CN105372936A - Red coloring composition for color filter - Google Patents
Red coloring composition for color filter Download PDFInfo
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- CN105372936A CN105372936A CN201510441245.2A CN201510441245A CN105372936A CN 105372936 A CN105372936 A CN 105372936A CN 201510441245 A CN201510441245 A CN 201510441245A CN 105372936 A CN105372936 A CN 105372936A
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Abstract
The invention provides a red color composition for color filter, which is used to produce television display. The color filter has high brightness, and the brightness is barely changed even if the color filter is baked. The red coloring composition is mainly composed of the following components: pigment, pigment dispersant comprising acidic groups, dye, pigment dispersant, resin, compounds comprising phosphate radical and salts thereof, and organic solvent, and is characterized in that the dye is one of C.I. acidic red 52, C.I. acidic red 87, C.I. acidic red 92, C.I. acidic red 289, C.I. acidic red 388.
Description
Technical field
The present invention relates to the colored filter red stain composition of the formation of the colored filter that can be used for colour display device.
Background technology
The colored filter that color liquid crystal display arrangement etc. utilize is made up of following: on the surface of the transparency carrier of glass etc. two or more different form and aspect of configured in parallel fine band (band) or fine pixel is configured according to sequence fixing in length and breadth.Pixel size is several 10 ~ several 100 μm of fine like this sizes, and each form and aspect fitly arrange according to the order of regulation.
Color liquid crystal display arrangement is make the white light from backlight through above-mentioned colored filter thus painted, and on picture color display.Therefore, as the key property of colored filter, high transparent is needed.Therefore, carry out dyeing and so-called decoration method etc. manufacture by using the dyestuff of excellence in color characteristic to be distributed in resin with molecular state in the past.But, in recent years along with the variation of purposes, when needing the reliability improving thermotolerance, photostability etc., organic pigment can be used to replace the dyestuff of above-mentioned limited capacity degree.In addition, about the autofrettage of colored filter, it is also proposed the various methods such as print process, ink-jet method, photoetching process.
Especially, in the purposes of television indicator etc., need the colored filter with following pixel: can high brightness be realized, and the height contrastization of the high-precision refinement bringing general image can be realized.
Above-mentioned brightness, contrast performance largely depend on the kind of the pigment be dispersed in each color pixel of colored filter, especially can frequently use paratonere 254, paratonere 177 etc.
Such as, in patent documentation 1, propose the system share orange pigment relative to the paratonere 254 of main red pigment and paratonere 177.
In patent documentation 2, the brightness proposing contrast in order to make up paratonere 254 when paratonere 177 uses the system of paratonere 176.
But in recent years, the quality that the pixel of television indicator is pursued improves all the more, the performance needed for being difficult to realize by the colored filter dye compositions only with pigment as colorant.Especially, proposing to reach high brightness, in colored filter dye compositions, share pigment and dyestuff.
Propose in patent documentation 3 and use paratonere 254, paratonere 177 as pigment, and use the system of the modifier of acid red 289, acid red 87 etc. as dyestuff, but due to the modified process of dyestuff numerous and diverse, need labour and cost, so shortcoming practicality.
In addition, when share pigment and dyestuff in colored filter dye compositions, the ageing stability that there is colored filter dye compositions becomes insufficient trend, and,, there is the trend that brightness reduces in the front and back of the rear baking operation in the making of colored filter.
Prior art document
Patent documentation
Patent documentation 1 Japanese Unexamined Patent Publication 2010-223987 publication
Patent documentation 2 Japanese Unexamined Patent Publication 2009-237462 publication
Patent documentation 3 Japanese Unexamined Patent Publication 2012-194521 publication
Summary of the invention
Problem of the present invention is to provide the high brightness with the colored filter that can be used for the display device such as television indicator, even and if through after dry the also little colored filter red stain composition of process brightness change.
Present inventor conducts in-depth research to solve above-mentioned problem, found that and can obtain following colored filter red stain composition: it forms primarily of pigment, the pigment dispersion aids with acidic-group, dyestuff, pigment dispersing agent, resin, the compound with phosphate or its salt and organic solvent, and there is the high brightness that can be used for colored filter, even and if through after to dry process brightness change also little, thus complete the present invention.
Namely the present invention is as follows,
(1) a kind of colored filter red stain composition, it forms primarily of pigment, the pigment dispersion aids with acidic-group, dyestuff, pigment dispersing agent, resin, the compound with phosphate or its salt and organic solvent, it is characterized in that, described pigment has pyrrolo-pyrrole-dione skeleton, and described dyestuff is be selected from least a kind in C.I. acid red 52, C.I. acid red 87, C.I. acid red 92, C.I. acid red 289 and C.I. acid red 388.
(2) the red stain composition of the colored filter Gen Ju (1), is characterized in that, described in there is the compound of phosphate or its salt acid number be 10 ~ 300mgKOH/g.
(3) according to (1) or the red stain composition of the colored filter described in (2), it is characterized in that, described in there is the compound of phosphate or its salt content be 10 ~ 1000 mass parts relative to described dyestuff 100 mass parts.
(4) according to the colored filter red stain composition according to any one of (1) ~ (3), it is characterized in that, described pigment is the pigment through micronize process.
(5) according to colored filter red stain composition according to any one of (1) ~ (4), it is characterized in that, described in there is the pigment dispersion aids of acidic-group for having sulfonic pigment dispersion aids.
And, in this manual, " acid number " is sample propylene glycol monomethyl ether dissolved or dispersion, and at 25 DEG C, phenolphthalein is carried out titration as the ethanolic solution of indicator potassium hydroxide, and is that rose pink point carries out as terminal the value that calculates by following formula using measuring liquid.
Acid number (mgKOH/g)=56.1 × V × C/m
V: titer (ml),
C: the concentration (mol/l) of vs,
M: nonvolatile component weight (g) of sample.
According to the present invention, can obtain while brightness excellence, even if dry the also little colored filter red stain composition of process brightness change by rear.
As mentioned above, when share pigment and dyestuff in colored filter red stain composition, the ageing stability that there is colored filter dye compositions becomes insufficient trend, in addition, in the front and back of the rear baking operation of the making of colored filter, there is the trend that brightness reduces.
This trend is investigated by following mechanism.That is, in the composition of film forming colored filter, dye molecule is relatively low molecular weight, is easy to carry out thermal motion so become at the rear dye molecule dried through heating in process.In addition, because dye molecule has the so high polar group of sulfonate, be easy to assemble so the dye molecule of thermal motion is become by the interaction each other of high polar group.Its result, dries among the colored filter film after processing rear, produces and comprise the region of the aggregation of dye molecule and the region comprising relative less dye molecule.Rear dry process after colored filter on irradiate the light of backlight time, by the relatively less region of the dyestuff in colored filter film through light observe low-light level.
According to the present invention, though through after dry process the change of brightness also can be suppressed to be investigated by following mechanism.Namely, by the material containing phosphate or its salt is imported in colored filter dye compositions, even if dye molecule carries out thermal motion, by phosphate or its salt, the high polar group interaction each other that dye molecule has is obstructed, even if so after rear baking process, dye molecule also exists equably in colored filter film, therefore, diminish in rear change of drying the front and back brightness of process.
Below, about colored filter red stain composition of the present invention, its each composition is specifically described.
Embodiment
The present invention is the invention of the colored filter red stain composition relating to the display device such as television indicator, as this colored filter red stain composition, for the composition not being resist, or also can be anti-corrosion agent composition.
In a word, the colored filter red stain composition of the display device of television indicator of the present invention etc. is the composition of the colored filter of the display device that can be used for television indicator etc., as consequent effect of the present invention, can provide and there is high brightness, even and if through after dry the also little colored filter red stain composition of change of process brightness.
(pigment)
As pigment, colored filter red stain composition of the present invention uses the pigment with pyrrolo-pyrrole-dione skeleton.As concrete example, the pigment of C.I. paratonere 254, C.I. paratonere 254, C.I. paratonere 255, C.I. paratonere 264, C.I. paratonere 272, C.I. pigment orange 71, C.I. pigment orange 73 or C.I. pigment orange 81 etc. through bromination can be enumerated, but be not limited to these.
As the pigment with pyrrolo-pyrrole-dione skeleton, preferred C.I. paratonere 254 or its bromide.Especially, when using C.I. paratonere 254, in order to the thickness of the film obtaining necessary lightness is thin, and color characteristic (x, y, Y) becomes good.There is in the present invention the use amount of the pigment of pyrrolo-pyrrole-dione skeleton, relative to the total solid composition of red stain composition of the present invention in mass fraction, preferably 5 ~ 80 quality %, more preferably 20 ~ 50 quality %.
In order to give colored filter red stain composition of the present invention with high brightness, contrast, preferably use the coloring pigment through micronize process.By carrying out micronize process, the primary particle size of coloring pigment can be made fine further and evenly.
As above-mentioned micronize process, such as, preferably carry out micronize process as described below: untreated coloring pigment will be comprised, water miscible inorganic salts are (at sodium chloride, barium chloride, preferred sodium chloride in potassium chloride etc., the mean grain size preferably water-soluble inorganic salt of less than 50 μm as used water-soluble inorganic salt) and do not dissolve in fact water soluble disperse medium (the alkoxy alcohols of above-mentioned water-soluble inorganic salt, glycols, ethers etc.) potpourri pass through kneader, roller mill, bowl mill, masher (attritor), sand mill, the TRI-MIX (trade (brand) name) of the Inoue MFG. Inc. as planetary stirring machine (planetarymixer) described in Japanese Unexamined Patent Publication 2006-192385 publication, as the kneading device of the MiracleKCK etc. of Asada Iron Works Co., Ltd. of continuous single-shaft mixing roll carry out mixing after, carry out the salt mill process removing above-mentioned water miscible inorganic salts and above-mentioned water soluble disperse medium.
(there is the pigment dispersion aids of acidic-group)
As the pigment dispersion aids with acidic-group that colored filter red stain composition of the present invention uses, in the basic framework with the same or similar molecular structure with pigment, preferably import the pigment dispersion aids that improve with the acidic-group of the compatibility of organic solvent.Such pigment dispersion aids is in the operation of the micronize of pigment, dispersion; the partial adsorbates of basic framework is in surface of pigments; acidic-group improves the affinity with organic solvent, pigment dispersing agent, have accordingly after miniaturization when improving pigment dispersion, dispersion through time dispersion stabilization etc. effect.In addition, due to pigment dispersion aids autolysis in organic solvent or become can in surface of pigments scope absorption more widely with microgranular pigment dispersion aids of carrying out the state of disperseing, so preferred further.
Wherein, when use as acidic-group there is sulfonic pigment dispersion aids etc. time, good result can be obtained.
In colored filter red stain composition of the present invention, having the use amount of the pigment dispersion aids of acidic-group, is 0.5 ~ 30 mass parts relative to pigment 100 mass parts.When the above-mentioned content with the pigment dispersion aids of acidic-group is less than 0.5 mass parts, pigment dispersion effect reduces, and on the other hand, when more than 30 mass parts, pigment dispersion effect does not continue to improve.
The above-mentioned pigment dispersion aids with acidic-group:
(1) to be used in when there is not the pigment dispersion aids with acidic-group when the pigment of micronize process; when the dispersion of the pigment through micronize process; relative to coloring pigment 100 mass parts; use pigment dispersion aids 0.5 ~ 30 mass parts with acidic-group, preferably 3 ~ 15 mass parts.
(2) be used under the existence of the pigment dispersion aids with acidic-group when the pigment of micronize process, when the micronize process of pigment, use pigment dispersion aids 0.5 ~ 30 mass parts relative to pigment 100 mass parts, preferably 3 ~ 15 mass parts; When the dispersion of the pigment through micronize process, use pigment dispersion aids 0 ~ 29.5 mass parts with acidic-group relative to pigment 100 mass parts, preferably 0 ~ 12 mass parts.
And; the use amount with the pigment dispersion aids of acidic-group used when micronize process and the summation with the use amount of the pigment dispersion aids of acidic-group used when disperseing through the pigment of micronize process; relative to pigment 100 mass parts; use pigment dispersion aids 0.5 ~ 30 mass parts with acidic-group, preferably 3 ~ 15 mass parts.
More specifically, as the pigment dispersion aids with acidic-group, be described using the situation with sulfonic pigment dispersion aids.
As pigment, when C.I. paratonere 254 as red pigment is disperseed, as having sulfonic pigment dispersion aids, can use and be selected from that to have with C.I. paratonere 254 be the pigment of the pyrrolo-pyrrole-dione skeleton of identical skeleton and/or the sulfonated bodies (sulfonated bodies of C.I. paratonere 254 of pigment, through the sulfonated bodies of the C.I. paratonere 254 of bromination, C.I. the sulfonated bodies of paratonere 255, C.I. the sulfonated bodies of paratonere 264, C.I. the sulfonated bodies of paratonere 272, C.I. the sulfonated bodies of pigment orange 71, C.I. the sulfonated bodies of pigment orange 73, C.I. the sulfonated bodies etc. of pigment orange 81) and C.I. paratonere 2 sulfonated bodies at least a kind there is sulfonic pigment dispersion aids, wherein, the sulfonated bodies of preferred use C.I. paratonere 2.
(dyestuff)
As the dyestuff that colored filter red stain composition of the present invention uses, oxa anthracenes acid dyes can be used.As oxa anthracenes acid dyes, preferably use C.I. acid red 50, C.I. CI 45430, C.I. acid red 52, C.I. acid red 87, C.I. acid red 92, C.I. acid red 289, C.I. acid red 388, acid rhodamine G, C.I. acid violet 9, C.I. acid violet 30.Wherein, preferably C.I. acid red 52, C.I. acid red 87, C.I. acid red 92, C.I. acid red 289 or C.I. acid red 388 is used.
(there is the compound of phosphate or its salt)
As the compound with phosphate or its salt that colored filter red stain composition of the present invention uses, such as DISPERBYK-111, DISPERBYK-102, DISPERBYK-106 (Bi Ke chemistry Inc.), PLYSURFA212C, PLYSURFA215C, PLYSURFA208F, PLYSURFA208N, PLYSURFA208B, PLYSURFA219B, PLYSURFA210D, PLYSURFAL, PLYSURFAL12H (the first industrial pharmaceutical Inc.) etc. can be used.
In addition, the polymerizable compound with phosphate or its salt and the polymkeric substance other polymerizable compound being carried out copolymerization can also be used.As the polymerizable compound with phosphate or its salt, LightEsterP-1M, LightEsterP-2M (chemical company of common prosperity society system) etc. can be used.
In colored filter red stain composition of the present invention, there is the use amount of the compound of phosphate or its salt, relative to described dyestuff 100 mass parts, preferably 10 ~ 1000 mass parts, more preferably 50 ~ 500 mass parts.Relative to described dyestuff 100 mass parts, above-mentioned there is the compound of phosphate or its salt use amount or be less than 10 mass parts or more than 1000 mass parts time, sometimes the ageing stability of colored filter dye compositions becomes insufficient, in addition, the front and back of the rear baking operation in colored filter makes, brightness sometimes reduces.
In colored filter red stain composition of the present invention, there is the acid number preferably 10 ~ 300mgKOH/g of the compound of phosphate or its salt, more preferably 30 ~ 250mgKOH/g, further preferred 50 ~ 200mgKOH/g.Above-mentioned when there is the acid number of the compound of phosphate or its salt or be less than 10mgKOH/g or be greater than 300mgKOH/g, sometimes the ageing stability of colored filter dye compositions becomes insufficient, in addition, the front and back of the rear baking operation in colored filter makes, brightness sometimes reduces.
(pigment dispersing agent)
As the pigment dispersing agent that colored filter red stain composition of the present invention uses, the pigment dispersing agent used in colored filter field since can using in the past.
In colored filter red stain composition of the present invention, the use amount of pigment dispersing agent is relative to coloring pigment 100 mass parts, preferably 1 ~ 100 mass parts, more preferably 1 ~ 60 mass parts.When the content of above-mentioned pigment dispersing agent is less than 1 mass parts, pigment dispersion effect can reduce sometimes, on the other hand, when more than 100 mass parts, has the possibility of resulting visualization reduction etc.
As pigment dispersing agent, include, for example following material.
(1) polyamino compound (such as, polyarylamine, polyvinylamine, tygon gather poly-(rudimentary) alkylene amines of imines etc.) etc.) amino and/or imino group and be selected from there is free carboxy polyester, polyamide and polyesteramide in the resultant of reaction of at least a kind.
(2) there is at least each 1 in molecule and be selected from the side chain of at least a kind and the carbodiimides of Basic nitrogen-containing groups in polyester side chains, polyether lateral chain and polypropylene side chain.
(3) resultant of reaction of the low molecule amines gathering (rudimentary) alkylene imine, the two propyl group amine of methyl-imino etc. and the polyester with free carboxyl.
(4) make the alcohols of methoxy poly (ethylene glycol) etc., caprolactone polyester etc. have the polyesters of 1 hydroxyl, the compound with the isocyanate group reactive functional groups of 2 ~ 3, the aliphatics with isocyanate group reactive functional groups and tertiary amino or hetero ring type hydrocarbon compound and polyisocyanate compounds isocyanate group react successively and the resultant of reaction obtained.
(5) in the polymkeric substance of acrylate with alcohol hydroxyl group, the resultant of reaction that polyisocyanate compounds reacts with the hydrocarbon compound with amino is made.
(6) addition polyether chain and the resultant of reaction obtained in low molecule amines.
(7) in the compound with isocyanate group, make to have amino compound reaction and the resultant of reaction that obtains.
(8) in polyepoxides, the resultant of reaction of the linear polymer making to have free carboxyl and the reaction of the organic amine compound with 1 secondary amino group.
(9) one-side ends has the polycarbonate compound of functional group and the resultant of reaction of polyamino compound that can react with amino.
(10) methyl methacrylate is selected from, ethyl methyl acrylate, propylacrylate methyl esters, butyl methacrylate, sterylacrylic acid methyl esters, benzyl acrylic methyl esters, methacrylate (methylacrylate), ethyl propylene acid esters, propyl acrylate, butyl propyleneglycol acid esters, sterylacrylic acid ester, at least a kind and acrylamide in the methacrylate (methacrylicacidester) of benzyl acrylate etc. or acrylate, Methacrylamide, N-methylol amide, vinyl imidazole, vinylpyridine, there is at least a kind and the styrene containing in the polymerizable monomer of basic group of the monomer of amino and polycaprolactone skeleton etc., styrene derivative, the multipolymer of at least a kind in other polymerizable monomer.
(11) acrylic block copolymer etc. be made up of with the block without basic functionality the block of the basic group with tertiary amino, quaternary ammonium base etc.
(12) in polyarylamine, polycarbonate compound is made to carry out Michael addition reaction and the pigment dispersing agent obtained.
(13) there is the carbodiimides of at least each 1 polybutadiene chain and Basic nitrogen-containing groups.
(14) there is at least each 1 in molecule and there is the side chain of amide group and the carbodiimides of Basic nitrogen-containing groups.
(15) there is the Component units containing ethylene oxide chain and epoxypropane chain and there is the polyurethanes compound of the quaternised amino by quaternizing agent.
(16) isocyanate group in molecule with the isocyanate compound of chlorinated isocyanurates ring with there is reactive hydrogen base in molecule and there is the reactive hydrogen radical reaction of the compound of carbazole ring and/or azobenzene skeleton and the compound that obtains, relative in the molecule of this compound from the isocyanate group of isocyanate compound and the total amount of the amino-formate bond generated by the reaction of isocyanate group and reactive hydrogen base and urea bond with chlorinated isocyanurates ring, the number of carbazole ring and azobenzene skeleton is the compound of 15 ~ 85%.
Now, as the method mainly resist method utilizing colored filter red stain composition to manufacture colored filter, the colored filter red stain composition that the colored filter red stain composition being later divided into the method beyond by resist method to use and resist method use, is described following the composition etc. that it contains separately.
[the colored filter red stain composition utilized beyond A. resist method]
The situation that colored filter red stain composition of the present invention is not anti-corrosion agent composition is described.
When the present invention is not colored filter red stain anti-corrosion agent composition, said composition does not have active energy ray-curable, forms primarily of pigment, the pigment dispersion aids with acidic-group, dyestuff, pigment dispersing agent, resin, the compound with phosphate or its salt and organic solvent.
As coloring pigment, the pigment dispersion aids with acidic-group, pigment dispersing agent, use above-mentioned coloring pigment, there is the pigment dispersion aids of acidic-group, pigment dispersing agent.
(resin)
As the resin that colored filter red stain composition of the present invention uses, can be used in transmissivity in the full wavelength region may of 400 ~ 700nm of visible region is the resin of more than 80%, preferably more than 95%.As these resins, there are heat-curing resin, thermoplastic resin, alkali soluble resin etc.These separately or can mix two or more and use.
This kind of resin-phase for the total solid composition of colored filter with red stain composition, with mass fraction, the total amount of resin that uses, the preferably scope of 5 ~ 94 quality %, more preferably 20 ~ 50 quality %.
As heat-curing resin, thermoplastic resin, such as, butyral resin, styrene-maleic acid copolymer, haloflex, chlorinated polypropylene, Polyvinylchloride, vinyl chloride vinyl acetate copolymer, polyvinyl acetate, polyurethane based resin, phenolics, vibrin, acrylic resin, alkyd resin, styrene resin, polyamide, rubber resin, thermoprene, epoxy resin, cellulose family, polybutadiene, polyimide resin, benzoguanamine resin, melamine resin, urea resin etc. can be enumerated.
About alkali soluble resin, describe in detail at colored filter red stain anti-corrosion agent composition place described later.
(organic solvent)
As the organic solvent for colored filter red stain composition of the present invention, specifically, the ether organic solvent of ethylene glycol monomethyl ether, ethylene glycol monomethyl ether, ethylene glycol monoisopropyl ether, ethylene glycol monobutyl ether, diethylene glycol monomethyl ether, TC, propylene glycol monomethyl ether, propylene glycol monoethyl, glycol monobutyl ether, diethylene glycol diethyl ether, diethylene glycol dimethyl ether, diethylene glycol methyl ethyl ether etc. can be illustrated; The ether based organic solvent of ethylene glycol monomethyl ether acetic acid ester, ethylene glycol monomethyl ether acetate, ethylene glycol monobutyl ether acetic acid esters, propylene glycol monomethyl ether, propylene glycol monoethyl acetic acid esters etc.; The organic solvent of ketone of methyl isobutyl ketone, cyclohexanone, 2-HEPTANONE, δ-butyrolactone etc.; The based organic solvent of 2 hydroxy propanoic acid methyl esters, 2 hydroxy propanoic acid ethyl ester, 2-hydroxy-2-methyl ethyl propionate, 3-methyl-3-methoxybutyl propionic ester, 3-methoxy methyl propionate, 3-methoxypropionate, 3-ethoxypropanoate, 3-ethoxyl ethyl propionate, ethoxy ethyl acetate, hydroxyl ethyl acetate, formic acid n-pentyl ester etc.; The alcohols solvent of methyl alcohol, ethanol, isopropyl alcohol, butanols etc.; The nitrogenous class organic solvent etc. of 1-METHYLPYRROLIDONE, DMF, DMA etc.These separately or can mix two or more and use.
Colored filter red stain composition of the present invention is primarily of pigment, the pigment dispersion aids with acidic-group, dyestuff, pigment dispersing agent, resin, the compound with phosphate or its salt and organic solvent composition, and these compositions account for 90 ~ 100 quality % in colored filter red stain composition.
(adjuvant that can add as required)
According to the autofrettage of colored filter dye compositions, can suitably use the various adjuvants such as hot polymerization inhibitor, ultraviolet light absorber, antioxidant.
(manufacture method of colored filter red stain composition of the present invention)
The method using above material resistant to lose the manufacture colored filter red stain composition that agent method does not use is described.
Obtain by the presence of under the existence of pigment dispersion aids (sulfonated bodies etc. of preferred C.I. paratonere 2) with acidic-group or not through potpourri that the C.I. paratonere 254 of micronize process, the pigment dispersion aids (sulfonated bodies etc. of preferred C.I. paratonere 2) with acidic-group, pigment dispersing agent, resin, the compound with phosphate or its salt, organic solvent, other adjuvant are as required formed.Use the various dispersion machines of roller mill, kneader, high-speed stirring apparatus, ball mill, bowl mill, sand mill, ultrasonic dispersing machine, high pressure dispersing machine etc. to carry out mixing, dispersion treatment in obtained potpourri, thus obtain colored filter red stain composition.
In above-mentioned manufacture method, be used under the existence of the pigment dispersion aids with acidic-group when the micronize pigment of micronize process, even if also can not manufacture containing the pigment dispersion aids with acidic-group when the dispersion of micronize pigment.
In addition, in above-mentioned manufacture method, resin, the compound with phosphate or its salt can add before mixing dispersion treatment and/or after mixing dispersion treatment.
[the colored filter red stain composition that B. resist method uses]
Next, being used as colored filter colorant to colored filter red stain composition of the present invention disperses the situation of anti-corrosion agent composition to be described.
When the present invention is colored filter red stain anti-corrosion agent composition, its composition has active energy ray-curable, for the anti-corrosion agent composition of theobromine video picture, primarily of pigment, dyestuff, the pigment dispersion aids with acidic-group, pigment dispersing agent, resin, the compound with phosphate or its salt and organic solvent composition, be the resin comprising alkali soluble resin and photopolymerizable compound as described resin.
As pigment, the pigment dispersion aids with acidic-group, pigment dispersing agent, use as mentioned above.
(alkali soluble resin as resin)
As the alkali soluble resin of the resin that colored filter red stain anti-corrosion agent composition of the present invention uses, as long as play a role as bonding agent relative to red pigment, and when manufacturing colored filter to imaging liquid used in its video picture treatment process, particularly preferably alkali imaging liquid has the alkali soluble resin of solubility, be not particularly limited, alkali soluble resin in the past can be used.Wherein, preferably there is the alkali soluble resin of carboxyl, particularly more preferably there is the ethylene unsaturated monomer of the carboxyl of more than 1 and other can the multipolymer of ethylene unsaturated monomer of copolymerization.
Specifically, acrylic acid can be enumerated, the ethylene unsaturated monomer with carboxyl of methacrylic acid etc. can the styrene of copolymerization with the ethylene unsaturated monomer be selected from having carboxyl, 2-hydroxyethylmethacry,ate, 2-hydroxyethylacrylate methyl esters, aryl-acrylic acid esters, aromatic substituted acrylic acid methyl esters, benzyl acrylate, benzyl acrylic methyl esters, cyclohexylacrylic ester, cyclohexylacrylic methyl esters, glyceryl mono acrylic ester, glyceryl methyl acrylate, N-phenylmaleimide, Group-capped Polystyrene Macromer, polymethylmethacrylate macromonomer, the monomer of phenolphthalein base epoxy diacrylate etc., the multipolymer of the ethylene unsaturated monomer of at least a kind in oligomer class.
As the acid number of the alkali soluble resin in the present invention, from the viewpoint of the preferably 50 ~ 300mgKOH/g of imaging characteristics.
In addition, the weight-average molecular weight of the alkali soluble resin in the present invention, usually from the viewpoint of imaging characteristics, in organic solvent deliquescent preferably 1,000 ~ 100,000.And in the present invention, the weight-average molecular weight of the above-mentioned alkali soluble resin weight-average molecular weight of polystyrene conversion for obtaining based on GPC.In the present invention, use Water2690 (water generation Inc.) as device, use PLGel5 μM of IXED-D (PolymerLaboratories Inc.) as chromatographic column.
The use amount of the alkali soluble resin in the present invention is 1 ~ 300 mass parts relative to used pigment 100 mass parts, preferably 10 ~ 200 mass parts.Now, when the use amount of alkali soluble resin is less than 1 mass parts, there is the possibility that imaging characteristics reduces.On the other hand, when more than 300 mass parts, because colorant concentration can relatively reduce, so have the possibility being difficult to reach aim colour density as film.
(forming the photopolymerizable compound of resin)
As the photopolymerizable compound that can form the resin that colored filter red stain anti-corrosion agent composition of the present invention uses, use in molecule have the monomer, oligomer etc. of more than 1 optical polymerism unsaturated link with identical photopolymerizable compound described in above-mentioned colored filter red stain composition.Optical polymerism unsaturated link refers to by the polymerisable unsaturated link of following effects: Photoepolymerizationinitiater initiater described later produces free radical, kation by the active energy ray of ultraviolet, electron ray etc. when decomposing.
The photopolymerizable compound that can form these resins can be used singly or two or more kinds in combination.In the present invention, the use amount of photopolymerizable compound relative to the total solid composition of colored filter in red stain anti-corrosion agent composition, in the scope of preferred 3 ~ 50 quality % of mass fraction.
(Photoepolymerizationinitiater initiater)
As the Photoepolymerizationinitiater initiater that the colored filter red stain anti-corrosion agent composition of display device of the present invention uses, as long as pass through irradiation ultraviolet radiation, the active energy ray of electron ray etc. can produce free radical, cationic Photoepolymerizationinitiater initiater, be not particularly limited, such as, benzophenone can be enumerated, N, N '-tetraethyl-4, 4 '-diaminobenzophenone, 4-methoxyl-4 '-dimethylamino benzophenone, benzil, 2, 2-diethoxy acetophenone, styrax, styrax methyl ether, benzoin isobutyl butyl ether, benzyl dimethyl ketal, Alpha-hydroxy isobutyl benzophenone, thioxanthones, CTX, 1-hydroxycyclohexyl phenyl ketone, tert-butyl group anthraquinone, 1-chloroanthraquinone, 2, 3-dichloroanthraquinone, 3-chloro-2-methyl anthraquinone, 2-EAQ, 1, 4-naphthoquinones, 1, 2-benzo anthraquinone, 1, 4-dimethyl anthraquinone, 2-benzene anthraquinone, 2-methyl isophthalic acid [4-(methyl mercapto) phenyl]-2-morpholinopropane-1-ketone, triazines Photoepolymerizationinitiater initiater etc.These Photoepolymerizationinitiater initiaters can be used singly or two or more kinds in combination.
In the present invention, the content of above-mentioned Photoepolymerizationinitiater initiater relative to the total solid composition in above-mentioned colored filter red stain anti-corrosion agent composition, in the scope of preferred 1 ~ 20 quality % of mass fraction.
(organic solvent)
As the organic solvent that colorant colored filter red stain anti-corrosion agent composition of the present invention uses, the organic solvent in the past used in the field of liquid crystal color filter resist compatibly can be used.Specifically, the boiling point under normal pressure (1.013 × 102kPa) is had to be the based organic solvent, ether organic solvent, ether based organic solvent, organic solvent of ketone, aromatic hydrocarbon based organic solvent, nitrogenous class organic solvent etc. of 100 ~ 220 DEG C.When a large amount of containing the organic solvent of boiling point more than 220 DEG C time, when film preliminary drying coating formed, there is organic solvent can not fully evaporate and residue in dry coating, thus the possibility that the thermotolerance of dry coating reduces.In addition, when a large amount of be less than the organic solvent of 100 DEG C containing boiling point time, exist and be difficult to without mottled and be coated with equably, thus the possibility of the film of surface smoothness excellence cannot be obtained.
As preferred solvent, specifically, the ether organic solvent of ethylene glycol monomethyl ether, ethylene glycol monomethyl ether, ethylene glycol monoisopropyl ether, ethylene glycol monobutyl ether, diethylene glycol monomethyl ether, TC, propylene glycol monomethyl ether, propylene glycol monoethyl, glycol monobutyl ether, diethylene glycol diethyl ether, diethylene glycol dimethyl ether, diethylene glycol methyl ethyl ether etc. can be illustrated; The ether based organic solvent of ethylene glycol monomethyl ether acetic acid ester, ethylene glycol monomethyl ether acetate, ethylene glycol monobutyl ether acetic acid esters, propylene glycol monomethyl ether, propylene glycol monoethyl acetic acid esters etc.; The organic solvent of ketone of methyl isobutyl ketone, cyclohexanone, 2-HEPTANONE, δ-butyrolactone etc.; The based organic solvent of 2 hydroxy propanoic acid methyl esters, 2 hydroxy propanoic acid ethyl ester, 2-hydroxy-2-methyl ethyl propionate, 3-methyl-3-methoxybutyl propionic ester, 3-methoxy methyl propionate, 3-methoxypropionate, 3-ethoxypropanoate, 3-ethoxyl ethyl propionate, ethoxy ethyl acetate, hydroxyl ethyl acetate, formic acid n-pentyl ester etc.; The nitrogenous class organic solvent etc. of 1-METHYLPYRROLIDONE, DMF, DMA etc.These can separately or two or more be used in combination.
In these organic solvents, in dissolubility, dispersiveness, coating etc., also preferred diethylene glycol dimethyl ether, diethylene glycol methyl ethyl ether, ethylene glycol monomethyl ether acetic acid ester, propylene glycol monomethyl ether, propylene glycol monoethyl acetic acid esters, cyclohexanone, 2-HEPTANONE, 2 hydroxy propanoic acid ethyl ester, 3-methyl-3-methoxybutyl propionic ester, 3-methoxypropionate, 3-ethoxypropanoate, formic acid n-pentyl ester etc., more preferably propylene glycol monomethyl ether.
From the viewpoint of the dispersiveness, coating etc. of the dissolubility of above-mentioned alkali soluble resin, coloring pigment, these organic solvents preferably contain more than 50 quality %, more preferably more than 70 quality % in colored filter red stain anti-corrosion agent composition of the present invention.
Colored filter red stain anti-corrosion agent composition of the present invention formed primarily of coloring pigment, the pigment dispersion aids with acidic-group, the polymer pigment dispersant with basic group, alkali soluble resin, photopolymerizable compound, Photoepolymerizationinitiater initiater, barium sulphate and organic solvent, and these compositions account for 90 ~ 100 quality % in colored filter red stain anti-corrosion agent composition.
(adjuvant that can add as required)
Colored filter red stain anti-corrosion agent composition of the present invention suitably can use the various adjuvants of hot polymerization inhibitor, ultraviolet light absorber, antioxidant etc. as required.
(manufacture method of colored filter red stain anti-corrosion agent composition of the present invention)
The method using above material to manufacture colored filter red stain anti-corrosion agent composition is described.Colored filter red stain anti-corrosion agent composition obtains by following manufacture method.
Obtain by the presence of under the existence of pigment dispersion aids (sulfonated bodies etc. of preferred C.I. paratonere 2) with acidic-group or not through potpourri that the C.I. paratonere 254 of micronize process, the pigment dispersion aids (sulfonated bodies etc. of preferred C.I. paratonere 2) with acidic-group, pigment dispersing agent, resin, the compound with phosphate or its salt, organic solvent, other adjuvant as required form.Use the various dispersion machines of roller mill, kneader, high-speed stirring apparatus, ball mill, bowl mill, sand mill, ultrasonic dispersing machine, high pressure dispersing machine etc. to carry out mixing, dispersion treatment in obtained potpourri, thus obtain colored filter red stain composition.Add photopolymerizable compound, Photoepolymerizationinitiater initiater, alkali soluble resin, organic solvent, other adjuvant as required further, thus obtain colored filter red stain anti-corrosion agent composition of the present invention.
In above-mentioned manufacture method, be used under the existence of the pigment dispersion aids with acidic-group when the micronize pigment of micronize process, even if also can not manufacture containing the pigment dispersion aids with acidic-group when the dispersion of micronize pigment.
In addition, in above-mentioned manufacture method, resin, dyestuff, the compound with phosphate or its salt can add when the making of dye compositions and/or after the making of dye compositions.
In addition, use colored filter red stain composition of the present invention as follows to the method manufacturing colored filter, its necessary device can be comprised, as the formation beyond this dye compositions, known method can be adopted to manufacture.
For the colored filter red stain composition with specific composition of the present invention, wherein as its color characteristic (x, y, Y), preferred colourity x is 0.6550.Preferred y is 0.322 ~ 0.330, more preferably 0.322 ~ 0.324.More preferably be more than 12.2, particularly preferably more than 13.0 as the Y value of lightness further.When this scope, can further improve colouring power and/or brightness.
Embodiment
Below enumerate embodiment and in further detail the present invention is described, but the present invention is not limited to these embodiments.And when not having special declaration, " % " refers to the meaning of " quality % ".
< pigment dispersion aids >
(sulfonated bodies of pigment dispersion aids A:C.I. paratonere 2)
In 100ml Erlenmeyer flask, add the 30ml concentrated sulphuric acid, by magnetic stirrer while drop into 10 mass parts C.I. paratoneres 2, at room temperature stir 30 minutes.In 1L beaker, load the potpourri of 50 mass parts water and 50 mass parts ice, above-mentioned reactant is poured in this frozen water, by magnetic stirrer 30 minutes.It is under reduced pressure filtered washing, and by obtained solid drying, thus obtain the pigment dispersion aids A of 12 mass parts.
< is through the pigment > of micronize process
(micronize pigment A: the C.I. paratonere 254 through TRI-MIX process)
Sodium chloride, the 1920 mass parts diethylene glycols of 800 mass parts C.I. paratonere 254,8000 mass parts particle diameter 20 μm are dropped in the still of TRI-MIXTX-15 (trade name, aboveground making is made).In the scope of 70% becoming load current value 9.3A, and 45 DEG C carry out 3 hours mixing and carry out salt mill process.Next, the obtained mixing thing of 1300 mass parts is dropped in the warm water of 3 liters, and 70 DEG C of heating while stirring becomes pulpous state in 1 hour.Repeatedly filter, wash removing sodium chloride and diethylene glycol after, at 40 DEG C of dry diels, thus obtain the micronize pigment A of 95 mass parts.
(pigment dispersing agent)
BYK-LPN21116 (Bi Ke chemistry Inc., acrylic polymer zoarium, amine value 29)
(there is the compound of phosphate or its salt)
BYK-111 (Bi Ke chemistry Inc., the multipolymer containing phosphate, acid number 136, nonvolatile component 95%)
BYK-102 (Bi Ke chemistry Inc., the multipolymer containing phosphate, acid number 102, nonvolatile component 99%)
BYK-106 (salt, acid number 145, the nonvolatile component 91% of Bi Ke chemistry Inc., multipolymer containing phosphate)
Phosphorous acidic group Resin A (benzyl acrylic methyl esters/acidifying phosphoric acid 2-methacryloxyethyl ester (2-methacryloyloxyethylacidulatedphosphate) multipolymer, acid number 50mgKOH/g, weight-average molecular weight: 10,000)
Phosphorous acidic group resin B (benzyl acrylic methyl esters/acidifying phosphoric acid 2-methacryloxyethyl ester copolymer, acid number 200mgKOH/g, weight-average molecular weight: 10,000)
Phosphorous acidic group resin C (benzyl acrylic methyl esters/acidifying phosphoric acid 2-methacryloxyethyl ester copolymer, acid number 20mgKOH/g, weight-average molecular weight: 10,000)
Phosphorous acidic group resin D (benzyl acrylic methyl esters/acidifying phosphoric acid 2-methacryloxyethyl ester copolymer, acid number 300mgKOH/g, weight-average molecular weight: 10,000)
(resin)
Alkali soluble resin A (benzyl acrylic methyl esters/methacrylic acid copolymer, acid number 120mgKOH/g, weight-average molecular weight: 25,000)
(organic solvent)
PGME: propylene glycol monomethyl ether
PGMEA: propylene glycol monomethyl ether
DAA: diacetone alcohol
(photopolymerizable compound)
DPEHA: dipentaerythritol acrylate
(Photoepolymerizationinitiater initiater)
Gorgeous good solid 369:2-benzyl-(dimethylamino)-1-(4-morpholinyl phenyl)-1-butanone
< colored filter red stain composition >
By above-mentioned micronize process pigment, the pigment dispersion aids with acidic-group, pigment dispersing agent, alkali soluble resin, dyestuff, the compound with phosphate or its salt and the organic solvent composition according to table 1; mixing 6 hours of the zirconium oxide bead paintconditioner of use 0.2mm Φ, thus obtain colored filter red stain composition 1 ~ 15.
Table 1
The colored filter red stain composition > that the resist method of < embodiment 1 ~ 10 and comparative example 1 ~ 5 uses
In order to become the pigment proportion of table 2, Homogeneous phase mixing colored filter red stain resist raw material, thus the colored filter red stain composition that the resist method obtaining embodiment 1 ~ 10 and comparative example 1 ~ 5 uses.
Table 2
(evaluation)
< dispersion stabilization >
For the colored filter red stain composition that the resist method of embodiment 1 ~ 10 and comparative example 1 ~ 5 uses, gather it into vial respectively, its state sternly, is evaluated according to following evaluation criterion after 7 days in room temperature preservation by plug.Result is as shown in table 2.
Zero: all do not find thickening, sediment.
△: the thickening, the sediment that recover degree originally when finding that there is vibration gently.
×: find that there is thickening, sediment that intense oscillations does not recover degree originally yet.
The color characteristic of colored filter red stain composition that < resist method uses and the evaluation > of brightness sustainment rate
The colored filter red stain composition resist method of embodiment 1 ~ 10 and comparative example 1 ~ 5 used uses sol evenning machine (spincoater) coating on the glass substrate.
Next, expose with high-pressure sodium lamp after 3 minutes at 100 DEG C of preliminary dryings, dry 2 hours after 230 DEG C further.Next, the color characteristic (x, y, Y) of each resist of embodiment 1 ~ 10 and comparative example 1 ~ 5 is measured with spectrophotometer (Inc. of Shimadzu Seisakusho Ltd., UV-2500PC, illuminant-C 2 ° of visuals field).In embodiment 1 ~ 10 and comparative example 1 ~ 3, try to achieve thickness, luminance y value when colourity x=0.6550, y=0.3230.
In addition, brightness sustainment rate defines as follows.
Brightness sustainment rate (%)=(brightness after pre-baked brightness/rear baking) × 100
Result according to above-mentioned table 2, according to the embodiment 1 ~ 10 as colored filter red stain composition of the present invention, while the brightness excellence of colored filter red stain composition of the present invention, brightness sustainment rate is also excellent, even if that is, can obtain through after dry the also little colored filter red stain composition of change of process brightness.
In addition, according to the embodiment 1 ~ 10 as colored filter red stain composition of the present invention, the colored filter red stain composition of brightness sustainment rate excellence can be obtained.
But, according to have phosphate or its salt compound acid number deficiency comparative example 1, have the acid number surplus of the compound of phosphate or its salt comparative example 2, not containing have phosphate or its salt compound comparative example 3 and there is the comparative example 4 of content surplus of compound of phosphate or its salt, become the result that dispersion stabilization and brightness maintain rate variance.
According in colored filter red stain composition of the present invention not containing the comparative example 5 of dyestuff, become the result that the good but brightness of dispersion stabilization maintains rate variance.
According to such result, known the present invention, by becoming the colored filter red stain composition of specific composition, can reach dispersion stabilization and brightness excellent, though through after dry the also little effect of the change that processes brightness.
Claims (5)
1. a colored filter red stain composition, it forms primarily of pigment, the pigment dispersion aids with acidic-group, dyestuff, pigment dispersing agent, resin, the compound with phosphate or its salt and organic solvent, it is characterized in that, described pigment has pyrrolo-pyrrole-dione skeleton, and described dyestuff is be selected from least a kind in C.I. acid red 52, C.I. acid red 87, C.I. acid red 92, C.I. acid red 289 and C.I. acid red 388.
2. colored filter red stain composition according to claim 1, is characterized in that, described in there is the compound of phosphate or its salt acid number be 10 ~ 300mgKOH/g.
3. colored filter red stain composition according to claim 1 and 2, is characterized in that, described in there is the compound of phosphate or its salt content be 10 ~ 1000 mass parts relative to described dyestuff 100 mass parts.
4. the red stain composition of the colored filter according to any one of claims 1 to 3, is characterized in that, described pigment is the pigment through micronize process.
5. the red stain composition of the colored filter according to any one of Claims 1 to 4, is characterized in that, described in there is the pigment dispersion aids of acidic-group for having sulfonic pigment dispersion aids.
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| JP2014-161497 | 2014-08-07 | ||
| JP2014161497A JP6543444B2 (en) | 2014-08-07 | 2014-08-07 | Red colorant composition for color filter |
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| CN108459467A (en) * | 2017-02-17 | 2018-08-28 | 住友化学株式会社 | Red colored composition |
| CN110563691A (en) * | 2018-06-06 | 2019-12-13 | 日本化药株式会社 | Dibenzopyran compound, pigment composition, color resist, color filter, and ink composition for inkjet |
| CN112210230A (en) * | 2019-07-10 | 2021-01-12 | 阪田油墨股份有限公司 | Dye dispersion composition for color filter and dye dispersion resist composition for color filter |
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| KR20160018357A (en) | 2016-02-17 |
| CN105372936B (en) | 2023-08-04 |
| KR102425989B1 (en) | 2022-07-26 |
| JP2016038463A (en) | 2016-03-22 |
| TW201609990A (en) | 2016-03-16 |
| TWI659070B (en) | 2019-05-11 |
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