JP7269904B6 - ケイ素含有下層 - Google Patents
ケイ素含有下層 Download PDFInfo
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- JP7269904B6 JP7269904B6 JP2020116081A JP2020116081A JP7269904B6 JP 7269904 B6 JP7269904 B6 JP 7269904B6 JP 2020116081 A JP2020116081 A JP 2020116081A JP 2020116081 A JP2020116081 A JP 2020116081A JP 7269904 B6 JP7269904 B6 JP 7269904B6
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- Prior art keywords
- acid
- alkyl
- moiety
- aryl
- formula
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- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 title claims description 94
- 229910052710 silicon Inorganic materials 0.000 title claims description 94
- 239000010703 silicon Substances 0.000 title claims description 92
- 239000000178 monomer Substances 0.000 claims description 152
- -1 acenaphthyl Chemical group 0.000 claims description 118
- 229920000642 polymer Polymers 0.000 claims description 94
- 125000003118 aryl group Chemical group 0.000 claims description 83
- 239000000203 mixture Substances 0.000 claims description 76
- 125000000217 alkyl group Chemical group 0.000 claims description 73
- 239000010410 layer Substances 0.000 claims description 67
- 229910052799 carbon Inorganic materials 0.000 claims description 64
- 229910052739 hydrogen Inorganic materials 0.000 claims description 54
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 44
- 239000000758 substrate Substances 0.000 claims description 42
- 229910001868 water Inorganic materials 0.000 claims description 42
- 229910052736 halogen Inorganic materials 0.000 claims description 41
- 150000002367 halogens Chemical class 0.000 claims description 41
- 239000002253 acid Substances 0.000 claims description 39
- 229920000620 organic polymer Polymers 0.000 claims description 36
- 230000002378 acidificating effect Effects 0.000 claims description 34
- 125000001183 hydrocarbyl group Chemical group 0.000 claims description 28
- 238000000034 method Methods 0.000 claims description 27
- 229920002120 photoresistant polymer Polymers 0.000 claims description 25
- 125000003545 alkoxy group Chemical group 0.000 claims description 21
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 21
- 125000004432 carbon atom Chemical group C* 0.000 claims description 21
- 125000005647 linker group Chemical group 0.000 claims description 20
- 239000011247 coating layer Substances 0.000 claims description 19
- 125000005842 heteroatom Chemical group 0.000 claims description 18
- 239000011248 coating agent Substances 0.000 claims description 17
- 238000000576 coating method Methods 0.000 claims description 17
- 239000002904 solvent Substances 0.000 claims description 14
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims description 13
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 13
- 125000001188 haloalkyl group Chemical class 0.000 claims description 12
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 11
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 8
- 125000003358 C2-C20 alkenyl group Chemical group 0.000 claims description 7
- 125000005027 hydroxyaryl group Chemical group 0.000 claims description 7
- 125000004104 aryloxy group Chemical group 0.000 claims description 6
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 5
- 125000001624 naphthyl group Chemical group 0.000 claims description 5
- 150000003839 salts Chemical class 0.000 claims description 5
- 125000003396 thiol group Chemical group [H]S* 0.000 claims description 5
- 125000002178 anthracenyl group Chemical group C1(=CC=CC2=CC3=CC=CC=C3C=C12)* 0.000 claims description 4
- 125000001725 pyrenyl group Chemical group 0.000 claims description 4
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims description 3
- 229910003849 O-Si Inorganic materials 0.000 claims description 3
- 229910003872 O—Si Inorganic materials 0.000 claims description 3
- 125000002843 carboxylic acid group Chemical group 0.000 claims description 3
- 125000005561 phenanthryl group Chemical group 0.000 claims description 3
- 125000000641 acridinyl group Chemical group C1(=CC=CC2=NC3=CC=CC=C3C=C12)* 0.000 claims description 2
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 claims description 2
- 125000003336 coronenyl group Chemical group C1(=CC2=CC=C3C=CC4=CC=C5C=CC6=CC=C1C1=C6C5=C4C3=C21)* 0.000 claims description 2
- 125000005509 dibenzothiophenyl group Chemical group 0.000 claims description 2
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 2
- 125000002541 furyl group Chemical group 0.000 claims description 2
- 125000001041 indolyl group Chemical group 0.000 claims description 2
- 125000003933 pentacenyl group Chemical group C1(=CC=CC2=CC3=CC4=CC5=CC=CC=C5C=C4C=C3C=C12)* 0.000 claims description 2
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 claims description 2
- 125000004076 pyridyl group Chemical group 0.000 claims description 2
- 125000003011 styrenyl group Chemical group [H]\C(*)=C(/[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 2
- 125000001935 tetracenyl group Chemical group C1(=CC=CC2=CC3=CC4=CC=CC=C4C=C3C=C12)* 0.000 claims description 2
- 125000001544 thienyl group Chemical group 0.000 claims description 2
- 125000003944 tolyl group Chemical group 0.000 claims description 2
- 125000003960 triphenylenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C3=CC=CC=C3C12)* 0.000 claims description 2
- 125000005023 xylyl group Chemical group 0.000 claims description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims 2
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims 1
- ZADPBFCGQRWHPN-UHFFFAOYSA-N boronic acid Chemical compound OBO ZADPBFCGQRWHPN-UHFFFAOYSA-N 0.000 claims 1
- 125000005462 imide group Chemical group 0.000 claims 1
- 125000000686 lactone group Chemical group 0.000 claims 1
- LNOPIUAQISRISI-UHFFFAOYSA-N n'-hydroxy-2-propan-2-ylsulfonylethanimidamide Chemical compound CC(C)S(=O)(=O)CC(N)=NO LNOPIUAQISRISI-UHFFFAOYSA-N 0.000 claims 1
- BUUPQKDIAURBJP-UHFFFAOYSA-N sulfinic acid Chemical compound OS=O BUUPQKDIAURBJP-UHFFFAOYSA-N 0.000 claims 1
- 230000005494 condensation Effects 0.000 description 56
- 238000009833 condensation Methods 0.000 description 54
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 33
- 238000001723 curing Methods 0.000 description 24
- JOLQKTGDSGKSKJ-UHFFFAOYSA-N 1-ethoxypropan-2-ol Chemical compound CCOCC(C)O JOLQKTGDSGKSKJ-UHFFFAOYSA-N 0.000 description 18
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 18
- 239000000243 solution Substances 0.000 description 17
- 235000012431 wafers Nutrition 0.000 description 17
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 16
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 15
- 229910052760 oxygen Inorganic materials 0.000 description 15
- 239000001301 oxygen Substances 0.000 description 15
- 150000003254 radicals Chemical class 0.000 description 15
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 14
- WGTYBPLFGIVFAS-UHFFFAOYSA-M tetramethylammonium hydroxide Chemical compound [OH-].C[N+](C)(C)C WGTYBPLFGIVFAS-UHFFFAOYSA-M 0.000 description 14
- 150000002596 lactones Chemical group 0.000 description 12
- 125000001424 substituent group Chemical group 0.000 description 12
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 11
- 239000000463 material Substances 0.000 description 11
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 description 10
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 10
- 239000007787 solid Substances 0.000 description 10
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 9
- 229910052782 aluminium Inorganic materials 0.000 description 9
- 239000011203 carbon fibre reinforced carbon Substances 0.000 description 9
- 229910052757 nitrogen Inorganic materials 0.000 description 9
- 239000004065 semiconductor Substances 0.000 description 9
- ARXJGSRGQADJSQ-UHFFFAOYSA-N 1-methoxypropan-2-ol Chemical compound COCC(C)O ARXJGSRGQADJSQ-UHFFFAOYSA-N 0.000 description 8
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 8
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 8
- 150000001241 acetals Chemical group 0.000 description 8
- 238000005227 gel permeation chromatography Methods 0.000 description 8
- 239000003381 stabilizer Substances 0.000 description 8
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 8
- 239000004793 Polystyrene Substances 0.000 description 7
- BOTDANWDWHJENH-UHFFFAOYSA-N Tetraethyl orthosilicate Chemical compound CCO[Si](OCC)(OCC)OCC BOTDANWDWHJENH-UHFFFAOYSA-N 0.000 description 7
- 125000001931 aliphatic group Chemical group 0.000 description 7
- 150000001735 carboxylic acids Chemical class 0.000 description 7
- 238000005530 etching Methods 0.000 description 7
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 7
- 229920002223 polystyrene Polymers 0.000 description 7
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 7
- NGSWKAQJJWESNS-UHFFFAOYSA-N 4-coumaric acid Chemical compound OC(=O)C=CC1=CC=C(O)C=C1 NGSWKAQJJWESNS-UHFFFAOYSA-N 0.000 description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 6
- 150000001875 compounds Chemical class 0.000 description 6
- 125000004122 cyclic group Chemical group 0.000 description 6
- KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical class [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 description 6
- LZCLXQDLBQLTDK-UHFFFAOYSA-N ethyl 2-hydroxypropanoate Chemical compound CCOC(=O)C(C)O LZCLXQDLBQLTDK-UHFFFAOYSA-N 0.000 description 6
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 6
- 238000006460 hydrolysis reaction Methods 0.000 description 6
- 239000003960 organic solvent Substances 0.000 description 6
- 125000004430 oxygen atom Chemical group O* 0.000 description 6
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 6
- SJMYWORNLPSJQO-UHFFFAOYSA-N tert-butyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OC(C)(C)C SJMYWORNLPSJQO-UHFFFAOYSA-N 0.000 description 6
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 5
- 150000007513 acids Chemical class 0.000 description 5
- 125000000304 alkynyl group Chemical group 0.000 description 5
- 229910021529 ammonia Inorganic materials 0.000 description 5
- 239000007864 aqueous solution Substances 0.000 description 5
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 5
- 239000011541 reaction mixture Substances 0.000 description 5
- 238000012546 transfer Methods 0.000 description 5
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 description 4
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 4
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 4
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 4
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 4
- 125000005620 boronic acid group Chemical class 0.000 description 4
- 239000003054 catalyst Substances 0.000 description 4
- HNEGQIOMVPPMNR-IHWYPQMZSA-N citraconic acid Chemical compound OC(=O)C(/C)=C\C(O)=O HNEGQIOMVPPMNR-IHWYPQMZSA-N 0.000 description 4
- 229940018557 citraconic acid Drugs 0.000 description 4
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 4
- 238000009472 formulation Methods 0.000 description 4
- 239000001530 fumaric acid Substances 0.000 description 4
- 229910052732 germanium Inorganic materials 0.000 description 4
- 230000007062 hydrolysis Effects 0.000 description 4
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 4
- 239000011976 maleic acid Substances 0.000 description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
- LVHBHZANLOWSRM-UHFFFAOYSA-N methylenebutanedioic acid Natural products OC(=O)CC(=C)C(O)=O LVHBHZANLOWSRM-UHFFFAOYSA-N 0.000 description 4
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 4
- 210000002381 plasma Anatomy 0.000 description 4
- 238000001020 plasma etching Methods 0.000 description 4
- 238000004528 spin coating Methods 0.000 description 4
- 150000003460 sulfonic acids Chemical class 0.000 description 4
- 229910052717 sulfur Inorganic materials 0.000 description 4
- 239000011593 sulfur Substances 0.000 description 4
- LDHQCZJRKDOVOX-UHFFFAOYSA-N trans-crotonic acid Natural products CC=CC(O)=O LDHQCZJRKDOVOX-UHFFFAOYSA-N 0.000 description 4
- WBYWAXJHAXSJNI-VOTSOKGWSA-M .beta-Phenylacrylic acid Natural products [O-]C(=O)\C=C\C1=CC=CC=C1 WBYWAXJHAXSJNI-VOTSOKGWSA-M 0.000 description 3
- WNXJIVFYUVYPPR-UHFFFAOYSA-N 1,3-dioxolane Chemical compound C1COCO1 WNXJIVFYUVYPPR-UHFFFAOYSA-N 0.000 description 3
- JAHNSTQSQJOJLO-UHFFFAOYSA-N 2-(3-fluorophenyl)-1h-imidazole Chemical compound FC1=CC=CC(C=2NC=CN=2)=C1 JAHNSTQSQJOJLO-UHFFFAOYSA-N 0.000 description 3
- XUDBVJCTLZTSDC-UHFFFAOYSA-N 2-ethenylbenzoic acid Chemical compound OC(=O)C1=CC=CC=C1C=C XUDBVJCTLZTSDC-UHFFFAOYSA-N 0.000 description 3
- QXKNDUSXGFIHHU-UHFFFAOYSA-N 2-methylcyclopentene-1-carboxylic acid Chemical compound CC1=C(C(O)=O)CCC1 QXKNDUSXGFIHHU-UHFFFAOYSA-N 0.000 description 3
- PSZAEHPBBUYICS-UHFFFAOYSA-N 2-methylidenepropanedioic acid Chemical compound OC(=O)C(=C)C(O)=O PSZAEHPBBUYICS-UHFFFAOYSA-N 0.000 description 3
- XDLMVUHYZWKMMD-UHFFFAOYSA-N 3-trimethoxysilylpropyl 2-methylprop-2-enoate Chemical compound CO[Si](OC)(OC)CCCOC(=O)C(C)=C XDLMVUHYZWKMMD-UHFFFAOYSA-N 0.000 description 3
- NGSWKAQJJWESNS-ZZXKWVIFSA-M 4-Hydroxycinnamate Natural products OC1=CC=C(\C=C\C([O-])=O)C=C1 NGSWKAQJJWESNS-ZZXKWVIFSA-M 0.000 description 3
- DFYRUELUNQRZTB-UHFFFAOYSA-N Acetovanillone Natural products COC1=CC(C(C)=O)=CC=C1O DFYRUELUNQRZTB-UHFFFAOYSA-N 0.000 description 3
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 3
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 3
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 3
- 239000004215 Carbon black (E152) Substances 0.000 description 3
- WBYWAXJHAXSJNI-SREVYHEPSA-N Cinnamic acid Chemical compound OC(=O)\C=C/C1=CC=CC=C1 WBYWAXJHAXSJNI-SREVYHEPSA-N 0.000 description 3
- NMEZJSDUZQOPFE-UHFFFAOYSA-N Cyclohex-1-enecarboxylic acid Chemical compound OC(=O)C1=CCCCC1 NMEZJSDUZQOPFE-UHFFFAOYSA-N 0.000 description 3
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-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
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 3
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 3
- NOZAQBYNLKNDRT-UHFFFAOYSA-N [diacetyloxy(ethenyl)silyl] acetate Chemical compound CC(=O)O[Si](OC(C)=O)(OC(C)=O)C=C NOZAQBYNLKNDRT-UHFFFAOYSA-N 0.000 description 3
- 125000003342 alkenyl group Chemical group 0.000 description 3
- 125000002947 alkylene group Chemical group 0.000 description 3
- 125000004429 atom Chemical group 0.000 description 3
- 239000002585 base Substances 0.000 description 3
- 229910052796 boron Inorganic materials 0.000 description 3
- 150000001721 carbon Chemical group 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 229930016911 cinnamic acid Natural products 0.000 description 3
- 235000013985 cinnamic acid Nutrition 0.000 description 3
- LDHQCZJRKDOVOX-NSCUHMNNSA-N crotonic acid Chemical compound C\C=C\C(O)=O LDHQCZJRKDOVOX-NSCUHMNNSA-N 0.000 description 3
- PYRZPBDTPRQYKG-UHFFFAOYSA-N cyclopentene-1-carboxylic acid Chemical compound OC(=O)C1=CCCC1 PYRZPBDTPRQYKG-UHFFFAOYSA-N 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 229940116333 ethyl lactate Drugs 0.000 description 3
- 125000001153 fluoro group Chemical group F* 0.000 description 3
- GNPVGFCGXDBREM-UHFFFAOYSA-N germanium atom Chemical compound [Ge] GNPVGFCGXDBREM-UHFFFAOYSA-N 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- BHEPBYXIRTUNPN-UHFFFAOYSA-N hydridophosphorus(.) (triplet) Chemical group [PH] BHEPBYXIRTUNPN-UHFFFAOYSA-N 0.000 description 3
- 229930195733 hydrocarbon Natural products 0.000 description 3
- 125000006289 hydroxybenzyl group Chemical group 0.000 description 3
- 125000004464 hydroxyphenyl group Chemical group 0.000 description 3
- 239000004615 ingredient Substances 0.000 description 3
- 239000003999 initiator Substances 0.000 description 3
- 229910052500 inorganic mineral Inorganic materials 0.000 description 3
- KKSDGJDHHZEWEP-UHFFFAOYSA-N m-hydroxycinnamic acid Natural products OC(=O)C=CC1=CC=CC(O)=C1 KKSDGJDHHZEWEP-UHFFFAOYSA-N 0.000 description 3
- WBYWAXJHAXSJNI-UHFFFAOYSA-N methyl p-hydroxycinnamate Natural products OC(=O)C=CC1=CC=CC=C1 WBYWAXJHAXSJNI-UHFFFAOYSA-N 0.000 description 3
- 239000011707 mineral Substances 0.000 description 3
- 125000002868 norbornyl group Chemical group C12(CCC(CC1)C2)* 0.000 description 3
- PMOWTIHVNWZYFI-UHFFFAOYSA-N o-Coumaric acid Natural products OC(=O)C=CC1=CC=CC=C1O PMOWTIHVNWZYFI-UHFFFAOYSA-N 0.000 description 3
- LQVYKEXVMZXOAH-UHFFFAOYSA-N oct-4-enedioic acid Chemical compound OC(=O)CCC=CCCC(O)=O LQVYKEXVMZXOAH-UHFFFAOYSA-N 0.000 description 3
- 150000003009 phosphonic acids Chemical class 0.000 description 3
- 238000006116 polymerization reaction Methods 0.000 description 3
- UIIIBRHUICCMAI-UHFFFAOYSA-N prop-2-ene-1-sulfonic acid Chemical compound OS(=O)(=O)CC=C UIIIBRHUICCMAI-UHFFFAOYSA-N 0.000 description 3
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- LLHKCFNBLRBOGN-UHFFFAOYSA-N propylene glycol methyl ether acetate Chemical compound COCC(C)OC(C)=O LLHKCFNBLRBOGN-UHFFFAOYSA-N 0.000 description 3
- 238000012958 reprocessing Methods 0.000 description 3
- 229920006395 saturated elastomer Polymers 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 125000003107 substituted aryl group Chemical group 0.000 description 3
- 239000004094 surface-active agent Substances 0.000 description 3
- NHGXDBSUJJNIRV-UHFFFAOYSA-M tetrabutylammonium chloride Chemical compound [Cl-].CCCC[N+](CCCC)(CCCC)CCCC NHGXDBSUJJNIRV-UHFFFAOYSA-M 0.000 description 3
- PMOWTIHVNWZYFI-AATRIKPKSA-N trans-2-coumaric acid Chemical compound OC(=O)\C=C\C1=CC=CC=C1O PMOWTIHVNWZYFI-AATRIKPKSA-N 0.000 description 3
- KKSDGJDHHZEWEP-SNAWJCMRSA-N trans-3-coumaric acid Chemical compound OC(=O)\C=C\C1=CC=CC(O)=C1 KKSDGJDHHZEWEP-SNAWJCMRSA-N 0.000 description 3
- ZNOCGWVLWPVKAO-UHFFFAOYSA-N trimethoxy(phenyl)silane Chemical compound CO[Si](OC)(OC)C1=CC=CC=C1 ZNOCGWVLWPVKAO-UHFFFAOYSA-N 0.000 description 3
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- 125000000626 sulfinic acid group Chemical class 0.000 description 1
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- YNJQKNVVBBIPBA-UHFFFAOYSA-M tetrabutylazanium;trifluoromethanesulfonate Chemical compound [O-]S(=O)(=O)C(F)(F)F.CCCC[N+](CCCC)(CCCC)CCCC YNJQKNVVBBIPBA-UHFFFAOYSA-M 0.000 description 1
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- MRYQZMHVZZSQRT-UHFFFAOYSA-M tetramethylazanium;acetate Chemical compound CC([O-])=O.C[N+](C)(C)C MRYQZMHVZZSQRT-UHFFFAOYSA-M 0.000 description 1
- WWIYWFVQZQOECA-UHFFFAOYSA-M tetramethylazanium;formate Chemical compound [O-]C=O.C[N+](C)(C)C WWIYWFVQZQOECA-UHFFFAOYSA-M 0.000 description 1
- MANNXDXMUHZSRP-UHFFFAOYSA-M tetramethylazanium;trifluoromethanesulfonate Chemical compound C[N+](C)(C)C.[O-]S(=O)(=O)C(F)(F)F MANNXDXMUHZSRP-UHFFFAOYSA-M 0.000 description 1
- 150000003568 thioethers Chemical class 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- 210000001519 tissue Anatomy 0.000 description 1
- MAKDTFFYCIMFQP-UHFFFAOYSA-N titanium tungsten Chemical compound [Ti].[W] MAKDTFFYCIMFQP-UHFFFAOYSA-N 0.000 description 1
- WOZZOSDBXABUFO-UHFFFAOYSA-N tri(butan-2-yloxy)alumane Chemical compound [Al+3].CCC(C)[O-].CCC(C)[O-].CCC(C)[O-] WOZZOSDBXABUFO-UHFFFAOYSA-N 0.000 description 1
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- DOEHJNBEOVLHGL-UHFFFAOYSA-N trichloro(propyl)silane Chemical compound CCC[Si](Cl)(Cl)Cl DOEHJNBEOVLHGL-UHFFFAOYSA-N 0.000 description 1
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- RAVSYXWWBIFQEV-UHFFFAOYSA-N tricyclopentyl borate Chemical compound C1CCCC1OB(OC1CCCC1)OC1CCCC1 RAVSYXWWBIFQEV-UHFFFAOYSA-N 0.000 description 1
- DENFJSAFJTVPJR-UHFFFAOYSA-N triethoxy(ethyl)silane Chemical compound CCO[Si](CC)(OCC)OCC DENFJSAFJTVPJR-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
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- HQYALQRYBUJWDH-UHFFFAOYSA-N trimethoxy(propyl)silane Chemical compound CCC[Si](OC)(OC)OC HQYALQRYBUJWDH-UHFFFAOYSA-N 0.000 description 1
- UAEJRRZPRZCUBE-UHFFFAOYSA-N trimethoxyalumane Chemical compound [Al+3].[O-]C.[O-]C.[O-]C UAEJRRZPRZCUBE-UHFFFAOYSA-N 0.000 description 1
- WRECIMRULFAWHA-UHFFFAOYSA-N trimethyl borate Chemical compound COB(OC)OC WRECIMRULFAWHA-UHFFFAOYSA-N 0.000 description 1
- JLPJTCGUKOBWRJ-UHFFFAOYSA-N tripentyl borate Chemical compound CCCCCOB(OCCCCC)OCCCCC JLPJTCGUKOBWRJ-UHFFFAOYSA-N 0.000 description 1
- OPSWAWSNPREEFQ-UHFFFAOYSA-K triphenoxyalumane Chemical compound [Al+3].[O-]C1=CC=CC=C1.[O-]C1=CC=CC=C1.[O-]C1=CC=CC=C1 OPSWAWSNPREEFQ-UHFFFAOYSA-K 0.000 description 1
- MDCWDBMBZLORER-UHFFFAOYSA-N triphenyl borate Chemical compound C=1C=CC=CC=1OB(OC=1C=CC=CC=1)OC1=CC=CC=C1 MDCWDBMBZLORER-UHFFFAOYSA-N 0.000 description 1
- OBROYCQXICMORW-UHFFFAOYSA-N tripropoxyalumane Chemical compound [Al+3].CCC[O-].CCC[O-].CCC[O-] OBROYCQXICMORW-UHFFFAOYSA-N 0.000 description 1
- LTEHWCSSIHAVOQ-UHFFFAOYSA-N tripropyl borate Chemical compound CCCOB(OCCC)OCCC LTEHWCSSIHAVOQ-UHFFFAOYSA-N 0.000 description 1
- IYGPXXORQKFXCZ-UHFFFAOYSA-N tris(2-methoxyethyl) borate Chemical compound COCCOB(OCCOC)OCCOC IYGPXXORQKFXCZ-UHFFFAOYSA-N 0.000 description 1
- RQNVJDSEWRGEQR-UHFFFAOYSA-N tris(prop-2-enyl) borate Chemical compound C=CCOB(OCC=C)OCC=C RQNVJDSEWRGEQR-UHFFFAOYSA-N 0.000 description 1
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 description 1
- 229910052721 tungsten Inorganic materials 0.000 description 1
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- GPPXJZIENCGNKB-UHFFFAOYSA-N vanadium Chemical compound [V]#[V] GPPXJZIENCGNKB-UHFFFAOYSA-N 0.000 description 1
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- PAPBSGBWRJIAAV-UHFFFAOYSA-N ε-Caprolactone Chemical compound O=C1CCCCCO1 PAPBSGBWRJIAAV-UHFFFAOYSA-N 0.000 description 1
Classifications
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- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/26—Processing photosensitive materials; Apparatus therefor
- G03F7/40—Treatment after imagewise removal, e.g. baking
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/26—Processing photosensitive materials; Apparatus therefor
- G03F7/42—Stripping or agents therefor
- G03F7/422—Stripping or agents therefor using liquids only
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Description
Si(OR15)4 (D)
好適な縮合性ケイ素モノマーは、式(9)のモノマーであり、
Si(R50)q(X)4-q (9)
式中、各R50は、C1-30ヒドロカルビル部分及び置換C1-30ヒドロカルビル部分から独立して選択され、各Xは、ハロゲン、C1-10アルコキシ、-OH、-O-C(O)-R50、-(O-Si(R51)2)q2-X1及び(Si(R51)2)q3-X1から独立して選択され、X1は、ハロゲン、C1-10アルコキシ、-OH、-O-C(O)-R50から独立して選択され、各R51はR50及びXから独立して選択され、qは0~3の整数であり、q2は1~10の整数であり、q3は1~10の整数である。好ましくは、qは、0~2の整数、より好ましくは0~1、さらにより好ましくはq=0である。Xは、好ましくは、C1-10アルコキシ、-OH、-O-C(O)-R50、及び-(O-Si(R51)2)q2-X1から、より好ましくはC1-10アルコキシ及び-OHから選択される。X1は、好ましくは、C1-10アルコキシ及び-OHから選択される。R50の置換C1-30ヒドロカルビル部分は、ヒドロキシ、メルカプト、C1-20アルコキシ、アミノ、C1-20アルキルアミノ、ジ-C1-20アルキルアミノ、シアノ、ハロゲン、エポキシド、-C(=O)O-R51、-C(=O)-N(R51)2、及び-C(=O)-O-C(=O)-R51から選択される、1つ以上の置換基で置換される、その水素の1つ以上を有する、任意のC1-30ヒドロカルビル部分を指し、各R51は、H及びC1-20アルキルから選択される。これに限定するものではないが、好適なR50の置換C1-30ヒドロカルビル部分は、C1-30アルキル、C2-30アルケニル、C2-30アルキニル、C3-30シクロアルキル、及びC6-30アリールであり、好ましくはC1-20アルキル、C2-20アルケニル、C2-20アルキニル、C3-20シクロアルキル、及びC6-25アリールである。ケイ素モノマーは、しばしば、モノマーにおけるケイ素に結合される加水分解性部分の数によって言及される。例えば、「Mモノマー」は、式(R50)3SiXのモノマー等の1つの加水分解性部分を有するケイ素モノマーを指し、「Dモノマー」は、式(R50)2SiXのモノマー等の2つの加水分解性部分を有するケイ素モノマーを指し、「Tモノマー」は、式R50SiX3のモノマー等の3つの加水分解性部分を有するケイ素モノマーを指し、「Qモノマー」は、式SiX4のモノマー等の4つの加水分解性部分を有するケイ素モノマーを指し、式中、各モノマーにおけるX及びR50は、上記のとおりである。本縮合ポリマーを調製するために、M、D、T、及びQモノマーのうちのいずれも、個々に使用されてもよく、または前述のうちのいずれかの混合物が、使用されてもよい。好ましくは、縮合性ケイ素モノマーは、式(9a)、(9b)、(9c)、及び(9d)から選択される、1つ以上のモノマーであり、
(R50)3SiX (9a)
(R50)2SiX2 (9b)
R50SiX3 (9c)
SiX4 (9d)
式中、各X及びR50は、式(9)について上記のとおりである。1つ以上のQモノマー、つまり、式(9d)のモノマーが、本縮合ポリマーを調製するために使用されることが好ましい。そのような縮合性ケイ素モノマーは、一般的に市販されており、そのまま使用されてもよく、またはさらに精製されてもよい。
G(X2)m4 (10)
式中、Gは、炭素及びケイ素を除く、周期表の13~15族からの元素であり、各X2は、ハロゲン及びOR52から独立して選択され、各R52は、独立して、H、または1~30個の炭素原子を有する有機基であり、m4は、Gの原子価である。好ましくは、R52は、H、C1-10アルキル、-C(O)-C1-10アルキル、及びC6-10アリールから、より好ましくはH、C1-10アルキル、及び-C(O)-C1-10アルキルから選択される。Gは、好ましくは、ボロン、アルミニウム、ガリウム、イットリウム、ゲルマニウム、チタン、ジルコニウム、ハフニウム、ビスマス、スズ、リン、バナジウム、ヒ素、アンチモン、ニオブ、及びタンタルから、より好ましくはボロン、アルミニウム、及びゲルマニウムから選択される元素であり、さらにより好ましくは、Gは、ボロンである。式(10)の好適な化合物としては、ホウ酸トリメチル、ホウ酸トリエチル、ホウ酸トリプロピル、ホウ酸トリブチル、ホウ酸トリペンチル、ホウ酸トリヘキシル、ホウ酸トリシクロペンチル、ホウ酸トリシクロヘキシル、ホウ酸トリアリル、ホウ酸トリフェニル、ホウ素メトキシエトキシド、ホウ酸、酸化ホウ素;アルミニウムメトキシド、アルミニウムエトキシド、アルミニウムプロポキシド、アルミニウムブトキシド、アルミニウムアミルオキシド、アルミニウムヘキシルオキシド、アルミニウムシクロペントキシド、アルミニウムシクロヘキシルオキシド、アルミニウムアリルオキシド、アルミニウムフェノキシド、アルミニウムエトキシエトキシド、アルミニウムジプロポキシエチルアセトアセテート、アルミニウムジブトキシエチルアセトアセテート、アルミニウムプロポキシ-ビス-エチル-アセトアセテート、アルミニウムブトキシ-ビス-エチル-アセトアセテート、アルミニウム2,4-ペンタンジオネート、アルミニウム2,2,6,6-テトラメチル-3,5-ヘプタンジオネート、ゲルマニウムメトキシド、ゲルマニウムエトキシド、ゲルマニウムプロポキシド、ゲルマニウムブトキシド、ゲルマニウムアミルオキシド、ゲルマニウムヘキシルオキシド、ゲルマニウムシクロペントキシド、ゲルマニウムシクロヘキシルオキシド、ゲルマニウムアリルオキシド、ゲルマニウムフェノキシド、ゲルマニウムエトキシエトキシドが挙げられるが、それらに限定されない。好適なエッチング選択性改良剤は、米国特許第8,951,917号に開示されており、Gelest,Inc.(Tullytown,Pennsylvania)より入手可能であり得る。
EE、PGMEA、EL、HBM、及びそれらの組み合わせである。
%の量で使用される。
D-26)のパドルを各ウェーハに60秒間塗布した後、ウェーハを脱イオン水ですすぎ、スピン乾燥し、膜厚を再測定した。105℃/60秒の最終乾燥ベークウェーハに適用し、最終膜厚を測定した。このTMAH剥離に起因するフィルム除去速度(Å/分)として報告された各膜の厚さ損失を表2に報告する。マイナスの膜剥離値は、膜厚の増加を示す。
Claims (15)
- (a)1つ以上の溶媒と、(b)(i)1つ以上の有機ポリマーであって、重合単位として、酸性プロトンと水中で-5~13のpKaとを有する部分を有する1つ以上の第1の不飽和モノマー、縮合性ケイ素含有部分を有し、前記縮合性ケイ素含有部分が、前記有機ポリマー骨格にペンダント結合する1つ以上の第2の不飽和モノマー及び酸性部分であって、酸性プロトンを有しかつ水中で-5~13のpKaを有する酸性部分を含まず、縮合性ケイ素含有部分を含まず、かつ式(5):
を有する1つ以上の第3の不飽和モノマーを含む、1つ以上の有機ポリマー、ならびに(ii)1つ以上の縮合性ケイ素モノマーからなる縮合物及び/または加水分解物と、を含む、組成物。 - 少なくとも1つの第1の不飽和モノマーが、カルボン酸、スルホン酸、スルフィン酸、スルファミン酸、ボロン酸、リン酸、ならびにこれらの組み合わせ及び酸塩、ヒドロキシアリール基、非置換イミド基、メルカプト基、ならびにC1-20ヒドロキシル置換ハロアルキル基からなる群から選択される酸性部分を有する、請求項1に記載の組成物。
- 少なくとも1つの第1の不飽和モノマーが、式(1)を有し、
- L1が、単共有結合、または1~20個の炭素原子及び任意に1個以上のヘテロ原子を有する2価の有機ラジカルである、請求項3に記載の組成物。
- 少なくとも1つの第2の不飽和モノマーが、式(3)を有し、
- L2が、1~20個の炭素原子及び任意に1個以上のヘテロ原子を有する2価の有機ラジカルである、請求項6に記載の組成物。
- 前記2価の連結基が、式-C(=O)-O-L3-を有し、式中、L3は、単結合、または1~20個の炭素原子を有する有機ラジカルである、請求項6に記載の組成物。
- 前記有機ポリマーが、重合単位として、発色団部分を有する1つ以上の不飽和モノマーをさらに含む、請求項1~8のいずれか1項に記載の組成物。
- 前記発色団部分が、前記有機ポリマー骨格からペンダント結合している、請求項9に記載の組成物。
- 前記発色団部分が、フリル、ピリル(pyryl)、チオフェニル、ピリジル、フェニル、ナフチル、アセナフチル、フルオレニル、カルバゾリル、アントラセニル、フェナントリル、ピレニル、コロネニル、テトラセニル、ペンタセニル、テトラフェニル、ベンゾテトラセニル、トリフェニレニル、ペリレニル、ベンジル、フェネチル、トリル、キシリル、スチレニル、ビニルナフチル、ビニルアントラセニル、ジベンゾチオフェニル、チオキサントニル、インドリル、及びアクリジニルからなる群から選択される、請求項10に記載の組成物。
- 少なくとも1つの縮合性ケイ素モノマーが、式(9)を有し、
Si(R50)p(X)4-p (9)
各R50は、C1-30ヒドロカルビル部分及び置換C1-30ヒドロカルビル部分から独立して選択され、各Xは、ハロゲン、C1-10アルコキシ、-OH、-O-C(O)-R50、-(O-Si(R51)2)p2-X1、及び-(Si(R51)2)p3-X1から独立して選択され、X1は、ハロゲン、C1-10アルコキシ、-OH、-O-C(O)-R50から独立して選択され、各R51は、R50及びXから独立して選択され、pは、0~3の整数であり、p2は、1~10の整数であり、p3は、1~10の整数である、請求項1~11のいずれか1項に記載の組成物。 - p=0または1である、請求項12に記載の組成物。
- (a)請求項1~13のいずれか1項に記載の組成物で基板をコーティングして、コーティング層を形成することと、(b)前記コーティング層を硬化させてポリマー下層を形成することと、(c)前記ポリマー下層にフォトレジストの層を配設することと、(d)前記フォトレジスト層をパターン状に露光して、潜像を形成することと、(e)前記潜像を現像して、中にレリーフ画像を有するパターン形成されたフォトレジスト層を形成することと、(f)前記レリーフ画像を前記基板に転写することと、(g)湿潤剥離によって前記ポリマー下層を除去することと、を含む、方法。
- 前記ポリマー下層が、室温で、湿潤剥離によって除去される、請求項14に記載の方法。
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