CN115477865B - Ultraviolet light curing nano imprinting material, preparation method thereof and imprinting template - Google Patents
Ultraviolet light curing nano imprinting material, preparation method thereof and imprinting template Download PDFInfo
- Publication number
- CN115477865B CN115477865B CN202110601424.3A CN202110601424A CN115477865B CN 115477865 B CN115477865 B CN 115477865B CN 202110601424 A CN202110601424 A CN 202110601424A CN 115477865 B CN115477865 B CN 115477865B
- Authority
- CN
- China
- Prior art keywords
- ultraviolet light
- acrylate
- light curing
- catechol
- imprinting
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
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- 239000000463 material Substances 0.000 title claims abstract description 66
- 238000002360 preparation method Methods 0.000 title claims abstract description 11
- YCIMNLLNPGFGHC-UHFFFAOYSA-N catechol Chemical group OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 claims abstract description 52
- 239000000758 substrate Substances 0.000 claims abstract description 38
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims abstract description 25
- CFFZDZCDUFSOFZ-UHFFFAOYSA-N 3,4-Dihydroxy-phenylacetic acid Chemical compound OC(=O)CC1=CC=C(O)C(O)=C1 CFFZDZCDUFSOFZ-UHFFFAOYSA-N 0.000 claims description 30
- YQUVCSBJEUQKSH-UHFFFAOYSA-N 3,4-dihydroxybenzoic acid Chemical compound OC(=O)C1=CC=C(O)C(O)=C1 YQUVCSBJEUQKSH-UHFFFAOYSA-N 0.000 claims description 28
- 239000000178 monomer Substances 0.000 claims description 28
- ISAOCJYIOMOJEB-UHFFFAOYSA-N benzoin Chemical compound C=1C=CC=CC=1C(O)C(=O)C1=CC=CC=C1 ISAOCJYIOMOJEB-UHFFFAOYSA-N 0.000 claims description 26
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 25
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims description 22
- 239000011259 mixed solution Substances 0.000 claims description 20
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 claims description 16
- 150000001875 compounds Chemical class 0.000 claims description 16
- 239000010410 layer Substances 0.000 claims description 15
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 claims description 14
- -1 acrylic ester Chemical class 0.000 claims description 14
- 230000007704 transition Effects 0.000 claims description 14
- 244000028419 Styrax benzoin Species 0.000 claims description 13
- 235000000126 Styrax benzoin Nutrition 0.000 claims description 13
- 235000008411 Sumatra benzointree Nutrition 0.000 claims description 13
- 239000012790 adhesive layer Substances 0.000 claims description 13
- 229960002130 benzoin Drugs 0.000 claims description 13
- 235000019382 gum benzoic Nutrition 0.000 claims description 13
- OMIGHNLMNHATMP-UHFFFAOYSA-N 2-hydroxyethyl prop-2-enoate Chemical compound OCCOC(=O)C=C OMIGHNLMNHATMP-UHFFFAOYSA-N 0.000 claims description 12
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 12
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 12
- WOBHKFSMXKNTIM-UHFFFAOYSA-N Hydroxyethyl methacrylate Chemical compound CC(=C)C(=O)OCCO WOBHKFSMXKNTIM-UHFFFAOYSA-N 0.000 claims description 12
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 12
- 239000003085 diluting agent Substances 0.000 claims description 12
- 230000003213 activating effect Effects 0.000 claims description 11
- 239000003054 catalyst Substances 0.000 claims description 11
- 239000003153 chemical reaction reagent Substances 0.000 claims description 11
- 239000003431 cross linking reagent Substances 0.000 claims description 11
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 claims description 10
- 239000003999 initiator Substances 0.000 claims description 10
- 150000003254 radicals Chemical class 0.000 claims description 10
- 239000002904 solvent Substances 0.000 claims description 10
- 238000000034 method Methods 0.000 claims description 9
- 238000003756 stirring Methods 0.000 claims description 9
- ARXJGSRGQADJSQ-UHFFFAOYSA-N 1-methoxypropan-2-ol Chemical compound COCC(C)O ARXJGSRGQADJSQ-UHFFFAOYSA-N 0.000 claims description 8
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 claims description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 8
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 claims description 8
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 claims description 8
- 239000000706 filtrate Substances 0.000 claims description 7
- 238000002156 mixing Methods 0.000 claims description 7
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 claims description 5
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 claims description 5
- 239000012965 benzophenone Substances 0.000 claims description 5
- 229920002818 (Hydroxyethyl)methacrylate Polymers 0.000 claims description 4
- MSAHTMIQULFMRG-UHFFFAOYSA-N 1,2-diphenyl-2-propan-2-yloxyethanone Chemical compound C=1C=CC=CC=1C(OC(C)C)C(=O)C1=CC=CC=C1 MSAHTMIQULFMRG-UHFFFAOYSA-N 0.000 claims description 4
- YIKSHDNOAYSSPX-UHFFFAOYSA-N 1-propan-2-ylthioxanthen-9-one Chemical compound S1C2=CC=CC=C2C(=O)C2=C1C=CC=C2C(C)C YIKSHDNOAYSSPX-UHFFFAOYSA-N 0.000 claims description 4
- ZXDDPOHVAMWLBH-UHFFFAOYSA-N 2,4-Dihydroxybenzophenone Chemical compound OC1=CC(O)=CC=C1C(=O)C1=CC=CC=C1 ZXDDPOHVAMWLBH-UHFFFAOYSA-N 0.000 claims description 4
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 claims description 4
- DZZAHLOABNWIFA-UHFFFAOYSA-N 2-butoxy-1,2-diphenylethanone Chemical compound C=1C=CC=CC=1C(OCCCC)C(=O)C1=CC=CC=C1 DZZAHLOABNWIFA-UHFFFAOYSA-N 0.000 claims description 4
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 claims description 4
- GNSFRPWPOGYVLO-UHFFFAOYSA-N 3-hydroxypropyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCCO GNSFRPWPOGYVLO-UHFFFAOYSA-N 0.000 claims description 4
- QZPSOSOOLFHYRR-UHFFFAOYSA-N 3-hydroxypropyl prop-2-enoate Chemical compound OCCCOC(=O)C=C QZPSOSOOLFHYRR-UHFFFAOYSA-N 0.000 claims description 4
- MPIAGWXWVAHQBB-UHFFFAOYSA-N [3-prop-2-enoyloxy-2-[[3-prop-2-enoyloxy-2,2-bis(prop-2-enoyloxymethyl)propoxy]methyl]-2-(prop-2-enoyloxymethyl)propyl] prop-2-enoate Chemical compound C=CC(=O)OCC(COC(=O)C=C)(COC(=O)C=C)COCC(COC(=O)C=C)(COC(=O)C=C)COC(=O)C=C MPIAGWXWVAHQBB-UHFFFAOYSA-N 0.000 claims description 4
- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 claims description 4
- 239000002244 precipitate Substances 0.000 claims description 4
- LLHKCFNBLRBOGN-UHFFFAOYSA-N propylene glycol methyl ether acetate Chemical compound COCC(C)OC(C)=O LLHKCFNBLRBOGN-UHFFFAOYSA-N 0.000 claims description 4
- MYWOJODOMFBVCB-UHFFFAOYSA-N 1,2,6-trimethylphenanthrene Chemical compound CC1=CC=C2C3=CC(C)=CC=C3C=CC2=C1C MYWOJODOMFBVCB-UHFFFAOYSA-N 0.000 claims description 3
- GTELLNMUWNJXMQ-UHFFFAOYSA-N 2-ethyl-2-(hydroxymethyl)propane-1,3-diol;prop-2-enoic acid Chemical class OC(=O)C=C.OC(=O)C=C.OC(=O)C=C.CCC(CO)(CO)CO GTELLNMUWNJXMQ-UHFFFAOYSA-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
- DAKWPKUUDNSNPN-UHFFFAOYSA-N Trimethylolpropane triacrylate Chemical compound C=CC(=O)OCC(CC)(COC(=O)C=C)COC(=O)C=C DAKWPKUUDNSNPN-UHFFFAOYSA-N 0.000 claims description 3
- HVVWZTWDBSEWIH-UHFFFAOYSA-N [2-(hydroxymethyl)-3-prop-2-enoyloxy-2-(prop-2-enoyloxymethyl)propyl] prop-2-enoate Chemical compound C=CC(=O)OCC(CO)(COC(=O)C=C)COC(=O)C=C HVVWZTWDBSEWIH-UHFFFAOYSA-N 0.000 claims description 3
- 239000007864 aqueous solution Substances 0.000 claims description 3
- 238000001035 drying Methods 0.000 claims description 3
- IFDFMWBBLAUYIW-UHFFFAOYSA-N ethane-1,2-diol;ethyl acetate Chemical compound OCCO.CCOC(C)=O IFDFMWBBLAUYIW-UHFFFAOYSA-N 0.000 claims description 3
- BHXIWUJLHYHGSJ-UHFFFAOYSA-N ethyl 3-ethoxypropanoate Chemical compound CCOCCC(=O)OCC BHXIWUJLHYHGSJ-UHFFFAOYSA-N 0.000 claims description 3
- 238000001914 filtration Methods 0.000 claims description 3
- 150000002576 ketones Chemical class 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
- PNXMTCDJUBJHQJ-UHFFFAOYSA-N propyl prop-2-enoate Chemical compound CCCOC(=O)C=C PNXMTCDJUBJHQJ-UHFFFAOYSA-N 0.000 claims description 3
- 239000002994 raw material Substances 0.000 claims description 3
- 238000005406 washing Methods 0.000 claims description 3
- YRHRIQCWCFGUEQ-UHFFFAOYSA-N thioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3SC2=C1 YRHRIQCWCFGUEQ-UHFFFAOYSA-N 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 abstract description 8
- VYFYYTLLBUKUHU-UHFFFAOYSA-N dopamine Chemical compound NCCC1=CC=C(O)C(O)=C1 VYFYYTLLBUKUHU-UHFFFAOYSA-N 0.000 description 20
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 15
- 229960003638 dopamine Drugs 0.000 description 10
- 239000000377 silicon dioxide Substances 0.000 description 7
- 235000012239 silicon dioxide Nutrition 0.000 description 7
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 6
- 229910052739 hydrogen Inorganic materials 0.000 description 6
- 239000001257 hydrogen Substances 0.000 description 6
- 229910052710 silicon Inorganic materials 0.000 description 6
- 239000010703 silicon Substances 0.000 description 6
- 238000005886 esterification reaction Methods 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- WTDRDQBEARUVNC-LURJTMIESA-N L-DOPA Chemical compound OC(=O)[C@@H](N)CC1=CC=C(O)C(O)=C1 WTDRDQBEARUVNC-LURJTMIESA-N 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 230000008569 process Effects 0.000 description 3
- VVBLNCFGVYUYGU-UHFFFAOYSA-N 4,4'-Bis(dimethylamino)benzophenone Chemical compound C1=CC(N(C)C)=CC=C1C(=O)C1=CC=C(N(C)C)C=C1 VVBLNCFGVYUYGU-UHFFFAOYSA-N 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- 241000237536 Mytilus edulis Species 0.000 description 2
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 2
- 125000005396 acrylic acid ester group Chemical group 0.000 description 2
- 239000000853 adhesive Substances 0.000 description 2
- 230000001070 adhesive effect Effects 0.000 description 2
- 238000000576 coating method Methods 0.000 description 2
- 239000007822 coupling agent Substances 0.000 description 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
- 239000010408 film Substances 0.000 description 2
- 229910010272 inorganic material Inorganic materials 0.000 description 2
- 239000011147 inorganic material Substances 0.000 description 2
- 235000020638 mussel Nutrition 0.000 description 2
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 2
- 150000003141 primary amines Chemical group 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- DTGKSKDOIYIVQL-WEDXCCLWSA-N (+)-borneol Chemical group C1C[C@@]2(C)[C@@H](O)C[C@@H]1C2(C)C DTGKSKDOIYIVQL-WEDXCCLWSA-N 0.000 description 1
- SFLSHLFXELFNJZ-QMMMGPOBSA-N (-)-norepinephrine Chemical compound NC[C@H](O)C1=CC=C(O)C(O)=C1 SFLSHLFXELFNJZ-QMMMGPOBSA-N 0.000 description 1
- OTKCEEWUXHVZQI-UHFFFAOYSA-N 1,2-diphenylethanone Chemical compound C=1C=CC=CC=1C(=O)CC1=CC=CC=C1 OTKCEEWUXHVZQI-UHFFFAOYSA-N 0.000 description 1
- 239000012956 1-hydroxycyclohexylphenyl-ketone Substances 0.000 description 1
- PIZHFBODNLEQBL-UHFFFAOYSA-N 2,2-diethoxy-1-phenylethanone Chemical compound CCOC(OCC)C(=O)C1=CC=CC=C1 PIZHFBODNLEQBL-UHFFFAOYSA-N 0.000 description 1
- TXBCBTDQIULDIA-UHFFFAOYSA-N 2-[[3-hydroxy-2,2-bis(hydroxymethyl)propoxy]methyl]-2-(hydroxymethyl)propane-1,3-diol Chemical compound OCC(CO)(CO)COCC(CO)(CO)CO TXBCBTDQIULDIA-UHFFFAOYSA-N 0.000 description 1
- MCDBEBOBROAQSH-UHFFFAOYSA-N 3-[dimethoxy(methyl)silyl]propyl prop-2-enoate Chemical compound CO[Si](C)(OC)CCCOC(=O)C=C MCDBEBOBROAQSH-UHFFFAOYSA-N 0.000 description 1
- XDQWJFXZTAWJST-UHFFFAOYSA-N 3-triethoxysilylpropyl prop-2-enoate Chemical compound CCO[Si](OCC)(OCC)CCCOC(=O)C=C XDQWJFXZTAWJST-UHFFFAOYSA-N 0.000 description 1
- LCAINUZZHIZKKS-UHFFFAOYSA-N 5-Hydroxydopamine Chemical compound NCCC1=CC(O)=C(O)C(O)=C1 LCAINUZZHIZKKS-UHFFFAOYSA-N 0.000 description 1
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical group NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 1
- GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 description 1
- WTDRDQBEARUVNC-UHFFFAOYSA-N L-Dopa Natural products OC(=O)C(N)CC1=CC=C(O)C(O)=C1 WTDRDQBEARUVNC-UHFFFAOYSA-N 0.000 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 1
- 238000005741 Steglich esterification reaction Methods 0.000 description 1
- KNSXNCFKSZZHEA-UHFFFAOYSA-N [3-prop-2-enoyloxy-2,2-bis(prop-2-enoyloxymethyl)propyl] prop-2-enoate Chemical class C=CC(=O)OCC(COC(=O)C=C)(COC(=O)C=C)COC(=O)C=C KNSXNCFKSZZHEA-UHFFFAOYSA-N 0.000 description 1
- RMKZLFMHXZAGTM-UHFFFAOYSA-N [dimethoxy(propyl)silyl]oxymethyl prop-2-enoate Chemical compound CCC[Si](OC)(OC)OCOC(=O)C=C RMKZLFMHXZAGTM-UHFFFAOYSA-N 0.000 description 1
- GUCYFKSBFREPBC-UHFFFAOYSA-N [phenyl-(2,4,6-trimethylbenzoyl)phosphoryl]-(2,4,6-trimethylphenyl)methanone Chemical compound CC1=CC(C)=CC(C)=C1C(=O)P(=O)(C=1C=CC=CC=1)C(=O)C1=C(C)C=C(C)C=C1C GUCYFKSBFREPBC-UHFFFAOYSA-N 0.000 description 1
- KSRGADMGIRTXAF-UHFFFAOYSA-N a-Methyldopamine Chemical compound CC(N)CC1=CC=C(O)C(O)=C1 KSRGADMGIRTXAF-UHFFFAOYSA-N 0.000 description 1
- HFBMWMNUJJDEQZ-UHFFFAOYSA-N acryloyl chloride Chemical compound ClC(=O)C=C HFBMWMNUJJDEQZ-UHFFFAOYSA-N 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 150000004996 alkyl benzenes Chemical class 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- WURBFLDFSFBTLW-UHFFFAOYSA-N benzil Chemical compound C=1C=CC=CC=1C(=O)C(=O)C1=CC=CC=C1 WURBFLDFSFBTLW-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- MQDJYUACMFCOFT-UHFFFAOYSA-N bis[2-(1-hydroxycyclohexyl)phenyl]methanone Chemical compound C=1C=CC=C(C(=O)C=2C(=CC=CC=2)C2(O)CCCCC2)C=1C1(O)CCCCC1 MQDJYUACMFCOFT-UHFFFAOYSA-N 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- QXWYKJLNLSIPIN-SFYZADRCSA-N droxidopa Chemical compound OC(=O)[C@H](N)[C@@H](O)C1=CC=C(O)C(O)=C1 QXWYKJLNLSIPIN-SFYZADRCSA-N 0.000 description 1
- 229960001104 droxidopa Drugs 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 230000002708 enhancing effect Effects 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 239000002086 nanomaterial Substances 0.000 description 1
- 229960002748 norepinephrine Drugs 0.000 description 1
- SFLSHLFXELFNJZ-UHFFFAOYSA-N norepinephrine Natural products NCC(O)C1=CC=C(O)C(O)=C1 SFLSHLFXELFNJZ-UHFFFAOYSA-N 0.000 description 1
- 239000011368 organic material Substances 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 229910001392 phosphorus oxide Inorganic materials 0.000 description 1
- ARJOQCYCJMAIFR-UHFFFAOYSA-N prop-2-enoyl prop-2-enoate Chemical compound C=CC(=O)OC(=O)C=C ARJOQCYCJMAIFR-UHFFFAOYSA-N 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D4/00—Coating compositions, e.g. paints, varnishes or lacquers, based on organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond ; Coating compositions, based on monomers of macromolecular compounds of groups C09D183/00 - C09D183/16
- C09D4/06—Organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond in combination with a macromolecular compound other than an unsaturated polymer of groups C09D159/00 - C09D187/00
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F120/00—Homopolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride, ester, amide, imide or nitrile thereof
- C08F120/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
- C08F120/10—Esters
- C08F120/26—Esters containing oxygen in addition to the carboxy oxygen
- C08F120/30—Esters containing oxygen in addition to the carboxy oxygen containing aromatic rings in the alcohol moiety
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/0002—Lithographic processes using patterning methods other than those involving the exposure to radiation, e.g. by stamping
Abstract
The invention provides an ultraviolet light curing nano imprinting material, a preparation method thereof and an imprinting template, belongs to the technical field of micro-nano manufacturing, and solves the problem of low adhesion between the ultraviolet light curing nano imprinting material and a substrate. The ultraviolet light curing nano-imprinting material comprises an acrylic prepolymer, wherein the acrylic prepolymer contains catechol groups.
Description
Technical Field
The disclosure belongs to the technical field of micro-nano manufacturing, and particularly relates to an ultraviolet light curing nano imprinting material, a preparation method thereof and an imprinting template.
Background
In the nanoimprint process, a large number of nano structures are generally arranged on an imprint template, and the surface area of the imprint template is far larger than that of a substrate, and the substrate is mostly a smooth surface, so that the imprint adhesive material is easily peeled off by the imprint template during demolding, and therefore, how to ensure good adhesion between the imprint adhesive material and the substrate becomes a technical problem to be solved.
Disclosure of Invention
The disclosure aims to at least solve one of the technical problems in the prior art and provides an ultraviolet light curing nano imprinting material, a preparation method thereof and an imprinting template.
In a first aspect, embodiments of the present disclosure provide an ultraviolet light curable nanoimprint material, including an acrylate prepolymer, where the acrylate prepolymer contains catechol groups.
Optionally, the raw materials for preparing the acrylic prepolymer comprise: an acrylic monomer containing hydroxyl, a catalyst, a carboxyl activating reagent and a compound containing catechol groups.
Optionally, the acrylic monomer comprises any one or more of hydroxyethyl acrylate, hydroxyethyl methacrylate, hydroxypropyl acrylate and hydroxypropyl methacrylate; the catalyst comprises 4-dimethylaminopyridine; the carboxyl activating reagent comprises N, N' -dicyclohexylcarbodiimide; the catechol group-containing compound includes 3, 4-dihydroxybenzoic acid or 3, 4-dihydroxyphenylacetic acid or more of the catechol groups.
Optionally, the ultraviolet light curing nano-imprint material further comprises a solvent, a reactive diluent, a cross-linking agent and a free radical initiator.
Optionally, the mass of the acrylic prepolymer accounts for 5-50% of the mass of the ultraviolet light curing nano imprinting material.
Optionally, when the ultraviolet light curing nano imprinting material is adhered to the substrate, the adhesion strength of the ultraviolet light curing nano imprinting material and the substrate ranges from 1 Mpa to 5Mpa.
Optionally, the reactive diluent comprises one or more of cyclohexanone, anisole, ethyl acetate, ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, methyl acrylate, ethyl acrylate, propyl acrylate.
Optionally, the cross-linking agent comprises one or more of pentaerythritol triacrylate, trimethylolpropane triacrylate, ethoxylated trimethylolpropane triacrylate, pentaerythritol tetraacrylate, dipentaerythritol hexaacrylate.
Optionally, the free radical initiator comprises one or more of benzoin, benzoin dimethyl ether, benzoin diethyl ether, benzoin isopropyl ether, benzoin butyl ether, benzophenone, 2, 4-dihydroxybenzophenone, mi ketone, thiopropoxy thioxanthone, isopropyl thioxanthone.
Optionally, the solvent comprises one or more of propylene glycol methyl ether acetate, ethyl 3-ethoxypropionate, propylene glycol methyl ether, and ethylene glycol ethyl acetate.
In a second aspect, an embodiment of the present disclosure provides a method for preparing an ultraviolet light-curable nanoimprint material, including:
mixing a catechol group-containing compound, a hydroxyl group-containing acrylic monomer and a catalyst to obtain a first mixed solution, and stirring the first mixed solution in an ice bath at a first temperature;
adding a carboxyl activating reagent into the first mixed solution to obtain a second mixed solution; stirring the second mixed solution at a second temperature, and filtering the precipitate in the second mixed solution to obtain filtrate; the second temperature is higher than the first temperature;
washing the filtrate with hydrochloric acid and saturated sodium bicarbonate aqueous solution respectively, and then drying and distilling under reduced pressure to obtain acrylic ester prepolymer;
and mixing the obtained acrylic prepolymer with a solvent, a reactive diluent, a cross-linking agent and a free radical initiator to obtain the ultraviolet light curing nanoimprint material.
Optionally, the first temperature is between-5 ℃ and 5 ℃, and the second temperature is between 10 ℃ and 40 ℃; the stirring time of the second mixed solution at the second temperature is 2.5-3.5 hours.
In a third aspect, an embodiment of the present disclosure provides an imprint template, including a substrate, a middle transition adhesion layer and an ultraviolet light-curable adhesive layer, where the middle transition adhesion layer is disposed on one side of the substrate, and the ultraviolet light-curable adhesive layer is disposed on a side of the middle transition adhesion layer facing away from the substrate, where a material of the middle transition adhesion layer includes an ultraviolet light-curable nanoimprint material according to any one of claims 1 to 10.
Drawings
Fig. 1 is a schematic flow chart of a method for preparing an ultraviolet light cured nano imprinting material according to an embodiment of the disclosure;
fig. 2 is a schematic structural diagram of an imprint template according to an embodiment of the present disclosure.
Detailed Description
In order that those skilled in the art will better understand the technical solutions of the present disclosure, the present disclosure will be described in further detail with reference to the accompanying drawings and detailed description.
Unless defined otherwise, technical or scientific terms used in this disclosure should be given the ordinary meaning as understood by one of ordinary skill in the art to which this disclosure belongs. The terms "first," "second," and the like, as used in this disclosure, do not denote any order, quantity, or importance, but rather are used to distinguish one element from another. Likewise, the terms "a," "an," or "the" and similar terms do not denote a limitation of quantity, but rather denote the presence of at least one. The word "comprising" or "comprises", and the like, means that elements or items preceding the word are included in the element or item listed after the word and equivalents thereof, but does not exclude other elements or items. The terms "connected" or "connected," and the like, are not limited to physical or mechanical connections, but may include electrical connections, whether direct or indirect. "upper", "lower", "left", "right", etc. are used merely to indicate relative positional relationships, which may also be changed when the absolute position of the object to be described is changed.
The inventors have found that marine organisms such as mussels can adhere themselves to almost any material surface. Further research shows that marine mussels contain a large amount of dopa (3, 4-dihydroxyphenylalanine), the catechol group on dopa plays a main role in the adhesion process, and two adjacent phenolic hydroxyl groups can form strong interaction with the surfaces of other materials, so that the effect of enhancing the adhesion is achieved.
In the prior art, the preparation of the photo-curable monomer containing catechol group mainly utilizes dopamine or dopamine-like molecules, the catechol group is introduced to acrylate or methacrylate monomers, the molecular structure of the dopamine or dopamine-like molecules not only has the catechol group, but also has a reactive primary amine group, and the (meth) acrylamide monomer with the catechol group can be prepared by utilizing the reaction of (meth) acryloyl chloride or (meth) acrylic anhydride and the primary amine. The dopamine or dopamine-like molecules used to prepare such monomers may be dopamine, methyldopamine, droxidopa, 5-hydroxydopamine or norepinephrine, etc., but these molecules are commonly characterized by being expensive and unsuitable for mass production.
In the nanoimprint technology, an ultraviolet light-curable nanoimprint material is generally coated on a substrate, where the substrate may be an inorganic material or an organic material, and in this embodiment, the substrate is an inorganic material, for example, the substrate may be silicon dioxide.
In a first aspect, embodiments of the present disclosure provide an ultraviolet light curable nanoimprint material, which includes an acrylate prepolymer, wherein the acrylate prepolymer contains catechol groups.
In the embodiment, the acrylate prepolymer containing the catechol group is added into the ultraviolet light curing nano imprinting material, so that a hydrogen bond is formed between the hydroxyl group in the catechol group and the hydroxyl group in the silicon dioxide substrate, the adhesion between the ultraviolet light curing nano imprinting material and the silicon substrate is improved, and the ultraviolet light curing nano imprinting material is prevented from being stripped by the imprinting template during demolding.
Optionally, the raw materials for preparing the acrylic prepolymer comprise: an acrylic monomer containing hydroxyl, a catalyst, a carboxyl activating reagent and a compound containing catechol groups.
Specifically, the acrylic monomer comprises any one or more of hydroxyethyl acrylate, hydroxyethyl methacrylate, hydroxypropyl acrylate and hydroxypropyl methacrylate. The catalyst comprises 4-dimethylaminopyridine. The carboxyl activating reagent includes N, N' -dicyclohexylcarbodiimide. The catechol group-containing compound includes 3, 4-dihydroxybenzoic acid or 3, 4-dihydroxyphenylacetic acid or more of the catechol groups.
In this embodiment, 3, 4-dihydroxybenzoic acid and 3, 4-dihydroxyphenylacetic acid with catechol groups are adopted to replace dopamine molecules, esterification reaction of carboxyl groups on molecules and hydroxyl groups of hydroxyethyl (meth) acrylate is adopted, a Steglich esterification method with mild reaction conditions is adopted, N' -Dicyclohexylcarbodiimide (DCC) is adopted as a carboxyl activating reagent, 4-Dimethylaminopyridine (DMAP) is adopted as a catalyst, and an acrylic monomer with catechol groups is prepared, so that hydroxyl groups in the catechol groups and hydroxyl groups in a silicon dioxide substrate form hydrogen bonds, adhesion between an ultraviolet light curing nanoimprint material and a silicon substrate is improved, the ultraviolet light curing nanoimprint material is prevented from being stripped by an imprint template, and meanwhile, a compound containing catechol groups is adopted to replace dopamine molecules, so that the production cost of the ultraviolet light curing nanoimprint material is reduced.
Optionally, the ultraviolet light curing nanoimprint material comprises a solvent, a reactive diluent, a cross-linking agent and a free radical initiator in addition to the acrylate prepolymer containing catechol groups.
Further, the solvent comprises one or more of propylene glycol methyl ether acetate, ethyl 3-ethoxypropionate, propylene glycol methyl ether (PM) and ethylene glycol ethyl acetate.
Further, the reactive diluent comprises one or more of cyclohexanone, anisole, ethyl acetate, ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, methyl acrylate, ethyl acrylate and propyl acrylate.
In particular, the reactive diluent is used for reducing the viscosity of the ultraviolet light curing nano-imprinting material to be suitable for a coating process, and the diluent can be a non-reactive solvent including, but not limited to, cyclohexanone, anisole, ethyl acetate, ethylene glycol monomethyl ether, ethylene glycol monoethyl ether and ethylene glycol monoethyl ester; propylene glycol methyl ether acetate. The diluent may also be a reactive monomer including, but not limited to, methyl (meth) acrylate, ethyl (meth) acrylate, propyl (meth) acrylate, butyl (meth) acrylate, terbutyl (meth) acrylate, isobornyl (meth) acrylate, and the like.
Further, the cross-linking agent comprises one or more of pentaerythritol triacrylate, trimethylolpropane triacrylate, ethoxylated trimethylolpropane triacrylate, pentaerythritol tetraacrylate, dipentaerythritol hexaacrylate.
Specifically, the crosslinking agent is used for improving the mechanical strength of the ultraviolet light curing nano imprinting material, and the crosslinking agent comprises pentaerythritol tri (methyl) acrylate, trimethylolpropane tri (methyl) acrylate, ethoxylated trimethylolpropane tri (methyl) acrylate, pentaerythritol tetra (methyl) acrylate, dipentaerythritol hexa-propyl (methyl) acrylate and the like.
Optionally, the free radical initiator comprises one or more of benzoin, benzoin dimethyl ether, benzoin diethyl ether, benzoin isopropyl ether, benzoin butyl ether, benzophenone, 2, 4-dihydroxybenzophenone, mi ketone, thiopropylthioxanthone, isopropylthioxanthone.
In particular, free radical initiators include, but are not limited to benzoin and derivatives (benzoin, benzoin dimethyl ether, benzoin diethyl ether, benzoin isopropyl ether, benzoin butyl ether); benzil (diphenylethanone, α -dimethoxy- α -phenylacetophenone); alkylbenzene (α, α -diethoxyacetophenone, α -hydroxyalkylbenzophenone, α -aminoalkyl ketone); acyl phosphorus oxide (aroylphosphine oxide, bisbenzoylphenylphosphine oxide); benzophenone (benzophenone, 2, 4-dihydroxybenzophenone, michler's ketone); thioxanthones (thiopropyloxythioxanthones, isopropylthioxanthones) and the like.
Optionally, the uv curable nanoimprint material may further include other additives such as leveling agents that help the nanoimprint resist form a thin film of uniform thickness, coupling agents that enhance the adhesion of the nanoimprint resist to the substrate, and the like. Among them, the coupling agent includes, but is not limited to, (meth) acryloxypropyl triethoxysilane, (meth) acryloxypropyl methyl dimethoxysilane, (meth) acryloxypropyl trimethoxysilane, and the like.
Optionally, the mass of the acrylic prepolymer accounts for 5-50% of the mass of the ultraviolet light curing nano imprinting material.
Optionally, when the ultraviolet light curing nano-imprinting material is adhered to the substrate, the adhesion strength of the ultraviolet light curing nano-imprinting material and the substrate ranges from 1 Mpa to 5Mpa.
In a second aspect, an embodiment of the present disclosure provides a method for preparing an ultraviolet light-cured nanoimprint material, as shown in fig. 1, where the method specifically includes:
s101, mixing a catechol group-containing compound, a hydroxyl group-containing acrylic monomer and a catalyst to obtain a first mixed solution, and stirring the first mixed solution in an ice bath at a first temperature.
S102, adding a carboxyl activating reagent into the first mixed solution to obtain a second mixed solution; stirring the second mixed solution at a second temperature, and filtering the precipitate in the second mixed solution to obtain filtrate; the second temperature is higher than the first temperature.
And S103, respectively washing the filtrate by using hydrochloric acid and saturated sodium bicarbonate aqueous solution, and then drying and distilling under reduced pressure to obtain the acrylic prepolymer.
And S104, mixing the obtained acrylic prepolymer with a solvent, a reactive diluent, a cross-linking agent and a free radical initiator to obtain the ultraviolet light curing nanoimprint material.
Wherein the first temperature is between-5 ℃ and 5 ℃, preferably the first temperature is 0 ℃. The second temperature is between 10 ℃ and 40 ℃, preferably the second temperature is 25 ℃. It will be appreciated that the first temperature and the second temperature may also be selected as desired by those skilled in the art and are further exemplified herein. The preparation of the ultraviolet light curing nanoimprint material is described below by taking a catechol group-containing compound including 3, 4-dihydroxybenzoic acid and a hydroxyl group-containing acrylate monomer including 2-hydroxyethyl acrylate as an example, and the specific synthesis process is as follows: 200 ml of dried methylene chloride, 15.4 g of 3, 4-dihydroxybenzoic acid (0.10 mol), 46.4 g of 2-hydroxyethyl acrylate (0.40 mol), 1 g of 4-dimethylaminopyridine DMAP (0.08 mol) were added to a 500 ml single-necked flask, stirred in an ice bath at 0℃and 22.80 g of N, N' -dicyclohexylcarbodiimide DCC (0.11 mol) were gradually added, then the ice bath was removed, stirring was continued at ordinary temperature for 3 hours, and the precipitate was filtered. The filtrate was washed twice with 0.5N hydrochloric acid and saturated aqueous sodium bicarbonate solution, respectively, and then dried over magnesium sulfate. And (3) removing dichloromethane and 2-hydroxyethyl acrylate by reduced pressure distillation to obtain catechol hydroxyethyl benzoate acrylate monomer which is colorless and transparent and is a viscous liquid with aromatic smell. Finally, mixing catechol hydroxyethyl benzoate acrylate (30%), ethoxylated pentaerythritol tetraacrylate (45%), dipentaerythritol hexaacrylate (20%), 1-hydroxycyclohexyl phenyl ketone (4%), phenyl bis (2, 4, 6-trimethylbenzoyl) phosphine oxide (1%) to obtain the ultraviolet light curing nano imprinting material.
The chemical formula of the esterification reaction of 3, 4-dihydroxybenzoic acid and 2-hydroxyethyl acrylate is as follows:
in the embodiment, the catechol benzoic acid hydroxyethyl acrylate monomer prepared from 3, 4-dihydroxybenzoic acid and 2-hydroxyethyl acrylate contains catechol groups, so that hydroxyl groups in the catechol groups can form hydrogen bonds with hydroxyl groups in a silicon dioxide substrate, the adhesion between the ultraviolet light curing nano imprinting material and the silicon substrate is improved, the ultraviolet light curing nano imprinting material is prevented from being stripped by an imprinting template during demolding, and meanwhile, 3, 4-dihydroxybenzoic acid containing the catechol groups is adopted to replace dopamine molecules, so that the preparation can be performed in a large scale, and the production cost is reduced.
Alternatively, catechol phenylacetate hydroxyethyl acrylate monomers can also be prepared using compounds containing catechol groups, including 3, 4-dihydroxyphenylacetic acid, hydroxyl-containing acrylate monomers, including 2-hydroxyethyl acrylate. Wherein, the chemical reaction formula of the 3, 4-dihydroxyphenylacetic acid and the 2-hydroxyethyl acrylate is as follows:
the content of 3, 4-dihydroxyphenylacetic acid and 2-hydroxyethyl acrylate in the composition may be selected as desired, and is not particularly limited herein.
In the embodiment, the catechol group is contained in the prepared catechol phenylacetate hydroxyethyl acrylate monomer, so that a hydroxyl group in the catechol group can form a hydrogen bond with a hydroxyl group in a silicon dioxide substrate, the adhesion between the ultraviolet light curing nano imprinting material and the silicon substrate is improved, the ultraviolet light curing nano imprinting material is prevented from being stripped by an imprinting template during demolding, and the 3, 4-dihydroxyphenylacetic acid containing the catechol group is adopted to replace dopamine molecules, so that the catechol type nano imprinting material can be prepared in a large quantity, and the production cost is reduced.
Alternatively, catechol benzoic acid hydroxyethyl methacrylate monomers can also be prepared using compounds containing catechol groups including 3, 4-dihydroxybenzoic acid, and hydroxyl group containing acrylate monomers including 2-hydroxyethyl methacrylate. Wherein, the chemical formula of the esterification reaction of 3, 4-dihydroxybenzoic acid and 2-hydroxyethyl methacrylate is as follows:
the content of 3, 4-dihydroxybenzoic acid and 2-hydroxyethyl methacrylate may be selected as desired, and is not particularly limited herein.
In the embodiment, since the catechol benzoic acid hydroxyethyl methacrylate monomer is prepared by 3, 4-dihydroxybenzoic acid and 2-hydroxyethyl methacrylate and contains catechol groups, hydroxyl groups in the catechol groups can form hydrogen bonds with hydroxyl groups in a silicon dioxide substrate, the adhesion between the ultraviolet light curing nano imprinting material and the silicon substrate is improved, the ultraviolet light curing nano imprinting material is prevented from being stripped by an imprinting template during demolding, and meanwhile, 3, 4-dihydroxyphenylacetic acid containing the catechol groups is adopted to replace dopamine molecules, so that the preparation can be performed in a large scale, and the production cost is reduced.
Alternatively, catechol phenylacetate hydroxyethyl methacrylate monomers can also be prepared using compounds containing catechol groups including 3, 4-dihydroxyphenylacetic acid, hydroxyl-containing acrylate monomers including 2-hydroxyethyl methacrylate. Wherein, the chemical formula of the esterification reaction of 3, 4-dihydroxyphenylacetic acid and 2-hydroxyethyl methacrylate is as follows:
the content of 3, 4-dihydroxyphenylacetic acid and 2-hydroxyethyl methacrylate may be selected as desired, and is not particularly limited herein.
In the embodiment, since the catechol phenylacetate hydroxyethyl methacrylate monomer prepared from 3, 4-dihydroxyphenylacetic acid and 2-hydroxyethyl methacrylate contains catechol groups, hydroxyl groups in the catechol groups can form hydrogen bonds with hydroxyl groups in a silicon dioxide substrate, the adhesion between the ultraviolet light curing nano imprinting material and the silicon substrate is improved, the ultraviolet light curing nano imprinting material is prevented from being stripped by an imprinting template during demolding, and meanwhile, the 3, 4-dihydroxyphenylacetic acid containing the catechol groups is adopted to replace dopamine molecules, so that the preparation can be performed in a large scale, and the production cost is reduced.
It should be noted that other catechol group-containing compounds and hydroxyl group-containing acrylate monomers may be used to prepare the acrylate prepolymer, and are not illustrated herein.
In a third aspect, as shown in fig. 2, an embodiment of the present disclosure provides an imprint template including a substrate 11, an intermediate transitional adhesive layer 12, and an ultraviolet light curable adhesive layer 13.
Specifically, the intermediate transition adhesion layer 12 is disposed on one side of the substrate 11, and the uv-curable adhesive layer 13 is disposed on one side of the intermediate transition adhesion layer 12 facing away from the substrate 11, where the intermediate transition adhesion layer 12 is formed by coating a uv-curable nanoimprint material, and the uv-curable nanoimprint material includes an acrylate prepolymer containing catechol groups.
When the imprinting template is applied, before the ultraviolet light curing adhesive layer 13 is coated on the substrate 11, a layer of acrylic prepolymer containing catechol groups is coated and cured, and then the ultraviolet light curing adhesive layer 13 is formed on the cured acrylic prepolymer. In the imprinting template provided by the embodiment, catechol groups in the intermediate transition adhesion layer 12 play a role in adhering to the substrate 11, and in addition, acrylic acid ester in the intermediate transition adhesion layer 12 can react with acrylic acid ester groups in the upper ultraviolet light curing adhesive layer 13 to further enhance the adhesion between the ultraviolet light curing adhesive layer 13 and the intermediate transition adhesion layer 12.
Alternatively, the film thickness of the intermediate transitional adhesive layer 12 may be set as appropriate. Preferably, the intermediate transitional adhesive layer 12 has a film thickness of 20 nanometers to 1 micrometer.
It is to be understood that the above embodiments are merely exemplary embodiments employed to illustrate the principles of the present disclosure, however, the present disclosure is not limited thereto. Various modifications and improvements may be made by those skilled in the art without departing from the spirit and substance of the disclosure, and are also considered to be within the scope of the disclosure.
Claims (11)
1. The ultraviolet light curing nano imprinting material is characterized by comprising an acrylic prepolymer, wherein the acrylic prepolymer contains catechol groups; the raw materials for preparing the acrylic prepolymer comprise: a hydroxyl group-containing acrylate monomer, a catalyst, a carboxyl activating reagent, and a catechol group-containing compound; wherein the acrylic monomer comprises any one or more of hydroxyethyl acrylate, hydroxyethyl methacrylate, hydroxypropyl acrylate and hydroxypropyl methacrylate;
the catalyst comprises 4-dimethylaminopyridine;
the carboxyl activating reagent comprises N, N' -dicyclohexylcarbodiimide;
the catechol group-containing compound includes 3, 4-dihydroxybenzoic acid or 3, 4-dihydroxyphenylacetic acid or more having a catechol group.
2. The uv curable nanoimprint material of claim 1, further comprising a solvent, a reactive diluent, a cross-linking agent, and a free radical initiator.
3. The ultraviolet light-curing nano-imprinting material according to claim 1, wherein the mass of the acrylic prepolymer accounts for 5% -50% of the mass of the ultraviolet light-curing nano-imprinting material.
4. The uv-curable nanoimprint material of claim 1, wherein when the uv-curable nanoimprint material is adhered to a substrate, an adhesion strength of the uv-curable nanoimprint material to the substrate ranges from 1 mpa to 5mpa.
5. The uv curable nanoimprint material of claim 2, wherein the reactive diluent comprises one or more of cyclohexanone, anisole, ethyl acetate, ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, methyl acrylate, ethyl acrylate, propyl acrylate.
6. The uv curable nanoimprint material of claim 2, wherein the cross-linking agent comprises one or more of pentaerythritol triacrylate, trimethylolpropane triacrylate, ethoxylated trimethylolpropane triacrylate, pentaerythritol tetraacrylate, dipentaerythritol hexaacrylate.
7. The uv curable nanoimprint material of claim 2, wherein the free radical initiator comprises one or more of benzoin, benzoin dimethyl ether, benzoin diethyl ether, benzoin isopropyl ether, benzoin butyl ether, benzophenone, 2, 4-dihydroxybenzophenone, mi ketone, thiopropoxy thioxanthone, isopropyl thioxanthone.
8. The uv curable nanoimprint material of claim 2, wherein the solvent comprises one or more of propylene glycol methyl ether acetate, ethyl 3-ethoxypropionate, propylene glycol methyl ether, and ethylene glycol ethyl acetate.
9. The preparation method of the ultraviolet light curing nano imprinting material is characterized by comprising the following steps of:
mixing a catechol group-containing compound, a hydroxyl group-containing acrylic monomer and a catalyst to obtain a first mixed solution, and stirring the first mixed solution at a first temperature in an ice bath;
adding a carboxyl activating reagent into the first mixed solution to obtain a second mixed solution; stirring the second mixed solution at a second temperature, and filtering the precipitate in the second mixed solution to obtain filtrate; the second temperature is higher than the first temperature;
washing the filtrate with hydrochloric acid and saturated sodium bicarbonate aqueous solution respectively, and then drying and distilling under reduced pressure to obtain acrylic ester prepolymer;
mixing the obtained acrylic prepolymer with a solvent, a reactive diluent, a cross-linking agent and a free radical initiator to obtain an ultraviolet light curing nanoimprint material; wherein,
the acrylic ester monomer comprises any one or more of hydroxyethyl acrylate, hydroxyethyl methacrylate, hydroxypropyl acrylate and hydroxypropyl methacrylate;
the catalyst comprises 4-dimethylaminopyridine;
the carboxyl activating reagent comprises N, N' -dicyclohexylcarbodiimide;
the catechol group-containing compound includes 3, 4-dihydroxybenzoic acid or 3, 4-dihydroxyphenylacetic acid or more having a catechol group.
10. The method of claim 9, wherein the first temperature is between-5 ℃ and the second temperature is between 10 ℃ and 40 ℃;
and stirring the second mixed solution at the second temperature for 2.5-3.5 hours.
11. An imprinting template, comprising a substrate, a middle transition adhesion layer and an ultraviolet light curing adhesive layer, wherein the middle transition adhesion layer is arranged on one side of the substrate, and the ultraviolet light curing adhesive layer is arranged on one side of the middle transition adhesion layer, which is away from the substrate, wherein the material of the middle transition adhesion layer comprises the ultraviolet light curing nano imprinting material according to any one of claims 1-8.
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| WO2009110496A1 (en) * | 2008-03-07 | 2009-09-11 | 富士フイルム株式会社 | (meth)acrylate compound, curable composition using the same, composition for optical nanoimprint, cured product of the curable composition, and method for producing the cured product |
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