CN101957559A - Optical reversible nanoimprint photoresist as well as preparation method and application method thereof - Google Patents
Optical reversible nanoimprint photoresist as well as preparation method and application method thereof Download PDFInfo
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- MMMMKVSPTBGBLC-UHFFFAOYSA-N CC(C)([N]#C)[O](C)=C Chemical compound CC(C)([N]#C)[O](C)=C MMMMKVSPTBGBLC-UHFFFAOYSA-N 0.000 description 1
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Abstract
The invention relates to optical reversible nanoimprint photoresist as well as a preparation method and an application method thereof, belonging to the technical field of semiconductor manufacturing. The photoresist comprises the following component in percentage by weight: 5-50% of optical reversible cross-linking agent, 5-80% of photopolymerisable compound and 0.1-15% of photopolymerization initiator or optical acid-generating agent, wherein the structural formula of the optical reversible cross-linking agent is shown in the specification. With low viscosity, the prepared photoresist is convenient for the technological operations of spin coating and imprinting, and the photoresist has optical reversibility and good etching resistance.
Description
Technical field
What the present invention relates to is a kind of material and method of micro-nano processing technique field, specifically is reversible nano-imprint lithography glue and methods for making and using same thereof of a kind of light.
Background technology
(Nanoimprint Lithography, NIL) the Stephen Y.Chou professor by Princeton University (Princeton University) at first proposed in nineteen ninety-five nanometer embossing, and had obtained a lot of concerns and development in recent years.Compare with other photoetching techniques, owing to saved the cost of optical lithography mask plate and optical imaging apparatus, so NIL has advantages such as low cost, high resolving power, high production capacity.Simultaneously, the characteristics of its preparation high resolving power micro-/ nano yardstick figure make its applicable scope very extensive, comprise fields such as electronics, biology and photonic crystal.
At present, the challenge of nanometer embossing industrialization maximum is the repeatability of impression and the utilization factor of template, because in moulding process, the supporting body template of tradition impression is quartzy the making, not only the cost costliness is very easily broken simultaneously, after working repeatedly, etching glue is bonded at template surface easily, and these residual cure polymers very easily destroy the precision of duplicating of structure.So avoiding residual colloid to be bonded at template surface is necessary.Recently, the development of nanometer embossing concentrates on the new soft template of exploitation basically, fluoridize the template surface technology, perhaps directly in colloid, add the fluorochemical surfactant self assembly and form surperficial unimolecular layer (SAM) raising hydrophobic properties of the surface, so that improve the utilization factor of template, reduce the industrialization cost.But the problem that these methods exist is needing when template surface is handled to carry out high-temperature heating treatment and high pressure; surface fluorination is not put things right once and for all simultaneously; after repeating to impress several tens times; not only need the clean surface residual solids; simultaneously need be at the inferior template surface of fluoridizing, the technological requirement of extensiveization of influence.The present invention is intended to develop a kind of novel reversible photoresist of light, utilize the reversible character of light to make the cured polymer degraded be dissolved in the organic solvent again, reduce of the infringement of the method for conventional cleaning template surface to template, it is promptly capable of washing that the residual curing photoresist of template surface only needs easy processing procedure simultaneously, reduces the surface fluorination technique number of times.
Find that through the retrieval to prior art at present fewer at the method for the photoresist with reversible character, most simultaneously reversible glue is that heat is reversible, needs pyroprocessing to decompose and solidifies photoresist, process is loaded down with trivial details.In heat treatment process, the fluorochemicals that template surface is modified has destruction simultaneously, and the material that may produce acidity or alkalescence in the hot reversible course of reaction, and the quartz template microstructure is had destruction.The present invention is directed to above-mentioned shortcoming, invented the reversible crosslinking chemical of a kind of light, and further prepared the reversible nano impression glue of light.Utilize the reversible character of light, the template surface residual polyalcohol promptly can decompose under the condition of gentleness and is dissolved in the solvent, whole process has reduced the corrosive attack of heat treated product to template simultaneously to the basic no influence of the fluorine-containing layer of template, has improved the utilization factor of template.
Summary of the invention
The present invention is directed to the prior art above shortcomings, provide a kind of light reversible nano-imprint lithography glue and methods for making and using same thereof, the reversible characteristic of the light of the photoresist for preparing has effectively reduced the infringement of the method for conventional cleaning template surface to template, utilize this photoresist to prepare the high-precision nano-scale graphic structure of large tracts of land simultaneously, and have higher anti-etching performance.
The present invention is achieved by the following technical solutions:
The present invention relates to a kind of crosslinking chemical for preparing photoresist, its molecular structural formula is:
Wherein: R
1, R
2, R
3And R
4Be respectively hydrogen atom, C
1-C
10Alkyl, C
1-C
10Alkoxy, halogen, cyano group, hydroxyl, C
2-C
10Thiazolinyl, C
2-C
10Alkynyl or C
3-C
10Naphthenic base, n is the integer of 1-10.
Described R
1Preferred hydrogen, C
1-C
6Alkyl, C
1-C
6Alkoxy, halogen, cyano group, hydroxyl, C
2-C
6Thiazolinyl, C
2-C
6Alkynyl or C
3-C
6Naphthenic base; Further preferred hydrogen or methyl.
Described R
2Preferred hydrogen, C
1-C
6Alkyl, C
1-C
6Alkoxy, halogen, cyano group, hydroxyl, C
2-C
6Thiazolinyl, C
2-C
6Alkynyl or C
3-C
6Naphthenic base; Further preferred hydrogen or methyl.
Described R
3Preferred hydrogen atom, C
1-C
10Alkyl, C
1-C
10Alkoxy, halogen, cyano group, hydroxyl, C
2-C
10Thiazolinyl, C
2-C
10Alkynyl or C
3-C
10Naphthenic base; Further preferred hydrogen or methyl.
Described R
4Preferred hydrogen atom, C
1-C
10Alkyl, C
1-C
10Alkoxy, halogen, cyano group, hydroxyl, C
2-C
10Thiazolinyl, C
2-C
10Alkynyl or C
3-C
10Naphthenic base; Further preferred hydrogen or methyl.
The integer of the preferred 1-8 of described n; Further preferred 2 or 3.
The crosslinking chemical of described preparation photoresist, its molecular structural formula is preferably:
The present invention relates to the preparation method of above-mentioned crosslinking chemical, comprise the steps:
The first step, make the reaction of coumarin compound and halohydrin, form the coumarin derivative shown in the following structure:
The structural formula of described coumarin compound is:
The structural formula of described halohydrin is:
In the formula: R
1Be selected from hydrogen atom, C
1-C
10Alkyl, C
1-C
10Alkoxy, halogen, cyano group, hydroxyl, C
2-C
10Thiazolinyl, C
2-C
10Alkynyl and C
3-C
10Naphthenic base; X is a halogen; N represents the integer of 1-10;
Second goes on foot, makes coumarin derivative and the reaction of halo acetyl compound, prepares crosslinking chemical;
The structural formula of described halo acetyl compound is:
In the formula: X is a halogen; R
2, R
3And R
4Be selected from hydrogen atom, C independently of one another
1-C
10Alkyl, C
1-C
10Alkoxy, halogen, cyano group, hydroxyl, C
2-C
10Thiazolinyl, C
2-C
10Alkynyl and C
3-C
10Naphthenic base.
Of the present inventionly relate to the reversible nano-imprint lithography glue of light that above-mentioned crosslinking chemical prepares, its component and mass percentage content are: light reversible cross-linking agent 5～50%, optical polymerism compound 5～80% and be Photoepolymerizationinitiater initiater or photoacid generator 0.1%～15%, the weight sum of each component is 100%.
The preferred acrylic acid 2-[(4-of described smooth reversible cross-linking agent methylcoumarin base-7-yl) oxygen base]-ethyl ester (AHEMC), acrylic acid 2-[(2-oxo-2H-1-chromene-7-yl) the oxygen base]-ethyl ester (AHEC) or methacrylic acid 2-[(4-methylcoumarin base-7-yl) the oxygen base]-ethyl ester (MAHEMC).
Described optical polymerism compound is meant: the optical polymerism compound with at least one polymerizable group comprises: acrylate compounds, methacrylate compound, epoxy compound, oxetane compound, a kind of or its combination in vinyl ether compound or the distyryl compound, as: (methyl) acrylic acid phenoxy group diol ester, (methyl) acrylic acid phenoxy group glycol ester, (methyl) acrylic acid 2-phenoxy ethyl, (methyl) acrylic acid phenoxy group macrogol ester, (methyl) n-butyl acrylate, (methyl) tert-butyl acrylate, (methyl) acrylic acid methoxyl triglycol ester, (methyl) acrylic acid methoxy poly (ethylene glycol) ester, (methyl) acrylic acid mountain
Alcohol ester, (methyl) benzyl acrylate, (methyl) acrylic acid 1-adamantane esters, (methyl) isobornyl acrylate, (methyl) tridecyl acrylate, (methyl) acrylic acid bay alcohol ester, (methyl) acrylic acid octyloxy macrogol ester, (methyl) acrylic acid 2-hydroxyl-3-phenoxy group propyl ester, (methyl) acrylic acid isooctadecanol ester, (methyl) acrylic acid bay alcohol ester, two (methyl) polyalkylene glycol acrylate ester, ethoxylation bisphenol-A two (methyl) acrylate, propoxylated bisphenol two (methyl) acrylate, two (methyl) acrylic acid 1,10-decanediol ester, two (methyl) acrylic acid cyclodecane diformazan alcohol ester, two (methyl) acrylic acid ethoxylation-2-methyl 1, the ammediol ester, two (methyl) acrylic acid binaryglycol ester, two (methyl) acrylic acid 1, the 4-butanediol ester, two (methyl) acrylic acid DOPCP, two (methyl) acrylic acid 2,2,3,3,4,4,5,5-octafluoro-1, the own ester of 6-, (methyl) acrylic acid 2-hydroxyl-3-acryloxy propyl ester, two (methyl) acrylic acid ethyl, propoxylation ethoxylation bisphenol-A two (methyl) acrylate, two (methyl) acrylic acid 1,6-hexanediol ester, but be not limited to this.They can use separately or be used in combination more than 2 kinds.
Described epoxy compound comprises: bisphenol A diglycidyl ether, Bisphenol F diglycidyl ether, bisphenol-S diglycidyl ether, brominated bisphenol A diglycidyl ether, brominated bisphenol F diglycidyl ether, brominated bisphenol S diglycidyl ether, hydrogenated bisphenol A diglycidyl ether, A Hydrogenated Bisphenol A F diglycidyl ether, A Hydrogenated Bisphenol A S diglycidyl ether, 1,4-butanediol diglycidyl ether, 1,6-hexanediol diglycidyl ether, T 55, trihydroxymethylpropanyltri diglycidyl ether, polyethyleneglycol diglycidylether etc., but be not limited to this.They can use separately or be used in combination more than 2 kinds.
Described oxetane compound comprises: 3-ethyl-3-methylol oxetanes, 3-(methyl) allyloxy methyl-3-ethyl oxetanes, (3-ethyl-3-oxa-cyclobutyl methoxy base) methylbenzene, 4-fluoro-(1-(3-ethyl-3-oxa-cyclobutyl methoxy base) methyl) benzene, 4-methoxyl-(1-(3-ethyl-3-oxa-cyclobutyl methoxy base) methyl) benzene, (1-(3-ethyl-3-oxa-cyclobutyl methoxy base) ethyl) phenyl ether, isobutoxy methyl (3-ethyl-3-oxa-cyclobutylmethyl) ether, isoborneol oxygen base ethyl (3-ethyl-3-oxa-cyclobutylmethyl) ether, isobornyl (3-ethyl-3-oxa-cyclobutylmethyl) ether etc., but be not limited to this.They can use separately or be used in combination more than 2 kinds.
Described vinyl ether compound comprises: n-propyl vinyl ether, n-butyl vinyl ether, the n-hexyl vinyl ether, tert-Butyl vinyl ether, uncle's amido vinyl ether, cyclohexyl vinyl ether, vinyl aryl ether, dodecyl vinyl, the ethylene glycol butyl vinyl ether, the ethylhexyl vinyl ether, IVE, the polyglycol methyl vinyl ether, the triethylene glycol methyl vinyl ether, the triethylene glycol divinyl ether, the butylene glycol divinyl ether, the cyclohexanedimethanol divinyl ether, the diethylene glycol divinyl ether, the hexanediol divinyl ether, the TEG divinyl ether, 1,4-butylene glycol divinyl ether, tristane dimethanol divinyl ether, trimethoxy propane trivinyl ether etc., but be not limited to this.They can use separately or be used in combination more than 2 kinds.
Described distyryl compound comprises: styrene, p-methylstyrene, to methoxy styrene, Beta-methyl styrene, to methyl-Beta-methyl styrene, α-Jia Jibenyixi, to methoxyl-Beta-methyl styrene, para hydroxybenzene ethene etc., but be not limited to this.They can use separately or be used in combination more than 2 kinds.
Described optical polymerism compound is preferably the optical polymerism compound of the ring texture with at least one polymerizable group, and described ring texture is aliphatics ring or aromatic ring;
Described aliphatics ring comprises: the naphthenic base of carbon number 4～12 and the hydrogen atom of these groups be optionally substituted that base replaces and group;
Described aromatic ring comprises: the hydrogen atom of phenyl, naphthyl, furyl, pyrrole radicals etc. and these groups be optionally substituted that base replaces and group.
The preferred ethylenic unsaturated link of described polymerizable group, more preferably any in (methyl) acrylate, vinyl ether, allyl ether or the styrene considered from the angle of the curable of photosensitive polymer combination, more preferably (methyl) acrylate.In a preferred embodiment of the present invention, be selected from benzyl methacrylate, the phenoxy group EDIA.
Described optical polymerism compound is the optical polymerism compound with ring texture of the polymerizable group more than two, and its mass percent that is arranged in the reversible nano-imprint lithography glue of light is 5～60%, more preferably 15～40%.
Described Photoepolymerizationinitiater initiater comprises: 2; 2-dimethoxy-1; 2-diphenylethane-1-ketone; 1-hydroxyl-cyclohexyl-phenyl-ketone; 2-hydroxy-2-methyl-1-phenyl-propane-1-ketone; benzophenone; 1-[4-(2-hydroxyl-oxethyl)-phenyl]-2-hydroxy-2-methyl-1-propane-1-ketone; 2-methyl isophthalic acid-[4-(methyl mercapto) phenyl]-2-morpholino-propane-1-ketone; 2-benzyl-2-dimethylamino-1-(4-morpholino phenyl)-butanone-1; two (2; 6-dimethoxy benzoyl)-2; 4; 4-trimethyl-amyl group phosphine oxide; 2-hydroxy-2-methyl-1-phenyl-propane-1-ketone; two (2; 4; the 6-trimethylbenzoyl)-phenyl phosphine oxide; two (η 5-2; 4-cyclopentadiene-1-yl)-two (2; 6-two fluoro-3-(1H-pyrroles-1-yl)-phenyl) titanium; 2-(dimethylamino)-2-[(4-aminomethyl phenyl) methyl]-1-[4-(4-morpholinyl) phenyl]-the 1-butanone, preferred 2-methyl isophthalic acid-[4-(methyl mercapto) phenyl]-2-morpholino-propane-1-ketone.
Described photoacid generator comprises: salt such as diazo salt, salt compounded of iodine, bromine salt, villaumite, sulfosalt, selenium salt, pyralium salt, thiapyran salt, pyridiniujm; Halogenated compounds such as three (trihalomethyl group)-s-triazines and derivant thereof; The 2-nitrobenzyl ester of sulfonic acid; The imino group sulphonic acid ester; 1-oxo-2-diazo naphthoquinone-4-sulfonate derivatives; N-oxyimino sulphonic acid ester; Three (mesyloxy) benzene derivative; Two sulfonyl diazomethane classes; Sulfonyl carbonyl paraffinic; Sulfonyl carbonyl diazomethane class; Two sulphones etc.
The reversible nano-imprint lithography glue of light the present invention relates to the preparation method of the reversible nano-imprint lithography glue of above-mentioned light, by will be prepared after light reversible cross-linking agent, light trigger and the optical polymerism compound.
The present invention relates to the application process of the reversible nano-imprint lithography glue of above-mentioned light, by after being dissolved in described photoresist in the anhydrous chloroform and being diluted to mass concentration 5%, by 0.2 micron filtrator photoresist solution is carried out micro-filtration and be placed on and preserve under the lucifuge freezing environment or be used for the etching semiconductor silicon chip.
The reversible nano-imprint lithography glue of described light is in a liquid state at following monomer whose of normal temperature (15～30 ℃) and oligomer, in the scope of the viscosity under 25 ℃ below 20mPas, better is in the scope of 3～15mPas, is more preferably in the scope of 8～13mPas.By making it have such viscosity, can give formation ability, coating performance and other processing characteristics of the micro concavo-convex pattern before solidifying, after curing, can give resolution, residual membrane property, substrate adaptation or all good rerum natura of filming of other all many-side.If the viscosity of photosensitive polymer combination surpasses 20mPas, and is then poor to the servo-actuated of relief pattern, need longer time and stronger pressurization that it is filled to mould.
The present invention is directed to the unmanageable technical matters of traditional imprint lithography glue, design and synthesize out a kind of crosslinking chemical, and then prepare the photoresist that is applicable to nano impression with optical reciprocity matter.Compare with existing photoresist, its technique effect comprises:
1. low-viscosity is convenient to the operation of spin coating coating and imprint process.
2. light is reversible, is convenient to clean template surface, improves the work efficiency of template.
3. low-pressure fully reduces because the infringement that high pressure causes template.
4. low the contraction guarantees the least amount of deformation in the solidification process, guarantees high replica precision.
5. anti-etching good, can improve the etching efficient of base material, be convenient to figure transfer, guarantee etching precision.
Description of drawings
Fig. 1 has described the nuclear magnetic resoance spectrum of intermediate HEMC of the present invention.
Fig. 2 has described the nuclear magnetic resoance spectrum of crosslinking chemical AHEMC of the present invention.
Fig. 3 has described the technological process of impression and figure transfer.
Fig. 4 has described the SEM figure behind AHEMC-photoresist-1 impression.
Fig. 5 has described the SEM figure of figure transfer to silicon base.
Fig. 6 a has described the ultraviolet spectrum of photoresist coating after through the uv-exposure of 365nm wave band.
Fig. 6 b has described the ultraviolet spectrum of photoresist coating after through the uv-exposure of 254nm wave band.
Embodiment
Below embodiments of the invention are elaborated, present embodiment is being to implement under the prerequisite with the technical solution of the present invention, provided detailed embodiment and concrete operating process, but protection scope of the present invention is not limited to following embodiment.
Embodiment 1 smooth reversible cross-linking agent acrylic acid 2-[(4-methylcoumarin base-7-yl) oxygen base]-ethyl ester (AHEMC) preparation
Get 10.0g (56.7mmol) 4-methylcoumarin, 100mmol ethylene bromohyrin, 120mmol sal tartari are measured the dissolving of 450ml acetone solvent in there-necked flask.Potpourri refluxed suction filtration 3 hours at 60 ℃.The evaporation of gained solution rotating is with solvent evaporated, and recrystallization in ethanol obtains midbody product HEMC again, yield 95%.
Get 2g HEMC, 2g triethanolamine (TEA), the 40ml chloroform is in there-necked flask.In ice-water bath, dropwise drip 3g acrylamide (AC), stirring reaction 2 hours.Continued at room temperature stirring reaction 6 hours.Stop reaction, standing demix, chloroform layer is washed respectively with dilute sulfuric acid and is given a baby a bath on the third day after its birth time then, then adds the material that anhydrous magnesium sulfate is removed remained unreacted in chloroform layer.At last, the gained chloroformic solution obtains final required light reversible cross-linking agent AHEMC, yield 70%-75% at the rotation evaporate to dryness.
The preparation of the reversible impression glue of embodiment 2 light AHEMC-photoresist-1
Take by weighing embodiment 1 gained light reversible cross-linking agent AHEMC 0.1g, light trigger I-907 (Changzhou Tronly New Electronic Materials Co., Ltd.) 0.015g respectively, monomer phenoxy group EDIA (Xin Zhong village chemical industry Co., Ltd.) 1.0g joins in the reagent bottle one by one, mix, obtain photoresist.Take by weighing gained photoresist 1.0g, it is diluted to mass concentration 5% with anhydrous chloroform.Use 0.2 micron filtrator photoresist solution to be carried out micro-filtration, the freezing preservation of lucifuge.
The preparation of the reversible impression glue of embodiment 3 light AHEMC-photoresist-2
Take by weighing embodiment 1 gained light reversible cross-linking agent AHEMC 0.3g respectively, light trigger I-907 (Changzhou Tronly New Electronic Materials Co., Ltd.) 0.015g, monomer phenoxy group EDIA (Xin Zhong village chemical industry Co., Ltd.) 1.0g joins in the reagent bottle one by one, mix, obtain photoresist.Take by weighing gained photoresist 1.0g, it is diluted to mass concentration 5% with anhydrous chloroform.Use 0.2 micron filtrator photoresist solution to be carried out micro-filtration, the freezing preservation of lucifuge.
The preparation of the reversible impression glue of embodiment 4 light AHEMC-photoresist-3
Take by weighing embodiment 1 gained light reversible cross-linking agent AHEMC 0.3g respectively, light trigger I-907 (Changzhou Tronly New Electronic Materials Co., Ltd.) 0.030g, monomer benzyl methacrylate (lark prestige) 1.0g joins in the reagent bottle one by one, mixes, and obtains photoresist.Take by weighing gained photoresist 1.0g, it is diluted to mass concentration 5% with anhydrous chloroform.Use 0.2 micron filtrator photoresist solution to be carried out micro-filtration, the freezing preservation of lucifuge.
The preparation of the reversible impression glue of embodiment 5 light AHEMC-photoresist-4
Take by weighing embodiment 1 gained light reversible cross-linking agent AHEMC 0.3g respectively, light trigger Irgacure 184 (1-hydroxycyclohexylphenylketone) (Changzhou Tronly New Electronic Materials Co., Ltd.) 0.030g, monomer 1.0g benzyl methacrylate (lark prestige) joins in the reagent bottle one by one, mix, obtain photoresist.Take by weighing gained photoresist 1.0g, it is diluted to mass concentration 5% with anhydrous chloroform.Use 0.2 micron filtrator photoresist solution to be carried out micro-filtration, the freezing preservation of lucifuge.
Reversible glue laminated seal of embodiment 6AHEMC-photoresist-1 and figure transfer technology
What Fig. 3 described is the impression of photoresist of the present invention and the technology and the condition thereof of figure transfer.
1. substrate modification: silicon chip substrate to be finished is placed 98%H
2SO
4: 30%H
2O
2In 3: 1 the mixed solution of volume ratio, handled 3 hours in 150 ℃.Then, with acetone, alcohol elder generation post-flush several, drying, then in 120 ℃ of vacuum drying 12h.Dried silicon chip is immersed in the anhydrous toluene solution of 0.2wt%3-(trimethoxysilyl) propyl group-2-methyl-2-acrylate (MAPTES), sealing was preserved 4 hours.Clean silicon chip with acetone, nitrogen dries up with standby.
2. adopt spin coating proceeding whirl coating on silicon chip: the AHEMC-photoresist-1 of embodiment 2 gained, low speed 300rpm, time 10s; High speed 3000rpm, time 20s.
3. the quartz template that will be the lattice structure of 1.4 μ m the cycle is covered on colloid, puts into nano marking press together with silicon chip.Shown in Fig. 2-B, vacuumized 3 minutes, apply the pressure of 10psi, pressurize 20 minutes to template.
4. shown in Fig. 1-C, silicon chip exposed 15 minutes under the ultraviolet source of 365nm together with quartz template.After treating that photoresist solidifies, directly carry out the demoulding.Fig. 4 is the SEM figure of impression back cure polymer, illustrates that photoresist of the present invention can support the high resolving power level.
5. sample after the demoulding is placed and carry out etching in the reactive ion etching vacuum chamber, the vacuum chamber base vacuum is 5 * 10
-3Pa.Etching gas SF
6The silicon substrate that is etched to lower floor exposes, and shown in Fig. 1-E, flow is 20sccm, and power is 40w, and air pressure is 60mTorr, etching time 120s.
The reversible glue laminated seal of embodiment 7AHEMC-photoresist-2
Whole processing step and parameter remain unchanged, different AHEMC-photoresist-2 photoresists that is to use embodiment 3 gained.
The reversible glue laminated seal of embodiment 8AHEMC-photoresist-3
Whole processing step and parameter remain unchanged, different AHEMC-photoresist-3 photoresists that is to use embodiment 4 gained.
The reversible glue laminated seal of embodiment 9AHEMC-photoresist-4
Whole processing step and parameter remain unchanged, different AHEMC-photoresist-4 photoresists that is to use embodiment 5 gained.
Embodiment 10 solidifies the light invertible dissolution of reversible glue AHEMC-photoresist 1
After experimental example 6 step 5 demouldings, the pointolite that the polymer film that solidifies figure is positioned over 254nm continues exposure 2 hours down, is placed in the chloroform solvent polymer film dissolving of breaking gradually then.Shown in Fig. 5 b, behind the uv-exposure through the 254nm wave band, the intensity of characteristic absorption peak raises, comparison diagram 5a is at the uv-exposure collection of illustrative plates of 365nm wave band, illustrate that the polymkeric substance after solidifying can reversiblely degrade, after 3 hours, polymer film is dissolved in the chloroform solvent substantially.
Embodiment 11 solidifies the light invertible dissolution of reversible glue AHEMC-photoresist 2
The pointolite that AHEMC-photoresist 2 polymer films after the demoulding is positioned over 254nm continues down exposure 2 hours, is placed in the chloroform solvent polymer film dissolving of breaking gradually then.10 gained results are consistent with experimental example.
Embodiment 12 solidifies the light invertible dissolution of reversible glue AHEMC-photoresist 3
The pointolite that AHEMC-photoresist 3 polymer films after the demoulding is positioned over 254nm continues exposure 2 hours down, is placed on then in the chloroform solvent, and polymer film breaks gradually, dissolving.10 gained results are consistent with experimental example.
Embodiment 13 solidifies the light invertible dissolution of reversible glue AHEMC-photoresist 4
The pointolite that AHEMC-photoresist 4 polymer films after the demoulding is positioned over 254nm continues down exposure 2 hours, is placed in the chloroform solvent polymer film dissolving of breaking gradually then.10 gained results are consistent with experimental example.
Comparative example 1 commercial glue Watershed 11110 impression and figure transfer
Whole processing step and parameter are basic identical with embodiment 6, the different commercially available commercial photoresist Watershed-Resist (German DSM Somos company) that are to use.Because commercial adhesiveness is bigger, the whirl coating spin coating proceeding is adjusted a little, and its method is as follows: adopt spin coating proceeding whirl coating on silicon chip: low speed 300rpm, time 10s; Middling speed 2000rpm, time 20s; High speed 4000rpm, time 20s.This commerce glue Watershed-Resist does not have reversible degradability.
Comparative example 2 commercial glue mr-NIL 6000 impression and figure transfer
The basic embodiment of whole processing step and parameter 6 is identical, the different commercially available commercial photoresist mr-NIL 6000 (U.S. micro resist technology GmbH company) that are to use.Because commercial adhesiveness is bigger, the whirl coating spin coating proceeding is adjusted a little, and its method is as follows: adopt spin coating proceeding whirl coating on silicon chip: low speed 300rpm, time 10s; Middling speed 2000rpm, time 20s; High speed 6000rpm, time 40s.This commerce glue Resist 6000 does not have reversible degradability.
Carry out various performance tests for above-mentioned three kinds of nano impressions with the ultraviolet light polymerization etching glue, it the results are shown in Table 1.Existing commercial nano impression matrix does not originally have reversibility, the residual polyalcohol that sticks on the template generally all is to adopt concentrated sulphuric acid high temperature heating and decomposition, fluorochemicals that not only can deface, the microstructure of the damaged template of meeting after repeatedly handling, and the template after handling will be modified fluorochemicals again.Compare with common commercial glue, photoresist provided by the present invention, because its optical reciprocity energy, the template surface residual polyalcohol promptly can decompose under the condition of gentleness and is dissolved in the solvent in the nano impression process, to not damage of formwork structure, and the fluorochemicals that template is modified does not have influence substantially, has improved the utilization factor of template greatly.
Under 25 ℃, by the flowing water time of fluid sample and water, the viscosity calculations of sample rate and water draws sample viscosity by the Ubbelohde viscosity apparatus, and concrete computing formula is as follows:
Wherein, ρ
iAnd ρ
0Be respectively density, t for sample rate and water
iAnd t
0Be respectively sample and water and flow through the required time of equal volume, if reference liquid H under known certain temperature
2The viscosity of O is η
0And ρ
0, and record ρ
i, t
0, t
iCan try to achieve the viscosity of the sample under this temperature.
Vacuum tightness is respectively the vacuum tightness of marking press in the corresponding moulding process and the time shutter of ultraviolet photoresist with the time shutter, as 3 and 4 scheme of step in the implementation column 6.
SF
6Etch rate and etching selection method:
Etch rate: V=H/t, wherein H is the degree of depth of etching, t is the etching required time.
Etching selection: etching selection is meant the speed ratio of photoresist and substrate etching.
Whole etching process is to finish in the plasma etching machine that Alcatel company provides.
Claims (29)
1. a crosslinking chemical for preparing photoresist is characterized in that, its molecular structural formula is:
Wherein: R
1, R
2, R
3And R
4Be respectively hydrogen atom, C
1-C
10Alkyl, C
1-C
10Alkoxy, halogen, cyano group, hydroxyl, C
2-C
10Thiazolinyl, C
2-C
10Alkynyl or C
3-C
10Naphthenic base, n is the integer of 1-10.
2. the crosslinking chemical of preparation photoresist according to claim 1 is characterized in that, described R
1Be hydrogen, C
1-C
6Alkyl, C
1-C
6Alkoxy, halogen, cyano group, hydroxyl, C
2-C
6Thiazolinyl, C
2-C
6Alkynyl or C
3-C
6Naphthenic base.
3. the crosslinking chemical of preparation photoresist according to claim 1 is characterized in that, described R
2Be hydrogen, C
1-C
6Alkyl, C
1-C
6Alkoxy, halogen, cyano group, hydroxyl, C
2-C
6Thiazolinyl, C
2-C
6Alkynyl or C
3-C
6Naphthenic base.
4. the crosslinking chemical of preparation photoresist according to claim 1 is characterized in that, described R
3Be hydrogen atom, C
1-C
10Alkyl, C
1-C
10Alkoxy, halogen, cyano group, hydroxyl, C
2-C
10Thiazolinyl, C
2-C
10Alkynyl or C
3-C
10Naphthenic base.
5. the crosslinking chemical of preparation photoresist according to claim 1 is characterized in that, described R
4Be hydrogen atom, C
1-C
10Alkyl, C
1-C
10Alkoxy, halogen, cyano group, hydroxyl, C
2-C
10Thiazolinyl, C
2-C
10Alkynyl or C
3-C
10Naphthenic base.
6. the crosslinking chemical of preparation photoresist according to claim 1 is characterized in that, described n is the integer of 1-8.
7. according to the crosslinking chemical of arbitrary described preparation photoresist in the claim 1 to 6, it is characterized in that described R
1, R
2, R
3And R
4Be respectively hydrogen or methyl, n is 2 or 3.
8. the crosslinking chemical of preparation photoresist according to claim 1 is characterized in that, the crosslinking chemical of described preparation photoresist, and its molecular structural formula is:
9. the preparation method according to the described crosslinking chemical of above-mentioned arbitrary claim is characterized in that, comprises the steps:
The first step, make the reaction of coumarin compound and halohydrin, form the coumarin derivative shown in the following structure:
The structural formula of described coumarin compound is:
The structural formula of described halohydrin is:
In the formula: R
1Be selected from hydrogen atom, C
1-C
10Alkyl, C
1-C
10Alkoxy, halogen, cyano group, hydroxyl, C
2-C
10Thiazolinyl, C
2-C
10Alkynyl and C
3-C
10Naphthenic base; X is a halogen; N represents the integer of 1-10;
Second goes on foot, makes coumarin derivative and the reaction of halo acetyl compound, prepares crosslinking chemical;
The structural formula of described halo acetyl compound is:
In the formula: X is a halogen; R
2, R
3And R
4Be selected from hydrogen atom, C independently of one another
1-C
10Alkyl, C
1-C
10Alkoxy, halogen, cyano group, hydroxyl, C
2-C
10Thiazolinyl, C
2-C
10Alkynyl and C
3-C
10Naphthenic base.
10. reversible nano-imprint lithography glue of light for preparing according to the described crosslinking chemical of above-mentioned arbitrary claim, it is characterized in that, its component and mass percentage content are: light reversible cross-linking agent 5～50%, optical polymerism compound 5～80% and be Photoepolymerizationinitiater initiater or photoacid generator 0.1%～15%, the weight sum of each component is 100%.
11. reversible nano-imprint lithography glue of light for preparing according to the described crosslinking chemical of above-mentioned arbitrary claim, it is characterized in that, the nano-imprint lithography glue that described light is reversible, its component and mass percentage content are: light reversible cross-linking agent 15～40%, optical polymerism compound 15～60% and Photoepolymerizationinitiater initiater or photoacid generator 0.5～5%, the weight sum of each component is 100%.
12. the reversible nano-imprint lithography glue of light for preparing according to claim 10 or 11 described crosslinking chemicals, it is characterized in that described smooth reversible cross-linking agent is acrylic acid 2-[(4-methylcoumarin base-7-yl) the oxygen base]-ethyl ester, acrylic acid 2-[(2-oxo-2H-1-chromene-7-yl) the oxygen base]-ethyl ester or methacrylic acid 2-[(4-methylcoumarin base-7-yl) the oxygen base]-ethyl ester.
13. the reversible nano-imprint lithography glue of light according to claim 10 or 11 described crosslinking chemicals prepare is characterized in that described optical polymerism compound is meant: the optical polymerism compound with at least one polymerizable group.
14. the nano-imprint lithography glue that the light that crosslinking chemical according to claim 13 prepares is reversible, it is characterized in that described optical polymerism compound with at least one polymerizable group comprises: a kind of or its combination in acrylate compounds, methacrylate compound, epoxy compound, oxetane compound, vinyl ether compound or the distyryl compound.
15. the nano-imprint lithography glue that the light that crosslinking chemical according to claim 14 prepares is reversible, it is characterized in that, described epoxy compound comprises: bisphenol A diglycidyl ether, the Bisphenol F diglycidyl ether, bisphenol-S diglycidyl ether, brominated bisphenol A diglycidyl ether, brominated bisphenol F diglycidyl ether, brominated bisphenol S diglycidyl ether, the hydrogenated bisphenol A diglycidyl ether, A Hydrogenated Bisphenol A F diglycidyl ether, A Hydrogenated Bisphenol A S diglycidyl ether, 1, the 4-butanediol diglycidyl ether, 1, the 6-hexanediol diglycidyl ether, T 55, a kind of or its combination in trihydroxymethylpropanyltri diglycidyl ether or the polyethyleneglycol diglycidylether.
16. the nano-imprint lithography glue that the light that crosslinking chemical according to claim 14 prepares is reversible, it is characterized in that described oxetane compound comprises: 3-ethyl-3-methylol oxetanes, 3-(methyl) allyloxy methyl-3-ethyl oxetanes, (3-ethyl-3-oxa-cyclobutyl methoxy base) methylbenzene, 4-fluoro-(1-(3-ethyl-3-oxa-cyclobutyl methoxy base) methyl) benzene, 4-methoxyl-(1-(3-ethyl-3-oxa-cyclobutyl methoxy base) methyl) benzene, (1-(3-ethyl-3-oxa-cyclobutyl methoxy base) ethyl) phenyl ether, isobutoxy methyl (3-ethyl-3-oxa-cyclobutylmethyl) ether, a kind of or its combination in isoborneol oxygen base ethyl (3-ethyl-3-oxa-cyclobutylmethyl) ether or isobornyl (3-ethyl-3-oxa-cyclobutylmethyl) ether.
17. the nano-imprint lithography glue that the light that crosslinking chemical according to claim 14 prepares is reversible, it is characterized in that, described vinyl ether compound comprises: n-propyl vinyl ether, n-butyl vinyl ether, the n-hexyl vinyl ether, tert-Butyl vinyl ether, uncle's amido vinyl ether, cyclohexyl vinyl ether, vinyl aryl ether, dodecyl vinyl, the ethylene glycol butyl vinyl ether, the ethylhexyl vinyl ether, IVE, the polyglycol methyl vinyl ether, the triethylene glycol methyl vinyl ether, the triethylene glycol divinyl ether, the butylene glycol divinyl ether, the cyclohexanedimethanol divinyl ether, the diethylene glycol divinyl ether, the hexanediol divinyl ether, the TEG divinyl ether, 1,4-butylene glycol divinyl ether, a kind of or its combination in tristane dimethanol divinyl ether or the trimethoxy propane trivinyl ether.
18. the nano-imprint lithography glue that the light that crosslinking chemical according to claim 14 prepares is reversible, it is characterized in that described distyryl compound comprises: styrene, p-methylstyrene, to methoxy styrene, Beta-methyl styrene, to methyl-Beta-methyl styrene, α-Jia Jibenyixi, to a kind of or its combination in methoxyl-Beta-methyl styrene or the para hydroxybenzene ethene.
19. the reversible nano-imprint lithography glue of light according to claim 10 or 11 described crosslinking chemicals prepare is characterized in that described optical polymerism compound is preferably the optical polymerism compound of the ring texture with at least one polymerizable group.
20. the nano-imprint lithography glue that the light that crosslinking chemical according to claim 19 prepares is reversible is characterized in that, described ring texture is aliphatics ring or aromatic ring.
21. the nano-imprint lithography glue that the light that crosslinking chemical according to claim 20 prepares is reversible is characterized in that, described aliphatics ring comprises: the naphthenic base of carbon number 4～12 and the hydrogen atom of these groups be optionally substituted that base replaces and group; Described aromatic ring comprises: the hydrogen atom of phenyl, naphthyl, furyl, pyrrole radicals etc. and these groups be optionally substituted that base replaces and group.
22. the nano-imprint lithography glue that the light that crosslinking chemical according to claim 19 prepares is reversible is characterized in that, described polymerizable group is the ethylenic unsaturated link.
23. the reversible nano-imprint lithography glue of light according to claim 19 or 22 described crosslinking chemicals prepare is characterized in that described polymerizable group is (methyl) acrylate, vinyl ether, allyl ether or styrene.
24. the reversible nano-imprint lithography glue of light for preparing according to claim 10 or 11 described crosslinking chemicals, it is characterized in that, described optical polymerism compound is the optical polymerism compound with ring texture of the polymerizable group more than two, and its mass percent that is arranged in the reversible nano-imprint lithography glue of light is 15～40%.
25. the reversible nano-imprint lithography glue of light for preparing according to claim 10 or 11 described crosslinking chemicals; it is characterized in that; described Photoepolymerizationinitiater initiater comprises: 2; 2-dimethoxy-1; 2-diphenylethane-1-ketone; 1-hydroxyl-cyclohexyl-phenyl-ketone; 2-hydroxy-2-methyl-1-phenyl-propane-1-ketone; benzophenone; 1-[4-(2-hydroxyl-oxethyl)-phenyl-2-hydroxy-2-methyl-1-propane-1-ketone; 2-methyl isophthalic acid-[4-(methyl mercapto) phenyl-2-morpholino-propane-1-ketone; 2-benzyl-2-dimethylamino-1-(4-morpholino phenyl)-butanone-1; two (2; 6-dimethoxy benzoyl)-2; 4; 4-trimethyl-amyl group phosphine oxide; 2-hydroxy-2-methyl-1-phenyl-propane-1-ketone; two (2; 4; the 6-trimethylbenzoyl)-phenyl phosphine oxide; two (η 5-2; 4-cyclopentadiene-1-yl)-two (2,6-two fluoro-3-(1H-pyrroles-1-yl)-phenyl) titanium; 2-(dimethylamino)-2-[(4-aminomethyl phenyl) methyl]-1-[4-(4-morpholinyl) phenyl-1-butanone.
26. the reversible nano-imprint lithography glue of light for preparing according to claim 10 or 11 described crosslinking chemicals, it is characterized in that described photoacid generator comprises: the 2-nitrobenzyl ester of diazo salt, salt compounded of iodine, bromine salt, villaumite, sulfosalt, selenium salt, pyralium salt, thiapyran salt, pyridiniujm, halogenated compound, sulfonic acid; Imino group sulphonic acid ester, 1-oxo-2-diazo naphthoquinone-4-sulfonate derivatives, N-oxyimino sulphonic acid ester, three (mesyloxy) benzene derivative, two sulfonyl diazomethane class, sulfonyl carbonyl paraffinic, sulfonyl carbonyl diazomethane class or two sulphones.
27. preparation method according to the reversible nano-imprint lithography glue of arbitrary described light in the claim 9 to 26, it is characterized in that, by preparing the reversible nano-imprint lithography glue of light after light reversible cross-linking agent, light trigger and the optical polymerism compound.
28. application process according to the reversible nano-imprint lithography glue of arbitrary described light in the claim 9 to 26, it is characterized in that, by after being dissolved in described photoresist in the anhydrous chloroform and being diluted to mass concentration 5%, by 0.2 micron filtrator photoresist solution is carried out micro-filtration and be placed on and preserve under the lucifuge freezing environment or be used for the etching semiconductor silicon chip.
29. application process according to claim 28 is characterized in that, the reversible nano-imprint lithography glue of described light is in a liquid state at 15～30 ℃ of following monomer whoses and oligomer, in the scope of the viscosity under 25 ℃ below 20mPas.
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| CN103302939A (en) * | 2013-05-10 | 2013-09-18 | 西安建筑科技大学 | Self-cleaning structure and manufacturing method thereof |
| CN103302939B (en) * | 2013-05-10 | 2015-06-17 | 西安建筑科技大学 | Self-cleaning structure and manufacturing method thereof |
| CN105895805A (en) * | 2016-05-09 | 2016-08-24 | 浙江海洋大学 | Preparation method of active layer applicable to polymer solar cell |
| CN105895805B (en) * | 2016-05-09 | 2018-08-24 | 浙江海洋大学 | A kind of active layer preparation method suitable for polymer solar battery |
| CN106054523A (en) * | 2016-05-24 | 2016-10-26 | 北京化工大学 | Double response type degradable photoresist as well as preparation method and use method therefor |
| CN106054523B (en) * | 2016-05-24 | 2019-10-18 | 北京化工大学 | A kind of degradable photoresist of double-response type and preparation method thereof and application method |
| CN106527043A (en) * | 2016-11-22 | 2017-03-22 | 同济大学 | Method for fabricating large-area photonic crystal s scintillation body by imprinting technology |
| CN106527043B (en) * | 2016-11-22 | 2018-07-03 | 同济大学 | A kind of method that stamping technique prepares large area photon scintillation crystal |
| CN108864330A (en) * | 2017-05-12 | 2018-11-23 | 湖北固润科技股份有限公司 | Poly(4-hydroxystyrene) class oxetane resin, its synthesis and application |
| CN108864330B (en) * | 2017-05-12 | 2020-04-07 | 湖北固润科技股份有限公司 | Poly (p-hydroxystyrene) oxetane resin, and synthesis and application thereof |
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