JP7526761B2 - オーバーコートフォトレジスト用のコーティングされた下層 - Google Patents
オーバーコートフォトレジスト用のコーティングされた下層 Download PDFInfo
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- JP7526761B2 JP7526761B2 JP2022102299A JP2022102299A JP7526761B2 JP 7526761 B2 JP7526761 B2 JP 7526761B2 JP 2022102299 A JP2022102299 A JP 2022102299A JP 2022102299 A JP2022102299 A JP 2022102299A JP 7526761 B2 JP7526761 B2 JP 7526761B2
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- Prior art keywords
- substituted
- unsubstituted
- alkyl
- aryl
- heteroaryl
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- 229920002120 photoresistant polymer Polymers 0.000 title claims description 58
- 239000010410 layer Substances 0.000 claims description 103
- 239000008199 coating composition Substances 0.000 claims description 65
- 125000003118 aryl group Chemical group 0.000 claims description 59
- 239000000758 substrate Substances 0.000 claims description 56
- 125000000217 alkyl group Chemical group 0.000 claims description 55
- 229920000642 polymer Polymers 0.000 claims description 47
- 125000001072 heteroaryl group Chemical group 0.000 claims description 38
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 36
- 239000000463 material Substances 0.000 claims description 36
- 239000000654 additive Substances 0.000 claims description 32
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 32
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 32
- 229910052739 hydrogen Inorganic materials 0.000 claims description 31
- 238000000034 method Methods 0.000 claims description 31
- 125000004446 heteroarylalkyl group Chemical group 0.000 claims description 30
- 239000001257 hydrogen Substances 0.000 claims description 30
- 125000002877 alkyl aryl group Chemical group 0.000 claims description 26
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 26
- 239000002904 solvent Substances 0.000 claims description 26
- 230000000996 additive effect Effects 0.000 claims description 24
- 239000000178 monomer Substances 0.000 claims description 19
- 125000005213 alkyl heteroaryl group Chemical group 0.000 claims description 17
- 125000004404 heteroalkyl group Chemical group 0.000 claims description 15
- 150000001875 compounds Chemical class 0.000 claims description 14
- 125000005647 linker group Chemical group 0.000 claims description 14
- 229910052710 silicon Inorganic materials 0.000 claims description 14
- 125000000739 C2-C30 alkenyl group Chemical group 0.000 claims description 13
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 claims description 13
- 125000002947 alkylene group Chemical group 0.000 claims description 13
- 239000010703 silicon Substances 0.000 claims description 13
- 125000006651 (C3-C20) cycloalkyl group Chemical group 0.000 claims description 12
- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 claims description 12
- 229910052731 fluorine Inorganic materials 0.000 claims description 11
- 239000011737 fluorine Substances 0.000 claims description 11
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 10
- 239000006117 anti-reflective coating Substances 0.000 claims description 8
- 229910052736 halogen Inorganic materials 0.000 claims description 8
- 150000002367 halogens Chemical class 0.000 claims description 8
- 125000003277 amino group Chemical group 0.000 claims description 7
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 7
- 125000003709 fluoroalkyl group Chemical group 0.000 claims description 6
- 125000004366 heterocycloalkenyl group Chemical group 0.000 claims description 6
- 150000003573 thiols Chemical class 0.000 claims description 6
- 125000003358 C2-C20 alkenyl group Chemical group 0.000 claims description 5
- 125000003342 alkenyl group Chemical group 0.000 claims description 4
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 claims description 4
- 150000002431 hydrogen Chemical class 0.000 claims 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 29
- 239000000203 mixture Substances 0.000 description 26
- 125000005842 heteroatom Chemical group 0.000 description 18
- 239000002253 acid Substances 0.000 description 16
- 239000004065 semiconductor Substances 0.000 description 15
- 239000004094 surface-active agent Substances 0.000 description 14
- 235000012431 wafers Nutrition 0.000 description 14
- 239000007787 solid Substances 0.000 description 13
- 239000000243 solution Substances 0.000 description 13
- 125000004432 carbon atom Chemical group C* 0.000 description 12
- 239000003963 antioxidant agent Substances 0.000 description 11
- 229910052799 carbon Inorganic materials 0.000 description 11
- -1 diphenylene ether Chemical compound 0.000 description 11
- 125000005549 heteroarylene group Chemical group 0.000 description 11
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 10
- 125000001424 substituent group Chemical group 0.000 description 10
- 125000000732 arylene group Chemical group 0.000 description 9
- 125000002993 cycloalkylene group Chemical group 0.000 description 9
- 125000006588 heterocycloalkylene group Chemical group 0.000 description 9
- 238000012546 transfer Methods 0.000 description 9
- 239000003431 cross linking reagent Substances 0.000 description 8
- 238000005227 gel permeation chromatography Methods 0.000 description 7
- 229910052757 nitrogen Inorganic materials 0.000 description 7
- 229910052760 oxygen Inorganic materials 0.000 description 7
- LLHKCFNBLRBOGN-UHFFFAOYSA-N propylene glycol methyl ether acetate Chemical compound COCC(C)OC(C)=O LLHKCFNBLRBOGN-UHFFFAOYSA-N 0.000 description 7
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- 125000004093 cyano group Chemical group *C#N 0.000 description 6
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- 238000004519 manufacturing process Methods 0.000 description 6
- 230000005855 radiation Effects 0.000 description 6
- 238000004528 spin coating Methods 0.000 description 6
- WGTYBPLFGIVFAS-UHFFFAOYSA-M tetramethylammonium hydroxide Chemical compound [OH-].C[N+](C)(C)C WGTYBPLFGIVFAS-UHFFFAOYSA-M 0.000 description 6
- 230000003213 activating effect Effects 0.000 description 5
- 125000000304 alkynyl group Chemical group 0.000 description 5
- 125000006242 amine protecting group Chemical group 0.000 description 5
- 150000001721 carbon Chemical group 0.000 description 5
- 239000011247 coating layer Substances 0.000 description 5
- 230000000052 comparative effect Effects 0.000 description 5
- 125000001153 fluoro group Chemical group F* 0.000 description 5
- 125000003367 polycyclic group Chemical group 0.000 description 5
- 229910052717 sulfur Inorganic materials 0.000 description 5
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 4
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 4
- 229910052581 Si3N4 Inorganic materials 0.000 description 4
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical class CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- 239000011248 coating agent Substances 0.000 description 4
- 238000000576 coating method Methods 0.000 description 4
- 230000032798 delamination Effects 0.000 description 4
- 150000002148 esters Chemical class 0.000 description 4
- 238000005530 etching Methods 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
- 125000004433 nitrogen atom Chemical group N* 0.000 description 4
- 238000000059 patterning Methods 0.000 description 4
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 4
- 125000006239 protecting group Chemical group 0.000 description 4
- HQVNEWCFYHHQES-UHFFFAOYSA-N silicon nitride Chemical compound N12[Si]34N5[Si]62N3[Si]51N64 HQVNEWCFYHHQES-UHFFFAOYSA-N 0.000 description 4
- 238000003786 synthesis reaction Methods 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- 125000000923 (C1-C30) alkyl group Chemical group 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical class C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
- 239000004793 Polystyrene Substances 0.000 description 3
- 125000002252 acyl group Chemical group 0.000 description 3
- 125000003545 alkoxy group Chemical group 0.000 description 3
- 239000000908 ammonium hydroxide Substances 0.000 description 3
- 229910003481 amorphous carbon Inorganic materials 0.000 description 3
- 239000002585 base Substances 0.000 description 3
- 235000010290 biphenyl Nutrition 0.000 description 3
- 239000004305 biphenyl Substances 0.000 description 3
- 125000001246 bromo group Chemical group Br* 0.000 description 3
- 239000011203 carbon fibre reinforced carbon Substances 0.000 description 3
- 238000005229 chemical vapour deposition Methods 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 238000009472 formulation Methods 0.000 description 3
- 150000002430 hydrocarbons Chemical group 0.000 description 3
- 239000003999 initiator Substances 0.000 description 3
- 239000012528 membrane Substances 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- 125000001624 naphthyl group Chemical group 0.000 description 3
- 229920003986 novolac Polymers 0.000 description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
- 229910021420 polycrystalline silicon Inorganic materials 0.000 description 3
- 229920001223 polyethylene glycol Polymers 0.000 description 3
- 150000008442 polyphenolic compounds Chemical class 0.000 description 3
- 235000013824 polyphenols Nutrition 0.000 description 3
- 229920002223 polystyrene Polymers 0.000 description 3
- 238000012545 processing Methods 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- 238000009482 thermal adhesion granulation Methods 0.000 description 3
- MCJPJAJHPRCILL-UHFFFAOYSA-N (2,6-dinitrophenyl)methyl 4-methylbenzenesulfonate Chemical compound C1=CC(C)=CC=C1S(=O)(=O)OCC1=C([N+]([O-])=O)C=CC=C1[N+]([O-])=O MCJPJAJHPRCILL-UHFFFAOYSA-N 0.000 description 2
- HNURKXXMYARGAY-UHFFFAOYSA-N 2,6-Di-tert-butyl-4-hydroxymethylphenol Chemical compound CC(C)(C)C1=CC(CO)=CC(C(C)(C)C)=C1O HNURKXXMYARGAY-UHFFFAOYSA-N 0.000 description 2
- BVUXDWXKPROUDO-UHFFFAOYSA-N 2,6-di-tert-butyl-4-ethylphenol Chemical compound CCC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 BVUXDWXKPROUDO-UHFFFAOYSA-N 0.000 description 2
- BWLBGMIXKSTLSX-UHFFFAOYSA-N 2-hydroxyisobutyric acid Chemical compound CC(C)(O)C(O)=O BWLBGMIXKSTLSX-UHFFFAOYSA-N 0.000 description 2
- XLLIQLLCWZCATF-UHFFFAOYSA-N 2-methoxyethyl acetate Chemical compound COCCOC(C)=O XLLIQLLCWZCATF-UHFFFAOYSA-N 0.000 description 2
- VPWNQTHUCYMVMZ-UHFFFAOYSA-N 4,4'-sulfonyldiphenol Chemical class C1=CC(O)=CC=C1S(=O)(=O)C1=CC=C(O)C=C1 VPWNQTHUCYMVMZ-UHFFFAOYSA-N 0.000 description 2
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 description 2
- FAUAZXVRLVIARB-UHFFFAOYSA-N 4-[[4-[bis(oxiran-2-ylmethyl)amino]phenyl]methyl]-n,n-bis(oxiran-2-ylmethyl)aniline Chemical compound C1OC1CN(C=1C=CC(CC=2C=CC(=CC=2)N(CC2OC2)CC2OC2)=CC=1)CC1CO1 FAUAZXVRLVIARB-UHFFFAOYSA-N 0.000 description 2
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 2
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 2
- 239000004593 Epoxy Substances 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical class OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical class C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- XOJVVFBFDXDTEG-UHFFFAOYSA-N Norphytane Natural products CC(C)CCCC(C)CCCC(C)CCCC(C)C XOJVVFBFDXDTEG-UHFFFAOYSA-N 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 2
- WYGWHHGCAGTUCH-ISLYRVAYSA-N V-65 Substances CC(C)CC(C)(C#N)\N=N\C(C)(C#N)CC(C)C WYGWHHGCAGTUCH-ISLYRVAYSA-N 0.000 description 2
- DCYQPMGIYRPCBA-UHFFFAOYSA-N [2,3-bis(trifluoromethylsulfonyloxy)phenyl] trifluoromethanesulfonate Chemical compound FC(F)(F)S(=O)(=O)OC1=CC=CC(OS(=O)(=O)C(F)(F)F)=C1OS(=O)(=O)C(F)(F)F DCYQPMGIYRPCBA-UHFFFAOYSA-N 0.000 description 2
- 125000004450 alkenylene group Chemical group 0.000 description 2
- 229910052782 aluminium Inorganic materials 0.000 description 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 2
- 150000001408 amides Chemical class 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical class C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 2
- 239000012298 atmosphere Substances 0.000 description 2
- WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 2
- 150000005347 biaryls Chemical group 0.000 description 2
- ZDZHCHYQNPQSGG-UHFFFAOYSA-N binaphthyl group Chemical group C1(=CC=CC2=CC=CC=C12)C1=CC=CC2=CC=CC=C12 ZDZHCHYQNPQSGG-UHFFFAOYSA-N 0.000 description 2
- 230000005587 bubbling Effects 0.000 description 2
- 150000004657 carbamic acid derivatives Chemical class 0.000 description 2
- 230000015556 catabolic process Effects 0.000 description 2
- YCIMNLLNPGFGHC-UHFFFAOYSA-N catechol Chemical compound OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 description 2
- 125000001309 chloro group Chemical group Cl* 0.000 description 2
- 238000004140 cleaning Methods 0.000 description 2
- 229920001577 copolymer Polymers 0.000 description 2
- 229910052802 copper Inorganic materials 0.000 description 2
- 239000010949 copper Substances 0.000 description 2
- 238000004132 cross linking Methods 0.000 description 2
- 238000013036 cure process Methods 0.000 description 2
- 238000006731 degradation reaction Methods 0.000 description 2
- 238000010511 deprotection reaction Methods 0.000 description 2
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 125000003700 epoxy group Chemical group 0.000 description 2
- LZCLXQDLBQLTDK-UHFFFAOYSA-N ethyl 2-hydroxypropanoate Chemical compound CCOC(=O)C(C)O LZCLXQDLBQLTDK-UHFFFAOYSA-N 0.000 description 2
- 238000011156 evaluation Methods 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 125000005843 halogen group Chemical group 0.000 description 2
- 230000002209 hydrophobic effect Effects 0.000 description 2
- 238000003384 imaging method Methods 0.000 description 2
- 230000010354 integration Effects 0.000 description 2
- 125000002346 iodo group Chemical group I* 0.000 description 2
- 238000001459 lithography Methods 0.000 description 2
- 238000004518 low pressure chemical vapour deposition Methods 0.000 description 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 2
- 125000002950 monocyclic group Chemical group 0.000 description 2
- 239000002736 nonionic surfactant Substances 0.000 description 2
- 230000003287 optical effect Effects 0.000 description 2
- 150000007524 organic acids Chemical class 0.000 description 2
- 239000012044 organic layer Substances 0.000 description 2
- 125000004430 oxygen atom Chemical group O* 0.000 description 2
- 239000002530 phenolic antioxidant Substances 0.000 description 2
- 150000002989 phenols Chemical class 0.000 description 2
- 238000005240 physical vapour deposition Methods 0.000 description 2
- 238000000623 plasma-assisted chemical vapour deposition Methods 0.000 description 2
- 229920000647 polyepoxide Polymers 0.000 description 2
- 229920005591 polysilicon Polymers 0.000 description 2
- 229920001343 polytetrafluoroethylene Polymers 0.000 description 2
- 239000004810 polytetrafluoroethylene Substances 0.000 description 2
- 125000006413 ring segment Chemical group 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 description 2
- 229910052814 silicon oxide Inorganic materials 0.000 description 2
- 125000004434 sulfur atom Chemical group 0.000 description 2
- XBXCNNQPRYLIDE-UHFFFAOYSA-N tert-butylcarbamic acid Chemical compound CC(C)(C)NC(O)=O XBXCNNQPRYLIDE-UHFFFAOYSA-N 0.000 description 2
- 239000010936 titanium Substances 0.000 description 2
- 229910052719 titanium Inorganic materials 0.000 description 2
- 238000011282 treatment Methods 0.000 description 2
- BZVJOYBTLHNRDW-UHFFFAOYSA-N triphenylmethanamine Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)(N)C1=CC=CC=C1 BZVJOYBTLHNRDW-UHFFFAOYSA-N 0.000 description 2
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 description 2
- 229910052721 tungsten Inorganic materials 0.000 description 2
- 239000010937 tungsten Substances 0.000 description 2
- 238000011179 visual inspection Methods 0.000 description 2
- GCIYMCNGLUNWNR-UHFFFAOYSA-N (2,4-dinitrophenyl)methyl 4-methylbenzenesulfonate Chemical compound C1=CC(C)=CC=C1S(=O)(=O)OCC1=CC=C([N+]([O-])=O)C=C1[N+]([O-])=O GCIYMCNGLUNWNR-UHFFFAOYSA-N 0.000 description 1
- MCVVDMSWCQUKEV-UHFFFAOYSA-N (2-nitrophenyl)methyl 4-methylbenzenesulfonate Chemical compound C1=CC(C)=CC=C1S(=O)(=O)OCC1=CC=CC=C1[N+]([O-])=O MCVVDMSWCQUKEV-UHFFFAOYSA-N 0.000 description 1
- QXTKWWMLNUQOLB-UHFFFAOYSA-N (4-nitrophenyl)methyl 4-methylbenzenesulfonate Chemical compound C1=CC(C)=CC=C1S(=O)(=O)OCC1=CC=C([N+]([O-])=O)C=C1 QXTKWWMLNUQOLB-UHFFFAOYSA-N 0.000 description 1
- 125000003837 (C1-C20) alkyl group Chemical group 0.000 description 1
- 125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 description 1
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 description 1
- 125000004737 (C1-C6) haloalkoxy group Chemical group 0.000 description 1
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 description 1
- 125000006652 (C3-C12) cycloalkyl group Chemical group 0.000 description 1
- 125000006654 (C3-C12) heteroaryl group Chemical group 0.000 description 1
- LJHFIVQEAFAURQ-ZPUQHVIOSA-N (NE)-N-[(2E)-2-hydroxyiminoethylidene]hydroxylamine Chemical class O\N=C\C=N\O LJHFIVQEAFAURQ-ZPUQHVIOSA-N 0.000 description 1
- MIOPJNTWMNEORI-GMSGAONNSA-N (S)-camphorsulfonic acid Chemical class C1C[C@@]2(CS(O)(=O)=O)C(=O)C[C@@H]1C2(C)C MIOPJNTWMNEORI-GMSGAONNSA-N 0.000 description 1
- VZXTWGWHSMCWGA-UHFFFAOYSA-N 1,3,5-triazine-2,4-diamine Chemical class NC1=NC=NC(N)=N1 VZXTWGWHSMCWGA-UHFFFAOYSA-N 0.000 description 1
- OUPZKGBUJRBPGC-UHFFFAOYSA-N 1,3,5-tris(oxiran-2-ylmethyl)-1,3,5-triazinane-2,4,6-trione Chemical compound O=C1N(CC2OC2)C(=O)N(CC2OC2)C(=O)N1CC1CO1 OUPZKGBUJRBPGC-UHFFFAOYSA-N 0.000 description 1
- GYQQFWWMZYBCIB-UHFFFAOYSA-N 1-[diazo-(4-methylphenyl)sulfonylmethyl]sulfonyl-4-methylbenzene Chemical compound C1=CC(C)=CC=C1S(=O)(=O)C(=[N+]=[N-])S(=O)(=O)C1=CC=C(C)C=C1 GYQQFWWMZYBCIB-UHFFFAOYSA-N 0.000 description 1
- HMNZROFMBSUMAB-UHFFFAOYSA-N 1-ethoxybutan-1-ol Chemical group CCCC(O)OCC HMNZROFMBSUMAB-UHFFFAOYSA-N 0.000 description 1
- JLBXCKSMESLGTJ-UHFFFAOYSA-N 1-ethoxypropan-1-ol Chemical group CCOC(O)CC JLBXCKSMESLGTJ-UHFFFAOYSA-N 0.000 description 1
- FFKFRQVYUILJCW-UHFFFAOYSA-N 1-hydroxypyrrolidine-2,5-dione;methanesulfonic acid Chemical compound CS(O)(=O)=O.ON1C(=O)CCC1=O FFKFRQVYUILJCW-UHFFFAOYSA-N 0.000 description 1
- QPAWHGVDCJWYRJ-UHFFFAOYSA-N 1-hydroxypyrrolidine-2,5-dione;trifluoromethanesulfonic acid Chemical compound ON1C(=O)CCC1=O.OS(=O)(=O)C(F)(F)F QPAWHGVDCJWYRJ-UHFFFAOYSA-N 0.000 description 1
- LHENQXAPVKABON-UHFFFAOYSA-N 1-methoxypropan-1-ol Chemical group CCC(O)OC LHENQXAPVKABON-UHFFFAOYSA-N 0.000 description 1
- ARXJGSRGQADJSQ-UHFFFAOYSA-N 1-methoxypropan-2-ol Chemical compound COCC(C)O ARXJGSRGQADJSQ-UHFFFAOYSA-N 0.000 description 1
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- 229910052750 molybdenum Inorganic materials 0.000 description 1
- 239000011733 molybdenum Substances 0.000 description 1
- 229910021421 monocrystalline silicon Inorganic materials 0.000 description 1
- WFMDRIAQYUQXQQ-UHFFFAOYSA-M n-tert-butyl-n-(4-hydroxycyclohexyl)carbamate Chemical compound CC(C)(C)N(C([O-])=O)C1CCC(O)CC1 WFMDRIAQYUQXQQ-UHFFFAOYSA-M 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 150000004767 nitrides Chemical class 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 125000006502 nitrobenzyl group Chemical group 0.000 description 1
- 229920000847 nonoxynol Polymers 0.000 description 1
- SSDSCDGVMJFTEQ-UHFFFAOYSA-N octadecyl 3-(3,5-ditert-butyl-4-hydroxyphenyl)propanoate Chemical compound CCCCCCCCCCCCCCCCCCOC(=O)CCC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 SSDSCDGVMJFTEQ-UHFFFAOYSA-N 0.000 description 1
- 229920002113 octoxynol Polymers 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000010943 off-gassing Methods 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 239000011368 organic material Substances 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 150000002931 p-cresols Chemical class 0.000 description 1
- 238000004806 packaging method and process Methods 0.000 description 1
- UCUUFSAXZMGPGH-UHFFFAOYSA-N penta-1,4-dien-3-one Chemical compound C=CC(=O)C=C UCUUFSAXZMGPGH-UHFFFAOYSA-N 0.000 description 1
- JGTNAGYHADQMCM-UHFFFAOYSA-N perfluorobutanesulfonic acid Chemical class OS(=O)(=O)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F JGTNAGYHADQMCM-UHFFFAOYSA-N 0.000 description 1
- 229940044652 phenolsulfonate Drugs 0.000 description 1
- AFDMODCXODAXLC-UHFFFAOYSA-N phenylmethanimine Chemical compound N=CC1=CC=CC=C1 AFDMODCXODAXLC-UHFFFAOYSA-N 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 238000001020 plasma etching Methods 0.000 description 1
- 229920001983 poloxamer Polymers 0.000 description 1
- 229920000233 poly(alkylene oxides) Polymers 0.000 description 1
- 229920002454 poly(glycidyl methacrylate) polymer Polymers 0.000 description 1
- 229920000636 poly(norbornene) polymer Polymers 0.000 description 1
- 229920002401 polyacrylamide Polymers 0.000 description 1
- 229920000058 polyacrylate Polymers 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 239000003505 polymerization initiator Substances 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 229920006324 polyoxymethylene Polymers 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 235000019422 polyvinyl alcohol Nutrition 0.000 description 1
- 229920001289 polyvinyl ether Polymers 0.000 description 1
- RUOJZAUFBMNUDX-UHFFFAOYSA-N propylene carbonate Chemical compound CC1COC(=O)O1 RUOJZAUFBMNUDX-UHFFFAOYSA-N 0.000 description 1
- DNIAPMSPPWPWGF-UHFFFAOYSA-N propylene glycol Substances CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000002310 reflectometry Methods 0.000 description 1
- 238000007761 roller coating Methods 0.000 description 1
- 238000002390 rotary evaporation Methods 0.000 description 1
- 229910052594 sapphire Inorganic materials 0.000 description 1
- 239000010980 sapphire Substances 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 229930195734 saturated hydrocarbon Natural products 0.000 description 1
- 150000003333 secondary alcohols Chemical class 0.000 description 1
- 229910021332 silicide Inorganic materials 0.000 description 1
- LIVNPJMFVYWSIS-UHFFFAOYSA-N silicon monoxide Chemical compound [Si-]#[O+] LIVNPJMFVYWSIS-UHFFFAOYSA-N 0.000 description 1
- 239000002356 single layer Substances 0.000 description 1
- 238000007764 slot die coating Methods 0.000 description 1
- 229910000679 solder Inorganic materials 0.000 description 1
- 238000009987 spinning Methods 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 238000004544 sputter deposition Methods 0.000 description 1
- 238000000859 sublimation Methods 0.000 description 1
- 230000008022 sublimation Effects 0.000 description 1
- 150000003871 sulfonates Chemical class 0.000 description 1
- 150000003459 sulfonic acid esters Chemical class 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 229910052715 tantalum Inorganic materials 0.000 description 1
- GUVRBAGPIYLISA-UHFFFAOYSA-N tantalum atom Chemical compound [Ta] GUVRBAGPIYLISA-UHFFFAOYSA-N 0.000 description 1
- 238000010345 tape casting Methods 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- GPTXCAZYUMDUMN-UHFFFAOYSA-N tert-butyl n-(2-hydroxyethyl)carbamate Chemical compound CC(C)(C)OC(=O)NCCO GPTXCAZYUMDUMN-UHFFFAOYSA-N 0.000 description 1
- PYFXOUCQTPUBOG-UHFFFAOYSA-N tert-butyl n-[1,3-dihydroxy-2-(hydroxymethyl)propan-2-yl]carbamate Chemical compound CC(C)(C)OC(=O)NC(CO)(CO)CO PYFXOUCQTPUBOG-UHFFFAOYSA-N 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 150000005622 tetraalkylammonium hydroxides Chemical class 0.000 description 1
- 125000005031 thiocyano group Chemical group S(C#N)* 0.000 description 1
- MAKDTFFYCIMFQP-UHFFFAOYSA-N titanium tungsten Chemical compound [Ti].[W] MAKDTFFYCIMFQP-UHFFFAOYSA-N 0.000 description 1
- LMYRWZFENFIFIT-UHFFFAOYSA-N toluene-4-sulfonamide Chemical compound CC1=CC=C(S(N)(=O)=O)C=C1 LMYRWZFENFIFIT-UHFFFAOYSA-N 0.000 description 1
- 125000002088 tosyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])S(*)(=O)=O 0.000 description 1
- 150000003918 triazines Chemical class 0.000 description 1
- TUODWSVQODNTSU-UHFFFAOYSA-M trifluoromethanesulfonate;tris[4-[(2-methylpropan-2-yl)oxy]phenyl]sulfanium Chemical compound [O-]S(=O)(=O)C(F)(F)F.C1=CC(OC(C)(C)C)=CC=C1[S+](C=1C=CC(OC(C)(C)C)=CC=1)C1=CC=C(OC(C)(C)C)C=C1 TUODWSVQODNTSU-UHFFFAOYSA-M 0.000 description 1
- FAYMLNNRGCYLSR-UHFFFAOYSA-M triphenylsulfonium triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F.C1=CC=CC=C1[S+](C=1C=CC=CC=1)C1=CC=CC=C1 FAYMLNNRGCYLSR-UHFFFAOYSA-M 0.000 description 1
- GPRLSGONYQIRFK-MNYXATJNSA-N triton Chemical compound [3H+] GPRLSGONYQIRFK-MNYXATJNSA-N 0.000 description 1
- 229920001567 vinyl ester resin Polymers 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 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
- 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
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F20/00—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride, ester, amide, imide or nitrile thereof
- C08F20/02—Monocarboxylic acids having less than ten carbon atoms, Derivatives thereof
- C08F20/10—Esters
- C08F20/34—Esters containing nitrogen, e.g. N,N-dimethylaminoethyl (meth)acrylate
- C08F20/36—Esters containing nitrogen, e.g. N,N-dimethylaminoethyl (meth)acrylate containing oxygen in addition to the carboxy oxygen, e.g. 2-N-morpholinoethyl (meth)acrylate or 2-isocyanatoethyl (meth)acrylate
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D133/00—Coating compositions based on homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Coating compositions based on derivatives of such polymers
- C09D133/04—Homopolymers or copolymers of esters
- C09D133/14—Homopolymers or copolymers of esters of esters containing halogen, nitrogen, sulfur or oxygen atoms in addition to the carboxy oxygen
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D163/00—Coating compositions based on epoxy resins; Coating compositions based on derivatives of epoxy resins
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D7/00—Features of coating compositions, not provided for in group C09D5/00; Processes for incorporating ingredients in coating compositions
- C09D7/40—Additives
- C09D7/65—Additives macromolecular
-
- 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
-
- 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
- G03F7/0752—Silicon-containing compounds in non photosensitive layers or as additives, e.g. for dry lithography
-
- 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
-
- 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
- H01L21/027—Making masks on semiconductor bodies for further photolithographic processing not provided for in group H01L21/18 or H01L21/34
- H01L21/033—Making masks on semiconductor bodies for further photolithographic processing not provided for in group H01L21/18 or H01L21/34 comprising inorganic layers
- H01L21/0332—Making masks on semiconductor bodies for further photolithographic processing not provided for in group H01L21/18 or H01L21/34 comprising inorganic layers characterised by their composition, e.g. multilayer masks, materials
Landscapes
- Engineering & Computer Science (AREA)
- Physics & Mathematics (AREA)
- General Physics & Mathematics (AREA)
- Chemical & Material Sciences (AREA)
- Architecture (AREA)
- Structural Engineering (AREA)
- Organic Chemistry (AREA)
- Wood Science & Technology (AREA)
- Materials Engineering (AREA)
- Life Sciences & Earth Sciences (AREA)
- Manufacturing & Machinery (AREA)
- Polymers & Plastics (AREA)
- Microelectronics & Electronic Packaging (AREA)
- Computer Hardware Design (AREA)
- Condensed Matter Physics & Semiconductors (AREA)
- Inorganic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Power Engineering (AREA)
- Materials For Photolithography (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Photosensitive Polymer And Photoresist Processing (AREA)
- Plural Heterocyclic Compounds (AREA)
- Application Of Or Painting With Fluid Materials (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Exposure Of Semiconductors, Excluding Electron Or Ion Beam Exposure (AREA)
Description
本明細書で用いる場合、コーティング組成物の「総固形分」は、溶剤担体を除いたコーティング組成物の全材料及び成分を意味する。
追加の繰り返し構造単位には、例えば、エッチ速度及び溶解性などの、フォトレジスト組成物の特性を調整する目的のための1つ以上の追加の単位が含まれ得る。例示的な追加の単位は、(メタ)アクリレート、ビニルエーテル、ビニルケトン及びビニルエステルの1つ以上を含み得る。ポリマー中に存在する場合、1種以上の追加の繰り返し単位は、典型的には、それぞれのポリマーの繰り返し単位の合計を基準として、最大99モル%、典型的には3~80モル%の量で使用される。
丸底フラスコに、TBPMA(15g)、V-65開始剤(1.73g)、及びテトラヒドロフラン(30g)を入れて溶液を形成し、これを窒素バブリングで15分間パージした。次いで、溶液を窒素雰囲気下、60℃で17時間加熱した。その後、溶液を室温まで放冷し、ポリマーA-1で表される生成物を500mLのヘプタンの中に析出させ、濾過により回収し、真空下50℃で17時間乾燥した。収量:12.5g。Mw(GPC):21.377g/mol、ポリスチレン標準。
丸底フラスコに、N-Boc-エタノールアミン(10g)、トリエチルアミン(7.58g)、及びテトラヒドロフラン(60mL)を入れて溶液を形成した。無水メタクリル酸(22.0g)を溶液に添加し、得られた混合物を室温で72時間撹拌した。次いで、酢酸エチル(300mL)を添加して反応混合物を希釈した。得られた有機溶液を飽和重炭酸ナトリウム(3×200mL)で洗浄し、有機層を分離し、溶剤をロータリーエバポレーターによって真空下で有機層から除去した。酢酸エチルから再結晶し、真空下で50℃で17時間乾燥することにより、モノマーB-1で表されるモノマー生成物を得た。収量:10.69g。
表1は、示されている量の成分を混合することによって調製した実施例1~8及び比較例1~3のコーティング組成物を示す。量は、ポリマー1と、ポリマー2と、添加剤と、溶剤とを含むコーティング組成物の総重量を基準とした重量パーセントである。
膜架橋の指標として溶剤剥離耐性を測定した。表1のコーティング組成物を0.2μmのポリテトラフルオロエチレンシリンジを通して濾過し、ACT-8 Clean Track(Tokyo Electron Co.)でそれぞれ200mmのベアシリコンウェハー上に1500rpmでスピンコートし、次いで215℃で60秒間硬化して、硬化したコーティング層を膜として形成した。初期の膜厚は、Therma-Wave OptiProbe(商標)計測ツールを使用して測定した。耐溶剤剥離性は、PGMEAリムーバーをそれぞれの膜に90秒間塗布した後、105℃で60秒間剥離後ベークすることによって決定した。それぞれの膜の厚さを再度測定し、PGMEAリムーバーの塗布によって失われた膜厚の量を決定した。表3は、PGMEAリムーバーとの接触前後の膜厚測定の結果を示しており、結果は、PGMEAリムーバーと接触した後にウェハー上に残っている膜厚のパーセント割合(%膜残存)として表されている。PGMEAリムーバーで処理した後に残っている膜の量は、硬化したコーティング層の架橋の程度の指標であった。
試験した配合物サンプルを、0.2μmのポリテトラフルオロエチレンシリンジを通して濾過し、ACT-8 Clean Track(Tokyo Electron Co.)を使用してそれぞれ200mmのベアシリコンウェハー上に1500rpmでスピンコートし、240℃で60秒間ベークした。各コーティングした膜のベーク後の膜厚を、Therma-wave Co.のOptiProbe(商標)装置で測定した。次いで、コーティングしたサンプルを、w/w/w比が1:1:5である30%NH4OH/30%H2O2/水の混合物を使用して、SC-1ウェット剥離性について評価した。その後SC-1混合物を70℃に加熱した。コーティングされた各ウェハーの試験片を剥離液に5分間浸漬した。試験片をSC-1混合物から取り出し、脱イオン水ですすぎ洗いした。各サンプルの膜品質は、目視検査によって決定した。
Claims (5)
- 基板上にコーティング組成物の層を塗布すること;
前記塗布されたコーティング組成物を硬化させて、コーティングされた下層を形成すること;及び
前記コーティングされた下層上にフォトレジスト層を形成すること;
を含むパターン形成方法であって、前記コーティング組成物が、
2つ以上のヒドロキシ基を含む第1の材料と;
2つ以上のグリシジル基を含む第2の材料と;
保護されたアミノ基を含む添加剤と;
溶剤と;
を含み、
前記添加剤が、式(4a)若しくは(4b):
R 6 、R 7 、及びR 8 は、それぞれ独立して、置換若しくは無置換C 1~20 アルキル、置換若しくは無置換C 3~20 シクロアルキル、置換若しくは無置換C 3~20 ヘテロシクロアルキル、置換若しくは無置換C 2~20 アルケニル、置換若しくは無置換C 3~20 シクロアルケニル、置換若しくは無置換C 3~20 ヘテロシクロアルケニル、置換若しくは無置換C 6~20 アリール、又は置換若しくは無置換C 4~20 ヘテロアリールであり;
任意選択的に、R 6 、R 7 、及びR 8 のうちの任意の2つ以上が一緒に環を形成しており;
Aは、単結合又は置換若しくは無置換C 1~2 アルキレンであり;
各R k は、独立して、ハロゲン、ヒドロキシ、カルボン酸、チオール、置換若しくは無置換C 1~30 アルキル、置換若しくは無置換C 1~30 ヘテロアルキル、置換若しくは無置換C 3~30 シクロアルキル、置換若しくは無置換C 2~30 ヘテロシクロアルキル、置換若しくは無置換C 2~30 アルケニル、置換若しくは無置換C 6~30 アリール、置換若しくは無置換C 7~30 アリールアルキル、置換若しくは無置換C 7~30 アルキルアリール、置換若しくは無置換C 1~30 ヘテロアリール、置換若しくは無置換C 2~30 ヘテロアリールアルキル、又は置換若しくは無置換C 2~30 アルキルヘテロアリールであり、R k は、任意選択的に、その構造の一部として-O-、-C(O)-、-NR k1 -、-S-、-S(O)-、又は-S(O) 2 -のうちの1つ以上を更に含み、R k1 は、置換若しくは無置換C 1~30 アルキル、置換若しくは無置換C 3~30 シクロアルキル、置換若しくは無置換C 1~20 ヘテロシクロアルキル、置換若しくは無置換C 6~30 アリール、置換若しくは無置換C 7~30 アリールアルキル、置換若しくは無置換C 7~30 アルキルアリール、置換若しくは無置換C 4~30 ヘテロアリール、置換若しくは無置換C 5~30 ヘテロアリールアルキル、又は置換若しくは無置換C 5~30 アルキルヘテロアリールであり;
nは0~11の整数であり;
R 9 及びR 10 は、それぞれ独立して、水素、置換若しくは無置換C 1~30 アルキル、置換若しくは無置換C 1~30 ヘテロアルキル、置換若しくは無置換C 3~30 シクロアルキル、置換若しくは無置換C 2~30 ヘテロシクロアルキル、置換若しくは無置換C 2~30 アルケニル、置換若しくは無置換C 6~30 アリール、置換若しくは無置換C 7~30 アリールアルキル、置換若しくは無置換C 7~30 アルキルアリール、置換若しくは無置換C 1~30 ヘテロアリール、置換若しくは無置換C 2~30 ヘテロアリールアルキル、又は置換若しくは無置換C 2~30 アルキルヘテロアリールである)
の化合物を含むか;又は式(5a)若しくは式(5b):
R a は、水素、フッ素、置換若しくは無置換C 1~5 アルキル、又は置換若しくは無置換C 1~5 フルオロアルキルであり;
L 1 は二価の連結基であり;
R 6 、R 7 、及びR 8 は、それぞれ独立して、置換若しくは無置換C 1~20 アルキル、置換若しくは無置換C 3~20 シクロアルキル、置換若しくは無置換C 3~20 ヘテロシクロアルキル、置換若しくは無置換C 2~20 アルケニル、置換若しくは無置換C 3~20 シクロアルケニル、置換若しくは無置換C 3~20 ヘテロシクロアルケニル、置換若しくは無置換C 6~20 アリール、又は置換若しくは無置換C 4~20 ヘテロアリールであり;
任意選択的に、R 6 、R 7 、及びR 8 のうちの任意の2つ以上は、二価の連結基を介して一緒に環を形成している)
R a は、水素、フッ素、置換若しくは無置換C 1~5 アルキル、又は置換若しくは無置換C 1~5 フルオロアルキルであり;
R 6 、R 7 、及びR 8 は、それぞれ独立して、置換若しくは無置換C 1~20 アルキル、置換若しくは無置換C 3~20 シクロアルキル、置換若しくは無置換C 3~20 ヘテロシクロアルキル、置換若しくは無置換C 2~20 アルケニル、置換若しくは無置換C 3~20 シクロアルケニル、置換若しくは無置換C 3~20 ヘテロシクロアルケニル、置換若しくは無置換C 6~20 アリール、又は置換若しくは無置換C 4~20 ヘテロアリールであり;
任意選択的に、R 6 、R 7 、及びR 8 のうちの任意の2つは、二価の連結基を介して一緒に環を形成しており;
Aは、単結合又は置換若しくは無置換C 1~2 アルキレンであり;
各R k は、独立して、ハロゲン、ヒドロキシ、カルボン酸、チオール、置換若しくは無置換C 1~30 アルキル、置換若しくは無置換C 1~30 ヘテロアルキル、置換若しくは無置換C 3~30 シクロアルキル、置換若しくは無置換C 2~30 ヘテロシクロアルキル、置換若しくは無置換C 2~30 アルケニル、置換若しくは無置換C 6~30 アリール、置換若しくは無置換C 7~30 アリールアルキル、置換若しくは無置換C 7~30 アルキルアリール、置換若しくは無置換C 1~30 ヘテロアリール、置換若しくは無置換C 2~30 ヘテロアリールアルキル、又は置換若しくは無置換C 2~30 アルキルヘテロアリールであり、R k は、-O-、-C(O)-、-NR k2 -、-S-、-S(O)-、又は-S(O) 2 -のうちの1つ以上を任意選択的に更に含み、R k2 は、置換若しくは無置換C 1~30 アルキル、置換若しくは無置換C 3~30 シクロアルキル、置換若しくは無置換C 1~20 ヘテロシクロアルキル、置換若しくは無置換C 6~30 アリール、置換若しくは無置換C 7~30 アリールアルキル、置換若しくは無置換C 7~30 アルキルアリール、置換若しくは無置換C 4~30 ヘテロアリール、置換若しくは無置換C 5~30 ヘテロアリールアルキル、又は置換若しくは無置換C 5~30 アルキルヘテロアリールであり;
nは、0~3の整数である)
のモノマーに由来する繰り返し単位を含むポリマーを含む、方法。 - 前記フォトレジスト層を形成する前に、前記コーティングされた下層の上にケイ素含有層、有機反射防止コーティング層、又はこれらの組み合わせを形成することを更に含む、請求項1に記載の方法。
- 前記フォトレジスト層にパターンを形成し、前記パターン形成されたフォトレジスト層から、前記コーティングされた下層及び前記コーティングされた下層の下の層にパターンを転写することを更に含む、請求項1に記載の方法。
- 露光されたフォトレジスト層を現像した後、且つ前記パターンを前記コーティングされた下層に転写する工程の前に、前記コーティングされた下層の上に配置されたケイ素含有層、有機反射防止コーティング層、又はこれらの組み合わせにパターンを転写することを更に含む、請求項2に記載の方法。
- 前記コーティング組成物が光酸発生剤を含まない、請求項1~4のいずれか一項に記載の方法。
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WO2016208300A1 (ja) | 2015-06-24 | 2016-12-29 | 富士フイルム株式会社 | パターン形成方法、積層体、及び、有機溶剤現像用レジスト組成物 |
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