q; Q represents a monovalent aromatic fluorenyl group having a carbon number of 6 to 1 fluorene or a 5- to 10-membered ring! The 'an aromatic smoki group and the hydrogen atom contained in the aromatic heterocyclic group may be substituted by an imine atom, a collar, _r6, rhythm 6 n〇2, _ch=ch2 or -CH=CHR6; In the case of the aromatic hydrocarbon group, the aromatic hydrocarbon group is exemplified by the formula (1), wherein the number of the charge is the same as the number of the charge. Hyunji, aryl groups substituted by the hospital base. Examples of the aryl group include a phenyl group, a biphenyl group, a naphthyl group, an anthracenyl group, and a phenanthryl group 146511.doc 201037458. The aralkyl group may, for example, be a benzyl group, a phenethyl group, a phenylpropyl group, a triphenylmethyl group, a naphthylmethyl group or a naphthylethyl group. The aryl group substituted with a mercapto group may be any combination of the above aryl group and the alkyl group exemplified below. Examples of the ii atom atom include fluorine, gas, and bromine. The saturated hydrocarbon group may be an alkyl group, a cycloalkyl group, an alkyl-substituted cycloalkyl group in which the substituents are arbitrarily combined, or a cycloalkyl-substituted alkyl group. The alkyl group may, for example, be a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, an isobutyl group, a pentyl group, an isopentyl group, a neopentyl group, a hexyl group, a heptyl group, an octyl group or a 1-fluorenyl group. Propyl, 2-methylpropyl, N-methylbutyl, 2-decylbutyl 3-methylbutyl, 2-ethylhexyl, decyl, decyl, bromo-n-propyl, 1 , 2-dimethylpropyl, 2,2-dimethylpropyl, and the like. The cycloalkyl group may, for example, be a cycloalkyl group such as a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexylcycloheptyl group, a % octyl group or a tricyclodecyl group. Examples of the alkoxy group include a methoxy group, an ethoxy group, a propoxy isopropyl group, a butoxy group, an isobutoxy group, a pentyloxy group, an isopentyloxy group, a hexyloxy group, a heptyloxy group, and the like. Octyl, 1-methylpropoxy, 2-mercaptopropoxy, Methyl: 2 methylbutoxy, 3-methylbutoxy, ethylhexyloxy, decyloxy , 癸 cover its 1 -' ', l-dimethyl propoxy, hydrazine, 2 - dimethyl propoxy, 2,2- dimethyl propoxy and the like. By.乍 is a hetero-based group 'may be aromatic' or may not be aromatic as an aromatic heterocyclic group, exemplified by: 146511.doc 201037458

NT

, NH NT

Ring, can be enumerated as a miscellaneous

'The key of the clothing base can be set to be the same as the position described above. In addition, any position of butoxy group, as -OR6, can be listed as a rebel. Tian Jie w - Xi Xi]. Alkoxy groups such as methoxy, ethoxy propoxy hexyloxy, 2-ethylhexyloxy, etc. .

Examples of the C02R' include an oxiranyl group, an ethyl group, a propoxy group, an isopropoxy group, an oxy group, an isobutoxy group, a pentyloxycarbonyl group, and the like. Isovalerylcarbonyl, neopentyloxycarbonyl, cyclopentyloxycarbonyl, hexyloxycarbonyl, cyclohexyloxycarbonyl, heptyloxycarbonyl, cycloheptyloxycarbonyl, octyloxycarbonyl, 2-ethylhexyl Oxycarbonyl, cyclooctyloxycarbonyl, decyloxycarbonyl, decyloxycarbonyl, tricyclodecyloxycarbonyl, methoxypropoxycarbonyl, ethoxypropoxycarbonyl, hexyloxypropoxycarbonyl 2—Ethylhexyloxypropoxycarbonyl, methoxyhexyloxycarbonyl, and the like. Examples of the -so3r6 include a methoxysulfonyl group, an ethoxysulfonyl group, a hexyloxysulfonyl group, and a decyloxysulfonyl group. 146511.doc 201037458 As R9 is a hydrogen atom -so2n(r8)r9 (ie -so2nhr8), examples thereof include amidoxime, N-(methyl)aminesulfonyl, N-(ethyl)aminesulfonate , N-(propyl)aminesulfonyl, N-(isopropyl)aminesulfonyl, N-(butyl)aminesulfonyl, N-(isobutyl)aminesulfonyl, N- (pentyl)aminesulfonyl, N-(isopentyl)aminesulfonyl, N-(neopentyl)aminesulfonyl, N-(cyclopentyl)aminesulfonic acid, N-(hexyl) Aminesulfonyl, N-(cyclohexyl)aminesulfonyl, N-(heptyl)aminesulfonyl, N-(cycloheptyl)aminesulfonyl, N-(octyl)aminesulfonyl, N-(2-ethylhexyl)amine sulfonyl, n-(1,5-didecylhexyl)amine sulfonyl, N-(cyclooctyl)amine sulfonyl, N-(decyl)amine sulfonate Sulfhydryl, N-(fluorenyl)amine sulfonyl, N-(tricyclodecyl)amine sulfonyl, N-(methoxypropyl)amine sulfonyl, N-(ethoxypropyl) Aminesulfonyl, N-(propoxypropyl)aminesulfonyl, N-(isopropoxypropyl)aminesulfonyl, N-(hexyloxypropyl)aminesulfonyl, N_(2- Ethylhexyloxypropyl)aminesulfonyl, N-methoxydecylhexylaminesulfonyl, N-(3-benzene Base_丨_methylpropyl)aminesulfonyl and the like. Further, _S〇2N(R8)R9 wherein R9 is a hydrogen atom is exemplified by the following formula. Here, in the following formula, χ1 represents a γ atom. Χ3, an alkyl group having an inverse number of 1 to 3 or an alkoxy group having a carbon number of 1 to 3, and a halogen atom of the alkyl group and the alkoxy group may be substituted by a functional atom. X2 represents a carbon number of 1 to 3 = the base carbon number is an alkoxy group, a sulfonium atom or a nitro group, and the hydrogen atom of the ray group and the meta-oxide can be substituted by a _ atom. The alkyl group having a carbon number substituted by a dentate atom is fluorene, and examples of the above-mentioned alkyl group include a perfluoromethyl group and the like. Examples of the alkoxy group having a carbon number of 丨~3 which may be substituted by a halogen atom include a pit group, particularly a methoxy group, an ethoxy group, a propoxy group or the like. J46511.doc 10 201037458

NHSOs 146511.doc -11 - 201037458

OH j \^k/NHS〇2 HO^^NHS〇2 nhs〇2 h〇Js^NHS〇2

HO

NHS〇2

146511.doc •12· 201037458

H^-nhsc^ ^^ΜΒ〇2〇ϊ\Χ { f , X I NHS〇2 ^^NHSQs MeO 八MHSOi MHS〇2 "Y^NHSOi “ jj^^NHSCJs

O O

O

%A CF3CH2NHS〇2 CF3(CF2)7CH2NHS〇2 CIv^/v^Js^NHSOj ❹ o NHS〇2 NHS〇2 NHSQz NHSpz NHS〇2 NHSOj NHSOs -rp2

I NHS〇2 z〇Me NHSO2 o2n

N〇2 N〇2

F

F

a

•Clz NHS〇2 NHS〇2 Br Br, /L yBr

Ms〇2 nhs〇2

_Ci Br/^^CF3

Br NHS〇2 NHSOs (〇CF3 q NHS〇2 NHS〇2 Br NHS〇2

N〇2 CF3

N〇2 N〇2

NHS〇2 , NHS〇2 Cl

OMe

, NHS〇2

NHS〇2 146511.doc • 13 - 201037458

NHS〇2 is a group of S02N(R8)R9 in which R8 and R9 are each a hydrogen atom, and the following groups are mentioned.

Examples of the hetero ring formed by bonding R8 and R9 to each other include a group represented by the following formula.

• 14· 146511.doc 201037458

广0〆

❹ Ο wherein R8 and R9 are preferably a linear or branched alkyl group having a carbon number of 丨~(7), a cycloalkyl group having a carbon number of 5 to 7, an allyl group, a phenyl group, and a carbon number of An aralkyl group of 8 to 10, a hydroxyl group-containing alkyl group and an aryl group having 2 to 8 carbon atoms, an alkoxy group-containing alkyl group and an aryl group having a carbon number of 28, more preferably a carbon number of 68. Branched alkyl. The substituent of the aromatic hydrocarbon group having a carbon number of 6 to 10 is preferably 146511.doc •15- 201037458 -S〇2N of ethylbenzene H phenyl, dimethylphenyl, _s〇3RSilR9 is a hydrogen atom. (R8) R9. Here, as R8 in which R9 is a hydrogen atom, R8' in the s〇2N(r8)r9 is particularly a linear or branched alkyl group having a carbon number of 1 to 10 and a carbonaceous group having a carbon number of 3 to 30. Preferably, the alkyl group is a straight or branched alkyl group having a carbon number of 丨~(7), more preferably a branched alkyl group having a carbon number of 6 to 8, particularly preferably 2-ethylhexyl. The aromatic hydrocarbon group having a carbon number of 6 to 1 Å which may be substituted may, for example, be methylphenyl, dimethylphenyl, trimethylphenyl, ethylphenyl or hexylphenyl 'nonylphenyl , fluorophenyl, phenyl, phenyl, phenyl, methoxy, dimethoxyphenyl, ethoxyphenyl, hexyloxyphenyl, decyloxyphenyl, tri A fluoromethylphenyl group or the like, and a group further substituted with -so2n(r8)r9 on the above-mentioned other groups. Preferably, at least one of 疋R and R2, or at least one of R3 and R4 is an alkyl group having a radiant number of 1 to 4 or an optionally substituted aromatic hydrocarbon group having 6 to 10 carbon atoms. /Good is at least "solid" in Ri and R2, and the number of carbon atoms in the range of (10) to h is 1~4 or the substituted carbon number is 6~1 (). At least (10) of R] and at least h of r\r4 are substituted aromatic hydrocarbon groups having a carbon number of 6 to 1 G. R5 is preferably a carboxypropyl propyl sulfonyl group, Methyl propyl)amine sulfonate is represented by the formula G1) to formula (1-4) of the formula (1), ethoxycarbonyl, sulfo, N_(2-ethylhexyloxy N^1, 5 - dimethylhexyl)amine sulfonyl, N-(3, alkalyl, N-(isopropoxypropyl)amine sulfonyl. A compound other than, for example, preferably selected from the group consisting of At least one of the group consisting of 146511.doc 16 - 201037458.

(R25)ffl R31,

R

^ 于)a CM) (in the formula (1-1)~(1_4), R 1 , only 12, i * ” respectively represent hydrogen; f sub... the aromatic furnace flying atom with a stone inverse of 6~10 The hydrogen atom contained in the 6th or 1st price of the person, the base, and the number of slaves is 6~10. The hydrogen atom contained in the fangxiang atom can be passed through the dentate atom, the "hydrocarbon group-S03H, ςΓ> μ OH, ~〇R6,- So3-a mother Na, _C〇2h, _c〇2r6 substituted; ^ ~s〇2Nr8r9 represents a hydrogen atom, _S〇3·, _s〇3H or pe n(r8)r9; represents _s〇3_, -S03h or - so2N(R8)R9; aryl 2: π independently represents a hydrogen atom, -R26 or a carbon number of 6~i. The base ''the gas number and the amp contained in the aromatic hydrocarbon group having a carbon number of 6 to 1G Halogen atom, _R26, 〇卩26 κ, -OH, -〇R, -S03-, _s〇3Na •c〇2R26, -s〇3H, -so3R26 or -S〇2NHR28; R2$ 矣—示·δ〇3·, -SO song, -C02H, _c〇2r26, -so3hs S〇2NHR28 ·

R26 JL shows a saturated smoky group with a number of enemies of 1 to 10; the carbon number is 】 】 i 465 i46531.doc • 17- 201037458 The gas atom contained in the hydrocarbon group can be passed through sheet metal + ^ ^ ^ ^ ~10 is replaced by a burning oxygen 1 group or a halogen atom; ' indicates, Mu'. Or a monovalent aromatic hydrocarbon group having a carbon number of 6 to 1 Å, and the carbon atom having a carbon number of 6 to 10 is not + Λ _ _ 被 U U U U 被 被 被 被 被 被 被 被 被 被 - - - - Substituted; R3^R32 independently represents a carbon number of 6~1. The monovalent aromatic nicotyl group preferably represents a phenyl group; the hydrogen atom atom contained in the aromatic hydrocarbon group, -R26, -OR%, _C(), r26 ςη r2, Ώ 匕(10), -so3r26 Or _s〇2Nhr28 is substituted; R33 represents -S03· or -S02NHR28; R34 represents a hydrogen atom, -so3. or -so2nhr28; and f and R42 each independently represent an aromatic smoky group having a carbon number of 6 to 1 G, preferably The phenyl group; the hydrogen atom contained in the aromatic hydrocarbon group may be substituted by R -so2nhr28; 3 R43 represents -S03- or -S〇2NHR28; r6, R8, R9, m, X and a represent the same as above The meaning of which is 'the best is the formula (1_4). The compound represented by the formula (^) to (9) is exemplified by the formula (1), wherein the number of charges represented by the formula (1) is the same as the number of charges.

(1a) I465II.doc •18- 201037458

-S02NHRa ; R R and 11 respectively represent -S03·, -S03Na or -S02NHRa; R, R and R/ respectively represent a hydrogen atom, _s〇3_, s〇3H or -S02NHRa;

Ra represents an alkyl group of 1 to 10, preferably 2-ethylhexyl; X and a have the same meanings as defined above. The compound represented by the formula (lb) is represented by the formula (lb.1). Tautomers of the compounds. Among them, preferred are formula (le) and formula (If). The compound represented by the formula (1) can be chlorinated, for example, by a usual method, by oxidizing a dye or a dye intermediate having -S〇3H, and reacting the obtained pigment or pigment intermediate with an amine represented by R8_NH2. In the same way as above, it can be used in the same manner as above, by the patent of the special 14651].doc -19- 201037458 Kaiping 3-78702 bulletin 3f $ 死 f·撼山凡 a孜弟贝's upper right column ~ The pigment produced by the method of the left lower 襕 _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ As the box Δ, a, contained in the coloring agent (A). (3), 2), can be listed as organic pigments' For example: CI pigment blue 15, 15 „ 4, 15 : 6, 60, etc.; 1,19,23,29,32,-purple= ... two: there is at least one pigment selected from CJ. Pigment red purple, especially blue m箄幵 (1) good 疋 containing ci·pigment right ^ early use alone' can also be used in combination of two or more. Organic pigments can be used as needed Implementation. ^ 广乂理. Rosin treatment, # used to enter the acid or basic base of the pigment 导入 use „ A soil milk to find the surface treatment, #用古八子化合物, etc. on the pigment surface #吏用间刀A micronization treatment such as a method, a grafting treatment, a cleaning treatment using sulfuric acid fine particles or the like, an organic solvent or treatment for removing impurities by ionic impurities, and the like. The removal of the organic pigment by the ion exchange method, etc., is preferably a particle size-line dispersion treatment, and P is obtained. Hunting is carried out by a dispersion containing a pigment dispersant. The pigment which is in a state in which the coating material is dispersed in the solution is, for example, a cationic dispersion or an anionic active agent. This case is more than an interface type such as t-amine or acrylic. The knives can be used alone or in combination with pigments (A_2) in the case of pigment dispersants. When used, the amount is relative to 1 mass per gram.

It is preferable that the amount is 1 or more and the amount of 〇 5 is temporarily less than the amount of injury, and more preferably 0.05 or more. When the amount of the pigment dispersant used is in the range of J4651I.doc 〇 • 20· 201037458, it is preferred that the pigment dispersion liquid in a uniformly dispersed state can be obtained. The content of the colorant (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 in the colored photosensitive resin composition. %. Here, the solid matter refers to a total of components other than the solvent which are colored in the 'photoresin composition. 〜 When the content of the coloring agent (A) is within the above range, the color density of the color filter 4 is sufficient, and the desired amount of the binder polymer can be contained in the composition, so that the mechanical strength can be sufficiently formed. The pattern is therefore better. The coloring agent (A) has a dye (octa-" content of 3 to 8 % by mass, preferably 3 to 70% by mass, more preferably 3 to 5 % by mass. In the coloring agent (A) The content of the pigment (A_2) is from 2 to 97% by mass, preferably from 30 to 97% by mass, more preferably from 5 to 97% by mass. The ratio of the content of the dye (A-1) to the pigment (A_2) ( Mass ratio) Suitable for ι: 99~99 : 1 'Better is! : 99~6〇: 4〇, more preferably $: %~4〇〇60. Easy to achieve transmission by setting the above ratio The optimization of the spectrum is better for obtaining contrast and high brightness. Further, heat resistance and chemical resistance are good. In particular, the mass ratio of CI Pigment Blue 15 : 6 to dye (A_1} is 97 : 3 ～50: 50 is preferable, and more preferably 97: 3 to 70: 30. The colored photosensitive resin composition of the present invention contains an alkali-soluble resin (B). The testable resin (B) is not particularly limited, and may be used. Any resin is used. For example, 'the solubility-resolving resin (B) contains a structural unit derived from (meth)acrylic acid. Here, '(mercapto)acrylic acid means acrylic acid and/or mercaptopropyl C.酸.上146511.doc -21 - 201037458 Derived from (meth)acrylic acid-derived, and the content of 构 疋 于 in the total structural unit of the alkali-soluble tree month (B), Bi Haohao疋16 mol% or more and 4 〇 mol% or less, more preferably 18 straight and /, /, ear / 〇 or more and 38 mol% or less. If the content of the structural unit derived from the propylene material is in the above (4) The solubility in the non-pixel portion of the f is good, and the residue tends to remain in the non-pixel portion after development. Therefore, it is preferable to use the (meth) group to form the test-soluble resin (8). Other monomers other than the acrylic acid-derived structural unit, such as aromatic vinyl compounds, unsaturated acid vinegars, unsaturated acid amine ketones, and unsaturated monomers, may be mentioned. Acid glycidol brewing, vinyl acetate vinegar, unsaturated shouting, vinyl cyanide compound, unsaturated decylamine, unsaturated quinone imine, aliphatic copolydiene, in polymer molecular chain The terminal has a mono-propyl: thiol or monomethyl propylene-based macromonomer (9) The unit indicated, the unit represented by the formula (III), and the like.

(In the formulas (:) and (10), R53 and R55 each independently represent a hydrogen atom or a methyl group 'R and R each independently represent a hydrogen atom or a carbon group having a carbon number of 6; as a test resin (8), specifically Preferred is methyl methacrylate / methacrylic acid vinegar copolymer, methacrylic acid / methacrylic acid vinegar / benzene 146511.doc • 22· 201037458 ethylene copolymer, methacrylic acid / methacrylic acid Benzyl ester / methacrylate iso [sodium] ester copolymer, methacrylic acid / styrene / benzyl methacrylate / N-phenyl maleimide copolymer, methacrylic acid / by formula (II) a constituent component (wherein R53 represents a methyl group, R54 represents a hydrogen atom), a benzyl methacrylate copolymer, and a constituent represented by the formula (II) (wherein In the formula (II), R53 represents a methyl group, R54 represents a hydrogen atom) / benzyl methacrylate copolymer, methacrylic acid / a constituent represented by the formula (III), wherein 'in the formula (III), R55 represents a fluorenyl group, R56 represents a hydrogen atom)/styrene copolymer/tricyclodecyl methacrylate copolymer or the like. Particularly preferred in terms of hardenability and developability is an alkali-soluble resin (B) represented by the formula (IV). 〇

CH2 HOCH

〇=〇A l 3 A test-soluble resin (B) of a constituent represented by the formula (Π), for example, a mercaptoacrylic acid/constitutive component represented by the formula (Π), in the formula (11) R53 represents a methyl group 'r54 represents a hydrogen atom)/methacrylic (tetra)acetic acid copolymer', and a two-component polymer can be obtained by polymerizing methyl acrylic acid and mercaptoacrylic acid (tetra), and the obtained two components are obtained. The polymer is obtained by reacting a compound represented by the formula (7) (wherein, in the formula (7), r57 represents a chlorine atom). 146511.doc -23· (V) 201037458

(In the formula (V), R57 represents a hydrogen atom or an alkyl group having a carbon number of i to 6) methyl acrylate/constitutive component represented by the formula (m) (wherein, in the formula (m), H is shown曱H H shows gas atom v stupid copolymer/trimethyl methacrylate copolymer can be made by benzyl methacrylate, methyl acrylate, tricycloanthracene monomethyl propyl The dilute vinegar copolymer is obtained by reacting with glycidyl methacrylate. Copolymerization is usually carried out in a solvent using a polymerization initiator. As a polymerization initiator, for example, Z, 2 oxime diisobutyronitrile or the like can be used. 2,2,- azobis(2-mercaptopropionate methyl ester) helium gas) sulfonium compound, peroxymethyl sulfhydryl group or peroxidized tert-butyl peroxide. > The granules can be used as long as it is to dissolve the monomer ginseng p "early body", for example: ethylene glycol monomethyl ether acetate, B-reserved B-Israel ethyl ether acetic acid wheel, C-B Ethyl esters, propylene glycols, diols such as ethyl acetate, and the solvents exemplified as the following solvents (Ε). The polymerization initiator is considered for the lower reaction temperature. It is also possible to determine the enthalpy of the monomer (4). The 4th agent and the other can also use the compound having the arm group ^ ^ * 0 group to change the side chain of the copolymer obtained by the above formula (8). It can also be used as a catalyst for the detection of a photosensitive resin. The addition of a contact for introducing a polymerizable group into a resin can be used as a catalyst. For example, it can be listed as a mu. i465JJ.doc -24- 201037458 Additive for the reaction of the field 1J. As an additive, for example, the following copolymers [K1] to [K4] [κι] unsaturated unsaturated acid and/or unsaturated acid-lowering liver (8)) (Hereinafter, it may be simply referred to as "(Bl)"), and a monomer having a group having a ring (4) having a carbon number of 2 to 4 (Β2) (hereinafter, Referred to only as Γ (Β2) ") polymerization of the copolymer.

[Κ2] A copolymer obtained by polymerizing (Bl), (Β2) and a monomer (Β3). Here, the monomer (Β3) (hereinafter, simply referred to as "(By") is a monomer copolymerizable with (Β1) and/or (Β2), and is not (Β1) and/or (Β2)) [0] In the copolymer of (Ugly 1) and (83), one part of the carboxyl group derived from (81) and the cyclic ether derived from (Β2) having a carbon number of 2 to 4 are used. Copolymer obtained by the reaction of the base. [Κ4] (共聚物1) and (Β3) copolymer.

Further, it may be added to prevent, for example, hydroquinone. As the alkali-soluble resin (B), and the like. Among them, a copolymer obtained by polymerizing at least (Β1) and (Β2) is preferred. Examples of (Β1) include an aliphatic unsaturated carboxylic acid and/or an aliphatic unsaturated carboxylic anhydride. Specific examples thereof include: unsaturated monocarboxylic acids such as acrylic acid, methacrylic acid, and crotonic acid; maleic acid, fumaric acid, citraconic acid, mesaconic acid, itaconic acid, and 3-vinyl phthalic acid. Dicapric acid, 4-vinyl phthalic acid, 3,4,5,6-tetrahydrophthalic acid, 1,2,3,6-tetrahydrophthalic acid, dimercaptotetrahydroortho Unsaturated dicarboxylic acids such as benzoic acid and 1,4-cyclohexene dicarboxylic acid; methyl-5-norbornene-2,3-didecanoic acid, 5-carboxybicyclo[2.2.1]g- 2-ene, 146511.doc -25· 201037458 Hg H 5-carboxy-5-ethylbicyclo[2.2.lm_2_^,%-viable i-methylbicyclo[2.2.^-2-ene, 5_rebel-6 _ethylbicyclo[2 21]heptane-2_ quinone-containing bicyclic unsaturated compounds; cis-butamic acid liver, tonic anhydride, itaconic acid H ethylene phthalate liver, 4-B Dilute phthalic acid liver, 3,4,5,6-tetrahydrophthalic anhydride, 1,2,3,6-tetrahydrophthalic anhydride, dimethyltetrahydro-o-p-dicarboxylic acid = , 5,6-di-re- bisbicyclo[2·2·μ_2,^ (bicycloheptylenedicarboxylate) oxime unsaturated dicarboxylic acid anhydride; succinic acid mono[2_(methyl) propylene oxiranyloxyethyl ], Dibasic ortho-acidic monounsaturated mono[(indenyl) propylene oxyalkyl] esters such as benzoic acid mono [2-(methyl) styrene oxyethyl] vinegar; α-( An unsaturated acrylate such as hydroxymethyl)acrylic acid or the like. κ soil and carboxyl group Among them, olefinic acid, methacrylic acid or maleic anhydride is preferred in terms of copolymerization reactivity and alkali solubility. , use alone or in combination of two or more. Furthermore: in the monthly book: the knives and agents exemplified can be used alone or in combination as long as they are not specified in advance. And (4) as long as it has, for example, a body selected from the group consisting of carbon (e.g., an ethylene oxide group, an oxetan group, and a tetrahydrogen group) = at least one of the groups. Further, it is preferably a single having an unsaturated bond as (B2), for example, a monomer having a oxiranyl group, having 1465 II.d〇, * 26 - 201037458 oxetan Monomer, monomer having tetrahydrofuranyl group, and the like. The monomer having an oxirane group is a polymerizable compound having, for example, one selected from the group consisting of an aliphatic oxirane group and an alicyclic oxirane group. The monomer having an oxiranyl group is preferably a compound having a group of an ethane group and an alicyclic oxirane group and having an unsaturated bond, and more preferably And a right, a monomer having a sulfonium ethane group and a (fluorenyl) acryloxy group. Ο The term "aliphatic oxirane group" means a structure in which an aliphatic olefin is epoxidized. Examples of the compound having an aliphatic epoxy group include polyglycidyl (meth)acrylate, (meth)acrylic acid _β_mercapto-shrinking oil vinegar, and (mercapto)acrylic acid _β. _Ethyl glycidol vinegar, glycidyl ethyl ether, a compound represented by (VI), etc., as described in Japanese Laid-Open Patent Publication No. Hei 7-248625. work

In the case of the above-mentioned formula (VI), the compound represented by the above formula (VI) is, for example, an alkenylbenzyl group. Glycidol _, sputum A χ W @ vinyl fluorenyl glycidyl ether, glycerol oxime for vinyl soil, α methyl _ ethene thiol glycidol test, 146511.doc •27· 201037458 曱基-间Vinyl benzyl glycidyl sulphate, .^,, α τ 暴 - p-vinylbenzyl glycidyl hydrazine, 2,3- diglycidoxy methoxy, its basic ethylene, 2,4- diglycidyloxy f group Styrene, 2,5-di% oxime, glycidyloxyf-styrene' diglycidyloxyf-phenylbenzene 2,3,4-diglycidyloxy f oxime vinyl, 2,3,5 - triglycidoxy pimple, pore 丞 r basic ethylene, 2,3,6-triglycidyl fluorenyl F styrene, 3,4 5 bis, glyceroloxyf styrene, 4 , 6_ diglycidyloxy P-styrene, and the like. The alicyclic oxiranyl group means a structure. θ oxidizes the ruthenium (4) as a monomer of a monomeric aliphatic monocyclic epoxy group having an alicyclic epoxy group, and the star has a ruthenium For the time being, there is an early body 4 of the polycyclic epoxy B. The so-called aliphatic body, the Shanghai and the ancient collection "s early nuclear type ~ rolling ethane base single Ί, there will be early ring of aliphatic thin smoke epoxy compound. Further, the term "polyorganic polyorganism" refers to a monovalent compound having a polycyclic aliphatic group which is a radical. The bismuth of the structure formed by the epoxidation of a monomeric hydrocarbon having an oxirane group has an alicyclic olefin and an unsaturated bond, and has an alicyclic hydrocarbon compound. Epoxidized to be a compound, a preferred olefin group-based compound, Q冓, and having a (subunit) propylene as the above-mentioned monocyclic aliphatic olefin, such as hexene, cycloglycol, cyclo-invigorating, etc. ,, 歹^ lifting: cyclopentanol, ring compound. It is preferred that the carbon number is 5~7

As a monomer having an aliphatic monocyclic ring I 70 group, it can be listed as specifically 146511.doc -28- 201037458: vinylcyclohexene oxide (1,2-epoxy-4-vinylcyclohexane) (e.g., Celloxide 2000; manufactured by Daicel Chemical Industries, Inc.), 3,4-epoxycyclohexyl methacrylate (e.g., 匸丫(;1〇11^八400; manufactured by Daicel Chemical Industries, Inc.), 3,4-epoxycyclohexyl methacrylate (for example, Cyclomer Ml00; manufactured by Daicel-Chemical Industries Co., Ltd.), etc. Examples of the polycyclic aliphatic olefin include dicyclopentene and bicyclo Terpene, norbornene, isodecene, bicyclooctene 'bicyclononene, biguanide undecene, tricycloundecene, bicyclododecene, tricyclododecene, etc. Among them, better The compound having a carbon number of 8 to 12. As the monomer having an aliphatic polycyclic oxirane group, for example, acrylic acid _3,4_epoxy-p-butyl ester, methacrylic acid _3, 4 _ epoxy decyl ester, a compound represented by formula (vii) and represented by formula (νιπ) And the like. Mouth ❹ r71o

R^O I II H2C=C—C~〇—X?2 (vm)

In the formula (VII) and the formula (vm), each independently represents a hydrogen atom or an alkyl group which may be substituted with a hydroxyl group and has a carbon number of 丨4. X7丨 and X72 respectively represent a single bond, the carbon number is an alkanediyl group or an * integer, and t represents an integer of 0 to 6; wherein, the letter 6; * indicates the relationship with the 〇 as R71 and R72, specifically No. and shop v calendar J enumerated. 虱 atom; methyl, ethyl, n-propyl, isopropyl, n-butyl, t-butyl, t-butyl and the like alkyl; 146511.doc -29- 201037458 Methyl, 1-hydroxyethyl, 2-hydroxyethyl, hydroxypropyl, 2-hydroxypropyl, 3-hydroxypropyl, 1, hydroxy-1-methylethyl, 2-hydroxy-i-A A hydroxy-substituted alkyl group such as a ethyl group, a 1-hydroxybutyl group, a 2-hydroxybutyl group, a 3-hydroxybutyl group, or a 4-hydroxybutyl group. More preferably, it is a hydrogen atom, a methyl group, a methyl group, a methyl group, a 2-ethyl group. More preferred are hydrogen atoms and methyl groups. Specific examples of the alkanediyl group having a carbon number of i to 6 include a single bond; an anthracene group, an exoethyl group, a 1,2-propanediyl group, an i'3-propyldiyl group, a 14-butylene group, and a - pentoyl, 1,6-hexanediyl. Among them, preferred are a single bond, a methylene group, an extended ethyl group, _〇_CH2_, and -〇_(CH2)2-. Even better is the single key ' -0-(CH2)2-. The at least one compound selected from the group consisting of the compound represented by the formula (VII) and the compound represented by the formula (VIII) is preferably selected from the group consisting of the compound represented by the following formula (VII'). At least one compound selected from the group consisting of compounds represented by the formula (¥111,). R71.0

Strictly H2C=C-c~〇 (VIII*)

In the formulae (VII,) and (VIIr), the same meaning as in R72. R71' and R72' each represent a compound represented by the formula (VII) and the above-mentioned R71, and examples thereof include a compound represented by the formula (10) and a formula. Preferably, it is a formula (purchasing), a formula (VII-3), a formula (purchasing), a formula (VII_7), and a formula (v is a formula (VIM1) to a formula (VI1·15). More preferably, the formula (VIM) ), formula (melon 7), formula (VII_9), formula 14651I.doc 30· 201037458 (VII-15) ❹ h2c=ch-co—ch2' H2C=CH-G—O—C2h4 Hfi O—C^4- 0

(Vl·?) 0 II H2C-CH»C-0—C2Hi-S CHpH 〇(VII-11) Hfi=l ——ϊ„0 CH3O I II h2c=c—c—o—ch2 H2c—c—coc ^4·

C2H5O HjC^C—CO H2C=CH—C "*TM· O—CH3O / ii H2C=C—C—〇—C2H4-S CH3〇I il HH 2〇——C—〇—G.2 Ht— M.

CH3o / li H2C=C*—C—0—Q2H4—〇

C2H4OH ο I II HgC =C-0-0 (vm〇)

The compound represented by the formula (VIII) includes, for example, a compound represented by the formula (VIII- 〇 I) to the formula (VIII-15). Preferred are formula (VIII-1), formula (VIII-3), formula (VIII-5), formula (VIII-7), formula (VIII-9), formula (VIII-II) to formula (VIII- 15). More preferred are formula (VIII-1), formula (VIII-7), formula (VIII-9), formula (VIII-15). 0

(vm-2) 1! h2c:ch-c a 0—C2Kt a s· 0 \\ Η h2c=ch-c—o—c2h*

-31 146511.doc 201037458

The compound represented by the formula (VII) and the compound represented by the formula (VIII) can be used singly. Also, it can be mixed at any ratio. In the case of mixing, the mixing ratio thereof is in a molar ratio, preferably a formula (VII): Formula (VIII) is 5: 95 to 95: 5, more preferably 10: 90 to 90: 10 And even better is 20: 80-80: 20. The above-mentioned monomer having an oxetane group means, for example, a polymerizable compound having an oxacyclobutane group. The monomer having an oxetane group is preferably a compound having an oxetanyl group and having an unsaturated bond, more preferably having an oxetanyl group and a (meth) acryloxy group. Monomer. Specific examples of the monomer having an oxetane group include 3-methyl-3-mercaptopropenyloxyindenyloxybutane and 3-methyl-3-propenyloxymethyl group. Oxetane, 3-ethyl-3-methylpropenyloxymethyloxetane, 3-ethyl-3-propenyloxymethyloxetane, 3-mercapto 3-methylpropenyloxyethyloxetane, 3-methyl-3-propenyloxyethyloxetane, 3-ethyl-3-mercaptopropenyloxy B Oxycyclobutane or 3-146511.doc -32- 201037458 Ethyl-3-propenyloxyethyloxetane and the like. The above-mentioned monomer having a tetrahydrocinchyl group means, for example, a tetrahydrobite group-polymerizable compound. Has tetrahydrogen. The monomer of the fluoromethyl group is preferably a compound having a tetrahydrofuranyl group and having an unsaturated bond, more preferably a monomer having a tetrahydrofuranyl group and a (meth)acryloxy group. Specific examples of the monomer having a tetrahydrofuran group include tetrahydrofurfuryl acrylate (for example, Viscoat V#150, manufactured by Osaka Organic Chemical Industry Co., Ltd.), tetrahydrofurfuryl methacrylate, and the like. Examples of the copolymerizable monomer (B3) include methyl (meth) acrylate, ethyl (meth) acrylate, n-butyl (meth) acrylate, and second butyl (meth) acrylate. (meth)acrylic acid alkyl esters such as (butyl) (meth)acrylate; cyclohexyl (meth)acrylate, 2-methylcyclohexyl (meth)acrylate, (meth)acrylic acid Ring [5.2.1 · 02'6] decane-8-yl ester (in the technical field, as a customary name, called dicyclopentyl (meth) acrylate), dicyclopentyl (meth) acrylate (meth)acrylic acid cyclic alkyl ester such as ethyl ethyl acrylate or isobutyl (meth) acrylate; aryl (meth) acrylate such as phenyl (meth) acrylate or benzyl (meth) acrylate; Dicarboxylic acid diethyl ester, diethyl fumarate, itaconic acid di-S-dicarboxylic acid diester; (meth)acrylic acid hydroxyethyl ester, (meth)acrylic acid 2-hydroxyl Hydroxyalkyl esters such as propyl ester; bicyclo [2.2.1] hept-2-ene, 5-methylbicyclo [2.2.1] hept-2-ene, 5-ethyl 146511.doc -33- 201037458 bicyclo [ 2.2.1] Hept-2-ene 5-hydroxybicyclo[2.2.1]hept-2-ene, 5-hydroxymethylbicyclo[2.2.1]hept-2-ene, 5-(2'-hydroxyethyl)bicyclo[2.2.1]heptane- 2-ene, 5-methoxybicyclo[2.2.1]hept-2-ene, 5-ethoxybicyclo[2.2.1]hept-2-ene, 5,6-dihydroxybicyclo[2.2.1] Hept-2-ene, 5,6-di(hydroxymethyl)bicyclo[2.2.1]hept-2-ene, 5,6-bis(2'-hydroxyethyl)bicyclo[2.2.1]hept-2 - alkene, 5,6-dimethoxybicyclo[2_2.1]hept-2-ene, 5,6-diethoxybicyclo R.2.1]hept-2-ene, 5-hydroxy-5-methyl Bicyclo[2.2.1]hept-2-ene, 5-hydroxy-5-ethylbicyclo[2.2.1]hept-2-ene, 5-hydroxyindolyl-5-indenylbicyclo[2·2·1] Hept-2-ene, 5-tert-butoxycarbonylbicyclo[2 2 1; 1 hept-2-ene, 5-hexyloxycarbonylbicyclo[2_2.1]hept-2-ene, 5-phenoxy Carbonyl bicyclo[2_2·1]hept-2-ene, 5,6-bis(t-butoxycarbonyl)bicyclo[2 2 1]hept-2-yl di-(J hexyloxy)bicyclo[2.2. 1] Heptene-2-divalent bicyclic unsaturated compounds; N methyl cis-butyl diimide, N-ethyl maleimide, N-propyl maleimide, etc. -alkyl maleimide; ^cyclopentyl cis-butadiene , N•cyclohexyl maleimide, N-cyclooctylmethyleneimine, etc., such as sulfonium butadiene: quinone imine; Jingang J Hyun, maleimide, N_ Substituting U-crosslinked carbocyclic groups such as ruthenium sulphate and n-imine, succinimide, N-phenyl succinimide, etc. N-arylalkyl succinimide, N-aryl succinimide, N-butyl sulphonimide, N-butyl succinimide, 3 , N_ Dingdi-i-iminyl-4 -) spray ding secret _ peach core olefin imidate butyrate, N_ butyl quinone imine _6_ cis-butane yummy face 3 said & Known as hexanoic acid, Ν-butyl diimide imino group _3_simene hydrazine 146511.doc -34- 201037458 imidate propionate, Ν-(9· acridinyl) maleimide, etc. Dicarbonyl ruthenium derivatives; m-methylstyrene, p-methylphenyl

Styrene, α-methylstyrene, alkene, vinyl nitrile, ethylene ethylene, vinylidene chloride, vinyl acetate, 1,3-butadiene, isoolefin, and the like. Among them, in terms of copolymerization reactivity and alkali solubility, benzene*, fluorene-cyclohexylmethanedibutylene bicyclo[2.2.1]hept-2-ene and the like are preferable. Ethyl hydrazine, hydrazine-phenyl cis-butyl diimide, hydrazine-benzyl butyl nitrene, and negative copolymer [Κ1]~[Κ4], for example, the "Experimental method for polymer synthesis" (The method described in the above document, and the cited documents described in the literature) was produced by the method described in the publication of the first edition of the Chemicals Co., Ltd., the first edition of the chemistry. Specifically, the monomers (Β1) and (Β2) constituting the copolymer, any specific amount of (Β3), a polymerization initiator, and a solvent are added to the reaction vessel, and oxygen is replaced by nitrogen in the absence of oxygen. Under the conditions, stirring, heating, and heat preservation were carried out, whereby a polymer was obtained. The polymerization conditions such as the addition method, the reaction temperature and the time can be appropriately adjusted in consideration of the heat generation amount of the polymerization equipment. Here, any of the polymerization initiators and solvents to be used may be generally used in the field. For example, the following polymerization initiators, solvents and the like can be used. Furthermore, the obtained copolymer can be directly used as a solution after the reaction, or 146511.doc •35· 201037458 can be used to concentrate or dilute the cold liquid of $, ☆, A » m, and can also use a method such as reprecipitation. And take out the solid (powder). In particular, in the case of this polymerization, the following solvent is used as a solvent, whereby the solution after the reaction can be used as it is, and the production steps can be simplified. Copolymerization, [Μ is preferably a ratio of the monomers to the total number of moles of the precursors constituting the copolymer [Κ1], in the range of the molar fraction (Β1) 5 to 95 mol% 10~ 50 moles. /〇; (Β2) 5~95 mol% 50~90 mol%. More preferably, it is 10 to 90 mol%, and further preferably more preferably 10 to 90 mol%, and even more preferably, 'copolymer [Κ2] is preferably a ratio of each monomer to The total number of moles of the monomers constituting the copolymer [Κ2] is in the following range. (Β1) 2 to 40 mol%, more preferably 5 to 35 mol% (Β2) 2 to 95 mol%, and more preferably 5 to 8 m.乂 (Β3) 1 to 65% by mole, more preferably 1 to 60% by mole. The copolymer [Κ3] can be produced in two stages. In the same manner as the above method, the copolymer was obtained by copolymerizing (Β1) and (8). . . In this case, it is preferred that the total number of moles of each monomer relative to the monomers constituting the resin is in the following range. (Β1) 5 to 50 mol%, preferably 1 to 45 mol% (Β3) 50 to 95 mol%, preferably 55 to 90 mol%. Then, one part of the carboxylic acid and/or carboxylic acid 146511.doc •36· 201037458 anhydride derived from the copolymer of (Β 1) and it & () and the ethylene oxide derived from (B2) The reaction is carried out by a group, an oxetane group or a tetrahydrofuranyl group. To this end, the atmosphere in the flask is replaced with air from nitrogen, and (B2), a reaction catalyst, a polymerization inhibitor, and the like are added to the flask, for example, 6 Torr to 13 Torr. [Next, the reaction is continued for 1 to 10 hours. The reaction conditions such as the method, the reaction temperature and the time can be appropriately adjusted in consideration of the production equipment and the calorific value of the polymerization, etc. In this case, the number of moles of (B2) is relatively better than that of (B1). The ear %, more preferably 15~ = the reaction catalyst is preferably used, for example, as a reaction catalyst for (iv) with an epoxy group, an oxetan group or a tetrahydroindolyl group. The amount of the reaction catalyst to be used is, for example, about 0.001 to 5% by mass based on the total amount of (Βι) to (B3). The polymerization inhibitor can be exemplified, for example. Hydroquinone. The amount of Ο & inhibitor used can be exemplified, for example, with respect to (B1) to (B3).

The measurement is about 0.001 to 5% by mass. The D copolymer [K4] preferably has a ratio of the respective monomers in the following range with respect to the total number of moles of the monomers constituting the copolymer [K4]. (B1) 2 to 40 mol%, more preferably 5 to 35 mol% (d) (10) ~ (four) ear ^ is better with (9) moir. /. . = The weight average molecular weight of the polystyrene oxide of [K1HK4] is 疋3, _~1〇〇,000, more preferably 5, _~50,000. The copolymer is called [K4] dispersion (molecular weight distribution), [weight average score 146511.doc -37-201037458 sub-quantity (Mw) / number average molecular weight (Mn)] is preferably 丨丨~6 〇, better The polystyrene-equivalent weight average molecular weight of the 1.2~4·0 〇 test soluble resin (Β) is 5,000~35, 0〇〇' is preferably 6,000~3〇, 〇〇〇, particularly good is 7,000~ 28,000. When the molecular weight is in the above range, the coating film = degree is increased, the residual film ratio is also high, the solubility of the unexposed portion to the developer is good, and the resolution tends to be increased, which is preferable. The alkali-soluble resin (Β) has an acid value of 50 to 150, preferably 6 to 135, particularly preferably 70 to 135. Here, the acid value is a value obtained by neutralizing the amount (mg) of potassium hydroxide required for the test resin (10), and can be determined by titration using an aqueous solution of potassium oxynitride. The content of the test-soluble resin (8) is 7 to 65 mass%, preferably 13 to 6 mass%, more preferably 17 to 55 mm%, based on the solid content of the colored photosensitive resin composition. When the content of the secret resin (8) is in the above range, there is a tendency to be visible, and the resolution and the residual film ratio tend to increase, which is preferable. The colored photosensitive resin composition of the present invention contains a photopolymerizable compound, and the polymerizable compound (C) is an activity which can be produced from the photopolymerization initiator (D) by irradiation of light, and, The compound which polymerizes a base, an acid, etc. is not specifically limited. For example, a compound of a saturated bond or the like. The carbon-carbon which is a compound is not used as the photopolymerizable compound, and the light-polymerizable compound of the above-mentioned base is preferably a trifunctional or higher group. The photopolymerizable compound, for example, a polyfunctional group having a ruthenium of three or more functional groups: pentaerythritol tetraacrylic acid 146511.doc -38. 201037458 vinegar, pentaerythritol tetramethyl acrylate vinegar, dipentaerythritol propylene vinegar, two Pentaerythritol pentamethacrylate, dipentaerythritol hexaacrylate vine, bis-pentaerythritol hexamethyl acrylate acid s. These photopolymerizable compounds (6) may be used singly or in combination of two or more. The content of the photopolymerizable compound (C) is preferably from 7 to 65% by mass, more preferably from 13 to 6 % by mass, based on the solid content of the colored photosensitive resin composition, and more preferably 1 7 to 17 5 5 temporarily I. / . 疋 / quantity / 0. When the content of the photopolymerizable compound Ο ❹ (C) is within the above range, the curing is sufficiently caused, the film thickness ratio before and after the development is increased, and the undercut is formed in the pattern, and the adhesion becomes Good tendencies, so it is better. The colored photosensitive resin composition of the present invention contains a photopolymerization initiator (D). The photopolymerization initiator (D) may, for example, be an active radical generator acid generator. The living radical generating agent generates active radicals by irradiating light. X, an acid generator generates an acid by irradiating light. Examples of the living radical generating agent include a #ethyl residual compound, a feminine compound, a benzophenone compound, a 9-oxygen sulfide compound, a tri-till compound, and an anthraquinone compound. The above-mentioned ethyl ketone-based compound may, for example, be diethyl cyproterone, 2-methyl-2 morphinyl + (4 - methylthioalkyl) propyl group = 2, 2 Methylamino-H4 linalylphenyl)_2_pyristyl butyl sulfonium, 2_ carbyl-2-methyl-1-phenylpropanone, benzoin quinone ketone, 2 hydroxy-methyl Base 1 [4 (2 & ethoxy) phenyl] propyl hydride _, i via cyclohexyl phenyl hydrazine, 146511.doc -39- 201037458 oligomer, etc., preferably exemplified by 2 methyl Marlene-1-(4-methylsulfanyl-propyl)propan-1-one and the like. Examples of the benzoin-based compound include benzoin, benzoin methyl bond, benzoin ethyl light, benzoin isopropyl mystery, and benzoin thioether. 〃 As the above-mentioned diphenylmethyl group-based compound, for example, benzophenone, o-benzhydrylbenzoic acid methyl vinegar, 4 phenyl dimercapto ketone, and benzalkonyl methyl group-based cornerstone may be mentioned. Key, 3,3.,4,4.-four ("second τ~ «· - (dibutylperoxycarbonyl)benzophenone, 2,4,6-trimethyldiphenyl A ketone or the like. Examples of the above-mentioned oxysulfuric acid (tetra)-based compound include: isopropyl -9-oxo-anging star, 4-isopropyloxanthine f, and 2,4-diethyl-9-oxygen. Sulfur 4-spot star '2,4-dichlorooxo-oxygen sulphate ♦ star, n4_propoxy oxo-oxygen sulphate, etc. As the above-mentioned two-tillage-based compound, for example, 2,4_bis (trioxan) )-6-(4-methoxyphenyl...~well, 2,4, bis(trichloromethyl:6:(4-methoxynaphthyl)-1,3,5-three wells, 2,4 - bis(trichloromethyl)_6_(4_f oxystyrene HW·three _, 2,4 bis(trichloromethyl)_6_[2_(5_ fluorenyl-2-yl) vinyl ^,3,5-three tillage, 2,4_bis(trichloroindenyl)_6_[2_(biting-2-yl)vinyl]-1,3,5-three-spray, 2,4-double (three Chlorine f-based)_6_[2_(4_diethylamino-2-mercaptophenyl)ethenyl hydrazine, 3,5_three tillage, 2 4-double ( Gas methyl 6-[2-(3,4-dimethoxyphenyl)vinyl puss, etc. As the above-mentioned quinone-based compound, for example, a fluorenyl-fluorenyl compound can be mentioned, and specific examples thereof include :N_Stupidyloxy_M4_phenylsulfanylphenyl)butan-1-one-2-imine, N-stupyloxy-丨_(4-phenylsulfanylbenzene Octyl-1-keto-2-imine, N-hexyloxy_M9_ethyl_6_(2_methyl 146511.doc -40- 201037458 benzoyl)-9H-carbazole- 3-yl]ethane-1_imine, N-acetoxyloxy[9_ethylmethyl-4·(3,3-dimethyl-2,4-dioxolylmethoxy) Benzyl fluorenyl}·9Η-carbazole-3-yl]ethane-1-imine, etc. Further, as the living radical generating agent, for example, 2,4,6-trimethylbenzhydryl group can be used. Diphenylphosphine oxide, 2,2·-bis(o-phenyl)_4,4,5,51-tetraphenyl'yl-1,2'-biimidazole, 1〇_butyl_2_gas Pyridone, 2-ethylhydrazine, benzyl, 9,10-phenanthrenequinone, camphorquinone, methyl phenylglyoxylate, titanocene compound, etc. ° Ο Ah As the above acid generator, for example, 4-hydroxyphenyldimethylhydrazine p-toluene acid salt, 4-phenylphenyl group Methyl town hexahydrate, 4_acetoxyphenyl dimethyl quinone p-toluene sulfonate, 4 acetoxyphenyl methyl hexyl hexafluoroantimonate, triphenyl sulfonium P-toluenesulfonate, triphenylsulfonium hexamethylate, diphenylphosphonium p-toluate, diphenyl iron hexahydrate, rust salts, nitrobenzyl tosylate, Benzoin benzoate and the like. Further, in the compound described above as the above-mentioned living radical generating agent, a compound which generates an acid at the same time as the active radical is also present, and for example, a sigma-based photopolymerization initiator can also be used as the acid generator. Light gathering. The content of the initiator (D) is preferably 〇1 to 3〇% by mass, more preferably 1 to 2-0, based on the total of the alkali-soluble resin (B) and the photopolymerization port (c). quality%. When the content of the photopolymerization initiator is in the above range, high sensitivity can be achieved, exposure time can be shortened, and productivity can be improved, so that the car is good. The coloring photosensitive resin composition of the moon may further contain photopolymerization 146511.doc -41 - 201037458 and a starting assistant (9). The photopolymerization initiation aid (G) is a compound which is usually used in combination with the photopolymerization initiator (9) to promote polymerization of a photopolymerizable compound which starts polymerization by a photopolymerization initiator. The photopolymerization initiation aid (6) may, for example, be an amine compound, a oxo oxime compound or a 9-oxo sulfur P hawthorn compound. Examples of the above amine-based compound include triethanolamine, methyldiethanolamine, triisopropanolamine, 4-dimethylaminopyridinium benzoate, and 4-didecylaminobenzoic acid ethyl H-methylamine. Benzocarboxylic acid dispersant, benzoic acid - 2**-methylamino group B, methyl a ^ a τ 妆 makeup base formic acid 2, ethylhexyl ester, hydrazine, hydrazine-dimercapto-p-aniline, 4,4ι_bis(dimethylamino)diphenyl hydrazine is commonly known as micbutazone), 4,4, bis(diethylamino)benzophenone, 4,4|bis (ethyl ketone) Aminoamino)benzophenone and the like, among which 4,4,-bis(diethylamino)benzophenone is preferred. Examples of the above alkyl fluorenyl compound are, for example, 9 1 decyl fluorenyl fluorene, 2-ethyl -9,10-dimethoxy fluorene ' 9, 1 fluorene, diethoxy fluorene, 2 _ Ethyl 9,10-monoethoxy hydrazine, 9,10-dibutoxy fluorene, 2 ethyl -9, fluorenyl dibutoxy fluorene, and the like. Examples of the above-mentioned 9-oxothiopurine galaline compound include 2-isopropyl-5-oxathioindole 4_isopropyl-9-oxathione, 2,4, and diethyl_9. _ oxopurine, 2,4-dichloro-9-oxothiopurine, 1-chloropropoxy -9-oxathiazide and the like. The photopolymerization initiation aid (G) may be used singly or in combination of two or more kinds as a photopolymerization initiation aid (G), or a commercially available one as a commercially available photopolymerization starter. (G), for example, the product name "εαβ_F" (manufactured by Hosei Chemical Industry Co., Ltd.). 146511.doc -42- 201037458 The photopolymerization initiation composition in the colored photosensitive resin composition of the present invention is a combination of (D) and a photopolymerization initiation assistant (G), for example, diethoxy Acetophenone/4,4·-bis(diethylamino)benzophenone, 2-mercapto-2-morphinyl-1 1-(4-mercaptosulfanylphenyl)propane-1- Ketone/4,4'-bis(diethylamino)benzhydryl-, 2-carbyl-2-mercapto-1-phenylpropanone-1·one/4,4,_bis (diethyl) Amino group) ^ 曱酉 、 笨 笨 笨 笨 笨 笨 笨 4 4 4 4 4 4 4 4 4 4 4 4 4 4 4 4 4 4 4 4 4 4 4 4 4 4 4 4 4 4 4 4 4 4 4 4 4 4 4 4 4 4 4 4 4 4 4 4 4 4 4 4 4 4 4 Phenyl]propane_丨-ketone/4,4'-bis(diethylamino)benzophenone, hydroxycyclohexyl phenyl ketone ί ® bis(diethylamino)benzophenone, 2 -Hydroxy-2-indenyl_ι_[4-(1-methylvinyl)phenyl]propan-1-one oligomer/4,4,-bis(diethylamino)benzophenone, 2-benzyl-2-didecylamino"-(decalmorpholinylphenyl)butane-indole-ketone/4,4-bis(diethylamino)benzophenone, etc. Methylmorpholinyl-1-(4-methylsulfanylphenyl)propan-1-one/4,4,-bis ( Ethylamino)diphenyl fluorenone. When the photopolymerization initiation aid (G) is used, it is preferably used in an amount of phase Q per 1 mole of photopolymerization initiator (D). The solvent (Ε) contained in the colored photosensitive resin composition of the present invention is not particularly limited, and can be used in the field, and is usually used in the field. The solvent to be used, for example, an ester (a solvent containing _c〇〇_), an ether other than an ester (a solvent contained therein), a ketone other than an ester (a solvent containing -CO-), and an alcohol: The aromatic hydrocarbons, guanamines, N-methylpyrrolidone, dimethyl sulfoxide, and the like are selected and used. Examples of the esters include decyl lactate, ethyl lactate, and milk 146511.doc. -43- 201037458 Butyl acrylate, 2-methylisobutyrate, ethyl acetate, n-butyl acetate, isobutyl acetate, amyl acetate, isoamyl acetate, butyl propionate, butyrate Propyl ester, ethyl butyrate, butyl butyrate, methyl oxyacetate, cesium oxyacetate s-blend, ethyl methoxyacetate, butyl methoxyacetate, ethoxyacetate Ethyl acetate, ethyl ethoxyacetate, decyl 3-methoxypropionate, ethyl 3-methoxypropionate, methyl 3-ethoxypropionate, ethyl 3-ethoxypropionate, 2 _Methoxypropionic acid methyl vinegar, 2-methoxyoxypropionic acid ethyl ester, 2- methoxy propionate propyl ester, 2 ethoxy propionate methyl ester, 2-ethoxypropionic acid ethyl ester, 2_ Methyl methoxy-2-propenylpropionate, ethyl 2-ethoxy-2-methylpropionate, methyl pyruvate, ethyl pyruvate, propyl pyruvate, methyl ethyl acetate, B Ethyl acetate, methyl 2-oxo-butyrate, ethyl 2-oxobutanoate, _3_methoxybutyl acetate, -3-methyl-3-decyloxybutyl acetate, cyclohexane Alcohol acetate, γ-butyrolactone and the like. Examples of the ethers include ethylene glycol monodecyl ether, ethylene glycol monoethyl ether, ethylene glycol monopropyl ether, ethylene glycol monobutyl ether, and diethylene glycol early methyl ether. Diethylene glycol monoethyl ether, diethylene glycol monobutyl ether, propane di, monomethyl _, propylene glycol monoethyl ether, propylene glycol monopropyl test, propylene glycol monobutyl ether, 3 · decyloxy Alcohol, 3-methoxy-3-butanol, tetrahydrofuran, tetrahydropyran, dioxane, i-ethylene glycol dimethyl ether, diethylene glycol diethyl ether, diethylene glycol fluorenyl Ethyl ether, diethylene glycol-propyl ether, diethylene glycol dibutyl ether, propylene glycol monodecyl ether acetate, propanol early ethyl acetate, and - 妒留工坡 ^ 〇d Affinity, monopropyl ether acetate, ethylene glycol monomethyl mycohol acetate, 7 # 曰I - alcohol early ethyl ether acetate, diethylene glycol monoethyl hydrazine acetate, -7 — jr^rt»g — B — 転 early butyl ether acetate, anisole, phenethyl ether, methyl benzophenone _ and the like. 146511.doc -44· 201037458 As the above ketones, examples of ketone, acetone, 2-butanone, 2_ ° List: 4_hydroxy-4-methyl-2-pentyl

^ 3PJ Λ Ο Α. X ketone, cyclopentanone, cyclohexyl _, isophora _, etc., 4 · heptanone, 4 methyl-2-pentane as the above alcohols 'e.g., alcohol, hexanol, Cyclohexanol, B·A#, B%, propanol, and D. are used as the above-mentioned propylene glycol, glycerin, and the like.卜q work back to the aromatic hydrocarbons benzene, 1,3,5-trimethylbenzene and the like. For example, benzene and toluene' are used as the above guanamines, and Ψ Ν Ν - m m m m m m m m m m m m m m m m m m m m m m m m m m m m m m m m m m m , team methyl bad ketone and so on. The #solvent may be used alone or in combination of two or more. Among them, the preferred one is a 3-hydroxyl solvent containing anthraquinone. Examples of the hydroxyl group-containing solvent include milk - « » - hydrazine, ethyl lactate, butyl lactate, 2-hydroxy hydrazine, 4 - thiol + methyl - 2. pentane. The content of the solvent (8) in the photosensitive resin composition is 95% by mass, more preferably 75 to 92% by mass based on the coloring photosensitive resin composition. The content of the solvent (8) is adjusted so that the amount of the solid matter is from 8 to 25% by mass, preferably from 8 to 25% by mass, based on the color of the photosensitive resin composition. When the content of the solvent (8) is in the above range, the flatness at the time of (4) is good, and when the color is (4), the color density is not insufficient, so that the display characteristics are good, which is preferable. The surfactant (F) contained in the colored photosensitive composition of the present invention is suitably a surfactant having a fluorine atom or a cerium atom. Further, at least 1 146511.doc - 45 - 201037458 selected from the group consisting of a polyoxo-based surfactant, a gas-based surfactant, and a polyoxo-based surfactant having a fluorine atom may be mentioned. The above-mentioned polyoxo-based surfactant may, for example, be an surfactant having a ruthenium oxygen bond. Specific examples include: Toray Silicone DC3PA, Toray Silicone SH7PA, Toray Silicone DC11PA, Toray Silicone SH21PA 'Toray Silicone SH28PA, Toray Silicone SH29PA, Toray Silicone SH30PA, Polyether Modified Emu Oil SH8400 (trade name: Toray Silicone; Dow Corning Toray Limited Manufactured by the company), 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) Made by the Japan subsidiary). The fluorine-based surfactant may, for example, be an interface active agent having a fluorocarbon chain. Specific examples include Fluorad (trade name) FC430, Fluorad FC43 1 (manufactured by Sumitomo 3M Co., Ltd.); Megafac (trade name) F142D, Megafac F171, Megafac F172, Megafac F173 ' Megafac F177, Megafac F183, Megafac F489, Megafac F554 , Megafac R30 (manufactured by DIC Corporation); Eftop (trade name) EF301, Eftop EF303, Eftop EF351, Eftop EF352 (manufactured by Mitsubishi Materials Electronic Chemicals Co., Ltd.); Surflon (trade name) S381, Surflon S382, Surflon SC101, Surflon SC105 (manufactured by Asahi Glass Co., Ltd.); E5844 (manufactured by Daikin Fine Chemical Co., Ltd.); BM-1000, BM-1100 (all manufactured by BM Chemie) 146511.doc -46· 201037458 etc. . The polyfluorene-based surfactant having a fluorine atom may, for example, be a surfactant having a cerium oxygen bond or a fluorocarbon chain. Specific examples include Megafac (registered trademark) R08, Megafac BL2, Mgafac, Megafac F477, Megafac F443 (manufactured by DIC Corporation), and the like. These surfactants may be used singly or in combination of two or more. The content of the surfactant (F) is preferably 0.0005 to 0.3 parts by mass, more preferably 5% by weight, based on 1 part by mass of the colored photosensitive resin composition. When the content of the surfactant (F) is in this range, flatness tends to be good, which is preferable. The colored photosensitive resin composition of the present invention is preferably a negatively colored photosensitive resin composition. The colored photosensitive resin composition of the present invention can be preferably used for forming a color filter or a colored pattern, and can obtain a color pattern and a color filter excellent in color density, brightness, contrast, sensitivity, resolution, heat resistance, and the like. . Further, the color-sensitive photosensitive resin composition of the present invention can be used for preparing an optical film, an array substrate, or the like which is a part of a constituent part of a light-receiving sheet or a color pattern, and the like. Display devices such as a color filter or a coloring film, an optical film, or an array substrate, for example, a known liquid crystal display device, an organic EL (electroluminescence) device, a solid-state imaging device, and the like, all of which are related to a color image. device. As a method of forming a color filter or a pattern thereof using the colored photosensitive resin composition of the present invention, for example, the colored photosensitive resin composition of the present invention is applied to a substrate or another resin layer (for example, formed in advance) 146511.doc •47· 201037458 On the other colored photosensitive resin composition layer on the substrate, etc.), the volatile component such as the bath is removed/dried to form a colored layer, and the colored layer is exposed to light through the photomask and then developed. Method; a method of using an inkjet apparatus without photolithography, and the like. The film thickness of the coating film is not particularly limited, and may be appropriately adjusted depending on the materials and applications used, for example, G.1 to 30 _about 2 is preferably 1 to 20, or so. More preferably, it is about 1 to 6 μm. Examples of the coating method of the photosensitive resin composition include extrusion coating method, direct gravure coating coating, reverse gravure coating method, and CAP (calcium ph〇sphate, phosphoric acid). Calcium) coating method, die coating method, and the like. Further, a dipping coater, a bar coater, a rotary coater, a slit & a rotary coater' slit coater (sometimes also called a die coater (4) e coater may be used. ), a coating machine such as a curtain flat coater (cunain fl〇wc〇a called 'spin丨ess c〇ater) is applied. Among them, it is preferred to apply using a spin coater. Examples of the solvent removal/drying include natural drying, air drying, reduction, drying, and the like. The specific heating temperature is preferably 1 G to about 2, preferably 25 to 1 Torr. (: Left and right. The heating time is suitable for about 1 〜 to ~ 6 〇 minutes, preferably from 30 seconds to 30 minutes. Decompression drying is exemplified as two "

Under the pressure of Pa, take 2〇~25. (: The temperature range is left and right. The colored photosensitive resin composition of the present invention can be preferably used for forming a colored image of a color filter used for forming a liquid crystal display element or a solid-state image sensor. Example 146511 .doc 48. 201037458 Hereinafter, the colored photosensitive resin composition and the color filter of the present invention will be described in more detail by way of examples. In the examples, "%" and "parts" are not described in detail. (%) and mass parts. Synthesis Example 1: Synthesis of Dye Α1 〇In a flask equipped with a cooling tube and a stirring device, 15 parts of a pigment (manufactured by SEM), 15 parts of chloroform and a team were placed in a flask equipped with a cooling tube and a stirring device. 8_9 parts of ice dimethyl decylamine, and the surface was maintained at (10) or less under the scramble, and 10.9 parts of sulphur sulphate chloride was added dropwise. After the completion of the dropwise addition, the temperature was raised to 5 Torr., and maintained at the same temperature for 5 hours. The reaction was cooled to 2 generations. The surface of the reaction solution after cooling was maintained at 2 (TC or less, and the surface of the solution was added dropwise with 125 parts of 2-ethylhexylamine and 22.1 parts of diethylamine. Mixture. After the pot, knowing, and then Stirring at the same temperature for 5 hours to carry out the reaction 'then' using a rotary evaporator, the solvent mixture of the obtained reaction mixture was removed, and a small amount of formazan and hydrazine (tetra) were added. The mixture was added to ion-exchanged water 375 parts. The mixed liquid is stirred and crystallized. The crystals of the precipitated Γ® are separated by filtration, carefully washed with ion-exchanged water, and decompressed at 6 〇t • Deadly to obtain dye A1 (dye A1-1~ Mixed dye of dye A1-8) u A0-1 Η

Ho3s·^

At

146511.doc -49 201037458 (in equation (A1),

Rc independently represents -S02NH-Ra, -S03H, -S03· or -Η; Ra Table 7F 2-ethylhexyl)

A1,3 Α1-Δ,

A1_S A1-6

Ra = 乂 乂 VIII / Synthesis Example 2 - Synthesis of Resin B 1 Into a flask equipped with a stirrer, a thermometer, a reflux cooling tube 'dropper funnel and a nitrogen fluoride introduction tube, 210 g of propylene glycol monomethyl ether acetate was introduced, and 堍After the environment of the bottle is replaced with nitrogen by air, the temperature is raised to 10 ° C, and the following solution is added dropwise, that is, containing benzyl methacrylate 70·5 g (0 40 mol), methyl propyl benzoic acid 43.0 g(G.5 mol), tricyclic sulphuric acid skeleton, single f-based propionic acid vinegar (manufactured by Hitachi Chemical Co., Ltd., FA_513M) 22 〇g(〇i〇莫耳) and propylene glycol monomethyl ether acetate vinegar To the mixture of 215 g was added a solution of U,-azo 146511.doc -50-201037458 diisobutyronitrile 3.6 g, and stirring was continued at 100 °C. Then, the atmosphere in the flask was replaced with air from nitrogen, and 35.5 g of glycidyl methacrylate [0.25 mol (50 mol% relative to the carboxyl group of the methacrylic acid used in the reaction) was introduced into the flask] , tris-dimethylaminomethylphenol 0.9 § and hydroquinone 0.145 §, at 110 ° (: continuous reaction, from which a solid acid value of 79 mg KOH / g of resin solution B1 was obtained. The weight average molecular weight in terms of polystyrene measured by GPC (gel-permeation chromatography) is Ο 3.0×104. The measurement of the polystyrene-equivalent weight average molecular weight of the above resin is carried out by the GPC method under the following conditions. Device: HLC-8120GPC (manufactured by Tosoh Co., Ltd.) Column: TSK-GELG2000HXL Column temperature: 40. Solvent 〇 " : THF (tetrahydrofuran, tetrahydrofuran) Flow rate: 1 · 0 mL / min Solid concentration of the test solution: 0.001 to 0.01 mass 0 / 〇. Injection amount: 50 μίν Detector: RI calibration standard substance: TSK STANDARD POLYSTYRENE F- 40, F-4, Fl, A-2500, A-500 Example 1 (Tosoh shares Manufactured by Ltd.) 146511.doc -51 - 201037458 [Preparation of coloring photosensitive resin composition 1] (A-2) Pigment: CI Pigment Blue 15 : 6 3.0 parts of acrylic pigment dispersant 1 · 〇 propylene glycol monoterpene 23 parts of the ether ether acetate were mixed, and the pigment was sufficiently dispersed using a bead mill, and then (A-1) dye: dye A1 0.5 part (B) Resin: resin solution B1 16 parts (C) Photopolymerizable compound Dipentaerythritol hexaacrylate (KAYARAD DPHA; manufactured by Nippon Kayaku Co., Ltd.) 4·6 parts (D) Photopolymerization initiator: OXE-01 (manufactured by Ciba Japan) 1.4 parts (E) Solvent: 4-hydroxy- 4-Mercapto-2-pentanone 51 parts (F) Surfactant: Polyether modified polyxanthene oil (SH8400, manufactured by Dow Corning Toray Co., Ltd.) 0.0005 parts were mixed to obtain a colored photosensitive resin composition 1 [Formation of Coating Film for Evaluation] A colored photosensitive resin composition was applied onto a glass substrate (Eagle 2000; manufactured by Corning Co., Ltd.) of 3 inches by spin coating, followed by a clean oven at 1 Torr. Pre-bake for 3 minutes at 〇 ° C. After cooling, use an exposure machine (TME-1) 5 0RSK (manufactured by Topcon Co., Ltd.) was irradiated with light at an exposure amount of 1,500 mJ/cm 2 (365 nm) in an atmosphere, and heated at 220 ° C for 20 minutes to prepare a coating film for evaluation. The film thickness of the coating film 146511.doc -52 - 201037458 was measured using a film thickness measuring device (DEKTAK3; manufactured by Nippon Vacuum Technology Co., Ltd.), and the result was 2.8 μm. [Evaluation of Flatness] The surface of the obtained coating film was visually confirmed. The results are shown in Table 3. [Brightness Evaluation] Using a color measuring machine (OSP-SP-200; manufactured by Olympus Co., Ltd.), the coating film on the obtained glass substrate was subjected to spectrometry, and a C light source was used to measure CIE (Commission International de I'Eclairage, Xy chromaticity coordinates (bx, By) and brightness in the XYZ color system of the International Commission on Illumination. The results are shown in Table 3. In the same manner as in Example 丨, the colored photosensitive resin compositions 2 and 3 were obtained in the same manner as in Example 〜, except that the number of parts shown in Table j was changed to the coloring photosensitive resin composition i. . Further, in the same manner as in Example 制作, the production and evaluation of the coating film for evaluation were carried out. The results are shown in Table 3. [Table 1] Example 2 Example 3 (F) 0.01 0.1 Example 4 制备 [Preparation of color photosensitive resin composition 4] 3.0 parts 1 · 〇 part 23 parts 〇. 5 parts of (A_2) pigment: CI Pigment Blue 15 : 6 Acrylic pigment dispersant propylene glycol monomethyl ether acetate is mixed, using a bead mill to fully disperse the pigment and then '(A-1) dye: dye VIII 1 146511.doc -53- 201037458 ( B) Resin: Resin solution B1 16 parts (C) Photopolymerizable compound: dipentaerythritol hexaacrylate (KAYARAD DPHA; manufactured by Sakamoto Chemical Co., Ltd.) 4.6 parts (D) Photopolymerization initiator: OXE-01 ( (manufactured by Ciba Japan) 1.4 parts (E) Solvent: 4-hydroxy-4-methyl-2-pentanone 5 1 part (F) Surfactant: Megafac F554 (manufactured by DIC Corporation) 〇.〇〇3 parts The mixture was mixed to obtain a colored photosensitive resin composition 4. [Evaluation] The production and evaluation of the coating film for evaluation were carried out in the same manner as in Example 1. The results are shown in Table 3. In the colored photosensitive resin composition 4, the components (B) to (F) were changed to the number of parts in Table 2, except that the coloring photosensitive sample was obtained in the same manner as in Example 4. A coating resin composition for evaluation was used. Further, it was produced and evaluated in the same manner as in Example 4. The results are shown in Table 3 [Table 2] Example 5: Parts) Silk 丨6 (B) 16 ___ 15 (C) 4.6 __ 4 5 (9) 1.4 1 7 (E) 51 ----- υ (F) 0.01 η 1 ---------- 146511.doc -54- 201037458 [Table 3] Content of surfactant (F) Flatness Bx By Brightness Example 1 0.0005 parts 〇 0.141 0.071 7.4 Implementation Example 2 0.010 parts 〇0.141 0.071 7.3 Example 3 0.100 parts 〇0.142 0.068 6.8 Example 4 0.003 parts 〇0.141 0.069 7.0 Example 5 0.010 parts 〇0.141 0.071 7.4 Example 6 0.300 parts 〇0.141 0.070 7.1 Furthermore, in Table 3 The content of the surfactant indicates the content of 100 parts by mass based on the coloring photosensitive resin composition. In Examples 1 to 6, a coating film having no unevenness in flatness was obtained, and excellent brightness was confirmed. Industrial Applicability According to the present invention, it is possible to provide a colored photosensitive resin composition which provides a coating film having high brightness and excellent flatness and a color filter. 146 146511.doc 55-

Claims (1)

201037458 VII. Patent Application Range: 1. A colored photosensitive resin composition comprising: a coloring agent (A), an alkali-soluble resin (B), a photopolymerizable compound (c), a photopolymerization initiator (D), a solvent (E) and a surfactant (F>, and the colorant (A) comprises both a dye (A-1) and a pigment (A-2) containing a compound represented by the formula (1), a surfactant (F) is a surfactant having a fluorine atom and/or a ruthenium atom, The content of the surfactant (F) in 100 parts by mass of the coloring photosensitive resin composition is 0 〇〇〇 5 parts by mass or more and 〇 3 parts by mass or less; RR independently represents a hydrogen atom, -R6 or a monovalent aromatic hydrocarbon group having a carbon number of 6 to 10, and a hydrogen atom contained in an aromatic hydrocarbon group having a carbon number of 6 to 1 Å may pass through a crypto atom, _R6, - 〇H, -〇R6, -so3·, -so3h, _so3m, c〇jH, -C〇2R6, _s〇3r64_s〇2N(r8)r9 are substituted; R is not ·δ〇3, -s〇3H, -so3M, -co2H, -co2R6, -S〇3R6 or -S02N(R8)R9; the table is not an integer of 0 to 5; when m is an integer of 2 or more, plural R5s may be the same or different; X represents a dentate atom; a represents an integer of ruthenium or osmium; 146511.doc 201037458 R6 represents a monovalent saturated hydrocarbon group having a carbon number of 1 to 10; the hydrogen atom contained in the saturated hydrocarbon group having a carbon number of 1 to (7) may be The aryl group or the carbon number is substituted with the alkoxy group of (7); the saturated hydrocarbon group having a carbon number of 1 to 10 may be substituted by -Ο-, -CO- or -NR7-; 2 R7 represents the carbon number The Hd is saturated with a nicotine group; the hydrogen atom contained in the saturated hydrocarbon group having a carbon number of w〇 may be substituted with a (tetra) atom or an alkoxy group having a carbon number of (4); R8 and R9 each independently represent a hydrogen atom and have a carbon number of Bu 〇 〇 burning base, carbon number is 3~3 0 ring cyclosyl or _Q; or r\r9 may also be bonded to each other to form a heterocyclic ring having a carbon number of H0; the alkyl group and the hydrogen atom contained in the cycloalkyl group may pass through an atom of an atom, _〇 Substituting H, _Q, _c ', V LH2 or ~CH=CHR6, the alkyl group and the _CH2mc〇_, _NH- or -Nr6- contained in the cyclization group are substituted; the carbon number is 1 to 10 The chowder is replaced by & people, υ (the hydrogen atom contained in the miscellaneous mother can be replaced by ϋ, -Η or -Q; 芳 = carbon number 6 to 10 (4) fragrant smoke base or 5~10 members The monovalent primary hetero group of the ring 'the aromatic hydrocarbon group and the wind atom contained in the aromatic heterocyclic group may pass through a south atom, .CH=Pu . ' "〇R ' -N〇2 'CH2 or _CH=CHR_6 is substituted; Μ represents a sodium atom or a potassium atom; the same; in the composition of the compound represented by the formula (1), the charge number and the charge number phase 2. The dye (the content of the dye (Α_υ) and the pigment (4) The ratio of 3 ® is 1: 99 to 99 : 1. 146511.doc 201037458 • The composition of the item 1 wherein the pigment (Α·2) contains CI·Pigment Blue 15: pigment. a composition in which a solvent (Ε) is a hydroxyl group containing i The solvent agent. 5. 6. 8.9. A coloring scheme is formed using a composition as claimed. A color filter comprising a colored pattern as claimed in claim 5. A color filter of claim 6, which is formed by photolithography. - Thin" which includes the color filter, light sheet as in claim 6. ^ 用途 The use of the composition of the keeper 1 is used to make color filters 146511.doc 201037458 IV. Designated representative map: (1) The representative representative of the case is: (none) (2) The symbol of the 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: 146511.doc