CN104714366A - Colored curable resin composition - Google Patents

Colored curable resin composition Download PDF

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Publication number
CN104714366A
CN104714366A CN201410777700.1A CN201410777700A CN104714366A CN 104714366 A CN104714366 A CN 104714366A CN 201410777700 A CN201410777700 A CN 201410777700A CN 104714366 A CN104714366 A CN 104714366A
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Prior art keywords
methyl
formula
represent
resin composition
curable resin
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CN201410777700.1A
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CN104714366B (en
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芦田彻
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Dongwoo Fine Chem Co Ltd
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Sumitomo Chemical Co Ltd
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    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/0005—Production of optical devices or components in so far as characterised by the lithographic processes or materials used therefor
    • G03F7/0007—Filters, e.g. additive colour filters; Components for display devices
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/004—Photosensitive materials
    • G03F7/0045—Photosensitive materials with organic non-macromolecular light-sensitive compounds not otherwise provided for, e.g. dissolution inhibitors
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/004—Photosensitive materials
    • G03F7/027—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds

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  • Physics & Mathematics (AREA)
  • General Physics & Mathematics (AREA)
  • Spectroscopy & Molecular Physics (AREA)
  • Materials For Photolithography (AREA)
  • Optical Filters (AREA)
  • Compositions Of Macromolecular Compounds (AREA)
  • Polymerisation Methods In General (AREA)

Abstract

The invention provides a colored curable resin composition including colorants A, resin B, photo-polymerized compounds C and photo-polymerized initiators D of compounds represented in a formula I. In the formula I of X-Y+ (I), X- represent negative ions from a dye, Y+ represents positive ions of compounds represented in a formula Y. In the formula Y as described in the specification, n represents an integer from 1 to 8, and R40 represents an alkyl groups with the carbon number of from 1 to 4.

Description

Colored curable resin composition
Technical field
The present invention relates to a kind of colored curable resin composition.
Background technology
Colored curable resin composition is used in the manufacture of the color filter used in the display device such as liquid crystal indicator, el display device, plasma scope.As colored curable resin composition, record the colored curable resin composition (Japanese Unexamined Patent Publication 2013-7032) comprising following compound.
Summary of the invention
The invention provides following [1] ~ [7].
[1] colored curable resin composition, it contains:
Comprise the colorant (A) of the compound represented with formula (I),
Resin (B),
Photopolymerizable compound (C) and
Photoepolymerizationinitiater initiater (D).
X -Y +(I)
[in formula (I), X -represent the negative ion coming from dyestuff, Y +represent the kation coming from the compound represented with formula (Y).
(in formula (Y), n represents the integer of 1 ~ 8, R 40represent the alkyl of carbon number 1 ~ 4.)]
[2] according to the colored curable resin composition recorded in [1], wherein, the negative ion coming from dyestuff is the negative ion come from containing golden azo dyes or triarylmethane dye.
[3] according to the colored curable resin composition recorded in [1] or [2], wherein, the negative ion coming from dyestuff comes from the negative ion containing golden azo dyes.
[4] according to the colored curable resin composition recorded in [2] or [3], wherein, the negative ion come from containing golden azo dyes represents with formula (A0).
[in formula (A0), R 1~ R 18represent the alkyl of 1 valency of hydrogen atom, halogen atom, carbon number 1 ~ 10, nitro or-SO independently of one another 2r 29.
R 29represent-OH ,-NHR 30or-R 32.
R 30the alkyl representing 1 valency of hydrogen atom, carbon number 1 ~ 10, the cyclohexyl ,-R that can be replaced by the alkyl of carbon number 1 ~ 4 31-O-R 33,-R 34-CO-O-R 35,-R 36-O-CO-R 37, or the aralkyl of carbon number 7 ~ 10.
R 31, R 34and R 36represent the alkylidene of the divalent of carbon number 1 ~ 8 independently of one another.
R 32, R 33, R 35and R 37represent the alkyl of 1 valency of carbon number 1 ~ 8 independently of one another.
R 19and R 20represent hydrogen atom, methyl, ethyl or amino independently of one another.
M 1represent Cr or Co.]
[5] colored curable resin composition recorded any one of [1] ~ [4], wherein, colorant (A) is also containing pigment.
[6] color filter, it utilizes the colored curable resin composition recorded any one of [1] ~ [5] to be formed.
[7] display device, the color filter recorded during it comprises [6].
According to colored curable resin composition of the present invention, the color filter of excellent heat resistance can be obtained.
Embodiment
Colored curable resin composition of the present invention contains:
Comprise the compound represented with formula (I) (to be sometimes also denoted as below " compound (I) ".) colorant (A),
Resin (B),
Photopolymerizable compound (C) and
Photoepolymerizationinitiater initiater (D).
X -Y +(I)
In formula (I), X -represent the negative ion coming from dyestuff,
Y +represent the kation coming from the compound represented with formula (Y).
In formula (Y), n represents the integer of 1 ~ 8, R 40represent the alkyl of carbon number 1 ~ 4.
As dyestuff, can enumerate containing golden azo dyes, triarylmethane dye, Xanthene dyes and cyanine dye, wherein, preferably containing golden azo dyes and triarylmethane dye, more preferably containing golden azo dyes.
As the negative ion come from containing golden azo dyes, the negative ion coming from following direct yellow 112 or Blue VRS 58, the negative ion etc. represented with following formula (A0) can be enumerated.
Coming from the middle of the negative ion containing golden azo dyes, preferably with the negative ion that formula (A0) represents.
In formula (A0), R 1~ R 18represent the alkyl of 1 valency of hydrogen atom, halogen atom, carbon number 1 ~ 10, nitro or-SO independently of one another 2r 29.
R 29represent-OH ,-NHR 30or-R 32.
R 30the alkyl representing 1 valency of hydrogen atom, carbon number 1 ~ 10, the cyclohexyl ,-R that can be replaced by the alkyl of carbon number 1 ~ 4 31-O-R 33,-R 34-CO-O-R 35,-R 36-O-CO-R 37, or the aralkyl of carbon number 7 ~ 10.
R 31, R 34and R 36represent the alkylidene of the divalent of carbon number 1 ~ 8 independently of one another.
R 32, R 33, R 35and R 37represent the alkyl of 1 valency of carbon number 1 ~ 8 independently of one another.
R 19and R 20represent hydrogen atom, methyl, ethyl or amino independently of one another.
M 1represent Cr or Co.
In formula (A0), as the alkyl of 1 valency of carbon number 1 ~ 10, methyl, ethyl, n-pro-pyl, isopropyl, normal-butyl, sec-butyl, the tert-butyl group, n-pentyl, n-hexyl, n-heptyl, n-octyl, decyl, 1-methyl butyl, 1 can be enumerated, 1,3,3-tetramethyl butyl, 1,5-dimethylhexanyl, 1,6-dimethyl heptyl, 2-ethylhexyl and 1,1,5,5-tetramethylhexyl etc.
As the alkyl of carbon number 1 ~ 4, methyl, ethyl, n-pro-pyl, isopropyl, normal-butyl, sec-butyl, the tert-butyl group etc. can be enumerated.
As the aralkyl of carbon number 7 ~ 10, phenyl methyl, phenylethyl, phenyl propyl etc. can be enumerated.
As the alkylidene of the divalent of carbon number 1 ~ 8, methylene, ethylidene, propane-1,3-bis-base, propane-1,2-bis-base, butane-1 can be enumerated, 4-bis-base, butane-1,3-bis-base, pentane-1,5-bis-base, hexane-1,6-bis-base, heptane-1,7-bis-base, octane-1,8-bis-base etc.
As the alkyl of 1 valency of carbon number 1 ~ 8, methyl, ethyl, n-pro-pyl, isopropyl, normal-butyl, sec-butyl, the tert-butyl group, n-pentyl, n-hexyl, n-heptyl, n-octyl etc. can be enumerated.
As halogen atom, fluorine atom, chlorine atom, bromine atoms, atomic iodine can be enumerated, wherein preferred fluorine atom and chlorine atom.
As the alkyl of 1 valency of carbon number 1 ~ 10, preferable methyl, ethyl, n-pro-pyl, isopropyl, normal-butyl, sec-butyl, the tert-butyl group.
As-SO 2r 29, can enumerate with-SO 3the sulfonic group that H represents, with-SO 2nHR 30represent group, with-SO 2r 32the group represented.
As with R 30the alkyl of 1 valency of the carbon number 1 ~ 10 represented, the alkyl of 1 valency of the carbon numbers 1 ~ 4 such as preferable methyl, ethyl, n-pro-pyl, isopropyl, normal-butyl, sec-butyl, the tert-butyl group.
As the cyclohexyl that can be replaced by the alkyl of carbon number 1 ~ 4, cyclohexyl, 2-methylcyclohexyl, 2-ethylcyclohexyl, 2-propylcyclohexyl, 2-isopropylcyclohexyl-, 2-butylcyclohexyl, 4-methylcyclohexyl, 4-ethylcyclohexyl, 4-propylcyclohexyl, 4-isopropylcyclohexyl-, 4-butylcyclohexyl etc. can be enumerated, preferably there is the cyclohexyl of the alkyl of carbon number 1 ~ 4, more preferably 2-methylcyclohexyl at 2.
As-R 31-O-R 33methoxy, ethoxyl methyl, propoxy methyl, methoxy ethyl, ethoxyethyl group, Among, methoxy-propyl, ethoxycarbonyl propyl, propoxypropyl, 2-oxo-4-methoxybutyl, octyloxy propyl group, 3-ethoxycarbonyl propyl, 3-(2-ethyl hexyl oxy) propyl group etc. can be enumerated, preferably (C1-C4 alkoxy) methyl, more preferably methoxy and ethoxyl methyl.
As-R 34-CO-O-R 35methoxycarbonylmethyl, dion e, ethoxy carbonyl methyl, ethoxycarbonylethyl group, propoxycarbonyl methyl, propoxycarbonylethyl, butoxy carbonyl methyl, butoxy carbonyl ethyl etc. can be enumerated, preferred Methoxycarbonylmethyl or dion e.
As-R 36-O-CO-R 37acetoxy-methyl, Acetoxvethyl, ethylcarbonyl group oxygen ylmethyl, ethylcarbonyl group oxygen base ethyl, propyl group carbonyloxymethyl, propyl group ketonic oxygen base ethyl, butyl carbonyloxymethyl, butyl ketonic oxygen base ethyl etc. can be enumerated, preferred acetoxy-methyl and Acetoxvethyl.
As R 30, preferred hydrogen atom.
As with-SO 2nHR 30the group represented, can enumerate N-Methylsulfamoyl, N-ethylsulfamovl, N-propylsulfamov, N-isopropylsulfamoyl base, N-Butylsulfamoyl base, N-isobutyl sulfamoyl, N-sec-butyl sulfamoyl, N-tert-butyl group sulfamoyl, N-amyl group sulfamoyl, N-(1-ethyl propyl) sulfamoyl, N-(1,1-dimethyl propyl) sulfamoyl, N-(1,2-dimethyl propyl) sulfamoyl, N-(2,2-dimethyl propyl) sulfamoyl, N-(1-methyl butyl) sulfamoyl, N-(2-methyl butyl) sulfamoyl, N-(3-methyl butyl) sulfamoyl, N-Cyclopentylsulfamoyl base, N-hexyl sulfamoyl, N-(1,3-dimethylbutyl) sulfamoyl, N-(3,3-dimethylbutyl) sulfamoyl, N-heptyl sulfamoyl, N-(1-methylhexyl) sulfamoyl, N-(Isosorbide-5-Nitrae-dimethyl amyl group) sulfamoyl, N-octyl group sulfamoyl, N-(2-ethylhexyl) sulfamoyl, N-(1,5-dimethyl) hexyl sulfamoyl, N-(1,1,2,2-tetramethyl butyl) sulfamoyl, the sulfamoyl that N-allyl sulfamoyl etc. be instead of by aliphatic alkyl,
N-(2-methoxy ethyl) sulfamoyl, N-(2-ethoxyethyl group) sulfamoyl, N-(1-methoxy-propyl) sulfamoyl, N-(3-methoxy-propyl) sulfamoyl, N-(3-ethoxycarbonyl propyl) sulfamoyl, N-(3-propoxypropyl) sulfamoyl, N-(3-isopropoxide propyl) sulfamoyl, N-(3-own oxygen base propyl group) sulfamoyl, N-(2-ethyl hexyl oxy propyl group) sulfamoyl, N-(3-tert-butoxy propyl group) sulfamoyl, N-(4-octyloxy butyl) sulfamoyls etc. are by-R 31-O-R 33the sulfamoyl that instead of,
N-(Methoxycarbonylmethyl) sulfamoyl, N-(dion e) sulfamoyl, N-(ethoxy carbonyl methyl) sulfamoyl, N-(ethoxycarbonylethyl group) sulfamoyl, N-(propoxycarbonyl methyl) sulfamoyl, N-(propoxycarbonylethyl) sulfamoyl, N-(butoxy carbonyl methyl) sulfamoyl, N-(butoxy carbonyl ethyl) sulfamoyl etc. are by-R 34-CO-O-R 35the sulfamoyl that instead of;
N-(acetoxy-methyl) sulfamoyl, N-(Acetoxvethyl) sulfamoyl, N-(ethylcarbonyl group oxygen ylmethyl) sulfamoyl, N-(ethylcarbonyl group oxygen base ethyl) sulfamoyl, N-(propyl group carbonyloxymethyl) sulfamoyl, N-(propyl group ketonic oxygen base ethyl) sulfamoyl, N-(butyl carbonyloxymethyl) sulfamoyl, N-(butyl ketonic oxygen base ethyl) sulfamoyl etc. are by-R 36-O-CO-R 37the sulfamoyl that instead of;
N-cyclohexylsulfamoyl, N-(2-methylcyclohexyl) sulfamoyl, N-(3-methylcyclohexyl) sulfamoyl, N-(4-methylcyclohexyl) sulfamoyl, N-(4-butylcyclohexyl) sulfamoyl etc. are by the sulfamoyl having substituent cyclohexyl and instead of;
The sulfamoyl etc. that N-benzyl sulfamoyl, N-(1-phenylethyl) sulfamoyl, N-(2-phenylethyl) sulfamoyl, N-(3-phenyl propyl) sulfamoyl, N-(4-phenyl butyl) sulfamoyl, N-[2-(2-naphthyl) ethyl] sulfamoyl, N-[2-(4-aminomethyl phenyl) ethyl] sulfamoyl, N-(3-phenyl-1-propyl group) sulfamoyl, N-(3-phenyl-1-methyl-propyl) sulfamoyl etc. be instead of by aralkyl.
As-SO 2nHR 30, preferably-SO 2nH 2.
As-SO 2r 32methyl sulphonyl, ethylsulfonyl, sulfonyl propyl base, isopropelsulfonyl, normal-butyl sulfonyl, sec-butylsulfonyl, tert. butylsulfonyl, pentylsulfonyl, hexyl sulfonyl, heptyl sulfonyl, octyl group sulfonyl, 1-methyl butyl sulfonyl, 1 can be enumerated; 1; 3,3-tetramethyl butyl sulfonyl, 1,5-dimethylhexanyl sulfonyl, 1; 6-dimethyl heptyl sulfonyl, 2-ethylhexyl sulfonyl and 1; 1,5,5-tetramethylhexyl sulfonyl etc.Wherein, preferable methyl sulfonyl and ethylsulfonyl, more preferably methyl sulphonyl.
Owing to there being the trend that can form the more excellent pattern of thermotolerance etc., therefore preferred R 1~ R 18central at least 1 is nitro.
In addition, preferred R 1~ R 5at least 1 and R 6~ R 10central at least 1 is-SO 2r 29.There is multiple-SO 2r 29when, multiple R 29both can be the same or different.
As-SO 2r 29, preferably-SO 2r 32, more preferably methyl sulphonyl.
At the negative ion represented with formula (A0), there is-SO 2r 32when, more preferably R 11~ R 14at least 1 and R 15~ R 18central at least 1 is-SO 2r 32.There is multiple-SO 2r 32when, multiple R 32both can be the same or different.
As R 19and R 20, preferable methyl, ethyl and amino, more preferably methyl.
As the preferred example of the negative ion represented with formula (A0), the negative ion represented with formula (1-b1) ~ formula (1-b60) can be enumerated.
For the synthetic method of the negative ion represented with formula (A0), enumerate the negative ion represented with formula (A01) and be described.
(in formula, R 1~ R 5, R 11~ R 14, R 19, M 1represent the meaning identical with above-mentioned group.)
This negative ion can by making the compound represented with formula (d)
(in formula, R 1~ R 5, R 11~ R 14and R 19represent the meaning same as described above.) and chromium compound react in aqueous solvent (DMF, 1-METHYLPYRROLIDONE etc.), at 70 ~ 150 DEG C and manufacture for 3 ~ 10 hours.
As described chromium compound, chromic formate, chromium acetate, chromium chloride, charomic fluoride, chromium ammonium suplhate etc. can be enumerated, preferably enumerate chromic formate, chromium ammonium suplhate etc.
For the use amount of chromium compound, the compound represented with formula (d) relative to 1 mole, is preferably 0.5 ~ 1 mole.
The compound represented with formula (d) can by making the diazo salt that represents with formula (a2) and carrying out diazo coupling with the compound that formula (b1) represents in aqueous solvent and manufacture.
The diazo salt represented with formula (a2) such as can by carrying out diazotising by the amine nitrous acid, nitrite or the nitrites that represent with formula (a1) and obtaining.
[in formula (a1) and formula (a2), R 11~ R 14represent the meaning same as described above.A 1represent inorganic or organic anion.
In formula (b1), R 1~ R 4and R 19represent the meaning same as described above.]
As described inorganic anion, fluoride ion, chloride ion, bromide ion, iodide ion, high chloro acid ion, hypochlorite ion etc. can be enumerated.
As described organic anion, CH can be enumerated 3cOO -, PhCOO -deng.
As A 1, preferably enumerate chloride ion, bromide ion, CH 3cOO -deng.
In above-mentioned diazo coupling, temperature of reaction is preferably-5 DEG C ~ 60 DEG C, is more preferably 0 DEG C ~ 30 DEG C.Reaction time is preferably 1 hour ~ 12 hours, is more preferably 1 hour ~ 4 hours.As described aqueous solvent, 1-METHYLPYRROLIDONE etc. can be enumerated.
In order to promote this reaction, inorganic base can be made to coexist.
As described inorganic base, NaOH, calcium hydroxide, sodium carbonate, calcium carbonate, sodium acetate, calcium acetate etc. can be enumerated, preferably enumerate sodium carbonate, sodium acetate etc.
What is called comes from the negative ion of triarylmethane dye, is the negative ion having triarylmethane skeleton but also have the anion bases such as sulfonic group.
As the concrete example of negative ion coming from triarylmethane dye, the negative ion represented with formula (2-b1) ~ formula (2-b3) can be enumerated.
Xanthene dyes is the dyestuff in molecule with xanthene skeleton.
Cyanine dye is the dyestuff in molecule with cyanine skeleton.
Y in formula (I) +represent the kation coming from the compound represented with formula (Y).
N represents the integer of 1 ~ 8, R 40represent the alkyl of carbon number 1 ~ 4.
In formula (Y), n is preferably the integer of 1 ~ 3.As R 40, be preferably methyl and ethyl.
As the cationic concrete example coming from the compound represented with formula (Y), the kation represented with formula (3-b1) ~ formula (3-b9) can be enumerated.
As the compound represented with formula (I), compound preferably shown below.
Below, (below this compound is called by compound (I) to the compound represented with formula (I).) manufacture method be described.
As the manufacture method of compound (I), can by the salt of the negative ion with metal cation that come from dyestuff and mixing in a solvent with the compound that formula (Y) represents be manufactured.
The salt coming from the negative ion of dyestuff and metal cation can be medium and obtain by making dyestuff be dissolved in halid aqueous solution containing metal cation.
As the metal cation forming salt, the alkali metal cations such as lithium cation, sodium cation and potassium cationic can be enumerated.
As the compound represented with formula (Y), commercially available compound can be used.
As solvent, DMF, DMA, 1-METHYLPYRROLIDONE, dimethyl sulfoxide (DMSO), acetonitrile, ethyl acetate, toluene, methyl alcohol, ethanol, isopropyl alcohol, acetone, tetrahydrofuran, diox, water and chloroform can be enumerated.
Wherein, preferred DMF, DMA, 1-METHYLPYRROLIDONE, dimethyl sulfoxide (DMSO), methyl alcohol, ethanol, isopropyl alcohol and water.
When solvent is water, also the acid such as acetic acid, hydrochloric acid can be added.
The salt coming from the negative ion of dyestuff and metal cation is preferably 0 DEG C ~ 150 DEG C with the mixing temperature of the compound represented with formula (Y), is more preferably 10 DEG C ~ 120 DEG C, more preferably 20 DEG C ~ 100 DEG C.Incorporation time is preferably 1 hour ~ 72 hours, is more preferably 2 hours ~ 48 hours, more preferably 3 hours ~ 24 hours.
When employing the solvent molten with aqueous phase, can by the salt of the negative ion and metal cation that come from dyestuff, stir 1 ~ 3 hour more as required with the mixed solution of the compound represented with formula (Y), thereafter, utilization filtration obtains, and just the compound represented using formula (I) can be taken out as solid thus.
When employing the solvent immiscible with water, can to the salt of the negative ion and metal cation that come from dyestuff, with the reaction solution of the compound represented with formula (Y) in add water, crystal is separated out, thereafter filter, just the compound represented using formula (I) can be taken out as solid thus.
< colorant (A) >
Colorant (A) also can simultaneously also containing the dyestuff being different from compound (I).As this dyestuff, the dyestuffs such as oil-soluble dyes, acid dyes, the amine salt of acid dyes or the sulfamide derivative of acid dyes can be enumerated, such as, can enumerate compound, the middle known dyestuff recorded of dyestuff notes (Se Ran society) of being categorized as dyestuff by Colour Index (The Society of Dyers andColourists publishes).
Specifically, (following record of omitting C.I. solvent yellow, only records numbering can to enumerate C.I. solvent yellow 4.)、14、15、23、24、38、62、63、68、82、94、98、99、162；
C.I. solvent red 45,49,125,130;
C.I. solvent orange 2,7,11,15,26, the C.I. solvent dyes such as 56,
C.I. Indian yellow 1, 3, 7, 9, 11, 17, 23, 25, 29, 34, 36, 38, 40, 42, 54, 65, 72, 73, 76, 79, 98, 99, 111, 112, 113, 114, 116, 119, 123, 128, 134, 135, 138, 139, 140, 144, 150, 155, 157, 160, 161, 163, 168, 169, 172, 177, 178, 179, 184, 190, 193, 196, 197, 199, 202, 203, 204, 205, 207, 212, 214, 220, 221, 228, 230, 232, 235, 238, 240, 242, 243, 251,
C.I. azogeramine, 4, 8, 14, 17, 18, 26, 27, 29, 31, 34, 35, 37, 42, 44, 50, 51, 52, 57, 66, 73, 80, 87, 88, 91, 92, 94, 97, 103, 111, 114, 129, 133, 134, 138, 143, 145, 150, 151, 158, 176, 182, 183, 198, 206, 211, 215, 216, 217, 227, 228, 249, 252, 257, 258, 260, 261, 266, 268, 270, 274, 277, 280, 281, 195, 308, 312, 315, 316, 339, 341, 345, 346, 349, 382, 383, 394, 401, 412, 417, 418, 422, 426,
C.I. acid orange 6,7,8,10,12,26,50,51,52,56,62,63,64,74,75,94,95,107,108,169,173;
C.I. acid violet 6B, 7,9,17, the C.I. acid dyess such as 19,
C.I. direct Huang 2,33,34,35,38,39,43,47,50,54,58,68,69,70,71,86,93,94,95,98,102,108,109,129,136,138,141;
C.I. directly red 79,82,83,84,91,92,96,97,98,99,105,106,107,172,173,176,177,179,181,182,184,204,207,211,213,218,220,221,222,232,233,234,241,243,246,250;
C.I. direct orange 34,39,41,46,50,52,56,57,61,64,65,68,70,96,97,106,107;
C.I. directly the C.I. direct dyess such as purple 47,52,54,59,60,65,66,79,80,81,82,84,89,90,93,95,96,103,104,
C.I. mordant yellow 5,8,10,16,20,26,30,31,33,42,43,45,56,61,62,65;
C.I. mordant rouge 1,2,3,4,9,11,12,14,17,18,19,22,23,24,25,26,30,32,33,36,37,38,39,41,43,45,46,48,53,56,63,71,74,85,86,88,90,94,95;
C.I. mordant dyeing orange 3,4,5,8,12,13,14,20,21,23,24,28,29,32,34,35,36,37,42,43,47,48;
C.I. the C.I. mordant dye etc. such as mordant dyeing purple 1,2,4,5,7,14,22,24,30,31,32,37,40,41,44,45,47,48,53,58.
Colorant (A) also can also simultaneously containing pigment.
As pigment, can enumerate organic pigment, C.I. pigment violet 1,19,23,29,32,36, the violet pigments such as 38;
C.I. the yellow uitramarine such as pigment yellow 1,3,12,13,14,15,16,17,20,24,31,53,83,86,93,94,109,110,117,125,128,137,138,139,147,148,150,153,154,166,173,194,214;
C.I. pigment orange 13,31,36,38,40,42,43,51,55,59,61,64,65,71, the orange pigments such as 73;
C.I. Pigment Red 9,97,105,122,123,144,149,166,168,176,177,180,192,209,215,216,224,242,254,255,264, the red pigments etc. such as 265.
Wherein, preferably containing be selected from C.I. pigment yellow 13 8,139,150, in C.I. paratonere 177,242,254 at least a kind.By containing described pigment, easily realize the optimization of transmitted spectrum, resistance to chemical reagents becomes good.
These pigment both can be used alone, and also can be mixed with two or more.
Organic pigment also can implement rosin process as required, use imported the pigment derivative of acidic groups or basic group etc. surface treatment, the grafting process to surface of pigments by macromolecular compound etc., the micronize process by sulfuric acid particles method etc. or the cleaning treatment by the organic solvent for removing impurity or water etc., the ionic impurity by ion exchange process etc. removing process etc.
Organic pigment preferable particle size is even.By making it to carry out dispersion treatment containing pigment dispersing agent, dispersible pigment dispersion pigment being scattered in equably the state in solution just can be obtained.
As described pigment dispersing agent, the surfactants etc. such as kation system, negative ion system, nonionic system, both sexes, Polyester, polyamine system, acrylic acid series can be enumerated.These pigment dispersing agents both may be used singly or in combination of two or more.As pigment dispersing agent, represent with trade name and can enumerate KP (SHIN-ETSU HANTOTAI's chemical industry (strain) system), Florene (common prosperity society chemistry (strain) system), Solsperse (Zeneka (strain) system), EFKA (BASF AG's system), Ajisper (aginomoto Finetechno (strain) system), Disperbyk (BYK-Chemie Inc.) etc.
When using pigment dispersing agent, its use amount is preferably 100 quality % relative to pigment, is more preferably more than 5 quality % and below 50 quality %.If the use amount of pigment dispersing agent is in described scope, then there is the trend of the dispersible pigment dispersion that can obtain uniform disperse state.
The content of compound (I) is preferably 3 ~ 100 quality % relative to colorant (A), is more preferably 5 ~ 90 quality %, more preferably 10 ~ 80 quality %.
The content of colorant (A) is preferably 5 ~ 60 quality % relative to the solid constituent in colored curable resin composition, is more preferably 8 ~ 55 quality %, more preferably 10 ~ 50 quality %.Herein, so-called solid constituent, refers to the total of the composition except desolventizing in colored curable resin composition.If the content of colorant (A) is in described scope, then colour saturation when making color filter is abundant, and can contain the binder polymer of necessary amounts in the composition, therefore can form the enough patterns of physical strength.
< resin (B) >
Colored curable resin composition of the present invention contains resin (B).As resin (B), be not particularly limited, but be preferably alkali soluble resin.
As resin (B), such as, can enumerate following resin [K1] ~ [K4] etc.
[K1] has the cyclic ether structure of carbon number 2 ~ 4 and the monomer (a) (hereinafter sometimes referred to as " (a) ") of ethylenic unsaturated bond and is selected from the multipolymer of at least a kind (b) (hereinafter sometimes referred to as " (b) ") in unsaturated carboxylic acid and unsaturated carboxylic acid anhydrides.
[K2] (a) and (b) and can with the monomer (c) of (a) copolymerization (but, different from (a) and (b).) multipolymer of (hereinafter sometimes referred to as " (c) ")
The multipolymer of [K3] (b) and (c)
The resin that [K4] makes the copolymer reaction of (a) and (b) and (c) and obtain.
Comprise by resin (B) structural unit coming from (a), the reliability such as thermotolerance, resistance to chemical reagents of the colored pattern of gained can be improved thus further.
A () such as refers to the polymerizable compound of cyclic ether structure (being such as selected from least a kind in oxirane (oxirane) ring, oxetanes ring and tetrahydrofuran ring (oxolane ring)) and the ethylenic unsaturated bond with carbon number 2 ~ 4.A () preferably has the cyclic ether of carbon number 2 ~ 4 and the monomer of (methyl) acryloxy.
In this instructions, so-called " (methyl) acrylic acid ", represents at least a kind that is selected from acrylic acid and methacrylic acid.The statement such as " (methyl) acryloyl group " and " (methyl) acrylate " also has the identical meaning.
As (a), the monomer with oxirane base and ethylenic unsaturated bond, the monomer with oxetanyl and ethylenic unsaturated bond can be enumerated, there is the monomer etc. of tetrahydrofuran base and ethylenic unsaturated bond.
As (a), from the viewpoint of the reliability such as thermotolerance, resistance to chemical reagents that can improve the colored pattern of gained further, preferably there is the monomer of oxirane base and ethylenic unsaturated bond.
As (b), specifically, can enumerate acrylic acid, methacrylic acid, crotonic acid, neighbour, to unsaturated monocarboxylics such as vinyl benzoic acids;
Maleic acid, fumaric acid, citraconic acid, mesaconic acid, itaconic acid, 3-vinylphthalic acid, 4-vinylphthalic acid, 3,4,5,6-tetrahydrophthalic acid, 1,2, the unsaturated dicarboxylics such as 3,6-tetrahydrophthalic acid, dimethyl tetrahydro phthalic acid, Isosorbide-5-Nitrae-cyclohexene dicarboxylic acid;
Methyl-5-norborene-2, the dicyclo unsaturated compound containing carboxyl such as 3-dicarboxylic acid, 5-carboxyl dicyclo [2.2.1] hept-2-ene", 5,6-dicarboxyl dicyclo [2.2.1] hept-2-ene"s, 5-carboxyl-5-methyl bicycle [2.2.1] hept-2-ene", 5-carboxyl-5-ethyl dicyclo [2.2.1] hept-2-ene", 5-carboxyl-6-methyl bicycle [2.2.1] hept-2-ene", 5-carboxyl-6-ethyl dicyclo [2.2.1] hept-2-ene";
Maleic anhydride, citraconic anhydride, itaconic anhydride, 3-vinylphthalic acid acid anhydride, 4-vinylphthalic acid acid anhydride, 3,4,5,6-tetrabydrophthalic anhydride, 1,2,3,6-tetrabydrophthalic anhydride, dimethyl tetrahydro phthalic anhydride, 5, the unsaturated dicarboxylic class acid anhydrides such as 6-dicarboxyl dicyclo [2.2.1] hept-2-ene" acid anhydrides (carbic anhydride, Ha イ ミ Star ク Suan No water thing);
Unsaturated list ((methyl) acryloxyalkyl) ester of the polyprotonic acid of mono succinate (2-(methyl) acryloyl-oxyethyl) ester, phthalic acid list (2-(methyl) acryloyl-oxyethyl) ester etc. more than 2 yuan;
α-(hydroxymethyl) acrylic acid etc. contain the unsaturated acrylate etc. of hydroxyl and carboxyl in same a part.
As (b), consider in the aspect of copolyreaction, deliquescent aqueous alkali, preferred acrylic acid, methacrylic acid, maleic anhydride etc.
As (c), (methyl) methyl acrylate, (methyl) ethyl acrylate, (methyl) n-butyl acrylate, (methyl) sec-butyl acrylate, (methyl) tert-butyl acrylate, (methyl) 2-EHA, (methyl) dodecylacrylate, (methyl) lauryl acrylate, (methyl) stearyl acrylate base ester, (methyl) acrylic acid cyclopentyl ester, (methyl) cyclohexyl acrylate, (methyl) acrylic acid 2-methylcyclohexyl ester, three ring [5.2.1.0 can be enumerated 2,6] decane-8-base (methyl) acrylate (in this technical field, as popular name, is called (methyl) acrylic acid Bicvclopentyl ester.), (methyl) acrylate such as (methyl) acrylic acid dicyclo amoxy ethyl ester, (methyl) isobornyl acrylate, (methyl) acrylic acid diamantane ester, (methyl) allyl acrylate, (methyl) propargylacrylate, (methyl) phenyl acrylate, (methyl) acrylic acid naphthalene ester, (methyl) benzyl acrylate;
(methyl) acrylate containing hydroxyl such as (methyl) acrylic acid 2-hydroxy methacrylate, (methyl) acrylic acid 2-hydroxy propyl ester;
The dicarboxylic diesters such as diethyl maleate, DEF, diethyl itaconate;
Dicyclo [2.2.1] hept-2-ene", 5-methyl bicycle [2.2.1] hept-2-ene", 5-ethyl dicyclo [2.2.1] hept-2-ene", 5-hydroxyl dicyclo [2.2.1] hept-2-ene", 5-hydroxymethyl dicyclo [2.2.1] hept-2-ene", 5-(2 '-hydroxyethyl) dicyclo [2.2.1] hept-2-ene", 5-methoxyl dicyclo [2.2.1] hept-2-ene", 5-ethoxy dicyclo [2.2.1] hept-2-ene", 5,6-dihydroxy dicyclo [2.2.1] hept-2-ene", 5,6-bis-(hydroxymethyl) dicyclo [2.2.1] hept-2-ene", 5,6-bis-(2 '-hydroxyethyl) dicyclo [2.2.1] hept-2-ene", 5,6-dimethoxy dicyclo [2.2.1] hept-2-ene", 5,6-diethoxy dicyclo [2.2.1] hept-2-ene", 5-hydroxy-5-methyl base dicyclo [2.2.1] hept-2-ene", 5-hydroxyl-5-ethyl dicyclo [2.2.1] hept-2-ene", 5-hydroxymethyl-5-methyl bicycle [2.2.1] hept-2-ene", 5-tert-butoxycarbonyl dicyclo [2.2.1] hept-2-ene", 5-cyclohexyl oxygen base carbonyl dicyclo [2.2.1] hept-2-ene", 5-phenyloxycarbonyl dicyclo [2.2.1] hept-2-ene", two (tert-butoxycarbonyl) dicyclo [2.2.1] hept-2-ene" of 5,6-, the dicyclo unsaturated compounds such as two (cyclohexyl oxygen base carbonyl) dicyclo [2.2.1] hept-2-ene"s of 5,6-,
The dicarbonyl imides derivants such as N-phenylmaleimide, N-N-cyclohexylmaleimide, N-benzyl maleimide, N-succinimido-3-maleimidobenzoyl ester, N-succinimido-4-malimidobutanoate, N-succinimido-6-maleimidohexanoic acid ester, N-succinimido-3-maleimidopropionic acid ester, N-(9-acridinyl) maleimide;
Styrene, α-methyl styrene, a methyl styrene, p-methylstyrene, vinyltoluene, to methoxy styrene, vinyl cyanide, methacrylonitrile, vinyl chloride, vinylidene chloride, acrylamide, Methacrylamide, vinyl acetate, 1,3-butadiene, isoprene, 2,3-dimethyl-1,3-butadiene etc.
As (c), from the viewpoint of copolyreaction and thermotolerance, optimization styrene, N-phenylmaleimide, N-N-cyclohexylmaleimide, N-benzyl maleimide, dicyclo [2.2.1] hept-2-ene" etc.
The citing document recorded in the method that resin (B) can be recorded in list of references " experimental method of Polymer Synthesizing " (the grand row in large Tianjin work sale room (strain) chemistry is with people's the 1st edition the 1st printing distribution on March 1st, 1972) and the document manufactures.
And the multipolymer of gained both can directly use reacted solution, also can use solution that is concentrated or that dilute, the material that the methods such as utilization precipitates again are taken out as solid (powder) can also be used.Particularly, by using solvent described later (E) as solvent when this polymerization, just can directly use reacted solution, can manufacturing process be simplified.
As resin (B), 3,4-epoxycyclohexyl-methyl (methyl) acrylate/(methyl) acrylic copolymer, 3,4-epoxy three ring [5.2.1.0 can be enumerated 2.6] resin [K1] such as decyl acrylate/(methyl) acrylic copolymer, (methyl) glycidyl acrylate/(methyl) benzyl acrylate/(methyl) acrylic copolymer, (methyl) glycidyl acrylate/styrene/(methyl) acrylic copolymer, 3,4-epoxy three ring [5.2.1.0 2.6] resin [K2] such as decyl acrylate/(methyl) acrylic acid/N-N-cyclohexylmaleimide multipolymer, 3-methyl-3-(methyl) acryloyloxymethyl oxetanes/(methyl) acrylic acid/styrol copolymer, the resins [K3] such as (methyl) benzyl acrylate/(methyl) acrylic copolymer, styrene/(methyl) acrylic copolymer, the addition resin of (methyl) glycidyl acrylate on (methyl) benzyl acrylate/(methyl) acrylic copolymer, the addition resin of (methyl) glycidyl acrylate on (methyl) acrylic acid three ring ester/styrene in the last of the ten Heavenly stems/(methyl) acrylic copolymer, the resin [K4] etc. such as resin of addition (methyl) glycidyl acrylate on (methyl) acrylic acid three ring ester in the last of the ten Heavenly stems/(methyl) benzyl acrylate/(methyl) acrylic copolymer.
Wherein, preferred resin [K1] and resin [K2], more preferably resin [K1], further preferred 3,4-epoxy three ring [5.2.1.0 2.6] decyl acrylate/(methyl) acrylic copolymer.
The weight-average molecular weight of the polystyrene conversion of resin (B) is preferably 3,000 ~ 100,000, is more preferably 5,000 ~ 50,000, more preferably 5,000 ~ 35,000, be particularly preferably 6,000 ~ 30,000, be especially preferably 7,000 ~ 28,000.If molecular weight is in described scope, then hardness of film improve, residual film ratio is also high, unexposed portion to the favorable solubility of developer solution, the trend that resolution is improved.
The molecular weight distribution [weight-average molecular weight (Mw)/number mean molecular weight (Mn)] of resin (B) is preferably 1.1 ~ 6, is more preferably 1.2 ~ 4.
The acid number of resin (B) is preferably 50 ~ 150mg-KOH/g, is more preferably 60 ~ 135mg-KOH/g, more preferably 70 ~ 135mg-KOH/g.Acid number is herein the value measured as the amount (mg) that the resin (B) of 1g is neutralized necessary potassium hydroxide, such as, can carry out titration to obtain by using potassium hydroxide aqueous solution.
The content of resin (B) is preferably 7 ~ 65 quality % relative to the solid constituent of colored curable resin composition, is more preferably 13 ~ 60 quality %, more preferably 17 ~ 55 quality %.If the content of resin (B) is in described scope, then can form pattern, also have the trend that resolution and residual film ratio improve in addition.
< photopolymerizable compound (C) >
Colored curable resin composition of the present invention contains photopolymerizable compound (C).Photopolymerizable compound (C) to utilize the living radical of the generation from Photoepolymerizationinitiater initiater (D) by irradiation light and acid etc. to carry out the compound be polymerized, such as can enumerate the compound etc. of the ethylenic unsaturated bond with polymerism, preferably enumerate (methyl) acrylate compounds.
As photopolymerizable compound (C), preferably there is the photopolymerizable compound of the ethylenic unsaturated bond of more than 3.As this kind of photopolymerizable compound, such as, can enumerate tetramethylol methane tetraacrylate, pentaerythritol tetramethylacrylate, Dipentaerythritol Pentaacrylate, dipentaerythritol pentamethacrylates, dipentaerythritol acrylate, dipentaerythritol hexamethacrylate etc.Photopolymerizable compound (C) both may be used singly or in combination of two or more.
The content of photopolymerizable compound (C) is preferably 7 ~ 65 quality % relative to the solid constituent of colored curable resin composition, is more preferably 13 ~ 60 quality %, more preferably 17 ~ 55 quality %.If the content of described photopolymerizable compound (C) is in described scope, then can be cured fully, the film thickness ratio before and after development improves, and is difficult in pattern, form undercutting (undercut), adaptation has and becomes good trend, thus preferably.
< Photoepolymerizationinitiater initiater (D) >
Colored curable resin composition of the present invention contains Photoepolymerizationinitiater initiater (D).
As Photoepolymerizationinitiater initiater (D), as long as utilize the dissociation produces active free radical, acid etc. of light, the compound of initiated polymerization, be just not particularly limited, known polymerization initiator can be used.
As Photoepolymerizationinitiater initiater (D); preferably utilize the compound of the dissociation produces active free radical of light; more preferably comprise the Photoepolymerizationinitiater initiater of at least a kind be selected from alkyl phenones compound, triaizine compounds, acylphosphine oxide compound, oxime compound and united imidazole, preferably comprise the Photoepolymerizationinitiater initiater of oxime compound further.
As alkyl phenones compound, diethoxy acetophenone can be enumerated, 2-methyl-2-morpholinyl-1-(4-methyl mercapto phenyl) propane-1-ketone, 2-dimethylamino-1-(4-morpholino phenyl)-2-benzyl butane-1-ketone, 2-dimethylamino-1-(4-morpholino phenyl)-2-(4-methylphenylmethyl) butane-1-ketone, 2-hydroxy-2-methyl-1-phenyl-propane-1-ketone, benzil dimethyl ketal, 2-hydroxy-2-methyl-1-(4-(2-hydroxyl-oxethyl) phenyl propane-1-ketone, 1-hydroxycyclohexylphenylketone, 2-hydroxy-2-methyl-1-(the oligomer etc. of 4-(1-methyl ethylene) phenyl propane-1-ketone, preferably enumerate 2-methyl-2-morpholinyl-1-(4-methyl mercapto phenyl) propane-1-ketone, 2-dimethylamino-1-(4-morpholino phenyl)-2-benzyl butane-1-ketone etc.Also the commercially available products such as Irgacure (registered trademark) 369,907 (above is BASF AG's system) can be used.
As triaizine compounds, can 2 be enumerated, two (the trichloromethyl)-6-(4-methoxyphenyl)-1 of 4-, 3, 5-triazine, 2, two (the trichloromethyl)-6-(4-methoxyl naphthyl)-1 of 4-, 3, 5-triazine, 2, two (the trichloromethyl)-6-piperonyl-1 of 4-, 3, 5-triazine, 2, two (the trichloromethyl)-6-(4-methoxyl-styrene)-1 of 4-, 3, 5-triazine, 2, two (the trichloromethyl)-6-(2-(5-methylfuran-2-base) vinyl)-1 of 4-, 3, 5-triazine, 2, two (the trichloromethyl)-6-(2-(furans-2-base) vinyl)-1 of 4-, 3, 5-triazine, 2, two (the trichloromethyl)-6-(2-(4-diethylamino-2-aminomethyl phenyl) vinyl)-1 of 4-, 3, 5-triazine, 2, two (trichloromethyl)-6-(2-(3 of 4-, 4-Dimethoxyphenyl) vinyl)-1, 3, 5-triazine etc.
As acylphosphine oxide compound, TMDPO etc. can be enumerated.Also the commercially available products such as Irgacure (registered trademark) 819 (BASF AG's system) can be used.
As oxime compound; N-benzoyloxy-1-(4-Phenylsulfanylphenyl) butane-1-ketone-2-imines, N-benzoyloxy-1-(4-Phenylsulfanylphenyl) octane-1-ketone-2-imines, N-acetoxyl group-1-[9-ethyl-6-(2-methyl benzoyl)-9H-carbazole-3-base] ethane-1-imines, N-acetoxyl group-1-[9-ethyl-6-{2-methyl-4-(3 can be enumerated; 3-dimethyl-2,4-dioxolane ylmethyl oxygen base) benzoyl }-9H-carbazole-3-base] ethane-1-imines etc.Also the commercially available product such as Irgacure (registered trademark) OXE-01, OXE-02 (above is BASF AG's system), N-1919 (ADEKA Inc.) can be used.
As united imidazole, can 2 be enumerated, 2 '-bis-(2-chlorphenyl)-4,4 ', 5,5 '-tetraphenyl bisglyoxaline, 2,2 '-bis-(2,3-dichlorophenyl)-4,4 ', 5,5 '-tetraphenyl bisglyoxaline is (with reference to Japanese Unexamined Patent Publication 6-75372 publication, Japanese Unexamined Patent Publication 6-75373 publication etc.), 2,2 '-bis-(2-chlorphenyl)-4,4 ', 5,5 '-tetraphenyl bisglyoxaline, 2,2 '-bis-(2-chlorphenyl)-4,4 ', 5,5 '-four (alkoxyl phenyl) bisglyoxaline, 2,2 '-bis-(2-chlorphenyl)-4,4 ', 5,5 '-four (dialkoxy phenyl) bisglyoxaline, 2,2 '-bis-(2-chlorphenyl)-4,4 ', 5,5 '-four (tri-alkoxy phenyl) bisglyoxaline is (with reference to Japanese Patent Publication 48-38403 publication, Japanese Laid-Open Patent Publication 62-174204 publication etc.), 4,4 ', 5, the imidazolium compounds that the phenyl of 5 '-position be instead of by alkoxy carbonyl group is (with reference to Japanese Unexamined Patent Publication 7-10913 publication etc.) etc.Preferably enumerate 2,2 '-bis-(2-chlorphenyl)-4,4 ', 5,5 '
Tetraphenyl bisglyoxaline, 2,2 '-bis-(2,3-dichlorophenyl)-4,4 ', 5,5 '-tetraphenyl bisglyoxaline, 2,2 '-bis-(2,4-dichlorophenyl)-4,4 ', 5,5 '-tetraphenyl bisglyoxaline.
As utilizing the acidic acid-producing agent of light, salt or nitrobenzyl tosylat, the benzoin tosylate etc. such as 4-hydroxy phenyl dimethyl sulfonium tosilate, 4-hydroxy phenyl dimethyl sulfonium hexafluoro antimonate, 4-acetoxyl group phenyl dimethyl sulfonium tosilate, 4-acetoxyl group phenyl methyl benzyl sulfonium hexafluoro antimonate, triphenylsulfonium tosilate, triphenylsulfonium hexafluoro antimonate, diphenyl iodine tosilate, diphenyl iodine hexafluoro antimonate can be enumerated.
Photoepolymerizationinitiater initiater (D) also can be that triaizine compounds etc. utilizes light to produce the compound of living radical and acid simultaneously.
As Photoepolymerizationinitiater initiater (D), the benzoin compounds such as benzoin, benzoin methylether, benzoin ethyl ether, benzoin iso-propylether, benzoin isobutyl ether can also be enumerated; Benzophenone, o-benzoyl yl benzoic acid methyl esters, 4-phenyl benzophenone, 4-benzoyl-4 '-dimethyl diphenyl sulfide, 3,3 ', 4,4 '-four (t-butyl peroxy carbonyl) benzophenone, 2, the benzophenone cpds such as 4,6-tri-methyl benzophenone; The naphtoquinone compounds such as 9,10-phenanthrenequione, 2-EAQ, camphorquinone; 10-butyl-2-chloro-acridine ketone, benzil, phenylglyoxalates methyl esters, two cyclopentadiene titanium compounds etc.They preferably cause auxiliary agent (D1) (amine etc.) and combinationally use with photopolymerization described later.
The content of Photoepolymerizationinitiater initiater (D) is preferably 0.1 ~ 30 mass parts relative to total amount 100 mass parts of resin (B) and photopolymerizable compound (C), is more preferably 1 ~ 20 mass parts.If the content of Photoepolymerizationinitiater initiater is in described scope, then can high-sensitivity and shorten the time shutter, productivity improves.
< photopolymerization causes auxiliary agent (D1) >
In colored curable resin composition of the present invention, still can cause auxiliary agent (D1) containing photopolymerization.Photopolymerization causes auxiliary agent (D1) and is usually combinationally used by with Photoepolymerizationinitiater initiater (D), is to promote the compound that the polymerization of the photopolymerizable compound after by Photoepolymerizationinitiater initiater initiated polymerization uses or sensitizer.
Cause auxiliary agent (D1) as photopolymerization, amines, alkoxy anthracene compound, thioxanthone compounds, carboxylic acid compound etc. can be enumerated.
As amines, triethanolamine can be enumerated, methyldiethanolamine, triisopropanolamine, 4-dimethylaminobenzoic acid methyl esters, EDMAB, 4-dimethylaminobenzoic acid isopentyl ester, benzoic acid 2-dimethylamino ethyl ester, 4-dimethylaminobenzoic acid 2-Octyl Nitrite, N, N-dimethyl-p-toluidine, 4, 4 '-bis-(dimethylamino) benzophenone (common name Michler's keton), 4, 4 '-bis-(diethylamino) benzophenone, 4, 4 '-bis-(ethylmethylamino) benzophenone etc., wherein preferably 4, 4 '-bis-(diethylamino) benzophenone.Also the commercially available products such as EAB-F (hodogaya chemical industry (strain) system) can be used.
As alkoxy anthracene compound, 9,10-dimethoxy anthracene, EDMO, 9,10-diethoxy anthracenes, 2-ethyl-9,10-diethoxy anthracene, 9,10-dibutoxy anthracenes, 2-ethyl-9,10-dibutoxy anthracene etc. can be enumerated.
As thioxanthone compounds, ITX, ITX, 2,4-diethyl thioxanthones, 2,4-bis-clopenthixal ketones, the chloro-4-propoxythioxanthone of 1-etc. can be enumerated.
As carboxylic acid compound, thiophenyl acetic acid, methylphenyl-sulfanyl acetic acid, ethylthiophenyl acetic acid, ethyl methyl benzene ethyl thioglycollic acid, dimethyl benzene ethyl thioglycollic acid, Methoxv-phenylsulfanvl acetic acid, dimethoxyphenylthio acetic acid, chlorophenylsulfanyl acetic acid, dichloro-benzenes ethyl thioglycollic acid, N-phenylglycine, phenoxyacetic acid, naphthylthio acetic acid, N-naphthyl glycocoll, naphthoxy acetic acid etc. can be enumerated.
Photopolymerization causes auxiliary agent (D1) and both may be used singly or in combination of two or more.
When using these photopolymerization to cause auxiliary agent (D1), its use amount is preferably 0.01 ~ 50 mass parts relative to resin (B) and total amount 100 mass parts of polymerizable compound (C), is more preferably 0.1 ~ 40 mass parts.In addition, relative to Photoepolymerizationinitiater initiater (D) 1 mole, be preferably 0.01 ~ 10 mole, be more preferably 0.01 ~ 5 mole.If the amount that polymerization causes auxiliary agent (D1) is in this scope, then can form pattern with higher sensitivity, the trend that the productivity of pattern is improved.
< solvent (E) >
Colored curable resin composition of the present invention also can contain solvent (E).
Solvent (E) is not particularly limited, and can use normally used solvent in this field.As solvent (E), can from choice for use in the middle of the ketone solvent (solvent containing-CO-) beyond the ether solvents (solvent containing-O-) beyond ester solvent (solvent containing-COO-), ester solvent, ether-ether solvent (solvent containing-COO-and-O-), ester solvent, alcoholic solvent, aromatic hydrocarbon solvents, amide solvent, dimethyl sulfoxide (DMSO) etc.
As ester solvent, methyl lactate, ethyl lactate, butyl lactate, 2-hydroxy-methyl isobutyl acid, ethyl acetate, n-butyl acetate, isobutyl acetate, amyl formate, isoamyl acetate, butyl propionate, isopropyl isobutyrate, ethyl butyrate, butyl butyrate, methyl pyruvate, ethyl pyruvate, Propyl pyruvate, methyl acetoacetate, ethyl acetoacetate, ethyl cyclohexyl alcohol ester, gamma-butyrolacton etc. can be enumerated.
As ether solvents, glycol monoethyl ether, ethylene glycol monoethyl ether, ethylene glycol ether, ethylene glycol monobutyl ether, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, diethylene glycol monobutyl ether, propylene glycol monomethyl ether, dihydroxypropane single-ether, propylene glycol monopropyl ether, propylene glycol monobutyl ether, 3-methoxyl-n-butyl alcohol, 3-methoxyl-3-methyl butanol, tetrahydrofuran, oxinane, Isosorbide-5-Nitrae-diox, diethylene glycol dimethyl ether, diethyl carbitol, diglycol ethyl methyl ether, diglycol dipropyl ether, diethylene glycol dibutyl ether, methyl phenyl ethers anisole, phenetol, methylanisole etc. can be enumerated.
As ether-ether solvent, methoxy menthyl acetate can be enumerated, ethyl methoxyacetate, methoxyacetic acid butyl ester, ethoxy acetate, ethoxy ethyl acetate, 3-methoxy methyl propionate, 3-methoxypropionate, 3-ethoxypropanoate, 3-ethoxyl ethyl propionate, 2-methoxy methyl propionate, 2-methoxypropionate, 2-methoxy propyl propyl propionate, 2-ethoxypropanoate, 2-ethoxyl ethyl propionate, 2-methoxyl-2 Methylpropionic acid methyl esters, 2-ethoxy-2 Methylpropionic acid ethyl ester, 3-methoxybutyl acetic acid esters, 3-methyl-3-methoxybutyl acetic acid esters, propylene glycol methyl ether acetate, propylene glycol monoethyl ether acetate, propylene glycol monopropyl ether acetic acid esters, ethylene glycol monomethyl ether acetate, ethylene glycol monoethyl ether acetate, diethylene glycol monoethyl ether acetic acid esters, diethylene glycol monobutyl ether acetic acid esters etc.
As ketone solvent, 4-hydroxy-4-methyl-2-pentanone, acetone, 2-butanone, 2-HEPTANONE, 3-heptanone, 4-heptanone, 4-methyl-2 pentanone, cyclopentanone, cyclohexanone, isophorone etc. can be enumerated.
As alcoholic solvent, methyl alcohol, ethanol, propyl alcohol, butanols, hexanol, cyclohexanol, ethylene glycol, propylene glycol, glycerine etc. can be enumerated.
As aromatic hydrocarbon solvents, benzene,toluene,xylene, sym-trimethyl benzene etc. can be enumerated.
As amide solvent, DMF, DMA, 1-METHYLPYRROLIDONE etc. can be enumerated.
These solvents both may be used singly or in combination of two or more.
In the middle of above-mentioned solvent, from the viewpoint of coating, drying property, the boiling point under preferred latm is more than 120 DEG C and the organic solvent of less than 180 DEG C.Wherein, preferred propylene glycol methyl ether acetate, ethyl lactate, propylene glycol monomethyl ether, 3-ethoxyl ethyl propionate, glycol monoethyl ether, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, 4-hydroxy-4-methyl-2-pentanone, N, dinethylformamide, 1-METHYLPYRROLIDONE etc., more preferably propylene glycol monomethyl ether, propylene glycol methyl ether acetate, ethyl lactate, 3-ethoxyl ethyl propionate etc.If containing these solvents, then flatness when being coated with is excellent.
The content of the solvent (E) in colored curable resin composition is preferably 70 ~ 95 quality % relative to colored curable resin composition, is more preferably 75 ~ 92 quality %.In other words, the solid constituent of colored curable resin composition is preferably 5 ~ 30 quality %, is more preferably 8 ~ 25 quality %.If the content of solvent (E) is in described scope, then flatness when being coated with is good, and when forming color filter, colour saturation can not be not enough in addition, and therefore display characteristic has and becomes good trend.
Colored curable resin composition of the present invention also can contain the various adjuvants such as surfactant, filling agent, other macromolecular compound, closely sealed promoter, antioxidant, levelling agent, ultraviolet light absorber, light stabilizer, chain-transferring agent as required.
In addition, the color filter formed by above-mentioned cured composition for color is also in category of the present invention.
This color filter can utilize the method comprising following operation to obtain, that is, be coated on substrate by cured composition for color, then carries out drying, makes dyed layer thus and (is sometimes called " composition layer " by this layer.), then the dyed layer of gained is solidified.
As the method for the colored pattern by cured composition for color manufacture color filter of the present invention, photoetching process, ink-jet method, print process etc. can be enumerated.Wherein, preferred light lithography.Photoetching process is following method, namely, colored curable resin composition is coated on substrate or other resin bed (other the colored curable resin composition layer etc. such as first formed on substrate), utilize dry grade except volatile ingredients such as desolventizings and form dyed layer, then across photomask by the exposure of this dyed layer, development.In photolithography, by not using photomask when exposing and/or do not develop, the film of the solidfied material as above-mentioned dyed layer can just be formed.
The thickness of film is now not particularly limited, and suitably can adjust, be generally 0.1 ~ 30 μm according to material used, purposes etc., is preferably 1 ~ 20 μm, is more preferably 1 ~ 6 μm.
As the coating process of colored curable resin composition, extrusion coating methods, directly gravure coating process, oppositely gravure coating process, CAP rubbing method, mould Tu Fa etc. can be enumerated.Also the coating machine coatings such as dip coater, bar coater, spin coater, the rotary coating machine of slit &, slit coater (be sometimes also referred to as mould and be coated with machine, showering curtain type three-dimensional coating machine, the rotatable coating machine of irrotationality) can be used.
Removing/the drying of solvent can utilize natural drying, aeration-drying, drying under reduced pressure, heat drying etc. to carry out.Concrete baking temperature is preferably 10 ~ 120 DEG C, is more preferably 25 ~ 100 DEG C.
Preferably 10 seconds ~ 60 minutes drying time, more preferably 30 seconds ~ 30 minutes.
Drying under reduced pressure preferably carries out under the pressure of 50 ~ 150Pa, in the scope of 20 ~ 25 DEG C.
The photomask of dried film across the pattern for the formation of target is exposed.
Pattern form on photomask is now not particularly limited, and can use the pattern form corresponding with the purposes as target.
As light source used in exposure, preferably produce the light source of the light of the wavelength of 250 ~ 450nm.Specifically, mercury vapor lamp, light emitting diode, metal halide lamp, Halogen lamp LED etc. can be enumerated, the wave filter intercepting particular wavelength region also can be used to carry out intercepting or use the bandpass filter of taking out particular wavelength region optionally take out and expose.
Due to parallel rays can being irradiated equably to whole plane of exposure, carries out the correct contraposition of mask and base material, therefore preferably use the device such as mask aligner, step photo-etching machine.
After exposure, make it contact developer solution and established part (unexposed portion etc.) is dissolved, developing, can pattern be obtained thus.As developer solution, the aqueous solution etc. of alkali compounds (potassium hydroxide, sodium carbonate, Tetramethylammonium hydroxide etc.) can be enumerated.This developer solution also can contain surfactant.
Developing method can be any one methods such as paddle board method, infusion process, spray-on process.In addition also can develop time by substrate with arbitrary angular slope.Preferably wash after development.
In addition, as required, also rear baking can be carried out.The rear baking such as preferred scope of 150 ~ 230 DEG C, 10 ~ 240 minutes.
According to colored curable resin composition of the present invention, the color filter of lightness and good film, pattern and the high-quality of contrast can be obtained.In the display device that can be used for it can be used as a part for component parts to possess with known form in these color filters or pattern, the various all machines relevant with rendered image such as such as known liquid crystal indicator, organic el device, solid-state imager.
Enumerate embodiment below and more specific description is carried out to the present invention.In example, the % of expression content or use amount and part, as long as no particularly pointing out, are exactly quality criteria.
Below, mass spectrum (LC is utilized; Agilent system 1200 type, MASS; Agilent LC/MSD type) confirm the structure of compound.
(synthesis example 1)
Add 65 parts, water in 2-amino-4-mesyl-6-nitrophenol (CAS No.101861-04-5) 7.5 parts after, add 1.3 parts, NaOH, make it to dissolve.In ice bath, add 35% sodium nitrite (pharmaceutical worker industry (strain) system pure with light) aqueous solution 6.1 parts, then little by little add 35% hydrochloric acid 19.4 parts and make it to dissolve, stirring 2 hours, obtain the suspension containing diazo salt.Then add at leisure and sulfaminic acid (pharmaceutical worker's industry (strain) system pure with light) 5.6 parts is dissolved in the aqueous solution obtained in 26 parts, water, make superfluous sodium nitrite deactivation.
Then, make Edaravone (pharmaceutical worker industry (strain) system pure with light) 5.6 parts be suspended in 70 parts, water, use NaOH, pH is adjusted to 8.0.While suitably adding 10% sodium hydroxide solution in the mode be limited in by pH in the scope of 7 to 7.5, dripped the described suspension containing diazo salt wherein with 15 minutes.After dropping terminates, then stir 30 minutes, obtain yellow suspension thus.Stir 1 hour.Yellow solid filtration obtained, under reduced pressure 60 DEG C of dryings, obtains the compound 11.7 parts (yield 87%) represented with formula (p-2).
The compound 10 parts of formula (p-2) added in dimethyl formamide (Tokyo changes into industry (strain) system) 100 parts and dissolve, after adding 3.1 parts, chromium ammonium suplhate (III) 12 hydrate (with light pure pharmaceutical worker industry (strain) system), sodium acetate (pharmaceutical worker's industry (strain) system pure with light) 1.1 parts, add hot reflux 4 hours 30 minutes.After cool to room temperature, reaction solution is injected 20% saline solution 1500 parts, by the red-orange solid that obtains after filtering 60 DEG C of dryings, obtain the compound 13.6 parts (yield 63%) represented with formula (z-2A).
(synthesis example 2)
Make and the compound 9.1 parts represented with formula (z-2A) is dissolved in the solution (d-1) obtained in 100 parts, water.In solution (d-1), added APTES (Tokyo changes into industry (strain) system) 2.2 parts with 1 hour, stir 24 hours thereafter.Filter the sediment generated, after the cleaning of 1000 parts, water, 60 DEG C of drying under reduced pressure 24 hours, obtain the compound 1.0 parts represented with formula (z-3).
(synthesis example 3)
In the flask possessing stirring machine, thermometer, reflux condenser and tap funnel, flow through nitrogen with 0.02L/ minute and be set to nitrogen atmosphere, adding propylene glycol methyl ether acetate 305 parts, stir and be heated to 70 DEG C.
Then, by 60 parts, acrylic acid, 3,4-epoxy three ring [5.2.1.0 2.6] compound represented with formula (I-1) (mixes with mol ratio 50: 50 with the compound represented with formula (II-1) by decyl acrylate.) 440 parts be dissolved in propylene glycol methyl ether acetate 140 parts and prepare solution, to be incubated be in the flask of 70 DEG C with within 4 hours, to be added drop-wise to by this solution to use tap funnel.
On the other hand, by polymerization initiator 2,2 '-azo two (2,4-methyl pentane nitrile) 30 parts is dissolved in propylene glycol methyl ether acetate 225 parts, uses other tap funnel to be added drop-wise in flask with 4 hours the solution of gained.After the dropping of the solution of polymerization initiator terminates, keep 4 hours at 70 DEG C, cool to room temperature thereafter, obtaining weight-average molecular weight (Mw) is 9.1 × 10 3, molecular weight distribution is 2.16, solid constituent is 34.8%, solid constituent converts acid number is resin B 1 solution of 81mg-KOH/g.Resin B 1 has following shown structural unit.
The weight-average molecular weight (Mw) of the resin obtained in synthesis example and the mensuration of number mean molecular weight (Mn) use GPC method to carry out under the following conditions.
Device: K2479 ((strain) Shimadzu Seisakusho Ltd. system)
Chromatographic column: SHIMADZU Shim-pack GPC-80M
Column temperature: 40 DEG C
Solvent: THF (tetrahydrofuran)
Flow velocity: 1.0mL/min
Detecting device: RI correction standard substance; TSK STANDARD POLYSTYRENEF-40, F-4, F-288, A-2500, A-500 (Tosoh (strain) system)
Using the weight-average molecular weight of polystyrene conversion obtained above and number mean molecular weight ratio (Mw/Mn) as molecular weight distribution.
Embodiment 1
By photosensitive composition is prepared in following each composition mixing.
Embodiment 2
By photosensitive composition is prepared in following each composition mixing.
Comparative example 1
By colored resin composition is prepared in following each composition mixing.
Test example
(making of colored pattern)
At glass substrate (the Eagle XG of 2 inch square; Corning Inc.) on, after utilizing the composition obtained in spin-coating method coating Examples 1, embodiment 2 or comparative example 1, form the composition layer of thick 2.5 μm 100 DEG C of prebake conditions 3 minutes.
Naturally after cooling, the interval of figuratum for tool quartz glass photomask and combinations thereof nitride layer is set to 100 μm, uses exposure machine (TME-150RSK; TOPCON (strain) makes), under air atmosphere, with 150mJ/cm 2exposure (365nm benchmark) carry out illumination and penetrate.
As photomask, employ the mask being formed with 100 μm of lines and space pattern.After illumination is penetrated, by the film of gained is developed 23 DEG C of dippings 80 seconds in the water system developer solution (buck system developer solution) containing nonionic system surfactant 0.12% and sodium carbonate 2%, after washing, in an oven, carry out 20 minutes at 230 DEG C after baking, obtain colored pattern.
(Evaluation of Heat Tolerance)
At glass substrate (the Eagle XG of 2 inch square; Corning Inc.) on, utilize the composition obtained in spin-coating method coating Examples 1, embodiment 2 or comparative example 1, form the coating layer of thick 2.5 μm thus.Then, by above-mentioned coated film 230 DEG C of heating 20 minutes, use colour examining machine (OSP-SP-200; OLYMPUS Inc.) determine coated film heating before and after aberration (Δ Eab*).
To the coated film that the composition by embodiment 1 and embodiment 2 obtains, implement Evaluation of Heat Tolerance, consequently, aberration (Δ Eab*) is respectively 4.2 and 4.8.
Similarly implement Evaluation of Heat Tolerance to the coated film that the composition by comparative example 1 obtains, consequently, aberration (Δ Eab*) is 5.1, the excellent heat resistance of known the application's photosensitive composition.
Utilizability in industry
If use colored curable resin composition of the present invention, the color filter of excellent heat resistance just can be provided.This color filter is useful as color filter used in display device (liquid crystal indicator, organic el device, Electronic Paper etc.) and solid-state imager.

Claims (7)

1. a colored curable resin composition, it contains:
Comprise the colorant (A) of the compound represented with formula (I),
Resin (B),
Photopolymerizable compound (C) and
Photoepolymerizationinitiater initiater (D);
X -Y +(I)
In formula (I), X -represent the negative ion coming from dyestuff, Y +represent the kation coming from the compound represented with formula (Y);
In formula (Y), n represents the integer of 1 ~ 8, R 40represent the alkyl of carbon number 1 ~ 4.
2. colored curable resin composition according to claim 1, wherein,
The negative ion coming from dyestuff is the negative ion come from containing golden azo dyes or triarylmethane dye.
3. colored curable resin composition according to claim 1 and 2, wherein,
The negative ion coming from dyestuff comes from the negative ion containing golden azo dyes.
4. colored curable resin composition according to claim 2, wherein,
The negative ion come from containing golden azo dyes represents with formula (A0),
In formula (A0), R 1~ R 18represent the alkyl of 1 valency of hydrogen atom, halogen atom, carbon number 1 ~ 10, nitro or-SO independently of one another 2r 29;
R 29represent-OH ,-NHR 30or-R 32;
R 30the alkyl representing 1 valency of hydrogen atom, carbon number 1 ~ 10, the cyclohexyl ,-R that can be replaced by the alkyl of carbon number 1 ~ 4 31-O-R 33,-R 34-CO-O-R 35,-R 36-O-CO-R 37, or the aralkyl of carbon number 7 ~ 10;
R 31, R 34and R 36represent the alkylidene of the divalent of carbon number 1 ~ 8 independently of one another;
R 32, R 33, R 35and R 37represent the alkyl of 1 valency of carbon number 1 ~ 8 independently of one another;
R 19and R 20represent hydrogen atom, methyl, ethyl or amino independently of one another;
M 1represent Cr or Co.
5. colored curable resin composition according to claim 1 and 2, wherein,
Colorant (A) is also containing pigment.
6. a color filter, it utilizes the colored curable resin composition described in claim 1 or 2 to be formed.
7. a display device, it comprises color filter according to claim 6.
CN201410777700.1A 2013-12-17 2014-12-15 Colored curable resin composition Active CN104714366B (en)

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