TWI465421B - 光酸產生劑 - Google Patents
光酸產生劑 Download PDFInfo
- Publication number
- TWI465421B TWI465421B TW100143281A TW100143281A TWI465421B TW I465421 B TWI465421 B TW I465421B TW 100143281 A TW100143281 A TW 100143281A TW 100143281 A TW100143281 A TW 100143281A TW I465421 B TWI465421 B TW I465421B
- Authority
- TW
- Taiwan
- Prior art keywords
- entire entire
- photoresist
- aryl
- sulfonic acid
- group
- Prior art date
Links
- 229920002120 photoresistant polymer Polymers 0.000 claims description 73
- -1 aryl sulfonic acid Chemical compound 0.000 claims description 44
- 239000000203 mixture Substances 0.000 claims description 43
- 229920000642 polymer Polymers 0.000 claims description 39
- 125000003118 aryl group Chemical group 0.000 claims description 34
- 125000000524 functional group Chemical group 0.000 claims description 28
- 239000002253 acid Substances 0.000 claims description 20
- 230000005855 radiation Effects 0.000 claims description 20
- 125000000217 alkyl group Chemical group 0.000 claims description 18
- 238000000034 method Methods 0.000 claims description 18
- 150000001875 compounds Chemical class 0.000 claims description 17
- 239000000758 substrate Substances 0.000 claims description 17
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims description 16
- 150000001450 anions Chemical class 0.000 claims description 15
- 230000015572 biosynthetic process Effects 0.000 claims description 15
- 229910052717 sulfur Inorganic materials 0.000 claims description 11
- 239000000178 monomer Substances 0.000 claims description 10
- 229910052740 iodine Inorganic materials 0.000 claims description 8
- 150000001335 aliphatic alkanes Chemical class 0.000 claims description 7
- JHRWWRDRBPCWTF-OLQVQODUSA-N captafol Chemical compound C1C=CC[C@H]2C(=O)N(SC(Cl)(Cl)C(Cl)Cl)C(=O)[C@H]21 JHRWWRDRBPCWTF-OLQVQODUSA-N 0.000 claims description 7
- 229910052799 carbon Inorganic materials 0.000 claims description 7
- 229910052739 hydrogen Inorganic materials 0.000 claims description 7
- 125000002877 alkyl aryl group Chemical group 0.000 claims description 6
- 229910052731 fluorine Inorganic materials 0.000 claims description 6
- 230000003213 activating effect Effects 0.000 claims description 5
- 125000002733 (C1-C6) fluoroalkyl group Chemical group 0.000 claims description 4
- 229940124530 sulfonamide Drugs 0.000 claims description 3
- 150000003456 sulfonamides Chemical class 0.000 claims description 3
- 238000000059 patterning Methods 0.000 claims description 2
- 238000006116 polymerization reaction Methods 0.000 claims 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 45
- XEKOWRVHYACXOJ-UHFFFAOYSA-N ethyl acetate Substances CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 28
- 239000010410 layer Substances 0.000 description 28
- 239000000243 solution Substances 0.000 description 22
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 20
- 238000005481 NMR spectroscopy Methods 0.000 description 18
- LZCLXQDLBQLTDK-UHFFFAOYSA-N ethyl 2-hydroxypropanoate Chemical compound CCOC(=O)C(C)O LZCLXQDLBQLTDK-UHFFFAOYSA-N 0.000 description 18
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 18
- 239000002904 solvent Substances 0.000 description 15
- 238000003786 synthesis reaction Methods 0.000 description 14
- 239000002585 base Substances 0.000 description 13
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- 238000000354 decomposition reaction Methods 0.000 description 12
- 235000019439 ethyl acetate Nutrition 0.000 description 12
- 239000007787 solid Substances 0.000 description 12
- 239000012953 triphenylsulfonium Substances 0.000 description 12
- 230000035945 sensitivity Effects 0.000 description 11
- 150000001768 cations Chemical class 0.000 description 10
- 239000000047 product Substances 0.000 description 10
- 239000004094 surface-active agent Substances 0.000 description 10
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
- 229940116333 ethyl lactate Drugs 0.000 description 9
- 239000002243 precursor Substances 0.000 description 9
- 235000012431 wafers Nutrition 0.000 description 9
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 8
- 230000000052 comparative effect Effects 0.000 description 8
- 239000011541 reaction mixture Substances 0.000 description 8
- 239000011877 solvent mixture Substances 0.000 description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
- 239000000654 additive Substances 0.000 description 7
- 125000003545 alkoxy group Chemical group 0.000 description 7
- 239000003795 chemical substances by application Substances 0.000 description 7
- 238000009472 formulation Methods 0.000 description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- CSCPPACGZOOCGX-WFGJKAKNSA-N acetone d6 Chemical compound [2H]C([2H])([2H])C(=O)C([2H])([2H])[2H] CSCPPACGZOOCGX-WFGJKAKNSA-N 0.000 description 6
- 150000001412 amines Chemical class 0.000 description 6
- 238000001816 cooling Methods 0.000 description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 6
- 238000002360 preparation method Methods 0.000 description 6
- 230000008569 process Effects 0.000 description 6
- 150000003839 salts Chemical group 0.000 description 6
- 239000011734 sodium Substances 0.000 description 6
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 5
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 5
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
- 238000004440 column chromatography Methods 0.000 description 5
- 150000002148 esters Chemical class 0.000 description 5
- YEJRWHAVMIAJKC-UHFFFAOYSA-N gamma-butyrolactone Natural products O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 description 5
- 229910052732 germanium Inorganic materials 0.000 description 5
- GNPVGFCGXDBREM-UHFFFAOYSA-N germanium atom Chemical group [Ge] GNPVGFCGXDBREM-UHFFFAOYSA-N 0.000 description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 5
- MGFYSGNNHQQTJW-UHFFFAOYSA-N iodonium Chemical compound [IH2+] MGFYSGNNHQQTJW-UHFFFAOYSA-N 0.000 description 5
- 230000003287 optical effect Effects 0.000 description 5
- 239000012044 organic layer Substances 0.000 description 5
- LLHKCFNBLRBOGN-UHFFFAOYSA-N propylene glycol methyl ether acetate Chemical compound COCC(C)OC(C)=O LLHKCFNBLRBOGN-UHFFFAOYSA-N 0.000 description 5
- WLOQLWBIJZDHET-UHFFFAOYSA-N triphenylsulfonium Chemical compound C1=CC=CC=C1[S+](C=1C=CC=CC=1)C1=CC=CC=C1 WLOQLWBIJZDHET-UHFFFAOYSA-N 0.000 description 5
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 4
- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- 239000003513 alkali Substances 0.000 description 4
- 150000007942 carboxylates Chemical class 0.000 description 4
- 238000009833 condensation Methods 0.000 description 4
- 230000005494 condensation Effects 0.000 description 4
- 125000000753 cycloalkyl group Chemical group 0.000 description 4
- 125000004428 fluoroalkoxy group Chemical group 0.000 description 4
- 125000003709 fluoroalkyl group Chemical group 0.000 description 4
- 125000003367 polycyclic group Chemical group 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- 238000002390 rotary evaporation Methods 0.000 description 4
- 239000007858 starting material Substances 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- VDZOOKBUILJEDG-UHFFFAOYSA-M tetrabutylammonium hydroxide Chemical compound [OH-].CCCC[N+](CCCC)(CCCC)CCCC VDZOOKBUILJEDG-UHFFFAOYSA-M 0.000 description 4
- WGTYBPLFGIVFAS-UHFFFAOYSA-M tetramethylammonium hydroxide Chemical compound [OH-].C[N+](C)(C)C WGTYBPLFGIVFAS-UHFFFAOYSA-M 0.000 description 4
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 4
- KJCFBSDAZAITOD-UHFFFAOYSA-N 1-[2-(2-methoxyethoxy)ethoxy]-4-[4-[2-(2-methoxyethoxy)ethoxy]phenyl]sulfinylbenzene Chemical compound C1=CC(OCCOCCOC)=CC=C1S(=O)C1=CC=C(OCCOCCOC)C=C1 KJCFBSDAZAITOD-UHFFFAOYSA-N 0.000 description 3
- NXYICUMSYKIABQ-UHFFFAOYSA-N 1-iodo-4-phenylbenzene Chemical group C1=CC(I)=CC=C1C1=CC=CC=C1 NXYICUMSYKIABQ-UHFFFAOYSA-N 0.000 description 3
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical class S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 3
- 235000019502 Orange oil Nutrition 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 229960000583 acetic acid Drugs 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 229910052794 bromium Inorganic materials 0.000 description 3
- 239000003153 chemical reaction reagent Substances 0.000 description 3
- 239000011248 coating agent Substances 0.000 description 3
- 238000000576 coating method Methods 0.000 description 3
- 239000012043 crude product Substances 0.000 description 3
- 238000011161 development Methods 0.000 description 3
- 229910052736 halogen Inorganic materials 0.000 description 3
- 150000002367 halogens Chemical class 0.000 description 3
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical class I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 3
- 150000002466 imines Chemical class 0.000 description 3
- 238000001459 lithography Methods 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- 125000002950 monocyclic group Chemical group 0.000 description 3
- 239000010502 orange oil Substances 0.000 description 3
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 3
- 238000001556 precipitation Methods 0.000 description 3
- 238000010791 quenching Methods 0.000 description 3
- 230000000171 quenching effect Effects 0.000 description 3
- 125000001424 substituent group Chemical group 0.000 description 3
- RWSOTUBLDIXVET-UHFFFAOYSA-O sulfonium Chemical class [SH3+] RWSOTUBLDIXVET-UHFFFAOYSA-O 0.000 description 3
- FMEBJQQRPGHVOR-UHFFFAOYSA-N (1-ethylcyclopentyl) 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OC1(CC)CCCC1 FMEBJQQRPGHVOR-UHFFFAOYSA-N 0.000 description 2
- ZMAOPHHNBQIJOQ-UHFFFAOYSA-N (2-propan-2-yl-2-adamantyl) 2-methylprop-2-enoate Chemical compound C1C(C2)CC3CC1C(C(C)C)(OC(=O)C(C)=C)C2C3 ZMAOPHHNBQIJOQ-UHFFFAOYSA-N 0.000 description 2
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 description 2
- 125000006651 (C3-C20) cycloalkyl group Chemical group 0.000 description 2
- BYEAHWXPCBROCE-UHFFFAOYSA-N 1,1,1,3,3,3-hexafluoropropan-2-ol Chemical group FC(F)(F)C(O)C(F)(F)F BYEAHWXPCBROCE-UHFFFAOYSA-N 0.000 description 2
- VZXTWGWHSMCWGA-UHFFFAOYSA-N 1,3,5-triazine-2,4-diamine Chemical compound NC1=NC=NC(N)=N1 VZXTWGWHSMCWGA-UHFFFAOYSA-N 0.000 description 2
- HUXJXNSHCKHFIL-UHFFFAOYSA-N 1-(2-bromoethoxy)-2-methoxyethane Chemical compound COCCOCCBr HUXJXNSHCKHFIL-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
- NXXYKOUNUYWIHA-UHFFFAOYSA-N 2,6-Dimethylphenol Chemical compound CC1=CC=CC(C)=C1O NXXYKOUNUYWIHA-UHFFFAOYSA-N 0.000 description 2
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 2
- UEISEUSZLOAHHL-UHFFFAOYSA-N 2-(2-methoxyethoxy)ethoxybenzene Chemical compound COCCOCCOC1=CC=CC=C1 UEISEUSZLOAHHL-UHFFFAOYSA-N 0.000 description 2
- AFABGHUZZDYHJO-UHFFFAOYSA-N 2-Methylpentane Chemical compound CCCC(C)C AFABGHUZZDYHJO-UHFFFAOYSA-N 0.000 description 2
- DUZUYBOBIMKSPF-UHFFFAOYSA-N 2-naphthalen-2-ylsulfanylnaphthalene Chemical compound C1=CC=CC2=CC(SC=3C=C4C=CC=CC4=CC=3)=CC=C21 DUZUYBOBIMKSPF-UHFFFAOYSA-N 0.000 description 2
- JWAZRIHNYRIHIV-UHFFFAOYSA-N 2-naphthol Chemical compound C1=CC=CC2=CC(O)=CC=C21 JWAZRIHNYRIHIV-UHFFFAOYSA-N 0.000 description 2
- WADSJYLPJPTMLN-UHFFFAOYSA-N 3-(cycloundecen-1-yl)-1,2-diazacycloundec-2-ene Chemical compound C1CCCCCCCCC=C1C1=NNCCCCCCCC1 WADSJYLPJPTMLN-UHFFFAOYSA-N 0.000 description 2
- VWGKEVWFBOUAND-UHFFFAOYSA-N 4,4'-thiodiphenol Chemical compound C1=CC(O)=CC=C1SC1=CC=C(O)C=C1 VWGKEVWFBOUAND-UHFFFAOYSA-N 0.000 description 2
- RQCACQIALULDSK-UHFFFAOYSA-N 4-(4-hydroxyphenyl)sulfinylphenol Chemical compound C1=CC(O)=CC=C1S(=O)C1=CC=C(O)C=C1 RQCACQIALULDSK-UHFFFAOYSA-N 0.000 description 2
- FUGYGGDSWSUORM-UHFFFAOYSA-N 4-hydroxystyrene Chemical compound OC1=CC=C(C=C)C=C1 FUGYGGDSWSUORM-UHFFFAOYSA-N 0.000 description 2
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- 239000007877 V-601 Substances 0.000 description 2
- 235000011054 acetic acid Nutrition 0.000 description 2
- 230000004913 activation Effects 0.000 description 2
- 239000000956 alloy Substances 0.000 description 2
- 229910045601 alloy Inorganic materials 0.000 description 2
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 2
- 150000008064 anhydrides Chemical class 0.000 description 2
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 2
- 150000001503 aryl iodides Chemical class 0.000 description 2
- 125000004104 aryloxy group Chemical group 0.000 description 2
- 125000004429 atom Chemical group 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- ISAOCJYIOMOJEB-UHFFFAOYSA-N benzoin Chemical compound C=1C=CC=CC=1C(O)C(=O)C1=CC=CC=C1 ISAOCJYIOMOJEB-UHFFFAOYSA-N 0.000 description 2
- 239000004305 biphenyl Substances 0.000 description 2
- 125000006267 biphenyl group Chemical class 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- DKPFZGUDAPQIHT-UHFFFAOYSA-N butyl acetate Chemical compound CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- YEOCHZFPBYUXMC-UHFFFAOYSA-L copper benzoate Chemical compound [Cu+2].[O-]C(=O)C1=CC=CC=C1.[O-]C(=O)C1=CC=CC=C1 YEOCHZFPBYUXMC-UHFFFAOYSA-L 0.000 description 2
- 238000004132 cross linking Methods 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- 239000007857 degradation product Substances 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
- LTYMSROWYAPPGB-UHFFFAOYSA-N diphenyl sulfide Chemical compound C=1C=CC=CC=1SC1=CC=CC=C1 LTYMSROWYAPPGB-UHFFFAOYSA-N 0.000 description 2
- 239000012776 electronic material Substances 0.000 description 2
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 2
- OJCSPXHYDFONPU-UHFFFAOYSA-N etoac etoac Chemical compound CCOC(C)=O.CCOC(C)=O OJCSPXHYDFONPU-UHFFFAOYSA-N 0.000 description 2
- 238000001900 extreme ultraviolet lithography Methods 0.000 description 2
- 238000004868 gas analysis Methods 0.000 description 2
- YBMRDBCBODYGJE-UHFFFAOYSA-N germanium dioxide Chemical compound O=[Ge]=O YBMRDBCBODYGJE-UHFFFAOYSA-N 0.000 description 2
- CATSNJVOTSVZJV-UHFFFAOYSA-N heptan-2-one Chemical compound CCCCCC(C)=O CATSNJVOTSVZJV-UHFFFAOYSA-N 0.000 description 2
- 125000005842 heteroatom Chemical group 0.000 description 2
- ZQBFAOFFOQMSGJ-UHFFFAOYSA-N hexafluorobenzene Chemical compound FC1=C(F)C(F)=C(F)C(F)=C1F ZQBFAOFFOQMSGJ-UHFFFAOYSA-N 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 238000005649 metathesis reaction Methods 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 2
- 125000001624 naphthyl group Chemical group 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N o-biphenylenemethane Natural products C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 description 2
- 238000010943 off-gassing Methods 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- JGTNAGYHADQMCM-UHFFFAOYSA-N perfluorobutanesulfonic acid Chemical compound OS(=O)(=O)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F JGTNAGYHADQMCM-UHFFFAOYSA-N 0.000 description 2
- 125000005592 polycycloalkyl group Polymers 0.000 description 2
- 229910000027 potassium carbonate Inorganic materials 0.000 description 2
- LVTHXRLARFLXNR-UHFFFAOYSA-M potassium;1,1,2,2,3,3,4,4,4-nonafluorobutane-1-sulfonate Chemical compound [K+].[O-]S(=O)(=O)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F LVTHXRLARFLXNR-UHFFFAOYSA-M 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 2
- 239000000523 sample Substances 0.000 description 2
- 238000004528 spin coating Methods 0.000 description 2
- 239000012258 stirred mixture Substances 0.000 description 2
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 229910052715 tantalum Inorganic materials 0.000 description 2
- GUVRBAGPIYLISA-UHFFFAOYSA-N tantalum atom Chemical compound [Ta] GUVRBAGPIYLISA-UHFFFAOYSA-N 0.000 description 2
- 150000003568 thioethers Chemical class 0.000 description 2
- 150000003573 thiols Chemical class 0.000 description 2
- WJKHJLXJJJATHN-UHFFFAOYSA-N triflic anhydride Chemical compound FC(F)(F)S(=O)(=O)OS(=O)(=O)C(F)(F)F WJKHJLXJJJATHN-UHFFFAOYSA-N 0.000 description 2
- 238000013022 venting Methods 0.000 description 2
- 229920002554 vinyl polymer Polymers 0.000 description 2
- SWHAGWLVMRLFKO-UHFFFAOYSA-N (2-nitrophenyl)methyl carbamate Chemical group NC(=O)OCC1=CC=CC=C1[N+]([O-])=O SWHAGWLVMRLFKO-UHFFFAOYSA-N 0.000 description 1
- MSLTZKLJPHUCPU-WNQIDUERSA-M (2s)-2-hydroxypropanoate;tetrabutylazanium Chemical compound C[C@H](O)C([O-])=O.CCCC[N+](CCCC)(CCCC)CCCC MSLTZKLJPHUCPU-WNQIDUERSA-M 0.000 description 1
- OOIBFPKQHULHSQ-UHFFFAOYSA-N (3-hydroxy-1-adamantyl) 2-methylprop-2-enoate Chemical compound C1C(C2)CC3CC2(O)CC1(OC(=O)C(=C)C)C3 OOIBFPKQHULHSQ-UHFFFAOYSA-N 0.000 description 1
- 125000000027 (C1-C10) alkoxy group Chemical group 0.000 description 1
- 125000003837 (C1-C20) alkyl group Chemical group 0.000 description 1
- 125000000923 (C1-C30) alkyl group Chemical group 0.000 description 1
- JGTNAGYHADQMCM-UHFFFAOYSA-M 1,1,2,2,3,3,4,4,4-nonafluorobutane-1-sulfonate Chemical compound [O-]S(=O)(=O)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F JGTNAGYHADQMCM-UHFFFAOYSA-M 0.000 description 1
- NXORKRYQKIPTCP-UHFFFAOYSA-M 1,1,2,2,3,3,4,4,4-nonafluorobutane-1-sulfonate;(4-phenoxyphenyl)-(4-phenylphenyl)iodanium Chemical compound [O-]S(=O)(=O)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F.C=1C=C([I+]C=2C=CC(=CC=2)C=2C=CC=CC=2)C=CC=1OC1=CC=CC=C1 NXORKRYQKIPTCP-UHFFFAOYSA-M 0.000 description 1
- VLLPVDKADBYKLM-UHFFFAOYSA-M 1,1,2,2,3,3,4,4,4-nonafluorobutane-1-sulfonate;triphenylsulfanium Chemical compound [O-]S(=O)(=O)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F.C1=CC=CC=C1[S+](C=1C=CC=CC=1)C1=CC=CC=C1 VLLPVDKADBYKLM-UHFFFAOYSA-M 0.000 description 1
- DIIIISSCIXVANO-UHFFFAOYSA-N 1,2-Dimethylhydrazine Chemical compound CNNC DIIIISSCIXVANO-UHFFFAOYSA-N 0.000 description 1
- YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 description 1
- 125000001989 1,3-phenylene group Chemical group [H]C1=C([H])C([*:1])=C([H])C([*:2])=C1[H] 0.000 description 1
- JOLQKTGDSGKSKJ-UHFFFAOYSA-N 1-ethoxypropan-2-ol Chemical compound CCOCC(C)O JOLQKTGDSGKSKJ-UHFFFAOYSA-N 0.000 description 1
- QLAWAFBTLLCIIM-UHFFFAOYSA-N 1-naphthalen-1-ylsulfanylnaphthalene Chemical compound C1=CC=C2C(SC=3C4=CC=CC=C4C=CC=3)=CC=CC2=C1 QLAWAFBTLLCIIM-UHFFFAOYSA-N 0.000 description 1
- QMBSJPZHUJCMJU-UHFFFAOYSA-N 2-(2-ethoxyethoxy)propanoic acid Chemical compound CCOCCOC(C)C(O)=O QMBSJPZHUJCMJU-UHFFFAOYSA-N 0.000 description 1
- JIXHYWCLUOGIMM-UHFFFAOYSA-N 2-(2-methoxyethoxy)propanoic acid Chemical compound COCCOC(C)C(O)=O JIXHYWCLUOGIMM-UHFFFAOYSA-N 0.000 description 1
- RFCQDOVPMUSZMN-UHFFFAOYSA-N 2-Naphthalenethiol Chemical compound C1=CC=CC2=CC(S)=CC=C21 RFCQDOVPMUSZMN-UHFFFAOYSA-N 0.000 description 1
- ZBOUBGLJEWWLPX-UHFFFAOYSA-N 2-naphthalen-2-ylbenzenethiol Chemical compound SC1=CC=CC=C1C1=CC=C(C=CC=C2)C2=C1 ZBOUBGLJEWWLPX-UHFFFAOYSA-N 0.000 description 1
- 125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 description 1
- QDFXRVAOBHEBGJ-UHFFFAOYSA-N 3-(cyclononen-1-yl)-4,5,6,7,8,9-hexahydro-1h-diazonine Chemical compound C1CCCCCCC=C1C1=NNCCCCCC1 QDFXRVAOBHEBGJ-UHFFFAOYSA-N 0.000 description 1
- AYKYXWQEBUNJCN-UHFFFAOYSA-N 3-methylfuran-2,5-dione Chemical compound CC1=CC(=O)OC1=O AYKYXWQEBUNJCN-UHFFFAOYSA-N 0.000 description 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- WPNYPUJKSMPYFK-UHFFFAOYSA-N 9-naphthalen-2-ylsulfanyl-9h-fluorene Chemical compound C1=CC=CC2=CC(SC3C4=CC=CC=C4C4=CC=CC=C43)=CC=C21 WPNYPUJKSMPYFK-UHFFFAOYSA-N 0.000 description 1
- 241000208340 Araliaceae Species 0.000 description 1
- JBRZTFJDHDCESZ-UHFFFAOYSA-N AsGa Chemical compound [As]#[Ga] JBRZTFJDHDCESZ-UHFFFAOYSA-N 0.000 description 1
- 239000005711 Benzoic acid Substances 0.000 description 1
- 150000000703 Cerium Chemical class 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- MHZGKXUYDGKKIU-UHFFFAOYSA-N Decylamine Chemical compound CCCCCCCCCCN MHZGKXUYDGKKIU-UHFFFAOYSA-N 0.000 description 1
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
- BWGNESOTFCXPMA-UHFFFAOYSA-N Dihydrogen disulfide Chemical compound SS BWGNESOTFCXPMA-UHFFFAOYSA-N 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- 229910001218 Gallium arsenide Inorganic materials 0.000 description 1
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical group CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 description 1
- 239000002841 Lewis acid Substances 0.000 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 1
- KWYHDKDOAIKMQN-UHFFFAOYSA-N N,N,N',N'-tetramethylethylenediamine Chemical compound CN(C)CCN(C)C KWYHDKDOAIKMQN-UHFFFAOYSA-N 0.000 description 1
- 235000005035 Panax pseudoginseng ssp. pseudoginseng Nutrition 0.000 description 1
- 235000003140 Panax quinquefolius Nutrition 0.000 description 1
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 1
- DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 description 1
- 244000028419 Styrax benzoin Species 0.000 description 1
- 235000000126 Styrax benzoin Nutrition 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 235000008411 Sumatra benzointree Nutrition 0.000 description 1
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 1
- NRTOMJZYCJJWKI-UHFFFAOYSA-N Titanium nitride Chemical compound [Ti]#N NRTOMJZYCJJWKI-UHFFFAOYSA-N 0.000 description 1
- ICURIFUTRQEJPA-UHFFFAOYSA-N [3,5-bis(1,1,1,3,3,3-hexafluoro-2-hydroxypropan-2-yl)cyclohexyl] 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OC1CC(C(O)(C(F)(F)F)C(F)(F)F)CC(C(O)(C(F)(F)F)C(F)(F)F)C1 ICURIFUTRQEJPA-UHFFFAOYSA-N 0.000 description 1
- LRIUKPUCKCECPT-UHFFFAOYSA-N [hydroxy(phenyl)-$l^{3}-iodanyl] 4-methylbenzenesulfonate Chemical compound C1=CC(C)=CC=C1S(=O)(=O)OI(O)C1=CC=CC=C1 LRIUKPUCKCECPT-UHFFFAOYSA-N 0.000 description 1
- 238000002835 absorbance Methods 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 150000004703 alkoxides Chemical class 0.000 description 1
- 125000005210 alkyl ammonium group Chemical group 0.000 description 1
- 125000005248 alkyl aryloxy group Chemical group 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 230000003321 amplification Effects 0.000 description 1
- 238000005349 anion exchange Methods 0.000 description 1
- 125000002178 anthracenyl group Chemical group C1(=CC=CC2=CC3=CC=CC=C3C=C12)* 0.000 description 1
- 239000006117 anti-reflective coating Substances 0.000 description 1
- 125000005418 aryl aryl group Chemical group 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- 230000004888 barrier function Effects 0.000 description 1
- 150000001555 benzenes Chemical group 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- 229960002130 benzoin Drugs 0.000 description 1
- 229950011260 betanaphthol Drugs 0.000 description 1
- 239000012455 biphasic mixture Substances 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 125000000319 biphenyl-4-yl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 description 1
- XOYZYOURGXJJOC-UHFFFAOYSA-N bis(2-tert-butylphenyl)iodanium Chemical compound CC(C)(C)C1=CC=CC=C1[I+]C1=CC=CC=C1C(C)(C)C XOYZYOURGXJJOC-UHFFFAOYSA-N 0.000 description 1
- DJBAOXYQCAKLPH-UHFFFAOYSA-M bis(4-tert-butylphenyl)iodanium;1,1,2,2,3,3,4,4,4-nonafluorobutane-1-sulfonate Chemical compound [O-]S(=O)(=O)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F.C1=CC(C(C)(C)C)=CC=C1[I+]C1=CC=C(C(C)(C)C)C=C1 DJBAOXYQCAKLPH-UHFFFAOYSA-M 0.000 description 1
- 229910052797 bismuth Inorganic materials 0.000 description 1
- JCXGWMGPZLAOME-UHFFFAOYSA-N bismuth atom Chemical compound [Bi] JCXGWMGPZLAOME-UHFFFAOYSA-N 0.000 description 1
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- CETPSERCERDGAM-UHFFFAOYSA-N ceric oxide Chemical compound O=[Ce]=O CETPSERCERDGAM-UHFFFAOYSA-N 0.000 description 1
- 229910000422 cerium(IV) oxide Inorganic materials 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 238000006482 condensation reaction Methods 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 238000011109 contamination Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 239000010779 crude oil Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 150000001925 cycloalkenes Chemical class 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- 238000010511 deprotection reaction Methods 0.000 description 1
- 238000009792 diffusion process Methods 0.000 description 1
- 238000003618 dip coating Methods 0.000 description 1
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- XHQZXHMRBXBPEL-UHFFFAOYSA-N eaton reagent Chemical compound CS(O)(=O)=O.O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 XHQZXHMRBXBPEL-UHFFFAOYSA-N 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000000295 emission spectrum Methods 0.000 description 1
- 125000001033 ether group Chemical group 0.000 description 1
- FPIQZBQZKBKLEI-UHFFFAOYSA-N ethyl 1-[[2-chloroethyl(nitroso)carbamoyl]amino]cyclohexane-1-carboxylate Chemical compound ClCCN(N=O)C(=O)NC1(C(=O)OCC)CCCCC1 FPIQZBQZKBKLEI-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 150000002220 fluorenes Chemical class 0.000 description 1
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 125000004407 fluoroaryl group Chemical group 0.000 description 1
- 125000005348 fluorocycloalkyl group Chemical group 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 229940119177 germanium dioxide Drugs 0.000 description 1
- 235000008434 ginseng Nutrition 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 235000019382 gum benzoic Nutrition 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- DALYXJVFSIYXMA-UHFFFAOYSA-N hydrogen sulfide dimer Chemical compound S.S DALYXJVFSIYXMA-UHFFFAOYSA-N 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 150000004679 hydroxides Chemical class 0.000 description 1
- 238000003384 imaging method Methods 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 229940030980 inova Drugs 0.000 description 1
- 239000012212 insulator Substances 0.000 description 1
- 230000010354 integration Effects 0.000 description 1
- ICIWUVCWSCSTAQ-UHFFFAOYSA-M iodate Chemical compound [O-]I(=O)=O ICIWUVCWSCSTAQ-UHFFFAOYSA-M 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 150000002596 lactones Chemical group 0.000 description 1
- 150000007517 lewis acids Chemical class 0.000 description 1
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- 229910021645 metal ion Inorganic materials 0.000 description 1
- 125000005395 methacrylic acid group Chemical group 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- GBMDVOWEEQVZKZ-UHFFFAOYSA-N methanol;hydrate Chemical compound O.OC GBMDVOWEEQVZKZ-UHFFFAOYSA-N 0.000 description 1
- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 1
- 238000004377 microelectronic Methods 0.000 description 1
- 229910052758 niobium Inorganic materials 0.000 description 1
- 239000010955 niobium Substances 0.000 description 1
- GUCVJGMIXFAOAE-UHFFFAOYSA-N niobium atom Chemical compound [Nb] GUCVJGMIXFAOAE-UHFFFAOYSA-N 0.000 description 1
- 125000002560 nitrile group Chemical group 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- JFNLZVQOOSMTJK-KNVOCYPGSA-N norbornene Chemical compound C1[C@@H]2CC[C@H]1C=C2 JFNLZVQOOSMTJK-KNVOCYPGSA-N 0.000 description 1
- 150000002848 norbornenes Chemical class 0.000 description 1
- 238000003199 nucleic acid amplification method Methods 0.000 description 1
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
- 230000005693 optoelectronics Effects 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 1
- 125000005561 phenanthryl group Chemical group 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
- XYFCBTPGUUZFHI-UHFFFAOYSA-O phosphonium Chemical compound [PH4+] XYFCBTPGUUZFHI-UHFFFAOYSA-O 0.000 description 1
- 238000000206 photolithography Methods 0.000 description 1
- JLKDVMWYMMLWTI-UHFFFAOYSA-M potassium iodate Chemical compound [K+].[O-]I(=O)=O JLKDVMWYMMLWTI-UHFFFAOYSA-M 0.000 description 1
- 239000001230 potassium iodate Substances 0.000 description 1
- 235000006666 potassium iodate Nutrition 0.000 description 1
- 229940093930 potassium iodate Drugs 0.000 description 1
- OVQAQBXRJOPVEV-UHFFFAOYSA-M potassium;1-fluorobutane-1-sulfonate Chemical compound [K+].CCCC(F)S([O-])(=O)=O OVQAQBXRJOPVEV-UHFFFAOYSA-M 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- 229940090181 propyl acetate Drugs 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 239000013557 residual solvent Substances 0.000 description 1
- 229960004889 salicylic acid Drugs 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000004065 semiconductor Substances 0.000 description 1
- 150000003384 small molecules Chemical class 0.000 description 1
- 229940079827 sodium hydrogen sulfite Drugs 0.000 description 1
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 description 1
- 229960001922 sodium perborate Drugs 0.000 description 1
- 239000012418 sodium perborate tetrahydrate Substances 0.000 description 1
- IBDSNZLUHYKHQP-UHFFFAOYSA-N sodium;3-oxidodioxaborirane;tetrahydrate Chemical compound O.O.O.O.[Na+].[O-]B1OO1 IBDSNZLUHYKHQP-UHFFFAOYSA-N 0.000 description 1
- YKLJGMBLPUQQOI-UHFFFAOYSA-M sodium;oxidooxy(oxo)borane Chemical compound [Na+].[O-]OB=O YKLJGMBLPUQQOI-UHFFFAOYSA-M 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 description 1
- 125000005555 sulfoximide group Chemical group 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- MZLGASXMSKOWSE-UHFFFAOYSA-N tantalum nitride Chemical compound [Ta]#N MZLGASXMSKOWSE-UHFFFAOYSA-N 0.000 description 1
- 238000010345 tape casting Methods 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 150000005622 tetraalkylammonium hydroxides Chemical class 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 125000003258 trimethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])[*:1] 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
- SXPSZIHEWFTLEQ-UHFFFAOYSA-N tröger's base Chemical compound C12=CC=C(C)C=C2CN2C3=CC=C(C)C=C3CN1C2 SXPSZIHEWFTLEQ-UHFFFAOYSA-N 0.000 description 1
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 description 1
- 229910052721 tungsten Inorganic materials 0.000 description 1
- 239000010937 tungsten Substances 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F11/00—Compounds containing elements of Groups 6 or 16 of the Periodic Table
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C381/00—Compounds containing carbon and sulfur and having functional groups not covered by groups C07C301/00 - C07C337/00
- C07C381/12—Sulfonium compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F13/00—Compounds containing elements of Groups 7 or 17 of the Periodic Table
-
- 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
-
- 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
- G03F7/0045—Photosensitive materials with organic non-macromolecular light-sensitive compounds not otherwise provided for, e.g. dissolution inhibitors
-
- 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
- G03F7/0046—Photosensitive materials with perfluoro compounds, 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
- G03F7/039—Macromolecular compounds which are photodegradable, e.g. positive electron resists
- G03F7/0392—Macromolecular compounds which are photodegradable, e.g. positive electron resists the macromolecular compound being present in a chemically amplified positive photoresist composition
- G03F7/0397—Macromolecular compounds which are photodegradable, e.g. positive electron resists the macromolecular compound being present in a chemically amplified positive photoresist composition the macromolecular compound having an alicyclic moiety in a side chain
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/26—Processing photosensitive materials; Apparatus therefor
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S430/00—Radiation imagery chemistry: process, composition, or product thereof
- Y10S430/1053—Imaging affecting physical property or radiation sensitive material, or producing nonplanar or printing surface - process, composition, or product: radiation sensitive composition or product or process of making binder containing
- Y10S430/1055—Radiation sensitive composition or product or process of making
- Y10S430/106—Binder containing
- Y10S430/111—Polymer of unsaturated acid or ester
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S430/00—Radiation imagery chemistry: process, composition, or product thereof
- Y10S430/1053—Imaging affecting physical property or radiation sensitive material, or producing nonplanar or printing surface - process, composition, or product: radiation sensitive composition or product or process of making binder containing
- Y10S430/1055—Radiation sensitive composition or product or process of making
- Y10S430/114—Initiator containing
- Y10S430/12—Nitrogen compound containing
- Y10S430/121—Nitrogen in heterocyclic ring
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S430/00—Radiation imagery chemistry: process, composition, or product thereof
- Y10S430/1053—Imaging affecting physical property or radiation sensitive material, or producing nonplanar or printing surface - process, composition, or product: radiation sensitive composition or product or process of making binder containing
- Y10S430/1055—Radiation sensitive composition or product or process of making
- Y10S430/114—Initiator containing
- Y10S430/122—Sulfur compound containing
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S430/00—Radiation imagery chemistry: process, composition, or product thereof
- Y10S430/1053—Imaging affecting physical property or radiation sensitive material, or producing nonplanar or printing surface - process, composition, or product: radiation sensitive composition or product or process of making binder containing
- Y10S430/1055—Radiation sensitive composition or product or process of making
- Y10S430/114—Initiator containing
- Y10S430/122—Sulfur compound containing
- Y10S430/123—Sulfur in heterocyclic ring
Landscapes
- Physics & Mathematics (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Spectroscopy & Molecular Physics (AREA)
- General Physics & Mathematics (AREA)
- Materials For Photolithography (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Exposure And Positioning Against Photoresist Photosensitive Materials (AREA)
Description
本申請案是2010年11月30日申請的美國臨時申請案案號61/418,196的正式申請案,其內容全文併入本申請案作為參考。
本發明係關於光酸產生劑、包含該光酸產生劑之光阻劑或經塗佈膜、或使用該光阻劑之用於形成電子裝置的方法。
暴露於光譜中紫外光區域(亦即<300nm)的輻射時會分解產生酸之化合物(在本申請案中是指「光酸產生劑」)是在微電子應用的化學放大光阻劑中,「化學放大」聚合物的去保護或交聯的基礎。已經在波長例如248nm與193nm操作的成像工具(步進器)所使用的光阻劑中觀察到,所述光阻劑的分解產物包含主要的低分子量有機分子,例如異丁烯(來自高活化能量光阻劑)與乙醛(來自低活化能量光阻劑)以及來自光酸產生劑的分解產物。這些物質的排氣(outgassing)會塗覆與腐蝕光學元件。
已經實施用以限制分解產物排氣之效應的測量,例如清潔光學元件與/或在光學元件與光阻劑塗層之間包含犧牲障蔽或過濾器。然而,隨著產業趨勢朝向在小於45nm之越來越小的線寬增加解析度,以及隨著發展在顯著更短波長(例如在極紫外線(EUV)區域13.5nm)操作且具有更先進的反射光學元件的新工具,重新需要控制光阻劑中組成層級的排氣。
已有研究關於在EUV曝光期間光阻劑對於光阻劑排氣的貢獻。Pollentier(Study of EUV Resist Outgassing/Contamination for Device Integration using EUVL Processes,Pollentier,I.,J. Photopolym. Sci. Technol
.,2010
,vol. 23(5),pp. 605-612))已經發現在藉由殘留氣體分析(RGA)(其中樣品暴露在密封腔室中,以及藉由氣體層析/質量光譜儀分析暴露之後的氣氛)測試一些光阻劑排氣之後,所測試光阻劑的一些主要分解產物包含低分子量化合物,例如苯以及二苯硫醚為光酸產生劑(例如研究的光酸產生劑是三氟甲烷磺酸三苯基鋶鹽)的分解產物。特別地,含硫的揮發性分解產物受到關注,因這些材料被認為是無法有效從光學元件清除的物質,甚至造成問題,原因是以三苯基鋶陽離子(於後文中有時稱鋶陽離子為硫鎓陽離子)為基礎的離子光酸產生劑具有所欲高敏感性並且在光阻劑中提供快速的光速度(<10mJ/cm2
)。
在一實施例中,習知技藝的上述與其他缺陷可由式(I)的光酸產生劑化合物克服:
G+
Z-
(I)
其中G具有式(II)的結構:
在另一實施例中,光阻劑包括該光酸產生劑化合物以及包括酸敏感官能基的聚合物。
在另一實施例中,經塗佈基板包括(a)基板,具有於其表面上之要被圖案化之一或多層;以及(b)在該要被圖案化的一或多層上方的光阻劑組成物層。
在另一實施例中,形成電子裝置的方法包括(a)在基板上施用申請專利範圍第9項所述之光阻劑組成物層;(b)圖案式曝光該光阻劑組成物層至活化輻射;以及(c)顯影該曝光的光阻劑組成物層,提供光阻劑浮凸影像。
本申請案揭露新的光酸產生劑(在本申請案稱為PAG),當暴露至光化輻射時,以及特別是當用於暴露於先進微影輻射(例如e-光束、x-射線,以及波長13.5nm的極紫外光(EUV)輻射之光阻劑組成物時,其具有低排氣性質。該光酸產生劑是鎓陽離子的鹽,其對於這些光化輻射具有高敏感性,但是相較於具有例如二苯基碘鎓陽離子以及三苯基硫鎓陽離子的習知PAG,這些PAG在類似的光阻劑組成物的條件、曝光與處理下的分解產物減少。
本申請案中「鎓(onium)」是指碘鎓(iodonium)或硫鎓(sulfonium)陽離子。本申請案中「經取代」是指包含例如鹵素(亦即F、Cl、Br、I)、羥基、胺基、硫醇、羧基、羧酸鹽、醯胺、腈、硫醇、硫化物、二硫化物、硝基、C1-10
烷基、C1-10
烷氧基、C6-10
芳香基、C6-10
芳氧基、C7-10
烷基芳香基、C7-10
烷基芳氧基或是包括上述至少一者的組合之取代基。可理解關於本申請案化學式揭露之任何基或結構可經取代,除非特別另行聲明或是該取代會顯著不利影響所得結構的性質。同樣地,本申請案中「(甲基)丙烯酸酯」是指丙烯酸酯或是甲基丙烯酸酯,並且除非特別聲明,否則不限於其中任何一者。
本申請案揭露的PAG是基於陽離子-陰離子結構,其中所述陽離子是經芳香基取代的鎓(亦即經二取代的碘鎓或是經三取代的硫鎓)陽離子,其分子量大於三苯基硫鎓陽離子所具分子量,或是具有其中該芳香基取代基附接至一或多個相鄰芳香基的結構,該相鄰芳香基為在例如包含鎓鹽之雜環結構中者,或是為稠合芳香環系統的一部分。
因此,本申請案揭露的PAG包含式(I)的化合物:
G+
Z-
(I)
其中G是經芳香基取代的鎓鹽陽離子,以及Z是以合適強酸(例如磺酸或是磺醯亞胺的陰離子)的共軛鹼為基礎的陰離子。
G具有式(II):
其中在式(II)中,X是鎓雜原子,較佳是S或I。每一個R0
共同附接至X,以及獨立為C1-30
烷基;多環或單環C3-30
環烷基;多環或單環C6-30
芳香基;或包括前述至少一者的組合。
陽離子G(由式(II)表示)可具有分子量大於263.4g/mol(亦即大於三苯基硫鎓陽離子(C6
H5
)3
S+
的分子量,也稱為TPS陽離子)之分子量。當G的分子量大於TPS陽離子的分子量,應理解該芳香基取代基係進一步結構上大於TPS,以及G的分解產物的分子量大於TPS的對應分解產物的分子量。
或者,式(II)的G具有之分子量可小於263.4 g/mol,限制條件為一或多個R0
更連接至相鄰的R0
。例如,共同連接至鎓雜原子(I或S)中心的相鄰苯基可在為苯基與鎓雜原子之間的附接點之鄰位(或間位,或對位,或獨立通過不同接點之間,當其中一芳香基是苯基而相鄰芳香基是不同的,例如萘基、蒽基等)進一步藉由下述者連接至彼此:單鍵、或是藉由C1-20
橋接官能基(例如亞甲基或是經取代的亞甲基)、雜原子(例如O、S、N或類似物),或是較長的橋接(例如伸乙基、三亞甲基、o-伸苯基或m-伸苯基等)。以此方式在此實施例中,得到與五員環稠合之鄰-二-取代的聯苯基,其中聯苯基共同連接至鎓雜原子。
同樣地,在式(II)中,a是2或3,其中當X是I時,a是2,或當X是S時,a是2或3。應理解如上所述,R0
的數目可指獨立的R0
或是可指連接至X的一半R0
,其中兩個R0
共同連接至彼此與X,或是指連接至X的三分之一官能基,其中三個R0
連接至彼此與X。
較佳的PAG化合物包含其中之G具式(III)、(IV)或(V)者:
其中X是I或S,每一個R3
、R4
、R5
與R6
獨立為連接至相鄰苯基的單鍵、羥基、腈基、鹵素、C1-10
烷基、C1-10
氟烷基、C1-10
烷氧基、C1-10
氟烷氧基、C6-20
芳香基、C6-20
氟芳香基、C6-20
芳氧基、C6-20
氟芳氧基、C1-20
伸烷基或C1-20
伸烷氧基;p是2或3,其中當X是I時,p是2,以及當X是S時,p是2或3;以及每一個q與r是獨立從0至5的整數,以及s與t獨立從0至4的整數。進一步欣賞者為,在式(III)中,當X是S以及p是2,至少一R2
是連接芳香基至X之C1-20
伸烷基或C1-20
伸烷氧基。在式(V)中,Ar1
與Ar2
進一步獨立為C10-30
稠合或單鍵鍵結的多環芳香基,包含以萘基、聯苯基、蒽基、菲基、雙-芳基醚以及包含這些結構的組合(例如苯基-萘基、聯苯基-萘基等)為基礎的結構;以及R7
是為共用電子對(其中X是I),或C6-20
芳香基(其中X是S),以及可更包含取代基,例如本申請案上述的官能基。
式(I)中PAG陽離子G的例子包含以下結構:
其中X是S或I,限制條件是當X是I時,R’是未共用電子對,R是C1-10
烷基、C1-10
氟烷基、C1-10
烷氧基或C1-10
氟烷氧基,當X是S時,R’是C6-30
芳香基、C6-30
伸芳基或C7-20
烷基-芳香基,每一個R”獨立為H、OH、鹵素、C1-20
烷基、C1-20
氟烷基、C1-20
烷氧基、C1-20
氟烷氧基、C3-20
環烷基、C3-20
氟環烷基、C6-20
芳香基、C7-20
烷基-芳香基或包含上述至少一者的組合,以及每一個R’’’獨立為H、C1-20
烷基、C1-20
氟烷基、C1-20
烷氧基、C1-20
氟烷氧基、C3-20
環烷基、C3-20
氟環烷基、C6-20
芳香基、C7-20
烷基-芳香基或包含上述至少一者的組合。
式(I)的Z包括磺酸、磺醯亞胺或磺醯胺的陰離子。較佳地,Z是C1-30
烷磺酸、C3-30
環烷磺酸、C1-30
氟化烷磺酸、C3-30
氟化環烷磺酸、C6-30
芳香磺酸、C6-3
氟化芳香磺酸、C7-30
烷基芳香磺酸、C7-30
氟化烷基芳香磺酸、C1-30
氟化烷磺醯亞胺、C2-30
氟化環烷磺醯亞胺、C6-30
氟化芳香磺醯亞胺、C7-30
烷基芳香磺醯亞胺、C7-30
氟化烷基芳香磺醯亞胺或包括上述至少一者的組合的陰離子。
式(I)的Z陰離子範例包含具有下式的陰離子:
本申請案揭露的PAG較佳是用於EUV微影的光阻劑,並且當暴露至EUV輻射或是其他波長的輻射,可所欲地具有特定的吸光度以及分解特性。例如,除了在EUV區域(約12至14 nm,其中典型使用的射出是13.4至13.5 nm)中的射出光譜之外,EUV輻射源可射出光酸產生劑可能對其敏感的較長波長,例如248 nm與/或193 nm(這也是DUV與193 nm微影中使用KrF與ArF激分子雷射的發射帶)。本申請案中,PAG對於EUV的敏感性高,以及對於習知技藝稱為「帶外(OOB)」發射波長的其他發射帶的敏感性較佳是最小,亦即低於在波長(248或193 nm)典型使用之PAG的敏感性,例如三苯基硫鎓(TPS)PAG或二-(第三丁基苯基)碘鎓PAG。本申請案中之PAG較佳是對於248或193 nm輻射具有OBB敏感性,此敏感性被報導為在EUV與248或193 nm暴露條件使用PAG製備光阻劑的完全曝開劑量(dose-to-clear)(E0
,以mJ/cm2
表示)比例小於或等於1.5,特別是小於或等於1.3,更特別是小於或等於1.1,更加特別是小於或等於1.0。
可用適合製備碘鎓或硫鎓PAG的通常方法來製備PAG。本申請案中之碘鎓光酸產生劑,通常可用數種不同方法中的任一方法製備。例如,可藉由在強酸性/去氫條件(例如硫酸與醋酸酐),使用經電子供應官能基取代的C6-30
芳香基(例如由電子供應官能基(例如苯氧基)取代的苯基,以及其他類似的官能基)與碘酸鹽(例如碘酸鉀(KIO3
))的簡單縮合反應以提供經雙-芳香基取代的碘鎓鹽前驅物,而製備雙-芳香基碘鎓鹽,其中電子供應官能基例如烷基、烯烴系基、羥基、醚基、其他芳香官能基。其他可用於製造較高產量對稱與非對稱取代的碘鎓鹽前驅物的方法包含在過硼酸鈉(NaBO3
)與醋酸存在下,芳基碘化物的氧化以及與具有電子供應官能基的第二芳基碘化物或柯塞爾氏(Koser)試劑(甲苯磺酸芳基羥基碘鎓鹽,亦即Ar-I(OH)(OTs))的縮合。
硫鎓光酸產生劑的製備通常可由例如在用以促進亞磺醯基與芳基或烷基化合物縮合之合適去氫劑或路易士酸(例如硫酸或伊頓(Eaton)試劑)存在下,組合亞磺醯基二芳基化合物(亦即自較佳經上述電子供應官能基取代的C6-30
芳香基製備的二芳基亞碸)與另一官能基,例如C6-30
芳基化合物或C1-30
烷基,較佳是具有電子供應官能基,以產生陽離子。亦欣賞者為亞磺醯基二芳基化合物的縮合也可以是與取代基的分子內縮合。
用任何這些方法製備的碘鎓或硫鎓鹽可更進一步進行使用合適酸或酸式鹽、亞胺或醯胺的複分解陰離子交換,以提供具有所欲陰離子(例如上述的Z)的對應碘鎓或硫鎓鹽。較佳地,在複分解交換中使用的陰離子是磺酸或其鹽,或磺醯胺或磺醯亞胺的鹽。
本申請案於上面揭露的PAG化合物可用於製備光阻劑。在一實施例中,光阻劑包含該PAG化合物與包括酸敏感官能基的聚合物。
所述聚合物可以是任何有用於光阻劑中的聚合物,沒有限制;例如涵蓋有用於製備光阻劑的聚合物,其可用於DUV(248 nm)與193 nm曝光的化學放大正或負型光阻劑。然而,較佳地,所述聚合物為有用於製備用於進階微影之以光化輻射(例如上述的x-射線、e-光束或EUV)顯影之光阻劑。應理解光阻劑成分內容中使用的「聚合物」可指一種聚合物、多於一種聚合物,或是一或多種聚合物與光阻劑中有用的一或多種其他聚合物的組合。
較佳的聚合物可包含兩種或更多聚合單元之組合,每一單元給予所述聚合物不同的性質。較佳地,所述聚合物包含包括酸敏感官能基的第一聚合單元以及包括鹼可溶官能基的第二聚合單元。可由具有酸敏感官能基的C10-30
酸敏感烯烴系酯單體,形成第一聚合單元。所述酸敏感官能基可以是環烷基、多環烷基或芳香基,具有其上連接該烯烴系酯之三級烷基中心。較佳地,可從具有下式
或是包括以上至少一者的組合的化合物,形成第一聚合單元,其中R4
是H、F、C1-6
烷基或C1-6
氟烷基。較佳的單體範例包括其中上述結構中的R4
是-CH3
(亦即(甲基)丙烯酸酯基)者。
可由具有鹼可溶官能基的C10-30
鹼可溶烯烴系酯單體,形成第二聚合單元。所述鹼可溶官能基可以是環烷基或多環烷基的烯烴系酯,所述環烷基或多環烷基具有六氟異丙醇基與視需要之第二極性官能基,例如羥基;或乙烯基芳香酯,或是烯烴系酯,具有酚系羥基(phenolic hydroxyl)或是六氟異丙醇基的芳香基作為鹼可溶官能基。較佳地,可從具有下式
或是包含上述至少一者的組合的鹼可溶單體,形成第二聚合單元,其中R5
是H、F、C1-6
烷基或C1-6
氟烷基。
係欣賞包含上述指出之第一與第二聚合單元的單體的所有聚合物係與本申請案揭露的光酸產生劑一起涵蓋。係欣賞所述聚合物可包含其他的單體單元,例如衍生自C8-20
乙烯基芳香基例如苯乙烯、4-羥基苯乙烯等;於C4-20
烯烴系酐例如馬來酸酐、伊康酸酐、甲基順丁烯二酸酐等上包含降莰烯與經取代的降莰烯的C7-20
環烯烴;其他C10-30
(甲基)丙烯酸酯單體,包含具有內酯官能基者,例如α-(γ-丁內酯)(甲基)丙烯酸酯,以及包含上述至少一者的組合。
除了PAG化合物與聚合物之外,光阻劑尚可包含添加物,所述添加物包含例如光可分解的鹼以及界面活性劑。也可包含其他添加物,例如溶解速度抑制劑、敏化劑、其他PAG等。光阻劑成分溶解在溶劑中,以滋分散與塗佈。
光阻劑可包含光可分解的鹼。包含鹼物質(較佳是光可分解陽離子的羧酸鹽)係提供中和來自酸可分解官能基之酸的機制,以及限制光產生酸的擴散,因而改善光阻劑中的對比。
光可分解的鹼包含光可分解的陽離子(較佳為亦可用於製備PAG的陽離子),其與弱酸(pKa>2)的陰離子配對,所述弱酸例如C1-20
羧酸。羧酸之例包括如甲酸、醋酸、丙酸、酒石酸、丁二酸、環己甲酸、苯甲酸、水楊酸以及其他此類羧酸。光可分解的鹼之例包括組合以下結構的陽離子與陰離子者,其中所述陽離子是三苯基硫鎓或是以下結構之一:
其中R獨立為H、C1-20
烷基、C6-20
芳香基或C6-20
烷基芳香基,以及陰離子是
其中R獨立為H、C1-20
烷基、C1-20
烷氧基、C6-20
芳香基或C6-20
烷基芳香基。其他光可分解的鹼包含基於非離子光分解發色基(chromophore),例如2-硝基苄基以及安息香基(benzoin)者。例如,光鹼產生劑是鄰-硝基苄基氨基甲酸酯。
或者,或此外,其他添加劑可包含非光可分解鹼的猝熄劑(quencher),例如以氫氧化物、羧酸鹽、胺、亞胺與醯胺為基礎的猝熄劑。較佳地,所述猝熄劑包含C1-30
有機胺、亞胺或醯胺,或可以是強鹼(例如氫氧化物或烷氧化物)或弱鹼(例如羧酸鹽)的C1-30
四級銨鹽。猝熄劑的範例包含胺,例如朝格爾鹼(Troger's base)、受阻胺(hindered amine)例如二氮雜雙環十一烯(DBU)或二氮雜雙環壬烯(DBM),或是離子猝熄劑包含四級烷基銨鹽,例如四丁基氫氧化銨(TBAH)或是四丁基乳酸銨。
界面活性劑包含氟化的與非氟化的界面活性劑,以及較佳是非離子化的。氟化的非離子界面活性劑的範例包含全氟C4
界面活性劑,例如從3M公司購得的FC-4430與FC-4432界面活性劑;以及氟二醇,例如從Omnova購得的POLYFOX PF-636、PF-6320、PF-656與PF-6520的氟界面活性劑。
光阻劑復包含溶劑,通常適合用於溶解、分散與塗佈光阻劑中使用的成分。溶劑的範例包含苯甲醚;醇包括乳酸乙酯、1-甲氧基-2-丙醇與1-乙氧基-2-丙醇;酯包含醋酸正丁酯、1-甲氧基-2-丙基醋酸鹽、甲氧基乙氧基丙酸鹽、乙氧基乙氧基丙酸酯;酮包含環己酮與2-庚酮,以及包括上述溶劑至少其中之一的組合。
本申請案揭露的光阻劑組成物可包含的PAG量為少於或等於50 wt%,特別是1至40 wt%,更特別是1至30 wt%,以及更加特別是2至20 wt%,基於固體總重量計。本申請案揭露的光阻劑組成物也包含聚合物,聚合物的量是50至99 wt%,特別是55至95 wt%,更特別是60至90 wt%,以及更加特別是65至90 wt%,基於固體總重計。
光阻劑中光鹼產生劑的量是0.01至5 wt%,特別是0.1至4 wt%,以及更特別是0.2至3 wt%,基於固體總重計。界面活性劑的量是0.01至5 wt%,特別是0.1至4 wt%,以及更特別是0.2至3 wt%,基於固體總重計。包含的猝熄劑是相對較少量,例如從0.03至5 wt%,基於固體總重計。可包含其他添加物,其他添加物的量少於或等於30 wt%,特別是少於或等於20%,更特別是少於或等於10%,基於固體總重計。應理解固體包含PAG、聚合物、光鹼產生劑、猝熄劑、界面活性劑以及任何視需要之添加物。光阻劑組成物的總固體量可為0.5至50 wt%,特別是1 to 45 wt%,更特別是2至40 wt%,以及更加特別是5至35 wt%,基於固體與溶劑總重。應理解所述固體包含PAG、聚合物、光鹼產生劑、猝熄劑、界面活性劑以及任何任何視需要之添加物,排除溶劑。
可使用包含本申請揭露的PAG的光阻劑,以提供包括所述光阻劑的層,當在相同條件下暴露至EUV輻射時,所產生揮發性降解產物濃度低於從包括比較光阻劑之層造成的揮發性降解產物濃度,所述比較光阻劑包括式(I)的光酸產生劑,但其中G是三苯基硫鎓陽離子。可藉由例如殘餘氣體分析(RGA)或膜收縮技術,決定相對的排氣。
可從包含該PAG的光阻劑,形成經塗佈基板。所述經塗佈基板包含:(a)基板,具有於其表面上之要被圖案化的一或多層;以及(b)在該要被圖案化的一或多層上方之包含該PAG之光阻劑組成物層。
基板可以是任何大小或形狀,以及較佳是可用於光微影者,例如矽、二氧化矽、絕緣體上矽(SOI)、應力矽、砷化鎵、經塗佈基板包含塗佈有氮化矽、氮氧化矽、氮化鈦、氮化鉭、超薄柵極氧化物,例如二氧化鉿、金屬者或經金屬塗佈的基板,包含被鈦、鉭、銅、鋁、鎢、其合金以及其組合塗佈者。較佳地,本申請案基板的表面包含要被圖案化的關鍵尺寸層,包含例如一或多層柵極階層層或是在基板上之用於半導體製造的其他關鍵尺寸層。所述基板較佳包含矽、SOI、應力矽與其他基板材料,形成為圓形晶圓,直徑例如200mm、300mm或更大,或是任何適用於晶圓製造生產的其他尺寸。
再者,形成電子裝置的方法包含(a)在基板的表面施加一層包含PAG的光阻劑組成物;(b)圖案式曝光所述光阻劑組成物層至活化輻射;以及(c)顯影所述曝光光阻劑組成物層,提供阻劑浮凸影像。
可用任何合適的方法完成施加,包含旋轉塗佈、噴霧塗佈、浸泡塗布、刮刀塗佈或類似的方法。較佳是藉由使用塗佈軌道,旋轉塗佈溶於溶劑中的光阻劑而完成施加所述光阻劑層,其中所述光阻劑是分散在旋轉晶圓上。在分散過程中,晶圓旋轉速度高達4,000 rpm,較佳是從約500至3,0000 rpm,以及更佳是1,000至2,500 rpm。旋轉經塗佈晶圓以移除溶劑,請通常在熱盤上烘烤經塗佈晶圓,以進一步移除殘留的溶劑以及從薄膜上移除空隙。
而後使用曝光工具,例如步進器(stepper),進行圖案式曝光,其中通過圖案遮罩輻射所述薄膜,因而圖案式曝光。所述方法較佳是使用進階曝光工具,產生能有高解析度波長的活化輻射(包含極紫外光(EUV)或e-光束輻射)。係欣賞,該使用活化輻射的曝光係在曝光區域分解PAG,並且產生酸與分解副產物,並且酸在聚合物中造成化學變化(使酸敏感官能基去封阻,而產生鹼可溶官能基,或催化在曝光區域中之交聯反應)。所述曝光工具的解析度可低於30 nm。
而後,藉由以合適的顯影劑處理經曝光層,而完成曝光光阻劑層的顯影,所述合適顯影劑可選擇性移除薄膜的曝光部分(其中所述光阻劑是正型光阻劑),或是移除薄膜的未曝光部分(則所述光阻劑是負型光阻劑)。較佳地,所述光阻劑為正型是基於具有酸敏感(可去保護的)官能基的聚合物,以及所述顯影劑較佳是無金屬離子的四烷基氫氧化銨溶液,例如水溶液0.26 N四甲基氫氧化銨。在顯影之後,形成圖案。
當光阻劑用於一或多個所述圖案形成製程時,可用於製造電子與光電裝置,例如記憶體裝置、處理器晶片(CPU的)、繪圖晶片以及其他裝置。
以下實施例更進一步說明本發明。本申請中除了以下有提供程序者之外,所有的化合物皆可購得。藉由Varian的INOVA 500 NMR光譜儀與OMNI-PROBE(對於質子,操作於500 MHz)或GEMINI 300 NMR質譜儀(對於氟,操作於282 MHz)的核磁共振(NMR)光譜進行結構定性。除非特別另行聲明,所有試劑皆是購買而得。比較例的PAG,1,1,2,2,3,3,4,4,4-九氟丁烷-1-磺酸三苯基硫鎓鹽(TPS-PFBuS)與1,1,2,2,3,3,4,4,4-九氟丁烷-1-磺酸雙(4-第三丁基苯基)碘鎓鹽(DTBPI-PFBuS)是從Toyo Gosei Co. Ltd購買而得。
實施例1:合成1,1,2,2,3,3,4,4,4-九氟丁烷-1-磺酸(4-第三丁基苯基)二萘-2-基-硫鎓鹽。A:合成雙(2-萘基)硫醚。在氮氣下,將2-奈酚(33.3 g,0.23 mol)、2-萘硫酚(36.7 g,0.23 mol)與對-甲苯磺酸(44g,0.23 mol)的混合物,在甲苯(500 mL)加熱回流4小時。冷卻之後,用飽和的碳酸氫鈉溶液猝熄所述反應。而後用CH2
Cl2
萃取所述混合物,用H2
O清洗組合的有機萃取液,而後用旋轉蒸發濃縮至乾燥。於甲苯結晶而純化粗產物,產生52克(79%)的硫化物。1
H NMR(CDCl3
) δ=7.44-7.52(m,3H),7.72-7.85(m,3H),7.9(br s,1H)。
B:合成PAG。將DTBPI-PFBuS(3.4 g,4.91 mmol)、作為二芳基硫醚之雙(2-萘基)硫醚(1.43 g,4.99 mmol,1.02當量(eq)),以及苯甲酸銅(0.038 g,0.124 mmol,0.025eq)懸浮在氯苯(約10 mL)中,加熱至80℃達約3小時,並且冷卻至室溫(而後縮寫為r.t.)。減壓下,藉由旋轉蒸發來濃縮反應混合物,用沸騰的己烷清洗粗殘留物;乾燥而得呈灰白色固體之標題化合物(2.94 g,83%)。1
H NMR(acetone-d 6
) δ: 8.71(s,2H),8.37(d,J=9 Hz,2H),8.18(d,J=8.5 Hz,2H),8.12(d,J=8 Hz,2H),8.00(d,J=8.5 Hz,2H),7.89-7.96(m,4H),7.87(t,J=8 Hz,2H),7.79(t,J=8 Hz,2H),1.39(s,9H).19
F NMR(acetone-d 6
) δ: -82.21(3F),-115.72(2F),0122.38(2F),-127.00(2F)。
實施例2:合成4,4'-亞磺醯基二酚。在4,4'-硫二酚(125 g,0.573 mol,1.5 eq.)乙醇(1.25 L)溶液中,以4小時滴入過氧化氫(溶在水中濃度為30 wt%,50 mL,0.382 mol)與三氟甲磺酸酐(32.4 mL,0.191 mmol,.0.5 eq.)之乙醇(350 mL)溶液。在完全加入之後,在室溫攪拌反應混合物30分鐘,在真空下濃縮,用醋酸乙酯(1 L)稀釋,以及用水(600 mL)清洗。用醋酸乙酯(3×600 mL)清洗水層,將組合的有機層乾燥(Na2
SO4
),以及真空濃縮。用甲基第三丁基醚(1 L)稀釋粗固體,並起攪拌過夜。用甲基第三丁基醚(3×500 mL)清洗沉澱物,並且空氣乾燥提供可定量產率之呈白色固體的標題化合物。1
H NMR(acetone-d 6
) δ: 8.85-9.05(brs,2H),7.50(d,J=8.5 Hz,4H),6.95(d,J=8.5 Hz,4H)。
B:合成(2-(2-甲氧基乙氧基)乙氧基)苯。將酚(15.0 g,0.159 mol)、碳酸鉀(26.4 g,0.191 mol,1.2 eq)與四甲基伸乙二胺(0.92 g,7.95 mmol,0.05 eq.)溶解在二甲基亞碸(DMSO;100 mL)並且在室溫攪拌30分鐘。加入1-溴-2-(2-甲氧基乙氧基)乙烷(30.56 g,0.166 mol,1.04 eq.),加熱溶液至90℃達18小時,並且冷卻至室溫。用醋酸乙酯(600 mL)稀釋反應混合物,用1 M氫氧化鉀(3×300 mL)清洗反應混合物,乾燥(Na2
SO4
),並且真空濃縮,提供呈橘色油的標題化合物(16.50 g,52%)。1
H NMR(acetone-d 6
) δ: 7.27(dt,J=8.5 Hz,1 Hz,2H),6.94(dd,J=8 Hz,1 Hz,2H),6.92(dt,J=8 Hz,1 Hz,1H),4.12(t,J=5 Hz,2H),3.80(t,J=5 Hz,2H),3.64(t,J=5 Hz,2H),3.50(t,J=5 Hz,2H),3.29(s,3H)。
C.合成4,4'-亞磺醯基雙((2-(2-甲氧基乙氧基)乙氧基)苯)。將4,4'-亞磺醯基二酚(20.0 g,85.0 mmol)、碳酸鉀(26.6 g,0.192 mol,2.26 eq.)與四甲基伸乙二胺(0.495 g,4.25 mmol,0.05 eq.)溶解在DMSO(100 mL),並且在室溫攪拌30分鐘。而後,加入1-溴-2-(2-甲氧基乙氧基)乙烷(32.67 g,0.179 mmol,2.1 eq.),加熱溶液至90℃達18小時,並且冷卻至室溫。用醋酸乙酯(600 mL)稀釋反應混合物,用水(5×500 mL)清洗反應混合物,乾燥(Na2
SO4
),以及真空乾燥,提供呈橘色油的標題化合物(33.40 g,90%)。1
H NMR(acetone-d 6
) δ: 7.59(d,J=8.5 Hz,4H),7.07(d,J=8.5 Hz,4H),4.17(t,J=4.5 Hz,4H),3.80(t,J=5 Hz,4H),3.63(t,J=4.5 Hz,4H),3.48(t,J=4.5 Hz,4H),3.28(s,6H)。
D.合成1,1,2,2,3,3,4,4,4-九氟丁烷-1-磺酸參(4-(2-(2-甲氧基乙氧基)乙氧基)苯基)硫鎓鹽。在4,4'-亞磺醯基雙((2-(2-甲氧基乙氧基)乙氧基)苯)(1.00 g,2.28 mmol)與(2-(2-甲氧基乙氧基)乙氧基)苯(0.447 g,2.28 mmol,1 eq.)之二氯甲烷(5 mL)溶液中,以2小時滴入伊頓試劑(7.7 wt%P2
O5
在甲烷磺酸中;4 mL),以及在室溫攪拌過夜。加水(75 mL)緩慢猝熄反應混合物,以及用醋酸乙酯(4×50 mL)萃取反應混合物。1,1,2,2,3,3,4,4,4-九氟丁烷-1-磺酸鉀(1.54 g,4.56 mmol,2 eq.)加至水層,而後加入二氯甲烷(100 mL),所得的二相混合物在室溫攪拌過夜。使其分層,用二氯甲烷(3×50 mL)萃取水層,以及在真空中濃縮組合的有機層。在熱水(100 mL)中溶解粗油,用甲基第三丁基醚(2x 50 mL)萃取,接著再用二氯甲烷(3×100 mL)萃取。將二氯甲烷層乾燥(Na2
SO4
),以及在真空濃縮,提供呈橘色油的標題化合物(0.80 g,38%)。1
H NMR(acetone-d 6
) δ: 7.79(d,J=9.5 Hz,6H),7.34(d,J=9 Hz,6H),4.29(t,J=5 Hz,6H),3.85(t,J=5 Hz,6H),3.64(t,J=5 Hz,6H),3.49(t,J=5 Hz,6H),3.28(s,9H).19
F NMR(300 MHz,(CD3
)2
CO) δ: -82.21(3F),-115.89(2F),-122.42(2F),-127.00(2F)。
實施例3至5與7至9. 根據以下的二芳基硫醚製程,製備用於實施例3至5與7至9之PAG的前驅硫化物,以及根據實施例1的通常製程,製備對應的PAG,除了使用表1所示使用特定的二芳基硫醚與試劑莫耳比例,以及使用甲基第三丁基醚、二氯甲烷與庚烷或己烷的混合物作為沉澱溶劑。
合成雙(4-二聯苯)硫醚(用於實施例3的前驅物)。在N2
下,在130℃加熱4-碘聯苯(25 g,0.089 mol)、無水Na2
S(3.84 g,0.049 mol)、CuI(1.7 g,8.9 mmol)與K2
CO3
(6.77 g,0.049 mol)的無水DMF(100 mL)懸浮液達24小時。冷卻之後,加水以及用二氯甲烷萃取混合物。用2N NaOH(aq.)清洗組合的有機相,而後用水清洗。移除溶劑,以及用管柱層析(矽/己烷)純化殘留物,產生9.4 g(31%)的硫化物。1
H NMR(CDCl3
) δ 7.33-7.38(m,1H),7.42-7.48(m,4H),7.54-7.61(m,4H)。
合成雙(1-萘基)硫醚(用於實施例4的前驅物)。在N2
下,在130℃加熱1-碘荼(25.4 g,0.10 mol)、無水Na2
S(3.90 g,0.05 mol)、CuI(1.71 g,9.0 mmol)與K2
CO3
(6.91 g,0.05 mol)的無水N,N-二甲基甲醯胺(DMF,100 mL)懸浮液達24小時。冷卻之後,加水以及用二氯甲烷萃取混合物。用2N NaOH清洗組合的有機相,而後用水清洗。用旋轉蒸發移除溶劑,以及用管柱層析(矽/己烷)純化殘留物,產生9.7 g(34%)的硫化物。1
H NMR(CDCl3
) δ 7.31-7.33(m,2H),7.51-7.56(m,2H),7.78(dd,J
=4.25,4.25 Hz,1H)7.89(dd,J
=6.25,3.2 Hz,1H)8.43(dd,J
=6.1,3.5 Hz,1H)。
合成4-聯苯(2-萘基)硫醚(用於實施例5的前驅物)。在N2
下,回流2-萘硫酚(2.14g,0.134 mol)、4-碘聯苯(25.0 g,0.89 mol)、CuI(16.95 g,0.089 mol)、K2
CO3
(12.3 g,0.089 mol)與乙二醇(10 mL)的第三戊醇(500 mL)混合物達48小時。冷卻之後,加入二氯甲烷,以及用2N NaOH、水清洗混合物,以及通過氧化鋁塞過濾混合物。在真空下移除溶劑,以及用管柱層析(矽/己烷)純化殘留物,產生8.9 g(32%)的硫化物。1
H NMR(CDCl3
) δ 7.33-7.38(m,1H),4.41-7.50(m,7H),7.52-7.61(m,4H),7.74-7.84(m,3H),7.9(br s,1H)。
合成(雙-4-溴苯基)硫醚(用於實施例7的前驅物)。在室溫下,將溴(38.4 g,0.24 mol)滴加至二苯硫醚(18.6 g,0.1 mol)於二氯甲烷(50 mL)與H2
O(50 mL)混合物中之溶液。添加之後,加入飽和的亞硫酸氫鈉水溶液,消耗過多的溴。用二氯甲烷萃取粗產物,以及用水清洗組合的有機層。用旋轉蒸發移除溶劑,以及於異丙酮結晶產物,產生29.6 g(86%)的硫醚。1
H NMR(CDCl3
) δ 7.19(d,J
=8.5 Hz,4H),7.43(d,J
=8.5,4H)。
合成雙(4-五氟苯氧基苯基)硫醚(用於實施例8的前驅物)。在N2
下,於90℃加熱4,4’-硫二酚(20.0 g,0.092 mol)、六氟苯(68 g,0.37 mol)與K2
CO3
之無水DMF(150 mL)達48小時。冷卻之後,加水,並且用二氯甲烷萃取混合物。用水清洗有機層,以及用旋轉蒸發移除二氯甲烷。用管柱層析(矽膠/己烷)純化粗產物,產生41 g(81.3%)的硫化物。1
H NMR(CDCl3
) δ 6.91(d,J
=8.75 Hz),7.31(d,J
=8.75 Hz)。
合成9-蒽基(2-萘基)硫醚(用於實施例9的前驅物)。在N2
下,回流2-萘硫酚(15.5 g,0.097 mol)、9-溴蒽(25.0 g,0.0.097 mol)、CuI(19.1 g,0.1 mol)、K2
CO3
(15.0 g,0.11 mol)、KI(16.6 g,0.1 mol)與乙二醇(10 mL)的第三戊醇(500 mL)混合物48小時。冷卻之後,加入二氯甲烷,以及用2N NaOH與水清洗混合物,並且通過氧化鋁塞過濾混合物。在真空下,用旋轉蒸氣移除溶劑,用管柱層析(矽/己烷)純化殘留物,產生16.5 g(50.5%)的硫化物。1
H NMR(CDCl3
) δ 7.13(dd,J
=8.7,1.85 Hz,1H)7.28-7.35(m,3H),7.43-7.47(m,1H),7.49-7.56(m,4H),7.58(d,J
=8.7 Hz,1H),7.66-7.70(m,1H),8.06-8.10(m,2H),8.64(s,1H),8.84-8.89(m,2H)。
實施例6. 根據實施例2之步驟A與D的程序製備實施例6的PAG,除了步驟D中是使用購買(Sigma-Aldrich)而得的2,6-二甲基酚(0.975 g,7.98 mmol. 1 eq.)代替(2-(2-甲氧基乙氧基)乙氧基)苯,並且使用3.50 g(7.98 mmol,1 eq.)的4,4'-亞磺醯基雙((2-(2-甲氧基乙氧基)乙氧基)苯)以及3.24 g(9.58 mmol,1.2 eq,)的1,1,2,2,3,3,4,4,4-九氟丁烷-1-磺酸鉀。
表2說明實施例3至9的PAG的定性數據(1
H NMR)。
實施例10:合成1,1,2,2,3,3,4,4,4-九氟丁烷-1-磺酸聯苯-4-基(4-苯氧基苯基)碘鎓鹽。在40℃,分次加入四水合過硼酸鈉(55mmol,8.46g)至4-碘聯苯(5.00mmol,1.40g)之冰醋酸(45mL)溶液中,攪拌8小時,並且冷卻至室溫。真空中,將反應體積減少至20mL,用水(50mL)稀釋,以及用二氯甲烷(3 x 20mL)萃取。將組合的有機部分乾燥(MgSO4
),並且真空濃縮,產生4-二乙醯氧碘聯苯,用於下一步驟,不需要進一步純化。
將對-甲苯磺酸(1 eq,0.364g,2.00mmol)之乙腈(3mL)溶液加入至4-二乙醯氧碘聯苯(1 eq,0.796g,2.00mmol)的乙腈(3mL)溶液,而後加入苯基醚(1 eq,0.340g,2.00mmol)的乙腈(1mL),在室溫攪拌2小時。用水(20mL)稀釋反應混合物,以及用庚烷(3 x 10mL)萃取反應混合物。將二氯甲烷(20mL)加入水層,而後加入1,1,2,2,3,3,4,4,4-九氟丁烷-1-磺酸鉀(1.1 eq,0.744g,2.20mmol),在室溫攪拌過夜。用水(3x 20mL)清洗有機層,乾燥(MgSO4
),以及真空濃縮,以提供目標化合物。
來自實施例1至10的PAG陽離子如表1中所示;每一個PAG陽離子是根據以下合成程序用1,1,2,2,3,3,4,4,4-九氟丁烷-1-磺酸鹽(全氟丁烷磺酸鹽,PFBuS)陰離子製備而得。
聚合物A的合成。將甲基丙烯酸1-乙基環戊酯(59.24g,0.325 mole)、甲基丙烯酸(2-異丙基)-2-金剛烷酯(12.18g,0.046 mole)、甲基丙烯酸α-(γ-丁內酯)(39.51g,0.232 mole)、甲基丙烯酸(3-羥基)-1-金剛烷酯(65.84g,0.279 mole)與甲基丙烯酸3,5-雙(1,1,1,3,3,3-六氟-2-羥基丙-2-基)環己酯(23.23g,0.046 mole)溶解在300g的乳酸乙酯(簡稱EL)、丙二醇單甲醚醋酸酯(簡稱PGMEA)與γ-丁內酯(比例分別為40/30/30 v/v)溶劑混合物。將VAZO V-601起始劑(32.08g;可自DuPont購買而得)溶解在20 g的相同溶劑混合物中。將含有額外280 g溶劑混合物的反應器加熱至70至72℃,在此溫度加入起始劑溶液。數分鐘之後,以3.5小時將單體溶液饋送至反應器。反應溶液在70℃繼續維持30分鐘。在攪拌的11.6 L的水中,利用沉澱分離粗聚合物,收集粗聚合物,並且空氣乾燥。將空氣乾燥的聚合物溶解在976.8g的溶劑混合物中,以及沉澱在19.5L甲醇與水(比例分別為80/20 v/v)的攪拌混合物中,收集並且空氣乾燥。在真空烘箱中,於60℃乾燥所述聚合物,產生128.6g(64%)白色粉末的聚合物A(GPC: Mw=6,551,多分散度=1.41)。
聚合物B的合成。將甲基丙烯酸1-乙基環戊酯(48.78g,0.268 mole)、甲基丙烯酸(2-異丙基)-2-金剛烷酯(10.03g,0.038 mole)、甲基丙烯酸-γ-丁內酯(45.55g,0.268 mole)與甲基丙烯酸3,5-雙(1,1,1,3,3,3-六氟-2-羥基丙烷-2-基)環己酯(95.64g,0.191 mole)溶解在300g EL、PGMEA與γ-丁內酯的溶劑混合物(比例分別為40/30/30 v/v)。將VAZO V-601起始劑(27.29g;可自DuPont購買而得)溶解在20 g的溶劑混合物中。將含有額外280 g溶劑混合物的反應器加熱至70至75℃,在此溫度加入起始劑溶液。數分鐘之後,以3.5小時將單體溶液饋送至反應器。反應溶液在70至71℃繼續維持30分鐘。在攪拌的12L甲醇與水混合物(比例分別為50/50 v/v)中,利用沉澱分離粗聚合物,收集粗聚合物,並且空氣乾燥。將空氣乾燥的聚合物溶解在760.2g的溶劑混合物中,以及沉澱在15.2L甲醇與水(比例分別為50/50 v/v)的攪拌混合物中,收集並且空氣乾燥。在真空烘箱中,於60℃乾燥所述聚合物,產生165g(82%)白色粉末的聚合物B(GPC: Mw=6,655,多分散度=1.60)。
光阻劑製備與加工。比較配方實施例:正型光阻劑組成物的製備是藉由組合5.563g 10 wt%聚合物A的EL溶液、5.563g 10 wt%聚合物B的EL溶液、6.250g 2 wt% TPS-PFBuS(比較PAG實施例)的EL溶液、1.113g 1 wt%朝格爾鹼的PGMEA溶液、0.250g of 0.5 wt% Omnova PF656界面活性劑的EL溶液、21.51g EL溶劑與9.750g PGMEA。過濾調配的阻劑(0.2μm)。
配方實施例1至8. 根據比較配方實施例(CFEx)描述的配方,換成表4中指定的量,製備含有實施例1至6、8與9的PAG的正型光阻劑組成物。
上述光阻劑配方CFEx與配方實施例FEx.1至8微影製程如下。使用TEL ACT-8(Tokyo Electron)塗佈軌道將配方阻劑旋轉塗佈在200 mm矽晶圓上,所述矽晶圓上具有底部抗反射塗佈層(BARC)(用於248nm曝光,Rohm and Haas Electronic Materials LLC的ARTM
9;或是用於193nm曝光,Rohm and Haas Electronic Materials LLC的ARTM
19;或是用於EUV的有機下方層),以及在130℃軟烘烤90秒,形成厚度約60 nm的阻劑膜。用248nm KrF準分子雷射輻射、193nm ArF準分子雷射輻射或EUV輻射(eMET,13.4至13.5 nm),透過光遮罩曝光光阻劑層,以及所述曝光層在曝光之後90℃烘烤(PEB)60秒。而後,用不含金屬離子的鹼顯影劑(0.26N四甲基氫氧化銨水溶液)處理經塗佈晶圓,顯影所述光阻劑層。
表5顯示每一個曝光波長的完全曝光劑量(dose-to-clear,E0
)與之於在248 nm與193 nm EUV(帶外敏感度,OOB)的阻劑清除劑量。
如表5所示,PAG實施例1至6、8與9各顯示對於EUV輻射的所欲敏感度(如以E0
量測者),雖比較例(CFEx.具有三苯基硫鎓陽離子)的敏感度(2.7 mJ/cm2
)高於除了實施例2(2.0 mJ/cm2
)與6(1.6 mJ/cm2
)以外的所有實施例的敏感度。然而,相較於CFEx(在248 nm的OOB=0.6),實施例1、3至6、8與9的PAG各自在248 nm具有改善的帶外敏感度(在248 nm的OOB是0.4或更小),以及相較於CFEx(在193 nm的OOB=1.9),實施例1至6、8與9的所有PAG在193 nm具有改善的OOB(在193 nm的OOB是1.5或更小)。因此,可知實施例1至6、8與9的PAG皆對於EUV曝光敏感,以及對於非EUV曝光波長的敏感度低於比較例。
本申請案揭露的所有範圍包含端點,並且端點可獨立彼此組合。本申請案中,字尾“(s)”是用以包含名詞的單數與複數,藉以包含至少一個所述名詞。「視需要」或是「視需要地」指後續描述的事件或環境可發生或可不發生,以及所指描述包含事件發生的例子以及不發生的例子。在本申請案中,「組合」包含混合品、混合物、合金或是反應產物。所有參考資料皆併入本案作為參考。
除非特別聲明或與內文明顯矛盾之外,本發明描述內容中使用「一(a)」「一(an)」與「該」以及類似指代(特別是在以下申請專利範圍中)解讀為涵蓋單數與複數。再者,「第一」、「第二」以及類似用詞並不代表任何順序、量或重要性,而是用於將一個元件與另一元件分別。
Claims (9)
- 一種具有式(I)的化合物,G+ Z- (I)其中G+ 具有式(V):
- 如申請專利範圍第1項所述之化合物,其中G+ 是:
- 如申請專利範圍第2項所述之化合物,其中Z- 是C1-30 烷磺酸、C3-30 環烷磺酸、C1-30 氟化烷磺酸、C3-30 氟化環烷磺酸、C6-30 芳基磺酸、C6-3 氟化芳基磺酸、C7-30 烷基芳基磺酸、C7-30 氟化烷基芳基磺酸、C1-30 氟化烷磺醯亞胺、C2-30 氟化環烷磺醯亞胺、C6-30 氟化芳基磺醯亞胺、C7-30 烷基芳基磺醯亞胺、C7-30 氟化烷基芳基磺醯亞胺或包括上述至少一者的組合的陰離子。
- 如申請專利範圍第3項所述之化合物,其中Z- 是:
- 一種光阻劑,其包括申請專利範圍第1至4項任一項所述之化合物以及包括酸敏感官能基的聚合物。
- 如申請專利範圍第5項所述之光阻劑,其中該聚合物包括包括酸敏感官能基的第一聚合單元以及包括鹼可溶官能基的第二聚合單元。
- 如申請專利範圍第6項所述之光阻劑,其中該第一聚合 單元係從具有下式
- 一種經塗佈基板,包括:(a)基板,該基板具有於其表面上之要被圖案化的一或 多層;以及(b)申請專利範圍第5項所述之光阻劑的層,係位在該要被圖案化的一或多層上。
- 一種用於形成電子裝置的方法,包括:(a)在基板的表面上,施加申請專利範圍第5項所述之光阻劑的層;(b)將該光阻劑組成物層圖案式曝光至活化輻射;以及(c)將曝光的光阻劑組成物層顯影,以提供阻劑浮凸影像。
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US41819610P | 2010-11-30 | 2010-11-30 |
Publications (2)
Publication Number | Publication Date |
---|---|
TW201231445A TW201231445A (en) | 2012-08-01 |
TWI465421B true TWI465421B (zh) | 2014-12-21 |
Family
ID=45093461
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
TW100143281A TWI465421B (zh) | 2010-11-30 | 2011-11-25 | 光酸產生劑 |
Country Status (6)
Country | Link |
---|---|
US (1) | US8932797B2 (zh) |
EP (1) | EP2458440A1 (zh) |
JP (3) | JP6049250B2 (zh) |
KR (1) | KR101393613B1 (zh) |
CN (2) | CN102617430A (zh) |
TW (1) | TWI465421B (zh) |
Families Citing this family (34)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP5903833B2 (ja) | 2010-11-09 | 2016-04-13 | 住友化学株式会社 | 樹脂、レジスト組成物及びレジストパターン製造方法 |
KR101830595B1 (ko) | 2010-11-09 | 2018-02-21 | 스미또모 가가꾸 가부시키가이샤 | 수지 및 포토레지스트 조성물 |
EP2458440A1 (en) * | 2010-11-30 | 2012-05-30 | Rohm and Haas Electronic Materials LLC | Photoacid generators |
JP2012168279A (ja) * | 2011-02-10 | 2012-09-06 | Tokyo Ohka Kogyo Co Ltd | Euv用レジスト組成物、euv用レジスト組成物の製造方法、およびレジストパターン形成方法 |
JP5866100B2 (ja) * | 2011-04-13 | 2016-02-17 | 住友化学株式会社 | レジスト組成物及びレジストパターンの製造方法 |
JP6297269B2 (ja) * | 2012-06-28 | 2018-03-20 | ローム アンド ハース エレクトロニック マテリアルズ エルエルシーRohm and Haas Electronic Materials LLC | ポリマー組成物、このポリマー組成物を含むフォトレジスト、およびこのフォトレジストを含むコーティングされた物品 |
JP6571912B2 (ja) * | 2012-12-31 | 2019-09-04 | ローム アンド ハース エレクトロニック マテリアルズ エルエルシーRohm and Haas Electronic Materials LLC | 樹状化合物、フォトレジスト組成物、および電子デバイスを作製する方法 |
JP6014507B2 (ja) * | 2013-02-05 | 2016-10-25 | 富士フイルム株式会社 | 感活性光線性又は感放射線性樹脂組成物、感活性光線性又は感放射線性膜、パターン形成方法及び電子デバイスの製造方法 |
US8980538B2 (en) * | 2013-03-14 | 2015-03-17 | Tokyo Electron Limited | Chemi-epitaxy in directed self-assembly applications using photo-decomposable agents |
US9063420B2 (en) | 2013-07-16 | 2015-06-23 | Rohm And Haas Electronic Materials Llc | Photoresist composition, coated substrate, and method of forming electronic device |
US8962779B2 (en) | 2013-07-16 | 2015-02-24 | Dow Global Technologies Llc | Method of forming polyaryl polymers |
US9410016B2 (en) | 2013-07-16 | 2016-08-09 | Dow Global Technologies Llc | Aromatic polyacetals and articles comprising them |
US8933239B1 (en) | 2013-07-16 | 2015-01-13 | Dow Global Technologies Llc | Bis(aryl)acetal compounds |
US9581901B2 (en) | 2013-12-19 | 2017-02-28 | Rohm And Haas Electronic Materials Llc | Photoacid-generating copolymer and associated photoresist composition, coated substrate, and method of forming an electronic device |
US9229319B2 (en) | 2013-12-19 | 2016-01-05 | Rohm And Haas Electronic Materials Llc | Photoacid-generating copolymer and associated photoresist composition, coated substrate, and method of forming an electronic device |
CN105446084B (zh) * | 2014-08-28 | 2019-03-08 | 中芯国际集成电路制造(上海)有限公司 | 一种光刻方法 |
CN107074759B (zh) * | 2014-09-26 | 2021-12-14 | 东京应化工业株式会社 | 锍盐、光产酸剂及感光性组合物 |
JP6472097B2 (ja) * | 2014-12-05 | 2019-02-20 | 東洋合成工業株式会社 | スルホン酸誘導体、それを用いた光酸発生剤、レジスト組成物及びデバイスの製造方法 |
WO2017038286A1 (ja) * | 2015-08-28 | 2017-03-09 | Dic株式会社 | 有機化合物、その製造法、それを含有する有機半導体材料及びそれを含有する有機トランジスタ |
TWI656111B (zh) | 2015-12-31 | 2019-04-11 | Rohm And Haas Electronic Materials Llc | 光酸產生劑 |
TWI662364B (zh) * | 2015-12-31 | 2019-06-11 | Rohm And Haas Electronic Materials Llc | 光致抗蝕劑組合物、包含光致抗蝕劑組合物的經塗佈基板及形成電子裝置的方法 |
JP6583136B2 (ja) * | 2016-05-11 | 2019-10-02 | 信越化学工業株式会社 | 新規スルホニウム化合物及びその製造方法、レジスト組成物、並びにパターン形成方法 |
JP6782569B2 (ja) * | 2016-06-28 | 2020-11-11 | 東京応化工業株式会社 | レジスト組成物及びレジストパターン形成方法 |
JP2020015713A (ja) * | 2018-07-11 | 2020-01-30 | 住友化学株式会社 | 塩、酸発生剤、レジスト組成物及びレジストパターンの製造方法 |
WO2020065318A1 (en) | 2018-09-28 | 2020-04-02 | Datalase Ltd. | Colour forming composition |
JP7186592B2 (ja) * | 2018-12-04 | 2022-12-09 | 東京応化工業株式会社 | レジスト組成物、レジストパターン形成方法、及び化合物 |
JP7347154B2 (ja) * | 2019-11-21 | 2023-09-20 | 株式会社デンソー | 電動航空機用電駆動システムの制御装置、電動航空機およびコンピュータプログラム |
JP2021181429A (ja) * | 2020-05-15 | 2021-11-25 | 住友化学株式会社 | 塩、酸発生剤、レジスト組成物及びレジストパターンの製造方法 |
JP7447725B2 (ja) | 2020-07-29 | 2024-03-12 | Jsr株式会社 | 感放射線性樹脂組成物及びレジストパターン形成方法 |
US11852972B2 (en) * | 2020-10-30 | 2023-12-26 | Rohm And Haas Electronic Materials Llc | Photoresist compositions and pattern formation methods |
JP2022183077A (ja) * | 2021-05-28 | 2022-12-08 | 住友化学株式会社 | 塩、酸発生剤、レジスト組成物及びレジストパターンの製造方法 |
JP2022183074A (ja) * | 2021-05-28 | 2022-12-08 | 住友化学株式会社 | 塩、酸発生剤、レジスト組成物及びレジストパターンの製造方法 |
JP2023032149A (ja) * | 2021-08-26 | 2023-03-09 | 東京応化工業株式会社 | レジスト組成物、レジストパターン形成方法、化合物、酸発生剤、酸拡散制御剤、及び高分子化合物 |
WO2023222740A1 (en) * | 2022-05-20 | 2023-11-23 | Merck Patent Gmbh | Substrate coating resist composition and method for manufacturing resist pattern |
Citations (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US6060207A (en) * | 1994-07-11 | 2000-05-09 | Kabushiki Kaisha Toshiba | Photosensitive material |
US6458506B2 (en) * | 1998-08-14 | 2002-10-01 | Shipley Company, Llc | Photoacid generators and photoresists comprising same |
US20030013049A1 (en) * | 2001-02-25 | 2003-01-16 | Shipley Company, L.L.C. | Photoacid generator systems for short wavelength imaging |
US20040265733A1 (en) * | 2003-06-30 | 2004-12-30 | Houlihan Francis M. | Photoacid generators |
EP1705518A2 (en) * | 2005-03-22 | 2006-09-27 | Fuji Photo Film Co., Ltd. | Positive resist composition and pattern forming method using the same |
US20070298352A1 (en) * | 2006-06-27 | 2007-12-27 | Shin-Etsu Chemical Co., Ltd. | Novel sulfonate salts and derivatives, photoacid generators, resist compositions, and patterning process |
Family Cites Families (35)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4451409A (en) | 1982-02-08 | 1984-05-29 | The Dow Chemical Company | Sulfonium organosulfonates |
TW436663B (en) | 1995-11-02 | 2001-05-28 | Shinetsu Chemical Co | Sulfonium salts and chemically amplified positive resist compositions |
US7147983B1 (en) * | 1996-10-07 | 2006-12-12 | Shipley Company, L.L.C. | Dyed photoresists and methods and articles of manufacture comprising same |
KR100279497B1 (ko) * | 1998-07-16 | 2001-02-01 | 박찬구 | 술포늄 염의 제조방법 |
TWI263866B (en) * | 1999-01-18 | 2006-10-11 | Sumitomo Chemical Co | Chemical amplification type positive resist composition |
US6200728B1 (en) * | 1999-02-20 | 2001-03-13 | Shipley Company, L.L.C. | Photoresist compositions comprising blends of photoacid generators |
US6664022B1 (en) | 2000-08-25 | 2003-12-16 | Shipley Company, L.L.C. | Photoacid generators and photoresists comprising same |
JP4225699B2 (ja) * | 2001-03-12 | 2009-02-18 | 富士フイルム株式会社 | ポジ型感光性組成物 |
JP2003149812A (ja) * | 2001-11-08 | 2003-05-21 | Fuji Photo Film Co Ltd | ポジ型感光性組成物 |
GB0204467D0 (en) | 2002-02-26 | 2002-04-10 | Coates Brothers Plc | Novel fused ring compounds, and their use as cationic photoinitiators |
JP2004151184A (ja) * | 2002-10-29 | 2004-05-27 | Japan Atom Energy Res Inst | 化学増幅型感放射線レジスト組成物及びそれを用いたパターン形成方法 |
US8110337B2 (en) * | 2002-12-18 | 2012-02-07 | Fujifilm Corporation | Polymerizable composition and lithographic printing plate precursor |
US6878504B2 (en) * | 2003-05-28 | 2005-04-12 | Everlight Usa, Inc. | Chemically-amplified resist compositions |
JP2006251551A (ja) * | 2005-03-11 | 2006-09-21 | Fuji Photo Film Co Ltd | ポジ型レジスト組成物及びそれを用いたパターン形成方法。 |
JP4696009B2 (ja) * | 2005-03-22 | 2011-06-08 | 富士フイルム株式会社 | ポジ型レジスト組成物及びそれを用いたパターン形成方法 |
JP4536622B2 (ja) * | 2005-08-23 | 2010-09-01 | 東京応化工業株式会社 | ポジ型レジスト組成物およびレジストパターン形成方法 |
US7932334B2 (en) * | 2005-12-27 | 2011-04-26 | Sumitomo Chemical Company, Limited | Resin suitable for an acid generator |
JP2007293250A (ja) | 2006-03-27 | 2007-11-08 | Fujifilm Corp | ポジ型レジスト組成物およびそれを用いたパターン形成方法 |
TWI412888B (zh) | 2006-08-18 | 2013-10-21 | Sumitomo Chemical Co | 適合作為酸產生劑之鹽及含有該鹽之化學放大型正光阻組成物 |
US7718344B2 (en) * | 2006-09-29 | 2010-05-18 | Fujifilm Corporation | Resist composition and pattern forming method using the same |
JP2008127300A (ja) * | 2006-11-17 | 2008-06-05 | Tokyo Ohka Kogyo Co Ltd | 化合物、酸発生剤、レジスト組成物及びレジストパターン形成方法 |
JP2008169231A (ja) * | 2007-01-06 | 2008-07-24 | Konica Minolta Medical & Graphic Inc | 活性光線硬化型組成物、活性光線硬化型インク、活性光線硬化型組成物の硬化方法及び画像形成方法 |
JP5303122B2 (ja) * | 2007-06-12 | 2013-10-02 | 東京応化工業株式会社 | 高分子化合物、ポジ型レジスト組成物およびレジストパターン形成方法 |
US7776510B2 (en) | 2007-06-13 | 2010-08-17 | Tokyo Ohka Kogyo Co., Ltd. | Resist composition, method of forming resist pattern, compound and acid generator |
JP5066405B2 (ja) | 2007-08-02 | 2012-11-07 | 富士フイルム株式会社 | 電子線、x線又はeuv用レジスト組成物及び該組成物を用いたパターン形成方法 |
JP2009098448A (ja) * | 2007-10-17 | 2009-05-07 | Idemitsu Kosan Co Ltd | 極端紫外光用及び/又は電子線用フォトレジスト組成物及びそれを用いた微細加工方法 |
TWI391781B (zh) * | 2007-11-19 | 2013-04-01 | Tokyo Ohka Kogyo Co Ltd | 光阻組成物,光阻圖型之形成方法,新穎化合物及酸產生劑 |
JP2009280535A (ja) * | 2008-05-23 | 2009-12-03 | Nippon Carbide Ind Co Inc | 新規な光酸発生剤及びそれを含むレジスト材料 |
JP4990844B2 (ja) * | 2008-06-17 | 2012-08-01 | 信越化学工業株式会社 | パターン形成方法並びにこれに用いるレジスト材料 |
JP5481046B2 (ja) * | 2008-08-13 | 2014-04-23 | 東京応化工業株式会社 | レジスト組成物、レジストパターン形成方法、新規な化合物および酸発生剤 |
US8455176B2 (en) * | 2008-11-12 | 2013-06-04 | Az Electronic Materials Usa Corp. | Coating composition |
US8716385B2 (en) * | 2008-12-15 | 2014-05-06 | Central Glass Company, Limited | Polymerizable fluoromonomer, fluoropolymer, resist material, and method of pattern formation |
KR101700980B1 (ko) * | 2009-02-20 | 2017-01-31 | 산아프로 가부시키가이샤 | 술포늄염, 광산 발생제 및 감광성 수지 조성물 |
TWI464140B (zh) * | 2009-12-10 | 2014-12-11 | 羅門哈斯電子材料有限公司 | 膽酸鹽光酸產生劑及含該光酸產生劑之光阻 |
EP2458440A1 (en) * | 2010-11-30 | 2012-05-30 | Rohm and Haas Electronic Materials LLC | Photoacid generators |
-
2011
- 2011-11-24 EP EP11190453A patent/EP2458440A1/en not_active Withdrawn
- 2011-11-24 JP JP2011255772A patent/JP6049250B2/ja active Active
- 2011-11-25 TW TW100143281A patent/TWI465421B/zh active
- 2011-11-29 KR KR1020110126170A patent/KR101393613B1/ko active IP Right Grant
- 2011-11-30 CN CN2011104631875A patent/CN102617430A/zh active Pending
- 2011-11-30 CN CN201910842301.1A patent/CN110531581A/zh active Pending
- 2011-11-30 US US13/307,198 patent/US8932797B2/en active Active
-
2016
- 2016-06-17 JP JP2016120782A patent/JP2017002047A/ja active Pending
-
2018
- 2018-11-29 JP JP2018223899A patent/JP2019059755A/ja active Pending
Patent Citations (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US6060207A (en) * | 1994-07-11 | 2000-05-09 | Kabushiki Kaisha Toshiba | Photosensitive material |
US6458506B2 (en) * | 1998-08-14 | 2002-10-01 | Shipley Company, Llc | Photoacid generators and photoresists comprising same |
US20030013049A1 (en) * | 2001-02-25 | 2003-01-16 | Shipley Company, L.L.C. | Photoacid generator systems for short wavelength imaging |
US20040265733A1 (en) * | 2003-06-30 | 2004-12-30 | Houlihan Francis M. | Photoacid generators |
EP1705518A2 (en) * | 2005-03-22 | 2006-09-27 | Fuji Photo Film Co., Ltd. | Positive resist composition and pattern forming method using the same |
US20070298352A1 (en) * | 2006-06-27 | 2007-12-27 | Shin-Etsu Chemical Co., Ltd. | Novel sulfonate salts and derivatives, photoacid generators, resist compositions, and patterning process |
Also Published As
Publication number | Publication date |
---|---|
CN102617430A (zh) | 2012-08-01 |
US20120141939A1 (en) | 2012-06-07 |
JP2017002047A (ja) | 2017-01-05 |
KR101393613B1 (ko) | 2014-05-12 |
US8932797B2 (en) | 2015-01-13 |
JP2012136511A (ja) | 2012-07-19 |
CN110531581A (zh) | 2019-12-03 |
JP6049250B2 (ja) | 2016-12-21 |
KR20120059424A (ko) | 2012-06-08 |
EP2458440A1 (en) | 2012-05-30 |
TW201231445A (en) | 2012-08-01 |
JP2019059755A (ja) | 2019-04-18 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
TWI465421B (zh) | 光酸產生劑 | |
US8900792B2 (en) | Polymerizable photoacid generators | |
TWI672289B (zh) | 聚合性單體、聚合物、光阻材料及圖案形成方法 | |
TWI637940B (zh) | 鋶鹽、光阻組成物及圖案形成方法 | |
TWI444394B (zh) | 光敏組成物 | |
TWI412893B (zh) | 含有熱酸產生劑之光阻下層材料,形成光阻下層膜之基板及圖型形成方法 | |
TWI245161B (en) | Novel onium salts, photoacid generators, resist compositions, and patterning process | |
TWI588602B (zh) | 光阻組成物及光阻圖型之形成方法 | |
TWI534531B (zh) | 光阻組成物,光阻圖型之形成方法,高分子化合物 | |
TW594402B (en) | Novel onium salts, photoacid generators, resist compositions, and patterning process | |
WO2018074382A1 (ja) | 組成物及びそれを用いたデバイスの製造方法 | |
TWI557507B (zh) | 光阻圖型之形成方法 | |
TWI541606B (zh) | 抗蝕圖型之形成方法及圖型微細化處理劑 | |
TWI482803B (zh) | 杯芳烴化合物及含該化合物之光阻劑組成物 | |
KR20130032854A (ko) | 칼릭스아렌 및 이를 포함하는 포토레지스트 조성물 | |
JP5798964B2 (ja) | パターン形成方法、及び、これらを用いる電子デバイスの製造方法 | |
JP2023016886A (ja) | 感光性樹脂組成物及びその製造方法、レジスト膜、パターン形成方法、並びに、電子デバイスの製造方法 | |
KR20170031054A (ko) | 화학 증폭형 레지스트 재료 및 레지스트 패턴 형성 방법 | |
TW202120475A (zh) | 鋶鹽、酸產生劑、抗蝕劑組成物和裝置的製造方法 | |
US8343706B2 (en) | Fluorine-free fused ring heteroaromatic photoacid generators and resist compositions containing the same | |
TW201439670A (zh) | 光阻組成物,光阻圖型之形成方法 | |
WO2021065350A1 (ja) | 感放射線性樹脂組成物及びそれを用いたレジストパターンの形成方法 |