CN102792412A - Photocurable composition - Google Patents

Photocurable composition Download PDF

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CN102792412A
CN102792412A CN2011800132946A CN201180013294A CN102792412A CN 102792412 A CN102792412 A CN 102792412A CN 2011800132946 A CN2011800132946 A CN 2011800132946A CN 201180013294 A CN201180013294 A CN 201180013294A CN 102792412 A CN102792412 A CN 102792412A
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牛山幸佑
伊藤秀之
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Taiyo Holdings Co Ltd
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Taiyo Holdings Co Ltd
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    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F2/00—Processes of polymerisation
    • C08F2/46—Polymerisation initiated by wave energy or particle radiation
    • C08F2/48—Polymerisation initiated by wave energy or particle radiation by ultraviolet or visible light
    • C08F2/50—Polymerisation initiated by wave energy or particle radiation by ultraviolet or visible light with sensitising agents
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/16—Nitrogen-containing compounds
    • C08K5/32—Compounds containing nitrogen bound to oxygen
    • C08K5/33—Oximes
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/0005—Production of optical devices or components in so far as characterised by the lithographic processes or materials used therefor
    • G03F7/0007—Filters, e.g. additive colour filters; Components for display devices
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/004—Photosensitive materials
    • G03F7/0047—Photosensitive materials characterised by additives for obtaining a metallic or ceramic pattern, e.g. by firing
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/004—Photosensitive materials
    • G03F7/027—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds
    • G03F7/028—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds with photosensitivity-increasing substances, e.g. photoinitiators
    • G03F7/031—Organic compounds not covered by group G03F7/029
    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01J—ELECTRIC DISCHARGE TUBES OR DISCHARGE LAMPS
    • H01J11/00—Gas-filled discharge tubes with alternating current induction of the discharge, e.g. alternating current plasma display panels [AC-PDP]; Gas-filled discharge tubes without any main electrode inside the vessel; Gas-filled discharge tubes with at least one main electrode outside the vessel
    • H01J11/10—AC-PDPs with at least one main electrode being out of contact with the plasma
    • H01J11/12—AC-PDPs with at least one main electrode being out of contact with the plasma with main electrodes provided on both sides of the discharge space
    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01J—ELECTRIC DISCHARGE TUBES OR DISCHARGE LAMPS
    • H01J11/00—Gas-filled discharge tubes with alternating current induction of the discharge, e.g. alternating current plasma display panels [AC-PDP]; Gas-filled discharge tubes without any main electrode inside the vessel; Gas-filled discharge tubes with at least one main electrode outside the vessel
    • H01J11/20—Constructional details
    • H01J11/22—Electrodes, e.g. special shape, material or configuration
    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01J—ELECTRIC DISCHARGE TUBES OR DISCHARGE LAMPS
    • H01J11/00—Gas-filled discharge tubes with alternating current induction of the discharge, e.g. alternating current plasma display panels [AC-PDP]; Gas-filled discharge tubes without any main electrode inside the vessel; Gas-filled discharge tubes with at least one main electrode outside the vessel
    • H01J11/20—Constructional details
    • H01J11/22—Electrodes, e.g. special shape, material or configuration
    • H01J11/24—Sustain electrodes or scan electrodes
    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01J—ELECTRIC DISCHARGE TUBES OR DISCHARGE LAMPS
    • H01J9/00—Apparatus or processes specially adapted for the manufacture, installation, removal, maintenance of electric discharge tubes, discharge lamps, or parts thereof; Recovery of material from discharge tubes or lamps
    • H01J9/02—Manufacture of electrodes or electrode systems
    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01J—ELECTRIC DISCHARGE TUBES OR DISCHARGE LAMPS
    • H01J2211/00—Plasma display panels with alternate current induction of the discharge, e.g. AC-PDPs
    • H01J2211/20—Constructional details
    • H01J2211/22—Electrodes
    • H01J2211/225—Material of electrodes
    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01J—ELECTRIC DISCHARGE TUBES OR DISCHARGE LAMPS
    • H01J2211/00—Plasma display panels with alternate current induction of the discharge, e.g. AC-PDPs
    • H01J2211/20—Constructional details
    • H01J2211/34—Vessels, containers or parts thereof, e.g. substrates
    • H01J2211/44—Optical arrangements or shielding arrangements, e.g. filters or lenses
    • H01J2211/444—Means for improving contrast or colour purity, e.g. black matrix or light shielding means

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  • Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Physics & Mathematics (AREA)
  • Plasma & Fusion (AREA)
  • Organic Chemistry (AREA)
  • Medicinal Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Health & Medical Sciences (AREA)
  • Polymers & Plastics (AREA)
  • General Physics & Mathematics (AREA)
  • Manufacturing & Machinery (AREA)
  • Materials Engineering (AREA)
  • Ceramic Engineering (AREA)
  • Spectroscopy & Molecular Physics (AREA)
  • Materials For Photolithography (AREA)
  • Polymerisation Methods In General (AREA)
  • Gas-Filled Discharge Tubes (AREA)

Abstract

Disclosed are: a photocurable composition which enables the formation of a highly fine pattern and which enables the formation of a pattern without causing any line defects by undercutting in a bus electrode (4a, 4b) having a white/black two-layered structure; and a bus electrode having a white/black two-layered structure which is produced using the photocurable composition. The photocurable composition is characterized by comprising an inorganic powder, an organic binder, a photopolymerizable monomer, and a photopolymerization initiator which comprises an oxime ester compound having a nitrocarbazole structure and is represented by general formula (I).

Description

Photocurable composition
Technical field
The present invention relates on the front substrate of plasma display panel (being designated hereinafter simply as " PDP "), form the Photocurable composition of alkali developable useful in the fine electrode circuit and use it to form the PDP of the black layer (lower floor) in the double-deck bus electrode of electrode, particularly black and white.
Background technology
PDP utilizes the flat-panel screens of carrying out the demonstration of video, information based on the luminous of plasma discharge.The principle that shows based on the color of PDP is following: make the plasma discharge generation in the opposed two interelectrode battery spaces (discharge space) that on the front glass substrate that is separated by rib (dividing wall) and back side glass substrate, form; Through the ultraviolet ray excited fluorophor that is formed at back side glass substrate inner face that the discharge by gases such as the He that in each battery space, encloses, Xe produces, the visible light of 3 primary colors is produced.Each battery space is through being demarcated by the rib that is parallel to real estate arrangement setting among the AC type PDP that becomes main flow now.Below, Yi Bian describe on one side with reference to accompanying drawing.
Fig. 1 illustrates the structure example of face discharge mode PDP of 3 electrode structures of panchromatic demonstration partly.The lower surface of glass substrate 1 in front; A pair of show electrode 2a, 2b are provided with multiple row with the spacing arrangement of regulation, said show electrode 2a, 2b by transparency electrode 3a that is used to discharge or 3b and the bus electrode 4a or the 4b that are used to reduce the line resistance of this transparency electrode form.Last at these show electrodes 2a, 2b, be formed for the transparency dielectric layer 5 (low-melting glass) of stored charge, vapor deposition matcoveredn (MgO) 6 above that through printing, sintering.
On the other hand, on the glass substrate 11, be provided with the rib (dividing wall) 12 and the addressing electrode (data electrode) 13 that is configured in each discharge space of the striated in multiple row dividing discharge space with the spacing arrangement of regulation overleaf.In addition, dispose the fluorescent membrane of red (14a), blue (14b), green (14c) 3 looks regularly at the inner face of each discharge space.In panchromatic demonstration, constitute a pixel with fluorescent membrane 14a, 14b, the 14c of these 3 red, blue, green primary colors.
In the PDP of said structure, between a pair of show electrode 2a and 2b, apply ac pulse voltage, it is discharged between the electrode on the same substrate, therefore be called as " face discharge mode ".In addition, be formed with following structure (reflection-type): fluorescent membrane 14a, 14b, the 14c of the ultraviolet ray excited back substrate 11 that produces through discharge see through the transparency electrode 3a, 3b of front glass substrate 1 and see the visible light of generation.
About the formation of bus electrode 4a, 4b, up to now through vapor deposition, three layers of sputter Cr-Cu-Cr and film forming, utilize photoetching process to carry out patterning then to carry out.But,, therefore carry out following method recently: with the method for sintering after the conductive paste silk screen printings such as silver-colored paste because operation quantity is many, cost is high; Perhaps at coating photoelectric sensitivity conductive property paste and after, develop, then the method for sintering through the pattern mask exposure in order to form the live width below the 150 μ m.
In recent years; In order to improve the contrast of picture; When forming bus electrode; Sometimes at the black layer of the black conductive property paste that becomes the lower floor's printing conductive property difference that shows side, the white layer of the good silver-colored paste of printing conductive property above that forms the double-deck electrode of black and white (for example with reference to patent documentation 1 etc.).
Yet, in the double-deck mode of this black and white, because the weary light transmission of white break; Black layer as lower floor can't carry out sufficient photocuring, after the development, can produce the live width with respect to white layer; The live width of black layer very little (undercut, undercutting) the such problem that becomes.
The prior art document
Patent documentation
Patent documentation 1: japanese kokai publication hei 4-272634 communique
Summary of the invention
The problem that invention will solve
The present invention makes in view of the above problems; Its purpose is to provide a kind of Photocurable composition; Said Photocurable composition can form high fine pattern, and in addition in the double-deck bus electrode of black and white, it is damaged and form pattern not produce the lines that caused by undercutting.
The scheme that is used to deal with problems
In order to reach aforementioned purpose; According to an embodiment of the invention; A kind of Photocurable composition is provided; It is characterized in that the Photoepolymerizationinitiater initiater that it contains inorganic powder, organic binder bond, photopolymerization monomer and comprises oxime ester compound, said oxime ester compound have the nitro carbazole structure shown in the formula (I).Thus, can form the black and white double-decker bus electrode that has reduced undercutting.
Figure BDA00002120985900031
(in the formula, R 1The alkyl of expression carbon number 1 ~ 20, the aryl of carbon number 6 ~ 30, the aralkyl or the CN of carbon number 7 ~ 30, the hydrogen atom of alkyl, aryl and aralkyl can be further by OR 11, COR 11, SR 11, NR 12R 13,-NCOR 12-OCOR 13, CN, halogen atom ,-CR 11=CR 12R 13Or-CO-CR 11=CR 12R 13Replace R 11, R 12And R 13Represent the alkyl of hydrogen atom, carbon number 1 ~ 20, the aryl of carbon number 6 ~ 30, the aralkyl of carbon number 7 ~ 30 or the heterocyclic radical of carbon number 2 ~ 20 independently of one another;
R 2Expression R 21Or OR 21, R 21Alkyl, the aryl of carbon number 6 ~ 30 or the aralkyl of carbon number 7 ~ 30 of expression carbon number 1 ~ 20, the hydrogen atom of alkyl, aryl and aralkyl can further be replaced R by halogen atom 3Alkyl, the aryl of carbon number 6 ~ 30 or the aralkyl of carbon number 7 ~ 30 of expression carbon number 1 ~ 20;
R 1, R 3, R 11, R 12And R 13The methylene of represented substituent alkylene moiety can be interrupted 1 ~ 5 time by unsaturated bond, ehter bond, thioether bond, ester bond, thioester bond, amido link or amino-formate bond; Above-mentioned substituent moieties can have side chain; It also can be cyclic alkyl; Above-mentioned substituent alkyl end can be a unsaturated bond, R 3Can form ring with the phenyl ring of adjacency;
R 4And R 5Represent R independently of one another 21, OR 21, CN or halogen atom, a and b are 0 ~ 3 independently of one another.）
The effect of invention
According to Photocurable composition of the present invention, can form high fine pattern, in addition in the double-deck bus electrode of black and white, can realize further that undercutting reduces.
Description of drawings
Fig. 1 is the exploded stereogram of the AC type PDP of face discharge mode.
Fig. 2 is the partial cutaway schematic of an example of the formation operation of double-deck bus electrode of expression black and white.
Embodiment
Discoveries such as inventor of the present invention; In the formation of the double-deck bus electrode of black and white; Photoepolymerizationinitiater initiater through use contains inorganic powder, organic binder bond, photopolymerization monomer and comprises oxime ester compound can form the pattern that has suppressed undercutting, thereby has accomplished the present invention; Wherein, said oxime ester compound has the nitro carbazole structure shown in the formula (I).
Below the Photocurable composition of this execution mode is elaborated.
At first, the Photocurable composition that in the black skin membrane (lower floor) of the double-deck bus electrode of black and white, uses (below be called " black layer is used composition ") is elaborated.
The inorganic powder that in the Photocurable composition of this execution mode, uses is according to the purposes of electrode pattern and difference when using with composition as black layer, is used black pigment.
As the black pigment that uses in composition at the black layer of this execution mode and since after state and carry out 300 ~ 600 ℃ of such high temperature sinterings in the sintering circuit, therefore preferred use at high temperature has the stable inorganic pigment of tone.Particularly, for example can enumerate out by separate metal oxides such as Cu, Fe, Cr, Mn, Co, Ni, Ru, La, Sr and/or the black pigment processed by the composite oxides that two or more metallic elements form.The viewpoint that black epithelium densification that particularly forms behind the sintering and tone are excellent, can use copper-chromium aptly is that black composite oxide, copper-iron are black composite oxide, cobaltosic oxide (Co 3O 4) etc.They can two or more alone or in combination uses.
As the average grain diameter (D50) of this black pigment, the particle diameter below the preferred 2 μ m.Average grain diameter is 2 μ m when following, does not damage adaptation etc. even a small amount of interpolation also can form fine and close sintering epithelium, can satisfy sufficient interlayer conductivity (interlayer conduction that transparency electrode and bus electrode are white layer) and blackness simultaneously.On the other hand, if average grain diameter is bigger than 2 μ m, the compactness variation of sintering epithelium then, the blackness of the black electrode pattern of formation reduces easily.In addition, if littler than 0.01 μ m, covering power reduces and also presents transparent feel sometimes, therefore more preferably 0.01 ~ 1 μ m.
In addition, as the compounding amount of this black pigment, be the scope of 10 ~ 100 mass parts in preferred per 100 mass parts organic binder bonds.Than above-mentioned scope after a little while, can't obtain sufficient blackness behind the sintering.On the other hand, than above-mentioned scope for a long time, light transmission reduces, change be easy to generate undercutting.50 ~ 100 mass parts more preferably.
In addition, as inorganic powder, in order to improve behind the sintering adaptation to substrate, compounding glass dust as required.As this glass dust; Preferred glass transition temperature (Tg) is that 300 ~ 500 ℃, glass softening point (Ts) are 400 ~ 600 ℃ low-melting glass powder, can suit to use with lead oxide, bismuth oxide, zinc oxide, lithia or with the glass dust of alkali borosilicate as principal component.
As being the preferred example of the glass dust of principal component with lead oxide, can enumerate out quality % in the oxide benchmark, have PbO and be 48 ~ 82%, a B 2O 3Be 0.5 ~ 22%, SiO 2Be 3 ~ 32%, Al 2O 3Be 0 ~ 12%, BaO is 0 ~ 15%, TiO 2Be 0 ~ 2.5%, Bi 2O 3Be 0 ~ 25% composition, the amorphous glass powder (frit) that softening point is 420 ~ 580 ℃.
In addition,, can enumerate out quality %, have Bi in the oxide benchmark as being the preferred example of the glass dust of principal component with the bismuth oxide 2O 3Be 6 ~ 88%, B 2O 3Be 5 ~ 30%, SiO 2Be 5 ~ 25%, Al 2O 3Be 0 ~ 5%, BaO is 0 ~ 20%, ZnO is 1 ~ 20% composition, the amorphous glass powder that softening point is 420 ~ 580 ℃.
In addition,, can enumerate out quality %, have ZnO and be 25 ~ 60%, a K in the oxide benchmark as being the preferred example of the glass dust of principal component with zinc oxide 2O is 2 ~ 15%, B 2O 3Be 25 ~ 45%, SiO 2Be 1 ~ 7%, Al 2O 3Be 0 ~ 10%, BaO is 0 ~ 20%, MgO is 0 ~ 10% composition, the amorphous glass powder that softening point is 420 ~ 580 ℃.
About the compounding amount of this glass dust, can carry out compounding with the ratio that in per 100 mass parts organic binder bonds is below 200 parts, be preferably below 100 parts.
As the organic binder bond of the black layer that is used for this execution mode with composition, contain carboxy resin, particularly, himself have containing the carboxyl photoresist and not having containing carboxy resin and all can using of ethylenical unsaturated double bonds of ethylenical unsaturated double bonds.As the resin that can suit to use (oligomer and polymer all can), can enumerate out the following carboxy resin that contains.
(1) through making the carboxy resin that contains that unsaturated carboxylic acid and the compound copolymerization with unsaturated double-bond obtain.
(2) through containing the carboxyl photoresist as side group to what unsaturated carboxylic acid and the copolymer with unsaturated double-bond compound carried out that addition obtains with the olefinic unsaturated group.
(3) make unsaturated carboxylic acid and, compound with epoxy radicals and unsaturated double-bond and have the copolymer reaction of the compound of unsaturated double-bond, and the secondary hydroxyl of generation is reacted with multi-anhydride and obtain contain the carboxyl photoresist.
(4) make compound with hydroxyl and unsaturated double-bond with, have the acid anhydrides of unsaturated double-bond and have copolymer reaction and obtain contain the carboxyl photoresist of the compound of unsaturated double-bond.
(5) make the reaction of epoxy compounds and unsaturated monocarboxylic, and the secondary hydroxyl that makes generation react with multi-anhydride and obtain contain the carboxyl photoresist.
(6) make the organic acid that has 1 carboxyl in 1 molecule and do not have ethylenic unsaturated bond with, have the compound of unsaturated double-bond and the epoxy reaction of the copolymer of (methyl) glycidyl acrylate, and the secondary hydroxyl of generation is reacted with multi-anhydride and obtain contain carboxy resin.
(7) make the reaction of hydroxyl polymer-containing and multi-anhydride and obtain contain carboxy resin.
(8) make the reaction of hydroxyl polymer-containing and multi-anhydride and obtain contain carboxy resin further react with compound with epoxy radicals and unsaturated double-bond and obtain contain the carboxyl photoresist.
Need to prove that in this manual, (methyl) acrylic acid ester is the term that acrylic acid ester, methacrylate and their mixture are referred to as, other similar expression also is identical.
This carboxy resin that contains can be separately or mix and use, under any circumstance, and all preferably with their the ratio compounding of 10 ~ 80 quality % that add up to total composition.The compounding amount is compared with above-mentioned scope when very few, and it is inhomogeneous that the distribution of the above-mentioned resin in the epithelium of formation becomes easily, is difficult to obtain the sufficient photo-curable and the photocuring degree of depth, based on selectivity exposure, the patterning that the develops difficulty that becomes.On the other hand, compare with above-mentioned scope when too much, the skew, the live width that are easy to generate pattern during sintering are shunk.
As this weight average molecular weight that contains carboxy resin, be preferably 1000 ~ 100000 respectively.Molecular weight is lower than at 1000 o'clock, and the adaptation of epithelium that can be when developing causes harmful effect.On the other hand, be higher than at 100000 o'clock, be easy to generate poor visualization.5000 ~ 70000 scope more preferably.
In addition, as the acid number that contains carboxy resin, be preferably the scope of 50 ~ 250mgKOH/g respectively.When acid number is lower than 50mgKOH/g, thereby to the insufficient poor visualization that is easy to generate of the dissolubility of aqueous alkali.On the other hand, when higher, be easy to generate the deterioration of the adaptation of epithelium, the dissolving of photocuring portion (exposure portion) during development than 250mgKOH/g.
In addition, under the situation that contains the carboxyl photoresist, preferably its pair key equivalent is 350 ~ 2000.Under the little situation of two key equivalent proportion 350, easy residual residue during sintering.On the other hand, under 2000 big situation, the operation allowance during development is narrow, needs high exposure in addition during photocuring.More preferably 400 ~ 1500.
The photopolymerization monomer that uses in composition at the black layer of this execution mode uses with raising development property for the photo-curable that promotes composition.As this photopolymerization monomer; Can enumerate out for example acrylic acid 2-hydroxy methacrylate, acrylic acid 2-hydroxy propyl ester, diethylene glycol diacrylate, triethylene glycol diacrylate, polyethyleneglycol diacrylate, urethane diacrylate, trimethylolpropane triacrylate, pentaerythritol triacrylate, tetramethylol methane tetraacrylate, trimethylolpropane oxirane modification triacrylate, trimethylolpropane epoxy pronane modification triacrylate, dipentaerythritol five acrylic acid ester, dipentaerythritol acrylate and each methyl acrylic ester corresponding with the aforesaid propylene acid esters; The monoesters of polyacids such as phthalic acid, adipic acid, maleic acid, itaconic acid, butanedioic acid, trihemellitic acid, terephthalic acid (TPA) and (methyl) acrylic acid hydroxyalkyl acrylate, diester, three esters or its above polyester etc.; But do not receive the restriction of specific material, these can two or more alone or in combination uses in addition.In these photopolymerization monomers, has the polyfunctional monomer of plural (methyl) acryloyl group in preferred 1 molecule.
About the compounding amount of this photopolymerization monomer, be that 20 ~ 100 mass parts are suitable in per 100 mass parts organic binder bonds.The compounding amount is difficult to obtain the sufficient photo-curable of composition than 20 mass parts after a little while, and on the other hand, when surpassing the volume of 100 mass parts, the photocuring of epithelium surface element is compared with its deep and accelerated, therefore be easy to generate solidify inhomogeneous.
As the Photoepolymerizationinitiater initiater of the black layer that is used for this execution mode, importantly use oxime ester compound with the nitro carbazole structure shown in the formula (I) with composition.Therefore oxime ester compound shown in the formula (I) has ISO, even below white layer that light transmission lacks, also can carry out sufficient photocuring, can suppress the generation of undercutting.
(in the formula, R 1The alkyl of expression carbon number 1 ~ 20, the aryl of carbon number 6 ~ 30, the aralkyl or the CN of carbon number 7 ~ 30, the hydrogen atom of alkyl, aryl and aralkyl can be further by OR 11, COR 11, SR 11, NR 12R 13,-NCOR 12-OCOR 13, CN, halogen atom ,-CR 11=CR 12R 13Or-CO-CR 11=CR 12R 13Replace R 11, R 12And R 13Represent the alkyl of hydrogen atom, carbon number 1 ~ 20, the aryl of carbon number 6 ~ 30, the aralkyl of carbon number 7 ~ 30 or the heterocyclic radical of carbon number 2 ~ 20 independently of one another;
R 2Expression R 21Or OR 21, R 21Alkyl, the aryl of carbon number 6 ~ 30 or the aralkyl of carbon number 7 ~ 30 of expression carbon number 1 ~ 20, the hydrogen atom of alkyl, aryl and aralkyl can further be replaced R by halogen atom 3Alkyl, the aryl of carbon number 6 ~ 30 or the aralkyl of carbon number 7 ~ 30 of expression carbon number 1 ~ 20;
R 1, R 3, R 11, R 12And R 13The methylene of represented substituent alkylene moiety can be interrupted 1 ~ 5 time by unsaturated bond, ehter bond, thioether bond, ester bond, thioester bond, amido link or amino-formate bond; Above-mentioned substituent moieties can have side chain; It also can be cyclic alkyl; Above-mentioned substituent alkyl end can be a unsaturated bond, R 3Can form ring with the phenyl ring of adjacency.
R 4And R 5Represent R independently of one another 21, OR 21, CN or halogen atom, a and b are 0 ~ 3 independently of one another.）
About the compounding amount of this Photoepolymerizationinitiater initiater,, be preferably 0.5 ~ 20 mass parts with respect to 100 mass parts organic binder bonds.When being lower than 0.5 mass parts, be difficult to obtain the sufficient photo-curable of composition.On the other hand, when surpassing 20 mass parts, the photocuring of epithelium surface element is compared with its deep and is accelerated, and it is inhomogeneous therefore to be easy to generate curing.1 ~ 10 mass parts more preferably.
In addition, also can be as required with above-mentioned other Photoepolymerizationinitiater initiaters of Photoepolymerizationinitiater initiater compounding, sensitizer etc.
As this Photoepolymerizationinitiater initiater, can enumerate out for example benzoin and benzoin alkylether classes such as benzoin, benzoin methylether, benzoin ethyl ether, benzoin iso-propylether; Acetophenone, 2,2-dimethoxy-2-phenyl acetophenone, 2,2-diethoxy-2-phenyl acetophenone, 1, acetophenones such as 1-dichloroacetophenone; 2-methyl isophthalic acid-[4-(methyl mercapto) phenyl]-2-morpholino propane-1-ketone, 2-benzyl-2-dimethylamino-1-(4-morpholino phenyl)-1-butanone, 2-(dimethylamino)-2-［ (4-aminomethyl phenyl) methyl ］-1-［ 4-(4-morpholinyl) phenyl ］-aminoacetophenone classes such as 1-butanone; Anthraquinone classes such as 2-methylanthraquinone, 2-EAQ, 2-tert-butyl group anthraquinone, 1-chloroanthraquinone; 2,4-dimethyl thioxanthones, 2,4-diethyl thioxanthone, 2-clopenthixal ketone, 2, thioxanthene ketones such as 4-diisopropyl thioxanthones; Ketal classes such as acetophenone dimethyl ketal, benzil dimethyl ketal; Benzophenones such as benzophenone; Or xanthene ketone; (2,6-dimethoxy benzoyl) (2,4, the 4-amyl group) phosphine oxide, two (2,4, the 6-trimethylbenzoyl)-phenyl phosphine oxide, 2,4,6-trimethylbenzoyl diphenyl phosphine oxide, 2,4, phosphinoxides such as 6-trimethylbenzoyl phenyl-phosphonic acid ethyl ester; 1-［ 9-ethyl-6-(2-toluyl)-9H-carbazole-9-yl ］-1-oxime ester classes such as (O-acetyl oximes); Various peroxides etc., these Photoepolymerizationinitiater initiaters can two or more alone or in combination uses.
In addition; As sensitizer; Can enumerate out for example N; N-dimethyl ethyl aminobenzoate, N, the such photosensitizers of tertiary amines such as N-dimethylaminobenzoic acid isopentyl ester, amyl group-4-dimethylaminobenzoic acid ester, triethylamine, triethanolamine, these sensitizers can use a kind perhaps to make up two or more uses.
For through with the black layer of this execution mode with the composition dilution pasteization, make it can be easily to coatings such as base materials, but the solvent of the suitable amount of compounding.
As this solvent, can enumerate out for example ketone such as MEK, cyclohexanone; Toluene, xylenes, durene etc. are aromatic hydrocarbon based; Glycol ethers such as cellosolve, methyl cellosolve, carbitol, methyl carbitol, BC, propylene glycol monomethyl ether, dipropylene glycol monomethyl ether, DPG diethyl ether, Triethylene glycol ethyl ether; Ethyl acetate, butyl acetate, cellosolve acetate, butyl cellosolve acetate, carbitol acetate, BC acetate, propylene glycol monomethyl ether acetate, 2,2,4-trimethyl-1, ester classes such as 3-pentanediol list isobutyl ester; Alcohols such as ethanol, propyl alcohol, ethylene glycol, propane diols, terpineol; Aliphatic hydrocarbon such as octane, decane; Oil series solvents such as benzinum, naphtha, hydrogenated naphtha, solvent naphtha etc.They can two or more alone or in combination uses.
In addition, in order to improve the storage stability of Photocurable resin composition, preferred add the metal that belongs to the inorganic powder composition or have with oxide powder complexing materialization or the compound that forms effect such as salt as stabilizer.
As this stabilizer; Can enumerate out various organic acids such as malonic acid, adipic acid, formic acid, acetic acid, acetoacetate, citric acid, stearic acid, maleic acid, fumaric acid, phthalic acid; Acid such as various phosphate cpds (inorganic phosphate, organic phosphoric acid), boric acid such as phosphoric acid, phosphorous acid, hypophosphorous acid, methyl orthophosphoric acid, etherophosphoric acid, butylphosphoric acid ester, phenyl phosphate, phosphorous acid ethyl ester, phosphorous acid diphenyl ester, list (2-methacryloxyethyl) phosphate ester acid can two or more alone or in combination uses.This stabilizer is preferably in per 100 mass parts inorganic powders to be the ratio interpolation of 0.1 ~ 10 mass parts.
And then so known additives such as silane coupler such as antifoaming agent such as thickeners such as hot polymerization inhibitor such as compounding quinhydrones, hydroquinone monomethyl ether, tert-butyl catechol, 1,2,3,-thrihydroxy-benzene, phenthazine, fine particle silica, organobentonite, imvite, silicon-type, fluorine system, macromolecular and/or levelling agent, imidazoles system, thiazole system, triazole system as required.
Need to prove that more than the black layer of explanation promptly is used in the material of black matrix pattern with composition, also can use no problemly.
Then, the Photocurable composition of the white skin membrane (upper strata) that is used for the double-deck bus electrode of black and white (below, be called " white layer is used composition ") is elaborated.
The white layer of this execution mode replaces the above-mentioned black layer of black pigment with composition as the inorganic powder with composition except using electroconductive powder, is same composition, compounding ratio basically.Therefore, use composition about the white layer of this execution mode, below only explanation and above-mentioned black layer of difference with composition.
Electroconductive powder as using in composition at the white layer of this execution mode can use for example simple substance and alloys thereof such as Ag, Au, Ni, Cu, Al, Sn, Pt, Ru, and SnO 2, In 2O 3, ITO (Indium Tin oxide, indium tin oxide), RuO 2Deng.They can two or more alone or in combination uses.
As the shape of this electroconductive powder, can use different shapes such as spherical, sheet (flake) shape, dendritic crystalline, if consider light characteristic, dispersiveness, then preferred use spherical.In addition, as average grain diameter (D50), from the average grain diameter below the preferred 10 μ m of the viewpoint of lines shape.The more preferably average grain diameter below the 5 μ m.In addition, as specific area, be preferably 0.01 ~ 2.0m 2/ g.The not enough 0.01m of specific area 2During/g, cause sedimentation during preservation easily, on the other hand, surpass 2.0m 2During/g, the oil suction quantitative change is big and the flowability of composition suffers damage.0.1 ~ 1.0m more preferably 2/ g.
In addition, for the oxidation that prevents electroconductive powder, improve dispersiveness in the composition, make development property stabilisation, especially preferably Ag, Ni, Al are handled with aliphatic acid.As this aliphatic acid, can enumerate out for example oleic acid, linoleic acid, leukotrienes, stearic acid etc.
About the compounding amount of this electroconductive powder, be made as 50 ~ 2000 mass parts in preferred per 100 mass parts organic binder bonds.The compounding amount of conductive powder is difficult to obtain good electrical conductivity than 50 mass parts after a little while, when surpassing 2000 mass parts, the tendency of paste change difficulty is arranged.
Photopolymerization monomer as using in composition at the white layer of this execution mode can use to be used for the photopolymerization monomer of black layer with composition, and particularly the viewpoint of the live width behind the inhibition sintering is preferably used two functional monomers.
The white layer of this execution mode with composition in, compounding is used for the black layer of Photoepolymerizationinitiater initiater with composition as required.Even is also can be cured and form electrode pattern because be unworthy of the mixed light polymerization initiator with Photoepolymerizationinitiater initiater as any composition.Think this be because, after state bus electrode and form in the operation, during the dry or exposure of coating, the Photoepolymerizationinitiater initiater during lower floor's (black layer) films can carry out cross-linking reaction through coating film diffusion upwards in last coating film; When perhaps making public, the cross-linking reaction in the following coating film proceeds to coating film, is cured thus.
On the other hand, when the white layer of single-layer electrodes pattern application is used composition, need the compounding Photoepolymerizationinitiater initiater.At this moment, the oxime ester compound that has the nitro carbazole structure shown in the above-mentioned general formula (I) through compounding can obtain good resolution as Photoepolymerizationinitiater initiater.
Then, the electrode pattern formation method to the Photocurable composition that uses this execution mode is elaborated.
About Photocurable composition of the present invention, film forming is under the situation of film like in advance, is laminated on the substrate to get final product; Under the situation for paste-like; Coating process through it is suitable that silk screen print method, rod are coated with machine, scraper plate coating machine etc. is coated on the substrate, for example on the glass substrate of the front substrate that becomes PDP; Then in order to obtain dry to touch property; At for example about 60 ~ 120 ℃ times dry about 5 ~ 40 minutes, make solvent evaporation with heated air circulation type drying oven, far infrared drying stove etc., what cannot not obtain stickingly films.After this, make public, development, sintering, form the telegraph circuit of the pattern of regulation.
As exposure process, can be to use the contact exposure and the noncontact exposure of negative mask with regulation exposing patterns.As the light source that is used to make public, use Halogen lamp LED, high-pressure mercury lamp, laser, metal halide lamp, black light lamp, electrodeless lamp etc.Exposure is preferably 50 ~ 1000mJ/cm 2About.
As developing procedure, can use spray-on process, infusion process etc.As developer solution, can enumerate out NaOH, the aqueous solution of amine such as the metal base aqueous solution, MEA, diethanol amine, triethanolamine such as potassium hydroxide, sodium carbonate, potash, sodium metasilicate.Particularly can suit to use the dilute alkaline aqueous solution of the concentration below about 1.5 quality %, as long as with the carboxyl saponification that contains carboxy resin in the composition, uncured (unexposed portion) of removal, to the not restriction of above-mentioned developer solution.In addition, in order after development, to remove unwanted developer solution, preferably wash, the acid neutralization.
As sintering circuit, the substrate after developing is carried out about 400 ~ 600 ℃ heat treated in atmosphere or blanket of nitrogen, form the conductive pattern of hoping.Wherein, the programming rate of this moment is preferably set to below 20 ℃/minute.
With Fig. 2 the situation that forms the double-deck bus electrode of black and white is elaborated.
At first; Shown in Fig. 2 (A); Utilize known in the past means such as sputtering method, ion plating, chemical vapor deposition, electro-deposition through ITO (Indium tin oxide in advance; Indium tin oxide) etc. use composition being formed with on the front glass substrate 200 of transparency electrode 201 the above-mentioned black layer of coating, carry out dry then and form sticking black layer 202.
Then, shown in Fig. 2 (B), on the black layer 202 that forms, be coated with the high white layer of conductivity that contains electroconductive powder and use composition, carry out dry white layer of sticking (conductive layer) 203 that form then.
Then, shown in Fig. 2 (C) that it is overlapping with the photomask 204 with exposing patterns, filming of 2 layers of black and white made public.Then, develop through aqueous alkali and to remove non-exposed portion,, shown in Fig. 2 (D), on transparency electrode 201, form the bus electrode 205 that forms by black layer (lower floor) 202 and white layer (upper strata) 203 then through sintering.
In addition, using composition and white layer to use composition at black layer is in advance under the situation of film forming as the dry film of film like, in thermo-compressed on the substrate and after carrying out lamination successively, can through make public, each operation of development and print (sintering) makes.In addition; Also can adopt following method: the black layer of coating is with composition and carry out each operation of drying, exposure, development, print and form lower floor's (black) afterwards on substrate, and the white layer of coating is with composition and carry out each operation of drying, exposure, development and print and form the method for upper strata (white).
Embodiment
Below embodiment is shown and comparative example specifies the present invention, certainly, the present invention does not receive the restriction of following embodiment.Wherein, following " part " and " % " short of special instruction are quality criteria.
［ synthesizing of organic binder bond (alkali soluble resin A) ］
In the flask that possesses thermometer, mixer, dropping funel and reflux condenser; Mol ratio with 0.87:0.13 drops into methyl methacrylate and methacrylic acid; Adding is as the diethylene glycol monomethyl ether acetate of solvent, as the azodiisobutyronitrile of catalyst; In blanket of nitrogen, 80 ℃ stirred 7 hours down, obtain alkali soluble resin A solution.About this alkali soluble resin A solution, the weight average molecular weight of alkali soluble resin A is about 10000, and acid number is 95mgKOH/g, and its solid constituent is 57%.
Wherein, the weight average molecular weight of the alkali soluble resin A (copolymer resins) of gained is measured with chromatographic column Shodex (registered trade mark) KF-804, KF-803, three high performance liquid chromatography that are connected of KF-802 of electrician's manufactured with clear through the pump LC-6AD that Shimadzu Seisakusho Ltd. makes.
According to the various compositions shown in the table 1, ratio (mass parts) compounding, mixing after being pre-mixed with mixer through triple-roller mill, obtain as white layer with the composition 1,2 of composition, as black layer of a composition 3,4 with composition.
[table 1]
Figure BDA00002120985900161
* 1:1,9-nonanediol diacrylate (manufacturing of chemical company of common prosperity society)
* 2: trimethylolpropane EO modification triacrylate (manufacturing of East Asia Synesis Company)
* 3: oxime ester initator (ADEKA.Corporation manufacturing)
* 4:1-[9-ethyl-6-(2-methyl benzoyl)-9H-carbazole-3-yl]-ethyl ketone 1-(O-acetyl oxime) (Xiba Special Chemical Product Co.,Ltd make oxime ester initator)
* 5: average grain diameter (D50) 2.2 μ m, maximum particle diameter (D max) 6.3 μ m, specific area 0.3m 2/ g
* 6: cobaltosic oxide, average grain diameter (D50) 0.3 μ m
* 7:Bi 2O 350%, B 2O3 16%, ZnO 14%, SiO 22%, BaO 18% thermalexpansioncoefficient 300=86 * 10 -7/ ℃, 501 ℃ of glass softening points
* 8:MODAFLOW (Monsanto Japan Limited. make levelling antifoaming agent)
* 9:P-1M (chemical company of common prosperity society make phosphate be stabilizer)
* 10: the diethylene glycol monomethyl ether acetate
< estimating the making of substrate >
Coating is dry: (the double-deck epithelium of black and white)
Composition shown in the table 13,4 is used whole the printing on glass substrate of 300 purpose polyester nets respectively, descended dry 20 minutes at 100 ℃, on substrate, form filming of black thus with IR formula drying oven.
Then; Use composition 1 on the black coating film that uses composition 3, on the black coating film of use composition 4, using composition 2; Use whole the coating on aforementioned black coating film of 200 purpose polyester nets respectively; With IR formula drying oven 100 ℃ dry 20 minutes down, form double-deck epithelium of the good black and white of dry to touch property, with it as estimating substrate.
Coating is dry: (individual layer epithelium)
Composition shown in the table 11,2 is used whole the printing on glass substrate of 200 purpose polyester nets respectively, with IR formula drying oven 100 ℃ dry 20 minutes down, form the epithelium of the good white of dry to touch property, with it as estimating substrate.
As the double-deck bus electrode of black and white, the evaluation substrate that the evaluation substrate that composition 1,3 is combined combines as embodiment 1, with composition 2,4 is as comparative example 1.In addition, as the single-layer electrodes pattern, with the evaluation substrate that uses composition 1 as embodiment 2, will use composition 2 the evaluation substrate as comparative example 2, carry out following evaluation.
< evaluation >
(resolution)
Using metal halide lamp as light source, is 200mJ/cm with the accumulation light quantity on the composition 2Mode above-mentioned evaluation substrate is made public after, use 0.4% aqueous sodium carbonate of 30 ℃ of liquid temperature, make developing time be 10,15,30 and and 40 seconds, develop, through the washing back with the air knife drying.After this observe remaining lines, with the lines of the remaining minimum widith in N/D ground as resolution.
[table 2]
Figure BDA00002120985900181
Embodiment 1 is the situation that the Photocurable composition of this execution mode is applied to the double-deck bus electrode of black and white, can know with the comparative example 1 that uses Photocurable composition in the past and compare that resolution (live width) is improved.
Embodiment 2 is the situation that the Photocurable composition of this execution mode are applied to (individual layer) electrode, can know to have obtained good resolution.On the other hand, use in the comparative example 2 of Photocurable composition in the past, can't form lines, can know that photo-curable is insufficient.
Description of reference numerals
1,200: the front glass substrate
2a, 2b: show electrode
3a, 3b, 201: transparency electrode
4a, 4b, 205: bus electrode
5: transparency dielectric layer
6: protective layer
11: back side glass substrate
12: rib (dividing wall)
13: addressing electrode
14a, 14b, 14c: fluorescent membrane
202: black layer (lower floor)
203: white layer (upper strata, conductive layer)
204: photomask

Claims (6)

1. a black and white double-decker bus electrode is used Photocurable composition; It is characterized in that; The Photoepolymerizationinitiater initiater that it contains inorganic powder, organic binder bond, photopolymerization monomer and comprises oxime ester compound, said oxime ester compound have the nitro carbazole structure shown in the formula (I)
Figure FDA00002120985800011
In the formula, R 1The alkyl of expression carbon number 1 ~ 20, the aryl of carbon number 6 ~ 30, the aralkyl or the CN of carbon number 7 ~ 30, the hydrogen atom of alkyl, aryl and aralkyl can be further by OR 11, COR 11, SR 11, NR 12R 13,-NCOR 12-OCOR 13, CN, halogen atom ,-CR 11=CR 12R 13Or-CO-CR 11=CR 12R 13Replace R 11, R 12And R 13Represent the alkyl of hydrogen atom, carbon number 1 ~ 20, the aryl of carbon number 6 ~ 30, the aralkyl of carbon number 7 ~ 30 or the heterocyclic radical of carbon number 2 ~ 20 independently of one another;
R 2Expression R 21Or OR 21, R 21Alkyl, the aryl of carbon number 6 ~ 30 or the aralkyl of carbon number 7 ~ 30 of expression carbon number 1 ~ 20, the hydrogen atom of alkyl, aryl and aralkyl can further be replaced R by halogen atom 3Alkyl, the aryl of carbon number 6 ~ 30 or the aralkyl of carbon number 7 ~ 30 of expression carbon number 1 ~ 20;
R 1, R 3, R 11, R 12And R 13The methylene of represented substituent alkylene moiety can be interrupted 1 ~ 5 time by unsaturated bond, ehter bond, thioether bond, ester bond, thioester bond, amido link or amino-formate bond; Said substituent moieties can have side chain; It also can be cyclic alkyl; Said substituent alkyl end can be a unsaturated bond, R 3Can form ring with the phenyl ring of adjacency;
R 4And R 5Represent R independently of one another 21, OR 21, CN or halogen atom, a and b are 0 ~ 3 independently of one another.
2. black and white double-decker bus electrode according to claim 1 is used Photocurable composition, it is characterized in that, said inorganic powder comprises at least a arbitrarily in black pigment, electroconductive powder and the glass dust.
3. a plasma display panel is characterized in that, it uses claim 1 or the described black and white double-decker of claim 2 bus electrode to obtain with Photocurable composition.
4. a single-layer electrodes pattern is used Photocurable composition; It is characterized in that; The Photoepolymerizationinitiater initiater that it contains inorganic powder, organic binder bond, photopolymerization monomer and comprises oxime ester compound, said oxime ester compound have the nitro carbazole structure shown in the formula (I)
Figure FDA00002120985800021
In the formula, R 1The alkyl of expression carbon number 1 ~ 20, the aryl of carbon number 6 ~ 30, the aralkyl or the CN of carbon number 7 ~ 30, the hydrogen atom of alkyl, aryl and aralkyl can be further by OR 11, COR 11, SR 11, NR 12R 13,-NCOR 12-OCOR 13, CN, halogen atom ,-CR 11=CR 12R 13Or-CO-CR 11=CR 12R 13Replace R 11, R 12And R 13Represent the alkyl of hydrogen atom, carbon number 1 ~ 20, the aryl of carbon number 6 ~ 30, the aralkyl of carbon number 7 ~ 30 or the heterocyclic radical of carbon number 2 ~ 20 independently of one another;
R 2Expression R 21Or OR 21, R 21Alkyl, the aryl of carbon number 6 ~ 30 or the aralkyl of carbon number 7 ~ 30 of expression carbon number 1 ~ 20, the hydrogen atom of alkyl, aryl and aralkyl can further be replaced R by halogen atom 3Alkyl, the aryl of carbon number 6 ~ 30 or the aralkyl of carbon number 7 ~ 30 of expression carbon number 1 ~ 20;
R 1, R 3, R 11, R 12And R 13The methylene of represented substituent alkylene moiety can be interrupted 1 ~ 5 time by unsaturated bond, ehter bond, thioether bond, ester bond, thioester bond, amido link or amino-formate bond; Said substituent moieties can have side chain; It also can be cyclic alkyl; Said substituent alkyl end can be a unsaturated bond, R 3Can form ring with the phenyl ring of adjacency;
R 4And R 5Represent R independently of one another 21, OR 21, CN or halogen atom, a and b are 0 ~ 3 independently of one another.
5. single-layer electrodes pattern according to claim 4 is used Photocurable composition, it is characterized in that, said inorganic powder comprises at least a arbitrarily in black pigment, electroconductive powder and the glass dust.
6. a plasma display panel is characterized in that, it uses claim 4 or the described single-layer electrodes pattern of claim 5 to obtain with Photocurable composition.
CN2011800132946A 2010-03-31 2011-03-30 Photocurable composition Pending CN102792412A (en)

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