CN106662819B - 包含芳香族羟甲基化合物反应而得的酚醛清漆树脂的抗蚀剂下层膜形成用组合物 - Google Patents
包含芳香族羟甲基化合物反应而得的酚醛清漆树脂的抗蚀剂下层膜形成用组合物 Download PDFInfo
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- CN106662819B CN106662819B CN201580036571.3A CN201580036571A CN106662819B CN 106662819 B CN106662819 B CN 106662819B CN 201580036571 A CN201580036571 A CN 201580036571A CN 106662819 B CN106662819 B CN 106662819B
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- -1 aromatic methylol compound Chemical class 0.000 title claims abstract description 164
- 239000000203 mixture Substances 0.000 title claims abstract description 90
- OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Natural products OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 title claims abstract description 52
- 229920003986 novolac Polymers 0.000 title claims abstract description 29
- 229920005989 resin Polymers 0.000 title claims description 63
- 239000011347 resin Substances 0.000 title claims description 63
- 238000006243 chemical reaction Methods 0.000 title claims description 24
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 39
- 239000002904 solvent Substances 0.000 claims abstract description 31
- 125000003118 aryl group Chemical group 0.000 claims abstract description 30
- 150000001491 aromatic compounds Chemical class 0.000 claims abstract description 21
- BVJSUAQZOZWCKN-UHFFFAOYSA-N p-hydroxybenzyl alcohol Chemical compound OCC1=CC=C(O)C=C1 BVJSUAQZOZWCKN-UHFFFAOYSA-N 0.000 claims abstract description 10
- CQRYARSYNCAZFO-UHFFFAOYSA-N salicyl alcohol Chemical compound OCC1=CC=CC=C1O CQRYARSYNCAZFO-UHFFFAOYSA-N 0.000 claims abstract description 10
- HNURKXXMYARGAY-UHFFFAOYSA-N 2,6-Di-tert-butyl-4-hydroxymethylphenol Chemical compound CC(C)(C)C1=CC(CO)=CC(C(C)(C)C)=C1O HNURKXXMYARGAY-UHFFFAOYSA-N 0.000 claims abstract description 8
- 239000000758 substrate Substances 0.000 claims description 46
- 125000004432 carbon atom Chemical group C* 0.000 claims description 38
- 238000000034 method Methods 0.000 claims description 35
- 239000004065 semiconductor Substances 0.000 claims description 33
- 150000001875 compounds Chemical class 0.000 claims description 28
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 27
- 238000005530 etching Methods 0.000 claims description 26
- 239000002253 acid Substances 0.000 claims description 23
- 238000010894 electron beam technology Methods 0.000 claims description 21
- 125000000217 alkyl group Chemical group 0.000 claims description 17
- 239000003431 cross linking reagent Substances 0.000 claims description 14
- 238000004519 manufacturing process Methods 0.000 claims description 14
- 238000012545 processing Methods 0.000 claims description 14
- KLLLJCACIRKBDT-UHFFFAOYSA-N 2-phenyl-1H-indole Chemical group N1C2=CC=CC=C2C=C1C1=CC=CC=C1 KLLLJCACIRKBDT-UHFFFAOYSA-N 0.000 claims description 11
- 150000004982 aromatic amines Chemical class 0.000 claims description 10
- XQVWYOYUZDUNRW-UHFFFAOYSA-N N-Phenyl-1-naphthylamine Chemical compound C=1C=CC2=CC=CC=C2C=1NC1=CC=CC=C1 XQVWYOYUZDUNRW-UHFFFAOYSA-N 0.000 claims description 9
- 125000003342 alkenyl group Chemical group 0.000 claims description 9
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 9
- WQGWDDDVZFFDIG-UHFFFAOYSA-N pyrogallol Chemical compound OC1=CC=CC(O)=C1O WQGWDDDVZFFDIG-UHFFFAOYSA-N 0.000 claims description 8
- 150000001299 aldehydes Chemical class 0.000 claims description 7
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 7
- 230000001678 irradiating effect Effects 0.000 claims description 7
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 6
- 125000000304 alkynyl group Chemical group 0.000 claims description 5
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 5
- 125000004185 ester group Chemical group 0.000 claims description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 5
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 5
- 229910052717 sulfur Inorganic materials 0.000 claims description 5
- 125000004434 sulfur atom Chemical group 0.000 claims description 5
- KJCVRFUGPWSIIH-UHFFFAOYSA-N 1-naphthol Chemical compound C1=CC=C2C(O)=CC=CC2=C1 KJCVRFUGPWSIIH-UHFFFAOYSA-N 0.000 claims description 4
- BRPSWMCDEYMRPE-UHFFFAOYSA-N 4-[1,1-bis(4-hydroxyphenyl)ethyl]phenol Chemical compound C=1C=C(O)C=CC=1C(C=1C=CC(O)=CC=1)(C)C1=CC=C(O)C=C1 BRPSWMCDEYMRPE-UHFFFAOYSA-N 0.000 claims description 4
- HDPBBNNDDQOWPJ-UHFFFAOYSA-N 4-[1,2,2-tris(4-hydroxyphenyl)ethyl]phenol Chemical compound C1=CC(O)=CC=C1C(C=1C=CC(O)=CC=1)C(C=1C=CC(O)=CC=1)C1=CC=C(O)C=C1 HDPBBNNDDQOWPJ-UHFFFAOYSA-N 0.000 claims description 4
- WFCQTAXSWSWIHS-UHFFFAOYSA-N 4-[bis(4-hydroxyphenyl)methyl]phenol Chemical compound C1=CC(O)=CC=C1C(C=1C=CC(O)=CC=1)C1=CC=C(O)C=C1 WFCQTAXSWSWIHS-UHFFFAOYSA-N 0.000 claims description 4
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 claims description 4
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 4
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 4
- OHUWRYQKKWKGKG-UHFFFAOYSA-N formaldehyde;pyrene Chemical compound O=C.C1=CC=C2C=CC3=CC=CC4=CC=C1C2=C43 OHUWRYQKKWKGKG-UHFFFAOYSA-N 0.000 claims description 4
- 125000005843 halogen group Chemical group 0.000 claims description 4
- 125000004970 halomethyl group Chemical group 0.000 claims description 4
- 150000002576 ketones Chemical class 0.000 claims description 4
- NCIAGQNZQHYKGR-UHFFFAOYSA-N naphthalene-1,2,3-triol Chemical compound C1=CC=C2C(O)=C(O)C(O)=CC2=C1 NCIAGQNZQHYKGR-UHFFFAOYSA-N 0.000 claims description 4
- NXPPAOGUKPJVDI-UHFFFAOYSA-N naphthalene-1,2-diol Chemical compound C1=CC=CC2=C(O)C(O)=CC=C21 NXPPAOGUKPJVDI-UHFFFAOYSA-N 0.000 claims description 4
- 125000003277 amino group Chemical group 0.000 claims description 3
- SQAINHDHICKHLX-UHFFFAOYSA-N 1-naphthaldehyde Chemical group C1=CC=C2C(C=O)=CC=CC2=C1 SQAINHDHICKHLX-UHFFFAOYSA-N 0.000 claims description 2
- 230000004927 fusion Effects 0.000 claims 1
- 238000001459 lithography Methods 0.000 abstract description 27
- 238000001312 dry etching Methods 0.000 abstract description 20
- 239000011248 coating agent Substances 0.000 abstract description 13
- 238000000576 coating method Methods 0.000 abstract description 13
- 239000010408 film Substances 0.000 description 163
- ARXJGSRGQADJSQ-UHFFFAOYSA-N 1-methoxypropan-2-ol Chemical compound COCC(C)O ARXJGSRGQADJSQ-UHFFFAOYSA-N 0.000 description 23
- 239000004094 surface-active agent Substances 0.000 description 19
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 18
- 229920002120 photoresistant polymer Polymers 0.000 description 17
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 16
- 229920000642 polymer Polymers 0.000 description 16
- 239000000243 solution Substances 0.000 description 15
- LLHKCFNBLRBOGN-UHFFFAOYSA-N propylene glycol methyl ether acetate Chemical compound COCC(C)OC(C)=O LLHKCFNBLRBOGN-UHFFFAOYSA-N 0.000 description 14
- 239000007789 gas Substances 0.000 description 13
- 239000000463 material Substances 0.000 description 13
- LZCLXQDLBQLTDK-UHFFFAOYSA-N ethyl 2-hydroxypropanoate Chemical compound CCOC(=O)C(C)O LZCLXQDLBQLTDK-UHFFFAOYSA-N 0.000 description 12
- 230000000052 comparative effect Effects 0.000 description 11
- 239000004793 Polystyrene Substances 0.000 description 10
- 229920002223 polystyrene Polymers 0.000 description 10
- 229910052710 silicon Inorganic materials 0.000 description 10
- 239000007787 solid Substances 0.000 description 10
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 9
- 229940098779 methanesulfonic acid Drugs 0.000 description 9
- 239000012299 nitrogen atmosphere Substances 0.000 description 9
- 239000010703 silicon Substances 0.000 description 9
- 239000003513 alkali Substances 0.000 description 7
- RCYFOPUXRMOLQM-UHFFFAOYSA-N pyrene-1-carbaldehyde Chemical compound C1=C2C(C=O)=CC=C(C=C3)C2=C2C3=CC=CC2=C1 RCYFOPUXRMOLQM-UHFFFAOYSA-N 0.000 description 7
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 238000011161 development Methods 0.000 description 6
- KJIFKLIQANRMOU-UHFFFAOYSA-N oxidanium;4-methylbenzenesulfonate Chemical compound O.CC1=CC=C(S(O)(=O)=O)C=C1 KJIFKLIQANRMOU-UHFFFAOYSA-N 0.000 description 6
- 238000009833 condensation Methods 0.000 description 5
- 238000004132 cross linking Methods 0.000 description 5
- 238000000354 decomposition reaction Methods 0.000 description 5
- 238000004090 dissolution Methods 0.000 description 5
- 238000000206 photolithography Methods 0.000 description 5
- 235000012431 wafers Nutrition 0.000 description 5
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 239000006096 absorbing agent Substances 0.000 description 4
- 125000003282 alkyl amino group Chemical group 0.000 description 4
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 4
- 239000003054 catalyst Substances 0.000 description 4
- 230000005494 condensation Effects 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- CATSNJVOTSVZJV-UHFFFAOYSA-N heptan-2-one Chemical compound CCCCCC(C)=O CATSNJVOTSVZJV-UHFFFAOYSA-N 0.000 description 4
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- 125000001424 substituent group Chemical group 0.000 description 4
- WGTYBPLFGIVFAS-UHFFFAOYSA-M tetramethylammonium hydroxide Chemical compound [OH-].C[N+](C)(C)C WGTYBPLFGIVFAS-UHFFFAOYSA-M 0.000 description 4
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- 125000006078 2-ethyl-3-butenyl group Chemical group 0.000 description 3
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 3
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 3
- MRABAEUHTLLEML-UHFFFAOYSA-N Butyl lactate Chemical compound CCCCOC(=O)C(C)O MRABAEUHTLLEML-UHFFFAOYSA-N 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 3
- 239000003377 acid catalyst Substances 0.000 description 3
- 239000002318 adhesion promoter Substances 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 239000011230 binding agent Substances 0.000 description 3
- 239000001191 butyl (2R)-2-hydroxypropanoate Substances 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- BHXIWUJLHYHGSJ-UHFFFAOYSA-N ethyl 3-ethoxypropanoate Chemical compound CCOCCC(=O)OCC BHXIWUJLHYHGSJ-UHFFFAOYSA-N 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 229940116333 ethyl lactate Drugs 0.000 description 3
- NBVXSUQYWXRMNV-UHFFFAOYSA-N fluoromethane Chemical compound FC NBVXSUQYWXRMNV-UHFFFAOYSA-N 0.000 description 3
- 229910052736 halogen Inorganic materials 0.000 description 3
- 150000002367 halogens Chemical class 0.000 description 3
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 3
- BDJSOPWXYLFTNW-UHFFFAOYSA-N methyl 3-methoxypropanoate Chemical compound COCCC(=O)OC BDJSOPWXYLFTNW-UHFFFAOYSA-N 0.000 description 3
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 3
- 239000000049 pigment Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- 150000003672 ureas Chemical class 0.000 description 3
- DLDWUFCUUXXYTB-UHFFFAOYSA-N (2-oxo-1,2-diphenylethyl) 4-methylbenzenesulfonate Chemical compound C1=CC(C)=CC=C1S(=O)(=O)OC(C=1C=CC=CC=1)C(=O)C1=CC=CC=C1 DLDWUFCUUXXYTB-UHFFFAOYSA-N 0.000 description 2
- YXIWHUQXZSMYRE-UHFFFAOYSA-N 1,3-benzothiazole-2-thiol Chemical class C1=CC=C2SC(S)=NC2=C1 YXIWHUQXZSMYRE-UHFFFAOYSA-N 0.000 description 2
- 125000006064 1,3-dimethyl-1-butenyl group Chemical group 0.000 description 2
- LIPRQQHINVWJCH-UHFFFAOYSA-N 1-ethoxypropan-2-yl acetate Chemical compound CCOCC(C)OC(C)=O LIPRQQHINVWJCH-UHFFFAOYSA-N 0.000 description 2
- DMFAHCVITRDZQB-UHFFFAOYSA-N 1-propoxypropan-2-yl acetate Chemical compound CCCOCC(C)OC(C)=O DMFAHCVITRDZQB-UHFFFAOYSA-N 0.000 description 2
- SVONRAPFKPVNKG-UHFFFAOYSA-N 2-ethoxyethyl acetate Chemical compound CCOCCOC(C)=O SVONRAPFKPVNKG-UHFFFAOYSA-N 0.000 description 2
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- 125000006022 2-methyl-2-propenyl group Chemical group 0.000 description 2
- OKVJCVWFVRATSG-UHFFFAOYSA-N 3-hydroxybenzyl alcohol Chemical compound OCC1=CC=CC(O)=C1 OKVJCVWFVRATSG-UHFFFAOYSA-N 0.000 description 2
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 2
- PCYGLFXKCBFGPC-UHFFFAOYSA-N 4-(hydroxymethyl)benzene-1,2-diol Chemical compound OCC1=CC=C(O)C(O)=C1 PCYGLFXKCBFGPC-UHFFFAOYSA-N 0.000 description 2
- WHKRHBLAJFYZKF-UHFFFAOYSA-N 5-(hydroxymethyl)-2-methoxyphenol Chemical compound COC1=CC=C(CO)C=C1O WHKRHBLAJFYZKF-UHFFFAOYSA-N 0.000 description 2
- NGYYFWGABVVEPL-UHFFFAOYSA-N 5-(hydroxymethyl)benzene-1,3-diol Chemical compound OCC1=CC(O)=CC(O)=C1 NGYYFWGABVVEPL-UHFFFAOYSA-N 0.000 description 2
- GZVHEAJQGPRDLQ-UHFFFAOYSA-N 6-phenyl-1,3,5-triazine-2,4-diamine Chemical class NC1=NC(N)=NC(C=2C=CC=CC=2)=N1 GZVHEAJQGPRDLQ-UHFFFAOYSA-N 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- KCXZNSGUUQJJTR-UHFFFAOYSA-N Di-n-hexyl phthalate Chemical compound CCCCCCOC(=O)C1=CC=CC=C1C(=O)OCCCCCC KCXZNSGUUQJJTR-UHFFFAOYSA-N 0.000 description 2
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 2
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- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical group C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
- 229920001214 Polysorbate 60 Polymers 0.000 description 2
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 2
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- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 239000004115 Sodium Silicate Substances 0.000 description 2
- 239000004147 Sorbitan trioleate Substances 0.000 description 2
- PRXRUNOAOLTIEF-ADSICKODSA-N Sorbitan trioleate Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OC[C@@H](OC(=O)CCCCCCC\C=C/CCCCCCCC)[C@H]1OC[C@H](O)[C@H]1OC(=O)CCCCCCC\C=C/CCCCCCCC PRXRUNOAOLTIEF-ADSICKODSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
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- 238000007259 addition reaction Methods 0.000 description 2
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- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 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
- IJOOHPMOJXWVHK-UHFFFAOYSA-N chlorotrimethylsilane Chemical compound C[Si](C)(C)Cl IJOOHPMOJXWVHK-UHFFFAOYSA-N 0.000 description 2
- OEYIOHPDSNJKLS-UHFFFAOYSA-N choline Chemical compound C[N+](C)(C)CCO OEYIOHPDSNJKLS-UHFFFAOYSA-N 0.000 description 2
- 229960001231 choline Drugs 0.000 description 2
- 238000006482 condensation reaction Methods 0.000 description 2
- BGTOWKSIORTVQH-UHFFFAOYSA-N cyclopentanone Chemical compound O=C1CCCC1 BGTOWKSIORTVQH-UHFFFAOYSA-N 0.000 description 2
- JQVDAXLFBXTEQA-UHFFFAOYSA-N dibutylamine Chemical compound CCCCNCCCC JQVDAXLFBXTEQA-UHFFFAOYSA-N 0.000 description 2
- 235000014113 dietary fatty acids Nutrition 0.000 description 2
- FLKPEMZONWLCSK-UHFFFAOYSA-N diethyl phthalate Chemical compound CCOC(=O)C1=CC=CC=C1C(=O)OCC FLKPEMZONWLCSK-UHFFFAOYSA-N 0.000 description 2
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 2
- MGWAVDBGNNKXQV-UHFFFAOYSA-N diisobutyl phthalate Chemical compound CC(C)COC(=O)C1=CC=CC=C1C(=O)OCC(C)C MGWAVDBGNNKXQV-UHFFFAOYSA-N 0.000 description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical group C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- CKSRFHWWBKRUKA-UHFFFAOYSA-N ethyl 2-ethoxyacetate Chemical compound CCOCC(=O)OCC CKSRFHWWBKRUKA-UHFFFAOYSA-N 0.000 description 2
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- 239000000194 fatty acid Substances 0.000 description 2
- 229930195729 fatty acid Natural products 0.000 description 2
- 238000010304 firing Methods 0.000 description 2
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- BPSIOYPQMFLKFR-UHFFFAOYSA-N trimethoxy-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CO[Si](OC)(OC)CCCOCC1CO1 BPSIOYPQMFLKFR-UHFFFAOYSA-N 0.000 description 1
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- WLOQLWBIJZDHET-UHFFFAOYSA-N triphenylsulfonium Chemical class C1=CC=CC=C1[S+](C=1C=CC=CC=1)C1=CC=CC=C1 WLOQLWBIJZDHET-UHFFFAOYSA-N 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
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Abstract
本发明的课题是提供一种光刻用抗蚀剂下层膜,其为了呈现良好的涂布成膜性而在抗蚀剂溶剂(光刻中使用的溶剂)中具有高溶解性,且具有比抗蚀剂小的干蚀刻速度选择比。本课题的解决方法是一种包含酚醛清漆树脂的抗蚀剂下层膜形成用组合物,所述酚醛清漆树脂含有通过芳香族化合物(A)的芳香环与含羟基的芳香族羟甲基化合物(B)反应而得到的结构体(C)。芳香族化合物(A)是用于构成酚醛清漆树脂中包含的结构体(C)的成分。含羟基的芳香族羟甲基化合物(B)用式(1)表示。含羟基的芳香族羟甲基化合物(B)为2‑羟基苄醇、4‑羟基苄醇、或2,6‑二叔丁基‑4‑羟基甲基苯酚。
Description
技术领域
本发明涉及在进行半导体基板加工时有效的光刻用抗蚀剂下层膜形成用组合物、以及使用该抗蚀剂下层膜形成用组合物的抗蚀剂图案的形成方法、以及半导体装置的制造方法。
背景技术
一直以来,在半导体装置的制造中,通过使用光致抗蚀剂组合物的光刻来进行微细加工。上述微细加工是下述那样的加工法:在硅晶片等被加工基板上形成光致抗蚀剂组合物的薄膜,在其上经由描绘有半导体装置图案的掩模图案而照射紫外线等活性光线,进行显影,将得到的光致抗蚀剂图案作为保护膜,对硅晶片等被加工基板进行蚀刻处理。但是,近年来,半导体装置的高集成度化推进,使用的活性光线也从KrF准分子激光(248nm)向ArF准分子激光(193nm)逐渐短波长化。与此相伴,活性光线在基板上产生的漫反射、驻波的影响成为大问题,在光致抗蚀剂和被加工基板之间设置防反射膜(底部抗反射涂层(BottomAnti-Reflective Coating),BARC)的方法得到了广泛应用。另外,出于进一步微细加工的目的,人们也在进行着将极紫外线(EUV,13.5nm)和/或电子束(EB)用于活性光线的光刻技术开发。虽然对于EUV光刻、EB光刻来说,一般在基板上并不产生漫反射及驻波,因此不需要特定的防反射膜,但是作为目的在于改善抗蚀剂图案的分辨率、密合性的辅助膜,抗蚀剂下层膜开始被广泛地研究。
另一方面,随着抗蚀剂图案微细化的推进,抗蚀剂的薄膜化就变得必不可少。这是因为微细化导致分辨率下降、所形成的抗蚀剂图案变得容易倒塌。因此,维持基板加工所必需的抗蚀剂图案膜厚变得困难,不仅是抗蚀剂图案,对于在抗蚀剂和加工的半导体基板之间制成的抗蚀剂下层膜,也需要使其具备作为基板加工时掩模的功能。以这样的抗蚀剂膜厚的薄膜化为目的,形成至少2层抗蚀剂下层膜,并使用该抗蚀剂下层膜作为蚀刻掩模的光刻工艺被使用。对于这样的薄膜抗蚀剂而言,采用下述工艺:利用蚀刻工艺将抗蚀剂图案转印到其下层膜上,将该下层膜作为掩模进行基板加工的工艺;或者利用蚀刻工艺将抗蚀剂图案转印到其下层膜上,再使用不同的蚀刻气体将转印到下层膜上的图案转印到其下层膜上,重复进行这样的工序,最终进行基板加工的工艺。作为光刻工艺用抗蚀剂下层膜,要求对于干蚀刻工序中的蚀刻气体(例如碳氟化合物)具有高耐蚀刻性等。
作为上述抗蚀剂下层膜用聚合物,例示出以下的聚合物。
公开了使用聚羟甲基咔唑的抗蚀剂下层膜形成用组合物(参照专利文献1、专利文献2、和专利文献3)。
公开了使用芴苯酚酚醛清漆树脂的抗蚀剂下层膜形成用组合物(参照专利文献4)。
公开了使用芴萘酚酚醛清漆树脂的抗蚀剂下层膜形成用组合物(参照专利文献5)。
公开了含有以芴苯酚和芳基亚烷基作为重复单元的树脂的抗蚀剂下层膜形成用组合物(参照专利文献6和专利文献7)。
公开了使用咔唑酚醛清漆树脂的抗蚀剂下层膜形成用组合物(参照专利文献8)。
公开了使用多核苯酚酚醛清漆树脂的抗蚀剂下层膜形成用组合物(参照专利文献9)。
现有技术文献
专利文献
专利文献1:日本特开平2-293850号公报
专利文献2:日本特开平1-154050号公报
专利文献3:日本特开平2-22657号公报
专利文献4:日本特开2005-128509号公报
专利文献5:日本特开2007-199653号公报
专利文献6:日本特开2007-178974号公报
专利文献7:美国专利第7378217号说明书
专利文献8:国际公开小册子WO2010/147155号
专利文献9:日本特开2006-259249号公报
发明内容
发明所要解决的问题
对于上述抗蚀剂下层膜形成用组合物,从生产性、经济性的观点考虑,也期望与抗蚀剂组合物同样地使用旋转器涂布在硅晶片上并进行成膜。但是,对于这样的涂布型抗蚀剂下层膜形成用组合物而言,为了实现良好的涂布性,需要使作为抗蚀剂下层膜形成用组合物的主要成分的聚合物树脂、交联剂、交联催化剂等溶解在适当的溶剂中。作为这样的溶剂,可以列举被用于抗蚀剂形成用组合物的丙二醇单甲基醚(PGME)或丙二醇单甲基醚乙酸酯(PGMEA)、环己酮等作为代表性溶剂,抗蚀剂下层膜形成用组合物需要在这些溶剂中有良好的溶解性。
本发明是基于解决这样的问题而做出的,其目的在于提供,为了呈现良好的涂布成膜性而在抗蚀剂溶剂(用于光刻的溶剂)中具有高溶解性且具有与抗蚀剂相比小的干蚀刻速度的选择比的光刻用抗蚀剂下层膜形成用组合物。另外,本发明的目的在于提供,使用该抗蚀剂下层膜形成用组合物的抗蚀剂图案形成方法,以及半导体装置的制造方法。
用于解决问题的方法
关于本发明,作为第1观点,是一种抗蚀剂下层膜形成用组合物,包含酚醛清漆树脂,所述酚醛清漆树脂含有通过芳香族化合物(A)的芳香环与含羟基的芳香族羟甲基化合物(B)的反应而得到的结构体(C),
作为第2观点,是根据第1观点所述的抗蚀剂下层膜形成用组合物,上述芳香族化合物(A)是用于构成酚醛清漆树脂中所包含的结构体(C)的成分,
作为第3观点,是根据第1观点或第2观点所述的抗蚀剂下层膜形成用组合物,上述含羟基的芳香族羟甲基化合物(B)是式(1)所示的化合物,
(式(1)中,Ar1表示碳原子数为6~40的芳基;R1表示碳原子数为1~10的烷基、碳原子数为2~10的烯基、碳原子数为2~10的炔基、碳原子数为6~40的芳基、羟基、氰基、硝基、氨基、羧基、乙酰基、卤代甲基、-Y-Z基、卤素原子、或它们的组合。Y表示氧原子、硫原子、羰基、或酯基,Z表示碳原子数为1~10的烷基。R2表示氢原子或甲基。R3、R4分别表示氢原子、碳原子数为1~10的烷基、碳原子数为2~10的烯基、氰基、或烷基氨基。m为0~(4+2n)的整数,n表示芳基Ar1具有的苯环的稠合度),
作为第4观点,是根据第1观点~第3观点中任一项所述的抗蚀剂下层膜形成用组合物,上述含羟基的芳香族羟甲基化合物(B)为2-羟基苄醇、4-羟基苄醇、或2,6-二叔丁基-4-羟基甲基苯酚,
作为第5观点,是根据第1观点~第4观点中任一项所述的抗蚀剂下层膜形成用组合物,上述结构体(C)具有式(2)所示的结构,
(式(2)中,Ar1、R1、R3、R4和m分别与式(1)中的Ar1、R1、R3、R4和m相同,A1为芳香族化合物(A)的芳香环或酚醛清漆树脂的芳香环),
作为第6观点,是根据第1观点~第5观点中任一项所述的抗蚀剂下层膜形成用组合物,上述芳香族化合物(A)为芳香族胺或含有酚性羟基的化合物,
作为第7观点,是根据第1观点~第6观点中任一项所述的抗蚀剂下层膜形成用组合物,上述酚醛清漆树脂是通过芳香族胺或含有酚性羟基的化合物、与醛或酮反应而生成的树脂,
作为第8观点,是根据第7观点所述的抗蚀剂下层膜形成用组合物,上述芳香族胺为苯基吲哚或苯基萘胺,
作为第9观点,是根据第7观点所述的抗蚀剂下层膜形成用组合物,上述含有酚性羟基的化合物为苯酚、二羟基苯、三羟基苯、羟基萘、二羟基萘、三羟基萘、三(4-羟基苯基)甲烷、三(4-羟基苯基)乙烷、或1,1,2,2-四(4-羟基苯基)乙烷,
作为第10观点,是根据第7观点~第9观点中任一项所述的抗蚀剂下层膜形成用组合物,上述醛为萘甲醛或芘甲醛,
作为第11观点,是根据第1观点~第10观点中任一项所述的抗蚀剂下层膜形成用组合物,其中还含有溶剂,
作为第12观点,是根据第1观点~第11观点中任一项所述的抗蚀剂下层膜形成用组合物,其中还含有酸和/或产酸剂,
作为第13观点,是根据第1观点~第12观点中任一项所述的抗蚀剂下层膜形成用组合物,其中还含有交联剂,
作为第14观点,是一种在半导体制造中使用的抗蚀剂图案的形成方法,其中包含下述工序:将第1观点~第13观点中任一项所述的抗蚀剂下层膜形成用组合物涂布在半导体基板上,进行烘烤从而形成下层膜,
作为第15观点,是一种半导体装置的制造方法,其中包含下述工序:利用第1观点~第13观点中任一项所述的抗蚀剂下层膜形成用组合物在半导体基板上形成下层膜的工序,在该下层膜上形成抗蚀剂膜的工序,通过照射光或电子束并且显影而形成抗蚀剂图案的工序,利用该抗蚀剂图案对该下层膜进行蚀刻的工序,以及利用图案化了的下层膜来加工半导体基板的工序,
作为第16观点,是一种半导体装置的制造方法,其中包含下述工序:利用第1观点~第13观点中任一项所述的抗蚀剂下层膜形成用组合物在半导体基板上形成下层膜的工序,在该下层膜上形成硬掩模的工序,进而在该硬掩模上形成抗蚀剂膜的工序,通过照射光或电子束并且显影而形成抗蚀剂图案的工序,利用该抗蚀剂图案对硬掩模进行蚀刻的工序,利用图案化了的硬掩模对该下层膜进行蚀刻的工序,以及利用图案化了的下层膜来加工半导体基板的工序,
作为第17观点,是根据第16观点所述的制造方法,上述硬掩模由无机物蒸镀膜形成。
发明效果
本发明的抗蚀剂下层膜形成用组合物对于以上述抗蚀剂膜厚的薄膜化为目的的、形成至少2层抗蚀剂下层膜、使用该抗蚀剂下层膜作为蚀刻掩模的光刻工艺是有效的,其不仅对像碳氟化合物(fluorocarbon)这样的蚀刻气体具有高的耐干蚀刻性,而且在使用本发明的抗蚀剂下层膜加工基板时,对加工基板(例如,基板上的热氧化硅膜、氮化硅膜、多晶硅膜等)也有充分的耐蚀刻性。
特别地,本发明的抗蚀剂下层膜形成用组合物是在抗蚀剂溶剂中的溶解性高、旋涂性优异的涂布型组合物。而且,由本发明的抗蚀剂下层膜形成用组合物得到的抗蚀剂下层膜在形成被膜并进行烘烤后,在那些抗蚀剂溶剂中不会再溶解。
具体实施方式
本发明是一种包含酚醛清漆树脂的抗蚀剂下层膜形成用组合物,所述酚醛清漆树脂含有通过芳香族化合物(A)的芳香环与含羟基的芳香族羟甲基化合物(B)反应而得到的结构体(C)。
在本发明中,上述光刻用抗蚀剂下层膜形成用组合物包含上述树脂和溶剂。而且,根据需要可包含交联剂、酸、产酸剂、表面活性剂等。
该组合物的固体成分为0.1~70质量%、或0.1~60质量%。固体成分是从抗蚀剂下层膜形成用组合物中除去溶剂后的全部成分的含有比例。在固体成分中,可以按1~100质量%、或1~99.9质量%、或50~99.9质量%、或50~95质量%、或50~90质量%的比例含有上述聚合物。
对于本发明中使用的聚合物(树脂),其重均分子量为600~1000000,或600~200000。
含羟基的芳香族羟甲基化合物(B)可以例示具有式(1)结构的、含有羟甲基、或甲氧基甲基的化合物。
式(1)中,Ar1表示碳原子数为6~40的芳基,R1表示碳原子数为1~10的烷基、碳原子数为2~10的烯基、碳原子数为2~10的炔基、碳原子数为6~40的芳基、羟基、氰基、硝基、氨基、羧基、乙酰基、卤代甲基、-Y-Z基、卤素原子、或它们的组合。Y表示氧原子、硫原子、羰基、酯基,Z表示碳原子数为1~10的烷基。R2表示氢原子或甲基。R3、R4分别表示氢原子、碳原子数为1~10的烷基、碳原子数为2~10的烯基、氰基、或烷基氨基。m为0~(4+2n)的整数,n表示芳基Ar1具有的苯环的稠合度。
上述烷基是碳原子数为1~10的烷基,可以列举例如甲基、乙基、正丙基、异丙基、环丙基、正丁基、异丁基、仲丁基、叔丁基、环丁基、1-甲基-环丙基、2-甲基-环丙基、正戊基、1-甲基-正丁基、2-甲基-正丁基、3-甲基-正丁基、1,1-二甲基-正丙基、1,2-二甲基-正丙基、2,2-二甲基-正丙基、1-乙基-正丙基、环戊基、1-甲基-环丁基、2-甲基-环丁基、3-甲基-环丁基、1,2-二甲基-环丙基、2,3-二甲基-环丙基、1-乙基-环丙基、2-乙基-环丙基、正己基、1-甲基-正戊基、2-甲基-正戊基、3-甲基-正戊基、4-甲基-正戊基、1,1-二甲基-正丁基、1,2-二甲基-正丁基、1,3-二甲基-正丁基、2,2-二甲基-正丁基、2,3-二甲基-正丁基、3,3-二甲基-正丁基、1-乙基-正丁基、2-乙基-正丁基、1,1,2-三甲基-正丙基、1,2,2-三甲基-正丙基、1-乙基-1-甲基-正丙基、1-乙基-2-甲基-正丙基、环己基、1-甲基-环戊基、2-甲基-环戊基、3-甲基-环戊基、1-乙基-环丁基、2-乙基-环丁基、3-乙基-环丁基、1,2-二甲基-环丁基、1,3-二甲基-环丁基、2,2-二甲基-环丁基、2,3-二甲基-环丁基、2,4-二甲基-环丁基、3,3-二甲基-环丁基、1-正丙基-环丙基、2-正丙基-环丙基、1-异丙基-环丙基、2-异丙基-环丙基、1,2,2-三甲基-环丙基、1,2,3-三甲基-环丙基、2,2,3-三甲基-环丙基、1-乙基-2-甲基-环丙基、2-乙基-1-甲基-环丙基、2-乙基-2-甲基-环丙基以及2-乙基-3-甲基-环丙基等。
上述芳基是碳原子数为6~40的芳基,可以列举例如苯基、邻甲基苯基、间甲基苯基、对甲基苯基、邻氯苯基、间氯苯基、对氯苯基、邻氟苯基、对氟苯基、邻甲氧基苯基、对甲氧基苯基、对硝基苯基、对氰基苯基、α-萘基、β-萘基、邻联苯基、间联苯基、对联苯基、1-蒽基、2-蒽基、9-蒽基、1-菲基、2-菲基、3-菲基、4-菲基以及9-菲基。
上述烯基是碳原子数为2~10的烯基,可以列举例如乙烯基、1-丙烯基、2-丙烯基、1-甲基-1-乙烯基、1-丁烯基、2-丁烯基、3-丁烯基、2-甲基-1-丙烯基、2-甲基-2-丙烯基、1-乙基乙烯基、1-甲基-1-丙烯基、1-甲基-2-丙烯基、1-戊烯基、2-戊烯基、3-戊烯基、4-戊烯基、1-正丙基乙烯基、1-甲基-1-丁烯基、1-甲基-2-丁烯基、1-甲基-3-丁烯基、2-乙基-2-丙烯基、2-甲基-1-丁烯基、2-甲基-2-丁烯基、2-甲基-3-丁烯基、3-甲基-1-丁烯基、3-甲基-2-丁烯基、3-甲基-3-丁烯基、1,1-二甲基-2-丙烯基、1-异丙基乙烯基、1,2-二甲基-1-丙烯基、1,2-二甲基-2-丙烯基、1-环戊烯基、2-环戊烯基、3-环戊烯基、1-己烯基、2-己烯基、3-己烯基、4-己烯基、5-己烯基、1-甲基-1-戊烯基、1-甲基-2-戊烯基、1-甲基-3-戊烯基、1-甲基-4-戊烯基、1-正丁基乙烯基、2-甲基-1-戊烯基、2-甲基-2-戊烯基、2-甲基-3-戊烯基、2-甲基-4-戊烯基、2-正丙基-2-丙烯基、3-甲基-1-戊烯基、3-甲基-2-戊烯基、3-甲基-3-戊烯基、3-甲基-4-戊烯基、3-乙基-3-丁烯基、4-甲基-1-戊烯基、4-甲基-2-戊烯基、4-甲基-3-戊烯基、4-甲基-4-戊烯基、1,1-二甲基-2-丁烯基、1,1-二甲基-3-丁烯基、1,2-二甲基-1-丁烯基、1,2-二甲基-2-丁烯基、1,2-二甲基-3-丁烯基、1-甲基-2-乙基-2-丙烯基、1-仲丁基乙烯基、1,3-二甲基-1-丁烯基、1,3-二甲基-2-丁烯基、1,3-二甲基-3-丁烯基、1-异丁基乙烯基、2,2-二甲基-3-丁烯基、2,3-二甲基-1-丁烯基、2,3-二甲基-2-丁烯基、2,3-二甲基-3-丁烯基、2-异丙基-2-丙烯基、3,3-二甲基-1-丁烯基、1-乙基-1-丁烯基、1-乙基-2-丁烯基、1-乙基-3-丁烯基、1-正丙基-1-丙烯基、1-正丙基-2-丙烯基、2-乙基-1-丁烯基、2-乙基-2-丁烯基、2-乙基-3-丁烯基、1,1,2-三甲基-2-丙烯基、1-叔丁基乙烯基、1-甲基-1-乙基-2-丙烯基、1-乙基-2-甲基-1-丙烯基、1-乙基-2-甲基-2-丙烯基、1-异丙基-1-丙烯基、1-异丙基-2-丙烯基、1-甲基-2-环戊烯基、1-甲基-3-环戊烯基、2-甲基-1-环戊烯基、2-甲基-2-环戊烯基、2-甲基-3-环戊烯基、2-甲基-4-环戊烯基、2-甲基-5-环戊烯基、2-亚甲基-环戊基、3-甲基-1-环戊烯基、3-甲基-2-环戊烯基、3-甲基-3-环戊烯基、3-甲基-4-环戊烯基、3-甲基-5-环戊烯基、3-亚甲基-环戊基、1-环己烯基、2-环己烯基以及3-环己烯基等。
作为上述炔基,可以列举例如乙炔基、炔丙基等。
在上述-Y-Z基中,Y表示氧原子、硫原子、羰基、酯基,Z表示碳原子数为1~10的烷基。
作为上述烷基氨基,可以列举例如甲基氨基、乙基氨基、正丙基氨基、异丙基氨基、环丙基氨基、正丁基氨基、异丁基氨基、仲丁基氨基、叔丁基氨基、环丁基氨基、1-甲基-环丙基氨基、2-甲基-环丙基氨基、正戊基氨基、1-甲基-正丁基氨基、2-甲基-正丁基氨基、3-甲基-正丁基氨基、1,1-二甲基-正丙基氨基等。
具有式(1)结构的含羟基的芳香族羟甲基化合物(B)可以进行以下示例。
含羟基的芳香族羟甲基化合物(B)优选为2-羟基苄醇、3-羟基苄醇、4-羟基苄醇、2,6-二叔丁基-4-羟基甲基苯酚、3-羟基-4-甲氧基苄醇、4-羟基-3-甲氧基苄醇、4-羟基-3-甲氧基-α-甲基苄醇、3-羟基-α-甲基苄醇、2-羟基-3-甲氧基苄醇、5-溴-2-羟基苄醇、DL-4-羟基苯乙醇腈、脱氧肾上腺素、(4-羟基苯基)二苯基甲醇、3,4-二羟基苄醇、3,5-二羟基苄醇。
含有芳香环的芳香族化合物(A)可以例示芳香族胺、和含有酚性羟基的化合物。
作为芳香族胺,优选碳原子数为6~40的胺,可以例示例如苯胺、萘胺、苯基萘胺、苯基吲哚、以及咔唑。可以优选使用苯基萘胺、和苯基吲哚。
作为含有酚性羟基的化合物,可以列举碳原子数为6~40的化合物,可以例示例如苯酚、二羟基苯、三羟基苯、羟基萘、二羟基萘、或三羟基萘、三(4-羟基苯基)甲烷、三(4-羟基苯基)乙烷、1,1,2,2-四(4-羟基苯基)乙烷。
通过芳香族化合物(A)的芳香环与含羟基的芳香族羟甲基化合物(B)的反应而得到的结构体(C)可以列举具有式(2)结构的树脂。
式(2)中,Ar1、R1、R2、m分别与式(1)中的Ar1、R1、R2、m相同,A1是芳香族化合物(A)的芳香环或酚醛清漆树脂的芳香环。
即,Ar1表示碳原子数为6~40的芳基,R1表示碳原子数为1~10的烷基、碳原子数为2~10的烯基、碳原子数为2~10的炔基、碳原子数为6~40的芳基、羟基、氰基、硝基、氨基、羧基、乙酰基、卤代甲基、-Y-Z基、卤素原子、或它们的组合。Y表示氧原子、硫原子、羰基、酯基,Z表示碳原子数为1~10的烷基。R2表示氢原子或甲基。R3、R4分别表示氢原子、碳原子数为1~10的烷基、碳原子数为2~10的烯基、氰基、或烷基氨基。m为0~(4+2n)的整数,n表示芳基Ar1具有的苯环的稠合度。
对于含有芳香环的芳香族化合物(A)与含羟基的芳香族羟甲基化合物(B)的反应,优选使上述(A)和上述(B)按1:0.1~8.0,或1:0.1~4.0的摩尔比进行反应。
芳香族化合物(A)是用于构成酚醛清漆树脂中所包含的结构体(C)的成分。芳香族化合物(A)可以为芳香族胺或含有酚性羟基的化合物。
芳香族胺可以列举苯基吲哚、苯基萘胺等。
含有酚性羟基的化合物可以列举苯酚、二羟基苯、三羟基苯、羟基萘、二羟基萘、三羟基萘、三(4-羟基苯基)甲烷、三(4-羟基苯基)乙烷、1,1,2,2-四(4-羟基苯基)乙烷等。
上述酚醛清漆树脂由能够与含有芳香环的芳香族化合物(A)反应的任意醛或酮类得到。
作为醛或酮类,可以列举碳原子数为6~40的化合物,可以例示例如苯甲醛、萘甲醛、苯基苯甲醛、以及芘甲醛,优选列举出萘甲醛、芘甲醛。
酚醛清漆化的缩合反应和含羟基的芳香族羟甲基化合物(B)的加成反应同时进行,作为在这些反应中使用的酸催化剂,可以使用例如硫酸、磷酸、高氯酸等无机酸类,对甲苯磺酸、对甲苯磺酸一水合物、甲磺酸等有机磺酸类,甲酸、草酸等羧酸类。酸催化剂的使用量可根据所使用的酸类的种类进行各种选择。通常,相对于含有芳香环的芳香族化合物(A)100质量份为0.001~10000质量份,优选为0.01~1000质量份,更优选为0.1~100质量份。
虽然上述缩合反应和加成反应可以在无溶剂情况下进行,但通常使用溶剂进行。作为溶剂,只要是不阻碍反应的溶剂就都可以使用。可以列举例如1,2-二甲氧基乙烷、二乙二醇二甲基醚、丙二醇单甲基醚、四氢呋喃、二烷等醚类。另外,如果所使用的酸催化剂是例如甲酸这样的液态催化剂,则也能够使其兼具溶剂的作用。
缩合时的反应温度通常为40℃~200℃。反应时间可根据反应温度进行各种选择,但通常为30分钟~50小时左右。
按如上的方式得到的聚合物的重均分子量Mw通常为500~1000000,或600~200000。
通过含有芳香环的芳香族化合物(A)与含羟基的芳香族羟甲基化合物(B)的反应而得到结构体(C),作为含有该结构体(C)的酚醛清漆树脂的代表性的例子,可以为下述所示。
本发明的抗蚀剂下层膜形成用组合物可以含有交联剂成分。作为该交联剂,可以列举三聚氰胺系、取代脲系、或它们的聚合物系等。优选是具有至少2个交联形成取代基的交联剂,是甲氧基甲基化甘脲、丁氧基甲基化甘脲、甲氧基甲基化三聚氰胺、丁氧基甲基化三聚氰胺、甲氧基甲基化苯胍胺、丁氧基甲基化苯胍胺、甲氧基甲基化脲、丁氧基甲基化脲、或甲氧基甲基化硫脲等化合物。另外,也可以使用这些化合物的缩合物。
另外,作为上述交联剂,可以使用耐热性高的交联剂。作为耐热性高的交联剂,可以优选使用分子内具有芳香环(例如,苯环、萘环)的、含有交联形成取代基的化合物。
该化合物可以列举具有下述式(4)所示的部分结构的化合物、或具有下述式(5)所示的重复单元的聚合物或低聚物。
上述R11、R12、R13、和R14是氢原子或碳原子数为1~10的烷基,这些烷基可以使用上述的示例。
式(4)及式(5)所示的化合物、聚合物、低聚物如下例示。
上述化合物可以以旭有机材工业(株)、本州化学工业(株)的产品的形式获得。例如在上述交联剂中,式(4-24)的化合物可以以旭有机材工业(株),商品名为TM-BIP-A的形式获得。
交联剂的添加量随着使用的涂布溶剂、使用的底层基板、要求的溶液粘度、要求的膜形状等变化而变化,但是相对于全部固体成分为0.001~80质量%,优选为0.01~50质量%,更优选为0.05~40质量%。虽然这些交联剂有时通过自缩合引起交联反应,但是在本发明的上述的聚合物中存在交联性取代基的情况下,可以与那些交联性取代基发生交联反应。
在本发明中,可以添加作为用于促进上述交联反应的催化剂的酸和/或产酸剂。例如,可以配合对甲苯磺酸、三氟甲烷磺酸、对甲苯磺酸吡啶水杨酸、5-磺基水杨酸、4-苯酚磺酸、樟脑磺酸、4-氯苯磺酸、苯二磺酸、1-萘磺酸、柠檬酸、苯甲酸、羟基苯甲酸、萘甲酸等酸性化合物、和/或2,4,4,6-四溴环己二烯酮、苯偶姻甲苯磺酸酯、甲苯磺酸2-硝基苄酯、其他有机磺酸烷基酯等热产酸剂。配合量相对于全部固体成分为0.0001~20质量%,优选为0.0005~10质量%,更优选为0.01~3质量%。
对于本发明的光刻用抗蚀剂下层膜形成用组合物而言,为了在光刻工序中使其与被覆于上层的光致抗蚀剂的酸度一致,可以添加光产酸剂。作为优选的光产酸剂,可以列举例如双(4-叔丁基苯基)碘三氟甲磺酸盐,三苯基锍三氟甲磺酸盐等盐系光产酸剂类,苯基-双(三氯甲基)-均三嗪等含卤素化合物系光产酸剂类,苯偶姻甲苯磺酸酯、N-羟基琥珀酰亚胺三氟甲磺酸酯等磺酸系光产酸剂类等。上述光产酸剂相对于全部固体成分为0.2~10质量%,优选为0.4~5质量%。
在本发明的光刻用抗蚀剂下层膜材料中,除上述之外,可以根据需要进一步添加吸光剂、流变调节剂、粘接助剂、表面活性剂等。
作为进一步的吸光剂,优选使用例如,“工业用色素的技术和市场”(CMC出版)、“染料便览”(有机合成化学协会编)中记载的市售吸光剂,例如,C.I.分散黄1、3、4、5、7、8、13、23、31、49、50、51、54、60、64、66、68、79、82、88、90、93、102、114及124;C.I.分散橙1、5、13、25、29、30、31、44、57、72及73;C.I.分散红1、5、7、13、17、19、43、50、54、58、65、72、73、88、117、137、143、199及210;C.I.分散紫43;C.I.分散蓝96;C.I.荧光增白剂112、135及163;C.I.溶剂橙2及45;C.I.溶剂红1、3、8、23、24、25、27及49;C.I.颜料绿10;C.I.颜料棕2等。上述吸光剂通常按相对于光刻用抗蚀剂下层膜材料的全部固体成分为10质量%以下,优选为5质量%以下的比例进行配合。
添加流变调节剂的目的主要是提高抗蚀剂下层膜形成用组合物的流动性,特别是在烘烤工序中,提高抗蚀剂下层膜的膜厚均匀性和/或提高抗蚀剂下层膜形成用组合物对孔内部的填充性。作为具体例子,可以列举苯二甲酸二甲酯、苯二甲酸二乙酯、苯二甲酸二异丁酯、苯二甲酸二己酯、苯二甲酸丁基异癸酯等苯二甲酸衍生物,己二酸二正丁酯、己二酸二异丁酯、己二酸二异辛酯、己二酸辛基癸酯等己二酸衍生物,马来酸二正丁酯,马来酸二乙酯,马来酸二壬酯等马来酸衍生物,油酸甲酯、油酸丁酯、油酸四氢糠酯等油酸衍生物,或硬脂酸正丁酯、硬脂酸缩水甘油酯等硬脂酸衍生物。这些流变调节剂通常按相对于光刻用抗蚀剂下层膜材料的全部固体成分为小于30质量%的比例进行配合。
添加粘接助剂的目的主要是为了提高基板或抗蚀剂与抗蚀剂下层膜形成用组合物的密合性,特别是为了使抗蚀剂在显影时不剥离。作为具体例子,可以列举三甲基氯硅烷、二甲基羟甲基氯硅烷、甲基二苯基氯硅烷、氯甲基二甲基氯硅烷等氯硅烷类,三甲基甲氧基硅烷、二甲基二乙氧基硅烷、甲基二甲氧基硅烷、二甲基羟甲基乙氧基硅烷、二苯基二甲氧基硅烷、苯基三乙氧基硅烷等烷氧基硅烷类,六甲基二硅氮烷、N,N’-双(三甲基甲硅烷基)脲、二甲基三甲基甲硅烷基胺、三甲基甲硅烷基咪唑等硅氮烷类,羟甲基三氯硅烷、γ-氯丙基三甲氧基硅烷、γ-氨基丙基三乙氧基硅烷、γ-环氧丙氧基丙基三甲氧基硅烷等硅烷类,苯并***、苯并咪唑、吲唑、咪唑、2-巯基苯并咪唑、2-巯基苯并噻唑、2-巯基苯并唑、尿唑、硫脲嘧啶、巯基咪唑、巯基嘧啶等杂环式化合物,1,1-二甲基脲、1,3-二甲基脲等脲、或硫脲化合物。这些粘接助剂通常按相对于光刻用抗蚀剂下层膜材料的全部固体成分为小于5质量%,优选为小于2质量%的比例进行配合。
在本发明的光刻用抗蚀剂下层膜材料中,为了不产生针孔及条纹等、进一步提高针对表面不平整的涂布性,可以配合表面活性剂。作为表面活性剂,可以列举例如聚氧乙烯月桂基醚、聚氧乙烯硬脂基醚、聚氧乙烯鲸蜡基醚、聚氧乙烯油基醚等聚氧乙烯烷基醚类,聚氧乙烯辛基苯酚醚、聚氧乙烯壬基苯酚醚等聚氧乙烯烷基芳基醚类,聚氧乙烯-聚氧丙烯嵌段共聚物类,脱水山梨糖醇单月桂酸酯、脱水山梨糖醇单棕榈酸酯、脱水山梨糖醇单硬脂酸酯、脱水山梨糖醇单油酸酯、脱水山梨糖醇三油酸酯、脱水山梨糖醇三硬脂酸酯等脱水山梨糖醇脂肪酸酯类,聚氧乙烯脱水山梨糖醇单月桂酸酯、聚氧乙烯脱水山梨糖醇单棕榈酸酯、聚氧乙烯脱水山梨糖醇单硬脂酸酯、聚氧乙烯脱水山梨糖醇三油酸酯、聚氧乙烯脱水山梨糖醇三硬脂酸酯等聚氧乙烯脱水山梨糖醇脂肪酸酯类等非离子系表面活性剂,エフトップEF301、EF303、EF352((株)トーケムプロダクツ制,商品名),メガファックF171、F173、R-40、R-40N、R-30N、R-40LM(DIC(株)制,商品名),フロラードFC430、FC431(住友スリーエム(株)制,商品名),アサヒガードAG710,サーフロンS-382、SC101、SC102、SC103、SC104、SC105、SC106(旭硝子(株)制,商品名)等氟系表面活性剂,有机硅氧烷聚合物KP341(信越化学工业(株)制)等。这些表面活性剂的配合量通常相对于本发明的光刻用抗蚀剂下层膜材料的全部固体成分为2.0质量%以下,优选为1.0质量%以下。这些表面活性剂可以单独添加,另外也可以添加2种以上的组合。
在本发明中,作为使上述聚合物及交联剂成分、交联催化剂等溶解的溶剂,可以使用乙二醇单甲基醚、乙二醇单乙基醚、甲基溶纤剂乙酸酯、乙基溶纤剂乙酸酯、二乙二醇单甲基醚、二乙二醇单乙基醚、丙二醇、丙二醇单甲基醚、丙二醇单甲基醚乙酸酯、丙二醇单乙基醚、丙二醇单乙基醚乙酸酯、丙二醇丙基醚乙酸酯、甲苯、二甲苯、甲基乙基酮、环戊酮、环己酮、2-羟基丙酸乙酯、2-羟基-2-甲基丙酸乙酯、乙氧基乙酸乙酯、羟基乙酸乙酯、2-羟基-3-甲基丁酸甲酯、3-甲氧基丙酸甲酯、3-甲氧基丙酸乙酯、3-乙氧基丙酸乙酯、3-乙氧基丙酸甲酯、丙酮酸甲酯、丙酮酸乙酯、乙酸乙酯、乙酸丁酯、乳酸乙酯、乳酸丁酯等。这些有机溶剂可单独使用,或组合2种以上使用。
进而,可以混合丙二醇单丁基醚、丙二醇单丁基醚乙酸酯等高沸点溶剂来使用。在这些溶剂中,丙二醇单甲基醚、丙二醇单甲基醚乙酸酯、乳酸乙酯、乳酸丁酯、以及环己酮等对于提高流平性是优选的。特别优选丙二醇单甲基醚、丙二醇单甲基醚乙酸酯。
本发明中使用的树脂在光刻工序中通常使用的丙二醇单甲基醚、丙二醇单甲基醚乙酸酯等溶剂中显示出高溶解性。
本发明中使用的抗蚀剂是光致抗蚀剂和/或电子束抗蚀剂。
作为本发明中涂布于光刻用抗蚀剂下层膜的上部的光致抗蚀剂,可以使用负型、正型中的任何一种,有由酚醛清漆树脂和1,2-二叠氮基萘醌磺酸酯构成的正型光致抗蚀剂、由具有通过酸进行分解而提高了碱溶解速度的基团的粘合剂和光产酸剂构成的化学增幅型光致抗蚀剂、由碱溶性粘合剂、通过酸进行分解而提高了光致抗蚀剂的碱溶解速度的低分子化合物和光产酸剂构成的化学增幅型光致抗蚀剂、由具有通过酸进行分解而提高了碱溶解速度的基团的粘合剂、通过酸进行分解而提高了光致抗蚀剂的碱溶解速度的低分子化合物和光产酸剂构成的化学增幅型光致抗蚀剂、骨架中具有Si原子的光致抗蚀剂等,可以列举例如,ロームアンドハース社制,商品名为APEX-E。
另外,作为本发明中涂布于光刻用抗蚀剂下层膜的上部的电子束抗蚀剂,可以列举例如包含主链含Si-Si键且末端含芳香族环的树脂和通过电子束的照射而产生酸的产酸剂的组合物、或包含羟基被含有N-羧基胺的有机基团取代了的聚(对羟基苯乙烯)和通过电子束的照射而产生酸的产酸剂的组合物等。在后者的电子束抗蚀剂组合物中,通过电子束照射而由产酸剂生成的酸与聚合物侧链的N-羧基氨氧基反应,聚合物侧链分解成羟基而显示出碱溶性并溶解在碱性显影液中,形成抗蚀剂图案。该通过电子束照射而产生酸的产酸剂可以列举1,1-双[对氯苯基]-2,2,2-三氯乙烷、1,1-双[对甲氧基苯基]-2,2,2-三氯乙烷、1,1-双[对氯苯基]-2,2-二氯乙烷、2-氯-6-(三氯甲基)吡啶等卤化有机化合物,三苯基锍盐、二苯基碘等盐,甲苯磺酸硝基苄酯、甲苯磺酸二硝基苄酯等磺酸酯。
作为具有使用本发明的光刻用抗蚀剂下层膜材料形成的抗蚀剂下层膜的抗蚀剂的显影液,可以使用氢氧化钠、氢氧化钾、碳酸钠、硅酸钠、偏硅酸钠、氨水等无机碱类,乙基胺、正丙基胺等伯胺类,二乙基胺、二正丁基胺等仲胺类,三乙基胺、甲基二乙基胺等叔胺类,二甲基乙醇胺、三乙醇胺等醇胺类,四甲基氢氧化铵、四乙基氢氧化铵、胆碱等季铵盐,吡咯、哌啶等环状胺类等碱类的水溶液。进而,也可以在上述碱类的水溶液中添加适当量的异丙醇等醇类、非离子系等表面活性剂来使用。其中优选的显影液是季铵盐,进一步优选四甲基氢氧化铵和胆碱。
另外,作为显影液,可以使用有机溶剂,可以列举例如,乙酸甲酯、乙酸乙酯、乙酸异丙酯、乙酸丁酯、乙酸戊酯、乙酸异戊酯、甲氧基乙酸乙酯、乙氧基乙酸乙酯、2-庚酮、丙二醇单甲基醚乙酸酯、乙二醇单乙基醚乙酸酯、乙二醇单丙基醚乙酸酯、乙二醇单丁基醚乙酸酯、乙二醇单苯基醚乙酸酯、二乙二醇单甲基醚乙酸酯、二乙二醇单乙基醚乙酸酯、二乙二醇单丙基醚乙酸酯、二乙二醇单丁基醚乙酸酯、二乙二醇单苯基醚乙酸酯、2-甲氧基丁基乙酸酯、3-甲氧基丁基乙酸酯、4-甲氧基丁基乙酸酯、3-甲基-3-甲氧基丁基乙酸酯、3-乙基-3-甲氧基丁基乙酸酯、丙二醇单甲基醚乙酸酯、丙二醇单乙基醚乙酸酯、丙二醇单丙基醚乙酸酯、2-乙氧基丁基乙酸酯、4-乙氧基丁基乙酸酯、4-丙氧基丁基乙酸酯、2-甲氧基戊基乙酸酯、3-甲氧基戊基乙酸酯、4-甲氧基戊基乙酸酯、2-甲基-3-甲氧基戊基乙酸酯、3-甲基-3-甲氧基戊基乙酸酯、3-甲基-4-甲氧基戊基乙酸酯、4-甲基-4-甲氧基戊基乙酸酯、丙二醇二乙酸酯、甲酸甲酯、甲酸乙酯、甲酸丁酯、甲酸丙酯、乳酸乙酯、乳酸丁酯、乳酸丙酯、碳酸乙酯、碳酸丙酯、碳酸丁酯、丙酮酸甲酯、丙酮酸乙酯、丙酮酸丙酯、丙酮酸丁酯、乙酰乙酸甲酯、乙酰乙酸乙酯、丙酸甲酯、丙酸乙酯、丙酸丙酯、丙酸异丙酯、2-羟基丙酸甲酯、2-羟基丙酸乙酯、3-甲氧基丙酸甲酯、3-甲氧基丙酸乙酯、3-乙氧基丙酸乙酯、3-甲氧基丙酸丙酯等作为例子。而且,作为上述显影液,可以优选使用乙酸丁酯、2-庚酮等。
进而,也可以在这些显影液中加入表面活性剂等。作为显影条件,从温度5~50℃,时间10~600秒中进行适当地选择。
接着对本发明的抗蚀剂图案的形成方法进行说明,在精密集成电路元件制造中使用的基板(例如硅/二氧化硅被覆、玻璃基板、ITO基板等透明基板)上,通过旋转器、涂布机等适当的涂布方法涂布抗蚀剂下层膜形成用组合物,然后进行烘烤使其固化而制成涂布型下层膜。此时,抗蚀剂下层膜的膜厚优选为0.01~3.0μm。另外,涂布后烘烤(固化)的条件为在80~400℃下0.5~120分钟。之后在抗蚀剂下层膜上直接涂布抗蚀剂,或者在根据需要使1层~数层的涂膜材料在涂布型下层膜上进行成膜后涂布抗蚀剂,通过规定的掩模进行光或电子束照射,进行显影、漂洗、干燥,从而可以得到良好的抗蚀剂图案。也可以根据需要进行光或电子束的照射后加热(PEB:Post Exposure Bake)。然后,可以利用干蚀刻除去已通过上述工序显影除去了抗蚀剂的部位的抗蚀剂下层膜,在基板上形成期望的图案。
上述光致抗蚀剂的曝光光线为近紫外线、远紫外线、或极紫外线(例如EUV,波长13.5nm)等化学射线,可以使用例如248nm(KrF激光)、193nm(ArF激光)、157nm(F2激光)等波长的光。对于光照射,只要是能够从光产酸剂产生酸的方法,就可以没有特别限制地使用,曝光量按照1~2000mJ/cm2、或10~1500mJ/cm2、或50~1000mJ/cm2设定。
另外,电子束抗蚀剂的电子束照射可以使用例如电子束照射装置进行照射。
在本发明中,可以经过以下工序来制造半导体装置:利用抗蚀剂下层膜形成用组合物在半导体基板上形成该抗蚀剂下层膜的工序,在该抗蚀剂下层膜上形成抗蚀剂膜的工序,通过照射光或电子束并且显影而形成抗蚀剂图案的工序,利用抗蚀剂图案对该下层膜进行蚀刻的工序,以及利用图案化了的抗蚀剂下层膜来加工半导体基板的工序。
今后,如果抗蚀剂图案的微细化推进,则会出现分辨率的问题、抗蚀剂图案在显影后倒塌这样的问题,期望抗蚀剂的薄膜化。因此,难以得到对于基板加工来说充分的抗蚀剂图案膜厚,需要不仅使抗蚀剂图案,而且使在抗蚀剂和所加工的半导体基板之间制成的抗蚀剂下层膜也具有作为基板加工时的掩模的功能的工艺。作为在这样的工艺中使用的抗蚀剂下层膜,与以往的高蚀刻速率性(蚀刻速度快的)抗蚀剂下层膜不同,要求具有与抗蚀剂接近的干蚀刻速度选择比的光刻用抗蚀剂下层膜、具有比抗蚀剂小的干蚀刻速度选择比的光刻用抗蚀剂下层膜、具有比半导体基板小的干蚀刻速度选择比的光刻用抗蚀剂下层膜。另外,也可以对这样的抗蚀剂下层膜赋予防反射能力,使其同时具有以往的防反射膜的功能。
另一方面,为了得到微细的抗蚀剂图案,也开始使用下述工艺:在进行抗蚀剂下层膜的干蚀刻时,使抗蚀剂图案和抗蚀剂下层膜比抗蚀剂显影时的图案宽度窄。作为在这样的工艺中使用的抗蚀剂下层膜,与以往的高蚀刻速率性防反射膜不同,要求具有与抗蚀剂接近的干蚀刻速度选择比的抗蚀剂下层膜。另外,也可以对这样的抗蚀剂下层膜赋予防反射能力,使其同时具有以往的防反射膜的功能。
在本发明中,可以在基板上进行本发明的抗蚀剂下层膜成膜,然后在抗蚀剂下层膜上直接涂布抗蚀剂,或者根据需要在抗蚀剂下层膜上将1层~数层的涂膜材料进行成膜后涂布抗蚀剂。通过这样的方式抗蚀剂的图案宽度变窄,即使是在为了防止图案倒塌而被覆较薄的抗蚀剂的情况下,也可以通过选择适当的蚀刻气体进行基板的加工。
即,可以经过下述工序来制造半导体装置:利用抗蚀剂下层膜形成用组合物在半导体基板上形成该抗蚀剂下层膜的工序,在该抗蚀剂下层膜上利用含有硅成分等的涂膜材料形成硬掩模或通过蒸镀形成硬掩模(例如,氮氧化硅)的工序,进而在该硬掩模上形成抗蚀剂膜的工序,通过照射光或电子束并且显影而形成抗蚀剂图案的工序,利用抗蚀剂图案、使用卤系气体对硬掩模进行蚀刻的工序,利用图案化了的硬掩模、使用氧系气体或氢系气体对该抗蚀剂下层膜进行蚀刻的工序,以及利用图案化了的抗蚀剂下层膜、使用卤系气体来加工半导体基板的工序。
对于本发明的光刻用抗蚀剂下层膜形成用组合物,在考虑作为防反射膜的效果的情况下,由于光吸收部位被引入骨架中,因此加热干燥时不存在向光致抗蚀剂中的扩散物,另外,光吸收部位具有充分好的吸光性能,因此防止反射光的效果好。
作为本发明的光刻用抗蚀剂下层膜形成用组合物,热稳定性高,可以防止烧成时分解物导致的对上层膜的污染,另外,也可以使烧成工序的温度余量有富余。
进而,本发明的光刻用抗蚀剂下层膜材料可以根据工艺条件而作为具有防止光反射的功能、和进一步具有防止基板和光致抗蚀剂的相互作用或防止光致抗蚀剂中使用的材料或对光致抗蚀剂曝光时生成的物质对基板的不良作用的功能的膜使用。
实施例
(实施例1)
在8.00g的2-苯基吲哚、5.72g的1-芘甲醛、2.06g的2-羟基苄醇、0.36g的甲烷磺酸中加入29.96g丙二醇单甲基醚,在氮气气氛下、在130℃下进行了24小时搅拌。将反应液滴加到甲醇中,将析出的树脂进行过滤、洗涤,然后在70℃下减压干燥,从而得到6.15g含有式(3-1)的树脂。另外,通过GPC并由标准聚苯乙烯换算测得的该树脂的重均分子量为1370。
接着,将1.00g该得到的树脂、0.002g表面活性剂(DIC(株)制,品名:メガファック〔商品名〕R-40,氟系表面活性剂)溶解在5.70g丙二醇单甲基醚、13.30g丙二醇单甲基醚乙酸酯中,调制成抗蚀剂下层膜形成用组合物。
(实施例2)
在8.00g的2-苯基吲哚、5.72g的1-芘甲醛、2.06g的4-羟基苄醇、0.36g的甲烷磺酸中加入29.96g丙二醇单甲基醚,在氮气气氛下、在130℃下进行了24小时搅拌。将反应液滴加到甲醇中,将析出的树脂进行过滤、洗涤,然后在70℃下减压干燥,从而得到5.52g含有式(3-2)的树脂。另外,通过GPC并由标准聚苯乙烯换算测得的该树脂的重均分子量为1100。
接着,将1.00g该得到的树脂、0.002g表面活性剂(DIC(株)制,品名:メガファック〔商品名〕R-40,氟系表面活性剂)溶解在5.70g丙二醇单甲基醚、13.30g丙二醇单甲基醚乙酸酯中,调制成抗蚀剂下层膜形成用组合物。
(实施例3)
在7.50g的2-苯基吲哚、5.36g的1-芘甲醛、3.70g的2,6-二叔丁基-4-羟基甲基苯酚、0.34g的甲烷磺酸中加入31.32g丙二醇单甲基醚,在氮气气氛下、在130℃下进行了24小时搅拌。将反应液滴加到甲醇中,将析出的树脂进行过滤、洗涤,然后在70℃下减压干燥,从而得到6.45g含有式(3-3)的树脂。另外,通过GPC并由标准聚苯乙烯换算测得的该树脂的重均分子量为1510。
接着,将1.00g该得到的树脂、0.002g表面活性剂(DIC(株)制,品名:メガファック〔商品名〕R-40,氟系表面活性剂)溶解在5.70g丙二醇单甲基醚、13.30g丙二醇单甲基醚乙酸酯中,调制成抗蚀剂下层膜形成用组合物。
(实施例4)
在10.00g的苯基-1-萘胺、10.50g的1-芘甲醛、5.39g的2,6-二叔丁基-4-羟基甲基苯酚、0.99g的甲烷磺酸中加入40.00g的1,4-二烷,在氮气气氛下、在回流状态下进行了24小时搅拌。将反应液滴加到甲醇中,将析出的树脂进行过滤、洗涤,然后在70℃下减压干燥,从而得到15.58g含有式(3-6)的树脂。另外,通过GPC并由标准聚苯乙烯换算测得的该树脂的重均分子量为2600。
接着,将1.00g该得到的树脂、0.002g表面活性剂(DIC(株)制,品名:メガファック〔商品名〕R-40,氟系表面活性剂)溶解在13.30g环己酮、5.70g丙二醇单甲基醚乙酸酯中,调制成抗蚀剂下层膜形成用组合物。
(比较例1)
在8.39g的2-苯基吲哚、10.00g的1-芘甲醛、0.42g的甲烷磺酸中加入5.64g丙二醇单甲基醚、22.57g丙二醇单甲基醚乙酸酯,在氮气气氛下、在130℃下进行了24小时搅拌。将反应液滴加到甲醇中,将析出的树脂进行过滤、洗涤,然后在70℃下减压干燥,从而得到15.10g含有下述式(5-1)的树脂。另外,通过GPC并由标准聚苯乙烯换算测得的该树脂的重均分子量为1200。
接着,将1.00g该得到的树脂、0.002g表面活性剂(DIC(株)制,品名:メガファック〔商品名〕R-40,氟系表面活性剂)溶解在5.70g丙二醇单甲基醚、13.30g环己酮中,调制成抗蚀剂下层膜形成用组合物。
(比较例2)
在11.00g的苯基-1-萘胺、11.55g的1-芘甲醛、0.48g的甲烷磺酸中加入17.27g的1,4-二烷、17.27g甲苯,在氮气气氛下、在回流状态下进行了16小时搅拌。将反应液滴加到甲醇中,将析出的树脂进行过滤、洗涤,然后在70℃下减压干燥,从而得到19.88g含有下述式(5-2)的树脂。另外,通过GPC并由标准聚苯乙烯换算测得的该树脂的重均分子量为900。
接着,将1.00g该得到的树脂、0.002g表面活性剂(DIC(株)制,品名:メガファック〔商品名〕R-40,氟系表面活性剂)溶解在5.70g丙二醇单甲基醚、13.30g环己酮中,调制成抗蚀剂下层膜形成用组合物。
(比较例3)
在10.00g的2-苯基吲哚、7.15g的1-芘甲醛、2.24g的苄醇、0.45g的甲烷磺酸中加入36.84g丙二醇单甲基醚,在氮气气氛下、在130℃下进行了22小时搅拌。将反应液滴加到甲醇中,将析出的树脂进行过滤、洗涤,然后在70℃下减压干燥,从而得到9.70g含有下述式(5-3)的树脂。另外,通过GPC并由标准聚苯乙烯换算测得的该树脂的重均分子量为1270。
接着,将1.00g该得到的树脂、0.002g表面活性剂(DIC(株)制,品名:メガファック〔商品名〕R-40,氟系表面活性剂)溶解在5.70g丙二醇单甲基醚、13.30g环己酮中,调制成抗蚀剂下层膜形成用组合物。
(比较例4)
在10.00g的2-苯基吲哚、7.15g的1-芘甲醛、2.52g的水杨醛、0.45g的甲烷磺酸中加入37.37g丙二醇单甲基醚,在氮气气氛下、在130℃下进行了22小时搅拌。将反应液滴加到甲醇中,将析出的树脂进行过滤、洗涤,然后在70℃下减压干燥,从而得到9.84g含有下述式(5-4)的树脂。另外,通过GPC并由标准聚苯乙烯换算测得的该树脂的重均分子量为1360。
接着,将1.00g该得到的树脂、0.002g表面活性剂(DIC(株)制,品名:メガファック〔商品名〕R-40,氟系表面活性剂)溶解在5.70g丙二醇单甲基醚、13.30g环己酮中,调制成抗蚀剂下层膜形成用组合物。
(比较例5)
在60.00g间甲苯酚(m-cresol)、27.00g的37%***水溶液、1.60g对甲苯磺酸一水合物中加入150g丙二醇单甲基醚,在氮气气氛下、在回流状态下进行了24小时搅拌。将反应液滴加到甲醇中,将析出的树脂进行过滤、洗涤,然后在70℃下减压干燥。接着,在12.02g该得到的树脂中加入4.13g的9-蒽甲醇、28.80g的THF、0.52g对甲苯磺酸一水合物,在氮气气氛下、在回流状态下进行了24小时搅拌。将反应液滴加到甲醇中,将析出的树脂进行过滤、洗涤,然后在70℃下减压干燥,从而得到2.75g含有下述式(5-5)的树脂。另外,通过GPC并由标准聚苯乙烯换算测得的该树脂的重均分子量为1470。
接着,将1.00g该得到的树脂、0.002g表面活性剂(DIC(株)制,品名:メガファック〔商品名〕R-40,氟系表面活性剂)溶解在5.70g丙二醇单甲基醚、13.30g丙二醇单甲基醚乙酸酯中,调制成抗蚀剂下层膜形成用组合物。
(溶解性试验)
将通过实施例1~实施例4、比较例1~比较例3得到的树脂调制成作为代表性抗蚀剂溶剂的丙二醇单甲基醚(PGME)的30质量%溶液。此时,将树脂溶解而得到均匀溶液的情况设为溶解性“良好”,将未充分溶解而得到悬浮液的情况设为溶解性“不良”。将该树脂溶解性试验的结果列于表1中。
[表1]
表1 树脂的溶解性试验
由表1的结果可以确认:实施例1~实施例4的树脂与比较例1~比较例3相比,在作为代表性抗蚀剂溶剂的PGME中显示出高的溶解性。
(干蚀刻速度的测定)
干蚀刻速度的测定中使用的蚀刻机及蚀刻气体如下。
ES401(日本サイエンティフィック制):CF4
分别使用旋转涂布机将通过实施例1~4及比较例4、5调制的抗蚀剂下层膜形成用组合物的溶液涂布在硅晶片上。在加热板上于400℃进行2分钟烧成,形成抗蚀剂下层膜(膜厚0.25μm)。使用CF4气体作为蚀刻气体测定干蚀刻速度。
另外,同样地使用旋转涂布机将苯酚酚醛清漆树脂(phenol novolac resin)(市售品,通过GPC并由聚苯乙烯换算测得的重均分子量Mw为2000,多分散度Mw/Mn为2.5)溶液涂布在硅晶片上,于205℃进行1分钟烧成而形成涂膜。使用CF4气体作为蚀刻气体测定干蚀刻速度。在使于205℃进行1分钟烧成而得到的苯酚酚醛清漆树脂膜(膜厚0.25μm)的蚀刻速度为1.00时,将实施例1~4及比较例4、5的抗蚀剂下层膜的干蚀刻速度、与苯酚酚醛清漆树脂的干蚀刻速度进行比较。结果示于表2中。速度比是(抗蚀剂下层膜)/(苯酚酚醛清漆树脂膜)的干蚀刻速度比。
表2 干蚀刻速度比
在本发明中使用的含有结构体(C)的酚醛清漆树脂中,含羟基的芳香族羟甲基化合物(B)必须含有羟基。在(B)不含羟基的情况(比较例3)下,在溶剂中的溶解性不充分。
另外,在芳香族化合物(A)使用含有羟基的醛来制造酚醛清漆树脂的情况(比较例4)下,形成从酚醛清漆聚合物主链伸出的侧链上存在羟基的结构,干蚀刻速度变高,作为硬掩模的性能下降。
本发明中使用的聚合物可以认为是含羟基的芳香族羟甲基化合物(B)存在于酚醛清漆树脂的末端的聚合物,通过使用具有这样的结构的聚合物,从而在溶剂中的溶解性提高,防止在基板上进行涂布时成为异物原因的溶解不良,而且涂布后固化得到的下层膜显示出高耐蚀刻性,具有良好的硬掩模特性。
产业上的可以利用性
由此,本发明的采用多层膜的光刻工艺中使用的抗蚀剂下层膜材料不仅具有高的耐干蚀刻性和防反射膜功能,而且在抗蚀剂溶剂(光刻中使用的溶剂)中的溶解性高,因此旋涂性优异,得到的抗蚀剂下层膜与其上涂布的抗蚀剂不会互混(层混合),抑制干蚀刻工序引起的抗蚀剂下层膜的扭曲(不规则图案的弯曲)的发生,从而实现更微细的基板加工。
Claims (14)
1.一种抗蚀剂下层膜形成用组合物,包含酚醛清漆树脂,所述酚醛清漆树脂含有通过芳香族化合物(A)的芳香环与含羟基的芳香族羟甲基化合物(B)的反应而得到的结构体(C),
上述含羟基的芳香族羟甲基化合物(B)是式(1)所示的化合物,
式(1)中,Ar1表示碳原子数为6~40的芳基;R1表示碳原子数为1~10的烷基、碳原子数为2~10的烯基、碳原子数为2~10的炔基、碳原子数为6~40的芳基、羟基、氰基、硝基、氨基、羧基、乙酰基、卤代甲基、-Y-Z基、卤素原子、或它们的组合;Y表示氧原子、硫原子、羰基、或酯基,Z表示碳原子数为1~10的烷基;R2表示氢原子或甲基;R3、R4分别表示氢原子;m为0~(4+2n)的整数,n表示芳基Ar1具有的苯环的稠合度,
上述结构体(C)具有式(2)所示的结构,
式(2)中,Ar1、R1、R3、R4和m分别与式(1)中的Ar1、R1、R3、R4和m相同,A1为芳香族化合物(A)的芳香环。
2.根据权利要求1所述的抗蚀剂下层膜形成用组合物,上述含羟基的芳香族羟甲基化合物(B)为2-羟基苄醇、4-羟基苄醇、或2,6-二叔丁基-4-羟基甲基苯酚。
3.根据权利要求1或2所述的抗蚀剂下层膜形成用组合物,上述芳香族化合物(A)为芳香族胺或含有酚性羟基的化合物。
4.根据权利要求1或2所述的抗蚀剂下层膜形成用组合物,上述酚醛清漆树脂是通过芳香族胺或含有酚性羟基的化合物、与醛或酮反应而生成的树脂。
5.根据权利要求4所述的抗蚀剂下层膜形成用组合物,上述芳香族胺为苯基吲哚或苯基萘胺。
6.根据权利要求4所述的抗蚀剂下层膜形成用组合物,上述含有酚性羟基的化合物为苯酚、二羟基苯、三羟基苯、羟基萘、二羟基萘、三羟基萘、三(4-羟基苯基)甲烷、三(4-羟基苯基)乙烷、或1,1,2,2-四(4-羟基苯基)乙烷。
7.根据权利要求4所述的抗蚀剂下层膜形成用组合物,上述醛为萘甲醛或芘甲醛。
8.根据权利要求1或2所述的抗蚀剂下层膜形成用组合物,其中还含有溶剂。
9.根据权利要求1或2所述的抗蚀剂下层膜形成用组合物,其中还含有酸和/或产酸剂。
10.根据权利要求1或2所述的抗蚀剂下层膜形成用组合物,其中还含有交联剂。
11.一种在半导体制造中使用的抗蚀剂图案的形成方法,其中包含下述工序:将权利要求1~10中任一项所述的抗蚀剂下层膜形成用组合物涂布在半导体基板上,进行烧成从而形成下层膜。
12.一种半导体装置的制造方法,其中包含下述工序:利用权利要求1~10中任一项所述的抗蚀剂下层膜形成用组合物在半导体基板上形成下层膜的工序,在该下层膜上形成抗蚀剂膜的工序,通过照射光或电子束并且显影而形成抗蚀剂图案的工序,利用该抗蚀剂图案对该下层膜进行蚀刻的工序,以及利用图案化了的下层膜来加工半导体基板的工序。
13.一种半导体装置的制造方法,其中包含下述工序:利用权利要求1~10中任一项所述的抗蚀剂下层膜形成用组合物在半导体基板上形成下层膜的工序,在该下层膜上形成硬掩模的工序,进而在该硬掩模上形成抗蚀剂膜的工序,通过照射光或电子束并且显影而形成抗蚀剂图案的工序,利用该抗蚀剂图案对硬掩模进行蚀刻的工序,利用图案化了的硬掩模对该下层膜进行蚀刻的工序,以及利用图案化了的下层膜来加工半导体基板的工序。
14.根据权利要求13所述的制造方法,上述硬掩模由无机物蒸镀膜形成。
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
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KR101884447B1 (ko) * | 2015-07-06 | 2018-08-01 | 삼성에스디아이 주식회사 | 모노머, 유기막 조성물, 유기막, 및 패턴형성방법 |
WO2017094780A1 (ja) | 2015-12-01 | 2017-06-08 | 日産化学工業株式会社 | インドロカルバゾールノボラック樹脂を含むレジスト下層膜形成組成物 |
JP6643142B2 (ja) * | 2016-02-26 | 2020-02-12 | Hoya株式会社 | マスクブランク、レジスト膜付きマスクブランク、レジストパターン付きマスクブランク、およびそれらの製造方法、ならびに転写用マスクの製造方法 |
KR102667884B1 (ko) * | 2016-07-27 | 2024-05-23 | 삼성전자주식회사 | 반도체 소자의 제조 방법 |
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