CN1928714A - Black photosensitive resin composition - Google Patents
Black photosensitive resin composition Download PDFInfo
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- CN1928714A CN1928714A CNA200610106273XA CN200610106273A CN1928714A CN 1928714 A CN1928714 A CN 1928714A CN A200610106273X A CNA200610106273X A CN A200610106273XA CN 200610106273 A CN200610106273 A CN 200610106273A CN 1928714 A CN1928714 A CN 1928714A
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- resin composition
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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
- G03F7/004—Photosensitive materials
- G03F7/0045—Photosensitive materials with organic non-macromolecular light-sensitive compounds not otherwise provided for, e.g. dissolution inhibitors
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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
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- Spectroscopy & Molecular Physics (AREA)
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Abstract
The invention provides a black photosensitive resin composition forming an insulating film, and to further provide a black photosensitive resin composition forming a film which takes on a more desirable black color and gives a more preferable pattern shape. In the black photosensitive resin composition containing a pigment component that contains black pigment, the pigment component comprises an insulating organic pigment.
Description
Technical field
The present invention relates to be applicable to the black-colored photosensitive resin composition of the colored filter of making LCD etc. or black matrix etc.
Background technology
Black-colored photosensitive resin composition is an integral material in the manufacturing of display elements such as colored filter, liquid crystal display material, organic electroluminescent (EL) display panel material.For example, in the colored filter that various multicolor displaying bodies such as colour liquid crystal display device have, show contrast or color developing effect in order to improve, boundary member between R (red), G (green), B dyed layers such as (indigo plants) must have black matrix, and this black matrix is formed by black-colored photosensitive resin composition.
About black matrix, there is following document.Disclose a kind of black matrix material that contains the cobalt/cobalt oxide class as black pigment in the patent documentation 1, this black matrix material is used to obtain the black matrix that degree of blackness is high and have insulativity.A kind of material is disclosed in the patent documentation 2, this material is used for driving at thin film transistor (TFT) (TFT) mode color liquid crystal display arrangement and forms sept (spacer) and/or black matrix on substrate, make that the erosion ratio of the pattern that forms is little, pattern form is difficult for becoming anti-taper during development, the cloth that can prevent from effectively to rub hangs over peeling off of pattern part and pattern, and does not produce poor display such as fluorescent screen images reservation.The black matrix material of using the perylene compounds is disclosed in the patent documentation 3.A kind of black matrix material is disclosed in the patent documentation 4, it is used to form the high-insulativity photomask with high shading rate, should black matrix material contain light screening materials such as insulativity organic pigment and carbon black, described insulativity organic pigment contains the colour mixture organic pigment of pseudo-blackization.
In addition, in recent years, black matrix material can be as the photonasty sept (photo spacer) that is used to refer to the electrode base board interval that exists in the mode that clips liquid crystal layer.At this moment, requiring the photonasty sept is insulativity.In the liquid crystal panel association area, have and use the black-colored photosensitive sept to improve the technology of pixel contrast to replace bead sept (beads spacer).
In addition, for the organic EL panel element, between pixel and pixel, also insulation course must be arranged.In the relevant field of organic EL panel, there is the grid (black matrix) that forms black to improve the technology of light-proofness.
[patent documentation 1] spy opens the 2002-47423 communique
[patent documentation 2] spy opens the 2002-365795 communique
[patent documentation 3] spy opens flat 6-289602 communique
No. 2552391 communique of [patent documentation 4] patent
Summary of the invention
But,,, be difficult to as photonasty sept or insulating material because resistance is little for the carbon pigment-dispersing type photosensitive polymer combination of present main flow.Therefore, described in patent documentation 1～4, if use the mineral compound conduct black matrix material of resistance less than organic compound, then its insulativity is inadequate.In addition, in the patent documentation 3,4,, in addition also contain, so its insulativity is inadequate such as mineral-type compounds such as carbon blacks though use perylene black as the organic class pigment of black.
In addition, even use red-indigo plant-green-green grass or young crops-fuchsin-Huang-pink organic pigment that waits, the shading of luminous ray also is inadequate, is necessary to improve the content of the pigment total amount in the pigment-dispersing type photosensitive composite.But,, can not improve contrast so the remarkable variation of sensitivity and development can not obtain satisfied black matrix pattern shape because with respect to the pigment-dispersing type photoresist, the ratio of pigment relatively increases.
In view of the above problems, the invention provides the black-colored photosensitive resin composition that forms the film with insulativity, following black-colored photosensitive resin composition further is provided, its formed film more preferably is rendered as black, pattern form is good.
The black-colored photosensitive resin composition of the pigment composition that contains black pigment described in the present invention is characterised in that above-mentioned pigment composition contains the insulativity organic pigment.
By formation like this, the film that is formed by this black-colored photosensitive resin composition can have insulativity.
In addition, the above-mentioned black pigment of the black-colored photosensitive resin composition described in the present invention is characterised in that it is that perylene is black.
By formation like this, can not use the mineral compound of electric conductivity and use the insulativity organic material, thereby can have insulativity by the film that this black-colored photosensitive resin composition forms.
The above-mentioned pigment composition of the black-colored photosensitive resin composition described in the present invention is characterised in that it contains organic red pigment and blue organic pigment.
By formation like this, can improve the degree of the black that pigment composition presented that contains black pigment, can improve contrast.
In addition, the specific inductive capacity of the film that is formed by described black-colored photosensitive resin composition among the present invention is characterised in that it is smaller or equal to 7.
By formation like this, can obtain the insulativity of realistic scale.
In addition, the optical density (OD) of the film that is formed by above-mentioned black-colored photosensitive resin composition described in the present invention is characterised in that, with respect to the thickness of the film of per 1 μ m, optical density (OD) is more than or equal to 1.
By formation like this, the film that is formed by above-mentioned black-colored photosensitive resin composition has high light-proofness.
In addition, the above-mentioned black-colored photosensitive resin composition described in the present invention is characterised in that it contains optical polymerism compound, Photoepolymerizationinitiater initiater and solvent.
By formation like this, can obtain the minus black-colored photosensitive resin composition.
With respect to the total weight of above-mentioned optical polymerism compound, above-mentioned Photoepolymerizationinitiater initiater and the above-mentioned solvent that above-mentioned black-colored photosensitive resin composition contained described in the present invention, the content ratio of above-mentioned pigment composition is 20 weight %～250 weight %.
By formation like this, in the scope of this weight ratio, can obtain best shading rate and pattern form.
In addition, forming black matrix by black-colored photosensitive resin composition of the present invention also is one of feature.
By formation like this, can obtain high-contrast.
In addition, above-mentioned black matrix being used for organic electroluminescent (EL) display panel also is one of feature.
By formation like this, can obtain having organic electroluminescent (EL) display of higher contrast.
In addition, above-mentioned black matrix being used for display panels also is one of feature.
By formation like this, can obtain having the display panels of higher contrast.
In addition, forming the photonasty sept by black-colored photosensitive resin composition of the present invention also is one of feature.
By formation like this, can be used as the photonasty sept by the film that black-colored photosensitive resin composition forms.
In addition, above-mentioned photonasty sept being used for display panels also is one of feature.
By formation like this, the film that can obtain that black-colored photosensitive resin composition is formed is used as the display panels of photonasty sept.
The application of the invention can form the black photosensitive resin film with high-insulativity.In addition, can form the preferred black photosensitive resin film that is rendered as black, has high light-proofness.
Embodiment
Hereinafter embodiments of the present invention are described in detail.
Black-colored photosensitive resin composition in the present embodiment contains optical polymerism compound, Photoepolymerizationinitiater initiater, pigment, solvent.And this pigment does not contain electric conductivity black pigments such as carbon black, and contains the insulativity organic pigment that is rendered as black.Further, except this insulativity organic pigment, also can contain organic red pigment and/or blue organic pigment, in addition, can also contain the organic pigment of colors such as presenting yellow, purple as pigment.
In the above-mentioned black-colored photosensitive resin composition, with respect to the total weight of above-mentioned optical polymerism compound, above-mentioned Photoepolymerizationinitiater initiater and above-mentioned solvent, the content ratio of above-mentioned pigment composition is 20 weight %～250 weight %.Thickness that the ratio of this pigment composition can be when using the film that is formed by black-colored photosensitive resin composition or the shading rate of necessity and change.If above-mentioned pigment composition ratio is less than 20 weight %, then shading rate becomes minimum.In addition,, can not get sufficient sensitivity during exposure, can not obtain satisfied pattern form if above-mentioned pigment composition ratio greater than 250 weight %, says on the whole that then the cross-linked structure of resin tails off.
Above-mentioned optical polymerism compound is the optical polymerism compound that can become alkali soluble resin, shown in following general formula (1).
[general formula (1)]
In the above-mentioned general formula (1), n is 1～20 integer,
Y is the residue behind the anhydride group removed of dicarboxylic anhydride,
Z is the residue behind the anhydride group removed of tetrabasic carboxylic acid dicarboxylic anhydride,
X is the group shown in the following general formula (2),
[general formula (2)]
In the general formula (2), R
1, R
2Be H, CH
3Or the group shown in the following general formula (3),
[general formula (3)]
In the general formula (3), R
3Be H or CH
3
Wherein, described " anhydride group " is " CO-O-CO-group ".
In addition,, for example can enumerate maleic anhydride, succinic anhydride, itaconic anhydride, anhydride phthalic acid, tetrahydrochysene anhydride phthalic acid, six hydrogen anhydride phthalic acids, methyl bridging methylene tetrahydrochysene anhydride phthalic acid, chlorendic anhydride, methyl tetrahydrochysene anhydride phthalic acid, glutaric anhydride etc. as dicarboxylic anhydride.
In addition,, for example can enumerate aromatic series polybasic acid anhydrides such as pyromellitic acid anhydride, benzophenone tetrabasic carboxylic acid dicarboxylic anhydride, biphenyltetracarboxyacid acid dicarboxylic anhydride, biphenyl ether tetrabasic carboxylic acid dicarboxylic anhydride as the tetrabasic carboxylic acid dicarboxylic anhydride.
Optical polymerism compound shown in the above-mentioned general formula (1) can be opened the described method of 2001-354735 communique by the spy and obtain.Optical polymerism compound shown in the general formula (1) does not have the dicarboxylic anhydride residue in fact in polymeric chain, thereby with polymeric chain in to have a compound of dicarboxylic anhydride residue different, even the solid component concentration of the two is identical, the solution viscosity that also is still the optical polymerism compound shown in the general formula (1) control that more is easy to get, improves coating characteristics and makes the thickness homogenization of film at the operation in the time of can seeking to improve coating.
In addition, for the optical polymerism compound shown in the above-mentioned general formula (1), in compound, have at least 2 can addition polymerization the ethylene type unsaturated double-bond, when photosensitive polymer combination is subjected to making the irradiation of light of provision wavelengths of Photoepolymerizationinitiater initiater activation, optical concentration raises, can by Photoepolymerizationinitiater initiater be used for carrying out addition polymerization, thereby solidify.Say it on the contrary, when forming the black matrix pattern of colored filter of LCD etc.,, then can increase the content of black pigment, improve light-proofness if use photosensitive polymer combination of the present invention.Therefore, can make and show contrast height and R, G, the colored filter that it is good that B develops the color.
Preferably in above-mentioned photosensitive polymer combination, further add compound with ethylene type unsaturated double-bond that can addition polymerization.
" compound " (hereinafter referred to as " ethylene type compound ") herein with ethylene type unsaturated double-bond that can addition polymerization, be when photosensitive polymer combination is subjected to the irradiation of light of provision wavelengths, carry out the compound that addition polymerization is solidified by the effect of Photoepolymerizationinitiater initiater with at least 1 ethylene type unsaturated double-bond, be monomer, or have the polymkeric substance of ethylene type unsaturated double-bond on side chain or the main chain with above-mentioned ethylene type unsaturated double-bond.In addition, above-mentioned monomer is the notion that is different from so-called polymer substance, not only refers to " monomer " of narrow sense, also comprises dimer, tripolymer, oligomer.
As above-mentioned monomer, for example can enumerate unsaturated carboxylic acid; The ester of aliphatics (many) hydroxyl compound and unsaturated carboxylic acid; The ester of aromatic series (many) hydroxyl compound and unsaturated carboxylic acid; The ester that esterification by multi-hydroxy compounds such as unsaturated carboxylic acid and polybasic carboxylic acid and above-mentioned aliphatics (many) hydroxyl compound, aromatic series (many) hydroxyl compound obtains; The unsaturated carboxylic acid acid amides; Unsaturated carboxylic acid nitrile etc.
Particularly, can use following substances: methyl acrylate; Methyl methacrylate; Ethyl acrylate; Jia Jibingxisuanyizhi; Isobutyl acrylate; Isobutyl methacrylate; Acrylic acid 2-hydroxy methacrylate; 2-hydroxyethyl methacrylate; The glycol monomethyl methyl ether acrylate; The glycol monomethyl methyl ether methacrylate; The ethylene glycol monomethyl ether acrylate; The ethylene glycol monomethyl ether methacrylate; Acrylic acid glyceride; Glyceral methacrylate; Acrylamide; Methacrylamide; Vinyl cyanide; Methacrylonitrile; 2-EHA; Methacrylic acid 2-Octyl Nitrite; Benzyl acrylate; Benzyl methacrylate; Ethylene glycol diacrylate; The diacrylate binaryglycol ester; Ethylene glycol dimethacrylate; The diacrylate triglycol ester; The dimethacrylate triglycol ester; Diacrylate TEG ester; Dimethacrylate TEG ester; Tetramethylene dimethacrylate; The diacrylate propylene glycol ester; The dimethyl allene acid propylene glycol ester; The trimethylolethane trimethacrylate acrylate; The trimethylolethane trimethacrylate methacrylate; Trimethylolpropane triacrylate; Trimethylol-propane trimethacrylate; Tetra methylol propane tetraacrylate; Tetra methylol propane tetramethyl acrylate; Pentaerythritol triacrylate; Pentaerythritol acrylate trimethyl; Tetramethylol methane tetraacrylate; Pentaerythrite tetramethyl acrylate; Dipentaerythritol five acrylate; Dipentaerythritol pentamethyl acrylate; Dipentaerythritol acrylate; Dipentaerythritol hexamethyl acrylate; 1,6 hexanediol diacrylate; 1, the 6-hexanediol dimethacrylate; Carbon epoxy radicals diacrylate (カ Le ボ エ Port キ シ ジ ア Network リ レ one ト); Carbon epoxy radicals dimethylacrylate (カ Le ボ エ Port キ シ ジ メ Network リ レ one ト); The compound that the acrylate of these compounds of enumerating or methacrylate is replaced with fumarate, maleate, crotonates, itaconate and obtain; Acrylic acid; Methacrylic acid; Fumaric acid; Maleic acid; Crotonic acid; Itaconic acid; The p-dihydroxy-benzene mono acrylic ester; The hydroquinone monomethyl acrylate; Hydroquinone diacrylate; The p-dihydroxy-benzene dimethylacrylate; The resorcinol diacrylate; The resorcinol dimethylacrylate; The pyrogallol diacrylate; The pyrogallol triacrylate; The condensation product of acrylic acid and phthalandione and diethylene glycol; The condensation product of acrylic acid and maleic acid and diethylene glycol; The condensation product of methacrylic acid and terephalic acid and pentaerythrite; The condensation product of acrylic acid and hexane diacid and butylene glycol and glycerine; The ethylene acrylamide; The ethylene Methacrylamide; The allyl ester of diallyl phthalate; Phthalandione divinyl ester etc.
In addition,, for example can enumerate the polyester that the polycondensation reaction by unsaturated dicarboxylic acid and dihydroxy compounds obtains as the polymkeric substance that on side chain or main chain, has the ethylene type unsaturated double-bond; The polyamide that polycondensation reaction by unsaturated dicarboxylic acid and diamines obtains; The polyester that polycondensation reaction by itaconic acid, propylidene succinic acid, ethylidene malonic acid and dihydroxy compounds obtains; The polyamide that polycondensation reaction by itaconic acid, propylidene succinic acid, ethylidene malonic acid and diamines obtains; Phenol phenolic epoxy acrylate; Phenol phenolic epoxy methacrylate; Cresols phenolic epoxy acrylate; Cresols phenolic epoxy methacrylate; Bisphenol-a epoxy acrylate; Bisphenol S type epoxy acrylate; Urethane acrylate oligomer; Urethane methacrylate oligomers etc.Also can be further to make the reaction of multi-anhydride and above-mentioned epoxy (methyl) acrylate resin and the polymkeric substance that obtains.In addition, can also use and on side chain, have the polymkeric substance that hydroxyl or halogenated alkyl etc. have the functional group of reactivity, for example, make polymkeric substance that polyvinyl alcohol (PVA), poly-(2-hydroxyethyl methacrylate), Hydrin etc. and unsaturated carboxylic acids such as acrylic acid, methacrylic acid, fumaric acid, maleic acid, crotonic acid, itaconic acid obtain by high molecular weight reactive etc.Wherein, especially preferably use the monomer of acrylate or methacrylate.
Above-mentioned ethylene type compound when photosensitive polymer combination is subjected to the irradiation of light of defined wavelength, carries out addition polymerization with the optical polymerism compound of above-mentioned general formula (1).So, can form the crosslinked structure of composition in its entirety.
As among the present invention the Photoepolymerizationinitiater initiater that can use; for example can enumerate; 2; 2-two (2-chlorphenyl)-4; 5; 4 '; 5 '-tetraphenyl-1; 2 '-bisglyoxaline (hereinafter; be called B-CIM (protecting the chemical society of native ケ paddy system)); the 1-hydroxycyclohexylphenylketone; 2; 2-dimethoxy-1; 2-diphenylethane-1-ketone; 2-methyl isophthalic acid-[4-(methyl sulfenyl) phenyl]-2-morpholino propane-1-ketone; 2-benzyl-2-dimethylamino-1-(4-morpholino phenyl)-butane-1-ketone; 2-hydroxy-2-methyl-1-phenyl-propane-1-ketone; 2; 4; 6-trimethylbenzene formyl diphenyl phosphine oxide; 1-[4-(2-hydroxyl-oxethyl) phenyl]-2-hydroxy-2-methyl-1-propane-1-ketone; 2; the 4-diethyl thioxanthone; 2; 4-dimethyl thioxanthones; 3; 3-dimethyl-4-methoxy benzophenone; benzophenone; the 2-chlorobenzophenone; 4; 4 '-two dimethylamino benzophenone (michaelis ketone hereinafter referred to as; Michler ' s ketone); 4; 4 '-two diethylamino benzophenone are (hereinafter; be called EAB-F (protecting the chemical society of native ケ paddy system)); 1-(4-isopropyl phenyl)-2-hydroxy-2-methyl propane-1-ketone; 1-(4-dodecylphenyl)-2-hydroxy-2-methyl propane-1-ketone; 4-benzoyl-4 '-methyl dimethoxy base thioether; 4-dimethylamino benzoic acid; 4-dimethylamino benzoic acid methyl esters; 4-dimethylamino ethyl benzoate; 4-dimethylamino benzoic acid butyl ester; 4-dimethylamino benzoic acid-2-Octyl Nitrite; 4-dimethylamino benzoic acid-2-isopentyl ester; acetophenone; 2; the 2-diethoxy acetophenone; to dimethyl acetophenone; to the dimethylamino propiophenone; trichloroacetophenone; p-tert.-butyl acetophenone; benzyl dimethyl ketal; benzyl-'beta '-methoxy ethyl acetal; 1-phenyl-1; 2-propanedione-2-(adjacent ethoxy carbonyl) oxime; o-benzoyl benzoic acid methyl esters; two (4-dimethylaminophenyl) ketone; 4; 4 '-two diethylamino benzophenone; benzil; benzoin; benzoin methyl ether; the benzoin ethylether; the benzoin isopropyl ether; the benzoin n-butyl ether; the benzoin isobutyl ether; the benzoin butyl ether; to the dimethylamino benzoylformaldoxime; thioxanthones; 2-methyl thioxanthones; the 2-isopropyl thioxanthone; Dibenzosuberone; α; α-Er Lv-4-Ben Yangjibenyitong; 4-dimethylaminobenzoic acid pentyl ester; and 2; 4-two (trichloromethyl)-6-(3-bromo-4-methoxyl) phenyl-s-triazine; 2,4-two (trichloromethyl)-6-(to methoxyl) styryl-triaizine compounds such as s-triazine etc.
In addition,, can also use thioxanthones, 2-clopenthixal ketone, 2, sulphur compounds such as 4-diethyl thioxanthene, 2-methyl thioxanthene, 2-isopropyl thioxanthene except above-mentioned; 2-EAQ, prestox anthraquinone, 1,2-benzo anthraquinone, 2, anthraquinone classes such as 3-diphenyl anthraquinone; Organic peroxides such as azoisobutyronitrile, benzoyl peroxide, cumene peroxide; Mercaptan compounds such as 2-mercaptobenzimidazole, 2-mercaptobenzoxazole, 2-mercaptobenzothiazole etc.
Can use a kind of these Photoepolymerizationinitiater initiater separately, also can use at least 2 kinds combination of these Photoepolymerizationinitiater initiaters.Especially, B-CIM and EAB-F can preferably use separately, also can preferably use the combination of B-CIM and EAB-F and other Photoepolymerizationinitiater initiaters.
As concrete combination, for example can enumerate the combination of B-CIM and 2-methyl isophthalic acid-[4-(methyl sulfenyl) phenyl]-2-morpholino propane-1-ketone or 2-benzyl-2-dimethylamino-1-(4-morpholino phenyl)-butane-1-ketone; B-CIM and 2,4-two (trichloromethyl)-6-(3-bromo-4-methoxyl) phenyl-s-triazine or 2, the combination of 4-two (trichloromethyl)-6-(to methoxyl) styryl-s-triazine; B-CIM, 2-methyl-[4-(methyl sulfenyl) phenyl]-2-morpholino propane-1-ketone or 2-benzyl-2-dimethylamino-1-(4-morpholino phenyl)-butane-1-ketone, 2,4-two (trichloromethyl)-6-(3-bromo-4-methoxyl) phenyl-s-triazine or 2, the combination of 4-two (trichloromethyl)-6-(to methoxyl) styryl-s-triazine; The combination of EAB-F and 2-benzyl-2-dimethylamino-1-(4-morpholino phenyl)-butane-1-ketone; Triazine, EAB-F, 2-mercaptobenzimidazole, to the combination of methoxyl-styrene triazine; 2-mercaptobenzimidazole with to the combination of methoxyl-styrene triazine etc.
Use the insulativity organic pigment as black pigment.In the present embodiment, it is that so-called perylene is black that black pigment uses the perylene compounds that is black.Perylene is black to be the much smaller organic compound of electric conductivity than electric conductivity inorganicss such as carbon blacks.
In order to improve the degree of the black black that is presented of perylene, can add colored organic color such as organic red pigment or blue pigment as auxiliary pigment.Obtain following various effect by suitably selecting to add the colored organic pigment that presents the black complementary color of perylene.For example, for presenting the black pigment that has red black, can present as the organic pigment of the blueness of the complementary color of redness by interpolation and eliminate redness, thereby present preferred black as a whole as auxiliary pigment.
And, as pigment, assist the organic red pigment and/or blue organic pigment of pigment except the conduct of in black pigment, being added, also can further contain the organic pigment of colors such as presenting yellow, purple.In addition, as the auxiliary pigment that in black pigment, is added, can not contain organic red pigment and/or blue organic pigment, and contain the organic pigment of colors such as presenting yellow, purple.In addition, auxiliary pigment is not limited to redness, blueness, colour, yellow, purple, according to the matching requirements of the composition of black pigment photosensitive resin composition, can use the organic pigment that presents needed color this moment.
In addition, when using photosensitive polymer combination of the present invention to form black pattern, as described later, coat photosensitive polymer combination of the present invention on the substrate and carry out drying and form the photosensitive polymer combination layer.In order to improve coating at this moment and the rerum natura behind the photocuring, except that mentioned component, also can further contain polymer binder as bonding agent.Bonding agent can suitably be selected according to purposes such as improving compatibility, coating formation property, development, stickability.
As above-mentioned polymer binder, particularly, can enumerate, the multipolymer that makes following monomer copolymerization and obtain, described monomer is selected from acrylic acid, methacrylic acid, methyl acrylate, methyl methacrylate, ethyl acrylate, Jia Jibingxisuanyizhi, propyl acrylate, propyl methacrylate, isopropyl acrylate, isopropyl methacrylate, n-butyl acrylate, n-BMA, tert-butyl acrylate, the metering system tert-butyl acrylate, acrylic acid 2-hydroxy methacrylate, 2-hydroxyethyl methacrylate, acrylic acid 2-hydroxy propyl ester, methacrylic acid 2-hydroxy propyl ester, benzyl acrylate, benzyl methacrylate, the phenoxy group acrylate, the phenoxymethyl acrylate, isobornyl acrylate, isobornyl methacrylate, glycidyl methacrylate, styrene, acrylamide, Methacrylamide, vinyl cyanide, methacrylonitrile etc.; And have the acid cellulose modifier of carboxyl and the multipolymer of polyoxyethylene, polyvinylpyrrolidone, vinyl cyanide, ethlyene dichloride or vinylidene chloride on the side chain; The multipolymer of vinylidene chloride, chloridized polyolefin or ethlyene dichloride and vinyl acetate; Polyvinyl acetate, vinyl cyanide and cinnamic multipolymer; The multipolymer of vinyl cyanide and styrene, butadiene; Polyethylene alkyl ether; Polyethylene alkyl ketone; Polystyrene; Polyamide; Polyurethane; Polyethylene terephthalate isophthalic acid ester (Port リ エ チ レ Application テ レ Off レ one ト イ ソ Off レ one ト); Acetylcellulose and polyvinylbutyral etc.Especially, in order to improve the development of alkaline aqueous solution, the monomer that uses acrylic acid, methacrylic acid etc. to have carboxyl is advisable as copolymer composition.Aforesaid propylene acid, methacrylic acid etc. preferably are 5 weight %～40 weight % in copolymer composition.In addition, preferably make the hydroxyl reaction of multi-anhydride and carboxymethyl cellulose, carboxyethyl cellulose, carboxy-propyl cellulose, Carboxymethyl Cellulose, hydroxyethyl cellulose, hydroxypropyl cellulose and the celluosic resin that obtains.
With respect to the summation of the optical polymerism compound of 100 weight portions, ethylene type compound, Photoepolymerizationinitiater initiater, black pigment, the content of polymer binder is smaller or equal to 400 weight portions, preferably smaller or equal to 200 weight portions.
In order further to improve the coating of photosensitive polymer combination of the present invention, except above-mentioned substance, can also cooperate solvent.As solvent, can preferably use the glycol monomethyl methyl ether, ethylene glycol monomethyl ether, the glycol monomethyl propyl ether, ethylene glycol monobutyl ether, ethylene glycol dimethyl ether, the ethylene glycol bisthioglycolate ethylether, the ethylene glycol bisthioglycolate propyl ether, propylene glycol monomethyl ether, propylene glycol list ethylether, propylene glycol list propyl ether, the propylene glycol single-butyl ether, the propylene glycol dimethyl ether, the propylene glycol Anaesthetie Ether, diethylene glycol monomethyl ether, TC, diethylene glycol dimethyl ether, diethylene glycol diethyl ether, the ethylene glycol monomethyl ether acetate, ethylene glycol monomethyl ether acetate, glycol monomethyl propyl ether acetic acid esters, the ethylene glycol monobutyl ether acetic acid esters, propylene glycol monomethyl ether, propylene glycol list ethylether acetic acid esters, propylene glycol list propyl ether acetic acid esters, 2-methoxyl butylacetic acid ester, 3-methoxyl butylacetic acid ester, 4-methoxyl butylacetic acid ester, 2-methyl-3-methoxyl butylacetic acid ester, 3-methyl-3-methoxyl butylacetic acid ester, 3-ethyl-3-methoxyl butylacetic acid ester, 2-ethoxy butylacetic acid ester, 4-ethoxy butylacetic acid ester, 4-propoxyl group butylacetic acid ester, 2-methoxyl amyl group acetic acid esters, 3-methoxyl amyl group acetic acid esters, 4-methoxyl amyl group acetic acid esters, 2-methyl-3-methoxyl amyl group acetic acid esters, 3-methyl-3-methoxyl amyl group acetic acid esters, 3-methyl-4-methoxyl amyl group acetic acid esters, 4-methyl-4-methoxyl amyl group acetic acid esters, acetone, methyl ethyl ketone, metacetone, methyl isobutyl ketone, the ethyl isobutyl ketone, methyl carbonate, ethyl carbonate, propyl carbonate, butyl carbonate, benzene, toluene, dimethylbenzene, cyclohexanone, methyl alcohol, ethanol, propyl alcohol, butanols, hexanol, cyclohexanol, ethylene glycol, diethylene glycol, glycerine etc.Wherein, preferably use 3-methoxyl butylacetic acid ester.
With respect to the summation of the optical polymerism compound shown in the above-mentioned general formula (1) of 100 weight portions, ethylene type compound, Photoepolymerizationinitiater initiater, black pigment, the content of above-mentioned solvent is smaller or equal to 1000 weight portions, preferably smaller or equal to 500 weight portions.
In photosensitive polymer combination of the present invention, can further add sensitizer, thermal polymerization inhibitor, plastifier, surfactant, defoamer and other adjuvant as required.
As sensitizer, particularly, can enumerate eosin B (C.I.No.45400), eosin J (C.I.No.45380), spirit soluble eosin (C.I.No.45386), phloxin B (cyanosine, C.I.No.45410), rose bengal, erythrosine (C.I.No.45430), 2,3, xanthene dyes such as 7-trihydroxy-9-phenyl xanthene-6-ketone and rhodamine 6G; Thionine (thionine, C.I.No.52000), azure A (C.I.No.52005) and aC thiazine dyes such as (C.I.No.52002); Coumarin compounds such as Pyronine B (C.I.No.45005) and pyronine G Y pyronine dyes such as (C.I.No.45005) or 3-acetyl group cumarin, 3-acetyl group 7-diethyl amino coumarin.
As thermal polymerization inhibitor, can use p-dihydroxy-benzene, p-dihydroxy-benzene list ethylether, p methoxy phenol, pyrogallol, catechol, 2,6 ditertiary butyl p cresol, betanaphthol etc.
As plastifier, can use dioctyl phthalate, phthalandione two (dodecane ester), triethylene glycol dicaprylate, dimethyl glycol phthalate ester, tricresyl phosphate, dioctyl adipate, dibutyl sebacate, triacetyl glycerine etc.
As surfactant, can use anionic species, cationic, the various activating agents of nonionic class etc.In addition, as defoamer, can use silicone, the various defoamers of fluorine class etc.
As the formation method of black pattern of the present invention, can utilize 1) adjustment, 2 of photosensitive polymer combination) forming photosensitive polymer combination layer, 3 on the substrate) exposure, 4) develop, 5) after cure operation and form black pattern basically.
1) modulation of photosensitive polymer combination
Add photosensitive polymer combination, also add bonding agent, solvent, sensitizer, thermal polymerization inhibitor, plastifier, surfactant, defoamer etc. as required, utilize 3 roller Rolled machines, bowl mill, sand mill, injector-type mill etc. fully to disperse, mix.
2) formation of photosensitive polymer combination layer
The photosensitive polymer combination of above-mentioned modulation is coated in advance on the substrate that the surface has been carried out cleaning.As substrate, can enumerate materials such as glass, polyethylene terephthalate, acryl resin.In addition, in order to improve the stickability of substrate and photosensitive polymer combination, silane coupling agent is made an addition in the photosensitive polymer combination or with it coat on the substrate in advance.During the photosensitive resin coating composition, use contact transcription type apparatus for coating or non-contact type apparatus for coating such as spin coater, curtain coater such as roll coater, reverse coater, metering bar coater.Especially, when the thickness of film is thicker, can repeatedly be coated with or and with several above-mentioned apparatus for coating.Behind the photosensitive resin coating composition, at room temperature place a few hours～a few days or insert in storage heater, the infrared heater tens of minutes～a few hours and remove and desolvate, the thickness that forms coated film is the photosensitive polymer combination layer of 1 μ m～10 μ m.
3) exposure
After forming the photosensitive polymer combination layer, (negative mask) exposes across negative mask.The light of the provision wavelengths of using in the exposure is the activation light that produces the light of following wavelength, and described wavelength can the activation light polymerization initiator and produce free radical; Particularly, be preferably ultraviolet ray, excimer laser beam, X line, γ line, electron ray.The irradiation light quantity is carried out some changes according to the composition of employed photosensitive polymer combination, but is preferably 30mJ/cm
2～2000mJ/cm
2
4) develop
Carried out after the exposure-processed, used developer solution to wait and develop by infusion process, spray-on process.As this developer solution, use the aqueous solution of following substances: alkali-metal oxyhydroxide such as lithium, sodium, potassium; Carbonate, supercarbonate, phosphate, pyrophosphate; Primary amine such as benzyl amine, butylamine; Secondary amine such as dimethyl amine, dibenzyl amine, diethanolamine; Tertiary amines such as Trimethylamine, triethylamine, triethanolamine; Cyclic amine such as morpholine, piperazine, pyridine; Polyamine such as ethylene diamine, hexamethylene diamine; Ammonium hydroxide classes such as tetraethyl ammonium hydroxide, trimethyl benzyl ammonium hydroxide, trimethylphenyl benzylic hydrogens amine-oxides; Hydroxide sulfonium classes such as trimethyl hydroxide sulfonium, diethylmethyl hydroxide sulfonium, dimethyl benzyl hydroxide sulfonium; Other choline etc.
5) cure after
After cure in the operation, for the black pattern that give to develop forms provides intensity and chemical resistance, thermotolerance, temperature is adjusted into 150 ℃～250 ℃ is advisable.
As mentioned above, photosensitive polymer combination of the present invention and use this photosensitive polymer combination and the black pattern that forms is especially preferably as the black matrix of the colored filter of LCD etc.As mentioned above, on substrate, use photosensitive polymer combination of the present invention to form as the black pattern of deceiving matrix pattern, be coloured to R, G, B etc. as if waiting by decoration method, print process, pigment dispersing method, then because the light-proofness of black matrix portion is higher, thereby can make the colored filter that shows the contrast height, do not have the LCD etc. of the colour developing excellence that look leaks.
Embodiment
Hereinafter embodiments of the invention are described, but scope of the present invention is not limited to these
Embodiment.
[embodiment 1]
The manufacturing of optical polymerism compd A
In the four-hole boiling flask of 500ml, the limit is blown into the nitrogen limit and stirs, make the methacrylic acid of PGMEA (propylene glycol monomethyl ether), the 75g of 400g, the benzyl methacrylate of 210g, the 2-hydroxyethyl methacrylate of 15g, the azoisobutyronitrile of 5g under 65 degree～70 degree, react 3 hours, thereby obtain the optical polymerism compd A.
2. the modulation of black-colored photosensitive resin composition
With following weight ratio optical polymerism compound (optical polymerism compd A, DPHA (dipentaerythritol acrylate)), Photoepolymerizationinitiater initiater (trade name: CGI369, チ バ ス ペ シ ヤ Le テ イ ケ ミ カ Le ズ Co., Ltd. system), pigment (perylene is black, red pigment, blue pigment) are mixed.Wherein red pigment is used dispersible pigment dispersion " CF red EX-109 " (C.I.P red-177 contains 20% anthraquinone class red), and blue pigment uses blue pigment dispersion liquid CF blue UM (containing 20% C.I.P blue-15:6).
Wherein, optical polymerism compd A: DPHA: CGI369: perylene is black: red pigment: blue pigment=10: 2: 1: 5: 2: 1.
For this potpourri, add MBA (3-methoxyl butylacetic acid ester) as solvent, modulating and making this potpourri is the 20 weight % of MBA, thereby obtains the black photosensitive resin combination.
3. the formation of black matrix pattern
Use spin coater (TR25000: chemical industry (strain) system is answered in Tokyo) that the above-mentioned black photosensitive resin combination for preparing is coated on the glass substrate with clean surface of thickness as 1mm, the thickness that makes dry caudacoria is 2 μ m, and drying formed black photosensitive resin combination layer in 2 minutes under 90 degree.
Then, across negative mask to this black photosensitive resin combination layer-selective ground irradiation ultraviolet radiation.Then, with the aqueous sodium carbonate of 0.5 weight % spray development after 60 seconds under 25 degree, in baking box in 200 ℃ carry out 30 minutes after cure, thereby form black matrix pattern.
[embodiment 2]
1. the manufacturing of optical polymerism compd A
The optical polymerism compd A is made in operation similarly to Example 1.
2. the modulation of black photosensitive resin combination
With following weight ratio optical polymerism compound (optical polymerism compd A, DPHA), Photoepolymerizationinitiater initiater (CGI369), pigment (perylene is black, red pigment, blue pigment) are mixed.And, use red pigment, the blue pigment identical with embodiment 1.
Wherein, optical polymerism compd A: DPHA: CGI369: perylene is black: red pigment: blue pigment=10: 2: 1: 1: 0.4: 0.2.
For this potpourri, add MBA (3-methoxyl butylacetic acid ester) as solvent, modulating and making this potpourri is the 20 weight % of MBA, thereby obtains the black photosensitive resin combination.
3. the formation of black matrix pattern
Operation forms black matrix pattern similarly to Example 1.
[embodiment 3]
1. the manufacturing of optical polymerism compd A
The optical polymerism compd A is made in operation similarly to Example 1.
2. the modulation of black photosensitive resin combination
With following weight ratio optical polymerism compound (optical polymerism compd A, DPHA), Photoepolymerizationinitiater initiater (CGI369), pigment (perylene is black, red pigment, blue pigment) are mixed.And, use red pigment, the blue pigment identical with embodiment 1.
Wherein, optical polymerism compd A: DPHA: CGI369: perylene is black: red pigment: blue pigment=10: 2: 1: 25: 10: 5.
For this potpourri, add MBA (3-methoxyl butylacetic acid ester) as solvent, modulating and making this potpourri is the 20 weight % of MBA, thereby obtains the black photosensitive resin combination.
3. the formation of black matrix pattern
Operation forms black matrix pattern similarly to Example 1.
[comparative example 1]
1. the manufacturing of optical polymerism compd A
The optical polymerism compd A is made in operation similarly to Example 1.
2. the modulation of black photosensitive resin combination
With following weight ratio optical polymerism compound (optical polymerism compd A, DPHA), Photoepolymerizationinitiater initiater (CGI369), black pigment (carbon black) are mixed.And, use carbon dispersion liquid CF blackEX-1455 (containing 24% high resistance carbon: drive state's pigment system) as black pigment.
Wherein, optical polymerism compd A: DPHA: CGI369: black pigment=10: 2: 1: 8.
For this potpourri, add MBA (3-methoxyl butylacetic acid ester) as solvent, modulating and making this potpourri is the 20 weight % of MBA, thereby obtains the black photosensitive resin combination.
3. the formation of black matrix pattern
Operation forms black matrix pattern similarly to Example 1.
[evaluation of embodiment 1～3 and comparative example 1]
Specific inductive capacity, the OD (optical density (OD)) of each black matrix pattern that mensuration is formed by embodiment 1～3 and comparative example 1.In addition, come visual inspection to deceive the shape of matrix pattern by optical microscope, and it is estimated.Its result is as shown in table 1.
[table 1]
| Embodiment | Specific inductive capacity | OD(μm -1) | Shape |
| Embodiment 1 | 3.7 | More than or equal to 1 | Well |
| Embodiment 2 | 3.1 | More than or equal to 0.7 | Well |
| Embodiment 3 | 5.5 | More than or equal to 1 | Bad |
| Comparative example 1 | 19 | More than or equal to 1 | Well |
Can confirm little many, that is, effective of the specific inductive capacity of the black matrix pattern that the permittivity ratio of the black matrix pattern that is formed by embodiment 1～3 is formed by comparative example 1 than comparative example 1 insulativity by table 1.And in order to be used as the photonasty sept, specific inductive capacity is usually smaller or equal to 7, and the specific inductive capacity of the black matrix pattern that is formed by embodiment 1～3 can be used as the photonasty sept all smaller or equal to 7.
In addition, can confirm that the OD of the black matrix pattern that is formed by embodiment 1,3 is more than or equal to 1 μ m by table 1
-1, be high light-proofness.
In addition, can confirm that the pattern form of the black matrix pattern that is formed by embodiment 1,2 is also good by table 1.
Claims (12)
1. black-colored photosensitive resin composition, it is the black-colored photosensitive resin composition that contains the pigment composition of black pigment, it is characterized in that, described pigment composition contains the insulativity organic pigment.
2. black-colored photosensitive resin composition as claimed in claim 1 is characterized in that, described black pigment is that perylene is black.
3. black-colored photosensitive resin composition as claimed in claim 1 or 2 is characterized in that, described pigment composition contains organic red pigment and blue organic pigment.
4. as any described black-colored photosensitive resin composition of claim 1～3, it is characterized in that the specific inductive capacity of the film that is formed by described black-colored photosensitive resin composition is smaller or equal to 7.
5. as any described black-colored photosensitive resin composition of claim 1～4, it is characterized in that, with respect to the thickness of the film of per 1 μ m, is more than or equal to 1 by the optical density (OD) value of the formed film of described black-colored photosensitive resin composition.
6. as any described black-colored photosensitive resin composition of claim 1～5, it is characterized in that described black-colored photosensitive resin composition contains optical polymerism compound, Photoepolymerizationinitiater initiater and solvent.
7. as any described black-colored photosensitive resin composition of claim 1～6, it is characterized in that, with respect to the total weight of described optical polymerism compound, described Photoepolymerizationinitiater initiater and described solvent, the content ratio of described pigment composition is 20 weight %～250 weight %.
8. black matrix is characterized in that it is formed by any described black-colored photosensitive resin composition of claim 1～7.
9. organic EL display panel is characterized in that, it has the described black matrix of claim 8.
10. display panels is characterized in that, it has the described black matrix of claim 8.
11. the photonasty sept is characterized in that, it is formed by any described black-colored photosensitive resin composition of claim 1～7.
12. display panels is characterized in that, it has the described photonasty sept of claim 11.
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|---|---|---|---|
| JP2005-256761 | 2005-09-05 | ||
| JP2005256761A JP2007071994A (en) | 2005-09-05 | 2005-09-05 | Black photosensitive resin composition |
| JP2005256761 | 2005-09-05 |
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| CN1928714B CN1928714B (en) | 2010-06-09 |
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| JP (1) | JP2007071994A (en) |
| KR (1) | KR100814660B1 (en) |
| CN (1) | CN1928714B (en) |
| TW (1) | TWI390344B (en) |
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Also Published As
| Publication number | Publication date |
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| TW200712767A (en) | 2007-04-01 |
| KR100814660B1 (en) | 2008-03-18 |
| CN1928714B (en) | 2010-06-09 |
| JP2007071994A (en) | 2007-03-22 |
| KR20070026004A (en) | 2007-03-08 |
| TWI390344B (en) | 2013-03-21 |
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