JP5271274B2 - レジスト下層膜加工用ハードマスク組成物、前記ハードマスク組成物を用いた半導体集積回路デバイスの製造方法、および前記方法によって製造された半導体集積回路デバイス - Google Patents
レジスト下層膜加工用ハードマスク組成物、前記ハードマスク組成物を用いた半導体集積回路デバイスの製造方法、および前記方法によって製造された半導体集積回路デバイス Download PDFInfo
- Publication number
- JP5271274B2 JP5271274B2 JP2009537092A JP2009537092A JP5271274B2 JP 5271274 B2 JP5271274 B2 JP 5271274B2 JP 2009537092 A JP2009537092 A JP 2009537092A JP 2009537092 A JP2009537092 A JP 2009537092A JP 5271274 B2 JP5271274 B2 JP 5271274B2
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- hard mask
- group
- mask composition
- tetrabutylammonium
- weight
- Prior art date
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- 239000000203 mixture Substances 0.000 title claims description 74
- 238000012545 processing Methods 0.000 title claims description 16
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- 239000004065 semiconductor Substances 0.000 title description 8
- 238000004519 manufacturing process Methods 0.000 title description 5
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- 150000001875 compounds Chemical class 0.000 claims description 51
- 125000003118 aryl group Chemical group 0.000 claims description 31
- 150000001282 organosilanes Chemical class 0.000 claims description 21
- 125000002947 alkylene group Chemical group 0.000 claims description 18
- 239000002904 solvent Substances 0.000 claims description 16
- 239000003377 acid catalyst Substances 0.000 claims description 14
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 12
- 125000000524 functional group Chemical group 0.000 claims description 10
- ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical group OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 claims description 9
- 125000005647 linker group Chemical group 0.000 claims description 9
- 239000000178 monomer Substances 0.000 claims description 9
- 238000006068 polycondensation reaction Methods 0.000 claims description 9
- ZDYVRSLAEXCVBX-UHFFFAOYSA-N pyridinium p-toluenesulfonate Chemical compound C1=CC=[NH+]C=C1.CC1=CC=C(S([O-])(=O)=O)C=C1 ZDYVRSLAEXCVBX-UHFFFAOYSA-N 0.000 claims description 9
- XSQUKJJJFZCRTK-UHFFFAOYSA-N urea group Chemical group NC(=O)N XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 9
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 claims description 8
- SHFJWMWCIHQNCP-UHFFFAOYSA-M hydron;tetrabutylazanium;sulfate Chemical compound OS([O-])(=O)=O.CCCC[N+](CCCC)(CCCC)CCCC SHFJWMWCIHQNCP-UHFFFAOYSA-M 0.000 claims description 8
- 229910017604 nitric acid Inorganic materials 0.000 claims description 8
- FPGGTKZVZWFYPV-UHFFFAOYSA-M tetrabutylammonium fluoride Chemical compound [F-].CCCC[N+](CCCC)(CCCC)CCCC FPGGTKZVZWFYPV-UHFFFAOYSA-M 0.000 claims description 8
- 125000004400 (C1-C12) alkyl group Chemical group 0.000 claims description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 6
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 6
- 125000000623 heterocyclic group Chemical group 0.000 claims 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 claims description 6
- 239000004215 Carbon black (E152) Substances 0.000 claims description 5
- 239000007810 chemical reaction solvent Substances 0.000 claims description 5
- 229930195733 hydrocarbon Natural products 0.000 claims description 5
- LLNAMUJRIZIXHF-CLFYSBASSA-N (z)-2-methyl-3-phenylprop-2-en-1-ol Chemical compound OCC(/C)=C\C1=CC=CC=C1 LLNAMUJRIZIXHF-CLFYSBASSA-N 0.000 claims description 4
- KUCWUAFNGCMZDB-UHFFFAOYSA-N 2-amino-3-nitrophenol Chemical compound NC1=C(O)C=CC=C1[N+]([O-])=O KUCWUAFNGCMZDB-UHFFFAOYSA-N 0.000 claims description 4
- CLCSYZQBLQDRQU-UHFFFAOYSA-N 3-[3-(hexadecanoylamino)propyl-dimethylazaniumyl]propane-1-sulfonate Chemical compound CCCCCCCCCCCCCCCC(=O)NCCC[N+](C)(C)CCCS([O-])(=O)=O CLCSYZQBLQDRQU-UHFFFAOYSA-N 0.000 claims description 4
- REAVCZWUMGIGSW-UHFFFAOYSA-M 4-methylbenzenesulfonate;tetrabutylazanium Chemical compound CC1=CC=C(S([O-])(=O)=O)C=C1.CCCC[N+](CCCC)(CCCC)CCCC REAVCZWUMGIGSW-UHFFFAOYSA-M 0.000 claims description 4
- 239000000654 additive Substances 0.000 claims description 4
- 230000000996 additive effect Effects 0.000 claims description 4
- VZTDIZULWFCMLS-UHFFFAOYSA-N ammonium formate Chemical compound [NH4+].[O-]C=O VZTDIZULWFCMLS-UHFFFAOYSA-N 0.000 claims description 4
- JTMZBRWRXFAITF-UHFFFAOYSA-N azane;(7,7-dimethyl-3-oxo-4-bicyclo[2.2.1]heptanyl)methanesulfonic acid Chemical compound [NH4+].C1CC2(CS([O-])(=O)=O)C(=O)CC1C2(C)C JTMZBRWRXFAITF-UHFFFAOYSA-N 0.000 claims description 4
- 239000003431 cross linking reagent Substances 0.000 claims description 4
- FDTUVFSBEYKVAP-UHFFFAOYSA-N formic acid;pyridine Chemical compound OC=O.C1=CC=NC=C1 FDTUVFSBEYKVAP-UHFFFAOYSA-N 0.000 claims description 4
- ARRNBPCNZJXHRJ-UHFFFAOYSA-M hydron;tetrabutylazanium;phosphate Chemical compound OP(O)([O-])=O.CCCC[N+](CCCC)(CCCC)CCCC ARRNBPCNZJXHRJ-UHFFFAOYSA-M 0.000 claims description 4
- 239000003381 stabilizer Substances 0.000 claims description 4
- 239000004094 surface-active agent Substances 0.000 claims description 4
- JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 claims description 4
- MCZDHTKJGDCTAE-UHFFFAOYSA-M tetrabutylazanium;acetate Chemical compound CC([O-])=O.CCCC[N+](CCCC)(CCCC)CCCC MCZDHTKJGDCTAE-UHFFFAOYSA-M 0.000 claims description 4
- GMRIOAVKKGNMMV-UHFFFAOYSA-N tetrabutylazanium;azide Chemical compound [N-]=[N+]=[N-].CCCC[N+](CCCC)(CCCC)CCCC GMRIOAVKKGNMMV-UHFFFAOYSA-N 0.000 claims description 4
- WGYONVRJGWHMKV-UHFFFAOYSA-M tetrabutylazanium;benzoate Chemical compound [O-]C(=O)C1=CC=CC=C1.CCCC[N+](CCCC)(CCCC)CCCC WGYONVRJGWHMKV-UHFFFAOYSA-M 0.000 claims description 4
- KRRBFUJMQBDDPR-UHFFFAOYSA-N tetrabutylazanium;cyanide Chemical compound N#[C-].CCCC[N+](CCCC)(CCCC)CCCC KRRBFUJMQBDDPR-UHFFFAOYSA-N 0.000 claims description 4
- SNMZANHSFVMKKA-UHFFFAOYSA-M tetrabutylazanium;formate Chemical compound [O-]C=O.CCCC[N+](CCCC)(CCCC)CCCC SNMZANHSFVMKKA-UHFFFAOYSA-M 0.000 claims description 4
- DPKBAXPHAYBPRL-UHFFFAOYSA-M tetrabutylazanium;iodide Chemical compound [I-].CCCC[N+](CCCC)(CCCC)CCCC DPKBAXPHAYBPRL-UHFFFAOYSA-M 0.000 claims description 4
- ZXUCBXRTRRIBSO-UHFFFAOYSA-L tetrabutylazanium;sulfate Chemical compound [O-]S([O-])(=O)=O.CCCC[N+](CCCC)(CCCC)CCCC.CCCC[N+](CCCC)(CCCC)CCCC ZXUCBXRTRRIBSO-UHFFFAOYSA-L 0.000 claims description 4
- WWIYWFVQZQOECA-UHFFFAOYSA-M tetramethylazanium;formate Chemical compound [O-]C=O.C[N+](C)(C)C WWIYWFVQZQOECA-UHFFFAOYSA-M 0.000 claims description 4
- PTMFUWGXPRYYMC-UHFFFAOYSA-N triethylazanium;formate Chemical compound OC=O.CCN(CC)CC PTMFUWGXPRYYMC-UHFFFAOYSA-N 0.000 claims description 4
- UPVCRZBVVOXMDA-UHFFFAOYSA-N trimethylazanium;formate Chemical compound OC=O.CN(C)C UPVCRZBVVOXMDA-UHFFFAOYSA-N 0.000 claims description 4
- DENRZWYUOJLTMF-UHFFFAOYSA-N diethyl sulfate Chemical compound CCOS(=O)(=O)OCC DENRZWYUOJLTMF-UHFFFAOYSA-N 0.000 claims description 3
- 238000002156 mixing Methods 0.000 claims description 3
- 239000002253 acid Substances 0.000 claims description 2
- 125000001183 hydrocarbyl group Chemical group 0.000 claims 2
- NHGXDBSUJJNIRV-UHFFFAOYSA-M tetrabutylammonium chloride Chemical compound [Cl-].CCCC[N+](CCCC)(CCCC)CCCC NHGXDBSUJJNIRV-UHFFFAOYSA-M 0.000 claims 2
- WYSXJFIFFXPGAP-UHFFFAOYSA-N nitrous acid hydrobromide Chemical compound N(=O)O.Br WYSXJFIFFXPGAP-UHFFFAOYSA-N 0.000 claims 1
- 239000010408 film Substances 0.000 description 54
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- 239000000463 material Substances 0.000 description 21
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- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
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- 238000003860 storage Methods 0.000 description 14
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- 239000006117 anti-reflective coating Substances 0.000 description 11
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 10
- 230000000052 comparative effect Effects 0.000 description 10
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 9
- 229910052710 silicon Inorganic materials 0.000 description 9
- 239000010703 silicon Substances 0.000 description 9
- 230000003667 anti-reflective effect Effects 0.000 description 8
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- PZPGRFITIJYNEJ-UHFFFAOYSA-N disilane Chemical compound [SiH3][SiH3] PZPGRFITIJYNEJ-UHFFFAOYSA-N 0.000 description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical group CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-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
- LZCLXQDLBQLTDK-UHFFFAOYSA-N ethyl 2-hydroxypropanoate Chemical compound CCOC(=O)C(C)O LZCLXQDLBQLTDK-UHFFFAOYSA-N 0.000 description 6
- 239000007789 gas Substances 0.000 description 6
- BFXIKLCIZHOAAZ-UHFFFAOYSA-N methyltrimethoxysilane Chemical compound CO[Si](C)(OC)OC BFXIKLCIZHOAAZ-UHFFFAOYSA-N 0.000 description 5
- 229910052757 nitrogen Inorganic materials 0.000 description 5
- 239000011541 reaction mixture Substances 0.000 description 5
- 238000012546 transfer Methods 0.000 description 5
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- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
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- 238000000059 patterning Methods 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- KPZGRMZPZLOPBS-UHFFFAOYSA-N 1,3-dichloro-2,2-bis(chloromethyl)propane Chemical compound ClCC(CCl)(CCl)CCl KPZGRMZPZLOPBS-UHFFFAOYSA-N 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
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- 238000000576 coating method Methods 0.000 description 3
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- 229940116333 ethyl lactate Drugs 0.000 description 3
- 238000005755 formation reaction Methods 0.000 description 3
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- 239000001257 hydrogen Substances 0.000 description 3
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- -1 silane compound Chemical class 0.000 description 3
- 150000004756 silanes Chemical class 0.000 description 3
- SHRKDVQQQPFSIY-UHFFFAOYSA-M tetrabutylazanium;nitrite Chemical compound [O-]N=O.CCCC[N+](CCCC)(CCCC)CCCC SHRKDVQQQPFSIY-UHFFFAOYSA-M 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
- DJYGUVIGOGFJOF-UHFFFAOYSA-N trimethoxy(trimethoxysilylmethyl)silane Chemical compound CO[Si](OC)(OC)C[Si](OC)(OC)OC DJYGUVIGOGFJOF-UHFFFAOYSA-N 0.000 description 3
- JOLQKTGDSGKSKJ-UHFFFAOYSA-N 1-ethoxypropan-2-ol Chemical compound CCOCC(C)O JOLQKTGDSGKSKJ-UHFFFAOYSA-N 0.000 description 2
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- 229910008051 Si-OH Inorganic materials 0.000 description 2
- 229910006358 Si—OH Inorganic materials 0.000 description 2
- 230000002411 adverse Effects 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 238000009833 condensation Methods 0.000 description 2
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- 238000006482 condensation reaction Methods 0.000 description 2
- 238000010586 diagram Methods 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
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- WGTYBPLFGIVFAS-UHFFFAOYSA-M tetramethylammonium hydroxide Chemical compound [OH-].C[N+](C)(C)C WGTYBPLFGIVFAS-UHFFFAOYSA-M 0.000 description 2
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 241000233805 Phoenix Species 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- TUVYSBJZBYRDHP-UHFFFAOYSA-N acetic acid;methoxymethane Chemical compound COC.CC(O)=O TUVYSBJZBYRDHP-UHFFFAOYSA-N 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
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- 229910052804 chromium Inorganic materials 0.000 description 1
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- 238000001312 dry etching Methods 0.000 description 1
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- 230000000694 effects Effects 0.000 description 1
- 238000000445 field-emission scanning electron microscopy Methods 0.000 description 1
- 230000001771 impaired effect Effects 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 150000004767 nitrides Chemical class 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 229920002120 photoresistant polymer Polymers 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
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- 229920005591 polysilicon Polymers 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000002310 reflectometry Methods 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
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- 150000003839 salts Chemical class 0.000 description 1
- 229910052814 silicon oxide Inorganic materials 0.000 description 1
- FOQJQXVUMYLJSU-UHFFFAOYSA-N triethoxy(1-triethoxysilylethyl)silane Chemical compound CCO[Si](OCC)(OCC)C(C)[Si](OCC)(OCC)OCC FOQJQXVUMYLJSU-UHFFFAOYSA-N 0.000 description 1
- YUYCVXFAYWRXLS-UHFFFAOYSA-N trimethoxysilane Chemical compound CO[SiH](OC)OC YUYCVXFAYWRXLS-UHFFFAOYSA-N 0.000 description 1
Images
Classifications
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
- C08G77/48—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule in which at least two but not all the silicon atoms are connected by linkages other than oxygen atoms
- C08G77/50—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule in which at least two but not all the silicon atoms are connected by linkages other than oxygen atoms by carbon linkages
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
- G03F7/09—Photosensitive materials characterised by structural details, e.g. supports, auxiliary layers
- G03F7/091—Photosensitive materials characterised by structural details, e.g. supports, auxiliary layers characterised by antireflection means or light filtering or absorbing means, e.g. anti-halation, contrast enhancement
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L83/00—Compositions of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon only; Compositions of derivatives of such polymers
- C08L83/14—Compositions of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon only; Compositions of derivatives of such polymers in which at least two but not all the silicon atoms are connected by linkages other than oxygen atoms
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- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
- G03F7/075—Silicon-containing compounds
- G03F7/0757—Macromolecular compounds containing Si-O, Si-C or Si-N bonds
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
- G03F7/09—Photosensitive materials characterised by structural details, e.g. supports, auxiliary layers
- G03F7/11—Photosensitive materials characterised by structural details, e.g. supports, auxiliary layers having cover layers or intermediate layers, e.g. subbing layers
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
- H01L21/00—Processes or apparatus adapted for the manufacture or treatment of semiconductor or solid state devices or of parts thereof
- H01L21/02—Manufacture or treatment of semiconductor devices or of parts thereof
- H01L21/02104—Forming layers
- H01L21/02107—Forming insulating materials on a substrate
- H01L21/02109—Forming insulating materials on a substrate characterised by the type of layer, e.g. type of material, porous/non-porous, pre-cursors, mixtures or laminates
- H01L21/02112—Forming insulating materials on a substrate characterised by the type of layer, e.g. type of material, porous/non-porous, pre-cursors, mixtures or laminates characterised by the material of the layer
- H01L21/02123—Forming insulating materials on a substrate characterised by the type of layer, e.g. type of material, porous/non-porous, pre-cursors, mixtures or laminates characterised by the material of the layer the material containing silicon
- H01L21/02126—Forming insulating materials on a substrate characterised by the type of layer, e.g. type of material, porous/non-porous, pre-cursors, mixtures or laminates characterised by the material of the layer the material containing silicon the material containing Si, O, and at least one of H, N, C, F, or other non-metal elements, e.g. SiOC, SiOC:H or SiONC
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- H01L21/02208—Forming insulating materials on a substrate characterised by the type of layer, e.g. type of material, porous/non-porous, pre-cursors, mixtures or laminates the layer being characterised by the precursor material for deposition the precursor containing a compound comprising Si
- H01L21/02214—Forming insulating materials on a substrate characterised by the type of layer, e.g. type of material, porous/non-porous, pre-cursors, mixtures or laminates the layer being characterised by the precursor material for deposition the precursor containing a compound comprising Si the compound comprising silicon and oxygen
- H01L21/02216—Forming insulating materials on a substrate characterised by the type of layer, e.g. type of material, porous/non-porous, pre-cursors, mixtures or laminates the layer being characterised by the precursor material for deposition the precursor containing a compound comprising Si the compound comprising silicon and oxygen the compound being a molecule comprising at least one silicon-oxygen bond and the compound having hydrogen or an organic group attached to the silicon or oxygen, e.g. a siloxane
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- H01L21/00—Processes or apparatus adapted for the manufacture or treatment of semiconductor or solid state devices or of parts thereof
- H01L21/02—Manufacture or treatment of semiconductor devices or of parts thereof
- H01L21/027—Making masks on semiconductor bodies for further photolithographic processing not provided for in group H01L21/18 or H01L21/34
- H01L21/0271—Making masks on semiconductor bodies for further photolithographic processing not provided for in group H01L21/18 or H01L21/34 comprising organic layers
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- H01L21/04—Manufacture or treatment of semiconductor devices or of parts thereof the devices having potential barriers, e.g. a PN junction, depletion layer or carrier concentration layer
- H01L21/18—Manufacture or treatment of semiconductor devices or of parts thereof the devices having potential barriers, e.g. a PN junction, depletion layer or carrier concentration layer the devices having semiconductor bodies comprising elements of Group IV of the Periodic Table or AIIIBV compounds with or without impurities, e.g. doping materials
- H01L21/30—Treatment of semiconductor bodies using processes or apparatus not provided for in groups H01L21/20 - H01L21/26
- H01L21/31—Treatment of semiconductor bodies using processes or apparatus not provided for in groups H01L21/20 - H01L21/26 to form insulating layers thereon, e.g. for masking or by using photolithographic techniques; After treatment of these layers; Selection of materials for these layers
- H01L21/3105—After-treatment
- H01L21/311—Etching the insulating layers by chemical or physical means
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- H01L21/18—Manufacture or treatment of semiconductor devices or of parts thereof the devices having potential barriers, e.g. a PN junction, depletion layer or carrier concentration layer the devices having semiconductor bodies comprising elements of Group IV of the Periodic Table or AIIIBV compounds with or without impurities, e.g. doping materials
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- H01L21/312—Organic layers, e.g. photoresist
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- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
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Description
[比較例1]
メチルトリメトキシシラン1,750g、フェニルトリメトキシシラン340g、およびトリメトキシシラン313gを、機械的撹拌機、コンデンサ、滴下漏斗、および窒素導入管を備えた10リットルの4つ口フラスコに入れたプロピレングリコールモノメチルエーテルアセテート(PGMEA)5,600gに溶解させ、次いで、これに硝酸水溶液(1,000ppm)925gを添加した。得られた混合物を60℃で1時間反応させた後、生成したメタノールを減圧下で除去した。反応温度を50℃に維持して、反応を1週間継続させた。反応完了後、反応混合物にヘキサンを添加して式8の重合体を沈殿させた:
メチルトリメトキシシラン1,375g、フェニルトリメトキシシラン286g、およびビス(トリメトキシシリル)メタン740gを、機械的撹拌機、コンデンサ、滴下漏斗、および窒素導入管を備えた10リットルの4つ口フラスコに入れたPGMEA5,600gに溶解させ、次いで、これに硝酸水溶液(1,000ppm)654gを添加した。得られた混合物を50℃で1時間反応させた後、生成したメタノールを減圧下で除去した。反応温度を80℃に維持して、反応を1週間継続させた。反応完了後、反応混合物にヘキサンを添加して式9の重合体を沈殿させた:
メチルトリメトキシシラン1,632gおよびビス(トリメトキシシリル)メタン768gを、機械的撹拌機、コンデンサ、滴下漏斗、および窒素導入管を備えた10リットルの4つ口フラスコに入れたPGMEA5,600gに溶解させ、次いで、これに硝酸水溶液(1,000ppm)654gを添加した。得られた混合物を50℃で1時間反応させた後、生成したメタノールを減圧下で除去した。反応温度を50℃に維持して、反応を1週間継続させた。反応完了後、反応混合物にヘキサンを添加して式10の重合体を沈殿させた:
メチルトリメトキシシラン686gおよびビス(トリメトキシシリル)メタン1,714gを、機械的撹拌機、コンデンサ、滴下漏斗、および窒素導入管を備えた10リットルの4つ口フラスコに入れたPGMEA5,600gに溶解させ、次いで、これに硝酸水溶液(1,000ppm)462gを添加した。得られた混合物を50℃で1時間反応させた後、生成したメタノールを減圧下で除去した。反応温度を50℃に維持して、反応を3日間継続させた。反応完了後、反応混合物にヘキサンを添加して式11の重合体を沈殿させた:
フェニルトリメトキシシラン189g、メチルトリメトキシシラン519g、およびビス(トリエトキシシリル)エタン1,691gを、機械的撹拌機、コンデンサ、滴下漏斗、および窒素導入管を備えた10リットルの4つ口フラスコに入れたPGMEA5,600gに溶解させ、次いで、これに硝酸水溶液(1,000ppm)541gを添加した。得られた混合物を50℃で1時間反応させた後、生成したメタノールおよびエタノールを減圧下で除去した。反応温度を50℃に維持して、反応を3日間継続させた。反応完了後、反応混合物にヘキサンを添加して式12の重合体を沈殿させた:
比較例1および実施例1、4、参考例2、3で調製した溶液の保存安定性を試験した。各溶液の3つの試料を40℃で保存した。10日間隔で、試料中の重合体の分子量および試料をコートした後に得られた膜の厚さを測定した。結果を表1に示す。
比較例1および実施例1、4、参考例2、3で形成された膜の屈折率(n)および吸光係数(k)をエリプソメータ(J.A.Woollam)を用いて測定した。結果を表2に示す。
比較例1および実施例1、4、参考例2、3で形成された膜の水との接触角を、接触角測定システム(Phoenix 300 plus,SEO)を用いて測定した。各膜の表面(5点)上に10μlの水を滴下した。膜表面と水滴との間の角度を測定した。結果を表3に示す。
比較例1および実施例1、4、参考例2、3の膜について、パターンを用いないバルクドライエッチングを以下のプラズマ条件下で100秒間行った:90mT,400W/250W,24N2,12O2,500Ar。エッチング後、膜の厚さを測定し、単位時間あたりのエッチング速度を計算した。N2およびArをフローイングガスとして用い、O2を主エッチングガスとして用いた。結果を表4に示す。
比較例1および実施例1、4、参考例2、3で形成された各膜上に、ArFフォトレジストをコートし、110℃で60秒間ベーキングし、ArF露光システム(ASML1250,NA0.82)を用いて露光し、TMAH水溶液(2.38重量%)で現像して80nmのラインアンドスペースパターンを形成した。参考例2および3で形成した膜上に、さらなる反射防止コーティングを形成した。CD−SEMを用いてパターンを観察した。パターンの露光寛容度(EL)マージンを露光エネルギーの関数として、焦点深度(DoF)マージンを光源からの距離の関数として測定した。結果を表5に示す。
実験例5で得られたパターニングされた試片をCFxプラズマ、O2プラズマおよびCFxプラズマを用いて順にドライエッチングした。残留する有機材料をO2を用いて完全に除去し、エッチングした試片の断面をFE−SEMで観察した。結果を表6に示す。
Claims (7)
- オルガノシラン重合体および溶媒または溶媒の混合物を含むレジスト下層膜加工用ハードマスク組成物であって、前記オルガノシラン重合体は、酸触媒の存在下で、式1、2、および3で表される化合物を含む単量体成分から調製され、
p−トルエンスルホン酸ピリジニウム、アミドスルホベタイン−16、(−)−カンファー−10−スルホン酸アンモニウム塩、ギ酸アンモニウム、ギ酸トリエチルアンモニウム、ギ酸トリメチルアンモニウム、ギ酸テトラメチルアンモニウム、ギ酸ピリジニウム、ギ酸テトラブチルアンモニウム、硝酸テトラメチルアンモニウム、硝酸テトラブチルアンモニウム、酢酸テトラブチルアンモニウム、アジ化テトラブチルアンモニウム、安息香酸テトラブチルアンモニウム、重硫酸テトラブチルアンモニウム、臭化テトラブチルアンモニウム、塩化テトラブチルアンモニウム、シアン化テトラブチルアンモニウム、フッ化テトラブチルアンモニウム、ヨウ化テトラブチルアンモニウム、硫酸テトラブチルアンモニウム、亜硝酸テトラブチルアンモニウム、p−トルエンスルホン酸テトラブチルアンモニウム、およびリン酸テトラブチルアンモニウムからなる群から選択される少なくとも1つの化合物をさらに含む、レジスト下層膜加工用ハードマスク組成物:
- 前記重縮合生成物は、式7で表される化合物である、請求項2に記載のハードマスク組成物:
- 前記オルガノシラン重合体は、式1、2、および3の化合物100重量部に対して、式1の化合物0を超えて90重量部以下、式2の化合物5〜90重量部、および式3の化合物5〜90重量部を混合し、混合物を0.001〜5重量部の酸触媒存在下で100〜900重量部の反応溶媒中で反応させることによって調製される、請求項1〜3のいずれか1項に記載のハードマスク組成物。
- 前記酸触媒は、硝酸、硫酸、塩酸、p−トルエンスルホン酸一水和物、ジエチル硫酸、およびこれらの混合物からなる群から選択される、請求項1〜4のいずれか1項に記載のハードマスク組成物。
- 前記オルガノシラン重合体は、前記ハードマスク組成物100重量部に対して、1〜50重量部の量で存在する、請求項1〜5のいずれか1項に記載のハードマスク組成物。
- 架橋剤、ラジカル安定剤、および界面活性剤から選択される少なくとも1つの添加剤をさらに含む、請求項1〜6のいずれか1項に記載のハードマスク組成物。
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KR10-2006-0115411 | 2006-11-21 | ||
PCT/KR2007/005894 WO2008063016A1 (en) | 2006-11-21 | 2007-11-21 | Hardmask composition for processing resist underlayer film, process for producing semiconductor integrated circuit device using the hardmask composition, and semiconductor integrated circuit device produced by the process |
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KR100930672B1 (ko) * | 2008-01-11 | 2009-12-09 | 제일모직주식회사 | 실리콘계 하드마스크 조성물 및 이를 이용한 반도체집적회로 디바이스의 제조방법 |
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KR101288572B1 (ko) * | 2008-12-17 | 2013-07-22 | 제일모직주식회사 | 보관안정성이 우수한 레지스트 하층막용 하드마스크 조성물 |
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