CN103460138B - Developer solution containing polymer - Google Patents
Developer solution containing polymer Download PDFInfo
- Publication number
- CN103460138B CN103460138B CN201280014835.1A CN201280014835A CN103460138B CN 103460138 B CN103460138 B CN 103460138B CN 201280014835 A CN201280014835 A CN 201280014835A CN 103460138 B CN103460138 B CN 103460138B
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- CN
- China
- Prior art keywords
- developer solution
- resist
- polymer
- manufacture method
- semiconductor device
- 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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- 229920000642 polymer Polymers 0.000 title claims abstract description 48
- 238000000034 method Methods 0.000 claims abstract description 53
- 239000004065 semiconductor Substances 0.000 claims abstract description 32
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 claims abstract description 25
- 230000015572 biosynthetic process Effects 0.000 claims abstract description 23
- 239000000758 substrate Substances 0.000 claims abstract description 23
- 238000004519 manufacturing process Methods 0.000 claims abstract description 19
- 238000005755 formation reaction Methods 0.000 claims abstract description 17
- 239000003960 organic solvent Substances 0.000 claims abstract description 15
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 8
- 239000012046 mixed solvent Substances 0.000 claims abstract description 8
- LRHPLDYGYMQRHN-UHFFFAOYSA-N n-butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims abstract description 7
- XNLICIUVMPYHGG-UHFFFAOYSA-N 2-Pentanone Chemical class CCCC(C)=O XNLICIUVMPYHGG-UHFFFAOYSA-N 0.000 claims abstract description 6
- -1 phenolic aldehyde Chemical class 0.000 claims description 29
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 15
- 239000000203 mixture Substances 0.000 claims description 13
- 239000012528 membrane Substances 0.000 claims description 11
- 229920001296 polysiloxane Polymers 0.000 claims description 11
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N silicon Chemical group [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 claims description 7
- 229910052710 silicon Inorganic materials 0.000 claims description 7
- 238000001312 dry etching Methods 0.000 claims description 5
- 229920000591 gum Polymers 0.000 claims description 5
- 239000002966 varnish Substances 0.000 claims description 5
- 125000003118 aryl group Chemical group 0.000 claims description 4
- 238000009833 condensation Methods 0.000 claims description 4
- 230000005494 condensation Effects 0.000 claims description 4
- 230000003301 hydrolyzing Effects 0.000 claims description 4
- 150000004756 silanes Chemical class 0.000 claims description 4
- 239000004593 Epoxy Substances 0.000 claims description 3
- 229910018540 Si C Inorganic materials 0.000 claims description 2
- 125000003647 acryloyl group Chemical group O=C([*])C([H])=C([H])[H] 0.000 claims description 2
- 125000004423 acyloxy group Chemical group 0.000 claims description 2
- 125000003342 alkenyl group Chemical group 0.000 claims description 2
- 125000004171 alkoxy aryl group Chemical group 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 2
- 125000001188 haloalkyl group Chemical group 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 150000002367 halogens Chemical class 0.000 claims description 2
- 150000002576 ketones Chemical class 0.000 claims description 2
- 125000000962 organic group Chemical group 0.000 claims description 2
- 238000006116 polymerization reaction Methods 0.000 claims description 2
- 229910010271 silicon carbide Inorganic materials 0.000 claims description 2
- 229920005989 resin Polymers 0.000 abstract description 22
- 239000011347 resin Substances 0.000 abstract description 22
- 230000007261 regionalization Effects 0.000 abstract description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 14
- 239000002904 solvent Substances 0.000 description 13
- 229920003986 novolac Polymers 0.000 description 12
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 12
- RTZKZFJDLAIYFH-UHFFFAOYSA-N diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 11
- 239000003795 chemical substances by application Substances 0.000 description 10
- 239000000463 material Substances 0.000 description 10
- 238000011010 flushing procedure Methods 0.000 description 8
- 238000006460 hydrolysis reaction Methods 0.000 description 8
- MTHSVFCYNBDYFN-UHFFFAOYSA-N Diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 6
- 238000003786 synthesis reaction Methods 0.000 description 6
- 230000002194 synthesizing Effects 0.000 description 6
- 239000002253 acid Substances 0.000 description 5
- 239000011248 coating agent Substances 0.000 description 5
- 238000000576 coating method Methods 0.000 description 5
- 239000010703 silicon Substances 0.000 description 5
- KJCVRFUGPWSIIH-UHFFFAOYSA-N 1-Naphthol Chemical compound C1=CC=C2C(O)=CC=CC2=C1 KJCVRFUGPWSIIH-UHFFFAOYSA-N 0.000 description 4
- ARXJGSRGQADJSQ-UHFFFAOYSA-N 1-methoxypropan-2-ol Chemical compound COCC(C)O ARXJGSRGQADJSQ-UHFFFAOYSA-N 0.000 description 4
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butanoic acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 4
- 238000011049 filling Methods 0.000 description 4
- 239000007789 gas Substances 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- MUBZPKHOEPUJKR-UHFFFAOYSA-N oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N acetic acid ethyl ester Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- 230000003712 anti-aging Effects 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
- 229910052799 carbon Inorganic materials 0.000 description 3
- 239000003054 catalyst 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
- 239000000470 constituent Substances 0.000 description 3
- 238000005260 corrosion Methods 0.000 description 3
- 230000018109 developmental process Effects 0.000 description 3
- 239000003814 drug Substances 0.000 description 3
- 229940079593 drugs Drugs 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- 238000005530 etching Methods 0.000 description 3
- 235000019197 fats Nutrition 0.000 description 3
- BDAGIHXWWSANSR-UHFFFAOYSA-N formic acid Chemical compound OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 150000007522 mineralic acids Chemical class 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- KBPLFHHGFOOTCA-UHFFFAOYSA-N octanol Chemical compound CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 3
- 150000007524 organic acids Chemical class 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- ULWHHBHJGPPBCO-UHFFFAOYSA-N propane-1,1-diol Chemical class CCC(O)O ULWHHBHJGPPBCO-UHFFFAOYSA-N 0.000 description 3
- XBDQKXXYIPTUBI-UHFFFAOYSA-N propionic acid Chemical compound CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 238000004528 spin coating Methods 0.000 description 3
- LHXDLQBQYFFVNW-XCBNKYQSSA-N (+)-Fenchone Natural products C1C[C@]2(C)C(=O)C(C)(C)[C@H]1C2 LHXDLQBQYFFVNW-XCBNKYQSSA-N 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N (E)-but-2-enedioate;hydron Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- FYGHSUNMUKGBRK-UHFFFAOYSA-N 1,2,3-Trimethylbenzene Chemical compound CC1=CC=CC(C)=C1C FYGHSUNMUKGBRK-UHFFFAOYSA-N 0.000 description 2
- MWKFXSUHUHTGQN-UHFFFAOYSA-N 1-Decanol Chemical compound CCCCCCCCCCO MWKFXSUHUHTGQN-UHFFFAOYSA-N 0.000 description 2
- ZSIAUFGUXNUGDI-UHFFFAOYSA-N 1-Hexanol Chemical compound CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 description 2
- HLZKNKRTKFSKGZ-UHFFFAOYSA-N 1-Tetradecanol Chemical group CCCCCCCCCCCCCCO HLZKNKRTKFSKGZ-UHFFFAOYSA-N 0.000 description 2
- SVTBMSDMJJWYQN-UHFFFAOYSA-N 2-Methyl-2,4-pentanediol Chemical compound CC(O)CC(C)(C)O SVTBMSDMJJWYQN-UHFFFAOYSA-N 0.000 description 2
- JYVLIDXNZAXMDK-UHFFFAOYSA-N 2-Pentanol Chemical compound CCCC(C)O JYVLIDXNZAXMDK-UHFFFAOYSA-N 0.000 description 2
- XLLIQLLCWZCATF-UHFFFAOYSA-N 2-methoxyethyl acetate Chemical compound COCCOC(C)=O XLLIQLLCWZCATF-UHFFFAOYSA-N 0.000 description 2
- WNLRTRBMVRJNCN-UHFFFAOYSA-N Adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N Benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- UJOBWOGCFQCDNV-UHFFFAOYSA-N Carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 2
- FXHOOIRPVKKKFG-UHFFFAOYSA-N DMA Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 2
- GHVNFZFCNZKVNT-UHFFFAOYSA-N Decanoic acid Chemical compound CCCCCCCCCC(O)=O GHVNFZFCNZKVNT-UHFFFAOYSA-N 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
- FKRCODPIKNYEAC-UHFFFAOYSA-N Ethyl propionate Chemical compound CCOC(=O)CC FKRCODPIKNYEAC-UHFFFAOYSA-N 0.000 description 2
- LNTHITQWFMADLM-UHFFFAOYSA-N Gallic acid Chemical compound OC(=O)C1=CC(O)=C(O)C(O)=C1 LNTHITQWFMADLM-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N HCl Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- KRHYYFGTRYWZRS-UHFFFAOYSA-N HF Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 description 2
- FUZZWVXGSFPDMH-UHFFFAOYSA-N Hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 2
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N Isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 2
- OYHQOLUKZRVURQ-IXWMQOLASA-N Linoleic acid Natural products CCCCC\C=C/C\C=C\CCCCCCCC(O)=O OYHQOLUKZRVURQ-IXWMQOLASA-N 0.000 description 2
- 241000539716 Mea Species 0.000 description 2
- FBUKVWPVBMHYJY-UHFFFAOYSA-N Nonanoic acid Chemical compound CCCCCCCCC(O)=O FBUKVWPVBMHYJY-UHFFFAOYSA-N 0.000 description 2
- QYSGYZVSCZSLHT-UHFFFAOYSA-N Octafluoropropane Chemical compound FC(F)(F)C(F)(F)C(F)(F)F QYSGYZVSCZSLHT-UHFFFAOYSA-N 0.000 description 2
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N Oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 2
- YGSDEFSMJLZEOE-UHFFFAOYSA-N Salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 2
- QIQXTHQIDYTFRH-UHFFFAOYSA-N Stearic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N Valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid Chemical class OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 230000000996 additive Effects 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 238000006297 dehydration reaction Methods 0.000 description 2
- 229940043237 diethanolamine Drugs 0.000 description 2
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- 238000006073 displacement reaction Methods 0.000 description 2
- WSFSSNUMVMOOMR-UHFFFAOYSA-N formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 229940051250 hexylene glycol Drugs 0.000 description 2
- 150000007529 inorganic bases Chemical class 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N iso-propanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- NHTMVDHEPJAVLT-UHFFFAOYSA-N isooctane Chemical class CC(C)CC(C)(C)C NHTMVDHEPJAVLT-UHFFFAOYSA-N 0.000 description 2
- OFOBLEOULBTSOW-UHFFFAOYSA-N malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 2
- OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 2
- QMMFVYPAHWMCMS-UHFFFAOYSA-N methyl sulfide Chemical compound CSC QMMFVYPAHWMCMS-UHFFFAOYSA-N 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N n-heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- AMQJEAYHLZJPGS-UHFFFAOYSA-N n-pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 150000007530 organic bases Chemical class 0.000 description 2
- 238000000059 patterning Methods 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 229920000193 polymethacrylate Polymers 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- CIBMHJPPKCXONB-UHFFFAOYSA-N propane-2,2-diol Chemical compound CC(C)(O)O CIBMHJPPKCXONB-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 229920003987 resole Polymers 0.000 description 2
- 241000894007 species Species 0.000 description 2
- DKGAVHZHDRPRBM-UHFFFAOYSA-N t-BuOH Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- YXFVVABEGXRONW-UHFFFAOYSA-N toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 2
- ZMANZCXQSJIPKH-UHFFFAOYSA-N triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 2
- DTQVDTLACAAQTR-UHFFFAOYSA-N trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- VIDOPANCAUPXNH-UHFFFAOYSA-N 1,2,3-triethylbenzene Chemical compound CCC1=CC=CC(CC)=C1CC VIDOPANCAUPXNH-UHFFFAOYSA-N 0.000 description 1
- OKIRBHVFJGXOIS-UHFFFAOYSA-N 1,2-di(propan-2-yl)benzene Chemical compound CC(C)C1=CC=CC=C1C(C)C OKIRBHVFJGXOIS-UHFFFAOYSA-N 0.000 description 1
- KVNYFPKFSJIPBJ-UHFFFAOYSA-N 1,2-diethylbenzene Chemical compound CCC1=CC=CC=C1CC KVNYFPKFSJIPBJ-UHFFFAOYSA-N 0.000 description 1
- 229940058015 1,3-butylene glycol Drugs 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- ALQSHHUCVQOPAS-UHFFFAOYSA-N 1,5-Pentanediol Chemical compound OCCCCCO ALQSHHUCVQOPAS-UHFFFAOYSA-N 0.000 description 1
- SEXKDZSOKXPFFH-UHFFFAOYSA-N 1-(2-benzoylphenyl)ethanone Chemical compound CC(=O)C1=CC=CC=C1C(=O)C1=CC=CC=C1 SEXKDZSOKXPFFH-UHFFFAOYSA-N 0.000 description 1
- GDXHBFHOEYVPED-UHFFFAOYSA-N 1-(2-butoxyethoxy)butane Chemical class CCCCOCCOCCCC GDXHBFHOEYVPED-UHFFFAOYSA-N 0.000 description 1
- ZWRUINPWMLAQRD-UHFFFAOYSA-N 1-Nonanol Chemical group CCCCCCCCCO ZWRUINPWMLAQRD-UHFFFAOYSA-N 0.000 description 1
- HPFDGTFXAVIVTH-UHFFFAOYSA-N 1-[1-(1-methoxypropan-2-yloxy)propan-2-yloxy]propan-2-ol Chemical compound COCC(C)OCC(C)OCC(C)O HPFDGTFXAVIVTH-UHFFFAOYSA-N 0.000 description 1
- KZVBBTZJMSWGTK-UHFFFAOYSA-N 1-[2-(2-butoxyethoxy)ethoxy]butane Chemical compound CCCCOCCOCCOCCCC KZVBBTZJMSWGTK-UHFFFAOYSA-N 0.000 description 1
- MQGIBEAIDUOVOH-UHFFFAOYSA-N 1-[2-[2-[2-(2-butoxyethoxy)ethoxy]ethoxy]ethoxy]butane Chemical compound CCCCOCCOCCOCCOCCOCCCC MQGIBEAIDUOVOH-UHFFFAOYSA-N 0.000 description 1
- DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical compound CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 description 1
- PPNCOQHHSGMKGI-UHFFFAOYSA-N 1-cyclononyldiazonane Chemical compound C1CCCCCCCC1N1NCCCCCCC1 PPNCOQHHSGMKGI-UHFFFAOYSA-N 0.000 description 1
- NFDXQGNDWIPXQL-UHFFFAOYSA-N 1-cyclooctyldiazocane Chemical compound C1CCCCCCC1N1NCCCCCC1 NFDXQGNDWIPXQL-UHFFFAOYSA-N 0.000 description 1
- HYFLWBNQFMXCPA-UHFFFAOYSA-N 1-ethyl-2-methylbenzene Chemical compound CCC1=CC=CC=C1C HYFLWBNQFMXCPA-UHFFFAOYSA-N 0.000 description 1
- 150000004782 1-naphthols Chemical class 0.000 description 1
- FDHDUXOBMHHFFJ-UHFFFAOYSA-N 1-pentylnaphthalene Chemical compound C1=CC=C2C(CCCCC)=CC=CC2=C1 FDHDUXOBMHHFFJ-UHFFFAOYSA-N 0.000 description 1
- WAPNOHKVXSQRPX-UHFFFAOYSA-N 1-phenylethanol Chemical compound CC(O)C1=CC=CC=C1 WAPNOHKVXSQRPX-UHFFFAOYSA-N 0.000 description 1
- VYQKBQPWMKITOI-UHFFFAOYSA-N 2,2-dimethyldecan-3-one Chemical compound CCCCCCCC(=O)C(C)(C)C VYQKBQPWMKITOI-UHFFFAOYSA-N 0.000 description 1
- PTTPXKJBFFKCEK-UHFFFAOYSA-N 2,6-dimethylheptan-4-one Chemical compound CC(C)CC(=O)CC(C)C PTTPXKJBFFKCEK-UHFFFAOYSA-N 0.000 description 1
- SBASXUCJHJRPEV-UHFFFAOYSA-N 2-(2-Methoxyethoxy)ethanol Chemical compound COCCOCCO SBASXUCJHJRPEV-UHFFFAOYSA-N 0.000 description 1
- BTANRVKWQNVYAZ-UHFFFAOYSA-N 2-Butanol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 description 1
- POAOYUHQDCAZBD-UHFFFAOYSA-N 2-Butoxyethanol Chemical compound CCCCOCCO POAOYUHQDCAZBD-UHFFFAOYSA-N 0.000 description 1
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-Ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 1
- TZYRSLHNPKPEFV-UHFFFAOYSA-N 2-Ethyl-1-butanol Chemical group CCC(CC)CO TZYRSLHNPKPEFV-UHFFFAOYSA-N 0.000 description 1
- OBETXYAYXDNJHR-UHFFFAOYSA-N 2-Ethylhexanoic acid Chemical compound CCCCC(CC)C(O)=O OBETXYAYXDNJHR-UHFFFAOYSA-N 0.000 description 1
- YIWUKEYIRIRTPP-UHFFFAOYSA-N 2-Ethylhexanol Chemical compound CCCCC(CC)CO YIWUKEYIRIRTPP-UHFFFAOYSA-N 0.000 description 1
- QQZOPKMRPOGIEB-UHFFFAOYSA-N 2-Hexanone Chemical compound CCCCC(C)=O QQZOPKMRPOGIEB-UHFFFAOYSA-N 0.000 description 1
- QPRQEDXDYOZYLA-UHFFFAOYSA-N 2-Methyl-1-butanol Chemical class CCC(C)CO QPRQEDXDYOZYLA-UHFFFAOYSA-N 0.000 description 1
- GXDHCNNESPLIKD-UHFFFAOYSA-N 2-Methylhexane Chemical compound CCCCC(C)C GXDHCNNESPLIKD-UHFFFAOYSA-N 0.000 description 1
- BSKHPKMHTQYZBB-UHFFFAOYSA-N 2-Methylpyridine Chemical compound CC1=CC=CC=N1 BSKHPKMHTQYZBB-UHFFFAOYSA-N 0.000 description 1
- JWUJQDFVADABEY-UHFFFAOYSA-N 2-Methyltetrahydrofuran Chemical class CC1CCCO1 JWUJQDFVADABEY-UHFFFAOYSA-N 0.000 description 1
- WFSMVVDJSNMRAR-UHFFFAOYSA-N 2-[2-(2-ethoxyethoxy)ethoxy]ethanol Chemical compound CCOCCOCCOCCO WFSMVVDJSNMRAR-UHFFFAOYSA-N 0.000 description 1
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- LSNNMFCWUKXFEE-UHFFFAOYSA-N sulfonic acid Chemical compound OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 229960000909 sulfur hexafluoride Drugs 0.000 description 1
- 229960001367 tartaric acid Drugs 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- WGTYBPLFGIVFAS-UHFFFAOYSA-M tetramethylammonium hydroxide Substances [OH-].C[N+](C)(C)C WGTYBPLFGIVFAS-UHFFFAOYSA-M 0.000 description 1
- YTPLMLYBLZKORZ-UHFFFAOYSA-N thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 1
- CPUDPFPXCZDNGI-UHFFFAOYSA-N triethoxy(methyl)silane Chemical compound CCO[Si](C)(OCC)OCC CPUDPFPXCZDNGI-UHFFFAOYSA-N 0.000 description 1
- JCVQKRGIASEUKR-UHFFFAOYSA-N triethoxy(phenyl)silane Chemical compound CCO[Si](OCC)(OCC)C1=CC=CC=C1 JCVQKRGIASEUKR-UHFFFAOYSA-N 0.000 description 1
- JLGLQAWTXXGVEM-UHFFFAOYSA-N triethylene glycol monomethyl ether Chemical compound COCCOCCOCCO JLGLQAWTXXGVEM-UHFFFAOYSA-N 0.000 description 1
- HADKRTWCOYPCPH-UHFFFAOYSA-M trimethylphenylammonium hydroxide Chemical compound [OH-].C[N+](C)(C)C1=CC=CC=C1 HADKRTWCOYPCPH-UHFFFAOYSA-M 0.000 description 1
- ZPQAKYPOZRXKFA-UHFFFAOYSA-N undecan-6-one Chemical compound CCCCCC(=O)CCCCC ZPQAKYPOZRXKFA-UHFFFAOYSA-N 0.000 description 1
- 229940005605 valeric acid Drugs 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- GAEKPEKOJKCEMS-UHFFFAOYSA-N γ-Valerolactone Chemical compound CC1CCC(=O)O1 GAEKPEKOJKCEMS-UHFFFAOYSA-N 0.000 description 1
Abstract
The problem of the present invention is to provide the developer solution that pattern collapse does not occur when forming fine pattern and the pattern formation method using the developer solution.The method solved the problems, such as the present invention is a kind of developer solution used in a lithographic process, to include dry ecthing mask formation polymer and organic solvent.Polymer is the resins different from resist.It is the developer solution used after the exposure of resist.Developer solution is the mixed solvent or the developer solution of 2 pentanones or the mixed solvent of 2 pentanones and alcohol as butyl acetate or butyl acetate and alcohol.A kind of manufacture method of semiconductor device, including following process：Process (A), coat resist on a semiconductor substrate and form resist layer, and be exposed；Process (B), makes the surface of the resist layer be contacted with developer solution, polymeric layer is formed between Resist patterns；Process (C), resist layer is removed by dry ecthing, forms the inversion pattern as caused by the polymer.
Description
Technical field
The present invention relates to the developer solution used in a lithographic process.
Background technology
All the time, fine add, is carried out by using the photoetching of photo-corrosion-resisting agent composition in semiconductor devices manufacture
Work.The microfabrication is to form the film of photo-corrosion-resisting agent composition on silicon, thereon via depicting semiconductor
The mask pattern of the pattern of device irradiates ultraviolet isoreactivity light, develops, using obtained Resist patterns as diaphragm
The processing method that silicon wafer is etched.But in recent years, the highly integrated progress of semiconductor devices, use
Active ray also has from i lines (wavelength 365nm), KrF PRKs (wavelength 248nm) to ArF PRK (wavelength
193nm) the tendency of short wavelengthization.With this accompany, active ray from the diffusing reflection of substrate and/or the influence of standing wave be larger ask
Topic.Then people extensively study sets antireflection film (bottom ARC, bottom between photoresist and substrate
Anti-reflective coating) method.
Due to the miniaturization of pattern, the development and the flushing of developer solution carried out in photo-mask process after anti-aging drug
The phenomenon of pattern collapse turns into problem in process.
The reason for considering pattern collapse be, surface tension when being dried due to developer solution and/or flushing liquor and/or with liquid
Power caused by the flowing of body and power, the i.e. Laplce's power acted between the patterns.Consider in addition, make developer solution using centrifugal force
And/or flushing liquor fly to outside when also produce above-mentioned Laplce's power, so as to which pattern collapse occur.
It is such in order to solve the problems, such as, disclose a kind of pattern formation method, it is characterised in that including following process：
The process that resist film is formed on substrate；In order to form sub-image on the resist film, and the resist film is selected to shine
The process for penetrating energy line；In order to form Resist patterns by the resist film for foring the sub-image, and to described against corrosion
The process that developer solution (alkaline-based developer) is supplied on agent film；In order to which the developer solution on the substrate is replaced as into flushing liquor, and it is right
The process that the flushing liquor is supplied on the substrate；It is molten in order to be replaced as at least a portion comprising the flushing liquor on the substrate
Agent and the film material of the solute different from the resist film, the work to supplying the film material on the substrate
Sequence；In order to form the film of covering resist film, the process for making the solvent in the film material volatilize on the substrate；
In order that the mask pattern being made up of the film is exposed and formed at least a portion above the Resist patterns, make described
The process that at least a portion on the surface of film retreats；The process of the substrate is processed using the mask pattern (with reference to specially
Sharp document 1).
Prior art literature
Patent document 1:Japanese Unexamined Patent Publication 2005-277052 publications
The content of the invention
The invention problem to be solved
If Resist patterns becomes fine, development when by developer solution centrifugal dehydration when, still can be due to La Pula
This power and pattern collapse occurs.
Show it is an object of the invention to provide the developer solution that pattern collapse does not occur when forming fine pattern and using this
The pattern formation method of shadow liquid.
For solving the method for problem
The present invention is used as the 1st viewpoint, is a kind of developer solution, is the developer solution used in a lithographic process, contains dry ecthing
Mask formation polymer and organic solvent.
It is the developer solution according to the 1st viewpoint as the 2nd viewpoint, the polymer is with forming consolidating for resist film
The property the changed different curable resin of resin.
It is the developer solution according to the 1st viewpoint or the 2nd viewpoint, the developer solution is in the resist as the 3rd viewpoint
Used after the exposure of film.
It is the developer solution according to any one of the viewpoint of the 1st viewpoint~the 3rd as the 4th viewpoint, in the developer solution
Organic solvent is the mixed solvent of butyl acetate or butyl acetate and alcohol.
It is the developer solution according to any one of the viewpoint of the 1st viewpoint~the 3rd as the 5th viewpoint, in the developer solution
Organic solvent is the mixed solvent of 2 pentanone or 2 pentanone and alcohol.
It is the developer solution according to any one of the viewpoint of the 1st viewpoint~the 5th, the polymer is phenol as the 6th viewpoint
Novolac resin or polysiloxane.
It is the developer solution according to any one of the viewpoint of the 1st viewpoint~the 6th as the 7th viewpoint, in the developer solution
The concentration of the polymer is 0.5~20 weight %.
It is a kind of manufacture method of semiconductor device as the 8th viewpoint, including following process (A)~process (C)：Process
(A), coat resist on a semiconductor substrate and form resist film, and be exposed；Process (B), makes the resist film
Developer solution described in any one of the viewpoint of surface and the 1st viewpoint~the 7th contacts, between the pattern of the resist film of the patterning
Form the layer of the polymer；Process (C), the resist film of the patterning is removed by dry ecthing, formed by the polymerization produce
Raw inversion pattern.
It is the manufacture method of the semiconductor device according to the 8th viewpoint as the 9th viewpoint, it is anti-in the process (A)
Erosion agent film be formed by form resist lower membrane on a semiconductor substrate, be then formed on resist film and carry out
's.
It is the manufacture method of the semiconductor device according to the 8th viewpoint as the 10th viewpoint, in the process (A)
Being formed by of resist film forms organic lower membrane on a semiconductor substrate, is then formed on the hard of silicon atoms and covers
Mould, then be formed on resist film and carry out.
It is the manufacture method according to any one of the viewpoint of the 8th viewpoint~the 10th, in the process as the 11st viewpoint
(B) in, the formation of the polymeric layer includes the operation for applying heat.And
It is the manufacture method according to any one of the viewpoint of the 8th viewpoint~the 11st, in the process as the 12nd viewpoint
(C) in, the dry etching rate ratio of resist/polymer is more than 1.0.
The effect of invention
According to the present invention, will be coated on semiconductor substrate and after foring the anti-aging drug of film, by making to contain
The developer solution for having polymer contacts with the resist film, so as to polymer-filled while pattern is formed on the resist film
Between the patterns, thus collapsing for resist can be prevented in development and flushing.In addition, in the present invention, the polymer is
The different types of curable resin of curable resin with forming the resist film, thus can be by dry ecthing and optionally
Only remove resist film.It is possible thereby to carry out forming new fine pattern by the polymer.
Embodiment
In above-mentioned patent document 1 in the prior art, it is by after the resist surface developing liquid developing after exposure, with punching
Washing lotion is rinsed, and with the coating fluid slow rinse liquid containing component of polymer, Resist patterns is coated with component of polymer, then
The method that the component of polymer by replacing forms inversion pattern with dry ecthing removing resist.
But in the above-mentioned methods, when removing resist with developer solution, flushing liquor and forming Resist patterns, Ke Nengyou
Acted in Laplce's power and pattern collapse occurs.
The present invention makes to be connect with the resist surface after the developer solution and mask exposure of polymer comprising the formation of dry ecthing mask
Touch, exposure portion is insoluble in organic solvent in resist, will while unexposed portion is used into developing solution dissolution containing organic solvent
With contained polymer-filled between Resist patterns, so as to prevent collapsing for Resist patterns.Then, will be filled with against corrosion
The surface of agent pattern carries out dry ecthing and removes Resist patterns, and new Resist patterns is formed by the polymer filled.This
It is properly termed as reversion technique.
Resist layer and the polymer of filling are preferably that gaseous species according to used in dry ecthing are different and dry etching rate
The combination of change, such as in the case where using acrylic acid series anticorrosive additive material as resist layer, the polymeric layer of filling
Polymer is preferably using novolac resin (phenol resol resins, naphthol novolac varnish gum or combinations thereof) etc.
Resin, and/or polysiloxane material with high carbon content rate.
The present invention to the resist after exposure with the developer solution comprising polymer by being coated, so as to show unexposed portion
Filled out while shadow between the Resist patterns of developed removing with the polymer that new pattern can be formed in process afterwards
Fill, thus can be filled under conditions of Resist patterns originally is not collapsed, passed through in dry etching process afterwards
Inversion pattern (inverse pattern) and form the fine pattern not collapsed.
Illustrated sequentially for the composition of the composition of the present invention.
The present invention is against corrosion with using in a lithographic process for polymer and organic solvent comprising the formation of dry ecthing mask
Agent developer solution.
Developer solution dissolves above-mentioned dry ecthing mask formation and formed with polymer in organic solvent, and solid constituent is
0.5~20.0 mass % or 1.0~10.0 mass %.Solid constituent refers to remaining after removing organic solvent from developer solution
Ratio.
Above-mentioned dry ecthing mask formation polymer ratio shared in solid constituent is 50~100 mass % or 80
~100 mass %.
The concentration of dry ecthing mask formation polymer in developer solution is 0.5~20.0 mass %.
In the present invention, due to being the developer solution used after the exposure of resist, therefore by upper after mask exposure
The part for stating developer solution removing is unexposed portion.
The formation of dry ecthing mask is the curable resins different from forming the curable resin of resist film with polymer.
Thus, in dry etching process below, by the selected of gaseous species, optionally dry ecthing removing can resist
Agent is lost, and the dry ecthing mask by filling forms and new pattern is formed with polymer.
Wherein, as the solvent for not containing hydroxyl, preferably butyl acetate, the mixed solvent of alcohol and butyl acetate can be enumerated.
It can enumerate for example, by 4- methyl -2- amylalcohols and butyl acetate with 1:99~20:80 mass ratio is obtained by mixing organic molten
Agent.
Furthermore it is possible to enumerate the mixed solvent of propylene glycol monomethyl ether and butyl acetate.It can enumerate for example, propane diols list first
Ether is with butyl acetate with 1:99~20:The organic solvent that 80 mass ratio is obtained by mixing.
As the dry ecthing mask formation polymer contained by developer solution, the curability tree of resist film can be enumerated and formed
The different curable resin of fat.Such as in the case where resist uses acrylic acid series resist, the polymeric layer of filling gathers
Compound is preferably using the tool such as novolac resin (phenol resol resins, naphthol novolac varnish gum or combinations thereof)
There are the resin, and/or polysiloxane material of high carbon content rate.
As novolac resin illustrated below.
The novolac resin of the combination comprising said structure unit or said structure unit can be used.X and y is to rub
That ratio, x:Y=100:0~0:100 or 80~20:20~80 or 70~30:30~70.
The weight average molecular weight of the polymer of construction unit with formula (1) can be 1000~30000 or 2000~
10000 scope.
The following illustrated at least one kind of hydrolysable silanes water being selected from formula (2) can be used as polyorganosiloxane resin
Polysiloxanes obtained by solution condensation.
R1 aSi(R2)4-aFormula (2)
Wherein, R in formula1Represent alkyl, aryl, aralkyl, haloalkyl, halogenated aryl, haloaralkyl, alkenyl or
Person have epoxy radicals, acryloyl group, methylacryloyl, sulfydryl, alkoxy aryl, acyloxy aryl or cyano group organic group,
Or combinations thereof, and pass through Si-C keys and silicon atom bonding, R2Alkoxy, acyloxy or halogen are represented, a represents 0~3
Integer.
The weight average molecular weight of polysiloxanes obtained by least one kind of hydrolysable silanes hydrolytic condensation in formula (2) is 500
~30000 or 800~10000 scope.
Hydrolysis is in the hydrolysis of alkoxysilyl, acyloxysilyl or halosilyl, relative to every
1 mole of water-disintegrable base, use 0.5~100 mole, preferably 1~10 mole of water.
In addition, relative to every 1 mole of water-disintegrable base, 0.001~10 mole can be used, be preferably 0.001~1 mole
Hydrolyst.
Reaction temperature when being hydrolyzed and being condensed is usually 20~80 DEG C.
Hydrolysis can carry out complete hydrolysis, can also partial hydrolysis.That is, in hydrolytic condensate can remaining hydrolysate and/
Or monomer.
Catalyst can be used during hydrolytic condensation.
As hydrolyst, meal chelate compounds, organic acid, inorganic acid, organic base, inorganic base can be enumerated.
Organic acid as hydrolyst can enumerate for example, acetic acid, propionic acid, butyric acid, valeric acid, caproic acid, enanthic acid, pungent
Acid, n-nonanoic acid, capric acid, oxalic acid, maleic acid, methylmalonic acid, adipic acid, decanedioic acid, gallic acid, butyric acid, mellitic acid, peanut
Tetraenoic acid, ミ キ ミ acid, 2 ethyl hexanoic acid, oleic acid, stearic acid, linoleic acid, leukotrienes, salicylic acid, benzoic acid, p-aminophenyl first
Acid, p-methyl benzenesulfonic acid, benzene sulfonic acid, monochloro acetic acid, dichloroacetic acid, trichloroacetic acid, trifluoroacetic acid, formic acid, malonic acid, sulfonic acid, benzene
Dioctyl phthalate, fumaric acid, citric acid, tartaric acid etc..
Inorganic acid as hydrolyst can enumerate for example, hydrochloric acid, nitric acid, sulfuric acid, hydrofluoric acid, phosphoric acid etc..
Organic base as hydrolyst can enumerate for example, pyridine, pyrroles, piperazine, pyrrolidines, piperidines, picoline,
Trimethylamine, triethylamine, MEA, diethanol amine, dimethyl MEA, monomethyl diethanol amine, triethanolamine, diaza
Bicyclooctane, diazabicyclononane, diazabicylo endecatylene, TMAH etc..As inorganic base, can enumerate
For example, ammonia, sodium hydroxide, potassium hydroxide, barium hydroxide, calcium hydroxide etc..In these catalyst, preferred metallo-chelate chemical combination
Thing, organic acid, inorganic acid, these catalyst can be used simultaneously using one kind or two or more.
As the organic solvent used in hydrolysis, can enumerate for example, pentane, isopentane, n-hexane, isohexane, positive heptan
The aliphatic hydrocarbon series solvents such as alkane, isoheptane, 2,2,4- trimethylpentanes, normal octane, isooctane, hexamethylene, hexahydrotoluene；
Benzene,toluene,xylene, ethylbenzene, trimethylbenzene, ethyl methyl benzene, n-propylbenzene, cumene, diethylbenzene, isobutyl-benzene,
The aromatic hydrocarbon series solvents such as triethylbenzene, diisopropyl benzene, n-pentyl naphthalene, trimethylbenzene；Methanol, ethanol, normal propyl alcohol, isopropyl
Alcohol, n-butanol, isobutanol, sec-butyl alcohol, the tert-butyl alcohol, n-amyl alcohol, isoamyl alcohol, 2- methyl butanols, sec-amyl alcohol, tert-pentyl alcohol, 3- methoxies
It is base butanol, n-hexyl alcohol, 2- methyl anyl alcohols, secondary hexyl alcohol, 2- ethyl butanols, secondary enanthol, enanthol -3, n-octyl alcohol, 2-Ethylhexyl Alcohol, secondary
Octanol, n-nonyl alcohol, 2,6- dimethyl enanthol -4, Decanol, secondary tip-nip, Exxal 12, secondary tetradecanol, secondary enanthol,
Phenol, cyclohexanol, methyl cyclohexanol, 3,3,5- cyclonols, amylalcohol, phenylmethylcarbinol, DAA, cresols etc. one
First alcohol series solvent；Ethylene glycol, propane diols, 1,3 butylene glycol, pentanediol -2,4,2 hexylene glycol -2,4, hexylene glycol -2,5, heptan
The polyalcohols such as glycol -2,4,2- ethohexadiols -1,3, diethylene glycol, DPG, triethylene glycol, tripropylene glycol, glycerine
Series solvent；Acetone, MEK, methyl-n-propyl ketone, methyl-normal-butyl ketone, metacetone, methyl-isobutyl ketone, methyl-just
Amyl ketone, ethyl-normal-butyl ketone, methyl-n-hexyl ketone, DIBK, trimethyl nonanone, cyclohexanone, methyl cyclohexanone, 2,
The ketone series solvents such as 4- pentanediones, pentanedione, DAA, acetyl benzophenone, fenchone；Ether, isopropyl ether, n-butyl ether, just oneself
Ether, 2- ethylhexyls ether, oxirane, 1,2 epoxy prapane, dioxolanes, 4- methyl dioxolanes, dioxane, dimethyl twoAlkane, glycol monoethyl ether, ethylene glycol monomethyl ether, ethylene glycol Anaesthetie Ether, ethylene glycol list-n-butyl ether, ethylene glycol list-
N-hexyl ether, ethylene glycol list phenyl ether, ethylene glycol list -2- ethyl-butyls ether, ethylene glycol dibutyl ethers, diethylene glycol monomethyl ether,
TC, diethylene glycol diethyl ether, diethylene glycol list-n-butyl ether, diethylene glycol di-n-butyl ether, diethyl
Glycol list-n-hexyl ether, ethoxy triglycol, tetraethylene glycol di-n-butyl ether, propylene glycol monomethyl ether, propylene glycol monoethyl,
Propylene glycol monopropyl ether, glycol monobutyl ether, propylene glycol monomethyl ether,
4- methyl -2- amylalcohols, dipropylene glycol monomethyl ether, dihydroxypropane single-ethyl ether, DPG list propyl ether, dipropyl two
The ether series solvents such as alcohol single-butyl ether, tripropylene glycol monomethyl ether, tetrahydrofuran, 2- methyltetrahydrofurans；Diethyl carbonate, acetic acid
Methyl esters, ethyl acetate, gamma-butyrolacton, gamma-valerolactone, n-propyl acetate, isopropyl acetate, n-butyl acetate, Sucrose Acetate
Ester, sec-butyl acetate, n-amyl acetate, sec-amyl acetate, acetic acid 3- methoxybutyls, methyl amyl acetate, acetic acid 2- ethyls
Butyl ester, acetic acid 2- ethylhexyls, benzyl acetate, cyclohexyl acetate, methylcyclohexyl acetate, n-nonyl acetate, acetoacetate first
Ester, ethyl acetoacetate, ethylene glycol monomethyl ether acetate, ethylene glycol monomethyl ether acetate, diethylene glycol monomethyl ether acetic acid esters,
TC acetic acid esters, diethylene glycol list-n-butyl ether acetic acid esters, propylene glycol methyl ether acetate, propane diols list
Monoethyl ether acetate, propylene glycol monopropyl ether acetic acid esters, glycol monobutyl ether acetic acid esters, dipropylene glycol monomethyl ether acetic acid esters,
Dihydroxypropane single-ethyl ether acetic acid esters, diacetate glycol ester, acetic acid methoxy triglycol, ethyl propionate, n-butyl propionate, third
Isoamyl valerate, diethy-aceto oxalate, dibutyl oxalate, methyl lactate, ethyl lactate, n-butyl lactate, N_amyl lactate, the third two
The ester series solvents such as diethyl phthalate, rutgers, diethyl phthalate；N-METHYLFORMAMIDE, N, N- dimethyl formyls
Amine, N, N- diethylformamides, acetamide, N- methylacetamides, DMAC N,N' dimethyl acetamide, N- methyl propanamides, N- methyl
The nitrogenous series solvent such as pyrrolidones；Dimethyl sulfide, diethyl thioether, thiophene, thiophane, dimethyl sulfoxide (DMSO), sulfolane, 1,
Sulfur-bearing series solvent such as 3- propane sultones etc..These solvents can use a kind, or two or more is applied in combination.
As the polysiloxanes, such as illustrated below.
X and y is mol ratio, can enumerate x:Y=100:0~0:100 or 80~20:20~80 or 70~30:30~70.
The present invention is a kind of manufacture method of semiconductor device, including following process (A)~process (C)：Process (A),
Resist is coated on semiconductor substrate and forms resist layer, and is exposed；Process (B), make the surface of the resist layer with
Developer solution contact described in any one of the viewpoint of 1st viewpoint~the 7th, forms polymeric layer between Resist patterns；Process
(C) resist layer, is removed by dry ecthing, forms the inversion pattern as caused by the polymer.
As the anticorrosive additive material used in process (A), can enumerate the resin such as with polymethacrylates into
The resist divided.Resist Solution is carried out for 0.5~5 minute with 70.0~150.0 DEG C of baking temperature, baking time after coating
Baking, scope of the resist thickness in 10~1000nm obtain.Resist Solution, developer solution and/or coating material as shown below,
It can be coated by spin-coating method, infusion process, gunite etc., but particularly preferred spin-coating method.The exposure of resist is covered by defined
Mould is exposed.Exposure can use KrF PRKs (wavelength 248nm), ArF PRKs (wavelength 193nm) and EUV
Light (wavelength 13.5nm), electron beam etc..After exposure, (PEB is heated after being exposed as needed：Post Exposure
Bake).Heating suitably selects from 70 DEG C~150 DEG C of heating-up temperature, 0.3~10 minute heat time after exposure.
The formation of the resist of process (A) can form resist lower membrane on a semiconductor substrate, be formed on resisting
Lose agent.
The formation of the resist of process (A) can form organic lower membrane on a semiconductor substrate, then be formed on
The hard mask of silicon, then it is formed on resist.
The resist lower membrane used in above-mentioned operation (A) is for preventing the diffusing reflection during anti-aging drug of upper strata
, in addition, being used to improve the adaptation with resist, such as acrylic resin, novolaks can be used
It is resin.Resist lower membrane can form 1~1000nm of thickness envelope on a semiconductor substrate.
The organic underlayer film used in addition in above-mentioned operation (A) is the hard mask for having used organic resin, and carbon can be used
The material that content is high and hydrogen content is low.Such as polyvinylnaphthaleneand system resin, Carbazole Novolak Resin, phenol novolacs tree
Fat, naphthol novolac varnish gum etc..These materials can form envelope with 5~1000nm of thickness on a semiconductor substrate.
Additionally as the hard mask of the silicon used in above-mentioned operation (A), can use as above-mentioned polysiloxanes tree
Fat and in polysiloxanes obtained by the illustrated below at least one kind of hydrolysable silanes hydrolysis being selected from formula (2).Example can be illustrated
Such as, tetraethoxysilane, MTMS and polysiloxanes obtained by phenyl triethoxysilane hydrolysis.These are poly-
Siloxanes can form envelope on above-mentioned organic underlayer film with 5~200nm of thickness.
In process (B), the polymer for forming dry ecthing mask formation polymeric layer can be heated and formed.Add
Heat can be with the progress 0.5~5 minute of 50~180 DEG C of baking temperature.
In process (C), dry ecthing can use tetrafluoromethane, Freon C318 (C4F8), perfluoropropane (C3F8), three
The gases such as fluoromethane, carbon monoxide, argon gas, oxygen, nitrogen, sulfur hexafluoride, difluoromethane, Nitrogen trifluoride and chlorine trifluoride.By
This removes Resist patterns originally, is formed and forms the reversion figure caused by polymer as dry ecthing mask contained in developer solution
Case.
Embodiment
Synthesis example 1
Make naphthol novolac varnish gum (with 1- naphthols:Phenol=50:50 mol ratio and formaldehyde react and to synthesize phenolic aldehyde clear
Coating resins.Weight average molecular weight is that 3200) 3g is dissolved in propylene glycol monomethyl ether 3.88g, butyl acetate 93.12g, is obtained comprising dry
The developer solution of etching mask formation polymer.
Synthesis example 2
Make containing silicone resin (with methacrylic acid 3- trimethoxy-silylpropyl esters：MTES=20:
80 mixed in molar ratio, the silane of mixing is hydrolyzed and is condensed, obtains polyorganosiloxane resin.26000) weight average molecular weight is
3g is dissolved in 4- methyl -2- amylalcohols 3.88g, butyl acetate 93.12g, is obtained comprising dry ecthing mask formation polymer
Developer solution.
(being formed by the displacement in the unexposed portion of resist and the pattern of dry ecthing)
Embodiment 1
On a silicon substrate by resist lower membrane (commercially available product, resin component are polymethacrylates) using spinner with
Thickness 80nm is film-made, and using spinner coating ArF Resist Solutions, (commercially available product, resin component are poly- methyl-prop on the film
Olefin(e) acid ester).Heated 60 seconds with 100 DEG C on electric hot plate, so as to form thickness 100nm resist film.Swashed using ArF quasi-molecules
Light is exposed with defined condition with exposure device (NIKON societies system, S307E).The line width of purpose be 65nm lines and
Every, after exposure with 105 DEG C carry out 60 seconds heating (PEB), be cooled to room temperature on the cooling plate.By the developer solution of the gained of synthesis example 1
Soak and put on resist film, stand 60 seconds, make within 60 seconds solvent centrifugal dehydration with 1500 revs/min of centrifugations, and then by synthesis example 1
Developer solution leaching is put and stands 5 seconds, and carrying out within 60 seconds pattern with 1500 revs/min of centrifugations forms putting for film and the unexposed portion of resist
Change.
The presence or absence of the displacement in the unexposed portion of resist is observed by section SEM to judge.
Embodiment 2
In above-described embodiment 1, the developer solution of synthesis example 1 is replaced using the developer solution of synthesis example 2, in addition similarly
Carry out.
Comparative example 1
In above-described embodiment 1, developer solution that spin coating is only made up of organic solvent, then using the developer solution of embodiment 1,
In addition, carry out similarly to Example 1.
In table 1, as forming commenting for caused by the developer solution of the polymer imbedibility of polymer comprising dry ecthing mask
Valency is, using in the observation by the use of section SEM pattern form good situation as " good ", pattern is formed bad or not had
The situation of pattern is formed as "None".
The evaluation of the presence or absence of pattern collapse is, using pattern-free collapses in the observation by the use of section SEM situation as
"None", the situation of pattern collapse will occur as " having ".
Table 1
The film be embedded in embodiment 2 is formed by the pattern of dry ecthing.Carry out using CF4As etching gas
Dry ecthing, expose Resist patterns top.Finally, carry out using O2As the dry ecthing of etching gas, remove resist and
Obtain pattern.Together with Resist patterns, at least one of resist lower membrane is etched.
Industry utilizability
Fine Resist patterns is formed pattern collapse can not occur, so as in highly integrated semiconductor dress
Used in the manufacture put.
Claims (10)
1. a kind of manufacture method of semiconductor device, including following process (A)~process (C)：Process (A), in semiconductor substrate
It is upper to coat resist and form resist film, and be exposed；Process (B), make the surface of the resist film and contain dry ecthing
The developer solution of mask formation polymer and organic solvent contacts, and is filled between the pattern of the developed resist film eliminated
The polymer；Process (C), by dry ecthing from be filled with the polymer resist film remove resist, formed by
Inversion pattern caused by the polymer,
The developer solution is developer solution use in a lithographic process, for forming inversion pattern, and the polymer is phenolic aldehyde
Varnish gum or make be selected from formula (2) at least one kind of hydrolysable silanes hydrolytic condensation obtained by polysiloxanes,
R1 aSi(R2)4-aFormula (2)
Wherein, R in formula1Represent alkyl, aryl, aralkyl, haloalkyl, halogenated aryl, haloaralkyl, alkenyl or have
Epoxy radicals, acryloyl group, methylacryloyl, sulfydryl, alkoxy aryl, acyloxy aryl or the organic group of cyano group or they
Combination, and R1Pass through Si-C keys and silicon atom bonding, R2Alkoxy, acyloxy or halogen are represented, a represents 0~3 integer.
2. the manufacture method of semiconductor device according to claim 1, the polymer is the tree with forming resist film
The different polymer of fat composition.
3. the manufacture method of semiconductor device according to claim 1 or 2, the developer solution resist film exposure it
After use.
4. the manufacture method of semiconductor device according to claim 1 or 2, the organic solvent in the developer solution is acetic acid
The mixed solvent of butyl ester or butyl acetate and alcohol.
5. the manufacture method of semiconductor device according to claim 1 or 2, the organic solvent in the developer solution is 2- penta
The mixed solvent of ketone or 2 pentanone and alcohol.
6. the manufacture method of semiconductor device according to claim 1 or 2, the polymer in the developer solution it is dense
Spend for 0.5~20 weight %.
7. the manufacture method of semiconductor device according to claim 1 or 2, the shape of the resist film in the process (A)
Into being by forming resist lower membrane on a semiconductor substrate, then form resist film in resist lower membrane and carry out
's.
8. the manufacture method of semiconductor device according to claim 1 or 2, the shape of the resist film in the process (A)
Into be by forming organic lower membrane on a semiconductor substrate, then on organic underlayer film formed silicon atoms hard mask,
Form resist film on the hard mask again and carry out.
9. the manufacture method of semiconductor device according to claim 1 or 2, in the process (B), the polymeric layer
Formation include apply heat process.
10. the manufacture method of semiconductor device according to claim 1 or 2, in the process (C), resist/polymerization
The dry etching rate ratio of thing is more than 1.0.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2011066290 | 2011-03-24 | ||
| JP066290/2011 | 2011-03-24 | ||
| PCT/JP2012/057019 WO2012128251A1 (en) | 2011-03-24 | 2012-03-19 | Polymer-containing developer |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN103460138A CN103460138A (en) | 2013-12-18 |
| CN103460138B true CN103460138B (en) | 2018-02-09 |
Family
ID=
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5262283A (en) * | 1990-04-27 | 1993-11-16 | Siemens Aktiengesellschaft | Method for producing a resist structure |
| CN1342920A (en) * | 2000-09-10 | 2002-04-03 | 富士写真胶片株式会社 | Silver halides photochromy sensitive material and image forming method |
| US6511792B2 (en) * | 2000-02-28 | 2003-01-28 | Mitsubishi Denki Kabushiki Kaisha | Developing process, process for forming pattern and process for preparing semiconductor device using same |
| CN1823303A (en) * | 2003-07-14 | 2006-08-23 | Az电子材料（日本）株式会社 | Developing solution for photosensitive composition and method for forming patterned resist film |
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5262283A (en) * | 1990-04-27 | 1993-11-16 | Siemens Aktiengesellschaft | Method for producing a resist structure |
| US6511792B2 (en) * | 2000-02-28 | 2003-01-28 | Mitsubishi Denki Kabushiki Kaisha | Developing process, process for forming pattern and process for preparing semiconductor device using same |
| CN1342920A (en) * | 2000-09-10 | 2002-04-03 | 富士写真胶片株式会社 | Silver halides photochromy sensitive material and image forming method |
| CN1823303A (en) * | 2003-07-14 | 2006-08-23 | Az电子材料（日本）株式会社 | Developing solution for photosensitive composition and method for forming patterned resist film |
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