CN100400555C - Solidifiable composition material by ultraviolet light and application - Google Patents
Solidifiable composition material by ultraviolet light and application Download PDFInfo
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- CN100400555C CN100400555C CNB2006100884667A CN200610088466A CN100400555C CN 100400555 C CN100400555 C CN 100400555C CN B2006100884667 A CNB2006100884667 A CN B2006100884667A CN 200610088466 A CN200610088466 A CN 200610088466A CN 100400555 C CN100400555 C CN 100400555C
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- oligopolymer
- ultraviolet light
- light
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- acrylate
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- 239000002131 composite material Substances 0.000 title claims abstract description 19
- 239000000758 substrate Substances 0.000 claims abstract description 28
- 239000007788 liquid Substances 0.000 claims abstract description 20
- 125000000524 functional group Chemical group 0.000 claims abstract description 15
- 239000000178 monomer Substances 0.000 claims abstract description 11
- 239000002904 solvent Substances 0.000 claims abstract description 8
- 125000003700 epoxy group Chemical group 0.000 claims abstract description 3
- 239000000463 material Substances 0.000 claims description 92
- -1 glycidyl ester Chemical class 0.000 claims description 46
- 238000000034 method Methods 0.000 claims description 37
- 239000000203 mixture Substances 0.000 claims description 28
- 238000001259 photo etching Methods 0.000 claims description 21
- 238000001020 plasma etching Methods 0.000 claims description 19
- 229920005989 resin Polymers 0.000 claims description 19
- 239000011347 resin Substances 0.000 claims description 19
- 229920002521 macromolecule Polymers 0.000 claims description 17
- 150000003254 radicals Chemical class 0.000 claims description 17
- 239000004593 Epoxy Substances 0.000 claims description 15
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 15
- 239000003795 chemical substances by application Substances 0.000 claims description 15
- 239000012528 membrane Substances 0.000 claims description 13
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 claims description 12
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 12
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical group COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 claims description 12
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 12
- QYKIQEUNHZKYBP-UHFFFAOYSA-N Vinyl ether Chemical group C=COC=C QYKIQEUNHZKYBP-UHFFFAOYSA-N 0.000 claims description 12
- 239000002253 acid Substances 0.000 claims description 12
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 12
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- 229910052760 oxygen Inorganic materials 0.000 claims description 12
- 238000006116 polymerization reaction Methods 0.000 claims description 12
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- 239000003822 epoxy resin Substances 0.000 claims description 10
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- 229920000647 polyepoxide Polymers 0.000 claims description 10
- 229920001169 thermoplastic Polymers 0.000 claims description 10
- 239000004416 thermosoftening plastic Substances 0.000 claims description 10
- 238000012546 transfer Methods 0.000 claims description 10
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 9
- 239000005864 Sulphur Substances 0.000 claims description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 9
- 229920002120 photoresistant polymer Polymers 0.000 claims description 9
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 claims description 8
- 238000005530 etching Methods 0.000 claims description 8
- FJKIXWOMBXYWOQ-UHFFFAOYSA-N ethenoxyethane Chemical compound CCOC=C FJKIXWOMBXYWOQ-UHFFFAOYSA-N 0.000 claims description 8
- 230000000379 polymerizing effect Effects 0.000 claims description 8
- 239000002683 reaction inhibitor Substances 0.000 claims description 8
- 239000012965 benzophenone Substances 0.000 claims description 7
- 150000001875 compounds Chemical class 0.000 claims description 7
- 229940006461 iodide ion Drugs 0.000 claims description 7
- 229920001567 vinyl ester resin Polymers 0.000 claims description 7
- SOGAXMICEFXMKE-UHFFFAOYSA-N Butylmethacrylate Chemical compound CCCCOC(=O)C(C)=C SOGAXMICEFXMKE-UHFFFAOYSA-N 0.000 claims description 6
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 claims description 6
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 claims description 6
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims description 6
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 6
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 claims description 6
- 239000003999 initiator Substances 0.000 claims description 6
- 239000002184 metal Substances 0.000 claims description 6
- 229940043265 methyl isobutyl ketone Drugs 0.000 claims description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims description 6
- 239000004925 Acrylic resin Substances 0.000 claims description 5
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 claims description 5
- NIXOWILDQLNWCW-UHFFFAOYSA-M acrylate group Chemical group C(C=C)(=O)[O-] NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims description 5
- WURBFLDFSFBTLW-UHFFFAOYSA-N benzil Chemical group C=1C=CC=CC=1C(=O)C(=O)C1=CC=CC=C1 WURBFLDFSFBTLW-UHFFFAOYSA-N 0.000 claims description 5
- 239000012530 fluid Substances 0.000 claims description 5
- 239000003292 glue Substances 0.000 claims description 5
- JHPBZFOKBAGZBL-UHFFFAOYSA-N (3-hydroxy-2,2,4-trimethylpentyl) 2-methylprop-2-enoate Chemical compound CC(C)C(O)C(C)(C)COC(=O)C(C)=C JHPBZFOKBAGZBL-UHFFFAOYSA-N 0.000 claims description 4
- DKEGCUDAFWNSSO-UHFFFAOYSA-N 1,8-dibromooctane Chemical compound BrCCCCCCCCBr DKEGCUDAFWNSSO-UHFFFAOYSA-N 0.000 claims description 4
- LRWZZZWJMFNZIK-UHFFFAOYSA-N 2-chloro-3-methyloxirane Chemical compound CC1OC1Cl LRWZZZWJMFNZIK-UHFFFAOYSA-N 0.000 claims description 4
- KMNCBSZOIQAUFX-UHFFFAOYSA-N 2-ethoxy-1,2-diphenylethanone Chemical compound C=1C=CC=CC=1C(OCC)C(=O)C1=CC=CC=C1 KMNCBSZOIQAUFX-UHFFFAOYSA-N 0.000 claims description 4
- 229930008564 C01BA04 - Sparteine Natural products 0.000 claims description 4
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 claims description 4
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical group CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 claims description 4
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 claims description 4
- SLINHMUFWFWBMU-UHFFFAOYSA-N Triisopropanolamine Chemical compound CC(O)CN(CC(C)O)CC(C)O SLINHMUFWFWBMU-UHFFFAOYSA-N 0.000 claims description 4
- SLRCCWJSBJZJBV-UHFFFAOYSA-N alpha-isosparteine Natural products C1N2CCCCC2C2CN3CCCCC3C1C2 SLRCCWJSBJZJBV-UHFFFAOYSA-N 0.000 claims description 4
- 150000002118 epoxides Chemical group 0.000 claims description 4
- 239000011159 matrix material Substances 0.000 claims description 4
- KCTAWXVAICEBSD-UHFFFAOYSA-N prop-2-enoyloxy prop-2-eneperoxoate Chemical compound C=CC(=O)OOOC(=O)C=C KCTAWXVAICEBSD-UHFFFAOYSA-N 0.000 claims description 4
- SLRCCWJSBJZJBV-AJNGGQMLSA-N sparteine Chemical compound C1N2CCCC[C@H]2[C@@H]2CN3CCCC[C@H]3[C@H]1C2 SLRCCWJSBJZJBV-AJNGGQMLSA-N 0.000 claims description 4
- 229960001945 sparteine Drugs 0.000 claims description 4
- 229920001187 thermosetting polymer Polymers 0.000 claims description 4
- BMVXCPBXGZKUPN-UHFFFAOYSA-N 1-hexanamine Chemical compound CCCCCCN BMVXCPBXGZKUPN-UHFFFAOYSA-N 0.000 claims description 3
- IIFFFBSAXDNJHX-UHFFFAOYSA-N 2-methyl-n,n-bis(2-methylpropyl)propan-1-amine Chemical compound CC(C)CN(CC(C)C)CC(C)C IIFFFBSAXDNJHX-UHFFFAOYSA-N 0.000 claims description 3
- 229920000178 Acrylic resin Polymers 0.000 claims description 3
- KGWDUNBJIMUFAP-KVVVOXFISA-N Ethanolamine Oleate Chemical compound NCCO.CCCCCCCC\C=C/CCCCCCCC(O)=O KGWDUNBJIMUFAP-KVVVOXFISA-N 0.000 claims description 3
- JIGUQPWFLRLWPJ-UHFFFAOYSA-N Ethyl acrylate Chemical compound CCOC(=O)C=C JIGUQPWFLRLWPJ-UHFFFAOYSA-N 0.000 claims description 3
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 claims description 3
- 125000002723 alicyclic group Chemical group 0.000 claims description 3
- 125000001931 aliphatic group Chemical group 0.000 claims description 3
- 150000001412 amines Chemical class 0.000 claims description 3
- 125000002619 bicyclic group Chemical group 0.000 claims description 3
- CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical compound CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 claims description 3
- CREMABGTGYGIQB-UHFFFAOYSA-N carbon carbon Chemical compound C.C CREMABGTGYGIQB-UHFFFAOYSA-N 0.000 claims description 3
- 239000011203 carbon fibre reinforced carbon Substances 0.000 claims description 3
- UWNADWZGEHDQAB-UHFFFAOYSA-N i-Pr2C2H4i-Pr2 Natural products CC(C)CCC(C)C UWNADWZGEHDQAB-UHFFFAOYSA-N 0.000 claims description 3
- 150000002500 ions Chemical class 0.000 claims description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- XJRBAMWJDBPFIM-UHFFFAOYSA-N methyl vinyl ether Chemical compound COC=C XJRBAMWJDBPFIM-UHFFFAOYSA-N 0.000 claims description 3
- PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 claims description 3
- GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical compound C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 claims description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 2
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 claims description 2
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- GTPROMYYPGDANE-UHFFFAOYSA-N ethenoxyethene;prop-2-enoic acid Chemical group C=COC=C.OC(=O)C=C GTPROMYYPGDANE-UHFFFAOYSA-N 0.000 claims 1
- 239000003505 polymerization initiator Substances 0.000 claims 1
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- 238000003848 UV Light-Curing Methods 0.000 abstract 4
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- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
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- 239000001257 hydrogen Substances 0.000 description 3
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- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 1
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- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
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- FKPKRUSBFSJUPU-UHFFFAOYSA-N [S].C1=CC=CC=C1C1=CC=CC=C1 Chemical compound [S].C1=CC=CC=C1C1=CC=CC=C1 FKPKRUSBFSJUPU-UHFFFAOYSA-N 0.000 description 1
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- 125000003118 aryl group Chemical group 0.000 description 1
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Abstract
This invention discloses a UV-curing composite for photolithography or nanoimprinting technology. The UV-curing composite is composed of low-ciscosity and multi-functional oligomer, photoinitiator and dispersant. The oligomer is a liquid with low viscosity of 1-10000 cP/s at room temperature, and comprises two or more crosslinkable functional groups containing C=C double bonds or epoxy groups. The weight content of the oligomer in the oligomer and the dispersant is 5-80%. The dispersant is non-reactive solvent or reactive monomer. The weight content of the dispersant in the oligomer and the dispersant is 20-95%. The weight content of the photoinitiator is 1-10% of the oligomer. The UV-curing composite can form a uniform UV-curing thin film on a substrate by spin coating.
Description
Technical field:
The present invention relates to a kind of solidifiable composition material by ultraviolet light, especially nanometer embossing and photoetching technique solidifiable composition material by ultraviolet light.
Background technology:
Photoetching technique be preparation semiconductor integrated circuit and light, electricity, magnetic, biological device and micro mechanical system gordian technique.Traditional photoetching process is that the method for photoresist material by spin-coating formed the layer of even photoresist film on substrate, through mask plate photoresist material is exposed then, develop the back at the needed structure plan of photoresist material surface formation, be delivered on the substrate through technology bar structure patterns such as plasma etchings at last.Form structure plan by photoetching process, the height of its resolving power depends on the length of exposure wavelength, and along with the raising day by day of structure plan resolving power, its preparation cost is also more and more higher.By the structure plan of 193nm exposure wavelength preparation, resolving power can reach 90nm at present, and minimum feature reaches 37nm.Because the reducing of exposure wavelength is subjected to the optical system of lithography machine and the restriction of photoresist material material, under existence conditions, traditional photoetching technique is difficult to further obtain littler nanostructure again.And photoetching technique of future generation, though can obtain less than the structure plan below the 10nm as technology such as extreme ultraviolet photoetching, beamwriter lithography, X-X-ray lithography X, ion beam lithographies, because its equipment cost and running cost are very expensive, output is extremely low, also can't be applied to large-scale industrial production at present.
U.S. Pat 5,772,905 what describe is a kind of micro-nano structure pattern technology of preparing---nanometer embossing that is different from photoetching technique fully, its principle of work is, the template that will have sculptured nanostructured pattern is by certain pressure, after being pressed in the macromolecule membrane of heating and melting, treating macromolecular material cooling curing, nanostructure typing, remove template, and then nanostructure further is transferred on the substrate by traditional microelectronics processing means such as plasma etchings.U.S. Pat 6; 334; 960 have described a kind of ultraviolet light curing nano stamping technique---stepping exposure stamping technique; it adopts viscosity low; the uV curable macromolecule 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 nanostructure of template at an easy rate; and make its fast setting, thereby make the moulding process can be in room temperature by UV-light; finish rapidly under the very low pressure, reach the requirement that can be used for the mass-producing application.
CN200410076680.1 (methyl) acrylate resin solidifying product is made by ultra-violet curing and/or thermofixation (methyl) acrylate derivative.Described (methyl) acrylate resin solidifying product comprises high-load skeleton structure by formula 1 expression, and shows high gas-barrier property and to the good adhesive property of different base material.
CN89101377.6 urethane acrylate compounds and composition, the urethane acrylate oligopolymer that can in alkali aqueous solution, develop, it is characterized in that it comprises 2 moles of aliphatic series, alicyclic, aromatic series or fragrance-aliphatic vulcabond or their mixture, 1 mole of hydroxyalkyl or hydroxyl continuity alkyl acrylate ester monomer, 1 mole of polyvalent alcohol, 1 mole has every mole of said alkylidene polyol of alkylidene polyol of 3 to 6 hydroxyls and 3 to 6 carbon atoms to use to the dihydroxy acid of not a half mole or the reaction product of acid anhydrides.
CN03109931.9 can be used as the ultraviolet-curing paint of fibre coating, especially the ultraviolet-curing paint that can be used as fibre coating, wherein added 10~30% vinylformic acid organosilane monomer thinner, 20~40% vinylformic acid silicone resin, 10~40% acrylic acid epoxy resin, 10~20% vinylformic acid polyurethane resin, 1~2% flow agent and 1~2% photosensitizers, applied used as the inside and outside coating of optical fiber.
Since photoetching technique be one full-fledged, nanometer, the micrometer structure technology of preparing being accepted extensively and use by industry member, scientific research field, for the preparation of the structure plan of large-size have other technology incomparable superiority.If can combine photoetching technique and nanometer embossing, when the structure plan of preparation large-size, adopt photoetching technique, adopt nanometer embossing during preparation small scale structures pattern, then can make full use of photoetching technique and nanometer embossing technological merit separately.
Summary of the invention:
The objective of the invention is: propose a kind of uV curable nano impression material, especially both be applicable to nanometer embossing, also can be applied to the uV curable nano impression material of photoetching process.The present invention also aims to propose application to the material of the nano impression of substrate or photoetching.
Technical solution of the present invention is: the ultraviolet photocureable material matrix material, and by the oligopolymer (multipolymer) of low viscosity, polyfunctionality, light trigger, thinner constitutes; The oligopolymer of low viscosity, polyfunctionality is at room temperature to present low viscous liquid, room temperature or with 25 ℃ be standard, the viscosity of oligopolymer is at 1 centipoise/second~10000 centipoise/second, the oligopolymer of preferred 25 ℃ of following 100~1000 centipoise/seconds; Described liquid oligomer molecule includes the resin of two or more curable crosslinked functional groups, and curable functional group is carbon carbon unsaturated double-bond or epoxide group; Carbon carbon unsaturated double-bond comprises vinyl, propenyl, butadienyl, pseudoallyl, styryl, vinyl ester or vinyl ether; Acrylate, methacrylic ester, acrylamide or Methacrylamide, epoxide group comprise oxyethane, propylene oxide or epoxy cyclohexane; Oligopolymer accounts for the 5-80% of oligopolymer and thinner total weight percent; Reactive solvent of described thinner right and wrong or reactive monomer.Non-reactive solvent is a pentane, hexane, heptane, octane, chlorobenzene, toluene, dimethylbenzene, acetone, methylethylketone, methyl iso-butyl ketone (MIBK), manthanoate, ethyl acetate or dimethyl formamide and their mixture; Or with reactive monomer or their mixture as thinner: reactive monomer comprises methyl acrylate, ethyl propenoate, butyl acrylate, methyl methacrylate, Jia Jibingxisuanyizhi, butyl methacrylate, methylvinylether, ethyl vinyl ether, oxyethane, propylene oxide or epoxy chloropropane; Thinner accounts for the 95-20% of oligopolymer and thinner total weight percent;
Preferably contain the resin of vinyl ether functional group or contain the resin of epoxy-functional, preferred triaryl sulphur of light trigger or diaryl iodide ion type optical acid generating agent based on the uV curable material of positively charged ion initiated polymerization mechanism; The material that preferably has the acrylate acrylate group based on the ultraviolet photocureable material of free radical triggering mechanism, the preferred dibenzoyl of light trigger, benzophenone, Benzoin ethyl ether or benzoin isobutyl ether, or ether compound, the consumption of light trigger is 1~10%, preferred 2~5% of an oligopolymer amount weight percent.
Use as the photoresist material material, in the uV curable composition, added the light initiating polymerizing reaction inhibitor, control the problem of initiator diffusion and polyreaction diffusion.The consumption of light initiating polymerizing reaction inhibitor is about 0.1~25%, preferred 1~5% of light trigger consumption molar percentage.
The crosslinked functional group of foregoing curable is vinyl ether or epoxide group, then light trigger is sulphur, iodine father-in-law ionic optical acid generating agent, be triaryl sulphur, diaryl iodide ion type optical acid generating agent, the photoresponse inhibitor is three replacement organic amines, as dibutyl thanomin, diisobutyl thanomin, dimethyl undecyl amine, tri-isopropanolamine, sparteine, methyl bicyclic hexyl amine or triisobutyl amine etc.The crosslinked functional group of foregoing curable is as being acrylate or methacrylic ester, and then light trigger is radical initiators such as dibenzoyl, benzophenone, and the photoresponse inhibitor is the free radical quencher.Quencher preferred aryl groups benzofuranones, bisphenolmonoacryates compound, hindered amine compound and hydroxylamine compound.
According to above-mentioned, the consumption of light trigger is 2~5% of an oligopolymer amount weight percent, and the consumption of light initiating polymerizing reaction inhibitor is about 0.1~25% of light trigger consumption molar percentage.Especially 1~5%.
UV curable material composite fluid film layer improves the selectivity of this layer material to the oxygen plasma etching, the preferred reactive organosilicon material by reactive organosilicon material of adding or non-reactive organic silicone material in the material.The organosilicon material that adds in the uV curable composition can be to have reactive functional groups, as promptly having the organosilicon material of vinyl ether, epoxy and (methyl) acrylate; Also can be or non-reacted organosilicon material.Dosage is: the organosilicon material that has vinyl ether, epoxy and (methyl) acrylate; Non-reacted organosilicon material accounts for the 5-20% of oligopolymer gross weight.
The application of ultraviolet photocureable material matrix material, be applied to nano impression glue or be applied to photoetching technique as photoresist material, it is characterized in that comprising double layer material and be used for nano impression or photoetching substrate, upper strata uV curable material composite fluid film layer material is the described material of one of claim 1 to 7, thickness 10-100nm; Lower floor is thermoplastics type or thermosetting macromolecule material membrane transfer layer, thickness 200-1000nm; Thermoplastics type or thermosetting macromolecule material membrane transfer layer by the method for selectivity plasma etching, are delivered to the structure plan for preparing in this tunic in upper layer film.Lower floor's macromolecular material transfer layer can be selected the macromolecular material of heat curing-type for use, by copying on the substrate as etch mask bar structure pattern; Select thermoplastics type's macromolecular material for use, by metal lift from method patterning is copied on the substrate.
Upper layer of material and subsurface material have selectivity to the oxygen plasma etching after the above-mentioned curing, the speed of upper layer film etching is less than the speed of lower membrane etching, therefore the structure plan that forms in the upper layer film can be used as mask, transfer on the lower membrane by the oxygen plasma etching, the aspect ratio of patterning is exaggerated simultaneously; The organosilicon material that preferably has reactive functional groups can form cross-linked network with other ultraviolet photocureable material simultaneously when ultraviolet light polymerization.Lower floor's macromolecular material among the present invention can be the macromolecule membranous layer behind the curing cross-linked, by copying on the substrate as etch mask bar structure pattern; Also can be soluble thermoplastics type's macromolecule membranous layer, by metal lift from method patterning is copied on the substrate.
The duplicature system can be with the little structure plan of aspect ratio that forms on uV curable composition liquid film, method by the selectivity plasma etching is enlarged into the big structure plan of aspect ratio on macromolecule membranous layer, structure plan can be copied on the substrate more reliably.In the common macromolecular material of forming by carbon, hydrogen, oxygen, add the ability that the material that contains element silicon can effectively improve material antioxygen gas plasma etching.Solidify back upper layer of material and subsurface material the oxygen plasma etching is had selectivity, the speed of upper layer film etching is less than the speed of lower membrane etching, therefore the structure plan that forms in the upper layer film can be used as mask, transfer on the lower membrane by the oxygen plasma etching, the aspect ratio of patterning is exaggerated simultaneously.
Further improvement of the present invention also comprises, adds softening agent, releasing agent, even paint, static inhibitor etc.In order to prevent after spin-coating, residual solvent preferentially selects for use reactive monomer or their mixture as thinner to the detrimentally affect that the uV curable composition film produces among the present invention.
Characteristics of the present invention are: a kind of photoetching technique that both can be used for is provided, has also can be used for the ultraviolet photocureable material mixture of nanometer embossing.This invention is based on the substrate method by spin-coating, forms layer of even uV curable fluid film, nano-imprint stamp is pressed in the uV curable film then, removes template behind the ultraviolet light polymerization, forms structure plan; Or this film exposed by mask blank, and further develop, form structure plan.These structure plans can be by traditional process transfer such as plasma etching to substrate material.
Description of drawings
Fig. 1 is the process schematic representation of the inventive method---nano-photoetching is implemented illustration
Embodiment
UV curable composition among the present invention forms uniform fluid film by the method for spin-coating on substrate.In the nano impression process, at room temperature, being pressed in the uV curable composition liquid film of template with convex-concave structure, when template contacts with liquid film, because low, the good fluidity of viscosity of liquid film, capillary force can make the uV curable composition be packed into automatically in the recessed structure of template, and certain pressure is used to make template and substrate to fit.With UV-light the liquid under the template is exposed, solidifies, separate template then, the convex-concave structure on the template just is copied on the solidified liquid film.The photolithographic exposure process, UV-light is exposed to above-mentioned liquid film by mask blank, and the uV curable liquid film is the negative glue of photoetching, exposed portion is cured, after the development, unexposed portion is developed the solvent flush away, exposed portion is stayed on the substrate, and the structure on the mask plate is copied on the substrate.
The photo solidification machine physics and chemistry of uV curable mixture is mainly based on the mechanism of positively charged ion initiated polymerization or the mechanism of free radical initiation among the present invention.
In the photolithographic exposure process, proton or free radical that light trigger produces can spread to unexposed portion from exposed portion, light-initiated reaction simultaneously also can be spread to unexposed portion from exposed portion, cause the photoresist material of unexposed portion that chemical transformation takes place equally, form system deviation, cause the live width of the structure live width of actual generation greater than structure on the mask plate.As the conventional lithography glue material, added the light initiating polymerizing reaction inhibitor in the uV curable composition among the present invention, control the problem of initiator diffusion and polyreaction diffusion.The consumption of light initiating polymerizing reaction inhibitor is about 0.1~25, preferred 1~5% of light trigger consumption molar percentage.For vinyl ether or epoxy systems, light trigger is sulphur, iodine father-in-law ionic optical acid generating agent, alkaline matter can in and the optical acid generating agent hydrogen ion and the active cation that produce, stop polyreaction.Add alkaline trisubstituted organic amine among the present invention as light-initiated cationic polymerization inhibitor, preferred dibutyl thanomin, diisobutyl thanomin, dimethyl undecyl amine, tri-isopropanolamine, sparteine, methyl bicyclic hexyl amine, triisobutyl amine etc.For acrylate, methacrylic ester system, light trigger will produce free radical, add the free radical quencher among the present invention as light-initiated Raolical polymerizable inhibitor, preferred aryl groups benzofuranones, bisphenolmonoacryates compound, hindered amine compound and hydroxylamine compound.
The duplicature system can be with the little structure plan of aspect ratio that forms on uV curable composition liquid film, method by the selectivity plasma etching is enlarged into the big structure plan of aspect ratio on macromolecule membranous layer, structure plan can be copied on the substrate more reliably.In the common macromolecular material of forming by carbon, hydrogen, oxygen, add the ability that the material that contains element silicon can effectively improve material antioxygen gas plasma etching.Add organosilicon material in the uV curable mixture in the present invention, the macromolecule membranous layer of lower floor is the macromolecular material of carbon, hydrogen, oxygen composition, solidify back upper layer of material and subsurface material the oxygen plasma etching is had selectivity, the speed of upper layer film etching is less than the speed of lower membrane etching, therefore the structure plan that forms in the upper layer film can be used as mask, transfer on the lower membrane by the oxygen plasma etching, the aspect ratio of patterning is exaggerated simultaneously.The organosilicon material that adds in the uV curable composition can be to have reactive functional groups, as has the organosilicon material of vinyl ether, epoxy and (methyl) acrylate; Also can the reactive organosilicon material of right and wrong.The organosilicon material that preferably has reactive functional groups can form cross-linked network with other ultraviolet photocureable material simultaneously when ultraviolet light polymerization.Lower floor's macromolecular material among the present invention can be the macromolecule membranous layer behind the curing cross-linked, by copying on the substrate as etch mask bar structure pattern; Also can be soluble thermoplastics type's macromolecule membranous layer, by metal lift from method patterning is copied on the substrate.
Embodiment:
The formula table of mould material: epoxy ultraviolet light polymerization mixture
Resins, epoxy DEN438 | Trifluoromethyl sulfuric acid 4-methoxyl group phenylbenzene sulphur | Tri-isopropanolamine | Chlorobenzene |
4% or 14% | 0.25% | 0.0025% | 93% or 84% |
Adopt as Resins, epoxy indistinctions such as GM-128 Resins, epoxy, E-51; Glycidyl ether based epoxy resin, glycidyl ester based epoxy resin, Racemic glycidol amine epoxy resin, line style aliphatic category Resins, epoxy, alicyclic based epoxy resin all do not have obvious difference by above-mentioned formulation ultraviolet light polymerization mixture.
Above-mentioned epoxy compounds is a reactant with different unsaturated monoprotic acid, adds that employing is different compound modified, makes vinyl ester resin become the various resin series of a big veriety.Adoptable epoxy compounds has bisphenol A epoxide resin and homologue thereof, bisphenol F epoxy resin, novolac epoxy, tetrabromobisphenol Resins, epoxy, diepoxy polyoxytrimethylene or the like; Unsaturated monoprotic acid has vinylformic acid, methacrylic acid, phenylacrylic acid, butenoic acid etc.
Reactive solvent of described thinner right and wrong or reactive monomer such as ethyl acetate or dimethyl formamide and their mixture do not have obvious difference; Or with ethyl vinyl ether, oxyethane, propylene oxide or epoxy chloropropane as thinner, also with above-mentioned prescription.
Select triaryl sulphur or diaryl iodide ion type optical acid generating agent 0.1%; Surplus is a flow agent.
Vinyl ether resin Vectomer 4040 | Self-control vinyl ether siloxanes | Hexafluoro-antimonic acid 4-octyloxy Ben Jibenji iodine | Sparteine | Ethyl vinyl ether or epoxy chloropropane |
4% or 19% | 1% | 0.25% | 0.0025% | 95% or 80% |
Described thinner can also adopt the complete indistinction of methylvinylether, adopts acetone, methylethylketone, and methyl iso-butyl ketone (MIBK), manthanoate, ethyl acetate or dimethyl formamide also do not have obvious difference.Select triaryl sulphur or diaryl iodide ion type optical acid generating agent about 0.1%; Surplus is flow agent (various fluorine silicon flow agents, Angel chemical company produces).
Acrylic resin CN973 | Vinylformic acid silica alkane BYK-UV2500 | Benzophenone | P-cresol | Methyl acrylate or ethyl acetate |
4% or 19% | 1% | 0.25% | 0.0025% | 95% or 80% |
Can also adopt epoxy acrylate BRT2000, vinyl ester resin epoxy acrylate, BRT2000 vinyl ester resin, BRT2000 vinyl ester resin, Hydroxylated acrylic resin all not to have remarkable difference by above-mentioned prescription.
Aforesaid propylene acid esters ultraviolet light polymerization mixture, described thinner can also adopt ethyl propenoate, the complete indistinction of butyl acrylate, adopt methyl methacrylate, Jia Jibingxisuanyizhi, butyl methacrylate also not to have obvious difference.
The solvent based thinner can also adopt chlorobenzene, toluene, and dimethylbenzene, acetone or methylethylketone also do not have obvious difference.The preferred dibenzoyl of light trigger, benzophenone, Benzoin ethyl ether or benzoin isobutyl ether about 0.1%.Other adds photoresponse free radical quencher is that the consumption of inhibitor is about 25% of light trigger consumption molar percentage.Quencher selects phenyl benzofuranone or diphenyl acrylate.
Above-mentioned uV curable material contains the resin of vinyl ether functional group or contains the resin of epoxy-functional; Preferred triaryl sulphur of light trigger or diaryl iodide ion type optical acid generating agent.
When above-mentioned ultraviolet photocureable material is the material of acrylate acrylate group, with radical initiators such as benzophenone, can also use Benzoin ethyl ether or benzoin isobutyl ether light trigger, the initiator division produces free radical under UV-irradiation, two keys of the further initiating methacrylates of free radical, methacrylate based group are opened polymerization, and liquid film is solidified.The consumption of light trigger is 1~10% of an oligopolymer amount weight percent.
Light trigger divides the generation free radical under UV-irradiation, two keys of the further initiating methacrylates of free radical, methacrylate based group are opened polymerization, and liquid film is solidified.The consumption of light trigger is 1~2% of an oligopolymer amount weight percent.
The photoresponse inhibitor is the free radical quencher.The consumption of inhibitor is about 0.1~25% of light trigger consumption molar percentage.Quencher preferred aryl groups benzofuranones, bisphenolmonoacryates compound, hindered amine compound and hydroxylamine compound.
Select the macromolecular material of heat curing-type during application for use, by copying on the substrate as etch mask bar structure pattern or select thermoplastics type's macromolecular material for use, by metal lift from method patterning is copied on the substrate is the method for using always.
Claims (10)
1. solidifiable composition material by ultraviolet light, by the oligopolymer of low viscosity, polyfunctionality, light trigger, thinner constitutes; Low viscosity, the oligopolymer of polyfunctionality is at room temperature to present low viscous liquid, at room temperature the viscosity of oligopolymer is in 1 centipoise/second-10000 centipoise/second, described liquid oligopolymer includes two or more curable crosslinked functional groups, curable functional group is group or the epoxide group that contains carbon carbon unsaturated double-bond, the liquid oligopolymer is selected from the glycidyl ether based epoxy resin, the glycidyl ester based epoxy resin, the Racemic glycidol amine epoxy resin, line style aliphatic category Resins, epoxy or alicyclic based epoxy resin, or epoxy acrylate BRT2000, the vinyl ester resin epoxy acrylate, BRT2000 vinyl ester resin or Hydroxylated acrylic resin; Oligopolymer accounts for the 5-80% of oligopolymer and thinner total weight percent; Reactive solvent of described thinner right and wrong or reactive monomer; Non-reactive solvent is a pentane, hexane, heptane, octane, chlorobenzene, toluene, dimethylbenzene, acetone, methylethylketone, methyl iso-butyl ketone (MIBK), manthanoate, ethyl acetate, dimethyl formamide or their mixture; Or with reactive monomer or their mixture as thinner: reactive monomer is methyl acrylate, ethyl propenoate, butyl acrylate, methyl methacrylate, Jia Jibingxisuanyizhi, butyl methacrylate, methylvinylether, ethyl vinyl ether, oxyethane, propylene oxide or epoxy chloropropane; Thinner accounts for the 95-20% of oligopolymer and thinner total weight percent; The ultraviolet photocureable material that causes based on positively charged ion is the oligopolymer that contains the oligopolymer of vinyl ether group or contain epoxide group, and light trigger selects triaryl sulphur or diaryl iodide ion type optical acid generating agent; Ultraviolet photocureable material based on free radical triggering mechanism is the oligopolymer that contains acrylate group or methacrylate based group, light trigger is selected dibenzoyl, benzophenone, Benzoin ethyl ether, benzoin isobutyl ether or ether compound for use, and the consumption of light trigger is the 1-10% of oligopolymer amount weight percent.
2. solidifiable composition material by ultraviolet light according to claim 1 is characterized in that the crosslinkable reactivity functional group that the liquid oligopolymer has is vinyl ether acrylate group or methacrylate based group.
3. solidifiable composition material by ultraviolet light according to claim 1, it is characterized in that the ultraviolet light polymerization mixture adds light polymerization initiator and light initiating polymerizing reaction inhibitor, the consumption of light initiating polymerizing reaction inhibitor is 0.1~25% of a light trigger consumption molar percentage.
4. according to the solidifiable composition material by ultraviolet light in the claim 3, the functional group that it is characterized in that the curing cross-linked of polyfunctionality oligopolymer is vinyl ether or epoxide group, then light trigger is triaryl sulphur, diaryl iodide ion type optical acid generating agent, the photoresponse inhibitor is three replacement organic amines, is selected from dibutyl thanomin, diisobutyl thanomin, dimethyl undecyl amine, tri-isopropanolamine, sparteine, methyl bicyclic hexyl amine or triisobutyl amine.
5. according to the solidifiable composition material by ultraviolet light in the claim 3, the curable crosslinked functional group that it is characterized in that the polyfunctionality oligopolymer is acrylate or methacrylic ester, then light trigger is dibenzoyl or benzophenone radical initiator, and the photoresponse inhibitor is the free radical quencher; The free radical quencher is aryl benzofuranones, bisphenolmonoacryates compound, hindered amine compound or hydroxylamine compound.
6. according to the solidifiable composition material by ultraviolet light in the claim 3, the consumption that it is characterized in that light trigger is 2~5% of an oligopolymer amount weight percent, and the consumption of light initiating polymerizing reaction inhibitor is 0.1~25% of a light trigger consumption molar percentage.
7. according to the solidifiable composition material by ultraviolet light of claim 3, it is characterized in that adding in the uV curable material matrix material organosilicon material with vinyl ether, epoxy, methacrylate based group; Or non-reacted organosilicon material; Account for the 5-20% of oligopolymer gross weight.
8. the application of ultraviolet photocureable material matrix material, be applied to nano impression glue or be applied to photoetching technique as photoresist material, it is characterized in that comprising double layer material and be used for nano impression or photoetching substrate, upper strata uV curable material composite fluid film layer material is the described material of one of claim 1 to 7, thickness 10-100nm; Lower floor is thermoplastics type or thermosetting macromolecule material membrane transfer layer, thickness 200-1000nm; Thermoplastics type or thermosetting macromolecule material membrane transfer layer by the method for selectivity plasma etching, are delivered to the structure plan for preparing in this tunic in upper layer film; Lower floor's macromolecular material transfer layer is selected the macromolecular material of heat curing-type for use, copy on the substrate or select thermoplastics type's macromolecular material for use by etch mask bar structure pattern, by metal lift from method patterning is copied on the substrate.
9. the application of solidifiable composition material by ultraviolet light according to Claim 8, it is characterized in that solidifying back upper layer of material and subsurface material the oxygen plasma etching is had selectivity, the speed of upper layer film etching is less than the speed of lower membrane etching, therefore the structure plan that forms in the upper layer film can be used as mask, transfer on the lower membrane by the oxygen plasma etching, the aspect ratio of patterning is exaggerated simultaneously; Use has the organosilicon material of reactive functional groups, forms cross-linked network with other ultraviolet photocureable material simultaneously when ultraviolet light polymerization; Lower floor's macromolecular material is the macromolecule membranous layer behind the curing cross-linked, copies on the substrate by etch mask bar structure pattern; Or soluble thermoplastics type's macromolecule membranous layer, by metal lift from method patterning is copied on the substrate.
10. the application of solidifiable composition material by ultraviolet light according to Claim 8, it is characterized in that the little structure plan of aspect ratio that the duplicature system will form on uV curable composition liquid film, method by the selectivity plasma etching is enlarged into the big structure plan of aspect ratio on macromolecule membranous layer, structure plan can be copied on the substrate more reliably.
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CN102408332A (en) * | 2011-11-14 | 2012-04-11 | 无锡英普林纳米科技有限公司 | Ultraviolet curing degradable cross-linking monomer and preparation method thereof |
CN103059717A (en) * | 2012-12-28 | 2013-04-24 | 上海维凯化学品有限公司 | High-leveling-property ultraviolet curable coating composition for shower coating |
US11141919B2 (en) | 2015-12-09 | 2021-10-12 | Holo, Inc. | Multi-material stereolithographic three dimensional printing |
CN107300828B (en) * | 2016-04-15 | 2021-01-15 | 常州强力电子新材料股份有限公司 | Photosensitive resin for 3D printing |
GB2564956B (en) | 2017-05-15 | 2020-04-29 | Holo Inc | Viscous film three-dimensional printing systems and methods |
EP3638485A4 (en) * | 2017-06-16 | 2021-06-16 | Holo, Inc. | Methods and systems for stereolithography three-dimensional printing |
US10245785B2 (en) | 2017-06-16 | 2019-04-02 | Holo, Inc. | Methods for stereolithography three-dimensional printing |
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CN109987580B (en) * | 2019-04-16 | 2020-02-11 | 中国科学院微电子研究所 | Preparation method of nano forest structure and regulation and control method of nano forest structure |
CN110804276A (en) * | 2019-10-18 | 2020-02-18 | 南京大学 | High-resolution photocuring three-dimensional printing compound |
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