JP2015063523A - ハードマスク - Google Patents
ハードマスク Download PDFInfo
- Publication number
- JP2015063523A JP2015063523A JP2014179115A JP2014179115A JP2015063523A JP 2015063523 A JP2015063523 A JP 2015063523A JP 2014179115 A JP2014179115 A JP 2014179115A JP 2014179115 A JP2014179115 A JP 2014179115A JP 2015063523 A JP2015063523 A JP 2015063523A
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- Prior art keywords
- composition
- layer
- chromophore
- metal
- group
- 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.)
- Granted
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- 239000000203 mixture Substances 0.000 claims abstract description 49
- 239000000758 substrate Substances 0.000 claims abstract description 34
- 229920000642 polymer Polymers 0.000 claims abstract description 32
- 150000002902 organometallic compounds Chemical class 0.000 claims abstract description 31
- 229910052751 metal Inorganic materials 0.000 claims abstract description 30
- 239000002184 metal Substances 0.000 claims abstract description 30
- 239000003446 ligand Substances 0.000 claims abstract description 15
- 239000003960 organic solvent Substances 0.000 claims abstract description 10
- 125000005647 linker group Chemical group 0.000 claims abstract description 7
- 125000006659 (C1-C20) hydrocarbyl group Chemical group 0.000 claims abstract description 4
- 238000000034 method Methods 0.000 claims description 26
- 229920002120 photoresistant polymer Polymers 0.000 claims description 19
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 6
- 125000003118 aryl group Chemical group 0.000 claims description 6
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 6
- 238000000576 coating method Methods 0.000 claims description 6
- 238000004381 surface treatment Methods 0.000 claims description 6
- 239000010936 titanium Substances 0.000 claims description 6
- 229910052782 aluminium Inorganic materials 0.000 claims description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims description 5
- 239000011248 coating agent Substances 0.000 claims description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 5
- 229910052719 titanium Inorganic materials 0.000 claims description 5
- 229910052721 tungsten Inorganic materials 0.000 claims description 5
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 claims description 4
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims description 4
- 229910052735 hafnium Inorganic materials 0.000 claims description 4
- 229910052750 molybdenum Inorganic materials 0.000 claims description 4
- 229910052760 oxygen Inorganic materials 0.000 claims description 4
- 229910052715 tantalum Inorganic materials 0.000 claims description 4
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 claims description 4
- 239000010937 tungsten Substances 0.000 claims description 4
- 229910052726 zirconium Inorganic materials 0.000 claims description 4
- GYHNNYVSQQEPJS-UHFFFAOYSA-N Gallium Chemical compound [Ga] GYHNNYVSQQEPJS-UHFFFAOYSA-N 0.000 claims description 3
- ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 claims description 3
- QCWXUUIWCKQGHC-UHFFFAOYSA-N Zirconium Chemical compound [Zr] QCWXUUIWCKQGHC-UHFFFAOYSA-N 0.000 claims description 3
- 125000003545 alkoxy group Chemical group 0.000 claims description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 3
- 229910052733 gallium Inorganic materials 0.000 claims description 3
- 229910052732 germanium Inorganic materials 0.000 claims description 3
- GNPVGFCGXDBREM-UHFFFAOYSA-N germanium atom Chemical compound [Ge] GNPVGFCGXDBREM-UHFFFAOYSA-N 0.000 claims description 3
- VBJZVLUMGGDVMO-UHFFFAOYSA-N hafnium atom Chemical compound [Hf] VBJZVLUMGGDVMO-UHFFFAOYSA-N 0.000 claims description 3
- 229910052738 indium Inorganic materials 0.000 claims description 3
- APFVFJFRJDLVQX-UHFFFAOYSA-N indium atom Chemical compound [In] APFVFJFRJDLVQX-UHFFFAOYSA-N 0.000 claims description 3
- 239000011733 molybdenum Substances 0.000 claims description 3
- 229910052757 nitrogen Inorganic materials 0.000 claims description 3
- 239000001301 oxygen Substances 0.000 claims description 3
- 230000005855 radiation Effects 0.000 claims description 3
- 229910052717 sulfur Inorganic materials 0.000 claims description 3
- GUVRBAGPIYLISA-UHFFFAOYSA-N tantalum atom Chemical compound [Ta] GUVRBAGPIYLISA-UHFFFAOYSA-N 0.000 claims description 3
- 229910052716 thallium Inorganic materials 0.000 claims description 3
- BKVIYDNLLOSFOA-UHFFFAOYSA-N thallium Chemical compound [Tl] BKVIYDNLLOSFOA-UHFFFAOYSA-N 0.000 claims description 3
- 229910052720 vanadium Inorganic materials 0.000 claims description 3
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 2
- 125000002178 anthracenyl group Chemical group C1(=CC=CC2=CC3=CC=CC=C3C=C12)* 0.000 claims description 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 125000001624 naphthyl group Chemical group 0.000 claims description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
- 125000005561 phenanthryl group Chemical group 0.000 claims description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
- 125000001424 substituent group Chemical group 0.000 claims description 2
- 239000011593 sulfur Substances 0.000 claims description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims 2
- LEONUFNNVUYDNQ-UHFFFAOYSA-N vanadium atom Chemical compound [V] LEONUFNNVUYDNQ-UHFFFAOYSA-N 0.000 claims 2
- 229910001413 alkali metal ion Inorganic materials 0.000 claims 1
- 229910021529 ammonia Inorganic materials 0.000 claims 1
- 125000004429 atom Chemical group 0.000 claims 1
- 238000002310 reflectometry Methods 0.000 abstract description 4
- 239000010410 layer Substances 0.000 description 44
- 239000010408 film Substances 0.000 description 34
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 12
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 12
- 239000000463 material Substances 0.000 description 12
- 239000004065 semiconductor Substances 0.000 description 12
- 239000002904 solvent Substances 0.000 description 12
- 235000012431 wafers Nutrition 0.000 description 12
- 239000007787 solid Substances 0.000 description 10
- 239000012756 surface treatment agent Substances 0.000 description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- -1 alkyl lithium compound Chemical class 0.000 description 9
- 230000000052 comparative effect Effects 0.000 description 9
- 230000003667 anti-reflective effect Effects 0.000 description 8
- 238000004519 manufacturing process Methods 0.000 description 8
- 239000012044 organic layer Substances 0.000 description 8
- 239000011230 binding agent Substances 0.000 description 7
- 125000002524 organometallic group Chemical group 0.000 description 7
- 239000011541 reaction mixture Substances 0.000 description 7
- QPRQEDXDYOZYLA-UHFFFAOYSA-N 2-methylbutan-1-ol Chemical compound CCC(C)CO QPRQEDXDYOZYLA-UHFFFAOYSA-N 0.000 description 6
- 239000003795 chemical substances by application Substances 0.000 description 6
- 238000010304 firing Methods 0.000 description 6
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 6
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 5
- CUJRVFIICFDLGR-UHFFFAOYSA-N acetylacetonate Chemical compound CC(=O)[CH-]C(C)=O CUJRVFIICFDLGR-UHFFFAOYSA-N 0.000 description 5
- 229910052710 silicon Inorganic materials 0.000 description 5
- 239000010703 silicon Substances 0.000 description 5
- 239000004094 surface-active agent Substances 0.000 description 5
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 description 4
- YRKCREAYFQTBPV-UHFFFAOYSA-N acetylacetone Chemical compound CC(=O)CC(C)=O YRKCREAYFQTBPV-UHFFFAOYSA-N 0.000 description 4
- 125000002947 alkylene group Chemical group 0.000 description 4
- 239000006117 anti-reflective coating Substances 0.000 description 4
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 4
- 239000012776 electronic material Substances 0.000 description 4
- 229910044991 metal oxide Inorganic materials 0.000 description 4
- 150000004706 metal oxides Chemical class 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- 238000004528 spin coating Methods 0.000 description 4
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000012298 atmosphere Substances 0.000 description 3
- 238000005229 chemical vapour deposition Methods 0.000 description 3
- 238000000151 deposition Methods 0.000 description 3
- 230000008021 deposition Effects 0.000 description 3
- 238000005530 etching Methods 0.000 description 3
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
- 230000003287 optical effect Effects 0.000 description 3
- 125000006832 (C1-C10) alkylene group Chemical group 0.000 description 2
- 125000006736 (C6-C20) aryl group Chemical group 0.000 description 2
- UXYMHGCNVRUGNO-UHFFFAOYSA-N 1-hydroxypropan-2-yl prop-2-enoate Chemical compound OCC(C)OC(=O)C=C UXYMHGCNVRUGNO-UHFFFAOYSA-N 0.000 description 2
- ARXJGSRGQADJSQ-UHFFFAOYSA-N 1-methoxypropan-2-ol Chemical compound COCC(C)O ARXJGSRGQADJSQ-UHFFFAOYSA-N 0.000 description 2
- WVYWICLMDOOCFB-UHFFFAOYSA-N 4-methyl-2-pentanol Chemical compound CC(C)CC(C)O WVYWICLMDOOCFB-UHFFFAOYSA-N 0.000 description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 125000002877 alkyl aryl group Chemical group 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 125000001118 alkylidene group Chemical group 0.000 description 2
- 125000000129 anionic group Chemical group 0.000 description 2
- 125000003710 aryl alkyl group Chemical group 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 238000011161 development Methods 0.000 description 2
- LZCLXQDLBQLTDK-UHFFFAOYSA-N ethyl 2-hydroxypropanoate Chemical compound CCOC(=O)C(C)O LZCLXQDLBQLTDK-UHFFFAOYSA-N 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 125000005842 heteroatom Chemical group 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical compound OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 238000001459 lithography Methods 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- 238000010907 mechanical stirring Methods 0.000 description 2
- 150000002739 metals Chemical class 0.000 description 2
- 230000007935 neutral effect Effects 0.000 description 2
- 150000004767 nitrides Chemical group 0.000 description 2
- 229910021420 polycrystalline silicon Inorganic materials 0.000 description 2
- 229920001343 polytetrafluoroethylene Polymers 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- 125000004642 (C1-C12) alkoxy group Chemical group 0.000 description 1
- 125000004400 (C1-C12) alkyl group Chemical group 0.000 description 1
- 125000003837 (C1-C20) alkyl group Chemical group 0.000 description 1
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 description 1
- 125000003161 (C1-C6) alkylene group Chemical group 0.000 description 1
- 229920002818 (Hydroxyethyl)methacrylate Polymers 0.000 description 1
- BPXVHIRIPLPOPT-UHFFFAOYSA-N 1,3,5-tris(2-hydroxyethyl)-1,3,5-triazinane-2,4,6-trione Chemical compound OCCN1C(=O)N(CCO)C(=O)N(CCO)C1=O BPXVHIRIPLPOPT-UHFFFAOYSA-N 0.000 description 1
- VNLSCKAQGGXPRI-UHFFFAOYSA-N 2,2,6,6-tetramethyl-3,5-dioxoheptanoic acid Chemical compound CC(C)(C)C(=O)CC(=O)C(C)(C)C(O)=O VNLSCKAQGGXPRI-UHFFFAOYSA-N 0.000 description 1
- QRIMLDXJAPZHJE-UHFFFAOYSA-N 2,3-dihydroxypropyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCC(O)CO QRIMLDXJAPZHJE-UHFFFAOYSA-N 0.000 description 1
- OWPUOLBODXJOKH-UHFFFAOYSA-N 2,3-dihydroxypropyl prop-2-enoate Chemical compound OCC(O)COC(=O)C=C OWPUOLBODXJOKH-UHFFFAOYSA-N 0.000 description 1
- NJRHMGPRPPEGQL-UHFFFAOYSA-N 2-hydroxybutyl prop-2-enoate Chemical compound CCC(O)COC(=O)C=C NJRHMGPRPPEGQL-UHFFFAOYSA-N 0.000 description 1
- OMIGHNLMNHATMP-UHFFFAOYSA-N 2-hydroxyethyl prop-2-enoate Chemical compound OCCOC(=O)C=C OMIGHNLMNHATMP-UHFFFAOYSA-N 0.000 description 1
- XLLXMBCBJGATSP-UHFFFAOYSA-N 2-phenylethenol Chemical compound OC=CC1=CC=CC=C1 XLLXMBCBJGATSP-UHFFFAOYSA-N 0.000 description 1
- GNSFRPWPOGYVLO-UHFFFAOYSA-N 3-hydroxypropyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCCO GNSFRPWPOGYVLO-UHFFFAOYSA-N 0.000 description 1
- QZPSOSOOLFHYRR-UHFFFAOYSA-N 3-hydroxypropyl prop-2-enoate Chemical compound OCCCOC(=O)C=C QZPSOSOOLFHYRR-UHFFFAOYSA-N 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical group [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- JBRZTFJDHDCESZ-UHFFFAOYSA-N AsGa Chemical compound [As]#[Ga] JBRZTFJDHDCESZ-UHFFFAOYSA-N 0.000 description 1
- SZYBURVQBPNOIJ-UHFFFAOYSA-N CC(=O)CC(C)=O.CC(=O)CC(C)=O.CCCCO[Hf]OCCCC Chemical compound CC(=O)CC(C)=O.CC(=O)CC(C)=O.CCCCO[Hf]OCCCC SZYBURVQBPNOIJ-UHFFFAOYSA-N 0.000 description 1
- MQIFVWRGUHSEBB-UHFFFAOYSA-N CC(=O)CC(C)=O.CC(=O)CC(C)=O.CCCCO[Zr]OCCCC Chemical compound CC(=O)CC(C)=O.CC(=O)CC(C)=O.CCCCO[Zr]OCCCC MQIFVWRGUHSEBB-UHFFFAOYSA-N 0.000 description 1
- 0 CC(C)(*)NOC Chemical compound CC(C)(*)NOC 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- 229910001218 Gallium arsenide Inorganic materials 0.000 description 1
- WOBHKFSMXKNTIM-UHFFFAOYSA-N Hydroxyethyl methacrylate Chemical compound CC(=C)C(=O)OCCO WOBHKFSMXKNTIM-UHFFFAOYSA-N 0.000 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 1
- XYVQFUJDGOBPQI-UHFFFAOYSA-N Methyl-2-hydoxyisobutyric acid Chemical compound COC(=O)C(C)(C)O XYVQFUJDGOBPQI-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 229910052581 Si3N4 Inorganic materials 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 229910000577 Silicon-germanium Inorganic materials 0.000 description 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
- LEVVHYCKPQWKOP-UHFFFAOYSA-N [Si].[Ge] Chemical compound [Si].[Ge] LEVVHYCKPQWKOP-UHFFFAOYSA-N 0.000 description 1
- 238000002835 absorbance Methods 0.000 description 1
- WDJHALXBUFZDSR-UHFFFAOYSA-M acetoacetate Chemical compound CC(=O)CC([O-])=O WDJHALXBUFZDSR-UHFFFAOYSA-M 0.000 description 1
- UNRQTHVKJQUDDF-UHFFFAOYSA-N acetylpyruvic acid Chemical compound CC(=O)CC(=O)C(O)=O UNRQTHVKJQUDDF-UHFFFAOYSA-N 0.000 description 1
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 229910052783 alkali metal Chemical group 0.000 description 1
- 150000001340 alkali metals Chemical group 0.000 description 1
- 229910003481 amorphous carbon Inorganic materials 0.000 description 1
- 238000013459 approach Methods 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 125000002843 carboxylic acid group Chemical group 0.000 description 1
- 238000005266 casting Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 229920001795 coordination polymer Polymers 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 238000007766 curtain coating Methods 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 239000000539 dimer Substances 0.000 description 1
- 238000003618 dip coating Methods 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000007606 doctor blade method Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- HLOLVQSTCUVLJD-UHFFFAOYSA-N ethyl 3-oxobutanoate 3-oxohexanoic acid Chemical compound CCCC(=O)CC(O)=O.CCOC(=O)CC(C)=O HLOLVQSTCUVLJD-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 229940116333 ethyl lactate Drugs 0.000 description 1
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 1
- 238000011049 filling Methods 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- 239000010931 gold Substances 0.000 description 1
- 238000009499 grossing Methods 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 230000002706 hydrostatic effect Effects 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 238000005286 illumination Methods 0.000 description 1
- 238000000671 immersion lithography Methods 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 239000002198 insoluble material Substances 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 150000002596 lactones Chemical class 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- AUHZEENZYGFFBQ-UHFFFAOYSA-N mesitylene Substances CC1=CC(C)=CC(C)=C1 AUHZEENZYGFFBQ-UHFFFAOYSA-N 0.000 description 1
- 125000001827 mesitylenyl group Chemical group [H]C1=C(C(*)=C(C([H])=C1C([H])([H])[H])C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 150000002736 metal compounds Chemical class 0.000 description 1
- 238000004377 microelectronic Methods 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- JESXATFQYMPTNL-UHFFFAOYSA-N mono-hydroxyphenyl-ethylene Natural products OC1=CC=CC=C1C=C JESXATFQYMPTNL-UHFFFAOYSA-N 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 238000004806 packaging method and process Methods 0.000 description 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 1
- 238000000206 photolithography Methods 0.000 description 1
- 238000001020 plasma etching Methods 0.000 description 1
- 229920006254 polymer film Polymers 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 229920005862 polyol Polymers 0.000 description 1
- 150000003077 polyols Chemical class 0.000 description 1
- 229920005591 polysilicon Polymers 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- LLHKCFNBLRBOGN-UHFFFAOYSA-N propylene glycol methyl ether acetate Chemical compound COCC(C)OC(C)=O LLHKCFNBLRBOGN-UHFFFAOYSA-N 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000010791 quenching Methods 0.000 description 1
- 230000000171 quenching effect Effects 0.000 description 1
- 229910052594 sapphire Inorganic materials 0.000 description 1
- 239000010980 sapphire Substances 0.000 description 1
- HQVNEWCFYHHQES-UHFFFAOYSA-N silicon nitride Chemical compound N12[Si]34N5[Si]62N3[Si]51N64 HQVNEWCFYHHQES-UHFFFAOYSA-N 0.000 description 1
- 229910052814 silicon oxide Inorganic materials 0.000 description 1
- 238000007764 slot die coating Methods 0.000 description 1
- 229910000679 solder Inorganic materials 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 230000003068 static effect Effects 0.000 description 1
- 239000012258 stirred mixture Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 125000000542 sulfonic acid group Chemical group 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- MAKDTFFYCIMFQP-UHFFFAOYSA-N titanium tungsten Chemical compound [Ti].[W] MAKDTFFYCIMFQP-UHFFFAOYSA-N 0.000 description 1
- 239000013638 trimer Substances 0.000 description 1
- GPPXJZIENCGNKB-UHFFFAOYSA-N vanadium Chemical compound [V]#[V] GPPXJZIENCGNKB-UHFFFAOYSA-N 0.000 description 1
- 238000007740 vapor deposition Methods 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- 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
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Abstract
【解決手段】式(1)で表される有機金属化合物及び、前記有機金属化合物と、有機溶媒と、を含む組成物。
〔R2は(C1−20)ヒドロカルビル;M1はグループ3〜14の金属;GはR3b−Ch−R3b又はCh(OM1L1mOR2)c;Chは発色団部分;R3はC1〜12の2価の連結基;R4はH、R2又はM(L1)mOR2;L1はリガンド;mはリガンドの数、かつ1〜4の整数;aは1〜20の整数;各bはそれぞれ0〜25の整数;c=1または2〕
【選択図】なし
Description
発色団部分を含む有機金属オリゴマーを次のように調整した。Dean−Starkトラップを備えたフラスコに、Ti(OR)2(acac)2(R=n−ブチルまたはイソプロピル、Tyzor AA−105、デュポン社から市販)、および0.33等量のtris−(2−ヒドロキシエチル)イソシアヌレート(RCEIC)を添加した。この混合物を120〜130℃に加熱し、1〜2日間撹拌し、蒸留回収した。混合物をヘプタン(500ml)中で冷却し、急冷した。析出した固体を真空中で乾燥し、以下の式1に示す、13gの所望の製品、ポリマーAを得た。
式1:
ジルコニウム−ビス(アセチルアセトン)−ビス(n−ブトキシド)(またはZr(acac)2(OBu)2)を0.33等量のTCEICと反応させること以外は実施例1の手順を繰り返し、ポリマーBを得る。
ハフニウム−ビス(アセチルアセトン)−ビス(n−ブトキシド)(またはHf(acac)2(OBu)2)を0.33等量のTCEICと反応させること以外は実施例1の手順を繰り返し、ポリマーCを得る。
ポリマーAおよび比較ポリマーを、それぞれ固形分3.5wt%で2−メチル−1−ブタノールとガンマ‐ブチロラクトンとの混合物(95/5重量比)により調合し、0.2μmのポリ(テトラフルオロエチレン)(PTFE)シリンジフィルタを介して濾過した。得られた溶液を、1500rpmでAR(商標)26Antireflectant(Dow Electronic Materialsより入手可能)の層を有するシリコンウエハ上に塗布し、280℃で60秒間焼成した。次に、市販のフォトレジスト(193nmまたは248nmのレジストのいずれか、Dow Electronic Materialsより入手可能)の層を、ポリマーAおよび比較ポリマーの両方の表面にスピンコートした。得られた高分子膜のn/k値をVUV−VASE(J.A.Woolam Co.Inc.)を用いて測定し、基板の反射率を表1に示す条件でKLA−Tencor社製のProlith(商標)ソフトウェアにより算出した。
5L三口フラスコに、還流コンデンサ、機械撹拌機および入口アダプタを備えた。この反応器に、400gのHf(OBu)4(0.85mol)、および2.3Lの無水テトラヒドロフラン(THF)を添加し、この混合物を、機械撹拌を用いて激しく撹拌した。この撹拌混合物に、Scilogポンプを介して6時間かけて700mlの無水THF、およびペンタン−2,4−ジオン(170g、1.7mol)の溶液を添加した。反応混合物を室温で一晩撹拌した。その後、反応混合物を真空下で減圧乾燥した。無水酢酸エチル800mlを添加し、混合物を数時間室温で激しく撹拌した。この溶液を、微細フリットで濾過して、あらゆる不溶物を除去した。真空下で溶媒を濾液から除去し、ペールホワイトの固体(Hf(acac)2(OBu)2)を得て(288.5g、65%収率)、さらなる精製を行うことなく使用した。
2Lの三口フラスコに、還流コンデンサ、機械撹拌および熱電対を備えた。このフラスコに、実施例6(288.5g、0.55mol)からのHf(acac)2(OBu)2の無水酢酸エチル(1.3L)溶液、およびエチレンジグリコール(55.5g、0.52mol)を添加し、反応混合物を80°Cで16〜18時間還流した。次に、溶液を25℃まで冷却した後、微細フリットで濾過して、あらゆる析出した固体(94g)を除去した。濾液量を減らした後、一晩撹拌しながら、10倍量のヘプタンで急冷した。固体を収集し、ヘプタン(3×1L)で3回洗浄した。白色粉末を2時間強い真空下で乾燥し、式3に示す比較ポリマー2である、135gの白色のポリマーを得た。
式3:
500ml三口フラスコに、機械撹拌器、コンデンサ、入口ストッパー、ガス導入口を備え、N2のブランケット下で、50gのHf(OBu)4(0.106モル)、および150mlの無水THFを添加した。ペンタン−2,4−ジオンの溶液(2等量)、および50mlの無水THFを6時間かけてScilogポンプを介して添加し、反応混合物を一晩撹拌した。THFを減圧下で除去し、得られた白色固体を、無水酢酸エチル400mlで2〜3時間溶出して、全固体を溶解した。反応混合物を500ml三口フラスコに移し、1,4−ジアルコキシサルフェートを添加した。反応混合物を、100ml酢酸エチルを除去しながら加熱還流し、18時間還流で保持した。その後、反応混合物を室温まで冷却し、次いで100〜150mlに濃縮し、続いて10倍量のヘプタンで急冷すると、ゴム状の固体に凝固した自由流動個体を得た。これを、ゴム状の物質を処置する間、ヘプタン中に放置した。ゴム状の材料は、自由流動性となって、これを一晩撹拌しながら放置した。固体を集め、ヘプタンで洗浄後、その後40℃で真空乾燥して、式(4)に示す、ポリマーDである、41gの製品を得た。
式4:
ポリマーD、比較ポリマー2、およびポリマーDと比較ポリマー2との1:1の混合物を使用した以外は、実施例5の手順を繰り返した。データを表3に示す。ポリマーD自体で、および比較ポリマー2との組み合わせにより、減少した反射率が得られることが明示されている。
Claims (14)
- M1がチタン、ジルコニウム、ハフニウム、タングステン、タンタル、モリブデン、バナジウム、インジウム、ゲルマニウム、ガリウム、タリウム、およびアルミニウムから選択される、請求項1に記載の組成物。
- 各L1が(C1−C20)アルコキシ、(C2−C20)カルボキシル、β−ジケトナート、β−ヒドロキシケトナート、β−ケトエステル、β−ジケチミネート、アミジナート、グアニジナート、またはβ−ヒドロキシイミネートから選択される、請求項1に記載の組成物。
- 前記発色団部分が1つ以上の芳香環、またはイソシアヌレートを含む、請求項1に記載の組成物。
- 前記芳香環がフェニル、ナフチル、アントラセニル、フェナントリルから選択される、請求項4に記載の組成物。
- 20〜40erg/cm2の表面エネルギーを有し、ヒドロキシル、保護ヒドロキシル、保護カルボキシル、またはそれらの混合物から選択された表面処理部分を含む、表面処理ポリマーを更に含む、請求項1に記載の組成物。
- R3が、酸素、窒素、硫黄の群から選択された1以上の原子を含む、請求項1に記載の組成物。
- R3が、(C2−C12)アルキレン−O−および(C2−C12)アルキリデン−O−からなる群から選択される、請求項1に記載の組成物。
- Gが、Ch、Ch−R3 b、R3 b−ChまたはCh(OM1L1 mOR2)cから選択される、請求項1に記載の組成物。
- (C1−C6)アルキル、シアノ、ハロ、ニトロおよびSO3−Y(ここでY=H、アンモニア、またはアルカリ金属イオン)から成る群から選択される1以上の置換基によって前記発色団部分が置換されている、請求項1に記載の組成物。
- 基板を提供する工程と、
基板の表面上に請求項1の組成物の膜をコーティングする工程と、
前記発色団部分を有する金属ハードマスク層を形成するのに十分な条件下で膜を硬化する工程と、
を含む、金属ハードマスク層を形成する方法。 - M1がチタン、ジルコニウム、ハフニウム、タングステン、タンタル、モリブデン、バナジウム、インジウム、ゲルマニウム、ガリウム、タリウム、およびアルミニウムから選択される、請求項11に記載の方法。
- 前記発色団部分が1つ以上の芳香環およびイソシアヌレートを含む、請求項11に記載の方法。
- 硬化された前記金属ハードマスク層上にフォトレジストの層を配置する工程と、
パターン化放射によって前記フォトレジストを露光して画像を形成する工程と、
を更に含む、請求項11に記載の方法。
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CN104635424A (zh) | 2015-05-20 |
CN104635424B (zh) | 2019-10-18 |
JP6578092B2 (ja) | 2019-09-18 |
KR102307612B1 (ko) | 2021-10-01 |
US9563126B2 (en) | 2017-02-07 |
US20150064612A1 (en) | 2015-03-05 |
KR20150027012A (ko) | 2015-03-11 |
TWI565762B (zh) | 2017-01-11 |
TW201520279A (zh) | 2015-06-01 |
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US9296879B2 (en) | 2016-03-29 |
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