JP6134367B2 - フォトレジスト保護膜組成物 - Google Patents
フォトレジスト保護膜組成物 Download PDFInfo
- Publication number
- JP6134367B2 JP6134367B2 JP2015204525A JP2015204525A JP6134367B2 JP 6134367 B2 JP6134367 B2 JP 6134367B2 JP 2015204525 A JP2015204525 A JP 2015204525A JP 2015204525 A JP2015204525 A JP 2015204525A JP 6134367 B2 JP6134367 B2 JP 6134367B2
- Authority
- JP
- Japan
- Prior art keywords
- optionally substituted
- alkyl
- hydrogen
- polymer
- protective film
- 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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- 239000000203 mixture Substances 0.000 title claims description 165
- 229920002120 photoresistant polymer Polymers 0.000 title claims description 111
- 230000001681 protective effect Effects 0.000 title claims description 70
- 229920000642 polymer Polymers 0.000 claims description 166
- 239000011159 matrix material Substances 0.000 claims description 77
- 239000000178 monomer Substances 0.000 claims description 51
- 229910052739 hydrogen Inorganic materials 0.000 claims description 48
- 239000001257 hydrogen Substances 0.000 claims description 48
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 45
- -1 C10 alkyl hydrogen Chemical compound 0.000 claims description 31
- 239000003960 organic solvent Substances 0.000 claims description 23
- 239000007787 solid Substances 0.000 claims description 21
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims description 18
- 125000000217 alkyl group Chemical group 0.000 claims description 18
- 150000004945 aromatic hydrocarbons Chemical class 0.000 claims description 17
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 17
- 229910052760 oxygen Inorganic materials 0.000 claims description 17
- 239000001301 oxygen Substances 0.000 claims description 17
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 16
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 16
- 229910052717 sulfur Inorganic materials 0.000 claims description 16
- 239000011593 sulfur Substances 0.000 claims description 16
- 125000005647 linker group Chemical group 0.000 claims description 14
- 229910052710 silicon Inorganic materials 0.000 claims description 14
- 239000010703 silicon Substances 0.000 claims description 14
- 125000006732 (C1-C15) alkyl group Chemical group 0.000 claims description 13
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 claims description 11
- 239000000654 additive Substances 0.000 claims description 10
- 125000006850 spacer group Chemical group 0.000 claims description 10
- 229910052731 fluorine Inorganic materials 0.000 claims description 8
- 239000011737 fluorine Substances 0.000 claims description 6
- AQYSYJUIMQTRMV-UHFFFAOYSA-N hypofluorous acid Chemical compound FO AQYSYJUIMQTRMV-UHFFFAOYSA-N 0.000 claims description 4
- CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical compound FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 claims description 4
- PIGFYZPCRLYGLF-UHFFFAOYSA-N Aluminum nitride Chemical compound [Al]#N PIGFYZPCRLYGLF-UHFFFAOYSA-N 0.000 claims description 3
- 125000001153 fluoro group Chemical group F* 0.000 claims description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 2
- 229920001296 polysiloxane Polymers 0.000 claims 1
- 239000011253 protective coating Substances 0.000 claims 1
- 239000010410 layer Substances 0.000 description 109
- 238000000034 method Methods 0.000 description 58
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 40
- 230000008569 process Effects 0.000 description 35
- 239000000463 material Substances 0.000 description 33
- 239000002904 solvent Substances 0.000 description 28
- 239000000243 solution Substances 0.000 description 27
- LLHKCFNBLRBOGN-UHFFFAOYSA-N propylene glycol methyl ether acetate Chemical compound COCC(C)OC(C)=O LLHKCFNBLRBOGN-UHFFFAOYSA-N 0.000 description 23
- 239000002253 acid Substances 0.000 description 21
- CATSNJVOTSVZJV-UHFFFAOYSA-N heptan-2-one Chemical compound CCCCCC(C)=O CATSNJVOTSVZJV-UHFFFAOYSA-N 0.000 description 21
- 238000011161 development Methods 0.000 description 20
- 238000007654 immersion Methods 0.000 description 20
- 229910052757 nitrogen Inorganic materials 0.000 description 20
- 239000000758 substrate Substances 0.000 description 19
- 235000012431 wafers Nutrition 0.000 description 18
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 18
- 239000007788 liquid Substances 0.000 description 17
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 16
- 238000006116 polymerization reaction Methods 0.000 description 15
- 230000015572 biosynthetic process Effects 0.000 description 14
- LZCLXQDLBQLTDK-UHFFFAOYSA-N ethyl 2-hydroxypropanoate Chemical compound CCOC(=O)C(C)O LZCLXQDLBQLTDK-UHFFFAOYSA-N 0.000 description 14
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 12
- 230000005587 bubbling Effects 0.000 description 11
- 238000001459 lithography Methods 0.000 description 11
- 230000005855 radiation Effects 0.000 description 11
- 239000004065 semiconductor Substances 0.000 description 11
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 229920001577 copolymer Polymers 0.000 description 9
- RXGUIWHIADMCFC-UHFFFAOYSA-N 2-Methylpropyl 2-methylpropionate Chemical compound CC(C)COC(=O)C(C)C RXGUIWHIADMCFC-UHFFFAOYSA-N 0.000 description 8
- SOGAXMICEFXMKE-UHFFFAOYSA-N Butylmethacrylate Chemical compound CCCCOC(=O)C(C)=C SOGAXMICEFXMKE-UHFFFAOYSA-N 0.000 description 8
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 8
- 239000003999 initiator Substances 0.000 description 8
- 150000002576 ketones Chemical class 0.000 description 8
- 239000003973 paint Substances 0.000 description 8
- 238000003786 synthesis reaction Methods 0.000 description 8
- 239000006117 anti-reflective coating Substances 0.000 description 7
- 150000001875 compounds Chemical class 0.000 description 7
- 229940116333 ethyl lactate Drugs 0.000 description 7
- 229920005989 resin Polymers 0.000 description 7
- 239000011347 resin Substances 0.000 description 7
- 238000003756 stirring Methods 0.000 description 7
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 6
- FFWSICBKRCICMR-UHFFFAOYSA-N 5-methyl-2-hexanone Chemical compound CC(C)CCC(C)=O FFWSICBKRCICMR-UHFFFAOYSA-N 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- 230000003213 activating effect Effects 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- 238000000671 immersion lithography Methods 0.000 description 6
- 238000004528 spin coating Methods 0.000 description 6
- PTTPXKJBFFKCEK-UHFFFAOYSA-N 2-Methyl-4-heptanone Chemical compound CC(C)CC(=O)CC(C)C PTTPXKJBFFKCEK-UHFFFAOYSA-N 0.000 description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 5
- 230000000996 additive effect Effects 0.000 description 5
- 125000001931 aliphatic group Chemical group 0.000 description 5
- 230000003667 anti-reflective effect Effects 0.000 description 5
- 238000000576 coating method Methods 0.000 description 5
- 238000004090 dissolution Methods 0.000 description 5
- 238000005530 etching Methods 0.000 description 5
- 229920001519 homopolymer Polymers 0.000 description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 5
- 238000000206 photolithography Methods 0.000 description 5
- 230000003068 static effect Effects 0.000 description 5
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 5
- 125000003161 (C1-C6) alkylene group Chemical group 0.000 description 4
- KBPLFHHGFOOTCA-UHFFFAOYSA-N 1-Octanol Chemical compound CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 4
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 4
- XLLIQLLCWZCATF-UHFFFAOYSA-N 2-methoxyethyl acetate Chemical compound COCCOC(C)=O XLLIQLLCWZCATF-UHFFFAOYSA-N 0.000 description 4
- RUMACXVDVNRZJZ-UHFFFAOYSA-N 2-methylpropyl 2-methylprop-2-enoate Chemical compound CC(C)COC(=O)C(C)=C RUMACXVDVNRZJZ-UHFFFAOYSA-N 0.000 description 4
- 101100434207 Arabidopsis thaliana ACT8 gene Proteins 0.000 description 4
- 239000004971 Cross linker Substances 0.000 description 4
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 4
- 229920000877 Melamine resin Polymers 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- XUPYJHCZDLZNFP-UHFFFAOYSA-N butyl butanoate Chemical compound CCCCOC(=O)CCC XUPYJHCZDLZNFP-UHFFFAOYSA-N 0.000 description 4
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
- 230000008859 change Effects 0.000 description 4
- 239000011248 coating agent Substances 0.000 description 4
- 238000010511 deprotection reaction Methods 0.000 description 4
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 4
- FKRCODPIKNYEAC-UHFFFAOYSA-N ethyl propionate Chemical compound CCOC(=O)CC FKRCODPIKNYEAC-UHFFFAOYSA-N 0.000 description 4
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 4
- 238000003384 imaging method Methods 0.000 description 4
- JDSHMPZPIAZGSV-UHFFFAOYSA-N melamine Chemical compound NC1=NC(N)=NC(N)=N1 JDSHMPZPIAZGSV-UHFFFAOYSA-N 0.000 description 4
- 238000000059 patterning Methods 0.000 description 4
- 238000012545 processing Methods 0.000 description 4
- 239000011241 protective layer Substances 0.000 description 4
- 238000010926 purge Methods 0.000 description 4
- 238000002310 reflectometry Methods 0.000 description 4
- SJMYWORNLPSJQO-UHFFFAOYSA-N tert-butyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OC(C)(C)C SJMYWORNLPSJQO-UHFFFAOYSA-N 0.000 description 4
- ARXJGSRGQADJSQ-UHFFFAOYSA-N 1-methoxypropan-2-ol Chemical compound COCC(C)O ARXJGSRGQADJSQ-UHFFFAOYSA-N 0.000 description 3
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Natural products CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 3
- 229920003270 Cymel® Polymers 0.000 description 3
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 3
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 3
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 3
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 3
- SLINHMUFWFWBMU-UHFFFAOYSA-N Triisopropanolamine Chemical compound CC(O)CN(CC(C)O)CC(C)O SLINHMUFWFWBMU-UHFFFAOYSA-N 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 3
- 150000008064 anhydrides Chemical group 0.000 description 3
- PGMYKACGEOXYJE-UHFFFAOYSA-N anhydrous amyl acetate Natural products CCCCCOC(C)=O PGMYKACGEOXYJE-UHFFFAOYSA-N 0.000 description 3
- 230000004888 barrier function Effects 0.000 description 3
- BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 description 3
- BTMVHUNTONAYDX-UHFFFAOYSA-N butyl propionate Chemical compound CCCCOC(=O)CC BTMVHUNTONAYDX-UHFFFAOYSA-N 0.000 description 3
- 238000005229 chemical vapour deposition Methods 0.000 description 3
- 239000002872 contrast media Substances 0.000 description 3
- 238000001312 dry etching Methods 0.000 description 3
- 239000012776 electronic material Substances 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 125000005842 heteroatom Chemical group 0.000 description 3
- 238000002386 leaching Methods 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 238000005259 measurement Methods 0.000 description 3
- QQZOPKMRPOGIEB-UHFFFAOYSA-N n-butyl methyl ketone Natural products CCCCC(C)=O QQZOPKMRPOGIEB-UHFFFAOYSA-N 0.000 description 3
- 238000005240 physical vapour deposition Methods 0.000 description 3
- 238000001020 plasma etching Methods 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- PWQLFIKTGRINFF-UHFFFAOYSA-N tert-butyl 4-hydroxypiperidine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCC(O)CC1 PWQLFIKTGRINFF-UHFFFAOYSA-N 0.000 description 3
- WLOQLWBIJZDHET-UHFFFAOYSA-N triphenylsulfonium Chemical compound C1=CC=CC=C1[S+](C=1C=CC=CC=1)C1=CC=CC=C1 WLOQLWBIJZDHET-UHFFFAOYSA-N 0.000 description 3
- 239000012953 triphenylsulfonium Substances 0.000 description 3
- 239000008096 xylene Substances 0.000 description 3
- OOIBFPKQHULHSQ-UHFFFAOYSA-N (3-hydroxy-1-adamantyl) 2-methylprop-2-enoate Chemical compound C1C(C2)CC3CC2(O)CC1(OC(=O)C(=C)C)C3 OOIBFPKQHULHSQ-UHFFFAOYSA-N 0.000 description 2
- 125000006527 (C1-C5) alkyl group Chemical group 0.000 description 2
- 125000006528 (C2-C6) alkyl group Chemical group 0.000 description 2
- GEWWCWZGHNIUBW-UHFFFAOYSA-N 1-(4-nitrophenyl)propan-2-one Chemical compound CC(=O)CC1=CC=C([N+]([O-])=O)C=C1 GEWWCWZGHNIUBW-UHFFFAOYSA-N 0.000 description 2
- BBMCTIGTTCKYKF-UHFFFAOYSA-N 1-heptanol Chemical compound CCCCCCCO BBMCTIGTTCKYKF-UHFFFAOYSA-N 0.000 description 2
- TUIWMHDSXJWXOH-UHFFFAOYSA-N 2,5-dimethylhexan-3-one Chemical compound CC(C)CC(=O)C(C)C TUIWMHDSXJWXOH-UHFFFAOYSA-N 0.000 description 2
- IWSZDQRGNFLMJS-UHFFFAOYSA-N 2-(dibutylamino)ethanol Chemical compound CCCCN(CCO)CCCC IWSZDQRGNFLMJS-UHFFFAOYSA-N 0.000 description 2
- JVSWJIKNEAIKJW-UHFFFAOYSA-N 2-Methylheptane Chemical compound CCCCCC(C)C JVSWJIKNEAIKJW-UHFFFAOYSA-N 0.000 description 2
- DJYQGDNOPVHONN-UHFFFAOYSA-N 2-[bis(2-acetyloxyethyl)amino]ethyl acetate Chemical compound CC(=O)OCCN(CCOC(C)=O)CCOC(C)=O DJYQGDNOPVHONN-UHFFFAOYSA-N 0.000 description 2
- XHJGXOOOMKCJPP-UHFFFAOYSA-N 2-[tert-butyl(2-hydroxyethyl)amino]ethanol Chemical compound OCCN(C(C)(C)C)CCO XHJGXOOOMKCJPP-UHFFFAOYSA-N 0.000 description 2
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical class CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 2
- CETWDUZRCINIHU-UHFFFAOYSA-N 2-heptanol Chemical compound CCCCCC(C)O CETWDUZRCINIHU-UHFFFAOYSA-N 0.000 description 2
- ZDTRMJAWAIZCSV-UHFFFAOYSA-N 2-morpholin-4-ylethyl acetate Chemical compound CC(=O)OCCN1CCOCC1 ZDTRMJAWAIZCSV-UHFFFAOYSA-N 0.000 description 2
- ZPVFWPFBNIEHGJ-UHFFFAOYSA-N 2-octanone Chemical compound CCCCCCC(C)=O ZPVFWPFBNIEHGJ-UHFFFAOYSA-N 0.000 description 2
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 2
- KUMXLFIBWFCMOJ-UHFFFAOYSA-N 3,3-dimethylhexane Chemical compound CCCC(C)(C)CC KUMXLFIBWFCMOJ-UHFFFAOYSA-N 0.000 description 2
- LAIUFBWHERIJIH-UHFFFAOYSA-N 3-Methylheptane Chemical compound CCCCC(C)CC LAIUFBWHERIJIH-UHFFFAOYSA-N 0.000 description 2
- OFNISBHGPNMTMS-UHFFFAOYSA-N 3-methylideneoxolane-2,5-dione Chemical compound C=C1CC(=O)OC1=O OFNISBHGPNMTMS-UHFFFAOYSA-N 0.000 description 2
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 description 2
- HCFAJYNVAYBARA-UHFFFAOYSA-N 4-heptanone Chemical compound CCCC(=O)CCC HCFAJYNVAYBARA-UHFFFAOYSA-N 0.000 description 2
- GZVHEAJQGPRDLQ-UHFFFAOYSA-N 6-phenyl-1,3,5-triazine-2,4-diamine Chemical compound NC1=NC(N)=NC(C=2C=CC=CC=2)=N1 GZVHEAJQGPRDLQ-UHFFFAOYSA-N 0.000 description 2
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 2
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 2
- XZMCDFZZKTWFGF-UHFFFAOYSA-N Cyanamide Chemical compound NC#N XZMCDFZZKTWFGF-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- RZKSECIXORKHQS-UHFFFAOYSA-N Heptan-3-ol Chemical compound CCCCC(O)CC RZKSECIXORKHQS-UHFFFAOYSA-N 0.000 description 2
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 2
- RJUFJBKOKNCXHH-UHFFFAOYSA-N Methyl propionate Chemical compound CCC(=O)OC RJUFJBKOKNCXHH-UHFFFAOYSA-N 0.000 description 2
- XYVQFUJDGOBPQI-UHFFFAOYSA-N Methyl-2-hydoxyisobutyric acid Chemical compound COC(=O)C(C)(C)O XYVQFUJDGOBPQI-UHFFFAOYSA-N 0.000 description 2
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 2
- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 2
- ZWXPDGCFMMFNRW-UHFFFAOYSA-N N-methylcaprolactam Chemical compound CN1CCCCCC1=O ZWXPDGCFMMFNRW-UHFFFAOYSA-N 0.000 description 2
- 229910052581 Si3N4 Inorganic materials 0.000 description 2
- 239000004809 Teflon Substances 0.000 description 2
- 229920006362 Teflon® Polymers 0.000 description 2
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 2
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
- 125000004036 acetal group Chemical group 0.000 description 2
- 125000002723 alicyclic group Chemical group 0.000 description 2
- 125000002947 alkylene group Chemical group 0.000 description 2
- 229910052782 aluminium Inorganic materials 0.000 description 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 2
- 150000001408 amides Chemical class 0.000 description 2
- NMJJFJNHVMGPGM-UHFFFAOYSA-N butyl formate Chemical compound CCCCOC=O NMJJFJNHVMGPGM-UHFFFAOYSA-N 0.000 description 2
- 239000004202 carbamide Substances 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 229910052802 copper Inorganic materials 0.000 description 2
- 239000010949 copper Substances 0.000 description 2
- 150000003950 cyclic amides Chemical class 0.000 description 2
- 125000000753 cycloalkyl group Chemical group 0.000 description 2
- DIOQZVSQGTUSAI-UHFFFAOYSA-N decane Chemical compound CCCCCCCCCC DIOQZVSQGTUSAI-UHFFFAOYSA-N 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000004210 ether based solvent Substances 0.000 description 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 125000003709 fluoroalkyl group Chemical group 0.000 description 2
- VPVSTMAPERLKKM-UHFFFAOYSA-N glycoluril Chemical compound N1C(=O)NC2NC(=O)NC21 VPVSTMAPERLKKM-UHFFFAOYSA-N 0.000 description 2
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical compound CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 description 2
- QNVRIHYSUZMSGM-UHFFFAOYSA-N hexan-2-ol Chemical compound CCCCC(C)O QNVRIHYSUZMSGM-UHFFFAOYSA-N 0.000 description 2
- ZOCHHNOQQHDWHG-UHFFFAOYSA-N hexan-3-ol Chemical compound CCCC(O)CC ZOCHHNOQQHDWHG-UHFFFAOYSA-N 0.000 description 2
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- YWXLSHOWXZUMSR-UHFFFAOYSA-N octan-4-one Chemical compound CCCCC(=O)CCC YWXLSHOWXZUMSR-UHFFFAOYSA-N 0.000 description 1
- NUJGJRNETVAIRJ-UHFFFAOYSA-N octanal Chemical compound CCCCCCCC=O NUJGJRNETVAIRJ-UHFFFAOYSA-N 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
- UUEVFMOUBSLVJW-UHFFFAOYSA-N oxo-[[1-[2-[2-[2-[4-(oxoazaniumylmethylidene)pyridin-1-yl]ethoxy]ethoxy]ethyl]pyridin-4-ylidene]methyl]azanium;dibromide Chemical compound [Br-].[Br-].C1=CC(=C[NH+]=O)C=CN1CCOCCOCCN1C=CC(=C[NH+]=O)C=C1 UUEVFMOUBSLVJW-UHFFFAOYSA-N 0.000 description 1
- RVTZCBVAJQQJTK-UHFFFAOYSA-N oxygen(2-);zirconium(4+) Chemical compound [O-2].[O-2].[Zr+4] RVTZCBVAJQQJTK-UHFFFAOYSA-N 0.000 description 1
- LGUZHRODIJCVOC-UHFFFAOYSA-N perfluoroheptane Chemical compound FC(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F LGUZHRODIJCVOC-UHFFFAOYSA-N 0.000 description 1
- 238000005191 phase separation Methods 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- QCCDLTOVEPVEJK-UHFFFAOYSA-N phenylacetone Chemical compound CC(=O)CC1=CC=CC=C1 QCCDLTOVEPVEJK-UHFFFAOYSA-N 0.000 description 1
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 description 1
- 230000036211 photosensitivity Effects 0.000 description 1
- 238000005268 plasma chemical vapour deposition Methods 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 229910021420 polycrystalline silicon Inorganic materials 0.000 description 1
- 239000005076 polymer ester Substances 0.000 description 1
- 229920005591 polysilicon Polymers 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- ILVGAIQLOCKNQA-UHFFFAOYSA-N propyl 2-hydroxypropanoate Chemical compound CCCOC(=O)C(C)O ILVGAIQLOCKNQA-UHFFFAOYSA-N 0.000 description 1
- 150000003216 pyrazines Chemical class 0.000 description 1
- 150000003217 pyrazoles Chemical class 0.000 description 1
- 150000003222 pyridines Chemical class 0.000 description 1
- 150000003233 pyrroles Chemical class 0.000 description 1
- 150000004040 pyrrolidinones Chemical class 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- 230000002829 reductive effect Effects 0.000 description 1
- 238000007761 roller coating Methods 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 238000005204 segregation Methods 0.000 description 1
- 229910021332 silicide Inorganic materials 0.000 description 1
- 229910052814 silicon oxide Inorganic materials 0.000 description 1
- 238000004544 sputter deposition Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 150000003871 sulfonates Chemical class 0.000 description 1
- 150000003459 sulfonic acid esters Chemical class 0.000 description 1
- 239000002344 surface layer Substances 0.000 description 1
- 229910052715 tantalum Inorganic materials 0.000 description 1
- GUVRBAGPIYLISA-UHFFFAOYSA-N tantalum atom Chemical compound [Ta] GUVRBAGPIYLISA-UHFFFAOYSA-N 0.000 description 1
- 230000008685 targeting Effects 0.000 description 1
- ISXSCDLOGDJUNJ-UHFFFAOYSA-N tert-butyl prop-2-enoate Chemical compound CC(C)(C)OC(=O)C=C ISXSCDLOGDJUNJ-UHFFFAOYSA-N 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
- 150000003918 triazines Chemical class 0.000 description 1
- TUODWSVQODNTSU-UHFFFAOYSA-M trifluoromethanesulfonate;tris[4-[(2-methylpropan-2-yl)oxy]phenyl]sulfanium Chemical compound [O-]S(=O)(=O)C(F)(F)F.C1=CC(OC(C)(C)C)=CC=C1[S+](C=1C=CC(OC(C)(C)C)=CC=1)C1=CC=C(OC(C)(C)C)C=C1 TUODWSVQODNTSU-UHFFFAOYSA-M 0.000 description 1
- FAYMLNNRGCYLSR-UHFFFAOYSA-M triphenylsulfonium triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F.C1=CC=CC=C1[S+](C=1C=CC=CC=1)C1=CC=CC=C1 FAYMLNNRGCYLSR-UHFFFAOYSA-M 0.000 description 1
- 229910001928 zirconium oxide Inorganic materials 0.000 description 1
Images
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- 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
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- 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
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- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
- G03F7/0046—Photosensitive materials with perfluoro compounds, e.g. for dry lithography
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- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
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- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
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- G03F7/0752—Silicon-containing compounds in non photosensitive layers or as additives, e.g. for dry lithography
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- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
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- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
- G03F7/09—Photosensitive materials characterised by structural details, e.g. supports, auxiliary layers
- G03F7/091—Photosensitive materials characterised by structural details, e.g. supports, auxiliary layers characterised by antireflection means or light filtering or absorbing means, e.g. anti-halation, contrast enhancement
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- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
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- 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
- G03F7/20—Exposure; Apparatus therefor
- G03F7/2041—Exposure; Apparatus therefor in the presence of a fluid, e.g. immersion; using fluid cooling means
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
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- C08F220/00—Copolymers 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
- C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
- C08F220/10—Esters
- C08F220/12—Esters of monohydric alcohols or phenols
- C08F220/16—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms
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- C09D133/00—Coating compositions based on homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Coating compositions based on derivatives of such polymers
- C09D133/04—Homopolymers or copolymers of esters
- C09D133/06—Homopolymers or copolymers of esters of esters containing only carbon, hydrogen and oxygen, the oxygen atom being present only as part of the carboxyl radical
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Description
以下の一般式(II)または(III)のモノマーから形成される単位を含む付加ポリマーであって、
フォトレジスト保護膜組成物は、マトリックスポリマー、付加ポリマー、塩基性クエンチャー、及び有機溶媒を含む。付加ポリマーは、マトリックスポリマーの表面エネルギーより低い表面エネルギーを有する。本発明の組成物は、ネガ型現像プロセスでフォトレジスト層上にコーティングされる時、改善された浸漬液との接触角特徴、改善された焦点許容範囲、改善された露光許容範囲、低欠陥性、浸漬液へのフォトレジスト及び保護膜構成要素の浸出の回避のための効果的な障壁層特性、幾何学的に均一なレジストパターン、及びレジスト露光中の低反射性のうちの1つ以上等の様々な利点を提供することができる。組成物は、乾燥リソグラフィーまたは液浸リソグラフィープロセスで使用され得る。露光波長は、特に限定されないが、但し、248nmもしくは193nm等の200nm以下(浸漬または乾燥リソグラフィー)、またはEUV波長(例えば、13.4nm)が典型的なフォトレジスト組成物を除く。
本発明において有用なフォトレジスト組成物は、酸に弱いマトリックス樹脂を含む化学的に増幅されたフォトレジスト組成物を含み、フォトレジスト組成物の層の一部として、樹脂及び組成物層は、光酸発生剤によって生成される酸との反応、後続するソフトベーク、活性化放射線への露光、及び露光後ベークの結果として、有機現像液の溶解性の変化を受けることを意味する。溶解性の変化は、マトリックスポリマー中の光酸に不安定なエステルまたはアセタール基等の酸切断可能な脱離基が、酸またはアルコール基を生産するための活性化放射線及び熱処理への露光の状態で光酸によって促進される脱保護反応を受けるときに引き起こされる。本発明に有用な好適なフォトレジスト組成物が市販されている。
本発明に従って組成物を使用するプロセスは、ネガ型現像によってフォトリソグラフィーパターンを形成するための例示のプロセスフローを説明する図1A〜Cを参照してここで記述される。
IPAMA(20.68g)、IPCPMA(24.72g)、aGBLMA(27.78g)、X−GM−HL−2(17.26g)、及びHAMA(11.46g)のモノマーを、108.33gの乳酸エチル/γ−ブチロラクトン(gBL)(7/3)に溶解した。モノマー溶液を20分間、窒素で泡立てることによって脱気した。乳酸エチル/γ−ブチロラクトン(gBL)(113g)を、凝縮装置及び機械的攪拌機を備える500mLのジャケット反応器へ投入し、20分間、窒素で泡立てることによって脱気した。続いて、反応フラスコ内の溶媒を、80℃の温度まで上げた。V−601(ジメチル−2,2−アゾジイソブチラート)(3.974g)を12gの乳酸エチル/gBLに溶解し、開始剤溶液を20分間、窒素で泡立てることによって脱気した。開始剤溶液を反応器へ添加し、その後、モノマー溶液を、厳密な攪拌及び窒素環境下で3.5時間にわたる滴下で反応器へ供給した。モノマー供給が完了した後、重合混合物を80℃でさらに0.5時間、静置した。反応が完了した後、重合混合物を室温まで冷却させた。沈降をMeOH(3000g)中で行った。沈降された粉を、濾過によって回収し、一晩空気乾燥させ、120gのTHFに再溶解し、MeOH(3000g)へ再沈降した。最終ポリマーを濾過し、一晩空気乾燥させ、48時間、60℃で、真空下でさらに乾燥させ、ポリマーPP−1を得た(Mw=7785;PDI=1.36;収率=82.75%).
30gのイソブチルメタアクリレート(iBMA)及び10gのn−ブチルメタアクリレート(nBMA)モノマーを、60gのPGMEAに溶解した。モノマー溶液を20分間、窒素で泡立てることによって脱気した。PGMEA(32.890g)を、凝縮装置及び機械的攪拌機を備える500mLの三つ口フラスコへ投入し、20分間、窒素で泡立てることによって脱気した。続いて、反応フラスコ内の溶媒を、80℃の温度まで上げた。V601(3.239g)を8gのPGMEAに溶解し、開始剤溶液を20分間、窒素で泡立てることによって脱気した。開始剤溶液を反応フラスコへ添加し、その後、モノマー溶液を、厳密な攪拌及び窒素環境下で3時間にわたる滴下で反応器へ供給した。モノマー供給が完了した後、重合混合物を80℃でさらに1時間、静置した。合計4時間の重合時間(3時間の供給及び1時間の供給後撹拌)の後、重合混合物を室温まで冷却させた。沈降をメタノール/水(8/2)混合物(1730g)中で行った。沈降されたポリマーを、濾過によって回収し、一晩空気乾燥させ、120gのTHFに再溶解し、メタノール/水(8/2)混合物(1730g)へ再沈降した。最終ポリマーを濾過し、一晩空気乾燥させ、48時間、25℃で、真空下でさらに乾燥させ、33.1gのポリ(iBMA/nBMA)(75/25)コポリマー(MP−1)を得た(Mw=9,203;Mw/Mn=1.60;収率=82.75%)。合成の結果は、表1に記載される。
25gのPGMEAを200mlの反応器に投入し、30分間、窒素パージ下で99℃まで加熱した。27.5gのMA−MIB−HFAモノマー、12.5gのMA−DM−EATfモノマー、及び10gの233−tMBAモノマーを7.02gのPGMEA溶媒に溶解し、モノマー溶液を窒素で泡立てることによって脱気した。1.80gのV601(ジメチル−2,2−アゾジイソブチラート)を16.18gのPGMEAに溶解し、モノマー溶液を窒素で泡立てることによって脱気した。開始剤溶液を、0.150g/分の供給速度で120分にわたる滴下で反応器へ供給した。モノマー溶液も、厳密な攪拌及び窒素環境下で供給速度0.475g/分で120分にわたる滴下で反応器へ供給した。供給が完了した後、重合混合物をさらに2時間、静置した。重合混合物を、その後、室温まで冷却させ、ポリ(MA−MIB−HFA/MA−DM−EATf/tMBA)(55/25/20)コポリマー(AP−1)の溶液を結果として得た(Mw=9017;Mw/Mn=1.87;収率=35.7%)。合成の結果は、表1に記載される。
25gのPGMEAを200mlの反応器に投入し、30分間、窒素パージ下で99℃まで加熱した。40gのMA−MIB−HFA/モノマー及び10gの233−tMBAモノマーを混合し、10gのPGMEA溶媒に溶解した。1.50gのV601(ジメチル−2,2−アゾジイソブチラート)を13.5gのPGMEAに溶解した。モノマー及び開始剤溶液を窒素で泡立てることによって脱気した。開始剤溶液を、0.136g/分の供給速度で110分にわたって滴下で反応器へ供給した。モノマー溶液も、厳密な攪拌及び窒素環境下で、0.545g/分の供給速度で、110分にわたる滴下で反応器へ供給した。供給が完了した後、重合混合物をさらに2時間、静置した。重合混合物を、その後、室温まで冷却させ、ポリ(MA−MIB−HFA/233−tMBA)(80/20)コポリマー(AP−2)の溶液を結果として得た(Mw=8945;Mw/Mn=1.91;収率=42.1%)。合成の結果は、表1に記載される。
300gのイソブチルイソブチラート(IBIB)を2Lの反応器に投入し、窒素パージ下で99℃まで加熱した。400gのMA−MIB−HFAモノマー及び14.4gのV601(ジメチル−2,2−アゾジイソブチラート)を285.7gのIBIBに溶解し、モノマー溶液を窒素で泡立てることによって脱気し、続いて、厳密な攪拌及び窒素環境下で、120分の期間にわたる滴下で反応器へ供給した。モノマー供給が完了した後、重合混合物を99℃でさらに5時間、静置した。重合混合物を、その後、室温まで冷却させ、ポリ(MA−MIB−HFA)ホモポリマー(AP−3)の溶液を結果として得た(Mw=6768;Mw/Mn=1.658;収率=29.83%)。合成の結果は、表1に記載される。
53.94gのPGMEAを300mlの反応器に投入し、30分間、窒素パージ下で99℃まで加熱した。57.18gのTBMAモノマー及び50.7gのMHFPMAモノマー混合し、15.14gのPGMEAに溶解した。モノマー溶液を窒素で泡立てることによって脱気した。3.88gのV601(ジメチル−2,2−アゾジイソブチラート)を34.91gのPGMEAに溶解し、開始剤溶液を、0.353g/分の供給速度で110分にわたって滴下で反応器へ供給した。モノマー溶液も、厳密な攪拌及び窒素環境下で、1.118g/分の供給速度で、110分にわたる滴下で反応器へ供給した。供給が完了した後、重合混合物をさらに2時間、静置した。重合混合物を、その後、室温まで冷却させ、ポリ(TBMA/MHFPMA)コポリマー(AP−4)の溶液を結果として得た(Mw=10,944;Mw/Mn=1.74;収率=45.2%)。合成の結果は、表1に記載される。
PGMEA中の31.219gのポリマーPP−1溶液(10重量%)、PGMEA中の5.415gのトリフェニルスルホニウムペルフルオロブタンスルホン酸塩溶液(1重量%)、PGMEA中の15.047gのトリフェニルスルホニウム2−(((3r,5r,7r)−アダマンタン−1−カルボニル)オキシ)−1,1−ジフルオロエタンスルホン酸塩溶液(1重量%)、PGMEA中の3.01gの2,2’−(ドデシルアザンジイル)ジエタノール溶液(1%)、PGMEA中の14.336gのトリフェニルスルホニウム ((1S,4S)−7,7−ジメチル−2−オキサビシクロ[2.2.1]ヘプタン−1−イル)メタンスルホン酸塩(1%)、21.324gのPGMEA、及び9.650gのγ−ブチロラクトンを4時間混合した。混合物を0.2ミクロンのナイロン濾紙で濾過し、フォトレジスト組成物PC−1を得た。
レジスト保護膜組成物は、表2に記載される構成要素及び量を使用して、保護膜マトリックスポリマー、付加ポリマー、及び塩基性クエンチャーを溶媒に溶解することによって調製した。結果として得られた混合物を、3時間、機械的ローラーで伸ばし、その後、0.2ミクロンの孔径を有するテフロン(登録商標)濾紙を介して濾過した。組成物は、保護膜表面での反射率を低減させるための入射波の波長の4分の1に対応する、290Åの目的の厚さ(約1500rpmでのスピンコーティング後)に基づいて、調合した。
DI水に対する静的接触角(SCA)、後退接触角(RCA)、前進接触角(ACA)、及び転落角(SA)を、各レジスト保護膜組成物に対して測定した。静的及び動的接触角を、KRUSS滴形状分析モデル100を使用して測定した。動的接触角測定のために、DI水の滴の大きさは、50μl(マイクロリットル)であり、ウエハーステージ傾斜率1単位/秒であった。水滴が、試験用ウエハー表面上に配置されると、ウエハーステージは、すぐに傾斜し始めた。ウエハーステージ傾斜中、水滴が、その元の位置から転落するまで、1秒につき20コマの速度で、水滴の動画を撮った。ビデオの各コマを、その後、分析し、水滴がちょうど転落し始めた時のコマ上の水滴の画像を使用して、それらの対応する接線によって動的接触角(後退及び前進)を判定した。転落角は、水滴がちょうど転落し始めた時のコマに対応するウエハーステージ傾斜角である。静的接触角測定では、水滴は、2.5μlであり、傾斜させずに試験用ウエハー表面上に配置した。接触角は、水滴の両側上の接線によって判定した。報告された静的接触角は、水滴の左及び右側からの接触角の平均であった。表面エネルギーを、拡張フォークス理論を使用して水の静的接触角に基づいて計算した。接触角(SCA)、後退接触角(RCA)、前進接触角(ACA)、転落角(SA)、及びOC−1に関するRCAの差異(OC−1からのΔRCA)に対する結果は、表3に記載される。
乾燥リソグラフィーを行い、リソグラフィー性能に対する保護膜組成物の効果を調査した。ASML/1100スキャナに連結されるTEL CleanTrack ACT8上で、200mmのシリコンウエハーをAR(商標)19下部反射防止塗料(BARC)材料(Rohm and Haas Electronic Materials,Marlborough,MA)でスピン塗布し、205℃で60秒間ベークし、860Åの膜厚を得た。フォトレジスト組成物PC−1をBARCで塗布されたウエハー上で塗布し、TEL CleanTrack ACT8塗料/現像液上で60秒間、90℃でソフトベークし、1000Åのレジスト層厚を提供した。保護膜組成物は、使用された場合、レジストの上部に塗布し、TEL CleanTrack ACT8塗料/現像液上で60秒間、90℃でソフトベークし、290Åのレジスト層厚を提供した。ウエハーは、ASML1100スキャナで、0.75NA、0.89アウターシグマ、及び0.64インナーシグマを伴う四重極照明条件を使用して露光した。露光されたウエハーを、60秒間、90℃で露光後ベークし、TEL CleanTrack ACT8塗料/現像液上で30秒間、n−酢酸ブチル(NBA)現像液で現像した。限界寸法(CD)を、同じマスク特徴(6%PSM)で200nmのピッチでの濃いコンタクトホールに対して100nmを標的とし、200Kの倍率でのHitachi9380CD SEM上でホールパターンの直径で測定した。
EL=(1.1×CDt−0.9×CDt)(1.1のEopt×CDt−0.9のEopt×CDt)
レジスト保護膜組成物は、表5に記載される構成要素を使用して、9gのマトリックスポリマー,0.95gの付加ポリマー、及び0.05gのtert−ブチル4−ヒドロキシピペリジン−1−カルボキシレートを990gの溶媒に溶解することによって調製した、結果として得られた混合物を、3時間、機械的ローラーで伸ばし、その後、0.2ミクロンの孔径を有するテフロン(登録商標)濾紙を介して濾過する。
300mmのシリコンウエハーをAR(商標)19下部反射防止塗料(BARC)材料(Rohm and Haas Electronic Materials,Marlborough,MA)でスピン塗布し、205℃で60秒間ベークし、860Åの膜厚を得る。フォトレジスト組成物PC−1を、BARCで塗布されたウエハー上でスピン塗布し、60秒間、90℃でソフトベークし、1000Åのレジスト層厚を提供する。表5の保護膜組成物をレジストの上部にスピン塗布し、60秒間、90℃でソフトベークし、レジスト保護膜層を提供する。ウエハーを、浸漬スキャナ上で露光し、その後、スピン塗料上で25秒間、2−ヘプタノンを使用して現像し、ネガ型パターンを得た。
Claims (10)
- 以下の一般式(I)のモノマーから形成される単位を含むマトリックスポリマーであって、
以下の一般式(II)のモノマーから形成される単位を含む付加ポリマーであって、
塩基性クエンチャーと、
有機溶媒と、を含む、フォトレジスト保護膜組成物であって、
前記付加ポリマーは、前記マトリックスポリマーの表面エネルギーより低い表面エネルギーを有し、前記付加ポリマーは、前記保護膜組成物の全固形物に基づいて、1〜15重量%の量で前記保護膜組成物中に存在する、前記フォトレジスト保護膜組成物。 - 以下の一般式(I)のモノマーから形成される単位を含むマトリックスポリマーであっ
て、
以下の一般式(II)のモノマーから形成される単位を含む付加ポリマーであって、
塩基性クエンチャーと、
有機溶媒と、を含む、フォトレジスト保護膜組成物であって、
前記付加ポリマーは、前記マトリックスポリマーの表面エネルギーより低い表面エネルギーを有し、前記付加ポリマーは、前記保護膜組成物の全固形物に基づいて、1〜20重量%の量で前記保護膜組成物中に存在し、前記マトリックスポリマーがフッ素もシリコンも含まない、前記フォトレジスト保護膜組成物。 - 以下の一般式(I)のモノマーから形成される単位を含むマトリックスポリマーであっ
て、
以下の一般式(III)のモノマーから形成される単位を含む付加ポリマーであって、
塩基性クエンチャーと、
有機溶媒と、を含む、フォトレジスト保護膜組成物であって、
前記付加ポリマーは、前記マトリックスポリマーの表面エネルギーより低い表面エネルギーを有し、前記付加ポリマーは、前記保護膜組成物の全固形物に基づいて、1〜20重量%の量で前記保護膜組成物中に存在する、前記フォトレジスト保護膜組成物。 - 以下の一般式(I)のモノマーから形成される単位を含むマトリックスポリマーであっ
て、
以下のモノマー:
塩基性クエンチャーと、
有機溶媒と、を含む、フォトレジスト保護膜組成物であって、
前記付加ポリマーは、前記マトリックスポリマーの表面エネルギーより低い表面エネルギーを有し、前記付加ポリマーは、前記保護膜組成物の全固形物に基づいて、1〜20重量%の量で前記保護膜組成物中に存在する、前記フォトレジスト保護膜組成物。 - 前記付加ポリマーは、フッ素原子を含有する単位を含む、請求項1〜4のいずれかに記載のフォトレジスト保護膜組成物。
- 前記付加ポリマーは、フルオロアルコールを含有する単位を含む、請求項5に記載のフォトレジスト保護膜組成物。
- 前記マトリックスポリマーは、フッ素もシリコンも含まない、請求項1、及び3〜6のいずれかに記載のフォトレジスト保護膜組成物。
- 前記塩基性クエンチャーは、前記マトリックスポリマー上に塩基性部分を含む、請求項1〜7のいずれかに記載のフォトレジスト保護膜組成物。
- 前記塩基性クエンチャーは、前記付加ポリマー及び前記マトリックスポリマーとは別の添加物である、請求項1〜8のいずれかに記載のフォトレジスト保護膜組成物。
- 前記付加ポリマーは、前記保護膜組成物の全固形物に基づいて、3〜15重量%の量で前記保護膜組成物中に存在する、請求項1〜9のいずれかに記載のフォトレジスト保護膜組成物。
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- 2015-10-29 KR KR1020150150954A patent/KR101826110B1/ko active IP Right Grant
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CN105573058B (zh) | 2019-12-20 |
CN105573058A (zh) | 2016-05-11 |
KR20160052375A (ko) | 2016-05-12 |
TW201616243A (zh) | 2016-05-01 |
US20160122574A1 (en) | 2016-05-05 |
JP2016091017A (ja) | 2016-05-23 |
TWI584073B (zh) | 2017-05-21 |
US9581904B2 (en) | 2017-02-28 |
KR101826110B1 (ko) | 2018-02-06 |
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