CN103279011A - Thiol-ene ultraviolet light curing nano imprinting material - Google Patents
Thiol-ene ultraviolet light curing nano imprinting material Download PDFInfo
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- CN103279011A CN103279011A CN2013102346137A CN201310234613A CN103279011A CN 103279011 A CN103279011 A CN 103279011A CN 2013102346137 A CN2013102346137 A CN 2013102346137A CN 201310234613 A CN201310234613 A CN 201310234613A CN 103279011 A CN103279011 A CN 103279011A
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Abstract
A thiol-ene ultraviolet light curing nano imprinting material comprises a liquid prepolymer with low viscosity and polyfunctionality, a photoinitiator, an auxiliary and a diluent, wherein the liquid prepolymer with low viscosity and polyfunctionality comprises a sulfydryl monomer containing silicon and an olefin monomer containing silicon; both the sulfydryl monomer containing silicon and the olefin monomer containing silicon comprise two or more curable crosslinking functional groups; the curable crosslinking functional groups are sulfydryl or carbon-based unsaturated double bonds; the liquid prepolymer accounts for 5%-90% of the total mass of the material; the mass of the diluent accounts for 95%-10% of the total mass of the material; the mass of the photoinitiator accounts for 1%-5% of the mass of the liquid prepolymer; and the mass of the auxiliary accounts for 0.01%-10% of the mass of the liquid prepolymer. The thiol-ene ultraviolet light curing nano imprinting material has the characteristics as follows: the viscosity is low, the material can be cured rapidly and can be completely cured in the air, and the shrinkage rate is low; and on the basis of a rotary film coating process, the material can be used as ultraviolet light curing nano imprinting rubber, large-area ultraviolet light curing nano imprinting is realized, and a pattern in a critical size of less than 100 nanometers is produced economically and efficiently.
Description
Technical field
The present invention relates to a kind of ultraviolet photocureable material, specifically a kind of ultraviolet light curing nano impression materials based on sulfydryl-alkene photo-crosslinking.
Background technology
Nanometer embossing has obtained to pay close attention to widely as a kind of pattern technology of preparing that is not subjected to photolithography limitation restriction, low cost, high resolving power, high yield.In fields such as information storage, biology sensor and subwavelength optical elements, become that price is relatively low, dependable performance, had the technology of preparing of volume production ability.
The nano impression material is one of key element of nanometer embossing, especially in becoming the ultraviolet light curing nano stamping technique of stamping technique main flow gradually, the ultraviolet light polymerization membraneous material of low viscosity, high resolving power, high etching selection has become the key that influences imprinted pattern fidelity, high aspect ratio structure preparation.The impression materials that is applied at present in the ultraviolet light curing nano stamping technique mainly is the esters of acrylic acid photocrosslinkable polymer.Esters of acrylic acid ultraviolet light prepolymer cures speed is fast, but can not solidify under aerobic environment, and after solidifying bigger volumetric shrinkage is arranged.
US Patent No. 6334960 discloses a kind of ultraviolet light curing nano stamping technique-stepping flash imprint technology; it adopts viscosity low; the uV curable acrylic compounds prepolymer system of good fluidity is as nano impression glue; when template with after the uV curable macromolecule prepolymer contacts; do not need ambient pressure; utilize the distinctive capillarity of liquid; ultraviolet photocureable material is injected in the nanostructured of template at an easy rate; and make its quick curing by ultraviolet light; thereby make the moulding process can be in room temperature; finish rapidly under the very low pressure, thereby accomplish scale production.
Chinese patent CN200610088466.7 discloses a kind of ultraviolet light polymerization compound substance that nano impression also can be used for photoetching technique that can be used for, reactive group is vinyl ether, epoxy and esters of acrylic acid reactive group, improve this layer material to the selectivity of oxygen plasma etching by in material, adding material, realize double layer UV curing nano impression.
CN200810204674.8 discloses a kind of ultraviolet nanometer impression and has impressed glue with siliceous (methyl) acrylic ester type photocuring, formed by (methyl) acrylic ester type monomer, siliceous (methyl) acrylate, light trigger, crosslinking chemical and auxiliary agent, by impressing glue at transfer layer spin coating one deck, through after the reactive ion etching, imprinted pattern can be transferred to substrate.
Because existing esters of acrylic acid ultraviolet light nano impression material can not be in air set, thereby when impression film edge can exist and not solidify into branch, be unfavorable for that also nanometer embossing combines with other technology (as soft stamping technique), therefore, need provide a kind of can quick and complete curing in air, the ultraviolet light curing nano impression materials of high resolving power, high oxygen etching selection, thereby improve the compatibility of nanometer embossing and other micro-nano processing technology, economical and efficient ground output critical size is less than the pattern of 100 nanometers.
Summary of the invention
The technical problem to be solved in the present invention is: the deficiency that overcomes existing esters of acrylic acid ultraviolet light nano impression material, providing can quick and complete curing in air, the ultraviolet light curing nano impression materials of high resolving power, high oxygen etching selection ratio, by being combined with ultraviolet light curing nano impression bi-layer imprint system, realize and the compatibility of multiple micro-nano processing technology that economical and efficient ground output critical size is less than the pattern of 100 nanometers.
Technical solution of the present invention is: a kind of sulfydryl-alkene ultraviolet light curing nano impression materials, to be formed by liquid prepolymer, thinning agent, light trigger and the auxiliary agent of low viscosity, polyfunctionality, and volumetric shrinkage is less than 5% behind the ultraviolet light polymerization.The liquid prepolymer of low viscosity, polyfunctionality is made up of (siliceous) sulfydryl monomer and (siliceous) olefinic monomer.(siliceous) sulfydryl monomer mass accounts for liquid prepolymer quality 10%-90%, and (siliceous) olefinic monomer composition accounts for liquid prepolymer quality 90%-10%.Described (siliceous) sulfydryl monomer and (siliceous) olefinic monomer all contain two or more curable crosslinking functionalities, and curable crosslinking functionality is sulfydryl or carbon carbon unsaturated double-bond.Sulfydryl includes but not limited to mercapto alkane, sulfydryl aromatic hydrocarbon, mercaptoacetate and mercaptopropionic acid ester.Carbon carbon unsaturated double-bond includes but not limited to vinyl, vinyl ether, propenyl ether, allyl ether, acrylate, methacrylate, styrene, N-vinylamide, conjugated diolefine, vinyl cyanide, allyl isocyanuric acid ester, allyl triazine, beta-unsaturated esters, maleimide.Liquid prepolymer accounts for the 5%-90% of prepolymer and thinning agent gross mass.The reactive solvent of described thinning agent right and wrong or reactive monomer.Non-reactive solvent includes but not limited to pentane, hexane, heptane, octane, chlorine benzene,toluene,xylene, acetone, MEK, methylisobutylketone, formic ether, ethyl acetate, dimethyl formamide and their potpourri; Reactive monomer includes but not limited to methyl acrylate, ethyl acrylate, butyl acrylate, methyl methacrylate, Jia Jibingxisuanyizhi, butyl methacrylate, methyl vinyl ether, ethyl vinyl ether and their potpourri.The thinning agent quality accounts for the 95%-10% of material gross mass.Described light trigger is selected from one or more of benzoin ethyl ether, benzoin dimethylether, benzoin isobutyl ether, dibenzoyl, benzophenone.The light trigger quality is the 0.1%-5% of liquid prepolymer quality.Described auxiliary agent is selected from one or more of organ of luorosilane levelling agent, fluorochemical surfactant, organic alcohol, polyoxyalkylene alkyl co-modified silicone oil defoamer.The auxiliary agent quality is the 0.01%-10% of liquid prepolymer quality.
Described liquid prepolymer is made up of (siliceous) sulfydryl monomer and (siliceous) olefinic monomer, and kinetic viscosity at room temperature is 1 centipoise-10000 centipoise.Siliceous sulfydryl monomer is long-chain siloxane, hydrosulphonyl silane or the sulfydryl grafting cage shape siloxane that sulfydryl terminal or side chain contain sulfydryl, the sulfydryl monomer is tri-thiol propionic ester alkane, four mercaptopropionic acid ester alkane or mercaptopropionic acid ester triazine, siliceous olefinic monomer is long-chain siloxane, vinyl silanes or the carbon carbon unsaturated double-bond grafting cage shape siloxane that carbon carbon unsaturated double-bond terminal or side chain contain carbon carbon unsaturated double-bond, and olefinic monomer is triallyl ether alkane, triallyl ether alkylol, allyl isocyanuric acid ester or allyl triazine.Described silicon-containing monomer quality accounts for the 10%-90% of liquid prepolymer quality.
The application of a kind of sulfydryl-alkene ultraviolet light curing nano impression materials, be applied to the ultraviolet light curing nano imprint process, form layer of even fluid film, thickness 20 nanometers-500 nanometer by spin-coating technology at smooth surfaces such as quartz, silicon, high molecular polymers; Form the micro-nano structure pattern by nano-imprint process at fluid film, and then be converted into metal or semiconductor structure.
Above-mentioned ultraviolet light curing nano imprint process is characterized in: tie up to based on double-deck colloid and prepare micro-nano structure on the substrate, upper strata uV curable nano impression glue is sulfydryl-alkene ultraviolet light curing nano impression materials, thickness 20 nanometer to 200 nanometers; Lower floor is thermoplastics type's high molecular polymer transfer layer, thickness 200 nanometer to 1000 nanometers; Described high molecular polymer transfer layer material is a kind of of polymethylmethacrylate, polystyrene or polycarbonate.
In the bilayer colloid system, the ratio of the upper strata uV curable nano impression glue after the curing and the reactive ion etching speed of lower floor's high molecular polymer transfer layer in oxygen is greater than 1:5, the nano-pattern of low depth-to-width ratio can be delivered to lower floor's high molecular polymer transfer layer by plasma etching on the uV curable nano impression glue of upper strata, and the structure depth-to-width ratio significantly increases.
Lower floor's high molecular polymer transfer layer can dissolve in organic solvent.High aspect ratio structure is after the high molecular polymer transfer layer forms, and plated metal or semiconductor material are with an organic solvent removed the high molecular polymer transfer layer, can be metal or semiconductor structure with the transfer layer thaumatropy.Described organic solvent includes but not limited to acetone, methyl alcohol, ethanol and chlorobenzene.
The present invention's advantage compared with prior art is: provide a kind of can quick and complete curing in air, the ultraviolet light curing nano impression materials of high resolving power, high oxygen etching selection; do not need vacuum or nitrogen protection; can realize the nano impression process; also can in soft imprint process, use; impress double-deck colloid system based on spin-coating and ultraviolet light curing nano; form the high-aspect-ratio polymer architecture; and then by thin film deposition and transfer layer dissolving, form metal or semiconductor microactuator micro-nano structure at substrate.
Description of drawings
Fig. 1 is the metal pattern of using prescription 1 preparation in the present embodiment, 2 microns of minimum feature;
Fig. 2 is the pattern electron scanning micrograph that prescription 2 impression backs obtain in the present embodiment, characteristic dimension 200 nanometers;
Fig. 3 is the pattern electron scanning micrograph that prescription 3 impression backs obtain in the present embodiment, cycles 320 nanometer;
Fig. 4 is the pattern that prescription 4 impression backs obtain in the present embodiment, and 5 microns of minimum feature, interpolation are step instrument scanning result;
Fig. 5 is the pattern that prescription 5 impression backs obtain in the present embodiment, 1.5 microns of grating cycles;
Fig. 6 is the photo of prescription 6 imprint result on quartz substrate in the present embodiment, 20 microns of live widths;
Fig. 7 is the pattern that prescription 7 impression backs obtain in the present embodiment, 2 microns of minimum feature.
Embodiment
Following embodiment only limits to explain the present invention, and protection scope of the present invention should comprise the full content of claim, and namely can realize the full content of claim of the present invention by following examples those skilled in the art.
Prescription 1
Embodiment 1:
The application of sulfydryl-alkene ultraviolet light curing nano impression materials in the prescription 1:
Polymethylmethacrylate is dissolved in the chlorobenzene, and massfraction is 8%, rotates film forming at silicon chip, obtains the transfer layer of 250 nano thickness, and 180 ℃ were toasted 2 minutes.
To fill a prescription, each component mixes in 1, is spin-coated on the polymethylmethacrylate transfer layer, and thickness is 180 nanometers.
Under 0.5 atmospheric pressure, carry out the ultraviolet light curing nano impression, remove template after the curing.
Remove for impressing remnant layer under the reactive ion etching condition of 2:1 at fluoroform and oxygen flow ratio, by oxygen reaction ion etching structure is passed to transfer layer then, and exposes substrate.
Hot evaporated metal layer was put into acetone soln ultrasonic 5 minutes with substrate, obtained the metal construction identical with impression block.
Fig. 1 is the metal pattern of using prescription 1 preparation in the present embodiment, 2 microns of minimum feature.
Embodiment 2
Prescription 2
Fig. 2 is the pattern electron scanning micrograph that prescription 2 impression backs obtain in the present embodiment, characteristic dimension 200 nanometers.
Embodiment 3
Prescription 3
| Component | Mass percent (%) |
| Vinyl replaces cage shape siloxane entirely | 3.5 |
| Trimethylolpropane tris (3-mercaptopropionic acid ester) | 6 |
| EBECRYL?9260 | 2 |
| Chlorobenzene | 88 |
| Irgacure907 | 0.3 |
| EFKA3277 | 0.2 |
Fig. 3 is the pattern electron scanning micrograph that prescription 3 impression backs obtain in the present embodiment, cycles 320 nanometer.
Embodiment 4
Prescription 4
Fig. 4 is the pattern that prescription 4 impression backs obtain in the present embodiment, and 5 microns of minimum feature, interpolation are step instrument scanning result.
Embodiment 5
Prescription 5
| Component | Mass percent (%) |
| Acryloxy propyl group methylsiloxane homopolymer | 6 |
| Pentaerythrite four-3-mercaptopropionic acid ester | 4 |
| 1,3 two butanols diacrylate | 2 |
| Epichlorokydrin | 87 |
| Irgacure819 | 0.6 |
| FC4430 | 0.4 |
Fig. 5 is the pattern that prescription 5 impression backs obtain in the present embodiment, 1.5 microns of grating cycles.
Embodiment 6
Prescription 6
Fig. 6 is the photo of prescription 6 imprint result on quartz substrate in the present embodiment, 20 microns of live widths.
Embodiment 7
Prescription 7
| Component | Mass percent (%) |
| Vinyl replaces cage shape siloxane entirely | 13 |
| Tetramethylol methane tetraacrylate | 22 |
| Trimethylolpropane tris (3-mercaptopropionic acid ester) | 16 |
| The pentanediol diacrylate | 8.6 |
| Tert-butyl acrylate | 28 |
| Irgacure369 | 2 |
| YCK1270 | 1.8 |
| Sumilyzer?GA80 | 0.6 |
Fig. 7 is the pattern that prescription 7 impression backs obtain in the present embodiment, 2 microns of minimum feature.
Need to prove that according to the above embodiment of the present invention, those skilled in the art are the four corners that can realize independent claims of the present invention and appurtenance fully, implementation procedure and method are with above-mentioned embodiment; And the non-elaborated part of the present invention belongs to techniques well known.
The above; only for part embodiment of the present invention, but protection scope of the present invention is not limited thereto, and any those skilled in the art are in the technical scope that the present invention discloses; the variation that can expect easily or replacement all should be encompassed within protection scope of the present invention.
Claims (10)
1. sulfydryl-alkene ultraviolet light curing nano impression materials, it is characterized in that: liquid prepolymer, thinning agent, light trigger and auxiliary agent by low viscosity, polyfunctionality are formed; The liquid prepolymer of described low viscosity, polyfunctionality is made up of siliceous sulfydryl monomer and not siliceous olefinic monomer, not siliceous sulfydryl monomer and siliceous olefinic monomer or siliceous sulfydryl monomer and siliceous olefinic monomer; Described siliceous sulfydryl monomer mass accounts for liquid prepolymer quality 10%-90%, and siliceous olefinic monomer composition accounts for liquid prepolymer quality 90%-10%; Described monomer all contains two or more curable crosslinking functionalities, and curable crosslinking functionality is sulfydryl or carbon carbon unsaturated double-bond; Described sulfydryl comprises mercapto alkane, sulfydryl aromatic hydrocarbon, mercaptoacetate and mercaptopropionic acid ester; Described carbon carbon unsaturated double-bond comprises vinyl, vinyl ether, propenyl ether, allyl ether, acrylate, methacrylate, styrene, N-vinylamide, conjugated diolefine, vinyl cyanide, allyl isocyanuric acid ester, allyl triazine, beta-unsaturated esters, maleimide; Described liquid prepolymer accounts for the 5%-90% of prepolymer and thinning agent gross mass; The reactive solvent of described thinning agent right and wrong or reactive monomer; Described non-reactive solvent comprises pentane, hexane, heptane, octane, chlorine benzene,toluene,xylene, acetone, MEK, methylisobutylketone, formic ether, ethyl acetate, dimethyl formamide and their potpourri; Described reactive monomer comprises methyl acrylate, ethyl acrylate, butyl acrylate, methyl methacrylate, Jia Jibingxisuanyizhi, butyl methacrylate, methyl vinyl ether, ethyl vinyl ether and their potpourri; The thinning agent quality accounts for the 95%-10% of material gross mass; Described light trigger is selected from one or more of benzoin ethyl ether, benzoin dimethylether, benzoin isobutyl ether, dibenzoyl, benzophenone; Described light trigger quality is the 0.1%-5% of liquid prepolymer quality; Described auxiliary agent is selected from one or more of organ of luorosilane levelling agent, fluorochemical surfactant, organic alcohol, polyoxyalkylene alkyl co-modified silicone oil defoamer, and the auxiliary agent quality is the 0.01%-10% of liquid prepolymer quality.
2. sulfydryl according to claim 1-alkene ultraviolet light curing nano impression materials, it is characterized in that: described siliceous sulfydryl monomer is the long-chain siloxane that sulfydryl terminal or side chain contain sulfydryl, hydrosulphonyl silane or sulfydryl grafting cage shape siloxane, not siliceous sulfydryl monomer is tri-thiol propionic ester alkane, four mercaptopropionic acid ester alkane or mercaptopropionic acid ester triazine, siliceous olefinic monomer is the long-chain siloxane that carbon carbon unsaturated double-bond terminal or side chain contain carbon carbon unsaturated double-bond, vinyl silanes or carbon carbon unsaturated double-bond grafting cage shape siloxane, not siliceous olefinic monomer is triallyl ether alkane, triallyl ether alkylol, allyl isocyanuric acid ester or allyl triazine.
3. sulfydryl according to claim 1-alkene ultraviolet light curing nano impression materials, it is characterized in that: the liquid prepolymer of described low viscosity, polyfunctionality kinetic viscosity at room temperature is 1 centipoise-10000 centipoise.
4. sulfydryl according to claim 1-alkene ultraviolet light curing nano impression materials, it is characterized in that: volumetric shrinkage is less than 5% behind the described liquid prepolymer ultraviolet light polymerization.
5. sulfydryl according to claim 1-alkene ultraviolet light curing nano impression materials, it is characterized in that: described liquid prepolymer can form layer of even fluid film, thickness 20 nanometers-500 nanometer at quartz, silicon, high molecular polymer smooth surface by spin-coating technology.
6. sulfydryl according to claim 5-alkene ultraviolet light curing nano impression materials is characterized in that: be applied to the ultraviolet light curing nano imprint process, form the micro-nano structure pattern at fluid film, and then be converted into metal or semiconductor structure.
7. according to one of any described sulfydryl-alkene ultraviolet light curing nano impression materials of claim 1-6, it is characterized in that: tie up to based on double-deck colloid and prepare micro-nano structure on the substrate, upper strata uV curable nano impression glue is described sulfydryl-alkene ultraviolet light curing nano impression materials, thickness 20 nanometer to 200 nanometers; Lower floor is thermoplastics type's high molecular polymer transfer layer, thickness 200 nanometer to 1000 nanometers; Described high molecular polymer transfer layer material is a kind of of polymethylmethacrylate, polystyrene or polycarbonate.
8. according to one of any described ultraviolet light curing nano impression materials of claim 1-6, it is characterized in that: in described double-deck colloid is, the ratio of the upper strata uV curable nano impression glue after the curing and the reactive ion etching speed of lower floor's high molecular polymer transfer layer in oxygen is greater than 1:5, the nano-pattern of low depth-to-width ratio can be delivered to lower floor's high molecular polymer transfer layer by plasma etching on the uV curable nano impression glue of upper strata, and the structure depth-to-width ratio significantly increases.
9. ultraviolet light curing nano impression materials according to claim 8, it is characterized in that: described lower floor high molecular polymer transfer layer dissolves in organic solvent; High aspect ratio structure is after the high molecular polymer transfer layer forms, and plated metal or semiconductor material are with an organic solvent removed the high molecular polymer transfer layer, is metal or semiconductor structure with the transfer layer thaumatropy.
10. ultraviolet light curing nano impression materials according to claim 9, it is characterized in that: described organic solvent comprises acetone, methyl alcohol, ethanol and chlorobenzene.
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Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105646750A (en) * | 2014-12-02 | 2016-06-08 | 中国科学院大连化学物理研究所 | Method for preparation of organic porous monolithic material based on photoinduced thiol-ene polymerization |
| CN111019519A (en) * | 2018-10-09 | 2020-04-17 | 上海产业技术研究院 | Crosslinkable composition, preparation method and application thereof |
| CN111440519A (en) * | 2020-03-31 | 2020-07-24 | 东华大学 | Preparation method of mussel-bionic-based long-term stable amphiphilic antifouling coating |
| CN113087905A (en) * | 2021-04-30 | 2021-07-09 | 郑州中原思蓝德高科股份有限公司 | Thiol-terminated polymer, preparation method thereof and polysulfide sealant |
| CN117471852A (en) * | 2023-11-02 | 2024-01-30 | 璞璘材料科技(绍兴)有限公司 | Inkjet type nano-imprinting adhesive for semiconductor manufacturing and preparation method thereof |
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Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN105646750A (en) * | 2014-12-02 | 2016-06-08 | 中国科学院大连化学物理研究所 | Method for preparation of organic porous monolithic material based on photoinduced thiol-ene polymerization |
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| CN111440519A (en) * | 2020-03-31 | 2020-07-24 | 东华大学 | Preparation method of mussel-bionic-based long-term stable amphiphilic antifouling coating |
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| CN117471852A (en) * | 2023-11-02 | 2024-01-30 | 璞璘材料科技(绍兴)有限公司 | Inkjet type nano-imprinting adhesive for semiconductor manufacturing and preparation method thereof |
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