US20150309406A9 - Photoresist composition, resist pattern-forming method, acid diffusion control agent, and compound - Google Patents
Photoresist composition, resist pattern-forming method, acid diffusion control agent, and compound Download PDFInfo
- Publication number
- US20150309406A9 US20150309406A9 US14/486,532 US201414486532A US2015309406A9 US 20150309406 A9 US20150309406 A9 US 20150309406A9 US 201414486532 A US201414486532 A US 201414486532A US 2015309406 A9 US2015309406 A9 US 2015309406A9
- Authority
- US
- United States
- Prior art keywords
- hydrocarbon group
- group
- carbon atoms
- formula
- hydrogen atom
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- 239000002253 acid Substances 0.000 title claims abstract description 134
- 150000001875 compounds Chemical class 0.000 title claims abstract description 126
- 239000000203 mixture Substances 0.000 title claims abstract description 123
- 229920002120 photoresistant polymer Polymers 0.000 title claims abstract description 115
- 239000003795 chemical substances by application Substances 0.000 title claims abstract description 98
- 238000009792 diffusion process Methods 0.000 title claims abstract description 91
- 238000000034 method Methods 0.000 title claims description 14
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 138
- 229920000642 polymer Polymers 0.000 claims abstract description 108
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 97
- 125000002723 alicyclic group Chemical group 0.000 claims abstract description 67
- 125000004433 nitrogen atom Chemical group N* 0.000 claims abstract description 23
- 125000004429 atom Chemical group 0.000 claims abstract description 12
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims abstract description 7
- 230000005855 radiation Effects 0.000 claims abstract description 3
- 125000001183 hydrocarbyl group Chemical group 0.000 claims abstract 51
- 229910052731 fluorine Inorganic materials 0.000 claims description 54
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical group [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 claims description 42
- 239000011737 fluorine Substances 0.000 claims description 42
- 229910052799 carbon Inorganic materials 0.000 claims description 35
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 32
- 229910052757 nitrogen Inorganic materials 0.000 claims description 30
- 150000001721 carbon Chemical group 0.000 claims description 26
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 9
- 150000002430 hydrocarbons Chemical group 0.000 description 92
- -1 1-ethyl-1-cyclopentyl Chemical group 0.000 description 75
- 239000002904 solvent Substances 0.000 description 48
- 0 *C(=O)OC([1*])([2*])[3*] Chemical compound *C(=O)OC([1*])([2*])[3*] 0.000 description 24
- 238000011161 development Methods 0.000 description 20
- 230000018109 developmental process Effects 0.000 description 20
- 125000001153 fluoro group Chemical group F* 0.000 description 19
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 18
- 239000007788 liquid Substances 0.000 description 18
- 238000006116 polymerization reaction Methods 0.000 description 18
- 230000015572 biosynthetic process Effects 0.000 description 16
- 238000007654 immersion Methods 0.000 description 16
- WGTYBPLFGIVFAS-UHFFFAOYSA-M tetramethylammonium hydroxide Chemical compound [OH-].C[N+](C)(C)C WGTYBPLFGIVFAS-UHFFFAOYSA-M 0.000 description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 14
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 13
- 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 12
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
- 230000000052 comparative effect Effects 0.000 description 12
- 230000002349 favourable effect Effects 0.000 description 12
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 11
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 11
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 10
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 10
- 125000004122 cyclic group Chemical group 0.000 description 10
- 238000009826 distribution Methods 0.000 description 10
- 238000011156 evaluation Methods 0.000 description 10
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 10
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 9
- 238000006243 chemical reaction Methods 0.000 description 9
- 238000010894 electron beam technology Methods 0.000 description 9
- 150000002148 esters Chemical class 0.000 description 9
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 9
- 238000003786 synthesis reaction Methods 0.000 description 9
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 8
- 125000000217 alkyl group Chemical group 0.000 description 8
- 238000004458 analytical method Methods 0.000 description 8
- DKPFZGUDAPQIHT-UHFFFAOYSA-N butyl acetate Chemical compound CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 8
- CATSNJVOTSVZJV-UHFFFAOYSA-N heptan-2-one Chemical compound CCCCCC(C)=O CATSNJVOTSVZJV-UHFFFAOYSA-N 0.000 description 8
- 150000002576 ketones Chemical class 0.000 description 8
- YFSUTJLHUFNCNZ-UHFFFAOYSA-N perfluorooctane-1-sulfonic acid Chemical compound OS(=O)(=O)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F YFSUTJLHUFNCNZ-UHFFFAOYSA-N 0.000 description 8
- 150000008053 sultones Chemical group 0.000 description 8
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 7
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 7
- 239000003513 alkali Substances 0.000 description 7
- 230000000694 effects Effects 0.000 description 7
- 239000000178 monomer Substances 0.000 description 7
- 239000003960 organic solvent Substances 0.000 description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- ORILYTVJVMAKLC-UHFFFAOYSA-N adamantane Chemical group C1C(C2)CC3CC1CC2C3 ORILYTVJVMAKLC-UHFFFAOYSA-N 0.000 description 6
- 125000004183 alkoxy alkyl group Chemical group 0.000 description 6
- 125000003545 alkoxy group Chemical group 0.000 description 6
- 125000003277 amino group Chemical group 0.000 description 6
- 239000011248 coating agent Substances 0.000 description 6
- 238000000576 coating method Methods 0.000 description 6
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 6
- AFABGHUZZDYHJO-UHFFFAOYSA-N dimethyl butane Natural products CCCC(C)C AFABGHUZZDYHJO-UHFFFAOYSA-N 0.000 description 6
- JBTWLSYIZRCDFO-UHFFFAOYSA-N ethyl methyl carbonate Chemical compound CCOC(=O)OC JBTWLSYIZRCDFO-UHFFFAOYSA-N 0.000 description 6
- 238000005227 gel permeation chromatography Methods 0.000 description 6
- 230000001235 sensitizing effect Effects 0.000 description 6
- 239000000758 substrate Substances 0.000 description 6
- 150000005846 sugar alcohols Polymers 0.000 description 6
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 description 6
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 6
- 239000004215 Carbon black (E152) Substances 0.000 description 5
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 5
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical group C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 5
- 150000003997 cyclic ketones Chemical group 0.000 description 5
- 230000003247 decreasing effect Effects 0.000 description 5
- 229930195733 hydrocarbon Natural products 0.000 description 5
- 150000002596 lactones Chemical group 0.000 description 5
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 5
- 125000000962 organic group Chemical group 0.000 description 5
- 239000000843 powder Substances 0.000 description 5
- 238000002360 preparation method Methods 0.000 description 5
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 5
- 230000001681 protective effect Effects 0.000 description 5
- 230000002829 reductive effect Effects 0.000 description 5
- 230000035945 sensitivity Effects 0.000 description 5
- 125000000565 sulfonamide group Chemical group 0.000 description 5
- 239000004094 surface-active agent Substances 0.000 description 5
- 235000012431 wafers Nutrition 0.000 description 5
- 238000005406 washing Methods 0.000 description 5
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 description 4
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 4
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 4
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 description 4
- ATHHXGZTWNVVOU-UHFFFAOYSA-N N-methylformamide Chemical compound CNC=O ATHHXGZTWNVVOU-UHFFFAOYSA-N 0.000 description 4
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical group C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 4
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 4
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 4
- 230000003667 anti-reflective effect Effects 0.000 description 4
- 125000003118 aryl group Chemical group 0.000 description 4
- RWGFKTVRMDUZSP-UHFFFAOYSA-N cumene Chemical compound CC(C)C1=CC=CC=C1 RWGFKTVRMDUZSP-UHFFFAOYSA-N 0.000 description 4
- 150000005676 cyclic carbonates Chemical group 0.000 description 4
- 150000004292 cyclic ethers Chemical group 0.000 description 4
- 230000007547 defect Effects 0.000 description 4
- 230000006866 deterioration Effects 0.000 description 4
- 239000004210 ether based solvent Substances 0.000 description 4
- QWTDNUCVQCZILF-UHFFFAOYSA-N isopentane Chemical compound CCC(C)C QWTDNUCVQCZILF-UHFFFAOYSA-N 0.000 description 4
- 238000005259 measurement Methods 0.000 description 4
- 238000002156 mixing Methods 0.000 description 4
- UMRZSTCPUPJPOJ-KNVOCYPGSA-N norbornane Chemical compound C1C[C@H]2CC[C@@H]1C2 UMRZSTCPUPJPOJ-KNVOCYPGSA-N 0.000 description 4
- LLHKCFNBLRBOGN-UHFFFAOYSA-N propylene glycol methyl ether acetate Chemical compound COCC(C)OC(C)=O LLHKCFNBLRBOGN-UHFFFAOYSA-N 0.000 description 4
- 229910052710 silicon Inorganic materials 0.000 description 4
- 239000010703 silicon Substances 0.000 description 4
- DSSYKIVIOFKYAU-XCBNKYQSSA-N (R)-camphor Chemical group C1C[C@@]2(C)C(=O)C[C@@H]1C2(C)C DSSYKIVIOFKYAU-XCBNKYQSSA-N 0.000 description 3
- ARXJGSRGQADJSQ-UHFFFAOYSA-N 1-methoxypropan-2-ol Chemical compound COCC(C)O ARXJGSRGQADJSQ-UHFFFAOYSA-N 0.000 description 3
- VWYMQCMKEVZSFW-UHFFFAOYSA-N 2-methylbutan-2-yl 4-hydroxypiperidine-1-carboxylate Chemical compound CCC(C)(C)OC(=O)N1CCC(O)CC1 VWYMQCMKEVZSFW-UHFFFAOYSA-N 0.000 description 3
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 3
- KXDHJXZQYSOELW-UHFFFAOYSA-N Carbamic acid Chemical group NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 description 3
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 3
- RGSFGYAAUTVSQA-UHFFFAOYSA-N Cyclopentane Chemical compound C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 3
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical class S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- 239000004793 Polystyrene Substances 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical class C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 125000002252 acyl group Chemical group 0.000 description 3
- 125000005354 acylalkyl group Chemical group 0.000 description 3
- 125000004423 acyloxy group Chemical group 0.000 description 3
- 125000005041 acyloxyalkyl group Chemical group 0.000 description 3
- 125000005138 alkoxysulfonyl group Chemical group 0.000 description 3
- 125000003282 alkyl amino group Chemical group 0.000 description 3
- 125000005278 alkyl sulfonyloxy group Chemical group 0.000 description 3
- 150000001408 amides Chemical class 0.000 description 3
- 125000003710 aryl alkyl group Chemical group 0.000 description 3
- 239000002585 base Substances 0.000 description 3
- 239000004202 carbamide Substances 0.000 description 3
- 230000015556 catabolic process Effects 0.000 description 3
- 125000004093 cyano group Chemical group *C#N 0.000 description 3
- 125000000753 cycloalkyl group Chemical group 0.000 description 3
- DMEGYFMYUHOHGS-UHFFFAOYSA-N cycloheptane Chemical compound C1CCCCCC1 DMEGYFMYUHOHGS-UHFFFAOYSA-N 0.000 description 3
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 3
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 3
- 238000006731 degradation reaction Methods 0.000 description 3
- 229940009976 deoxycholate Drugs 0.000 description 3
- 125000004663 dialkyl amino group Chemical group 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 238000010828 elution Methods 0.000 description 3
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 3
- XPFVYQJUAUNWIW-UHFFFAOYSA-N furfuryl alcohol Chemical compound OCC1=CC=CO1 XPFVYQJUAUNWIW-UHFFFAOYSA-N 0.000 description 3
- 125000005843 halogen group Chemical group 0.000 description 3
- 238000010348 incorporation Methods 0.000 description 3
- 239000003999 initiator Substances 0.000 description 3
- GJRQTCIYDGXPES-UHFFFAOYSA-N isobutyl acetate Chemical compound CC(C)COC(C)=O GJRQTCIYDGXPES-UHFFFAOYSA-N 0.000 description 3
- 150000003951 lactams Chemical group 0.000 description 3
- 125000000686 lactone group Chemical group 0.000 description 3
- ZQMHJBXHRFJKOT-UHFFFAOYSA-N methyl 2-[(1-methoxy-2-methyl-1-oxopropan-2-yl)diazenyl]-2-methylpropanoate Chemical compound COC(=O)C(C)(C)N=NC(C)(C)C(=O)OC ZQMHJBXHRFJKOT-UHFFFAOYSA-N 0.000 description 3
- PSHKMPUSSFXUIA-UHFFFAOYSA-N n,n-dimethylpyridin-2-amine Chemical compound CN(C)C1=CC=CC=N1 PSHKMPUSSFXUIA-UHFFFAOYSA-N 0.000 description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 3
- 125000004430 oxygen atom Chemical group O* 0.000 description 3
- 230000036961 partial effect Effects 0.000 description 3
- 125000003386 piperidinyl group Chemical group 0.000 description 3
- 229920002223 polystyrene Polymers 0.000 description 3
- 150000003384 small molecules Chemical group 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 125000001424 substituent group Chemical group 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 2
- DHKHKXVYLBGOIT-UHFFFAOYSA-N 1,1-Diethoxyethane Chemical class CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 2
- FYGHSUNMUKGBRK-UHFFFAOYSA-N 1,2,3-trimethylbenzene Chemical compound CC1=CC=CC(C)=C1C FYGHSUNMUKGBRK-UHFFFAOYSA-N 0.000 description 2
- KVNYFPKFSJIPBJ-UHFFFAOYSA-N 1,2-diethylbenzene Chemical compound CCC1=CC=CC=C1CC KVNYFPKFSJIPBJ-UHFFFAOYSA-N 0.000 description 2
- GWEHVDNNLFDJLR-UHFFFAOYSA-N 1,3-diphenylurea Chemical compound C=1C=CC=CC=1NC(=O)NC1=CC=CC=C1 GWEHVDNNLFDJLR-UHFFFAOYSA-N 0.000 description 2
- IBXNCJKFFQIKKY-UHFFFAOYSA-N 1-pentyne Chemical compound CCCC#C IBXNCJKFFQIKKY-UHFFFAOYSA-N 0.000 description 2
- 238000005160 1H NMR spectroscopy Methods 0.000 description 2
- OJVAMHKKJGICOG-UHFFFAOYSA-N 2,5-hexanedione Chemical compound CC(=O)CCC(C)=O OJVAMHKKJGICOG-UHFFFAOYSA-N 0.000 description 2
- NXDMSYSWZQIBOX-UHFFFAOYSA-M 2-(3-bicyclo[2.2.1]heptanyl)-1,1-difluoroethanesulfonate;triphenylsulfanium Chemical compound C1CC2C(CC(F)(F)S(=O)(=O)[O-])CC1C2.C1=CC=CC=C1[S+](C=1C=CC=CC=1)C1=CC=CC=C1 NXDMSYSWZQIBOX-UHFFFAOYSA-M 0.000 description 2
- QQZOPKMRPOGIEB-UHFFFAOYSA-N 2-Oxohexane Chemical compound CCCCC(C)=O QQZOPKMRPOGIEB-UHFFFAOYSA-N 0.000 description 2
- YIWUKEYIRIRTPP-UHFFFAOYSA-N 2-ethylhexan-1-ol Chemical compound CCCCC(CC)CO YIWUKEYIRIRTPP-UHFFFAOYSA-N 0.000 description 2
- QPRQEDXDYOZYLA-UHFFFAOYSA-N 2-methylbutan-1-ol Chemical compound CCC(C)CO QPRQEDXDYOZYLA-UHFFFAOYSA-N 0.000 description 2
- GXDHCNNESPLIKD-UHFFFAOYSA-N 2-methylhexane Natural products CCCCC(C)C GXDHCNNESPLIKD-UHFFFAOYSA-N 0.000 description 2
- SVTBMSDMJJWYQN-UHFFFAOYSA-N 2-methylpentane-2,4-diol Chemical compound CC(O)CC(C)(C)O SVTBMSDMJJWYQN-UHFFFAOYSA-N 0.000 description 2
- BSKHPKMHTQYZBB-UHFFFAOYSA-N 2-methylpyridine Chemical compound CC1=CC=CC=N1 BSKHPKMHTQYZBB-UHFFFAOYSA-N 0.000 description 2
- JYVXNLLUYHCIIH-UHFFFAOYSA-N 4-hydroxy-4-methyl-2-oxanone Chemical compound CC1(O)CCOC(=O)C1 JYVXNLLUYHCIIH-UHFFFAOYSA-N 0.000 description 2
- OZJPLYNZGCXSJM-UHFFFAOYSA-N 5-valerolactone Chemical compound O=C1CCCCO1 OZJPLYNZGCXSJM-UHFFFAOYSA-N 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 2
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 2
- HSFWRNGVRCDJHI-UHFFFAOYSA-N Acetylene Chemical compound C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 description 2
- HORWXOGNROGTDE-UHFFFAOYSA-N CCC(C)(C)OC(=O)N1CCC(OC(=O)C23CC4CC(CC(C4)C2)C3)CC1.CCC(C)(C)OC(=O)N1CCC(OS(C)(=O)=O)CC1.CCOC(=O)CC(=O)OC1CCN(C(=O)OC(C)(C)CC)CC1 Chemical compound CCC(C)(C)OC(=O)N1CCC(OC(=O)C23CC4CC(CC(C4)C2)C3)CC1.CCC(C)(C)OC(=O)N1CCC(OS(C)(=O)=O)CC1.CCOC(=O)CC(=O)OC1CCN(C(=O)OC(C)(C)CC)CC1 HORWXOGNROGTDE-UHFFFAOYSA-N 0.000 description 2
- NIQCNGHVCWTJSM-UHFFFAOYSA-N Dimethyl phthalate Chemical compound COC(=O)C1=CC=CC=C1C(=O)OC NIQCNGHVCWTJSM-UHFFFAOYSA-N 0.000 description 2
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
- ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- RZKSECIXORKHQS-UHFFFAOYSA-N Heptan-3-ol Chemical compound CCCCC(O)CC RZKSECIXORKHQS-UHFFFAOYSA-N 0.000 description 2
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical compound CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 description 2
- NHTMVDHEPJAVLT-UHFFFAOYSA-N Isooctane Chemical compound CC(C)CC(C)(C)C NHTMVDHEPJAVLT-UHFFFAOYSA-N 0.000 description 2
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 2
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 2
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 2
- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 2
- OHLUUHNLEMFGTQ-UHFFFAOYSA-N N-methylacetamide Chemical compound CNC(C)=O OHLUUHNLEMFGTQ-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 239000002202 Polyethylene glycol Substances 0.000 description 2
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
- QQONPFPTGQHPMA-UHFFFAOYSA-N Propene Chemical compound CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 2
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 2
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 description 2
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 239000004115 Sodium Silicate Substances 0.000 description 2
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 2
- 229940022663 acetate Drugs 0.000 description 2
- YRKCREAYFQTBPV-UHFFFAOYSA-N acetylacetone Chemical compound CC(=O)CC(C)=O YRKCREAYFQTBPV-UHFFFAOYSA-N 0.000 description 2
- 125000004018 acid anhydride group Chemical group 0.000 description 2
- MIBQYWIOHFTKHD-UHFFFAOYSA-N adamantane-1-carbonyl chloride Chemical compound C1C(C2)CC3CC2CC1(C(=O)Cl)C3 MIBQYWIOHFTKHD-UHFFFAOYSA-N 0.000 description 2
- 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 description 2
- 239000005456 alcohol based solvent Substances 0.000 description 2
- 150000001335 aliphatic alkanes Chemical class 0.000 description 2
- 125000003368 amide group Chemical group 0.000 description 2
- 125000002029 aromatic hydrocarbon group Chemical group 0.000 description 2
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 2
- QUKGYYKBILRGFE-UHFFFAOYSA-N benzyl acetate Chemical compound CC(=O)OCC1=CC=CC=C1 QUKGYYKBILRGFE-UHFFFAOYSA-N 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- KDKYADYSIPSCCQ-UHFFFAOYSA-N but-1-yne Chemical compound CCC#C KDKYADYSIPSCCQ-UHFFFAOYSA-N 0.000 description 2
- BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 description 2
- KBPLFHHGFOOTCA-UHFFFAOYSA-N caprylic alcohol Natural products CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 125000000392 cycloalkenyl group Chemical group 0.000 description 2
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 2
- LMGZGXSXHCMSAA-UHFFFAOYSA-N cyclodecane Chemical group C1CCCCCCCCC1 LMGZGXSXHCMSAA-UHFFFAOYSA-N 0.000 description 2
- HGCIXCUEYOPUTN-UHFFFAOYSA-N cyclohexene Chemical compound C1CCC=CC1 HGCIXCUEYOPUTN-UHFFFAOYSA-N 0.000 description 2
- WJTCGQSWYFHTAC-UHFFFAOYSA-N cyclooctane Chemical compound C1CCCCCCC1 WJTCGQSWYFHTAC-UHFFFAOYSA-N 0.000 description 2
- 239000004914 cyclooctane Substances 0.000 description 2
- 125000000640 cyclooctyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 2
- BGTOWKSIORTVQH-UHFFFAOYSA-N cyclopentanone Chemical compound O=C1CCCC1 BGTOWKSIORTVQH-UHFFFAOYSA-N 0.000 description 2
- LPIQUOYDBNQMRZ-UHFFFAOYSA-N cyclopentene Chemical compound C1CC=CC1 LPIQUOYDBNQMRZ-UHFFFAOYSA-N 0.000 description 2
- NNBZCPXTIHJBJL-UHFFFAOYSA-N decalin Chemical compound C1CCCC2CCCCC21 NNBZCPXTIHJBJL-UHFFFAOYSA-N 0.000 description 2
- MWKFXSUHUHTGQN-UHFFFAOYSA-N decan-1-ol Chemical compound CCCCCCCCCCO MWKFXSUHUHTGQN-UHFFFAOYSA-N 0.000 description 2
- DIOQZVSQGTUSAI-UHFFFAOYSA-N decane Chemical compound CCCCCCCCCC DIOQZVSQGTUSAI-UHFFFAOYSA-N 0.000 description 2
- SWXVUIWOUIDPGS-UHFFFAOYSA-N diacetone alcohol Chemical compound CC(=O)CC(C)(C)O SWXVUIWOUIDPGS-UHFFFAOYSA-N 0.000 description 2
- JQVDAXLFBXTEQA-UHFFFAOYSA-N dibutylamine Chemical compound CCCCNCCCC JQVDAXLFBXTEQA-UHFFFAOYSA-N 0.000 description 2
- FLKPEMZONWLCSK-UHFFFAOYSA-N diethyl phthalate Chemical compound CCOC(=O)C1=CC=CC=C1C(=O)OCC FLKPEMZONWLCSK-UHFFFAOYSA-N 0.000 description 2
- 229910001873 dinitrogen Inorganic materials 0.000 description 2
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 2
- 239000012156 elution solvent Substances 0.000 description 2
- 239000003759 ester based solvent Substances 0.000 description 2
- 150000002168 ethanoic acid esters Chemical class 0.000 description 2
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 2
- LZCLXQDLBQLTDK-UHFFFAOYSA-N ethyl 2-hydroxypropanoate Chemical compound CCOC(=O)C(C)O LZCLXQDLBQLTDK-UHFFFAOYSA-N 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- FKRCODPIKNYEAC-UHFFFAOYSA-N ethyl propionate Chemical compound CCOC(=O)CC FKRCODPIKNYEAC-UHFFFAOYSA-N 0.000 description 2
- XLLIQLLCWZCATF-UHFFFAOYSA-N ethylene glycol monomethyl ether acetate Natural products COCCOC(C)=O XLLIQLLCWZCATF-UHFFFAOYSA-N 0.000 description 2
- 125000004997 halocarbonyl group Chemical group 0.000 description 2
- NGAZZOYFWWSOGK-UHFFFAOYSA-N heptan-3-one Chemical compound CCCCC(=O)CC NGAZZOYFWWSOGK-UHFFFAOYSA-N 0.000 description 2
- ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical compound CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 description 2
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical class I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 2
- XAOGXQMKWQFZEM-UHFFFAOYSA-N isoamyl propanoate Chemical compound CCC(=O)OCCC(C)C XAOGXQMKWQFZEM-UHFFFAOYSA-N 0.000 description 2
- NNPPMTNAJDCUHE-UHFFFAOYSA-N isobutane Chemical compound CC(C)C NNPPMTNAJDCUHE-UHFFFAOYSA-N 0.000 description 2
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 2
- 229960004592 isopropanol Drugs 0.000 description 2
- 239000005453 ketone based solvent Substances 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 2
- UAEPNZWRGJTJPN-UHFFFAOYSA-N methylcyclohexane Chemical compound CC1CCCCC1 UAEPNZWRGJTJPN-UHFFFAOYSA-N 0.000 description 2
- 125000002950 monocyclic group Chemical group 0.000 description 2
- ZWRUINPWMLAQRD-UHFFFAOYSA-N nonan-1-ol Chemical compound CCCCCCCCCO ZWRUINPWMLAQRD-UHFFFAOYSA-N 0.000 description 2
- BKIMMITUMNQMOS-UHFFFAOYSA-N nonane Chemical compound CCCCCCCCC BKIMMITUMNQMOS-UHFFFAOYSA-N 0.000 description 2
- GJQIMXVRFNLMTB-UHFFFAOYSA-N nonyl acetate Chemical compound CCCCCCCCCOC(C)=O GJQIMXVRFNLMTB-UHFFFAOYSA-N 0.000 description 2
- XNLICIUVMPYHGG-UHFFFAOYSA-N pentan-2-one Chemical compound CCCC(C)=O XNLICIUVMPYHGG-UHFFFAOYSA-N 0.000 description 2
- FDPIMTJIUBPUKL-UHFFFAOYSA-N pentan-3-one Chemical compound CCC(=O)CC FDPIMTJIUBPUKL-UHFFFAOYSA-N 0.000 description 2
- PGMYKACGEOXYJE-UHFFFAOYSA-N pentyl acetate Chemical compound CCCCCOC(C)=O PGMYKACGEOXYJE-UHFFFAOYSA-N 0.000 description 2
- 125000003367 polycyclic group Chemical group 0.000 description 2
- 229920001223 polyethylene glycol Polymers 0.000 description 2
- 239000003505 polymerization initiator Substances 0.000 description 2
- YKYONYBAUNKHLG-UHFFFAOYSA-N propyl acetate Chemical compound CCCOC(C)=O YKYONYBAUNKHLG-UHFFFAOYSA-N 0.000 description 2
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 2
- ODLMAHJVESYWTB-UHFFFAOYSA-N propylbenzene Chemical compound CCCC1=CC=CC=C1 ODLMAHJVESYWTB-UHFFFAOYSA-N 0.000 description 2
- 239000007870 radical polymerization initiator Substances 0.000 description 2
- 230000007261 regionalization Effects 0.000 description 2
- 230000002940 repellent Effects 0.000 description 2
- 239000005871 repellent Substances 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 239000004065 semiconductor Substances 0.000 description 2
- NTHWMYGWWRZVTN-UHFFFAOYSA-N sodium silicate Chemical compound [Na+].[Na+].[O-][Si]([O-])=O NTHWMYGWWRZVTN-UHFFFAOYSA-N 0.000 description 2
- 229910052911 sodium silicate Inorganic materials 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 229910052717 sulfur Inorganic materials 0.000 description 2
- 125000004434 sulfur atom Chemical group 0.000 description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- RAOIDOHSFRTOEL-UHFFFAOYSA-N tetrahydrothiophene Chemical class C1CCSC1 RAOIDOHSFRTOEL-UHFFFAOYSA-N 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- XNUYPROIFFCXAE-UHFFFAOYSA-N (4-cyclohexylphenyl)-diphenylsulfanium Chemical compound C1CCCCC1C1=CC=C([S+](C=2C=CC=CC=2)C=2C=CC=CC=2)C=C1 XNUYPROIFFCXAE-UHFFFAOYSA-N 0.000 description 1
- RUDFKNNFTLQMGW-UHFFFAOYSA-M (4-cyclohexylphenyl)-diphenylsulfanium;(7,7-dimethyl-3-oxo-4-bicyclo[2.2.1]heptanyl)methanesulfonate Chemical compound C1CC2(CS([O-])(=O)=O)C(=O)CC1C2(C)C.C1CCCCC1C1=CC=C([S+](C=2C=CC=CC=2)C=2C=CC=CC=2)C=C1 RUDFKNNFTLQMGW-UHFFFAOYSA-M 0.000 description 1
- UFADEYDBOXASBQ-UHFFFAOYSA-M (4-cyclohexylphenyl)-diphenylsulfanium;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.C1CCCCC1C1=CC=C([S+](C=2C=CC=CC=2)C=2C=CC=CC=2)C=C1 UFADEYDBOXASBQ-UHFFFAOYSA-M 0.000 description 1
- QEYKXSMQZGHJSX-UHFFFAOYSA-M (4-cyclohexylphenyl)-diphenylsulfanium;trifluoromethanesulfonate Chemical compound [O-]S(=O)(=O)C(F)(F)F.C1CCCCC1C1=CC=C([S+](C=2C=CC=CC=2)C=2C=CC=CC=2)C=C1 QEYKXSMQZGHJSX-UHFFFAOYSA-M 0.000 description 1
- HQGTWZUOVIZAKX-UHFFFAOYSA-N (4-methylsulfonylphenyl)-diphenylsulfanium Chemical compound C1=CC(S(=O)(=O)C)=CC=C1[S+](C=1C=CC=CC=1)C1=CC=CC=C1 HQGTWZUOVIZAKX-UHFFFAOYSA-N 0.000 description 1
- VKOHBZXAXOVWQU-UHFFFAOYSA-M (4-methylsulfonylphenyl)-diphenylsulfanium;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(S(=O)(=O)C)=CC=C1[S+](C=1C=CC=CC=1)C1=CC=CC=C1 VKOHBZXAXOVWQU-UHFFFAOYSA-M 0.000 description 1
- CFRRWRASBDSKBI-UHFFFAOYSA-M (4-methylsulfonylphenyl)-diphenylsulfanium;trifluoromethanesulfonate Chemical compound [O-]S(=O)(=O)C(F)(F)F.C1=CC(S(=O)(=O)C)=CC=C1[S+](C=1C=CC=CC=1)C1=CC=CC=C1 CFRRWRASBDSKBI-UHFFFAOYSA-M 0.000 description 1
- VHXIWNNSPUGPEI-UHFFFAOYSA-M (7,7-dimethyl-3-oxo-4-bicyclo[2.2.1]heptanyl)methanesulfonate;(4-methylsulfonylphenyl)-diphenylsulfanium Chemical compound C1CC2(CS([O-])(=O)=O)C(=O)CC1C2(C)C.C1=CC(S(=O)(=O)C)=CC=C1[S+](C=1C=CC=CC=1)C1=CC=CC=C1 VHXIWNNSPUGPEI-UHFFFAOYSA-M 0.000 description 1
- PQONLZARMHVIPW-UHFFFAOYSA-N (7,7-dimethyl-3-oxo-4-bicyclo[2.2.1]heptanyl)methanesulfonate;2,6-dimethyl-4-(thiolan-1-ium-1-yl)phenol Chemical compound CC1=C(O)C(C)=CC([S+]2CCCC2)=C1.C1CC2(CS([O-])(=O)=O)C(=O)CC1C2(C)C PQONLZARMHVIPW-UHFFFAOYSA-N 0.000 description 1
- HHYVKZVPYXHHCG-UHFFFAOYSA-M (7,7-dimethyl-3-oxo-4-bicyclo[2.2.1]heptanyl)methanesulfonate;diphenyliodanium Chemical compound C=1C=CC=CC=1[I+]C1=CC=CC=C1.C1CC2(CS([O-])(=O)=O)C(=O)CC1C2(C)C HHYVKZVPYXHHCG-UHFFFAOYSA-M 0.000 description 1
- FJALTVCJBKZXKY-UHFFFAOYSA-M (7,7-dimethyl-3-oxo-4-bicyclo[2.2.1]heptanyl)methanesulfonate;triphenylsulfanium Chemical compound C1CC2(CS([O-])(=O)=O)C(=O)CC1C2(C)C.C1=CC=CC=C1[S+](C=1C=CC=CC=1)C1=CC=CC=C1 FJALTVCJBKZXKY-UHFFFAOYSA-M 0.000 description 1
- FFJCNSLCJOQHKM-CLFAGFIQSA-N (z)-1-[(z)-octadec-9-enoxy]octadec-9-ene Chemical compound CCCCCCCC\C=C/CCCCCCCCOCCCCCCCC\C=C/CCCCCCCC FFJCNSLCJOQHKM-CLFAGFIQSA-N 0.000 description 1
- WYPDFLYUYKDLGV-UHFFFAOYSA-N 1,1,1,3,3,3-hexafluoro-2-(4-tetracyclo[6.2.1.13,6.02,7]dodecanylmethyl)propan-2-ol Chemical compound C12C(C3)CCC3C2C2CC(CC(O)(C(F)(F)F)C(F)(F)F)C1C2 WYPDFLYUYKDLGV-UHFFFAOYSA-N 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
- AVQQQNCBBIEMEU-UHFFFAOYSA-N 1,1,3,3-tetramethylurea Chemical compound CN(C)C(=O)N(C)C AVQQQNCBBIEMEU-UHFFFAOYSA-N 0.000 description 1
- UDYXMTORTDACTG-UHFFFAOYSA-N 1,1,3-tributylthiourea Chemical compound CCCCNC(=S)N(CCCC)CCCC UDYXMTORTDACTG-UHFFFAOYSA-N 0.000 description 1
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical class CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 1
- YBBLOADPFWKNGS-UHFFFAOYSA-N 1,1-dimethylurea Chemical compound CN(C)C(N)=O YBBLOADPFWKNGS-UHFFFAOYSA-N 0.000 description 1
- VIDOPANCAUPXNH-UHFFFAOYSA-N 1,2,3-triethylbenzene Chemical compound CCC1=CC=CC(CC)=C1CC VIDOPANCAUPXNH-UHFFFAOYSA-N 0.000 description 1
- ZZXUZKXVROWEIF-UHFFFAOYSA-N 1,2-butylene carbonate Chemical compound CCC1COC(=O)O1 ZZXUZKXVROWEIF-UHFFFAOYSA-N 0.000 description 1
- OKIRBHVFJGXOIS-UHFFFAOYSA-N 1,2-di(propan-2-yl)benzene Chemical compound CC(C)C1=CC=CC=C1C(C)C OKIRBHVFJGXOIS-UHFFFAOYSA-N 0.000 description 1
- CYSGHNMQYZDMIA-UHFFFAOYSA-N 1,3-Dimethyl-2-imidazolidinon Chemical compound CN1CCN(C)C1=O CYSGHNMQYZDMIA-UHFFFAOYSA-N 0.000 description 1
- 229940058015 1,3-butylene glycol Drugs 0.000 description 1
- 229940057054 1,3-dimethylurea Drugs 0.000 description 1
- VAYTZRYEBVHVLE-UHFFFAOYSA-N 1,3-dioxol-2-one Chemical compound O=C1OC=CO1 VAYTZRYEBVHVLE-UHFFFAOYSA-N 0.000 description 1
- SGUVLZREKBPKCE-UHFFFAOYSA-N 1,5-diazabicyclo[4.3.0]-non-5-ene Chemical compound C1CCN=C2CCCN21 SGUVLZREKBPKCE-UHFFFAOYSA-N 0.000 description 1
- SGRHVVLXEBNBDV-UHFFFAOYSA-N 1,6-dibromohexane Chemical compound BrCCCCCCBr SGRHVVLXEBNBDV-UHFFFAOYSA-N 0.000 description 1
- QWOZZTWBWQMEPD-UHFFFAOYSA-N 1-(2-ethoxypropoxy)propan-2-ol Chemical compound CCOC(C)COCC(C)O QWOZZTWBWQMEPD-UHFFFAOYSA-N 0.000 description 1
- CEZIJESLKIMKNL-UHFFFAOYSA-N 1-(4-butoxynaphthalen-1-yl)thiolan-1-ium Chemical compound C12=CC=CC=C2C(OCCCC)=CC=C1[S+]1CCCC1 CEZIJESLKIMKNL-UHFFFAOYSA-N 0.000 description 1
- BXGYVRIBHDBIJQ-UHFFFAOYSA-M 1-(4-butoxynaphthalen-1-yl)thiolan-1-ium;(7,7-dimethyl-3-oxo-4-bicyclo[2.2.1]heptanyl)methanesulfonate Chemical compound C1CC2(CS([O-])(=O)=O)C(=O)CC1C2(C)C.C12=CC=CC=C2C(OCCCC)=CC=C1[S+]1CCCC1 BXGYVRIBHDBIJQ-UHFFFAOYSA-M 0.000 description 1
- WNDABSCBNOUSTE-UHFFFAOYSA-M 1-(4-butoxynaphthalen-1-yl)thiolan-1-ium;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.C12=CC=CC=C2C(OCCCC)=CC=C1[S+]1CCCC1 WNDABSCBNOUSTE-UHFFFAOYSA-M 0.000 description 1
- JQIQJUCEFIYYOJ-UHFFFAOYSA-M 1-(4-butoxynaphthalen-1-yl)thiolan-1-ium;trifluoromethanesulfonate Chemical compound [O-]S(=O)(=O)C(F)(F)F.C12=CC=CC=C2C(OCCCC)=CC=C1[S+]1CCCC1 JQIQJUCEFIYYOJ-UHFFFAOYSA-M 0.000 description 1
- WXWSNMWMJAFDLG-UHFFFAOYSA-N 1-(6-butoxynaphthalen-2-yl)thiolan-1-ium Chemical compound C1=CC2=CC(OCCCC)=CC=C2C=C1[S+]1CCCC1 WXWSNMWMJAFDLG-UHFFFAOYSA-N 0.000 description 1
- PIUKSJQPBWVFHQ-UHFFFAOYSA-M 1-(6-butoxynaphthalen-2-yl)thiolan-1-ium;(7,7-dimethyl-3-oxo-4-bicyclo[2.2.1]heptanyl)methanesulfonate Chemical compound C1CC2(CS([O-])(=O)=O)C(=O)CC1C2(C)C.C1=CC2=CC(OCCCC)=CC=C2C=C1[S+]1CCCC1 PIUKSJQPBWVFHQ-UHFFFAOYSA-M 0.000 description 1
- WRMXJRZJMAXZNC-UHFFFAOYSA-M 1-(6-butoxynaphthalen-2-yl)thiolan-1-ium;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=CC2=CC(OCCCC)=CC=C2C=C1[S+]1CCCC1 WRMXJRZJMAXZNC-UHFFFAOYSA-M 0.000 description 1
- WFZZYWQSLJQVOT-UHFFFAOYSA-M 1-(6-butoxynaphthalen-2-yl)thiolan-1-ium;trifluoromethanesulfonate Chemical compound [O-]S(=O)(=O)C(F)(F)F.C1=CC2=CC(OCCCC)=CC=C2C=C1[S+]1CCCC1 WFZZYWQSLJQVOT-UHFFFAOYSA-M 0.000 description 1
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 description 1
- JVCBVWTTXCNJBJ-UHFFFAOYSA-N 1-azabicyclo[2.2.1]heptane Chemical group C1CC2CCN1C2 JVCBVWTTXCNJBJ-UHFFFAOYSA-N 0.000 description 1
- MNDIARAMWBIKFW-UHFFFAOYSA-N 1-bromohexane Chemical class CCCCCCBr MNDIARAMWBIKFW-UHFFFAOYSA-N 0.000 description 1
- DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical compound CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 description 1
- RWNUSVWFHDHRCJ-UHFFFAOYSA-N 1-butoxypropan-2-ol Chemical compound CCCCOCC(C)O RWNUSVWFHDHRCJ-UHFFFAOYSA-N 0.000 description 1
- FUWDFGKRNIDKAE-UHFFFAOYSA-N 1-butoxypropan-2-yl acetate Chemical compound CCCCOCC(C)OC(C)=O FUWDFGKRNIDKAE-UHFFFAOYSA-N 0.000 description 1
- VFWCMGCRMGJXDK-UHFFFAOYSA-N 1-chlorobutane Chemical class CCCCCl VFWCMGCRMGJXDK-UHFFFAOYSA-N 0.000 description 1
- JOLQKTGDSGKSKJ-UHFFFAOYSA-N 1-ethoxypropan-2-ol Chemical compound CCOCC(C)O JOLQKTGDSGKSKJ-UHFFFAOYSA-N 0.000 description 1
- LIPRQQHINVWJCH-UHFFFAOYSA-N 1-ethoxypropan-2-yl acetate Chemical compound CCOCC(C)OC(C)=O LIPRQQHINVWJCH-UHFFFAOYSA-N 0.000 description 1
- HYFLWBNQFMXCPA-UHFFFAOYSA-N 1-ethyl-2-methylbenzene Chemical compound CCC1=CC=CC=C1C HYFLWBNQFMXCPA-UHFFFAOYSA-N 0.000 description 1
- BMVXCPBXGZKUPN-UHFFFAOYSA-N 1-hexanamine Chemical compound CCCCCCN BMVXCPBXGZKUPN-UHFFFAOYSA-N 0.000 description 1
- DMFAHCVITRDZQB-UHFFFAOYSA-N 1-propoxypropan-2-yl acetate Chemical compound CCCOCC(C)OC(C)=O DMFAHCVITRDZQB-UHFFFAOYSA-N 0.000 description 1
- 125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 description 1
- LTMRRSWNXVJMBA-UHFFFAOYSA-L 2,2-diethylpropanedioate Chemical compound CCC(CC)(C([O-])=O)C([O-])=O LTMRRSWNXVJMBA-UHFFFAOYSA-L 0.000 description 1
- YAJYJWXEWKRTPO-UHFFFAOYSA-N 2,3,3,4,4,5-hexamethylhexane-2-thiol Chemical compound CC(C)C(C)(C)C(C)(C)C(C)(C)S YAJYJWXEWKRTPO-UHFFFAOYSA-N 0.000 description 1
- GQHTUMJGOHRCHB-UHFFFAOYSA-N 2,3,4,6,7,8,9,10-octahydropyrimido[1,2-a]azepine Chemical compound C1CCCCN2CCCN=C21 GQHTUMJGOHRCHB-UHFFFAOYSA-N 0.000 description 1
- WFQNMENFJSZTGD-UHFFFAOYSA-O 2,6-dimethyl-4-(thiolan-1-ium-1-yl)phenol Chemical compound CC1=C(O)C(C)=CC([S+]2CCCC2)=C1 WFQNMENFJSZTGD-UHFFFAOYSA-O 0.000 description 1
- GNZYDSUXCMLOMM-UHFFFAOYSA-N 2,6-dimethyl-4-(thiolan-1-ium-1-yl)phenol;1,1,2,2,3,3,4,4,4-nonafluorobutane-1-sulfonate Chemical compound CC1=C(O)C(C)=CC([S+]2CCCC2)=C1.[O-]S(=O)(=O)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F GNZYDSUXCMLOMM-UHFFFAOYSA-N 0.000 description 1
- VAOHUAFTTHSCRT-UHFFFAOYSA-N 2,6-dimethyl-4-(thiolan-1-ium-1-yl)phenol;trifluoromethanesulfonate Chemical compound [O-]S(=O)(=O)C(F)(F)F.CC1=C(O)C(C)=CC([S+]2CCCC2)=C1 VAOHUAFTTHSCRT-UHFFFAOYSA-N 0.000 description 1
- GRCVHLCFMAVQCF-UHFFFAOYSA-M 2-(1-adamantyl)-1,1-difluoroethanesulfonate;triphenylsulfanium Chemical compound C1C(C2)CC3CC2CC1(CC(F)(F)S(=O)(=O)[O-])C3.C1=CC=CC=C1[S+](C=1C=CC=CC=1)C1=CC=CC=C1 GRCVHLCFMAVQCF-UHFFFAOYSA-M 0.000 description 1
- VXQBJTKSVGFQOL-UHFFFAOYSA-N 2-(2-butoxyethoxy)ethyl acetate Chemical compound CCCCOCCOCCOC(C)=O VXQBJTKSVGFQOL-UHFFFAOYSA-N 0.000 description 1
- FPZWZCWUIYYYBU-UHFFFAOYSA-N 2-(2-ethoxyethoxy)ethyl acetate Chemical compound CCOCCOCCOC(C)=O FPZWZCWUIYYYBU-UHFFFAOYSA-N 0.000 description 1
- CKCGJBFTCUCBAJ-UHFFFAOYSA-N 2-(2-ethoxypropoxy)propyl acetate Chemical compound CCOC(C)COC(C)COC(C)=O CKCGJBFTCUCBAJ-UHFFFAOYSA-N 0.000 description 1
- ZKCAGDPACLOVBN-UHFFFAOYSA-N 2-(2-ethylbutoxy)ethanol Chemical compound CCC(CC)COCCO ZKCAGDPACLOVBN-UHFFFAOYSA-N 0.000 description 1
- GZMAAYIALGURDQ-UHFFFAOYSA-N 2-(2-hexoxyethoxy)ethanol Chemical compound CCCCCCOCCOCCO GZMAAYIALGURDQ-UHFFFAOYSA-N 0.000 description 1
- SBASXUCJHJRPEV-UHFFFAOYSA-N 2-(2-methoxyethoxy)ethanol Chemical compound COCCOCCO SBASXUCJHJRPEV-UHFFFAOYSA-N 0.000 description 1
- BJINVQNEBGOMCR-UHFFFAOYSA-N 2-(2-methoxyethoxy)ethyl acetate Chemical compound COCCOCCOC(C)=O BJINVQNEBGOMCR-UHFFFAOYSA-N 0.000 description 1
- DRLRGHZJOQGQEC-UHFFFAOYSA-N 2-(2-methoxypropoxy)propyl acetate Chemical compound COC(C)COC(C)COC(C)=O DRLRGHZJOQGQEC-UHFFFAOYSA-N 0.000 description 1
- DJCYDDALXPHSHR-UHFFFAOYSA-N 2-(2-propoxyethoxy)ethanol Chemical compound CCCOCCOCCO DJCYDDALXPHSHR-UHFFFAOYSA-N 0.000 description 1
- XYVAYAJYLWYJJN-UHFFFAOYSA-N 2-(2-propoxypropoxy)propan-1-ol Chemical compound CCCOC(C)COC(C)CO XYVAYAJYLWYJJN-UHFFFAOYSA-N 0.000 description 1
- ZDVZUTSFCLMPMB-UHFFFAOYSA-M 2-(3-bicyclo[2.2.1]heptanyl)-1,1,2,2-tetrafluoroethanesulfonate;(4-cyclohexylphenyl)-diphenylsulfanium Chemical compound C1CC2C(C(F)(F)C(F)(F)S(=O)(=O)[O-])CC1C2.C1CCCCC1C1=CC=C([S+](C=2C=CC=CC=2)C=2C=CC=CC=2)C=C1 ZDVZUTSFCLMPMB-UHFFFAOYSA-M 0.000 description 1
- CIEPNGYYAZJVPI-UHFFFAOYSA-M 2-(3-bicyclo[2.2.1]heptanyl)-1,1,2,2-tetrafluoroethanesulfonate;(4-methylsulfonylphenyl)-diphenylsulfanium Chemical compound C1CC2C(C(F)(F)C(F)(F)S(=O)(=O)[O-])CC1C2.C1=CC(S(=O)(=O)C)=CC=C1[S+](C=1C=CC=CC=1)C1=CC=CC=C1 CIEPNGYYAZJVPI-UHFFFAOYSA-M 0.000 description 1
- CDSOWTBAXZQSFF-UHFFFAOYSA-M 2-(3-bicyclo[2.2.1]heptanyl)-1,1,2,2-tetrafluoroethanesulfonate;1-(4-butoxynaphthalen-1-yl)thiolan-1-ium Chemical compound C1CC2C(C(F)(F)C(F)(F)S(=O)(=O)[O-])CC1C2.C12=CC=CC=C2C(OCCCC)=CC=C1[S+]1CCCC1 CDSOWTBAXZQSFF-UHFFFAOYSA-M 0.000 description 1
- COAPLGOCHZYBCI-UHFFFAOYSA-M 2-(3-bicyclo[2.2.1]heptanyl)-1,1,2,2-tetrafluoroethanesulfonate;1-(6-butoxynaphthalen-2-yl)thiolan-1-ium Chemical compound C1CC2C(C(F)(F)C(F)(F)S(=O)(=O)[O-])CC1C2.C1=CC2=CC(OCCCC)=CC=C2C=C1[S+]1CCCC1 COAPLGOCHZYBCI-UHFFFAOYSA-M 0.000 description 1
- JDUWLFYXEJGUET-UHFFFAOYSA-N 2-(3-bicyclo[2.2.1]heptanyl)-1,1,2,2-tetrafluoroethanesulfonate;2,6-dimethyl-4-(thiolan-1-ium-1-yl)phenol Chemical compound CC1=C(O)C(C)=CC([S+]2CCCC2)=C1.C1CC2C(C(F)(F)C(F)(F)S(=O)(=O)[O-])CC1C2 JDUWLFYXEJGUET-UHFFFAOYSA-N 0.000 description 1
- NIKOMHHZILSBRS-UHFFFAOYSA-M 2-(3-bicyclo[2.2.1]heptanyl)-1,1,2,2-tetrafluoroethanesulfonate;bis(4-tert-butylphenyl)iodanium Chemical compound C1CC2C(C(F)(F)C(F)(F)S(=O)(=O)[O-])CC1C2.C1=CC(C(C)(C)C)=CC=C1[I+]C1=CC=C(C(C)(C)C)C=C1 NIKOMHHZILSBRS-UHFFFAOYSA-M 0.000 description 1
- FUARBSGJOAXCCL-UHFFFAOYSA-M 2-(3-bicyclo[2.2.1]heptanyl)-1,1,2,2-tetrafluoroethanesulfonate;diphenyliodanium Chemical compound C=1C=CC=CC=1[I+]C1=CC=CC=C1.C1CC2C(C(F)(F)C(F)(F)S(=O)(=O)[O-])CC1C2 FUARBSGJOAXCCL-UHFFFAOYSA-M 0.000 description 1
- SPBNQWDOUKTPIC-UHFFFAOYSA-M 2-(3-bicyclo[2.2.1]heptanyl)-1,1,2,2-tetrafluoroethanesulfonate;triphenylsulfanium Chemical compound C1CC2C(C(F)(F)C(F)(F)S(=O)(=O)[O-])CC1C2.C1=CC=CC=C1[S+](C=1C=CC=CC=1)C1=CC=CC=C1 SPBNQWDOUKTPIC-UHFFFAOYSA-M 0.000 description 1
- RWLALWYNXFYRGW-UHFFFAOYSA-N 2-Ethyl-1,3-hexanediol Chemical compound CCCC(O)C(CC)CO RWLALWYNXFYRGW-UHFFFAOYSA-N 0.000 description 1
- HQLKZWRSOHTERR-UHFFFAOYSA-N 2-Ethylbutyl acetate Chemical compound CCC(CC)COC(C)=O HQLKZWRSOHTERR-UHFFFAOYSA-N 0.000 description 1
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 1
- PTTPXKJBFFKCEK-UHFFFAOYSA-N 2-Methyl-4-heptanone Chemical compound CC(C)CC(=O)CC(C)C PTTPXKJBFFKCEK-UHFFFAOYSA-N 0.000 description 1
- GQKZRWSUJHVIPE-UHFFFAOYSA-N 2-Pentanol acetate Chemical compound CCCC(C)OC(C)=O GQKZRWSUJHVIPE-UHFFFAOYSA-N 0.000 description 1
- SPSNALDHELHFIJ-UHFFFAOYSA-N 2-[(1-cyano-1-cyclopropylethyl)diazenyl]-2-cyclopropylpropanenitrile Chemical compound C1CC1C(C)(C#N)N=NC(C)(C#N)C1CC1 SPSNALDHELHFIJ-UHFFFAOYSA-N 0.000 description 1
- PFHOSZAOXCYAGJ-UHFFFAOYSA-N 2-[(2-cyano-4-methoxy-4-methylpentan-2-yl)diazenyl]-4-methoxy-2,4-dimethylpentanenitrile Chemical compound COC(C)(C)CC(C)(C#N)N=NC(C)(C#N)CC(C)(C)OC PFHOSZAOXCYAGJ-UHFFFAOYSA-N 0.000 description 1
- WYGWHHGCAGTUCH-UHFFFAOYSA-N 2-[(2-cyano-4-methylpentan-2-yl)diazenyl]-2,4-dimethylpentanenitrile Chemical compound CC(C)CC(C)(C#N)N=NC(C)(C#N)CC(C)C WYGWHHGCAGTUCH-UHFFFAOYSA-N 0.000 description 1
- LCZVSXRMYJUNFX-UHFFFAOYSA-N 2-[2-(2-hydroxypropoxy)propoxy]propan-1-ol Chemical compound CC(O)COC(C)COC(C)CO LCZVSXRMYJUNFX-UHFFFAOYSA-N 0.000 description 1
- SDHQGBWMLCBNSM-UHFFFAOYSA-N 2-[2-(2-methoxyethoxy)ethoxy]ethyl acetate Chemical compound COCCOCCOCCOC(C)=O SDHQGBWMLCBNSM-UHFFFAOYSA-N 0.000 description 1
- JTXMVXSTHSMVQF-UHFFFAOYSA-N 2-acetyloxyethyl acetate Chemical compound CC(=O)OCCOC(C)=O JTXMVXSTHSMVQF-UHFFFAOYSA-N 0.000 description 1
- POAOYUHQDCAZBD-UHFFFAOYSA-N 2-butoxyethanol Chemical compound CCCCOCCO POAOYUHQDCAZBD-UHFFFAOYSA-N 0.000 description 1
- ZVUNTIMPQCQCAQ-UHFFFAOYSA-N 2-dodecanoyloxyethyl dodecanoate Chemical compound CCCCCCCCCCCC(=O)OCCOC(=O)CCCCCCCCCCC ZVUNTIMPQCQCAQ-UHFFFAOYSA-N 0.000 description 1
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 1
- SVONRAPFKPVNKG-UHFFFAOYSA-N 2-ethoxyethyl acetate Chemical compound CCOCCOC(C)=O SVONRAPFKPVNKG-UHFFFAOYSA-N 0.000 description 1
- TZYRSLHNPKPEFV-UHFFFAOYSA-N 2-ethyl-1-butanol Chemical compound CCC(CC)CO TZYRSLHNPKPEFV-UHFFFAOYSA-N 0.000 description 1
- WOYWLLHHWAMFCB-UHFFFAOYSA-N 2-ethylhexyl acetate Chemical compound CCCCC(CC)COC(C)=O WOYWLLHHWAMFCB-UHFFFAOYSA-N 0.000 description 1
- CETWDUZRCINIHU-UHFFFAOYSA-N 2-heptanol Chemical compound CCCCCC(C)O CETWDUZRCINIHU-UHFFFAOYSA-N 0.000 description 1
- UPGSWASWQBLSKZ-UHFFFAOYSA-N 2-hexoxyethanol Chemical compound CCCCCCOCCO UPGSWASWQBLSKZ-UHFFFAOYSA-N 0.000 description 1
- PFNHSEQQEPMLNI-UHFFFAOYSA-N 2-methyl-1-pentanol Chemical compound CCCC(C)CO PFNHSEQQEPMLNI-UHFFFAOYSA-N 0.000 description 1
- MSXVEPNJUHWQHW-UHFFFAOYSA-N 2-methylbutan-2-ol Chemical compound CCC(C)(C)O MSXVEPNJUHWQHW-UHFFFAOYSA-N 0.000 description 1
- ZPVFWPFBNIEHGJ-UHFFFAOYSA-N 2-octanone Chemical compound CCCCCCC(C)=O ZPVFWPFBNIEHGJ-UHFFFAOYSA-N 0.000 description 1
- QCDWFXQBSFUVSP-UHFFFAOYSA-N 2-phenoxyethanol Chemical compound OCCOC1=CC=CC=C1 QCDWFXQBSFUVSP-UHFFFAOYSA-N 0.000 description 1
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
- YEYKMVJDLWJFOA-UHFFFAOYSA-N 2-propoxyethanol Chemical compound CCCOCCO YEYKMVJDLWJFOA-UHFFFAOYSA-N 0.000 description 1
- BRRVXFOKWJKTGG-UHFFFAOYSA-N 3,3,5-trimethylcyclohexanol Chemical compound CC1CC(O)CC(C)(C)C1 BRRVXFOKWJKTGG-UHFFFAOYSA-N 0.000 description 1
- PKNKULBDCRZSBT-UHFFFAOYSA-N 3,4,5-trimethylnonan-2-one Chemical compound CCCCC(C)C(C)C(C)C(C)=O PKNKULBDCRZSBT-UHFFFAOYSA-N 0.000 description 1
- FRIBMENBGGCKPD-UHFFFAOYSA-N 3-(2,3-dimethoxyphenyl)prop-2-enal Chemical compound COC1=CC=CC(C=CC=O)=C1OC FRIBMENBGGCKPD-UHFFFAOYSA-N 0.000 description 1
- QCAHUFWKIQLBNB-UHFFFAOYSA-N 3-(3-methoxypropoxy)propan-1-ol Chemical compound COCCCOCCCO QCAHUFWKIQLBNB-UHFFFAOYSA-N 0.000 description 1
- JSGVZVOGOQILFM-UHFFFAOYSA-N 3-methoxy-1-butanol Chemical compound COC(C)CCO JSGVZVOGOQILFM-UHFFFAOYSA-N 0.000 description 1
- QMYGFTJCQFEDST-UHFFFAOYSA-N 3-methoxybutyl acetate Chemical compound COC(C)CCOC(C)=O QMYGFTJCQFEDST-UHFFFAOYSA-N 0.000 description 1
- YHQXBTXEYZIYOV-UHFFFAOYSA-N 3-methylbut-1-ene Chemical compound CC(C)C=C YHQXBTXEYZIYOV-UHFFFAOYSA-N 0.000 description 1
- LDMRLRNXHLPZJN-UHFFFAOYSA-N 3-propoxypropan-1-ol Chemical compound CCCOCCCO LDMRLRNXHLPZJN-UHFFFAOYSA-N 0.000 description 1
- IICCLYANAQEHCI-UHFFFAOYSA-N 4,5,6,7-tetrachloro-3',6'-dihydroxy-2',4',5',7'-tetraiodospiro[2-benzofuran-3,9'-xanthene]-1-one Chemical compound O1C(=O)C(C(=C(Cl)C(Cl)=C2Cl)Cl)=C2C21C1=CC(I)=C(O)C(I)=C1OC1=C(I)C(O)=C(I)C=C21 IICCLYANAQEHCI-UHFFFAOYSA-N 0.000 description 1
- FUGYGGDSWSUORM-UHFFFAOYSA-N 4-hydroxystyrene Chemical compound OC1=CC=C(C=C)C=C1 FUGYGGDSWSUORM-UHFFFAOYSA-N 0.000 description 1
- WVYWICLMDOOCFB-UHFFFAOYSA-N 4-methyl-2-pentanol Chemical compound CC(C)CC(C)O WVYWICLMDOOCFB-UHFFFAOYSA-N 0.000 description 1
- MQWCXKGKQLNYQG-UHFFFAOYSA-N 4-methylcyclohexan-1-ol Chemical compound CC1CCC(O)CC1 MQWCXKGKQLNYQG-UHFFFAOYSA-N 0.000 description 1
- VGVHNLRUAMRIEW-UHFFFAOYSA-N 4-methylcyclohexan-1-one Chemical compound CC1CCC(=O)CC1 VGVHNLRUAMRIEW-UHFFFAOYSA-N 0.000 description 1
- YRRKZXMKAWXOLN-UHFFFAOYSA-M 6-(adamantane-1-carbonyloxy)-1,1,2,2-tetrafluorohexane-1-sulfonate;triphenylsulfanium Chemical compound C1=CC=CC=C1[S+](C=1C=CC=CC=1)C1=CC=CC=C1.C1C(C2)CC3CC2CC1(C(=O)OCCCCC(F)(F)C(F)(F)S(=O)(=O)[O-])C3 YRRKZXMKAWXOLN-UHFFFAOYSA-M 0.000 description 1
- LPEKGGXMPWTOCB-UHFFFAOYSA-N 8beta-(2,3-epoxy-2-methylbutyryloxy)-14-acetoxytithifolin Natural products COC(=O)C(C)O LPEKGGXMPWTOCB-UHFFFAOYSA-N 0.000 description 1
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- 101100215341 Arabidopsis thaliana ACT12 gene Proteins 0.000 description 1
- 101100434207 Arabidopsis thaliana ACT8 gene Proteins 0.000 description 1
- NOWKCMXCCJGMRR-UHFFFAOYSA-N Aziridine Chemical group C1CN1 NOWKCMXCCJGMRR-UHFFFAOYSA-N 0.000 description 1
- 239000004342 Benzoyl peroxide Substances 0.000 description 1
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 1
- MRABAEUHTLLEML-UHFFFAOYSA-N Butyl lactate Chemical compound CCCCOC(=O)C(C)O MRABAEUHTLLEML-UHFFFAOYSA-N 0.000 description 1
- GNCGIVJMIPBTSD-UHFFFAOYSA-M C.CC.O=C([O-])C1=C(O)C=CC=C1 Chemical compound C.CC.O=C([O-])C1=C(O)C=CC=C1 GNCGIVJMIPBTSD-UHFFFAOYSA-M 0.000 description 1
- MHBOIEWSQQSJFA-UHFFFAOYSA-M C1=CC=C([S+](C2=CC=CC=C2)C2=CC=CC=C2)C=C1.O=S(=O)([O-])CCC12CC3CC(CC(C3)C1)C2 Chemical compound C1=CC=C([S+](C2=CC=CC=C2)C2=CC=CC=C2)C=C1.O=S(=O)([O-])CCC12CC3CC(CC(C3)C1)C2 MHBOIEWSQQSJFA-UHFFFAOYSA-M 0.000 description 1
- RVBPJAVUYFWRPN-UHFFFAOYSA-N C=C(C)C(=O)OC1(CC)C2CC3CC(C2)CC1C3.C=CC1=CC=C(OC(C)=O)C=C1.CC(C)C(=O)OC1C2CC3C(=O)OC1C3C2.CC(C)C(=O)OCC(F)(F)F.CCC1(OC(=O)C(C)C)CCCC1 Chemical compound C=C(C)C(=O)OC1(CC)C2CC3CC(C2)CC1C3.C=CC1=CC=C(OC(C)=O)C=C1.CC(C)C(=O)OC1C2CC3C(=O)OC1C3C2.CC(C)C(=O)OCC(F)(F)F.CCC1(OC(=O)C(C)C)CCCC1 RVBPJAVUYFWRPN-UHFFFAOYSA-N 0.000 description 1
- JCGJDXUQYSAXKL-UHFFFAOYSA-N C=C(NC(C)C)C1CCN(C(=O)OC(C)(C)C)CC1.CCC(C)(C)OC(=O)N1CCC(NS(C)(=O)=O)CC1.CNS(=O)(=O)OC1CCN(C(=O)OC(C)(C)C(C)C)CC1.COS(=O)(=O)NC1CCN(C(=O)OC2CCCC2)CC1 Chemical compound C=C(NC(C)C)C1CCN(C(=O)OC(C)(C)C)CC1.CCC(C)(C)OC(=O)N1CCC(NS(C)(=O)=O)CC1.CNS(=O)(=O)OC1CCN(C(=O)OC(C)(C)C(C)C)CC1.COS(=O)(=O)NC1CCN(C(=O)OC2CCCC2)CC1 JCGJDXUQYSAXKL-UHFFFAOYSA-N 0.000 description 1
- ZBYUAASYERJWJK-UHFFFAOYSA-N CC(C)(C)OC(=O)N1CCC(OC(=O)C2CC3CCC2C3)CC1.CC(C)OC1CCN(C(=O)OC(C)(C)C)CC1.CCC(C)(C)OC(=O)N1CCC(OS(=O)(=O)CC23CCC(CC2=O)C3(C)C)CC1 Chemical compound CC(C)(C)OC(=O)N1CCC(OC(=O)C2CC3CCC2C3)CC1.CC(C)OC1CCN(C(=O)OC(C)(C)C)CC1.CCC(C)(C)OC(=O)N1CCC(OS(=O)(=O)CC23CCC(CC2=O)C3(C)C)CC1 ZBYUAASYERJWJK-UHFFFAOYSA-N 0.000 description 1
- YUBXMPSGZVFSRA-UHFFFAOYSA-N CC(C)(C)OC(=O)NC1CCC(C(=O)C2CCC(NC(=O)OC(C)(C)C)CC2)CC1.CCC(C)(C)OC(=O)N(CCC1CCOCC1)C(C)C.CCC(C)(C)OC(=O)N1C(C)C(C)OC(C)C1C.COCC1CN(C(=O)OC(C)(C)C)C(COC)CN1C(=O)OC(C)(C)C Chemical compound CC(C)(C)OC(=O)NC1CCC(C(=O)C2CCC(NC(=O)OC(C)(C)C)CC2)CC1.CCC(C)(C)OC(=O)N(CCC1CCOCC1)C(C)C.CCC(C)(C)OC(=O)N1C(C)C(C)OC(C)C1C.COCC1CN(C(=O)OC(C)(C)C)C(COC)CN1C(=O)OC(C)(C)C YUBXMPSGZVFSRA-UHFFFAOYSA-N 0.000 description 1
- FGQAXXMGWDREMY-UHFFFAOYSA-N CC(C)C1(C)CC2(CC(O)CC(O)C2)OC1=O.CC(C)C1(C)CC2(CCC(O)C2)OC1=O.CC(C)C1(C)CC2(CCC(O)CC2)OC1=O.CCC(C)(C)C(=O)OC1C2CC3C1OS(=O)(=O)C3(C#N)C2.CCC(C)(C)C(=O)OC1C2CC3C1OS(=O)(=O)C3(C(F)(F)F)C2.CCC(C)(C)C(=O)OC1C2CC3C1OS(=O)(=O)C3C2.CCC(C)(C)C(=O)OC1C2CC3C1OS(=O)(=O)C3C2C(=O)OC.CCC(C)(C)C(=O)OCC(=O)OC1C2CC3C1OS(=O)(=O)C3C2.CCC(C)(C)C(=O)OCC1OC(=O)OC2C1OC1OC(C)(C)OC12.CCC(C)(C)C(=O)OCCOC1C2CC3C1OS(=O)(=O)C3C2 Chemical compound CC(C)C1(C)CC2(CC(O)CC(O)C2)OC1=O.CC(C)C1(C)CC2(CCC(O)C2)OC1=O.CC(C)C1(C)CC2(CCC(O)CC2)OC1=O.CCC(C)(C)C(=O)OC1C2CC3C1OS(=O)(=O)C3(C#N)C2.CCC(C)(C)C(=O)OC1C2CC3C1OS(=O)(=O)C3(C(F)(F)F)C2.CCC(C)(C)C(=O)OC1C2CC3C1OS(=O)(=O)C3C2.CCC(C)(C)C(=O)OC1C2CC3C1OS(=O)(=O)C3C2C(=O)OC.CCC(C)(C)C(=O)OCC(=O)OC1C2CC3C1OS(=O)(=O)C3C2.CCC(C)(C)C(=O)OCC1OC(=O)OC2C1OC1OC(C)(C)OC12.CCC(C)(C)C(=O)OCCOC1C2CC3C1OS(=O)(=O)C3C2 FGQAXXMGWDREMY-UHFFFAOYSA-N 0.000 description 1
- ZNNYUQWBDKGPKF-UHFFFAOYSA-N CC(C)N(C(C)C)C1CCN(C(=O)OC(C)(C)C)CC1.CCC(C)(C)OC(=O)N1CCC(C(=O)OC2CCCCC2)CC1.CCN(CC)C1CCN(C(=O)OC23CC4CC(CC(C4)C2)C3)C1 Chemical compound CC(C)N(C(C)C)C1CCN(C(=O)OC(C)(C)C)CC1.CCC(C)(C)OC(=O)N1CCC(C(=O)OC2CCCCC2)CC1.CCN(CC)C1CCN(C(=O)OC23CC4CC(CC(C4)C2)C3)C1 ZNNYUQWBDKGPKF-UHFFFAOYSA-N 0.000 description 1
- BSDXRSALDBDUCM-UHFFFAOYSA-N CC(C)OCN(COC(C)C)C(=O)OC(C)(C)C.CCC(C)(C)OC(=O)N1CCC(NC(=O)C(C)(C)C)CC1.CCOC(=O)C1CCC(NC(=O)OC(CC)(CC)CC)CC1.COC1CCC(N(C(=O)OC2CCCCC2)C2CCC(OC)CC2)CC1 Chemical compound CC(C)OCN(COC(C)C)C(=O)OC(C)(C)C.CCC(C)(C)OC(=O)N1CCC(NC(=O)C(C)(C)C)CC1.CCOC(=O)C1CCC(NC(=O)OC(CC)(CC)CC)CC1.COC1CCC(N(C(=O)OC2CCCCC2)C2CCC(OC)CC2)CC1 BSDXRSALDBDUCM-UHFFFAOYSA-N 0.000 description 1
- FEZLBWWYEDEJOQ-UHFFFAOYSA-N CCC(C)(C)C(=O)OC1(C)CCOC1=O.CCC(C)(C)C(=O)OC1(C)COC(=O)C1.CCC(C)(C)C(=O)OC1COC(=O)C1.CCC(C)(C)C(=O)OCC(=O)OCC1COC(=O)O1.CCC(C)(C)C(=O)OCC1(C)COC(=O)O1.CCC(C)(C)C(=O)OCC1COC(=O)O1.CCC(C)(C)C(=O)OCC1OC(=O)OC1CO.CCC(C)(C)C(=O)OCCCC1COC(=O)O1.CCC(C)(C)C(=O)OCCCCCC1COC(=O)O1.CCC(C)(C)C(=O)OCCOCC1COC(=O)O1.CCC1(OC(=O)C(C)(C)CC)COC(=O)C1.CCCCCC1OC(=O)OC1COC(=O)C(C)(C)CC Chemical compound CCC(C)(C)C(=O)OC1(C)CCOC1=O.CCC(C)(C)C(=O)OC1(C)COC(=O)C1.CCC(C)(C)C(=O)OC1COC(=O)C1.CCC(C)(C)C(=O)OCC(=O)OCC1COC(=O)O1.CCC(C)(C)C(=O)OCC1(C)COC(=O)O1.CCC(C)(C)C(=O)OCC1COC(=O)O1.CCC(C)(C)C(=O)OCC1OC(=O)OC1CO.CCC(C)(C)C(=O)OCCCC1COC(=O)O1.CCC(C)(C)C(=O)OCCCCCC1COC(=O)O1.CCC(C)(C)C(=O)OCCOCC1COC(=O)O1.CCC1(OC(=O)C(C)(C)CC)COC(=O)C1.CCCCCC1OC(=O)OC1COC(=O)C(C)(C)CC FEZLBWWYEDEJOQ-UHFFFAOYSA-N 0.000 description 1
- RBQXTNZXNMUMSI-UHFFFAOYSA-N CCC(C)(C)C(=O)OC1C2CC(C1OC)C1C(=O)OCC21.CCC(C)(C)C(=O)OC1C2CC3C(=O)OC1C3C2.CCC(C)(C)C(=O)OC1C2CC3C1OC(=O)C3(C#N)C2.CCC(C)(C)C(=O)OC1C2CC3C1OC(=O)C3(C(F)(F)F)C2.CCC(C)(C)C(=O)OC1C2CC3C1OC(=O)C3C2C(=O)OC.CCC(C)(C)C(=O)OCC(=O)OC1C2CC3C(=O)OC1C3C2.CCC(C)(C)C(=O)OCCOC(=O)CC(=O)OC1C2CC3C(=O)OC1C3C2.CCC(C)(C)C(=O)OCCOC1C2CC3C(=O)OC1C3C2 Chemical compound CCC(C)(C)C(=O)OC1C2CC(C1OC)C1C(=O)OCC21.CCC(C)(C)C(=O)OC1C2CC3C(=O)OC1C3C2.CCC(C)(C)C(=O)OC1C2CC3C1OC(=O)C3(C#N)C2.CCC(C)(C)C(=O)OC1C2CC3C1OC(=O)C3(C(F)(F)F)C2.CCC(C)(C)C(=O)OC1C2CC3C1OC(=O)C3C2C(=O)OC.CCC(C)(C)C(=O)OCC(=O)OC1C2CC3C(=O)OC1C3C2.CCC(C)(C)C(=O)OCCOC(=O)CC(=O)OC1C2CC3C(=O)OC1C3C2.CCC(C)(C)C(=O)OCCOC1C2CC3C(=O)OC1C3C2 RBQXTNZXNMUMSI-UHFFFAOYSA-N 0.000 description 1
- RFDGBHFTUQGJHF-UHFFFAOYSA-N CCC(C)(C)C(=O)OC1C2CC3C(O2)C1OS3(=O)=O.CCC(C)(C)C(=O)OC1C2CCCC2OS1(=O)=O.CCC(C)(C)C(=O)OC1CCC2CC1OS2(=O)=O.CCC(C)(C)C(=O)OC1COS(=O)(=O)C1.CCC(C)(C)C(=O)OCCOC(=O)CC(=O)OC1C2CC3C1OS(=O)(=O)C3C2 Chemical compound CCC(C)(C)C(=O)OC1C2CC3C(O2)C1OS3(=O)=O.CCC(C)(C)C(=O)OC1C2CCCC2OS1(=O)=O.CCC(C)(C)C(=O)OC1CCC2CC1OS2(=O)=O.CCC(C)(C)C(=O)OC1COS(=O)(=O)C1.CCC(C)(C)C(=O)OCCOC(=O)CC(=O)OC1C2CC3C1OS(=O)(=O)C3C2 RFDGBHFTUQGJHF-UHFFFAOYSA-N 0.000 description 1
- OCCLMLOQEWBKJG-UHFFFAOYSA-N CCC(C)(C)C(=O)OC1CC2CC1OC(=O)O2.CCC(C)(C)C(=O)OCC(OCC1=CC=CC=C1)C1COC(=O)O1.CCC(C)(C)C(=O)OCC1(C)OC(=O)OC1N(C)C.CCC(C)(C)C(=O)OCC1C2CC(OC(=O)O2)C1C.CCC(C)(C)C(=O)OCC1CCC2OC(=O)OC2C1.CCC(C)(C)C(=O)OCC1OC(=O)OC1C(=O)OC.CCC(C)(C)C(=O)OCCOC(=O)CC(=O)OCC1OC(=O)OC1OC.[C-]#[N+]C1OC(=O)OC1COC(=O)C(C)(C)CC Chemical compound CCC(C)(C)C(=O)OC1CC2CC1OC(=O)O2.CCC(C)(C)C(=O)OCC(OCC1=CC=CC=C1)C1COC(=O)O1.CCC(C)(C)C(=O)OCC1(C)OC(=O)OC1N(C)C.CCC(C)(C)C(=O)OCC1C2CC(OC(=O)O2)C1C.CCC(C)(C)C(=O)OCC1CCC2OC(=O)OC2C1.CCC(C)(C)C(=O)OCC1OC(=O)OC1C(=O)OC.CCC(C)(C)C(=O)OCCOC(=O)CC(=O)OCC1OC(=O)OC1OC.[C-]#[N+]C1OC(=O)OC1COC(=O)C(C)(C)CC OCCLMLOQEWBKJG-UHFFFAOYSA-N 0.000 description 1
- JGKMTOURVSWBAP-UHFFFAOYSA-N CCC(C)(C)OC(=O)N1CCC(OS(=O)(=O)C23CCC(CC2=O)C3(C)C)CC1 Chemical compound CCC(C)(C)OC(=O)N1CCC(OS(=O)(=O)C23CCC(CC2=O)C3(C)C)CC1 JGKMTOURVSWBAP-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- PMPVIKIVABFJJI-UHFFFAOYSA-N Cyclobutane Chemical compound C1CCC1 PMPVIKIVABFJJI-UHFFFAOYSA-N 0.000 description 1
- YYLLIJHXUHJATK-UHFFFAOYSA-N Cyclohexyl acetate Chemical compound CC(=O)OC1CCCCC1 YYLLIJHXUHJATK-UHFFFAOYSA-N 0.000 description 1
- LVZWSLJZHVFIQJ-UHFFFAOYSA-N Cyclopropane Chemical compound C1CC1 LVZWSLJZHVFIQJ-UHFFFAOYSA-N 0.000 description 1
- QSJXEFYPDANLFS-UHFFFAOYSA-N Diacetyl Chemical group CC(=O)C(C)=O QSJXEFYPDANLFS-UHFFFAOYSA-N 0.000 description 1
- OIFBSDVPJOWBCH-UHFFFAOYSA-N Diethyl carbonate Chemical compound CCOC(=O)OCC OIFBSDVPJOWBCH-UHFFFAOYSA-N 0.000 description 1
- HXQPUEQDBSPXTE-UHFFFAOYSA-N Diisobutylcarbinol Chemical compound CC(C)CC(O)CC(C)C HXQPUEQDBSPXTE-UHFFFAOYSA-N 0.000 description 1
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- KMTRUDSVKNLOMY-UHFFFAOYSA-N Ethylene carbonate Chemical compound O=C1OCCO1 KMTRUDSVKNLOMY-UHFFFAOYSA-N 0.000 description 1
- FPVVYTCTZKCSOJ-UHFFFAOYSA-N Ethylene glycol distearate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCCOC(=O)CCCCCCCCCCCCCCCCC FPVVYTCTZKCSOJ-UHFFFAOYSA-N 0.000 description 1
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 1
- RJUFJBKOKNCXHH-UHFFFAOYSA-N Methyl propionate Chemical compound CCC(=O)OC RJUFJBKOKNCXHH-UHFFFAOYSA-N 0.000 description 1
- WRQNANDWMGAFTP-UHFFFAOYSA-N Methylacetoacetic acid Chemical compound COC(=O)CC(C)=O WRQNANDWMGAFTP-UHFFFAOYSA-N 0.000 description 1
- MGJKQDOBUOMPEZ-UHFFFAOYSA-N N,N'-dimethylurea Chemical compound CNC(=O)NC MGJKQDOBUOMPEZ-UHFFFAOYSA-N 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
- SUAKHGWARZSWIH-UHFFFAOYSA-N N,N‐diethylformamide Chemical compound CCN(CC)C=O SUAKHGWARZSWIH-UHFFFAOYSA-N 0.000 description 1
- XGEGHDBEHXKFPX-UHFFFAOYSA-N N-methylthiourea Natural products CNC(N)=O XGEGHDBEHXKFPX-UHFFFAOYSA-N 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- JKRZOJADNVOXPM-UHFFFAOYSA-N Oxalic acid dibutyl ester Chemical compound CCCCOC(=O)C(=O)OCCCC JKRZOJADNVOXPM-UHFFFAOYSA-N 0.000 description 1
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 1
- 229920002873 Polyethylenimine Polymers 0.000 description 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 1
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 description 1
- OUUQCZGPVNCOIJ-UHFFFAOYSA-M Superoxide Chemical compound [O-][O] OUUQCZGPVNCOIJ-UHFFFAOYSA-M 0.000 description 1
- DHXVGJBLRPWPCS-UHFFFAOYSA-N Tetrahydropyran Chemical compound C1CCOCC1 DHXVGJBLRPWPCS-UHFFFAOYSA-N 0.000 description 1
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- FLRQOWAOMJMSTP-JJTRIOAGSA-N [(2s)-2-[(2r)-3,4-dihydroxy-5-oxo-2h-furan-2-yl]-2-hydroxyethyl] (6z,9z,12z)-octadeca-6,9,12-trienoate Chemical compound CCCCC\C=C/C\C=C/C\C=C/CCCCC(=O)OC[C@H](O)[C@H]1OC(=O)C(O)=C1O FLRQOWAOMJMSTP-JJTRIOAGSA-N 0.000 description 1
- NVJPBZCLWGTJKD-UHFFFAOYSA-N [bis(4-tert-butylphenyl)-lambda3-iodanyl] trifluoromethanesulfonate Chemical compound CC(C)(C)c1ccc(cc1)[I](OS(=O)(=O)C(F)(F)F)c1ccc(cc1)C(C)(C)C NVJPBZCLWGTJKD-UHFFFAOYSA-N 0.000 description 1
- KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 description 1
- 150000008062 acetophenones Chemical class 0.000 description 1
- JIMXXGFJRDUSRO-UHFFFAOYSA-N adamantane-1-carboxylic acid Chemical compound C1C(C2)CC3CC2CC1(C(=O)O)C3 JIMXXGFJRDUSRO-UHFFFAOYSA-N 0.000 description 1
- IYKFYARMMIESOX-UHFFFAOYSA-N adamantanone Chemical compound C1C(C2)CC3CC1C(=O)C2C3 IYKFYARMMIESOX-UHFFFAOYSA-N 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 125000003342 alkenyl group Chemical group 0.000 description 1
- 150000001345 alkine derivatives Chemical class 0.000 description 1
- 125000005078 alkoxycarbonylalkyl group Chemical group 0.000 description 1
- 125000000304 alkynyl group Chemical group 0.000 description 1
- 230000005260 alpha ray Effects 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 1
- 150000001450 anions Chemical class 0.000 description 1
- 150000001454 anthracenes Chemical class 0.000 description 1
- 150000004982 aromatic amines Chemical class 0.000 description 1
- VJEIIJANCJRLFJ-UHFFFAOYSA-N azecane Chemical group C1CCCCNCCCC1 VJEIIJANCJRLFJ-UHFFFAOYSA-N 0.000 description 1
- ZSIQJIWKELUFRJ-UHFFFAOYSA-N azepane Chemical group C1CCCNCC1 ZSIQJIWKELUFRJ-UHFFFAOYSA-N 0.000 description 1
- HONIICLYMWZJFZ-UHFFFAOYSA-N azetidine Chemical group C1CNC1 HONIICLYMWZJFZ-UHFFFAOYSA-N 0.000 description 1
- QXNDZONIWRINJR-UHFFFAOYSA-N azocane Chemical group C1CCCNCCC1 QXNDZONIWRINJR-UHFFFAOYSA-N 0.000 description 1
- 239000011324 bead Substances 0.000 description 1
- 239000012965 benzophenone Substances 0.000 description 1
- 150000008366 benzophenones Chemical class 0.000 description 1
- 235000019400 benzoyl peroxide Nutrition 0.000 description 1
- 229940007550 benzyl acetate Drugs 0.000 description 1
- 235000019445 benzyl alcohol Nutrition 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- GPRLTFBKWDERLU-UHFFFAOYSA-N bicyclo[2.2.2]octane Chemical group C1CC2CCC1CC2 GPRLTFBKWDERLU-UHFFFAOYSA-N 0.000 description 1
- DNFSNYQTQMVTOK-UHFFFAOYSA-N bis(4-tert-butylphenyl)iodanium Chemical compound C1=CC(C(C)(C)C)=CC=C1[I+]C1=CC=C(C(C)(C)C)C=C1 DNFSNYQTQMVTOK-UHFFFAOYSA-N 0.000 description 1
- MDUKBVGQQFOMPC-UHFFFAOYSA-M bis(4-tert-butylphenyl)iodanium;(7,7-dimethyl-3-oxo-4-bicyclo[2.2.1]heptanyl)methanesulfonate Chemical compound C1CC2(CS([O-])(=O)=O)C(=O)CC1C2(C)C.C1=CC(C(C)(C)C)=CC=C1[I+]C1=CC=C(C(C)(C)C)C=C1 MDUKBVGQQFOMPC-UHFFFAOYSA-M 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
- 239000001273 butane Substances 0.000 description 1
- 235000019437 butane-1,3-diol Nutrition 0.000 description 1
- 125000004369 butenyl group Chemical group C(=CCC)* 0.000 description 1
- BTMVHUNTONAYDX-UHFFFAOYSA-N butyl propionate Chemical compound CCCCOC(=O)CC BTMVHUNTONAYDX-UHFFFAOYSA-N 0.000 description 1
- 125000000480 butynyl group Chemical group [*]C#CC([H])([H])C([H])([H])[H] 0.000 description 1
- 150000001716 carbazoles Chemical class 0.000 description 1
- 150000001733 carboxylic acid esters Chemical class 0.000 description 1
- UOCJDOLVGGIYIQ-PBFPGSCMSA-N cefatrizine Chemical group S([C@@H]1[C@@H](C(N1C=1C(O)=O)=O)NC(=O)[C@H](N)C=2C=CC(O)=CC=2)CC=1CSC=1C=NNN=1 UOCJDOLVGGIYIQ-PBFPGSCMSA-N 0.000 description 1
- OEYIOHPDSNJKLS-UHFFFAOYSA-N choline Chemical compound C[N+](C)(C)CCO OEYIOHPDSNJKLS-UHFFFAOYSA-N 0.000 description 1
- 229960001231 choline Drugs 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 238000006482 condensation reaction Methods 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 125000006165 cyclic alkyl group Chemical group 0.000 description 1
- 150000003950 cyclic amides Chemical class 0.000 description 1
- 150000001924 cycloalkanes Chemical class 0.000 description 1
- CFBGXYDUODCMNS-UHFFFAOYSA-N cyclobutene Chemical compound C1CC=C1 CFBGXYDUODCMNS-UHFFFAOYSA-N 0.000 description 1
- UCIYGNATMHQYCT-OWOJBTEDSA-N cyclodecene Chemical compound C1CCCC\C=C\CCC1 UCIYGNATMHQYCT-OWOJBTEDSA-N 0.000 description 1
- CGZZMOTZOONQIA-UHFFFAOYSA-N cycloheptanone Chemical compound O=C1CCCCCC1 CGZZMOTZOONQIA-UHFFFAOYSA-N 0.000 description 1
- 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 description 1
- 125000000596 cyclohexenyl group Chemical group C1(=CCCCC1)* 0.000 description 1
- IIRFCWANHMSDCG-UHFFFAOYSA-N cyclooctanone Chemical compound O=C1CCCCCCC1 IIRFCWANHMSDCG-UHFFFAOYSA-N 0.000 description 1
- URYYVOIYTNXXBN-UPHRSURJSA-N cyclooctene Chemical compound C1CCC\C=C/CC1 URYYVOIYTNXXBN-UPHRSURJSA-N 0.000 description 1
- 239000004913 cyclooctene Substances 0.000 description 1
- 125000002433 cyclopentenyl group Chemical group C1(=CCCC1)* 0.000 description 1
- OOXWYYGXTJLWHA-UHFFFAOYSA-N cyclopropene Chemical compound C1C=C1 OOXWYYGXTJLWHA-UHFFFAOYSA-N 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- DIOQZVSQGTUSAI-NJFSPNSNSA-N decane Chemical group CCCCCCCCC[14CH3] DIOQZVSQGTUSAI-NJFSPNSNSA-N 0.000 description 1
- 230000006735 deficit Effects 0.000 description 1
- KXGVEGMKQFWNSR-LLQZFEROSA-N deoxycholic acid Chemical class C([C@H]1CC2)[C@H](O)CC[C@]1(C)[C@@H]1[C@@H]2[C@@H]2CC[C@H]([C@@H](CCC(O)=O)C)[C@@]2(C)[C@@H](O)C1 KXGVEGMKQFWNSR-LLQZFEROSA-N 0.000 description 1
- 230000002542 deteriorative effect Effects 0.000 description 1
- 125000005265 dialkylamine group Chemical group 0.000 description 1
- 150000001983 dialkylethers Chemical class 0.000 description 1
- 239000012954 diazonium Substances 0.000 description 1
- 150000001989 diazonium salts Chemical class 0.000 description 1
- WYACBZDAHNBPPB-UHFFFAOYSA-N diethyl oxalate Chemical compound CCOC(=O)C(=O)OCC WYACBZDAHNBPPB-UHFFFAOYSA-N 0.000 description 1
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
- 229940028356 diethylene glycol monobutyl ether Drugs 0.000 description 1
- XXJWXESWEXIICW-UHFFFAOYSA-N diethylene glycol monoethyl ether Chemical compound CCOCCOCCO XXJWXESWEXIICW-UHFFFAOYSA-N 0.000 description 1
- 229940075557 diethylene glycol monoethyl ether Drugs 0.000 description 1
- FBSAITBEAPNWJG-UHFFFAOYSA-N dimethyl phthalate Natural products CC(=O)OC1=CC=CC=C1OC(C)=O FBSAITBEAPNWJG-UHFFFAOYSA-N 0.000 description 1
- JVSWJIKNEAIKJW-UHFFFAOYSA-N dimethyl-hexane Natural products CCCCCC(C)C JVSWJIKNEAIKJW-UHFFFAOYSA-N 0.000 description 1
- 229960001826 dimethylphthalate Drugs 0.000 description 1
- OZLBDYMWFAHSOQ-UHFFFAOYSA-N diphenyliodanium Chemical compound C=1C=CC=CC=1[I+]C1=CC=CC=C1 OZLBDYMWFAHSOQ-UHFFFAOYSA-N 0.000 description 1
- ORPDKMPYOLFUBA-UHFFFAOYSA-M diphenyliodanium;1,1,2,2,3,3,4,4,4-nonafluorobutane-1-sulfonate Chemical compound C=1C=CC=CC=1[I+]C1=CC=CC=C1.[O-]S(=O)(=O)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F ORPDKMPYOLFUBA-UHFFFAOYSA-M 0.000 description 1
- SBQIJPBUMNWUKN-UHFFFAOYSA-M diphenyliodanium;trifluoromethanesulfonate Chemical compound [O-]S(=O)(=O)C(F)(F)F.C=1C=CC=CC=1[I+]C1=CC=CC=C1 SBQIJPBUMNWUKN-UHFFFAOYSA-M 0.000 description 1
- POLCUAVZOMRGSN-UHFFFAOYSA-N dipropyl ether Chemical compound CCCOCCC POLCUAVZOMRGSN-UHFFFAOYSA-N 0.000 description 1
- WEHWNAOGRSTTBQ-UHFFFAOYSA-N dipropylamine Chemical compound CCCNCCC WEHWNAOGRSTTBQ-UHFFFAOYSA-N 0.000 description 1
- SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 description 1
- 238000010494 dissociation reaction Methods 0.000 description 1
- 230000005593 dissociations Effects 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 229940052761 dopaminergic adamantane derivative Drugs 0.000 description 1
- ODQWQRRAPPTVAG-GZTJUZNOSA-N doxepin Chemical compound C1OC2=CC=CC=C2C(=C/CCN(C)C)/C2=CC=CC=C21 ODQWQRRAPPTVAG-GZTJUZNOSA-N 0.000 description 1
- 238000001312 dry etching Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- YQGOJNYOYNNSMM-UHFFFAOYSA-N eosin Chemical compound [Na+].OC(=O)C1=CC=CC=C1C1=C2C=C(Br)C(=O)C(Br)=C2OC2=C(Br)C(O)=C(Br)C=C21 YQGOJNYOYNNSMM-UHFFFAOYSA-N 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- XYIBRDXRRQCHLP-UHFFFAOYSA-N ethyl acetoacetate Chemical compound CCOC(=O)CC(C)=O XYIBRDXRRQCHLP-UHFFFAOYSA-N 0.000 description 1
- 229940093858 ethyl acetoacetate Drugs 0.000 description 1
- 229940116333 ethyl lactate Drugs 0.000 description 1
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 230000005251 gamma ray Effects 0.000 description 1
- 235000011187 glycerol Nutrition 0.000 description 1
- 229940100608 glycol distearate Drugs 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- XVEOUOTUJBYHNL-UHFFFAOYSA-N heptane-2,4-diol Chemical compound CCCC(O)CC(C)O XVEOUOTUJBYHNL-UHFFFAOYSA-N 0.000 description 1
- QNVRIHYSUZMSGM-UHFFFAOYSA-N hexan-2-ol Chemical compound CCCCC(C)O QNVRIHYSUZMSGM-UHFFFAOYSA-N 0.000 description 1
- RXTNIJMLAQNTEG-UHFFFAOYSA-N hexan-2-yl acetate Chemical compound CCCCC(C)OC(C)=O RXTNIJMLAQNTEG-UHFFFAOYSA-N 0.000 description 1
- OHMBHFSEKCCCBW-UHFFFAOYSA-N hexane-2,5-diol Chemical compound CC(O)CCC(C)O OHMBHFSEKCCCBW-UHFFFAOYSA-N 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 238000000671 immersion lithography Methods 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 230000001678 irradiating effect Effects 0.000 description 1
- 239000001282 iso-butane Substances 0.000 description 1
- MLFHJEHSLIIPHL-UHFFFAOYSA-N isoamyl acetate Chemical compound CC(C)CCOC(C)=O MLFHJEHSLIIPHL-UHFFFAOYSA-N 0.000 description 1
- PHTQWCKDNZKARW-UHFFFAOYSA-N isoamylol Chemical compound CC(C)CCO PHTQWCKDNZKARW-UHFFFAOYSA-N 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- KXUHSQYYJYAXGZ-UHFFFAOYSA-N isobutylbenzene Chemical compound CC(C)CC1=CC=CC=C1 KXUHSQYYJYAXGZ-UHFFFAOYSA-N 0.000 description 1
- FGKJLKRYENPLQH-UHFFFAOYSA-M isocaproate Chemical compound CC(C)CCC([O-])=O FGKJLKRYENPLQH-UHFFFAOYSA-M 0.000 description 1
- JMMWKPVZQRWMSS-UHFFFAOYSA-N isopropanol acetate Natural products CC(C)OC(C)=O JMMWKPVZQRWMSS-UHFFFAOYSA-N 0.000 description 1
- 229940011051 isopropyl acetate Drugs 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- GWYFCOCPABKNJV-UHFFFAOYSA-M isovalerate Chemical compound CC(C)CC([O-])=O GWYFCOCPABKNJV-UHFFFAOYSA-M 0.000 description 1
- OQAGVSWESNCJJT-UHFFFAOYSA-N isovaleric acid methyl ester Natural products COC(=O)CC(C)C OQAGVSWESNCJJT-UHFFFAOYSA-N 0.000 description 1
- SMEROWZSTRWXGI-HVATVPOCSA-N lithocholic acid Chemical class C([C@H]1CC2)[C@H](O)CC[C@]1(C)[C@@H]1[C@@H]2[C@@H]2CC[C@H]([C@@H](CCC(O)=O)C)[C@@]2(C)CC1 SMEROWZSTRWXGI-HVATVPOCSA-N 0.000 description 1
- 230000001404 mediated effect Effects 0.000 description 1
- AUHZEENZYGFFBQ-UHFFFAOYSA-N mesitylene Substances CC1=CC(C)=CC(C)=C1 AUHZEENZYGFFBQ-UHFFFAOYSA-N 0.000 description 1
- 125000001827 mesitylenyl group Chemical group [H]C1=C(C(*)=C(C([H])=C1C([H])([H])[H])C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- IMXBRVLCKXGWSS-UHFFFAOYSA-N methyl 2-cyclohexylacetate Chemical compound COC(=O)CC1CCCCC1 IMXBRVLCKXGWSS-UHFFFAOYSA-N 0.000 description 1
- GFVQBVDJRHZKPO-UHFFFAOYSA-N methyl 2-hydroxy-5-oxo-4-oxatricyclo[4.2.1.03,7]nonane-9-carboxylate Chemical compound O1C(=O)C2C(C(=O)OC)C3C(O)C1C2C3 GFVQBVDJRHZKPO-UHFFFAOYSA-N 0.000 description 1
- 229940043265 methyl isobutyl ketone Drugs 0.000 description 1
- 229940057867 methyl lactate Drugs 0.000 description 1
- 229940017219 methyl propionate Drugs 0.000 description 1
- GYNNXHKOJHMOHS-UHFFFAOYSA-N methyl-cycloheptane Natural products CC1CCCCCC1 GYNNXHKOJHMOHS-UHFFFAOYSA-N 0.000 description 1
- XGEGHDBEHXKFPX-NJFSPNSNSA-N methylurea Chemical compound [14CH3]NC(N)=O XGEGHDBEHXKFPX-NJFSPNSNSA-N 0.000 description 1
- DAZXVJBJRMWXJP-UHFFFAOYSA-N n,n-dimethylethylamine Chemical compound CCN(C)C DAZXVJBJRMWXJP-UHFFFAOYSA-N 0.000 description 1
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 229940017144 n-butyl lactate Drugs 0.000 description 1
- RCLLINSDAJVOHP-UHFFFAOYSA-N n-ethyl-n',n'-dimethylprop-2-enehydrazide Chemical compound CCN(N(C)C)C(=O)C=C RCLLINSDAJVOHP-UHFFFAOYSA-N 0.000 description 1
- GNVRJGIVDSQCOP-UHFFFAOYSA-N n-ethyl-n-methylethanamine Chemical compound CCN(C)CC GNVRJGIVDSQCOP-UHFFFAOYSA-N 0.000 description 1
- QJQAMHYHNCADNR-UHFFFAOYSA-N n-methylpropanamide Chemical compound CCC(=O)NC QJQAMHYHNCADNR-UHFFFAOYSA-N 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 150000002790 naphthalenes Chemical class 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 239000002736 nonionic surfactant Substances 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
- 125000003518 norbornenyl group Chemical group C12(C=CC(CC1)C2)* 0.000 description 1
- 125000002868 norbornyl group Chemical group C12(CCC(CC1)C2)* 0.000 description 1
- SJWFXCIHNDVPSH-UHFFFAOYSA-N octan-2-ol Chemical compound CCCCCCC(C)O SJWFXCIHNDVPSH-UHFFFAOYSA-N 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- JCGNDDUYTRNOFT-UHFFFAOYSA-N oxolane-2,4-dione Chemical compound O=C1COC(=O)C1 JCGNDDUYTRNOFT-UHFFFAOYSA-N 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- JYVLIDXNZAXMDK-UHFFFAOYSA-N pentan-2-ol Chemical compound CCCC(C)O JYVLIDXNZAXMDK-UHFFFAOYSA-N 0.000 description 1
- GTCCGKPBSJZVRZ-UHFFFAOYSA-N pentane-2,4-diol Chemical compound CC(O)CC(C)O GTCCGKPBSJZVRZ-UHFFFAOYSA-N 0.000 description 1
- YWAKXRMUMFPDSH-UHFFFAOYSA-N pentene Chemical compound CCCC=C YWAKXRMUMFPDSH-UHFFFAOYSA-N 0.000 description 1
- GXOHBWLPQHTYPF-UHFFFAOYSA-N pentyl 2-hydroxypropanoate Chemical compound CCCCCOC(=O)C(C)O GXOHBWLPQHTYPF-UHFFFAOYSA-N 0.000 description 1
- 125000005004 perfluoroethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 description 1
- 125000005005 perfluorohexyl group Chemical group FC(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)* 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 125000001484 phenothiazinyl group Chemical class C1(=CC=CC=2SC3=CC=CC=C3NC12)* 0.000 description 1
- 229960005323 phenoxyethanol Drugs 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 125000004344 phenylpropyl group Chemical group 0.000 description 1
- 150000004714 phosphonium salts Chemical class 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 229920000083 poly(allylamine) Polymers 0.000 description 1
- 229920000768 polyamine Polymers 0.000 description 1
- 230000000379 polymerizing effect Effects 0.000 description 1
- 229920000259 polyoxyethylene lauryl ether Polymers 0.000 description 1
- 239000011148 porous material Substances 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- 125000004368 propenyl group Chemical group C(=CC)* 0.000 description 1
- QLNJFJADRCOGBJ-UHFFFAOYSA-N propionamide Chemical compound CCC(N)=O QLNJFJADRCOGBJ-UHFFFAOYSA-N 0.000 description 1
- 229940080818 propionamide Drugs 0.000 description 1
- RUOJZAUFBMNUDX-UHFFFAOYSA-N propylene carbonate Chemical compound CC1COC(=O)O1 RUOJZAUFBMNUDX-UHFFFAOYSA-N 0.000 description 1
- MWWATHDPGQKSAR-UHFFFAOYSA-N propyne Chemical compound CC#C MWWATHDPGQKSAR-UHFFFAOYSA-N 0.000 description 1
- 125000002568 propynyl group Chemical group [*]C#CC([H])([H])[H] 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 150000003220 pyrenes Chemical class 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 150000003222 pyridines Chemical class 0.000 description 1
- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 description 1
- SBYHFKPVCBCYGV-UHFFFAOYSA-N quinuclidine Chemical group C1CC2CCN1CC2 SBYHFKPVCBCYGV-UHFFFAOYSA-N 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 229940081623 rose bengal Drugs 0.000 description 1
- 229930187593 rose bengal Natural products 0.000 description 1
- STRXNPAVPKGJQR-UHFFFAOYSA-N rose bengal A Natural products O1C(=O)C(C(=CC=C2Cl)Cl)=C2C21C1=CC(I)=C(O)C(I)=C1OC1=C(I)C(O)=C(I)C=C21 STRXNPAVPKGJQR-UHFFFAOYSA-N 0.000 description 1
- 229930195734 saturated hydrocarbon Natural products 0.000 description 1
- DCKVNWZUADLDEH-UHFFFAOYSA-N sec-butyl acetate Chemical compound CCC(C)OC(C)=O DCKVNWZUADLDEH-UHFFFAOYSA-N 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 235000019795 sodium metasilicate Nutrition 0.000 description 1
- 238000007711 solidification Methods 0.000 description 1
- 230000008023 solidification Effects 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- IAHFWCOBPZCAEA-UHFFFAOYSA-N succinonitrile Chemical compound N#CCCC#N IAHFWCOBPZCAEA-UHFFFAOYSA-N 0.000 description 1
- 230000001629 suppression Effects 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- NZNVBGIQMWGYRR-UHFFFAOYSA-N tert-butyl 2-phenylbenzimidazole-1-carboxylate Chemical compound N=1C2=CC=CC=C2N(C(=O)OC(C)(C)C)C=1C1=CC=CC=C1 NZNVBGIQMWGYRR-UHFFFAOYSA-N 0.000 description 1
- PWQLFIKTGRINFF-UHFFFAOYSA-N tert-butyl 4-hydroxypiperidine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCC(O)CC1 PWQLFIKTGRINFF-UHFFFAOYSA-N 0.000 description 1
- QBOVXIMGMVOPQK-UHFFFAOYSA-N tert-butyl adamantane-1-carboxylate Chemical compound C1C(C2)CC3CC2CC1(C(=O)OC(C)(C)C)C3 QBOVXIMGMVOPQK-UHFFFAOYSA-N 0.000 description 1
- CROWJIMGVQLMPG-UHFFFAOYSA-N tert-butyl benzimidazole-1-carboxylate Chemical compound C1=CC=C2N(C(=O)OC(C)(C)C)C=NC2=C1 CROWJIMGVQLMPG-UHFFFAOYSA-N 0.000 description 1
- MTBKGWHHOBJMHJ-UHFFFAOYSA-N tert-butyl imidazole-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1C=CN=C1 MTBKGWHHOBJMHJ-UHFFFAOYSA-N 0.000 description 1
- KMUNFRBJXIEULW-UHFFFAOYSA-N tert-butyl n,n-bis(2-hydroxyethyl)carbamate Chemical compound CC(C)(C)OC(=O)N(CCO)CCO KMUNFRBJXIEULW-UHFFFAOYSA-N 0.000 description 1
- WIURVMHVEPTKHB-UHFFFAOYSA-N tert-butyl n,n-dicyclohexylcarbamate Chemical compound C1CCCCC1N(C(=O)OC(C)(C)C)C1CCCCC1 WIURVMHVEPTKHB-UHFFFAOYSA-N 0.000 description 1
- UQEXYHWLLMPVRB-UHFFFAOYSA-N tert-butyl n,n-dioctylcarbamate Chemical compound CCCCCCCCN(C(=O)OC(C)(C)C)CCCCCCCC UQEXYHWLLMPVRB-UHFFFAOYSA-N 0.000 description 1
- QJONCGVUGJUWJQ-UHFFFAOYSA-N tert-butyl n,n-diphenylcarbamate Chemical compound C=1C=CC=CC=1N(C(=O)OC(C)(C)C)C1=CC=CC=C1 QJONCGVUGJUWJQ-UHFFFAOYSA-N 0.000 description 1
- RQCNHUCCQJMSRG-UHFFFAOYSA-N tert-butyl piperidine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCCCC1 RQCNHUCCQJMSRG-UHFFFAOYSA-N 0.000 description 1
- CIHOLLKRGTVIJN-UHFFFAOYSA-N tert‐butyl hydroperoxide Chemical compound CC(C)(C)OO CIHOLLKRGTVIJN-UHFFFAOYSA-N 0.000 description 1
- BRGJIIMZXMWMCC-UHFFFAOYSA-N tetradecan-2-ol Chemical compound CCCCCCCCCCCCC(C)O BRGJIIMZXMWMCC-UHFFFAOYSA-N 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- 125000005270 trialkylamine group Chemical group 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- 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 1
- 239000012953 triphenylsulfonium Substances 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
- XMUJIPOFTAHSOK-UHFFFAOYSA-N undecan-2-ol Chemical compound CCCCCCCCCC(C)O XMUJIPOFTAHSOK-UHFFFAOYSA-N 0.000 description 1
- 229930195735 unsaturated hydrocarbon Natural products 0.000 description 1
- PXXNTAGJWPJAGM-UHFFFAOYSA-N vertaline Natural products C1C2C=3C=C(OC)C(OC)=CC=3OC(C=C3)=CC=C3CCC(=O)OC1CC1N2CCCC1 PXXNTAGJWPJAGM-UHFFFAOYSA-N 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 125000005023 xylyl group Chemical group 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
- G03F7/038—Macromolecular compounds which are rendered insoluble or differentially wettable
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/36—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D211/40—Oxygen atoms
- C07D211/44—Oxygen atoms attached in position 4
- C07D211/46—Oxygen atoms attached in position 4 having a hydrogen atom as the second substituent in position 4
-
- 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
- G03F7/038—Macromolecular compounds which are rendered insoluble or differentially wettable
- G03F7/0388—Macromolecular compounds which are rendered insoluble or differentially wettable with ethylenic or acetylenic bands in the side chains of the photopolymer
-
- 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
- G03F7/004—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
-
- 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
- G03F7/20—Exposure; Apparatus therefor
- G03F7/2041—Exposure; Apparatus therefor in the presence of a fluid, e.g. immersion; using fluid cooling means
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/26—Processing photosensitive materials; Apparatus therefor
- G03F7/30—Imagewise removal using liquid means
Definitions
- the present invention relates to a photoresist composition, a resist pattern-forming method, an acid diffusion control agent, and a compound.
- an acid is generated from an acid generating agent upon irradiation with an exposure light such as an ArF excimer laser beam and a KrF excimer laser beam at a light-exposed site, and a reaction catalyzed by the acid allows the difference in dissolution rates in a developer solution to be produced between the light-exposed site and a light-unexposed site, thereby enabling a resist pattern to be formed on a substrate.
- an exposure light such as an ArF excimer laser beam and a KrF excimer laser beam
- the present invention was made in view of the foregoing circumstances, and it is an object of the present invention to provide a photoresist composition that leads to a superior rectangularity of a cross-sectional shape, a superior LWR performance, a superior resolving ability and a favorable depth of focus.
- a photoresist composition containing:
- polymer including an acid-labile group hereinafter, may be also referred to as “(A) polymer” or “polymer (A)”),
- a radiation-sensitive acid generator (hereinafter, may be also referred to as “(B) acid generator” or “acid generator (B)”), and
- an acid diffusion control agent (hereinafter, may be also referred to as “(C) acid diffusion control agent” or “acid diffusion control agent (C)”),
- R 1 , R 2 and R 3 each independently represent a hydrogen atom or a monovalent hydrocarbon group having 1 to 10 carbon atoms, wherein in a case where the monovalent hydrocarbon group is present in a plurality of number, at least two of these hydrocarbon groups optionally taken together represent a ring structure by binding with each other, together with the carbon atom to which the at least two of these hydrocarbon groups bond;
- A represents a group having a valency of n that is obtained by combining: at least one group selected from the group consisting of a hydrogen atom, a linear hydrocarbon group having 1 to 30 carbon atoms and an alicyclic hydrocarbon group having 3 to 30 carbon atoms; at least one group selected from the group consisting of —O—, —CO—, —COO—, —SO 2 O—, —NR—, —NRSO 2 —, —NRSO 2 O— and —NRCO—; and n nitrogen atoms as a binding site to the carbonyl
- the photoresist composition according to the aspect of the present invention contains the acid diffusion control agent (C) and the acid diffusion control agent (C) contains the compound (1) that has the specific structure, the photoresist composition is superior in rectangularity of a cross-sectional shape, an LWR performance, a resolving ability and a depth of focus.
- the compound (1) includes a carbamate group.
- the carbamate group is degraded by an action of an acid generated from the acid generator and the like upon an exposure, and generates a nitrogen atom-containing group. Therefore, the acid diffusion control agent (C) exhibits an excellent acid diffusion controlling function at a light-exposed site, and consequently exhibits superior storage stability.
- the compound (1) After the degradation of the carbamate group, the compound (1) has been converted to a compound that includes the specific polar group and a nitrogen atom-containing group having a molecular weight falling within a specific range (i.e., a sum of the total atomic mass of the group A and n). Therefore, the compound derived from the compound (1) after the degradation has low volatility and a high affinity to a component, e.g., the polymer, in the photoresist composition.
- a component e.g., the polymer
- the compound derived from the compound (1) after the degradation is uniformly distributed in an altitude direction of a resist film formed from the photoresist composition, leading to the suppression of the top loss phenomenon and the like, thereby enabling the formation of a resist pattern exhibiting superior rectangularity of a cross-sectional shape.
- the diffusion of the acid diffusion control agent (C) itself can be inhibited; as a result, the photoresist composition can exhibit a superior LWR performance, a superior resolving ability and a favorable depth of focus.
- R 1 , R 2 , R 3 and n are as defined in the above formula (1);
- R 4 represents a hydrogen atom or a monovalent hydrocarbon group having 1 to 10 carbon atoms;
- R 5 represents a divalent hydrocarbon group having 1 to 10 carbon atoms, wherein R 4 and R 5 optionally taken together represent an alicyclic structure by binding with each other, together with the nitrogen atom to which R 4 and R 5 bond;
- R 6 represents a group having a valency of n that is obtained by combining: at least one group selected from the group consisting of a hydrogen atom, a linear hydrocarbon group having 1 to 30 carbon atoms and an alicyclic hydrocarbon group having 3 to 30 carbon atoms; and at least one group selected from the group consisting of —O—, —CO—, —COO—, —SO 2 O—, —NR—, —NRSO 2 —, —NRSO 2 O— and —NRCO—, wherein a part or all of hydrogen
- the acid diffusion control agent (C) has the specific structure, the basicity of the nitrogen atom-containing group generated from the compound (1) can be increased, and the photoresist composition may lead to an improvement of the rectangularity of a cross-sectional shape, the LWR performance, the resolving ability and the depth of focus.
- R 1 to R 5 are as defined in the above formula (2);
- R 7 , R 8 and R 9 each independently represent at least one group selected from the group consisting of a hydrogen atom, a linear hydrocarbon group having 1 to 30 carbon atoms and an alicyclic hydrocarbon group having 3 to 30 carbon atoms, or a group that is obtained by combining: the at least one group selected from the group consisting of a hydrogen atom, a linear hydrocarbon group having 1 to 30 carbon atoms and an alicyclic hydrocarbon group having 3 to 30 carbon atoms; and at least one group selected from the group consisting of —O—, —CO—, —COO—, —SO 2 O—, —NR—, —NRSO 2 —, —NRSO 2 O— and —NRCO—, wherein at least two of R 7 , R 8 and R 9 optionally taken together represent a ring structure by binding with each other, together with the carbon atom to which the at least two of R 7 , R 8
- the photoresist composition when the acid diffusion control agent (C) has the specific structure, the rectangularity of a cross-sectional shape, the LWR performance, the resolving ability and the depth of focus may be further improved.
- the compound having the specific structure can be easily synthesized from a well-known compound that functions as an acid diffusion control agent through a reaction for forming the functional group X.
- the photoresist composition further contains (D) an acid diffusion controller other than the acid diffusion control agent (C).
- the photoresist composition when the acid diffusion control agent (C) and the acid diffusion control agent other than the acid diffusion control agent (C) are used in combination, the rectangularity of a cross-sectional shape, the LWR performance, the resolving ability and the depth of focus may be improved.
- a resist pattern-forming method including:
- a resist pattern can be formed that exhibits superior rectangularity of a cross-sectional shape, decreased LWR and a superior resolving ability, while attaining a greater depth of focus.
- an acid diffusion control agent contains the compound (1).
- the compound represented by the above formula (1) is represented by the above formula (2), and it is more preferred that the compound represented by the above formula (2) is represented by the above formula (3).
- the acid diffusion control agent contains the compound having the specific structure
- the acid diffusion control agent may be suitably used as an acid diffusion control agent component of the photoresist composition, and enables the photoresist composition to lead to an improvement of the rectangularity of a cross-sectional shape, the LWR performance, the resolving ability and the depth of focus.
- a compound (hereinafter, may be also referred to as “compound (i)”) is represented by the following formula (3):
- R 1 , R 2 and R 3 each independently represent a hydrogen atom or a monovalent hydrocarbon group having 1 to 10 carbon atoms, wherein in a case where the monovalent hydrocarbon group is present in a plurality of number, at least two of these hydrocarbon groups optionally taken together represent a ring structure by binding with each other, together with the carbon atom to which the at least two of these hydrocarbon groups bond;
- R 4 represents a hydrogen atom or a monovalent hydrocarbon group having 1 to 10 carbon atoms;
- R 5 represents a divalent hydrocarbon group having 1 to 10 carbon atoms, wherein R 4 and R 5 optionally taken together represent an alicyclic structure by binding with each other, together with the nitrogen atom to which R 4 and R 5 bond;
- R 7 , R 8 and R 9 each independently represent at least one group selected from the group consisting of a hydrogen atom, a linear hydrocarbon group having 1 to 30 carbon atoms and an alicyclic hydrocarbon group having 3 to 30 carbon atoms, or a group
- the compound (i) since the compound (i) has the specific structure, it may be suitably used as, e.g., an acid diffusion control agent component of a photoresist composition, and enables the rectangularity of a cross-sectional shape, the LWR performance, the resolving ability and the depth of focus to be improved. Moreover, the compound (i) can be easily synthesized from a well-known acid diffusion control agent.
- Organic group as referred to herein means a group having at least one carbon atom.
- the photoresist composition and the resist pattern-forming method using the photoresist composition according to the aspects of the present invention enable a resist pattern to be formed that exhibits superior rectangularity of a cross-sectional shape, decreased LWR and a superior resolving ability, while attaining a greater depth of focus.
- the acid diffusion control agent according to the still another aspect of the present invention can be suitably used as an acid diffusion control agent component of the photoresist composition.
- the compound according to the aspect of the yet still another present invention can be suitably used as the acid diffusion control agent. Therefore, there can be suitably used in pattern formation involved in the production of semiconductor devices, in which further progress of miniaturization is expected in the future.
- a photoresist composition according to an embodiment of the present invention contains (A) a polymer, (B) an acid generator and (C) an acid diffusion control agent.
- the photoresist composition may further contain, in addition to these components, (D) an acid diffusion control agent other than the acid diffusion control agent (C) (hereinafter, may be also referred to as “(D) other acid diffusion controller” or “other acid diffusion controller (D)”), (E) a fluorine atom-containing polymer and (F) a solvent, each as a favorable component, and may contain other optional component(s) within a range not leading to impairment of the effects of the present invention.
- each component will be explained.
- the polymer (A) includes an acid-labile group.
- the polymer (A) preferably further includes, in addition to a structural unit that includes an acid-labile group (hereinafter, may be also referred to as “structural unit (I)”), a structural unit (II) that includes at least one structure selected from the group consisting of a lactone structure, a cyclic carbonate structure and a sultone structure, and the polymer (A) may further include other structural unit such as a structural unit that includes a polar group.
- the polymer (A) may include one, or two or more types of each structural unit. Hereinafter, each structural unit will be explained.
- the structural unit (I) includes an acid-labile group.
- the structural unit (I) is exemplified by a structural unit (I-1) represented by the following formula (4), and the like.
- R A represents a hydrogen atom, a fluorine atom, a methyl group or a trifluoromethyl group
- RP represents a monovalent acid-labile group represented by the above formula (p).
- R p1 , R p2 and R p3 each independently represent an alkyl group having 1 to 4 carbon atoms or a cycloalkyl group having 4 to 20 carbon atoms, wherein R p2 and R p3 optionally taken together represent a cycloalkanediyl group having 4 to 20 carbon atoms by binding with each other, together with the carbon atom to which R p2 and R p3 bond.
- Structural units represented by the following formulae (4-1) to (4-4) are preferred as the structural unit (I-1).
- R A is as defined in the above formula (4);
- R p1 , R p2 and R p3 are as defined in the above formula (p); and i and j are each independently an integer of 1 to 4.
- R A is as defined in the above formula (4).
- the structural unit (I) is preferably the structural unit represented by the above formula (4-1) or the structural unit represented by the formula (4-2), more preferably a structural unit derived from 1-alkyl-1-cyclopentyl (meth)acrylate or a structural unit derived from 2-alkyl-2-adamantyl (meth)acrylate, and still more preferably a structural unit derived from 1-ethyl-1-cyclopentyl (meth)acrylate or a structural unit derived from 2-ethyl-2-adamantyl (meth)acrylate.
- the proportion of the structural unit (I) with respect to the total structural units constituting the polymer (A) is preferably 10 mol % to 100 mol %, more preferably 20 mol % to 80 mol %, and still more preferably 30 mol % to 70 mol %.
- the proportion of the structural unit (I) is less than the lower limit, the pattern formability of the photoresist composition may be deteriorated.
- the structural unit (II) includes at least one structure selected from the group consisting of a lactone structure, a cyclic carbonate structure and a sultone structure.
- the solubility thereof in a developer solution may be adjusted.
- the adhesiveness of a resist pattern formed from the photoresist composition to a substrate may be improved.
- the structural unit (II) is exemplified by structural units represented by the following formulae, and the like.
- R L1 represents a hydrogen atom, a fluorine atom, a methyl group or a trifluoromethyl group.
- a structural unit that includes a lactone structure and a structural unit that includes a sultone structure are preferred, and a structural unit that includes a norbornanelactone structure and a structural unit that includes a norbornanesultone structure are more preferred.
- the proportion of the structural unit (II) with respect to the total structural units constituting the polymer (A) is preferably 30 mol % to 80 mol %, more preferably 35 mol % to 70 mol %, and still more preferably 40 mol % to 60 mol %.
- the proportion of the structural unit (II) is less than the lower limit, the adhesiveness of a resist pattern formed from the photoresist composition to a substrate may be deteriorated.
- the proportion of the structural unit (II) is greater than the upper limit, the pattern formability of the photoresist composition may be deteriorated.
- the polymer (A) may include other structural unit that is different from the structural units (I) and (II).
- the other structural unit is exemplified by a first other structural unit that includes a polar group, and the like (except for those corresponding to the structural unit (I) and the structural unit (II)).
- the polar group include a hydroxy group, a carboxy group, a cyano group, a nitro group, a sulfonamide group, and the like. Among these, a hydroxy group and a carboxy group are preferred, and a hydroxy group is more preferred.
- Examples of the structural unit that includes a polar group include structural units represented by the following formulae, and the like.
- R B represents a hydrogen atom, a fluorine atom, a methyl group or a trifluoromethyl group.
- the proportion of the structural unit that includes a polar group with respect to the total structural units constituting the polymer (A) is preferably 0 mol % to 80 mol %, more preferably 0 mol % to 75 mol %, and still more preferably 30 mol % to 70 mol %.
- the proportion of the structural unit that includes a polar group is greater than the upper limit, the pattern formability of the photoresist composition may be deteriorated.
- the polymer (A) may include a second other structural unit as well as the first structural unit that includes a polar group.
- the proportion of the second other structural unit with respect to the total structural units constituting the polymer (A) is typically no greater than 30 mol %, and preferably no greater than 20 mol %. When the proportion of the second other structural unit is greater than the upper limit, the pattern formability of the photoresist composition may be deteriorated.
- the content of the polymer (A) with respect to the total solid content of the photoresist composition is typically no less than 70% by mass, preferably no less than 80% by mass, and more preferably no less than 85% by mass.
- the polymer (A) can be synthesized, for example, by polymerizing monomer(s) that give(s) each structural unit in an appropriate solvent using a radical polymerization initiator.
- radical polymerization initiator examples include azo radical initiators such as azobisisobutyronitrile (AIBN), 2,2′-azobis(4-methoxy-2,4-dimethylvaleronitrile), 2,2′-azobis(2-cyclopropylpropionitrile), 2,2′-azobis(2,4-dimethylvaleronitrile) and dimethyl 2,2′-azobisisobutyrate; peroxide radical initiators such as benzoyl peroxide, t-butyl hydroperoxide and cumene hydroperoxide; and the like.
- AIBN azobisisobutyronitrile
- dimethyl 2,2′-azobisisobutyrate are preferred, and AIBN are more preferred.
- These radical initiators may be used either alone, or as a mixture of two or more types thereof.
- Examples of the solvent used in the polymerization include:
- alkanes such as n-pentane, n-hexane, n-heptane, n-octane, n-nonane and n-decane;
- cycloalkanes such as cyclohexane, cycloheptane, cyclooctane, decalin and norbornane;
- aromatic hydrocarbons such as benzene, toluene, xylene, ethylbenzene and cumene;
- halogenated hydrocarbons such as chlorobutanes, bromohexanes, dichloroethanes, hexamethylene dibromide and chlorobenzene;
- saturated carboxylic acid esters such as ethyl acetate, n-butyl acetate, i-butyl acetate and methyl propionate;
- ketones such as acetone, methyl ethyl ketone, 4-methyl-2-pentanone and 2-heptanone;
- ethers such as tetrahydrofuran, diethoxyethanes and diethoxyethanes
- alcohols such as methanol, ethanol, 1-propanol, 2-propanol and 4-methyl-2-pentanol; and the like. These solvents used in the polymerization may be used either alone, or in combination of two or more types thereof.
- the reaction temperature in the polymerization is typically 40° C. to 150° C., and preferably 50° C. to 120° C.
- the reaction time period is typically 1 hour to 48 hrs, and preferably 1 hour to 24 hrs.
- the polystyrene equivalent weight average molecular weight (Mw) of the polymer (A) as determined by gel permeation chromatography (GPC) is not particularly limited, the Mw is preferably no less than 1,000 and no greater than 50,000, more preferably no less than 2,000 and no greater than 30,000, still more preferably no less than 3,000 and no greater than 20,000, and particularly preferably no less than 5,000 and no greater than 15,000.
- Mw polystyrene equivalent weight average molecular weight of the polymer (A) as determined by gel permeation chromatography
- the ratio (Mw/Mn) of the Mw to the polystyrene equivalent number average molecular weight (Mn) as determined by GPC of the polymer (A) is typically no less than 1 and no greater than 5, preferably no less than 1 and no greater than 3, and still more preferably no less than 1 and no greater than 2.
- the Mw and Mn of the polymer as used herein are determined using gel permeation chromatography (GPC) under the following conditions:
- GPC columns G2000HXL ⁇ 2, G3000HXL ⁇ 1, and G4000HXL ⁇ 1 (each manufactured by Tosoh Corporation)
- elution solvent tetrahydrofuran (manufactured by Wako Pure Chemical Industries, Ltd.)
- the content of low molecular weight components (the low molecular weight components mean components having a molecular weight of less than 1,000) in the polymer (A) is preferably no greater than 0.5% by mass, more preferably no greater than 0.2% by mass, and still more preferably no greater than 0.1% by mass.
- the photoresist composition may lead to a further improvement of the rectangularity of a cross-sectional shape, the LWR performance, the resolving ability and the depth of focus.
- the content of the low molecular weight components of the polymer as used herein is determined by high performance liquid chromatography (HPLC) using an Intersil ODS-25 ⁇ m column (4.6 mm ⁇ 250 mm; manufactured by GL Sciences, Inc.) under the following conditions:
- elution solvent acrylonitrile/0.1% by mass aqueous phosphoric acid solution
- the acid generator (B) generates an acid upon an exposure.
- the acid-labile group included in the polymer (A) is dissociated by the acid to generate a polar group such as a carboxy group, whereby the solubility of the polymer (A) in a developer solution is altered.
- the mode of incorporation of the acid generator (B) in the photoresist composition may be in a low molecular weight compound form (hereinafter, may be also referred to as “(B) acid generating agent” or “acid generating agent (B)”, as appropriate), as described later, or in a form of an acid generating group incorporated into the polymer as a part thereof, or in both of these forms.
- the acid generating agent (B) is exemplified by an onium salt compound, an N-sulfonyloxyimide compound, a halogen-containing compound, a diazoketone compound, and the like.
- the onium salt compound is exemplified by a sulfonium salt, a tetrahydrothiophenium salt, an iodonium salt, a phosphonium salt, a diazonium salt, a pyridinium salt, and the like.
- sulfonium salt examples include triphenylsulfonium trifluoromethanesulfonate, triphenylsulfonium nonafluoro-n-butanesulfonate, triphenylsulfonium perfluoro-n-octanesulfonate, triphenylsulfonium 2-bicyclo[2.2.1]hept-2-yl-1,1,2,2-tetrafluoroethanesulfonate, triphenylsulfonium 2-bicyclo[2.2.1]hept-2-yl-1,1-difluoroethanesulfonate, triphenylsulfonium camphorsulfonate, 4-cyclohexylphenyldiphenylsulfonium trifluoromethanesulfonate, 4-cyclohexylphenyldiphenylsulfonium nonafluoro-n-butanesulfonate, 4-cyclohex
- tetrahydrothiophenium salt examples include 1-(4-n-butoxynaphthalen-1-yl)tetrahydrothiophenium trifluoromethanesulfonate, 1-(4-n-butoxynaphthalen-1-yl)tetrahydrothiophenium nonafluoro-n-butanesulfonate, 1-(4-n-butoxynaphthalen-1-yl)tetrahydrothiophenium perfluoro-n-octanesulfonate, 1-(4-n-butoxynaphthalen-1-yl)tetrahydrothiophenium 2-bicyclo[2.2.1]hept-2-yl-1,1,2,2-tetrafluoroethanesulfonate, 1-(4-n-butoxynaphthalen-1-yl)tetrahydrothiophenium camphorsulfonate, 1-(6-n-butoxynaphthalen-2-yl)tetrahydrothioph
- iodonium salt examples include diphenyliodonium trifluoromethanesulfonate, diphenyliodonium nonafluoro-n-butanesulfonate, diphenyliodonium perfluoro-n-octanesulfonate, diphenyliodonium 2-bicyclo[2.2.1]hept-2-yl-1,1,2,2-tetrafluoroethanesulfonate, diphenyliodonium camphorsulfonate, bis(4-t-butylphenyl)iodonium trifluoromethanesulfonate, bis(4-t-butylphenyl)iodonium nonafluoro-n-butanesulfonate, bis(4-t-butylphenyl)iodonium perfluoro-n-octanesulfonate, bis(4-t-butylphenyl)iodonium 2-bicyclo[
- N-sulfonyloxyimide compound examples include N-(trifluoromethanesulfonyloxy)bicyclo[2.2.1]hept-5-ene-2,3-dicarboxyimide, N-(nonafluoro-n-butanesulfonyloxy)bicyclo[2.2.1]hept-5-ene-2,3-dicarboxyimide, N-(perfluoro-n-octanesulfonyloxy)bicyclo[2.2.1]hept-5-ene-2,3-dicarboxyimide, N-(2-bicyclo[2.2.1]hept-2-yl-1,1,2,2-tetrafluoroethanesulfonyloxy)bicyclo[2.2.1]hept-5-ene-2,3-dicarboxyimide, N-(2-(3-tetracyclo[4.4.0.1 2,5 .1 7,10 ]dodecanyl)-1,1-difluoroethane
- an onium salt compound is preferred, a sulfonium salt is more preferred, and triphenylsulfonium 2-bicyclo[2.2.1]hept-2-yl-1,1-difluoroethanesulfonate is still more preferred.
- the amount of the acid generator (B) with respect to 100 parts by mass of the polymer (A) is preferably no less than 0.1 parts by mass and no greater than 30 parts by mass, more preferably no less than 0.5 parts by mass and no greater than 20 parts by mass, and still more preferably no less than 1 part by mass and no greater than 15 parts by mass in light of attaining the sensitivity and developability of the photoresist composition.
- the amount of the acid generating agent (B) falls within the above range, the sensitivity and developability of the photoresist composition may be improved.
- One, or two or more types of the acid generator (B) may be used.
- the acid diffusion control agent (C) contains the compound (1).
- the photoresist composition contains the acid diffusion control agent (C) in addition to the polymer (A) and the acid generator (B)
- the photoresist composition leads to a superior rectangularity of a cross-sectional shape, a superior LWR performance, a superior resolving ability and a favorable depth of focus.
- One, or two or more types of the acid diffusion control agent (C) may be used.
- the compound (1) is represented by the above formula (1).
- R 1 , R 2 and R 3 each independently represent a hydrogen atom or a monovalent hydrocarbon group having 1 to 10 carbon atoms, wherein in a case where the monovalent hydrocarbon group is present in a plurality of number, at least two of these hydrocarbon groups optionally taken together represent a ring structure by binding with each other, together with the carbon atom to which the at least two of these hydrocarbon groups bond;
- A represents a group having a valency of n that is obtained by combining: at least one group selected from the group consisting of a hydrogen atom, a linear hydrocarbon group having 1 to 30 carbon atoms and an alicyclic hydrocarbon group having 3 to 30 carbon atoms; at least one group selected from the group consisting of —O—, —CO—, —COO—, —SO 2 O—, —NR—, —NRSO 2 —, —NRSO 2 O— and —NRCO—; and n nitrogen atoms as a binding site to the carbonyl group
- the monovalent hydrocarbon group having 1 to 10 carbon atoms which may be represented by R 1 , R 2 or R 3 is exemplified by a monovalent linear hydrocarbon group having 1 to 10 carbon atoms, a monovalent alicyclic hydrocarbon group having 3 to 10 carbon atoms, a monovalent aromatic hydrocarbon group having 6 to 10 carbon atoms, and the like.
- Examples of the monovalent linear hydrocarbon group having 1 to 10 carbon atoms include:
- alkyl groups such as a methyl group, an ethyl group, a n-propyl group, an i-propyl group, a n-butyl group, an i-butyl group, a sec-butyl group and a t-butyl group;
- alkenyl groups such as an ethenyl group, a propenyl group and a butenyl group
- alkynyl groups such as an ethynyl group, a propynyl group and a butynyl group; and the like.
- Examples of the monovalent alicyclic hydrocarbon group having 3 to 10 carbon atoms include:
- monocyclic cycloalkyl groups such as a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group and a cyclodecyl group;
- polycyclic cycloalkyl groups such as a norbornyl group, an adamantyl group and a tricyclodecyl group;
- monocyclic cycloalkenyl groups such as a cyclopentenyl group and a cyclohexenyl group
- polycyclic cycloalkenyl groups such as a norbornenyl group and a tricyclodecenyl group; and the like.
- Examples of the monovalent aromatic hydrocarbon group having 6 to 10 carbon atoms include:
- aryl groups such as a phenyl group, a tolyl group, a xylyl group, a mesityl group and a naphthyl group;
- aralkyl groups such as a benzyl group, a phenethyl group and a phenylpropyl group; and the like.
- Examples of the ring structure which may be taken together represented by at least two of the hydrocarbon groups by binding with each other include:
- monocyclic cycloalkane structures such as a cyclobutane structure, a cyclopentane structure, a cyclohexane structure, a cyclooctane structure and a cyclodecane structure and;
- polycyclic cycloalkane structures such as a bicyclo[2.2.1]heptane structure, a bicyclo[2.2.2]octane structure, an adamantane structure and a tricyclodecane structure; and the like.
- R 1 , R 2 and R 3 represent preferably a hydrogen atom or a linear hydrocarbon group, more preferably a hydrogen atom or an alkyl group, still more preferably an alkyl group, and particularly preferably a methyl group or an ethyl group.
- the group constituted with R 1 , R 2 , R 3 and the carbon atom to which R 1 , R 2 and R 3 bond is preferably a t-butyl group or a t-amyl group.
- Examples of the linear hydrocarbon group having 1 to 30 carbon atoms that constitutes A include groups obtained by eliminating at least one hydrogen atom from a linear hydrocarbon such as:
- alkane such as methane, ethane, propane, butane, isobutane, n-pentane, isopentane, n-hexane and isohexane;
- alkene such as ethene, propene, n-butene, isobutene, n-pentene and isopentene;
- alkyne such as ethyne, propyne, butyne and pentyne; and the like.
- Examples of the alicyclic hydrocarbon group having 3 to 30 carbon atoms that constitutes A include groups obtained by eliminating at least one hydrogen atom from an alicyclic hydrocarbon such as:
- a monocyclic cycloalkane such as cyclopropane, cyclobutane, cyclopentane, cyclohexane, cyclooctane and cyclodecane;
- a polycyclic cycloalkane such as norbornane, adamantane and tricyclodecane
- a monocyclic cycloalkene such as cyclopropene, cyclobutene, cyclopentene, cyclohexene, cyclooctene and cyclodecene;
- a polycyclic cycloalkene such as norbornene and tricyclodecene; and the like.
- fluorine atom-free substituent which may be included in the linear hydrocarbon group and the alicyclic hydrocarbon group include a cyano group, a nitro group, and the like.
- Examples of the group that is obtained by combining: at least one group selected from the group consisting of a hydrogen atom, the linear hydrocarbon group and the alicyclic hydrocarbon group; and at least one group selected from the group consisting of —O—, —CO—, —COO—, —SO 2 O—, —NR—, —NRSO 2 —, —NRSO 2 O— and —NRCO—, which constitute A, include cyclic ether groups, cyclic ketone groups, lactone groups, sultone groups, cyclic amino groups, cyclic sulfonamide groups, cyclic oxysulfonamide groups, lactam groups, alkoxy groups, acyl groups, acyloxy groups, alkylsulfonyloxy groups, alkoxysulfonyl groups, alkylamino groups, dialkylamino groups, alkoxyalkyl groups, acylalkyl groups, acyloxyalkyl groups, alkoxyalkyl groups
- Examples of the monovalent hydrocarbon group having 1 to 10 carbon atoms which may be represented by R include groups similar to those exemplified as the monovalent hydrocarbon group having 1 to 10 carbon atoms in connection with R 1 , R 2 and R 3 , as described above, and the like.
- n is an integer of 1 to 3, more preferably 1 or 2, and still more preferably 1 in light of the ease in synthesis of the compound (1).
- the lower limit of the sum of the atomic masses of the atoms constituting A is 120, preferably 150, more preferably 200, still more preferably 250, and particularly preferably 290.
- the sum of the atomic masses of the atoms constituting A is less than the lower limit, the volatility of the compound generated from the compound (1) after the exposure tends to be elevated, and as a result, the photoresist composition may lead to deterioration of the rectangularity of a cross-sectional shape.
- the upper limit of the sum of the atomic masses of the atoms constituting A is preferably 1,000, more preferably 800, still more preferably 600, and particularly preferably 500.
- the dispersibility of the compound (1) in the resist film may be reduced, resulting in the tendency that the rectangularity of a cross-sectional shape, the LWR performance, the resolving ability and the depth of focus of the photoresist composition are deteriorated.
- the compound (1) is exemplified by compounds represented by the following formulae (i1) to (i21) (hereinafter, may be also referred to as “compounds (i1) to (i-21)”), and the like.
- the compound (1) is preferably the compound represented by the above formula (2) (hereinafter, may be also referred to as “compound (2)”).
- R 1 , R 2 , R 3 and n are as defined in the above formula (1);
- R 4 represents a hydrogen atom or a monovalent hydrocarbon group having 1 to 10 carbon atoms;
- R 5 represents a divalent hydrocarbon group having 1 to 10 carbon atoms, wherein R 4 and R 5 optionally taken together represent an alicyclic structure by binding with each other, together with the nitrogen atom to which R 4 and R 5 bond;
- R 6 represents a group having a valency of n that is obtained by combining: at least one group selected from the group consisting of a hydrogen atom, a linear hydrocarbon group having 1 to 30 carbon atoms and an alicyclic hydrocarbon group having 3 to 30 carbon atoms; and at least one group selected from the group consisting of —O—, —CO—, —COO—, —SO 2 O—, —NR—, —NRSO 2 —, —NRSO 2 O— and —NRCO—, wherein a part or all of hydrogen
- Examples of the monovalent hydrocarbon group having 1 to 10 carbon atoms which may be represented by R 4 include groups similar to those exemplified as the monovalent hydrocarbon group in connection with R 1 , R 2 and R 3 , as described above.
- Examples of the divalent hydrocarbon group having 1 to 10 carbon atoms represented by R 5 include groups derived by eliminating one hydrogen atom from a group exemplified as the monovalent hydrocarbon group in connection with R 1 , R 2 and R 3 , as described above, and the like.
- Examples of the ring structure which may be represented by R 4 and R 5 by binding with each other, together with the nitrogen atom to which R 4 and R 5 bond include:
- monocyclic azacycloalkane structures such as an azacyclopropane structure, an azacyclobutane structure, an azacyclopentane structure (pyrrolidine structure), an azacyclohexane structure (piperidine structure), an azacycloheptane structure, an azacyclooctane structure and an azacyclodecane structure;
- polycyclic azacycloalkane structures such as an azabicyclo[2.2.1]heptane structure, an azabicyclo[2.2.2]octane structure, an azatricyclo[3.3.1.1 3,7 ]decane structure; and the like.
- monocyclic azacycloalkane structures are preferred, an azacyclopentane structure and an azacyclohexane structure are more preferred, and an azacyclohexane structure is still more preferred.
- Examples of the linear hydrocarbon group having 1 to 30 carbon atoms that constitutes R 6 include groups similar to those exemplified as the linear hydrocarbon group in connection with the groups that constitute A, and the like.
- Examples of the alicyclic hydrocarbon group having 3 to 30 carbon atoms that constitutes R 6 include groups similar to those exemplified as the alicyclic hydrocarbon group in connection with the groups that constitute A, and the like.
- Examples of the fluorine atom-free substituent that may be included in R 6 include a cyano group, a nitro group, and the like.
- the lower limit of the value obtained by the formula of: [(a formula mass of R 4 +a formula mass of R 5 +an atomic mass of nitrogen) ⁇ n+(a formula mass of R 6 )] (hereinafter, may be also referred to as “the total atomic mass (1)”) in the above formula (2) is 120, preferably 150, more preferably 200, still more preferably 250, and particularly preferably 290.
- the volatility of the compound generated from the compound (2) after the exposure may be elevated, resulting in the tendency that the rectangularity of a cross-sectional shape of the photoresist composition is deteriorated.
- the upper limit of the total atomic mass (1) is preferably 1,000, more preferably 800, still more preferably 600, and particularly preferably 500.
- the dispersibility of the compound (2) in the resist film may be reduced, resulting in the tendency that the photoresist composition leads to deterioration of the rectangularity of a cross-sectional shape, the LWR performance, the resolving ability and the depth of focus.
- the formula mass of the group as referred to means a sum of atomic masses of the atoms constituting the group.
- the compound (2) is exemplified by the compounds (i1) to (i15), (i19), and (i20), and the like.
- the compound (2) is preferably the compound (i).
- the compound (i) is represented by the above formula (3).
- R 1 to R 5 are as defined in the above formula (2);
- R 7 , R 8 and R 9 each independently represent at least one group selected from the group consisting of a hydrogen atom, a linear hydrocarbon group having 1 to 30 carbon atoms and an alicyclic hydrocarbon group having 3 to 30 carbon atoms, or a group that is obtained by combining: the at least one group selected from the group consisting of a hydrogen atom, a linear hydrocarbon group having 1 to 30 carbon atoms and an alicyclic hydrocarbon group having 3 to 30 carbon atoms; and the at least one group selected from the group consisting of —O—, —CO—, —COO—, —SO 2 O—, —NR—, —NRSO 2 —, —NRSO 2 O— and —NRCO—, wherein at least two of R 7 , R 8 and R 9 optionally taken together represent a ring structure by binding with each other, together with the carbon atom to which the at least two of R 7 , R 8
- Examples of the linear hydrocarbon group having 1 to 30 carbon atoms and the alicyclic hydrocarbon group having 3 to 30 carbon atoms which may be represented by R 7 , R 8 or R 9 include groups similar to those exemplified as the linear hydrocarbon group and the alicyclic hydrocarbon group in connection with A in the above formula (1), and the like.
- R 7 , R 8 and R 9 represent preferably a hydrogen atom, a linear hydrocarbon group or an alkoxycarbonylalkyl group, more preferably a hydrogen atom, a methyl group or an ethoxycarbonyl group, and still more preferably a hydrogen atom or an ethoxycarbonyl group.
- Examples of the ring structure taken together represented by at least two of R 7 , R 8 and R 9 by binding with each other, together with the carbon atom to which the at least two of R 7 , R 8 and R 9 bond include:
- polycyclic alicyclic structures such as a norbornane structure, an adamantane structure and a camphor structure; and the like.
- polycyclic alicyclic structures are preferred, and an adamantane structure and a camphor structure are more preferred.
- X represents preferably —O—, —COO— or —SO 2 O—, more preferably —COO—, —SO 2 O—, and still more preferably —COO—*, —SO 2 O—* (* denotes a binding site to R 5 in the above formula (3)).
- the lower limit of the sum of the formula masses of R 4 , R 5 , X, R 7 , R 8 and R 9 and the atomic masses of the nitrogen and the carbon in the formula (3) (hereinafter, may be also referred to as “the total atomic mass (2)”) is 120, preferably 150, more preferably 200, still more preferably 250, and particularly preferably 290.
- the volatility of the compound generated from the compound (i) after the exposure may be elevated, resulting in the tendency that the rectangularity of a cross-sectional shape of the photoresist composition is deteriorated.
- the upper limit of the total atomic mass (2) is preferably 1,000, more preferably 800, still more preferably 600, and particularly preferably 500.
- the dispersibility of the compound (i) in the resist film may be reduced, resulting in the tendency that the photoresist composition leads to deterioration of the rectangularity of a cross-sectional shape, the LWR performance, the resolving ability and the depth of focus.
- Examples of the compound (i) include the compounds (i-1) to (i-15), and the like.
- the compound (i) can be synthesized in accordance with the following reaction scheme, for example.
- R 1 , R 2 and R 3 each independently represent a hydrogen atom or a monovalent hydrocarbon group having 1 to 10 carbon atoms, wherein in a case where the monovalent hydrocarbon group is present in a plurality of number, at least two of these hydrocarbon groups optionally taken together represent a ring structure by binding with each other, together with the carbon atom to which the at least two of these hydrocarbon groups bond;
- R 4 represents a hydrogen atom or a monovalent hydrocarbon group having 1 to 10 carbon atoms;
- R 5 represents a divalent hydrocarbon group having 1 to 10 carbon atoms, wherein R 4 and R 5 optionally taken together represent an alicyclic structure by binding with each other, together with the nitrogen atom to which R 4 and R 5 bond;
- R 7 , R 8 and R 9 each independently represent at least one group selected from the group consisting of a hydrogen atom, a linear hydrocarbon group having 1 to 30 carbon atoms and an alicyclic hydrocarbon group having 3 to 30 carbon atoms, or a group
- the compound (i) that includes X can be obtained, for example, by reacting the compound that includes Y with the compound that includes Z, in a solvent such as dichloromethane in the presence of a base such as triethylamine or dimethylaminopyridine (DMAP).
- a solvent such as dichloromethane
- a base such as triethylamine or dimethylaminopyridine (DMAP).
- the content of the acid diffusion control agent (C) with respect of the acid generating agent (B) is preferably 1 mol % to 100 mol %, more preferably 3 mol % to 70 mol %, and still more preferably 5 mol % to 50 mol %, in light of the possibility that the photoresist composition leads to an improvement of the LWR performance, an EL (Exposure Latitude) performance and the rectangularity of a cross-sectional shape.
- the photoresist composition may lead to an improvement of the rectangularity of a cross-sectional shape, the LWR performance, the resolving ability and the sensitivity.
- the amount of the acid diffusion control agent (C) with respect to 100 parts by mass of the polymer (A) is preferably no less than 0.1 parts by mass and no greater than 30 parts by mass, more preferably no less than 0.5 parts by mass and no greater than 20 parts by mass, and still more preferably no less than 1 part by mass and no greater than 15 parts by mass.
- the photoresist composition according to the embodiment of the present invention may contain (D) other acid diffusion controller, as needed.
- the photoresist composition further contains the other acid diffusion controller (D) in addition to the acid diffusion control agent (C)
- the rectangularity of a cross-sectional shape, the LWR performance, the resolving ability and the depth of focus may be further improved.
- the other acid diffusion controller (D) it may be presumed, for example, that a degree of diffusion of the compound as a whole contained in the acid diffusion control agent can be adjusted; and the like.
- the mode of incorporation of the other acid diffusion controller (D) in the photoresist composition may be in an acid diffusion control agent form which is a low molecular weight compound (hereinafter, may be also referred to as “(D) other acid diffusion control agent” or “other acid diffusion control agent (D)”, as appropriate), as described later, or in a form of an acid diffusion control group incorporated into the polymer as a part thereof, or in both of these forms.
- the other acid diffusion control agent (D) is exemplified by a compound represented by the following formula (5) (hereinafter, may be also referred to as “nitrogen-containing compound (I)”), a compound including two nitrogen atoms in a single molecule (hereinafter, may be also referred to as “nitrogen-containing compound (II)”), a compound including three nitrogen atoms (hereinafter, may be also referred to as “nitrogen-containing compound (III)”), an amide group-containing compound, a urea compound, a nitrogen-containing heterocyclic compound, and the like.
- nitrogen-containing compound (I) a compound represented by the following formula (5)
- nitrogen-containing compound (II) a compound including two nitrogen atoms in a single molecule
- nitrogen-containing compound (III) a compound including three nitrogen atoms
- R 10 , R 11 and R 12 each independently represent a hydrogen atom, a linear, branched or cyclic alkyl group, an aryl group or an aralkyl group each unsubstituted or substituted.
- nitrogen-containing compound (I) examples include monoalkylamines such as n-hexylamine; dialkylamines such as di-n-butylamine; trialkylamines such as triethylamine; aromatic amines such as aniline; and the like.
- nitrogen-containing compound (II) examples include ethylenediamine, N,N,N′,N′-tetramethylethylenediamine, and the like.
- nitrogen-containing compound (III) examples include polyamine compounds such as polyethyleneimine and polyallylamine; polymers of dimethylaminoethylacrylamide, etc.; and the like.
- amide group-containing compound examples include formamide, N-methylformamide, N,N-dimethylformamide, acetamide, N-methylacetamide, N,N-dimethylacetamide, propionamide, benzamide, pyrrolidone, N-methylpyrrolidone, and the like.
- urea compound examples include urea, methylurea, 1,1-dimethylurea, 1,3-dimethylurea, 1,1,3,3-tetramethylurea, 1,3-diphenylurea, tributylthiourea, and the like.
- nitrogen-containing heterocyclic compound examples include pyridines such as pyridine and 2-methylpyridine, pyrazine, pyrazole, and the like.
- a compound that includes an acid-labile group may also be used as the nitrogen-containing organic compound.
- nitrogen-containing organic compound that includes an acid-labile group include N-(t-butoxycarbonyl)piperidine, N-(t-butoxycarbonyl)imidazole, N-(t-butoxycarbonyl)benzimidazole, N-(t-butoxycarbonyl)-2-phenylbenzimidazole, N-(t-butoxycarbonyl)di-n-octylamine, N-(t-butoxycarbonyl)-diethanolamine, N-(t-butoxycarbonyl)-dicyclohexylamine, N-(t-butoxycarbonyl)-diphenylamine, N-(t-butoxycarbonyl)-4-hydroxypiperidine, and the like.
- a photodegradable base that is sensitized upon an exposure to generate a weak acid may be used as the other acid diffusion controller (D).
- the photodegradable base include onium salt compounds that are degraded upon an exposure and lose its acid diffusion controlling ability, and the like.
- the onium salt compound include a sulfonium salt compound represented by the following formula (6-1), an iodonium salt compound represented by the following formula (6-2), and the like.
- le to R 17 each independently represent a hydrogen atom, an alkyl group, an alkoxy group, a hydroxy group or a halogen atom;
- E ⁇ and Q ⁇ each independently represent OH ⁇ , R ⁇ COO ⁇ , R ⁇ —SO 3 ⁇ or an anion represented by the following formula (6-3), wherein R ⁇ represents an alkyl group, an aryl group or an aralkyl group.
- R 18 represents a linear or branched alkyl group having 1 to 12 carbon atoms, or a linear or branched alkoxyl group having 1 to 12 carbon atoms, wherein a part or all of hydrogen atoms included in the linear or branched alkyl group and the linear or branched alkoxyl group are unsubstituted or substituted with a fluorine atom; and u is an integer of 0 to 2.
- the content of the other acid diffusion controller (D) with respect of the acid generating agent (B) is preferably 1 mol % to 100 mol %, more preferably 3 mol % to 70 mol %, and still more preferably 5 mol % to 50 mol %.
- the photoresist composition may lead to deterioration of the sensitivity, the rectangularity of a cross-sectional shape, the LWR performance, the resolving ability and the depth of focus.
- the amount of the other acid diffusion control agent (D) with respect to 100 parts by mass of the polymer (A) is preferably 0 to 20 parts by mass, more preferably 0.1 parts by mass to 15 parts by mass, and still more preferably 0.3 parts by mass to 10 parts by mass.
- the photoresist composition according to the embodiment of the present invention may contain (E) a fluorine-containing polymer (except for those corresponding to the polymer (A)).
- E a fluorine-containing polymer
- the fluorine-containing polymer (E) tends to be unevenly distributed in the vicinity of the surface of the resist film due to oil repellent characteristics of the fluorine-containing polymer in the film, and thus elution of the acid generating agent, the acid diffusion control agent and the like into a liquid immersion medium can be inhibited during an exposure through the liquid immersion medium.
- an advancing contact angle of the liquid immersion medium on the resist film can be controlled to fall within a desired range, whereby formation of bubble defects can be inhibited. Furthermore, a larger receding contact angle of the liquid immersion medium on the resist film is attained, thereby enabling an exposure by high-speed scanning without being accompanied by residual water beads.
- the photoresist composition contains the fluorine-containing polymer (E)
- a resist film suitable for a liquid immersion lithography process can be formed.
- the fluorine-containing polymer (E) is not particularly limited as long as the fluorine-containing polymer (E) contains a fluorine atom; however, it is preferred that the fluorine-containing polymer (E) has a higher content (% by mass) of fluorine atoms than that of the polymer (A) in the photoresist composition.
- the fluorine-containing polymer (E) has a higher content (% by mass) of fluorine atoms than that of the polymer (A)
- a higher degree of the aforementioned uneven distribution is attained, leading to an improvement of characteristics such as water repellency and elution inhibitory ability of the resulting resist film.
- the content of fluorine atoms of the fluorine-containing polymer (E) falls within a range of preferably no less than 1% by mass, more preferably 2% by mass to 60% by mass, still more preferably 4% by mass to 40% by mass, and particularly preferably 7% by mass to 30% by mass.
- the content of fluorine atoms of the fluorine-containing polymer (E) is less than the lower limit, the hydrophobicity of the surface of the resist film may be deteriorated.
- the content (% by mass) of fluorine atoms of the polymer can be calculated based on the structure of the polymer as determined by 13 C-NMR spectroscopy.
- the fluorine-containing polymer (E) preferably has at least one selected from the group consisting of the following structural unit (Ea) and the following structural unit (Eb).
- the fluorine-containing polymer (E) may have one, or two or more types of the structural unit (Ea) and/or the structural unit (Eb).
- the structural unit (Ea) is represented by the following formula (7a).
- the fluorine-containing polymer (E) has the structural unit (Ea)
- the content of fluorine atoms thereof can be adjusted.
- R D represents a hydrogen atom, a methyl group or a trifluoromethyl group
- G represents a single bond, an oxygen atom, a sulfur atom, —CO—O—, —SO 2 —O—NH—, —CO—NH— or —O—CO—NH—
- R E represents a monovalent linear hydrocarbon group having 1 to 6 carbon atoms and having at least one fluorine atom, or a monovalent aliphatic cyclic hydrocarbon group having 4 to 20 carbon atoms and having at least one fluorine atom.
- Examples of the linear hydrocarbon group having 1 to 6 carbon atoms and having at least one fluorine atom which may be represented by R E include a trifluoromethyl group, a 2,2,2-trifluoroethyl group, a perfluoroethyl group, a 2,2,3,3,3-pentafluoropropyl group, a 1,1,1,3,3,3-hexafluoropropyl group, a perfluoro-n-propyl group, a perfluoro-i-propyl group, a perfluoro-n-butyl group, a perfluoro-i-butyl group, a perfluoro-t-butyl group, a 2,2,3,3,4,4,5,5-octafluoropentyl group, a perfluorohexyl group, and the like.
- Examples of the aliphatic cyclic hydrocarbon group having 4 to 20 carbon atoms and having at least one fluorine atom which may be represented by R E include a monofluorocyclopentyl group, a difluorocyclopentyl group, a perfluorocyclopentyl group, a monofluorocyclohexyl group, a difluorocyclopentyl group, a perfluorocyclohexylmethyl group, a fluoronorbornyl group, a fluoroadamantyl group, a fluorobornyl group, a fluoroisobornyl group, a fluorotricyclodecyl group, a fluorotetracyclodecyl group, and the like.
- Examples of the monomer that gives the structural unit (Ea) include (meth)acrylic acid trifluoromethyl ester, (meth)acrylic acid 2,2,2-trifluoroethyl ester, (meth)acrylic acid perfluoroethyl ester, (meth)acrylic acid perfluoro-n-propyl ester, (meth)acrylic acid perfluoro-i-propyl ester, (meth)acrylic acid perfluoro-n-butyl ester, (meth)acrylic acid perfluoro-i-butyl ester, (meth)acrylic acid perfluoro-t-butyl ester, (meth)acrylic acid 2-(1,1,1,3,3,3-hexafluoropropyl) ester, (meth)acrylic acid 1-(2,2,3,3,4,4,5,5-octafluoropentyl) ester, (meth)acrylic acid perfluorocyclohexylmethyl ester, (meth
- the proportion of structural unit (Ea) with respect to the total structural units constituting the fluorine-containing polymer (E) is preferably 5 mol % to 80 mol %, more preferably 10 mol % to 60 mol %, and still more preferably 15 mol % to 40 mol %.
- a larger dynamic contact angle on the surface of the resist film may be attained in an exposure through a liquid immersion medium.
- the structural unit (Eb) is represented by the following formula (7b).
- the hydrophobicity thereof may be enhanced, leading to a further improvement of the dynamic contact angle on the surface of the resist film formed from the photoresist composition.
- R F represents a hydrogen atom, a methyl group or a trifluoromethyl group
- R 19 represents a hydrocarbon group having 1 to 20 carbon atoms and a valency of (s+1), which may further include an oxygen atom, a sulfur atom, —NR′—, a carbonyl group, —CO—O— or —CO—NH— at an end of R 19 on the R 2 ° side, wherein R′ represents a hydrogen atom or a monovalent organic group
- R 20 represents a single bond, a divalent linear hydrocarbon group having 1 to 10 carbon atoms or a divalent aliphatic cyclic hydrocarbon group having 4 to 20 carbon atoms
- X 2 represents a divalent linear hydrocarbon group having 1 to 20 carbon atoms and having at least one fluorine atom
- a 1 represents an oxygen atom, —NR′′—, —CO—O—* or —SO 2 —O—*, wherein R′′ represents a hydrogen atom or a
- R 21 preferably represents a hydrogen atom in light of the possibility of an increase of the solubility of the fluorine-containing polymer (E) in an alkaline developer solution.
- Examples of the monovalent organic group which may be represented by R 21 include hydrocarbon groups having 1 to 30 carbon atoms and optionally including an acid-labile group, an alkali-labile group or a substituent, and the like.
- Examples of the structural unit (Eb) include structural units represented by the following formulae (7b-1) to (7b-3), and the like.
- R 19′ represents a divalent linear, branched or cyclic saturated or unsaturated hydrocarbon group having 1 to 20 carbon atoms; and R F , X 2 , R 21 and s are as defined in the above formula (7b), wherein in a case where s is 2 or 3, a plurality of X 2 s are identical to or different with each other, and a plurality of R 21 s are identical to or different with each other.
- the proportion of the structural unit (7b) with respect to the total structural units constituting the fluorine-containing polymer (E) is preferably 0 mol % to 90 mol %, more preferably 5 mol % to 85 mol %, and still more preferably 10 mol % to 80 mol %.
- the proportion of the structural unit (7b) falls within the above range, the degree of a decrease of the dynamic contact angle on the surface of the resist film formed from the photoresist composition in a development with an alkali may be reduced.
- the fluorine-containing polymer (E) may have, in addition to the structural units (Ea) and (Eb), a structural unit that includes an acid-labile group (hereinafter, may be also referred to as “structural unit (Ec)”) (except for those corresponding to the structural unit (Eb)).
- structural unit (Ec) a structural unit that includes an acid-labile group
- the configuration of the resulting resist pattern may be more favorable.
- the structural unit (Ec) include the structural unit (I) mentioned hereinabove in connection with the polymer (A), and the like.
- the proportion of the structural unit (Ec) with respect to the total structural units constituting the fluorine-containing polymer (E) is preferably 10 mol % to 90 mol %, more preferably 20 mol % to 85 mol %, still more preferably 30 mol % to 80 mol %, and particularly preferably 50 mol % to 75 mol %.
- the proportion of the structural unit (Ec) is less than the lower limit, formation of development defects in the resist pattern may not be sufficiently inhibited.
- the proportion of the structural unit (Ec) is greater than the upper limit, the hydrophobicity of the surface of the resulting resist film may be deteriorated.
- the fluorine-containing polymer (E) may have, in addition to the structural units described above, other structural unit, such as, for example: a structural unit that includes an alkali-soluble group, a structural unit that includes at least one structure selected from the group consisting of a lactone structure, a cyclic carbonate structure and a sultone structure, a structural unit that includes an alicyclic group, etc.
- a structural unit that includes an alkali-soluble group include a carboxy group, a sulfonamide group, a sulfo group, and the like.
- Examples of the structural unit that includes at least one structure selected from the group consisting of a lactone structure, a cyclic carbonate structure and a sultone structure include the structural unit (II) mentioned hereinabove in connection with the polymer (A), and the like.
- the proportion of the other structural unit with respect to the total structural units constituting the fluorine-containing polymer (E) is typically no greater than 30 mol %, and preferably no greater than 20 mol %.
- the proportion of the other structural unit is greater than the upper limit, the pattern formability of the photoresist composition may be deteriorated.
- the amount of the fluorine-containing polymer (E) in the photoresist composition with respect to 100 parts by mass of the polymer (A) is preferably 0 to 20 parts by mass, more preferably 0.5 parts by mass to 15 parts by mass, and still more preferably 1 part by mass to 10 parts by mass.
- the amount of the fluorine-containing polymer (E) is greater than the upper limit, the pattern formability of the photoresist composition may be deteriorated.
- the photoresist composition according to the embodiment of the present invention typically contains (F) a solvent.
- the solvent (F) is not particularly limited as long as it is capable of dissolving or dispersing at least the polymer (A), the acid generator (B) and the acid diffusion control agent (C), as well as the other acid diffusion controller (D) contained as desired, and the like.
- the solvent (F) is exemplified by an alcohol solvent, an ether solvent, a ketone solvent, an amide solvent, an ester solvent, a hydrocarbon solvent, and the like.
- Examples of the alcohol solvent include:
- monohydric alcohol solvents such as methanol, ethanol, n-propanol, iso-propanol, n-butanol, iso-butanol, sec-butanol, tert-butanol, n-pentanol, iso-pentanol, 2-methylbutanol, sec-pentanol, tert-pentanol, 3-methoxybutanol, n-hexanol, 2-methylpentanol, sec-hexanol, 2-ethylbutanol, sec-heptanol, 3-heptanol, n-octanol, 2-ethylhexanol, sec-octanol, n-nonyl alcohol, 2,6-dimethyl-4-heptanol, n-decanol, sec-undecyl alcohol, trimethylnonyl alcohol, sec-tetradecyl alcohol, sec
- polyhydric alcohol solvents such as ethylene glycol, 1,2-propylene glycol, 1,3-butylene glycol, 2,4-pentanediol, 2-methyl-2,4-pentanediol, 2,5-hexanediol, 2,4-heptanediol, 2-ethyl-1,3-hexanediol, diethylene glycol, dipropylene glycol, triethylene glycol and tripropylene glycol;
- polyhydric alcohol partial ether solvents such as ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, ethylene glycol monopropyl ether, ethylene glycol monobutyl ether, ethylene glycol monohexyl ether, ethylene glycol monophenyl ether, ethylene glycol mono-2-ethylbutyl ether, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, diethylene glycol monopropyl ether, diethylene glycol monobutyl ether, diethylene glycol monohexyl ether, propylene glycol monomethyl ether, propylene glycol monoethyl ether, propylene glycol monopropyl ether, propylene glycol monobutyl ether, dipropylene glycol monomethyl ether, dipropylene glycol monoethyl ether and dipropylene glycol monopropyl ether; and the like.
- ether solvent examples include:
- dialkyl ether solvents such as diethyl ether, dipropyl ether and dibutyl ether;
- cyclic ether solvents such as tetrahydrofuran and tetrahydropyran
- aromatic ring-containing ether solvents such as diphenyl ether and anisole (methyl phenyl ether); and the like.
- ketone solvent examples include:
- linear ketone solvents such as acetone, methyl ethyl ketone, methyl n-propyl ketone, methyl n-butyl ketone, diethyl ketone, methyl iso-butyl ketone, 2-heptanone (methyl n-pentyl ketone), ethyl n-butyl ketone, methyl n-hexyl ketone, di-iso-butyl ketone and trimethylnonanone;
- cyclic ketone solvents such as cyclopentanone, cyclohexanone, cycloheptanone, cyclooctanone and methylcyclohexanone;
- amide solvent examples include:
- cyclic amide solvents such as N,N′-dimethylimidazolidinone and N-methylpyrrolidone
- linear amide solvents such as N-methylformamide, N,N-dimethylformamide, N,N-diethylformamide, acetamide, N-methylacetamide, N,N-dimethylacetamide and N-methylpropionamide; and the like.
- ester solvent examples include:
- acetic acid ester solvents such as methyl acetate, ethyl acetate, n-propyl acetate, iso-propyl acetate, n-butyl acetate, iso-butyl acetate, sec-butyl acetate, n-pentyl acetate, i-pentyl acetate, sec-pentyl acetate, 3-methoxybutyl acetate, methylpentyl acetate, 2-ethylbutyl acetate, 2-ethylhexyl acetate, benzyl acetate, cyclohexyl acetate, methylcyclohexyl acetate and n-nonyl acetate;
- polyhydric alcohol partial ether acetate solvents such as ethylene glycol monomethyl ether acetate, ethylene glycol monoethyl ether acetate, diethylene glycol monomethyl ether acetate, diethylene glycol monoethyl ether acetate, diethylene glycol mono-n-butyl ether acetate, propylene glycol monomethyl ether acetate, propylene glycol monoethyl ether acetate, propylene glycol monopropyl ether acetate, propylene glycol monobutyl ether acetate, dipropylene glycol monomethyl ether acetate and dipropylene glycol monoethyl ether acetate;
- carbonate solvents such as diethyl carbonate
- hydrocarbon solvent examples include:
- aliphatic hydrocarbon solvents such as n-pentane, iso-pentane, n-hexane, iso-hexane, n-heptane, iso-heptane, 2,2,4-trimethylpentane, n-octane, iso-octane, cyclohexane and methylcyclohexane;
- aromatic hydrocarbon solvents such as benzene, toluene, xylene, mesitylene, ethylbenzene, trimethylbenzene, methylethylbenzene, n-propylbenzene, iso-propylbenzene, diethylbenzene, iso-butylbenzene, triethylbenzene, di-iso-propylbenzene and n-amylnaphthalene; and the like.
- aromatic hydrocarbon solvents such as benzene, toluene, xylene, mesitylene, ethylbenzene, trimethylbenzene, methylethylbenzene, n-propylbenzene, iso-propylbenzene, diethylbenzene, iso-butylbenzene, triethylbenzene, di-iso-propylbenzene and n-amylnaphthalene;
- the photoresist composition may contain one, or two or more types of the solvent (F).
- the photoresist composition may contain other optional component(s) in addition to the aforementioned components (A) to (F).
- the other optional component(s) may be exemplified by an uneven distribution accelerator, a surfactant, an alicyclic skeleton-containing compound, a sensitizing agent, and the like. These other optional components each may be used alone, or in combination of two or more types thereof.
- the uneven distribution accelerator exhibits the effect of more efficiently segregating the fluorine-containing polymer (E) on the surface of the resist film.
- the amount of the fluorine-containing polymer (E) added may be reduced as compared with conventional levels.
- the elution of the components from the resist film into a liquid immersion liquid may be further suppressed and/or an exposure through a liquid immersion medium may be carried out at a higher speed by high speed scanning, without deteriorating characteristics such as the rectangularity of a cross-sectional shape, the LWR performance, the resolving ability and the depth of focus; as a result, the hydrophobicity of the surface of the resist film, which inhibits defects attributed to the liquid immersion, e.g., watermark defects, may be enhanced.
- a low molecular weight compound having a relative permittivity of no less than 30 and no greater than 200, and a boiling point at 1 atm of no less than 100° C. may be used.
- the compound is specifically exemplified by a lactone compound, a carbonate compound, a nitrile compound, a polyhydric alcohol, and the like.
- lactone compound examples include ⁇ -butyrolactone, valerolactone, mevalonic lactone, norbornanelactone, and the like.
- Examples of the carbonate compound include propylene carbonate, ethylene carbonate, butylene carbonate, vinylene carbonate, and the like.
- nitrile compound examples include succinonitrile, and the like.
- polyhydric alcohol examples include glycerin, and the like.
- the amount of the uneven distribution accelerator in the photoresist composition with respect to 100 parts by mass of the total polymer(s) is preferably 10 parts by mass to 500 parts by mass, more preferably 15 parts by mass to 300 parts by mass, and still more preferably 20 parts by mass to 100 parts by mass.
- the surfactant exhibits the effect of improving a coating property, striation, developability, and the like.
- the surfactant include nonionic surfactants such as polyoxyethylene lauryl ether, polyoxyethylene stearyl ether, polyoxyethylene oleyl ether, polyoxyethylene n-octylphenyl ether, polyoxyethylene n-nonylphenyl ether, polyethylene glycol dilaurate and polyethylene glycol distearate; and commercially available products such as KP341 (manufactured by Shin-Etsu Chemical Co., Ltd.), Polyflow No. 75 and No.
- the amount of the surfactant in the photoresist composition with respect to 100 parts by mass of the polymer (A) is typically no greater than 2 parts by mass.
- the alicyclic skeleton-containing compound exhibits the effect of improving dry etching resistance, a pattern configuration, adhesiveness to substrate, and the like.
- Examples of the alicyclic skeleton-containing compound include:
- adamantane derivatives such as 1-adamantanecarboxylic acid, 2-adamantanone and t-butyl 1-adamantanecarboxylate;
- deoxycholic acid esters such as t-butyl deoxycholate, t-butoxycarbonylmethyl deoxycholate and 2-ethoxyethyl deoxycholate;
- lithocholic acid esters such as t-butyl lithocholate, t-butoxycarbonylmethyl lithocholate and 2-ethoxyethyl lithocholate;
- the amount of the alicyclic skeleton-containing compound in the photoresist composition with respect to 100 parts by mass of the polymer (A) is typically no greater than 5 parts by mass.
- the sensitizing agent exhibits the action of increasing the amount of an acid generated from the acid generating agent (B) and the like, and exerts the effect of improving “apparent sensitivity” of the photoresist composition.
- sensitizing agent examples include carbazoles, acetophenones, benzophenones, naphthalenes, phenols, biacetyl, eosin, rose bengal, pyrenes, anthracenes, phenothiazines, and the like. These sensitizing agents may be used either alone, or in combination of two or more types thereof.
- the amount of the sensitizing agent in the photoresist composition with respect to 100 parts by mass of the polymer (A) is typically no greater than 2 parts by mass.
- the photoresist composition according to the embodiment of the present invention may be prepared, for example, by mixing the polymer (A), the acid generator (B) and the acid diffusion control agent (C), as well as the optional component(s) and the solvent (F) each contained as needed in a predetermined ratio. After the mixing, the photoresist composition is preferably filtered through a filter with a pore size of about 0.2 ⁇ m, for example.
- the solid content concentration of the photoresist composition is typically 0.1% by mass to 50% by mass, preferably 0.5% by mass to 30% by mass, and more preferably 1% by mass to 20% by mass.
- resist film-providing step providing a resist film using the photoresist composition according to the embodiment of the present invention (hereinafter, may be also referred to as “resist film-providing step”);
- Exposure step exposing the resist film (hereinafter, may be also referred to as “exposure step”);
- development step developing the resist film exposed
- a resist pattern can be formed that exhibits superior rectangularity of a cross-sectional shape, decreased LWR and a superior resolving ability, while attaining a greater depth of focus.
- each step will be explained.
- the photoresist composition according to the embodiment of the present invention is coated on a substrate by appropriate coating means such as spin-coating, cast coating and roll coating to provide a resist film.
- the substrate include silicon wafers, wafers covered with silicon dioxide or an antireflective film, and the like.
- prebaking is carried out to permit the solvent present in the coating film to be volatilized, resulting in the formation of the resist film.
- the temperature of PB is typically 60° C. to 140° C., and preferably 80° C. to 120° C.
- the time period of PB is typically 5 sec to 600 sec, and preferably 10 sec to 300 sec.
- the resist film provided in the resist film-providing step is exposed.
- the exposure is carried out, for example, by irradiating the resist film with an exposure light through a photomask (through a liquid immersion medium such as water, as needed).
- the exposure light is exemplified by: an electromagnetic wave such as a visible light ray, an ultraviolet ray, a far ultraviolet ray, an X-ray and a ⁇ -ray; a charged particle ray such as an electron beam and an ⁇ -ray; and the like, in accordance with the line width of the intended pattern.
- an ArF excimer laser beam (wavelength: 193 nm)
- a KrF excimer laser beam (wavelength: 248 nm) and an electron beam
- an ArF excimer laser beam and an electron beam are still more preferred.
- PEB post exposure baking
- This PEB makes the difference of the solubility in a developer solution between at a site subjected to the exposure (light-exposed site) and a site not subjected to the exposure (light-unexposed site).
- the temperature of the PEB is typically 50° C. to 180° C., and preferably 80° C. to 130° C.
- the time period of the PEB is typically 5 sec to 600 sec, and preferably 10 sec to 300 sec.
- the resist film exposed is developed with a developer solution to form a predetermined resist pattern.
- washing with a rinse agent such as water or an alcohol followed by drying is typically carried out.
- examples of the developer solution include aqueous alkali solutions prepared by dissolving at least one type of alkaline compounds such as sodium hydroxide, potassium hydroxide, sodium carbonate, sodium silicate, sodium metasilicate, aqueous ammonia, ethylamine, n-propylamine, diethylamine, di-n-propylamine, triethylamine, methyldiethylamine, ethyldimethylamine, triethanolamine, tetramethylammonium hydroxide (TMAH), pyrrole, piperidine, choline, 1,8-diazabicyclo-[5.4.0]-7-undecene and 1,5-diazabicyclo-[4.3.0]-5-nonene; and the like.
- TMAH tetramethylammonium hydroxide
- the developer solution is exemplified by: an organic solvent such as a hydrocarbon solvent, an ether solvent, an ester solvent, a ketone solvent and an alcohol solvent; and a solvent containing an organic solvent.
- organic solvent include one, or two or more types of the solvents enumerated in connection with the solvent (F) which may be contained in the abovementioned photoresist composition, and the like.
- an ester solvent and a ketone solvent are preferred.
- the ester solvent acetic acid ester solvents are preferred, and n-butyl acetate is more preferred.
- the ketone solvent linear ketones are preferred, and 2-heptanone is more preferred.
- a liquid immersion liquid-insoluble protective film for liquid immersion may be provided on the resist film for the purpose of avoiding a direct contact of the resist film with a liquid immersion liquid before the exposure step.
- the protective film for liquid immersion any one of a solvent-peelable protective film that is peeled by a solvent before the development step (see, for example, Japanese Unexamined Patent Application, Publication No. 2006-227632) and a developer solution-peelable protective film that is peeled concomitantly with the development in the development step (see, for example, WO 2005-069076 and WO 2006-035790) may be used.
- a developer solution-peelable protective film for liquid immersion is preferably used in light of throughput.
- An acid diffusion control agent according to still another embodiment of the present invention contains the compound (1).
- the compound (1) is represented by the above formula (1).
- R 1 , R 2 and R 3 each independently represent a hydrogen atom or a monovalent hydrocarbon group having 1 to 10 carbon atoms, wherein in a case where the monovalent hydrocarbon group is present in a plurality of number, at least two of these hydrocarbon groups optionally taken together represent a ring structure by binding with each other, together with the carbon atom to which the at least two of these hydrocarbon groups bond;
- A represents a group having a valency of n that is obtained by combining: at least one group selected from the group consisting of a hydrogen atom, a linear hydrocarbon group having 1 to 30 carbon atoms and an alicyclic hydrocarbon group having 3 to 30 carbon atoms; at least one group selected from the group consisting of —O—, —CO—, —COO—, —SO 2 O—, —NR—, —NRSO 2 —, —NRSO 2 O— and —NRCO—; and n nitrogen atoms as a binding site to the carbonyl group
- the compound (1) is preferably the compound (2).
- R 1 , R 2 , R 3 and n are as defined in the above formula (1);
- R 4 represents a hydrogen atom or a monovalent hydrocarbon group having 1 to 10 carbon atoms;
- R 5 represents a divalent hydrocarbon group having 1 to 10 carbon atoms, wherein R 4 and R 5 optionally taken together represent an alicyclic structure by binding with each other, together with the nitrogen atom to which R 4 and R 5 bond;
- R 6 represents a group having a valency of n that is obtained by combining: at least one group selected from the group consisting of a hydrogen atom, a linear hydrocarbon group having 1 to 30 carbon atoms and an alicyclic hydrocarbon group having 3 to 30 carbon atoms; and at least one group selected from the group consisting of —O—, —CO—, —COO—, —SO 2 O—, —NR—, —NRSO 2 —, —NRSO 2 O— and —NRCO—, wherein a part or all of hydrogen
- the compound (2) is preferably the compound (3).
- R 1 to R 5 are as defined in the above formula (2);
- R 7 , R 8 and R 9 each independently represent at least one group selected from the group consisting of a hydrogen atom, a linear hydrocarbon group having 1 to 30 carbon atoms and an alicyclic hydrocarbon group having 3 to 30 carbon atoms, or a group that is obtained by combining: the at least one group selected from the group consisting of a hydrogen atom, a linear hydrocarbon group having 1 to 30 carbon atoms and an alicyclic hydrocarbon group having 3 to 30 carbon atoms; and at least one group selected from the group consisting of —O—, —CO—, —COO—, —SO 2 O—, —NR—, —NRSO 2 —, —NRSO 2 O— and —NRCO—, wherein at least two of R 7 , R 8 and R 9 optionally taken together represent a ring structure by binding with each other, together with the carbon atom to which the at least two of R 7 , R 8 and
- the acid diffusion control agent according to the embodiment of the present invention has been explained in connection with the acid diffusion control agent (C) contained in the photoresist composition.
- a compound according to yet still another embodiment of the present invention is represented by the above formula (3).
- R 1 , R 2 and R 3 each independently represent a hydrogen atom or a monovalent hydrocarbon group having 1 to 10 carbon atoms, wherein in a case where the monovalent hydrocarbon group is present in a plurality of number, at least two of these hydrocarbon groups optionally taken together represent a ring structure by binding with each other, together with the carbon atom to which the at least two of these hydrocarbon groups bond;
- R 4 represents a hydrogen atom or a monovalent hydrocarbon group having 1 to 10 carbon atoms;
- R 5 represents a divalent hydrocarbon group having 1 to 10 carbon atoms, wherein R 4 and R 5 optionally taken together represent an alicyclic structure by binding with each other, together with the nitrogen atom to which R 4 and R 5 bond;
- R 7 , R 8 and R 9 each independently represent at least one group selected from the group consisting of a hydrogen atom, a linear hydrocarbon group having 1 to 30 carbon atoms and an alicyclic hydrocarbon group having 3 to 30 carbon atoms, or a group
- the compound according to the embodiment of the present invention is the aforementioned compound (i), and has been explained in the section of the acid diffusion control agent (C) in connection with the photoresist composition.
- L represents C and R ⁇ represents an adamantyl group, an ethoxycarbonylmethyl group or a camphor group; or L represents S ⁇ O and R ⁇ represents a methyl group.
- a monomer solution was prepared by dissolving 9.01 g (50 mol %) of the compound (M-1) and 10.99 g (50 mol %) of the compound (M-2) in 40 g of 2-butanone, and further dissolving therein 0.81 g (5 mol % with respect to the total mol number of the compounds) of AIBN as a polymerization initiator.
- a 100 mL three-neck flask containing 20 g of 2-butanone was purged with a nitrogen gas for 30 min, and then heated to 80° C. with stirring, and the monomer solution prepared above was added dropwise over 3 hrs using a dropping funnel.
- the time of the start of the dropwise addition was regarded as the time of the start of the polymerization reaction, and the polymerization reaction was allowed to proceed for 6 hrs.
- the polymerization reaction solution was water-cooled to 30° C. or below.
- the cooled polymerization reaction solution was poured into 400 g of methanol, and the deposited white powder was filtered off.
- the filtered white powder was washed twice with 80 g of methanol, followed by filtration, and dried at 50° C. for 17 hrs to obtain a polymer (A-1) as a white powder (recovered amount: 15.6 g; yield: 78%).
- the polymer (A-1) had an Mw of 7,200 and an Mw/Mn of 1.52.
- the polymer (A-2) had an Mw of 10,000 and an Mw/Mn of 2.1.
- the content of low molecular weight components in the polymer (A-2) was 0.05% by mass.
- a monomer solution was prepared by dissolving 79.9 g (70 mol %) of the compound (M-1) and 20.91 g (30 mol %) of the compound (M-3) in 100 g of 2-butanone, and further dissolving 4.77 g of dimethyl 2,2′-azobisisobutyrate as a polymerization initiator.
- a 1,000 mL three-neck flask containing 100 g of 2-butanone was purged with nitrogen gas for 30 min, and then heated to 80° C. with stirring, and the monomer solution prepared above was added dropwise over 3 hrs using a dropping funnel.
- the time of the start of the dropwise addition was regarded as the time of the start of the polymerization reaction, and the polymerization reaction was allowed to proceed for 6 hrs.
- the polymerization reaction solution was water-cooled to 30° C. or below.
- the polymerization reaction solution was transferred to a 2 L separatory funnel, and then the polymerization reaction solution was homogeneously diluted with 150 g of n-hexane.
- Into the diluted polymerization reaction solution was charged 600 g of methanol and mixed therewith, then 30 g of distilled water was charged, followed by further stirring, and then the mixture was left to stand for 30 min.
- the polymer (E-1) had an Mw of 7,200 and an Mw/Mn of 2.00.
- the content of low molecular weight components in the polymer (E-1) was 0.07% by mass.
- triphenylsulfonium 2-(adamantan-1-yl)-1,1-difluoroethane-1-sulfonate compound represented by the following formula (B-1)
- CC-1 N-t-amyloxycarbonyl-4-hydroxypiperidine (compound represented by the following formula (CC-1))
- F-1 propylene glycol monomethyl ether acetate
- a photoresist composition (J-1) was prepared by mixing 100 parts by mass of (A-1) as the polymer (A), 8.5 parts by mass of (B-1) as the acid generating agent (B), 30 mol % (mol % with respect to the acid generating agent (B)) of (C-1) as the acid diffusion control agent (C), 3 parts by mass of (E-1) as the fluorine atom-containing polymer (E), 2,240 parts by mass of (F-1) and 960 parts by mass (F-2) as the solvent (F), as well as 30 parts by mass of (G-1) as the uneven distribution accelerator (G).
- Photoresist compositions (J-2) to (J-4) and (CJ-1) were prepared in a similar manner to Example 5 except that the type and the content of each component were as specified in Table 1.
- An underlayer antireflective film having a film thickness of 105 nm was provided on the surface of a 12-inch silicon wafer by coating a composition for forming an underlayer antireflective film (ARC66, manufactured by Brewer Science) on the surface of the 12-inch silicon wafer using a spin coater (CLEAN TRACK ACT12, manufactured by Tokyo Electron Limited), and thereafter heating the same to 205° C. for 60 sec.
- ARC66 underlayer antireflective film
- a spin coater CLEAN TRACK ACT12, manufactured by Tokyo Electron Limited
- Each photoresist composition was coated on the underlayer antireflective film using the spin coater, and subjected to PB at 90° C. 60 sec. Thereafter, cooling was carried out at 23° C. for 30 sec to provide a resist film having a film thickness of 90 nm.
- the resist film was exposed using an ArF excimer laser Immersion Scanner (NSR-S610C, manufactured by NIKON) through a 40 nm line-and-space (1L1S) mask pattern, under optical conditions involving NA of 1.3 and dipole (Sigma: 0.977/0.782).
- NSR-S610C ArF excimer laser Immersion Scanner
- TMAH 2.38% by mass aqueous TMAH solution
- a negative resist pattern was formed in a similar manner to the abovementioned “Development with Alkali” except that n-butyl acetate was used in place of the 2.38% by mass aqueous TMAH solution as the developer solution and the step of washing with water was skipped.
- the photoresist compositions were evaluated through measurements for resist patterns formed therefrom. The results of the evaluations are shown in Table 2. The symbol “-” in Table 2 indicates a reference for evaluation. A scanning electron microscope (S-9380, manufactured by Hitachi High-Technologies Corporation) was used in the measurement of the resist patterns.
- the resist pattern formed was observed from above the pattern using the scanning electron microscope.
- the line width was measured at arbitrary points of 50 in total, and a 3 Sigma value was determined from the distribution of the measurements, and the value was designated as “LWR performance”.
- the smaller value indicates a more favorable LWR performance.
- the LWR performance was evaluated to be “A” (favorable) in the case of an improvement of the LWR performance by no less than 10% as compared with the photoresist composition according to Comparative Example 1 (which means a value indicative of the LWR performance being no greater than 90% of a value for the photoresist composition according to Comparative Example 1) being found, and to be “B” (unfavorable) in the case of an improvement of the LWR performance by less than 10% being found.
- a dimension of the minimum resist pattern which was resolved at an optimum exposure dose was designated as “resolving ability”.
- the smaller value indicates a more favorable resolving ability.
- the resolving ability was evaluated to be “A” (favorable) in the case of an improvement of the resolving ability by no less than 10% as compared with the photoresist composition according to Comparative Example 1 (which means a value indicative of the resolving ability being no greater than 90% of a value for the photoresist composition according to Comparative Example 1) being found, and to be “B” (unfavorable) in the case of an improvement of the resolving ability by less than 10% being found.
- the cross-sectional shape of the resist pattern which was resolved at the optimum exposure dose was observed, and a line width Lb in the middle portion of the resist pattern and a line width La at the top of the resist pattern were measured.
- the rectangularity of the cross-sectional shape was evaluated to be “A” (favorable) in a case where the La/Lb value fell within a range of no less than 0.9 and no greater than 1.1, and to be “B” (unfavorable) in a case where the La/Lb value was less than 0.9 or greater than 1.1.
- the dimension when the focus was shifted along the depth direction was observed, and a latitude of the depth direction in which the pattern dimension fell within the range of 90% to 110% of the reference while not accompanied by a bridge and/or residue was measured, and the measurement result was defined as the “depth of focus”.
- the greater value indicates a more favorable depth of focus.
- the depth of focus was evaluated to be “A” (favorable) in the case of an improvement of the depth of focus by no less than 10% as compared with the photoresist composition according to Comparative Example 1 (which means a value indicative of the depth of focus being no less than 110% of a value for the photoresist composition according to Comparative Example 1) being found, and to be “B” (unfavorable) in the case of an improvement of the depth of focus by less than 10% being found.
- a photoresist composition (J-5) was prepared by mixing 100 parts by mass of (A-2) as the polymer (A), 20 parts by mass of (B-1) as the acid generating agent (B), 30 mol % (molar ratio with respect to the acid generating agent (B)) of (C-1) as the acid diffusion control agent (C) as well as 4,280 parts by mass of (F-1) and 1,830 parts by mass of (F-2) as the solvent (F).
- Photoresist compositions (J-6) to (J-8) were prepared in a similar manner to Example 11 except that the type and the content of each component were as specified in Table 3.
- Each photoresist composition shown in Table 3 below was coated on the surface of an 8-inch silicon wafer using a spin coater (CLEAN TRACK ACT8, manufactured by Tokyo Electron Limited), and subjected to PB at 90° C. for 60 sec. Thereafter, cooling was carried out at 23° C. for 30 sec, whereby a resist film having a film thickness of 50 nm was provided. Next, this resist film was irradiated with an electron beam using a simplified electron beam writer (HL800D, manufactured by Hitachi, Ltd., power: 50 KeV, electric current density: 5.0 ampere/cm 2 ). After the irradiation, PEB was carried out at 130° C. for 60 sec. Thereafter, a development was carried out at 23° C. for 30 sec using a 2.38% by mass aqueous TMAH solution as a developer solution, followed by washing with water and drying to form a positive resist pattern.
- the photoresist compositions according to Examples enable a resist pattern to be obtained which exhibits superior pattern configuration, decreased LWR and a superior resolving ability, while attaining a greater depth of focus.
- the photoresist composition according to the embodiments of the present invention and the resist pattern-forming method using the photoresist composition enable a resist pattern to be formed that exhibits superior rectangularity of a cross-sectional shape, decreased LWR and a superior resolving ability, while attaining a greater depth of focus.
- the acid diffusion control agent according to the present invention can be suitably used as an acid diffusion control agent component of the photoresist composition.
- the compound according to the present invention can be suitably used as the acid diffusion control agent. Therefore, these can be suitably used in pattern formation involved in the production of semiconductor devices, in which further progress of miniaturization is expected in the future.
Landscapes
- Physics & Mathematics (AREA)
- General Physics & Mathematics (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Architecture (AREA)
- Structural Engineering (AREA)
- Materials For Photolithography (AREA)
- Hydrogenated Pyridines (AREA)
Abstract
Description
- The present invention relates to a photoresist composition, a resist pattern-forming method, an acid diffusion control agent, and a compound.
- In chemically amplified photoresist compositions, an acid is generated from an acid generating agent upon irradiation with an exposure light such as an ArF excimer laser beam and a KrF excimer laser beam at a light-exposed site, and a reaction catalyzed by the acid allows the difference in dissolution rates in a developer solution to be produced between the light-exposed site and a light-unexposed site, thereby enabling a resist pattern to be formed on a substrate.
- Along with miniaturization in processing techniques, such photoresist compositions are required not only to exhibit a superior resolving ability, but also to be superior in a line width roughness (LWR) performance, which is indicative of a variation in the line width of a resist pattern. To address the demand, incorporation of an acid diffusion control agent into the photoresist compositions is employed for the purpose of properly controlling the diffusion of the acid generated from the acid generating agent. In order to improve various performances of the photoresist compositions, various acid diffusion control agents having a specific structure have been investigated (see Japanese Unexamined Patent Application, Publication No. 2001-215689; PCT International Publication No. WO 2011/007780; Japanese Unexamined Patent Application, Publication Nos. 2009-199021, 2006-321770, 2011-141494, and 2011-141495).
- Under such circumstances, in these days when further miniaturization of resist patterns is advancing, it is also demanded to further improve the resolving ability, the LWR performance, and the like, and to increase a depth of focus for the purpose of improving process stability. In addition, in the case of the aforementioned conventional acid diffusion control agents, since the resist pattern formed tends to exhibit a top loss phenomenon and the like, an improvement of the cross-sectional shape of the resist pattern is also demanded. However, the aforementioned conventional photoresist compositions are incapable of meeting these demands.
- The present invention was made in view of the foregoing circumstances, and it is an object of the present invention to provide a photoresist composition that leads to a superior rectangularity of a cross-sectional shape, a superior LWR performance, a superior resolving ability and a favorable depth of focus.
- According to an aspect of the invention made for solving the aforementioned problems, a photoresist composition is provided, containing:
- a polymer including an acid-labile group (hereinafter, may be also referred to as “(A) polymer” or “polymer (A)”),
- a radiation-sensitive acid generator (hereinafter, may be also referred to as “(B) acid generator” or “acid generator (B)”), and
- an acid diffusion control agent (hereinafter, may be also referred to as “(C) acid diffusion control agent” or “acid diffusion control agent (C)”),
- the acid diffusion control agent containing a compound represented by the following formula (1) (hereinafter, may be also referred to as “compound (I)”):
- wherein in the formula (1), R1, R2 and R3 each independently represent a hydrogen atom or a monovalent hydrocarbon group having 1 to 10 carbon atoms, wherein in a case where the monovalent hydrocarbon group is present in a plurality of number, at least two of these hydrocarbon groups optionally taken together represent a ring structure by binding with each other, together with the carbon atom to which the at least two of these hydrocarbon groups bond; A represents a group having a valency of n that is obtained by combining: at least one group selected from the group consisting of a hydrogen atom, a linear hydrocarbon group having 1 to 30 carbon atoms and an alicyclic hydrocarbon group having 3 to 30 carbon atoms; at least one group selected from the group consisting of —O—, —CO—, —COO—, —SO2O—, —NR—, —NRSO2—, —NRSO2O— and —NRCO—; and n nitrogen atoms as a binding site to the carbonyl group in the above formula (1), wherein a sum of atomic masses of the atoms constituting A is no less than 120, wherein a part or all of hydrogen atoms included in the linear hydrocarbon group and the alicyclic hydrocarbon group are unsubstituted or substituted with a fluorine atom-free group, and wherein R represents a hydrogen atom or a monovalent hydrocarbon group having 1 to 10 carbon atoms; and n is an integer of 1 to 4.
- Since the photoresist composition according to the aspect of the present invention contains the acid diffusion control agent (C) and the acid diffusion control agent (C) contains the compound (1) that has the specific structure, the photoresist composition is superior in rectangularity of a cross-sectional shape, an LWR performance, a resolving ability and a depth of focus. The compound (1) includes a carbamate group. The carbamate group is degraded by an action of an acid generated from the acid generator and the like upon an exposure, and generates a nitrogen atom-containing group. Therefore, the acid diffusion control agent (C) exhibits an excellent acid diffusion controlling function at a light-exposed site, and consequently exhibits superior storage stability. After the degradation of the carbamate group, the compound (1) has been converted to a compound that includes the specific polar group and a nitrogen atom-containing group having a molecular weight falling within a specific range (i.e., a sum of the total atomic mass of the group A and n). Therefore, the compound derived from the compound (1) after the degradation has low volatility and a high affinity to a component, e.g., the polymer, in the photoresist composition. As a result, for example, even after PEB, the compound derived from the compound (1) after the degradation is uniformly distributed in an altitude direction of a resist film formed from the photoresist composition, leading to the suppression of the top loss phenomenon and the like, thereby enabling the formation of a resist pattern exhibiting superior rectangularity of a cross-sectional shape. In addition, it is presumed that when the compound (1) exhibits the aforementioned characteristics, the diffusion of the acid diffusion control agent (C) itself can be inhibited; as a result, the photoresist composition can exhibit a superior LWR performance, a superior resolving ability and a favorable depth of focus.
- It is preferred that the compound represented by the above formula (1) is represented by the following formula (2) (hereinafter, the compound represented by the following formula (2) may be also referred to as “compound (2)”):
- wherein in the formula (2), R1, R2, R3 and n are as defined in the above formula (1); R4 represents a hydrogen atom or a monovalent hydrocarbon group having 1 to 10 carbon atoms; R5 represents a divalent hydrocarbon group having 1 to 10 carbon atoms, wherein R4 and R5 optionally taken together represent an alicyclic structure by binding with each other, together with the nitrogen atom to which R4 and R5 bond; R6 represents a group having a valency of n that is obtained by combining: at least one group selected from the group consisting of a hydrogen atom, a linear hydrocarbon group having 1 to 30 carbon atoms and an alicyclic hydrocarbon group having 3 to 30 carbon atoms; and at least one group selected from the group consisting of —O—, —CO—, —COO—, —SO2O—, —NR—, —NRSO2—, —NRSO2O— and —NRCO—, wherein a part or all of hydrogen atoms included in the linear hydrocarbon group and the alicyclic hydrocarbon group are unsubstituted or substituted with a fluorine atom-free group, wherein R represents a hydrogen atom or a monovalent hydrocarbon group having 1 to 10 carbon atoms, and wherein in the formula (2), a value obtained by the formula of: {(F4+F5+FN)×n+F6} is no less than 120, wherein F4 represents a formula mass of R4, F5 represents a formula mass of R5, FN represents an atomic mass of nitrogen, and F6 represents a formula mass of R6.
- When the acid diffusion control agent (C) has the specific structure, the basicity of the nitrogen atom-containing group generated from the compound (1) can be increased, and the photoresist composition may lead to an improvement of the rectangularity of a cross-sectional shape, the LWR performance, the resolving ability and the depth of focus.
- It is preferred that the compound represented by the above formula (2) is represented by the following formula (3) (hereinafter, the compound represented by the following formula (3) may be also referred to as “compound (3)”):
- wherein in the formula (3), R1 to R5 are as defined in the above formula (2); R7, R8 and R9 each independently represent at least one group selected from the group consisting of a hydrogen atom, a linear hydrocarbon group having 1 to 30 carbon atoms and an alicyclic hydrocarbon group having 3 to 30 carbon atoms, or a group that is obtained by combining: the at least one group selected from the group consisting of a hydrogen atom, a linear hydrocarbon group having 1 to 30 carbon atoms and an alicyclic hydrocarbon group having 3 to 30 carbon atoms; and at least one group selected from the group consisting of —O—, —CO—, —COO—, —SO2O—, —NR—, —NRSO2—, —NRSO2O— and —NRCO—, wherein at least two of R7, R8 and R9 optionally taken together represent a ring structure by binding with each other, together with the carbon atom to which the at least two of R7, R8 and R9 bond; and X represents —O—, —CO—, —COO—, —SO2O—, —NR—, —NRSO2—, —NRSO2O— or —NRCO—, and wherein a sum of formula masses of R4, R5, X, R7, R8 and R9 and atomic masses of the nitrogen and the carbon in the formula (3) is no less than 120.
- According to the photoresist composition, when the acid diffusion control agent (C) has the specific structure, the rectangularity of a cross-sectional shape, the LWR performance, the resolving ability and the depth of focus may be further improved. Moreover, the compound having the specific structure can be easily synthesized from a well-known compound that functions as an acid diffusion control agent through a reaction for forming the functional group X.
- It is preferred that the photoresist composition further contains (D) an acid diffusion controller other than the acid diffusion control agent (C).
- According to the photoresist composition, when the acid diffusion control agent (C) and the acid diffusion control agent other than the acid diffusion control agent (C) are used in combination, the rectangularity of a cross-sectional shape, the LWR performance, the resolving ability and the depth of focus may be improved.
- According to another aspect of the present invention, a resist pattern-forming method is provided, including:
- providing a resist film using the photoresist composition according to the aspect of the present invention;
- exposing the resist film; and
- developing the resist film exposed.
- According to the resist pattern-forming method, since the aforementioned photoresist composition is used, a resist pattern can be formed that exhibits superior rectangularity of a cross-sectional shape, decreased LWR and a superior resolving ability, while attaining a greater depth of focus.
- According to still another aspect of the present invention, an acid diffusion control agent contains the compound (1).
- In the acid diffusion control agent, it is preferred that the compound represented by the above formula (1) is represented by the above formula (2), and it is more preferred that the compound represented by the above formula (2) is represented by the above formula (3).
- Since the acid diffusion control agent contains the compound having the specific structure, the acid diffusion control agent may be suitably used as an acid diffusion control agent component of the photoresist composition, and enables the photoresist composition to lead to an improvement of the rectangularity of a cross-sectional shape, the LWR performance, the resolving ability and the depth of focus.
- According to yet still another aspect of the present invention, a compound (hereinafter, may be also referred to as “compound (i)”) is represented by the following formula (3):
- wherein in the formula (3), R1, R2 and R3 each independently represent a hydrogen atom or a monovalent hydrocarbon group having 1 to 10 carbon atoms, wherein in a case where the monovalent hydrocarbon group is present in a plurality of number, at least two of these hydrocarbon groups optionally taken together represent a ring structure by binding with each other, together with the carbon atom to which the at least two of these hydrocarbon groups bond; R4 represents a hydrogen atom or a monovalent hydrocarbon group having 1 to 10 carbon atoms; R5 represents a divalent hydrocarbon group having 1 to 10 carbon atoms, wherein R4 and R5 optionally taken together represent an alicyclic structure by binding with each other, together with the nitrogen atom to which R4 and R5 bond; R7, R8 and R9 each independently represent at least one group selected from the group consisting of a hydrogen atom, a linear hydrocarbon group having 1 to 30 carbon atoms and an alicyclic hydrocarbon group having 3 to 30 carbon atoms, or a group that is obtained by combining: the at least one group selected from the group consisting of a hydrogen atom, a linear hydrocarbon group having 1 to 30 carbon atoms and an alicyclic hydrocarbon group having 3 to 30 carbon atoms; and at least one group selected from the group consisting of —O—, —CO—, —COO—, —SO2O—, —NR—, —NRSO2—, —NRSO2O— and —NRCO—, wherein at least two of R7, R8 and R9 optionally taken together represent a ring structure by binding with each other, together with the carbon atom to which the at least two of R7, R8 and R9 bond; and X represents —O—, —CO—, —COO—, —SO2O—, —NR—, —NRSO2—, —NRSO2O— or —NRCO—, and wherein a sum of formula masses of R4, R5, X, R7, R8 and R9 and atomic masses of the nitrogen and the carbon in the formula (3) is no less than 120.
- Since the compound (i) has the specific structure, it may be suitably used as, e.g., an acid diffusion control agent component of a photoresist composition, and enables the rectangularity of a cross-sectional shape, the LWR performance, the resolving ability and the depth of focus to be improved. Moreover, the compound (i) can be easily synthesized from a well-known acid diffusion control agent.
- “Organic group” as referred to herein means a group having at least one carbon atom.
- As explained in the foregoing, the photoresist composition and the resist pattern-forming method using the photoresist composition according to the aspects of the present invention enable a resist pattern to be formed that exhibits superior rectangularity of a cross-sectional shape, decreased LWR and a superior resolving ability, while attaining a greater depth of focus. The acid diffusion control agent according to the still another aspect of the present invention can be suitably used as an acid diffusion control agent component of the photoresist composition. Moreover, the compound according to the aspect of the yet still another present invention can be suitably used as the acid diffusion control agent. Therefore, there can be suitably used in pattern formation involved in the production of semiconductor devices, in which further progress of miniaturization is expected in the future.
- A photoresist composition according to an embodiment of the present invention contains (A) a polymer, (B) an acid generator and (C) an acid diffusion control agent. The photoresist composition may further contain, in addition to these components, (D) an acid diffusion control agent other than the acid diffusion control agent (C) (hereinafter, may be also referred to as “(D) other acid diffusion controller” or “other acid diffusion controller (D)”), (E) a fluorine atom-containing polymer and (F) a solvent, each as a favorable component, and may contain other optional component(s) within a range not leading to impairment of the effects of the present invention. Hereinafter, each component will be explained.
- The polymer (A) includes an acid-labile group. The polymer (A) preferably further includes, in addition to a structural unit that includes an acid-labile group (hereinafter, may be also referred to as “structural unit (I)”), a structural unit (II) that includes at least one structure selected from the group consisting of a lactone structure, a cyclic carbonate structure and a sultone structure, and the polymer (A) may further include other structural unit such as a structural unit that includes a polar group. The polymer (A) may include one, or two or more types of each structural unit. Hereinafter, each structural unit will be explained.
- The structural unit (I) includes an acid-labile group. The structural unit (I) is exemplified by a structural unit (I-1) represented by the following formula (4), and the like.
- In the above formula (4), RA represents a hydrogen atom, a fluorine atom, a methyl group or a trifluoromethyl group; and RP represents a monovalent acid-labile group represented by the above formula (p).
- In the above formula (p), Rp1, Rp2 and Rp3 each independently represent an alkyl group having 1 to 4 carbon atoms or a cycloalkyl group having 4 to 20 carbon atoms, wherein Rp2 and Rp3 optionally taken together represent a cycloalkanediyl group having 4 to 20 carbon atoms by binding with each other, together with the carbon atom to which Rp2 and Rp3 bond.
- Structural units represented by the following formulae (4-1) to (4-4) are preferred as the structural unit (I-1).
- In the above formulae (4-1) to (4-4), RA is as defined in the above formula (4); Rp1, Rp2 and Rp3 are as defined in the above formula (p); and i and j are each independently an integer of 1 to 4.
- The structural units represented by the above formulae (4-1) to (4-4) are exemplified by structural units represented by the following formulae, and the like.
- In the above formulae, RA is as defined in the above formula (4).
- The structural unit (I) is preferably the structural unit represented by the above formula (4-1) or the structural unit represented by the formula (4-2), more preferably a structural unit derived from 1-alkyl-1-cyclopentyl (meth)acrylate or a structural unit derived from 2-alkyl-2-adamantyl (meth)acrylate, and still more preferably a structural unit derived from 1-ethyl-1-cyclopentyl (meth)acrylate or a structural unit derived from 2-ethyl-2-adamantyl (meth)acrylate.
- The proportion of the structural unit (I) with respect to the total structural units constituting the polymer (A) is preferably 10 mol % to 100 mol %, more preferably 20 mol % to 80 mol %, and still more preferably 30 mol % to 70 mol %. When the proportion of the structural unit (I) is less than the lower limit, the pattern formability of the photoresist composition may be deteriorated.
- The structural unit (II) includes at least one structure selected from the group consisting of a lactone structure, a cyclic carbonate structure and a sultone structure. When the polymer (A) further includes the structural unit (II), the solubility thereof in a developer solution may be adjusted. In addition, the adhesiveness of a resist pattern formed from the photoresist composition to a substrate may be improved.
- The structural unit (II) is exemplified by structural units represented by the following formulae, and the like.
- In the above formulae, RL1 represents a hydrogen atom, a fluorine atom, a methyl group or a trifluoromethyl group.
- Among these, as the structural unit (II), a structural unit that includes a lactone structure and a structural unit that includes a sultone structure are preferred, and a structural unit that includes a norbornanelactone structure and a structural unit that includes a norbornanesultone structure are more preferred.
- The proportion of the structural unit (II) with respect to the total structural units constituting the polymer (A) is preferably 30 mol % to 80 mol %, more preferably 35 mol % to 70 mol %, and still more preferably 40 mol % to 60 mol %. When the proportion of the structural unit (II) is less than the lower limit, the adhesiveness of a resist pattern formed from the photoresist composition to a substrate may be deteriorated. On the other hand, when the proportion of the structural unit (II) is greater than the upper limit, the pattern formability of the photoresist composition may be deteriorated.
- The polymer (A) may include other structural unit that is different from the structural units (I) and (II). The other structural unit is exemplified by a first other structural unit that includes a polar group, and the like (except for those corresponding to the structural unit (I) and the structural unit (II)). Examples of the polar group include a hydroxy group, a carboxy group, a cyano group, a nitro group, a sulfonamide group, and the like. Among these, a hydroxy group and a carboxy group are preferred, and a hydroxy group is more preferred.
- Examples of the structural unit that includes a polar group include structural units represented by the following formulae, and the like.
- In the above formulae, RB represents a hydrogen atom, a fluorine atom, a methyl group or a trifluoromethyl group.
- The proportion of the structural unit that includes a polar group with respect to the total structural units constituting the polymer (A) is preferably 0 mol % to 80 mol %, more preferably 0 mol % to 75 mol %, and still more preferably 30 mol % to 70 mol %. When the proportion of the structural unit that includes a polar group is greater than the upper limit, the pattern formability of the photoresist composition may be deteriorated.
- The polymer (A) may include a second other structural unit as well as the first structural unit that includes a polar group. The proportion of the second other structural unit with respect to the total structural units constituting the polymer (A) is typically no greater than 30 mol %, and preferably no greater than 20 mol %. When the proportion of the second other structural unit is greater than the upper limit, the pattern formability of the photoresist composition may be deteriorated.
- The content of the polymer (A) with respect to the total solid content of the photoresist composition is typically no less than 70% by mass, preferably no less than 80% by mass, and more preferably no less than 85% by mass.
- The polymer (A) can be synthesized, for example, by polymerizing monomer(s) that give(s) each structural unit in an appropriate solvent using a radical polymerization initiator.
- Examples of the radical polymerization initiator include azo radical initiators such as azobisisobutyronitrile (AIBN), 2,2′-azobis(4-methoxy-2,4-dimethylvaleronitrile), 2,2′-azobis(2-cyclopropylpropionitrile), 2,2′-azobis(2,4-dimethylvaleronitrile) and dimethyl 2,2′-azobisisobutyrate; peroxide radical initiators such as benzoyl peroxide, t-butyl hydroperoxide and cumene hydroperoxide; and the like. Among these, AIBN, dimethyl 2,2′-azobisisobutyrate are preferred, and AIBN are more preferred. These radical initiators may be used either alone, or as a mixture of two or more types thereof.
- Examples of the solvent used in the polymerization include:
- alkanes such as n-pentane, n-hexane, n-heptane, n-octane, n-nonane and n-decane;
- cycloalkanes such as cyclohexane, cycloheptane, cyclooctane, decalin and norbornane;
- aromatic hydrocarbons such as benzene, toluene, xylene, ethylbenzene and cumene;
- halogenated hydrocarbons such as chlorobutanes, bromohexanes, dichloroethanes, hexamethylene dibromide and chlorobenzene;
- saturated carboxylic acid esters such as ethyl acetate, n-butyl acetate, i-butyl acetate and methyl propionate;
- ketones such as acetone, methyl ethyl ketone, 4-methyl-2-pentanone and 2-heptanone;
- ethers such as tetrahydrofuran, diethoxyethanes and diethoxyethanes;
- alcohols such as methanol, ethanol, 1-propanol, 2-propanol and 4-methyl-2-pentanol; and the like. These solvents used in the polymerization may be used either alone, or in combination of two or more types thereof.
- The reaction temperature in the polymerization is typically 40° C. to 150° C., and preferably 50° C. to 120° C. The reaction time period is typically 1 hour to 48 hrs, and preferably 1 hour to 24 hrs.
- Although the polystyrene equivalent weight average molecular weight (Mw) of the polymer (A) as determined by gel permeation chromatography (GPC) is not particularly limited, the Mw is preferably no less than 1,000 and no greater than 50,000, more preferably no less than 2,000 and no greater than 30,000, still more preferably no less than 3,000 and no greater than 20,000, and particularly preferably no less than 5,000 and no greater than 15,000. When the Mw of the polymer (A) is less than the lower limit, the heat resistance of the resulting resist film may be deteriorated. When the Mw of the polymer (A) is greater than the upper limit, the developability of the resist film may be deteriorated.
- The ratio (Mw/Mn) of the Mw to the polystyrene equivalent number average molecular weight (Mn) as determined by GPC of the polymer (A) is typically no less than 1 and no greater than 5, preferably no less than 1 and no greater than 3, and still more preferably no less than 1 and no greater than 2.
- The Mw and Mn of the polymer as used herein are determined using gel permeation chromatography (GPC) under the following conditions:
- GPC columns: G2000HXL×2, G3000HXL×1, and G4000HXL×1 (each manufactured by Tosoh Corporation)
- column temperature: 40° C.
- elution solvent: tetrahydrofuran (manufactured by Wako Pure Chemical Industries, Ltd.)
- flow rate: 1.0 mL/min
- sample concentration: 1.0% by mass
- amount of injected sample: 100 μL
- detector: differential refractometer
- standard substance: mono-dispersed polystyrene.
- The content of low molecular weight components (the low molecular weight components mean components having a molecular weight of less than 1,000) in the polymer (A) is preferably no greater than 0.5% by mass, more preferably no greater than 0.2% by mass, and still more preferably no greater than 0.1% by mass. When the content of the low molecular weight components in the polymer (A) falls within the above range, the photoresist composition may lead to a further improvement of the rectangularity of a cross-sectional shape, the LWR performance, the resolving ability and the depth of focus.
- The content of the low molecular weight components of the polymer as used herein is determined by high performance liquid chromatography (HPLC) using an Intersil ODS-25 μm column (4.6 mmφ×250 mm; manufactured by GL Sciences, Inc.) under the following conditions:
- elution solvent: acrylonitrile/0.1% by mass aqueous phosphoric acid solution
- flow rate: 1.0 mL/min
- sample concentration: 1.0% by mass
- amount of injected sample: 100 μL
- detector: differential refractometer.
- The acid generator (B) generates an acid upon an exposure. The acid-labile group included in the polymer (A) is dissociated by the acid to generate a polar group such as a carboxy group, whereby the solubility of the polymer (A) in a developer solution is altered. The mode of incorporation of the acid generator (B) in the photoresist composition may be in a low molecular weight compound form (hereinafter, may be also referred to as “(B) acid generating agent” or “acid generating agent (B)”, as appropriate), as described later, or in a form of an acid generating group incorporated into the polymer as a part thereof, or in both of these forms.
- The acid generating agent (B) is exemplified by an onium salt compound, an N-sulfonyloxyimide compound, a halogen-containing compound, a diazoketone compound, and the like.
- The onium salt compound is exemplified by a sulfonium salt, a tetrahydrothiophenium salt, an iodonium salt, a phosphonium salt, a diazonium salt, a pyridinium salt, and the like.
- Examples of the sulfonium salt include triphenylsulfonium trifluoromethanesulfonate, triphenylsulfonium nonafluoro-n-butanesulfonate, triphenylsulfonium perfluoro-n-octanesulfonate, triphenylsulfonium 2-bicyclo[2.2.1]hept-2-yl-1,1,2,2-tetrafluoroethanesulfonate, triphenylsulfonium 2-bicyclo[2.2.1]hept-2-yl-1,1-difluoroethanesulfonate, triphenylsulfonium camphorsulfonate, 4-cyclohexylphenyldiphenylsulfonium trifluoromethanesulfonate, 4-cyclohexylphenyldiphenylsulfonium nonafluoro-n-butanesulfonate, 4-cyclohexylphenyldiphenylsulfonium perfluoro-n-octanesulfonate, 4-cyclohexylphenyldiphenylsulfonium 2-bicyclo[2.2.1]hept-2-yl-1,1,2,2-tetrafluoroethanesulfonate, 4-cyclohexylphenyldiphenylsulfonium camphorsulfonate, 4-methanesulfonylphenyldiphenylsulfonium trifluoromethanesulfonate, 4-methanesulfonylphenyldiphenylsulfonium nonafluoro-n-butanesulfonate, 4-methanesulfonylphenyldiphenylsulfonium perfluoro-n-octanesulfonate, 4-methanesulfonylphenyldiphenylsulfonium 2-bicyclo[2.2.1]hept-2-yl-1,1,2,2-tetrafluoroethanesulfonate, 4-methanesulfonylphenyldiphenylsulfonium camphorsulfonate, triphenylsulfonium 1,1,2,2-tetrafluoro-6-(1-adamantanecarbonyloxy)-hexane-1-sulfonate, and the like.
- Examples of the tetrahydrothiophenium salt include 1-(4-n-butoxynaphthalen-1-yl)tetrahydrothiophenium trifluoromethanesulfonate, 1-(4-n-butoxynaphthalen-1-yl)tetrahydrothiophenium nonafluoro-n-butanesulfonate, 1-(4-n-butoxynaphthalen-1-yl)tetrahydrothiophenium perfluoro-n-octanesulfonate, 1-(4-n-butoxynaphthalen-1-yl)tetrahydrothiophenium 2-bicyclo[2.2.1]hept-2-yl-1,1,2,2-tetrafluoroethanesulfonate, 1-(4-n-butoxynaphthalen-1-yl)tetrahydrothiophenium camphorsulfonate, 1-(6-n-butoxynaphthalen-2-yl)tetrahydrothiophenium trifluoromethanesulfonate, 1-(6-n-butoxynaphthalen-2-yl)tetrahydrothiophenium nonafluoro-n-butanesulfonate, 1-(6-n-butoxynaphthalen-2-yl)tetrahydrothiophenium perfluoro-n-octanesulfonate, 1-(6-n-butoxynaphthalen-2-yl)tetrahydrothiophenium 2-bicyclo[2.2.1]hept-2-yl-1,1,2,2-tetrafluoroethanesulfonate, 1-(6-n-butoxynaphthalen-2-yl)tetrahydrothiophenium camphorsulfonate, 1-(3,5-dimethyl-4-hydroxyphenyl)tetrahydrothiophenium trifluoromethanesulfonate, 1-(3,5-dimethyl-4-hydroxyphenyl)tetrahydrothiophenium nonafluoro-n-butanesulfonate, 1-(3,5-dimethyl-4-hydroxyphenyl)tetrahydrothiophenium perfluoro-n-octanesulfonate, 1-(3,5-dimethyl-4-hydroxyphenyl)tetrahydrothiophenium 2-bicyclo[2.2.1]hept-2-yl-1,1,2,2-tetrafluoroethanesulfonate, 1-(3,5-dimethyl-4-hydroxyphenyl)tetrahydrothiophenium camphorsulfonate, and the like.
- Examples of the iodonium salt include diphenyliodonium trifluoromethanesulfonate, diphenyliodonium nonafluoro-n-butanesulfonate, diphenyliodonium perfluoro-n-octanesulfonate, diphenyliodonium 2-bicyclo[2.2.1]hept-2-yl-1,1,2,2-tetrafluoroethanesulfonate, diphenyliodonium camphorsulfonate, bis(4-t-butylphenyl)iodonium trifluoromethanesulfonate, bis(4-t-butylphenyl)iodonium nonafluoro-n-butanesulfonate, bis(4-t-butylphenyl)iodonium perfluoro-n-octanesulfonate, bis(4-t-butylphenyl)iodonium 2-bicyclo[2.2.1]hept-2-yl-1,1,2,2-tetrafluoroethanesulfonate, bis(4-t-butylphenyl)iodonium camphorsulfonate, and the like.
- Examples of the N-sulfonyloxyimide compound include N-(trifluoromethanesulfonyloxy)bicyclo[2.2.1]hept-5-ene-2,3-dicarboxyimide, N-(nonafluoro-n-butanesulfonyloxy)bicyclo[2.2.1]hept-5-ene-2,3-dicarboxyimide, N-(perfluoro-n-octanesulfonyloxy)bicyclo[2.2.1]hept-5-ene-2,3-dicarboxyimide, N-(2-bicyclo[2.2.1]hept-2-yl-1,1,2,2-tetrafluoroethanesulfonyloxy)bicyclo[2.2.1]hept-5-ene-2,3-dicarboxyimide, N-(2-(3-tetracyclo[4.4.0.12,5.17,10]dodecanyl)-1,1-difluoroethanesulfonyloxy)bicyclo[2.2.1]hept-5-ene-2,3-dicarboxyimide, N-(camphorsulfonyloxy)bicyclo[2.2.1]hept-5-ene-2,3-dicarboxyimide, and the like.
- Among these, as the acid generating agent (B), an onium salt compound is preferred, a sulfonium salt is more preferred, and triphenylsulfonium 2-bicyclo[2.2.1]hept-2-yl-1,1-difluoroethanesulfonate is still more preferred.
- In a case where the acid generator (B) is the acid generating agent (B), the amount of the acid generator (B) with respect to 100 parts by mass of the polymer (A) is preferably no less than 0.1 parts by mass and no greater than 30 parts by mass, more preferably no less than 0.5 parts by mass and no greater than 20 parts by mass, and still more preferably no less than 1 part by mass and no greater than 15 parts by mass in light of attaining the sensitivity and developability of the photoresist composition. When the amount of the acid generating agent (B) falls within the above range, the sensitivity and developability of the photoresist composition may be improved. One, or two or more types of the acid generator (B) may be used.
- The acid diffusion control agent (C) contains the compound (1). When the photoresist composition contains the acid diffusion control agent (C) in addition to the polymer (A) and the acid generator (B), the photoresist composition leads to a superior rectangularity of a cross-sectional shape, a superior LWR performance, a superior resolving ability and a favorable depth of focus. One, or two or more types of the acid diffusion control agent (C) may be used.
- The compound (1) is represented by the above formula (1).
- In the above formula (1), R1, R2 and R3 each independently represent a hydrogen atom or a monovalent hydrocarbon group having 1 to 10 carbon atoms, wherein in a case where the monovalent hydrocarbon group is present in a plurality of number, at least two of these hydrocarbon groups optionally taken together represent a ring structure by binding with each other, together with the carbon atom to which the at least two of these hydrocarbon groups bond; A represents a group having a valency of n that is obtained by combining: at least one group selected from the group consisting of a hydrogen atom, a linear hydrocarbon group having 1 to 30 carbon atoms and an alicyclic hydrocarbon group having 3 to 30 carbon atoms; at least one group selected from the group consisting of —O—, —CO—, —COO—, —SO2O—, —NR—, —NRSO2—, —NRSO2O— and —NRCO—; and n nitrogen atoms as a binding site to the carbonyl group in the above formula (1), wherein a sum of atomic masses of the atoms constituting A is no less than 120, wherein a part or all of hydrogen atoms included in the linear hydrocarbon group and the alicyclic hydrocarbon group are unsubstituted or substituted with a fluorine atom-free group, and wherein R represents a hydrogen atom or a monovalent hydrocarbon group having 1 to 10 carbon atoms; and n is an integer of 1 to 4.
- The monovalent hydrocarbon group having 1 to 10 carbon atoms which may be represented by R1, R2 or R3 is exemplified by a monovalent linear hydrocarbon group having 1 to 10 carbon atoms, a monovalent alicyclic hydrocarbon group having 3 to 10 carbon atoms, a monovalent aromatic hydrocarbon group having 6 to 10 carbon atoms, and the like.
- Examples of the monovalent linear hydrocarbon group having 1 to 10 carbon atoms include:
- alkyl groups such as a methyl group, an ethyl group, a n-propyl group, an i-propyl group, a n-butyl group, an i-butyl group, a sec-butyl group and a t-butyl group;
- alkenyl groups such as an ethenyl group, a propenyl group and a butenyl group;
- alkynyl groups such as an ethynyl group, a propynyl group and a butynyl group; and the like.
- Examples of the monovalent alicyclic hydrocarbon group having 3 to 10 carbon atoms include:
- monocyclic cycloalkyl groups such as a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group and a cyclodecyl group;
- polycyclic cycloalkyl groups such as a norbornyl group, an adamantyl group and a tricyclodecyl group;
- monocyclic cycloalkenyl groups such as a cyclopentenyl group and a cyclohexenyl group;
- polycyclic cycloalkenyl groups such as a norbornenyl group and a tricyclodecenyl group; and the like.
- Examples of the monovalent aromatic hydrocarbon group having 6 to 10 carbon atoms include:
- aryl groups such as a phenyl group, a tolyl group, a xylyl group, a mesityl group and a naphthyl group;
- aralkyl groups such as a benzyl group, a phenethyl group and a phenylpropyl group; and the like.
- Examples of the ring structure which may be taken together represented by at least two of the hydrocarbon groups by binding with each other include:
- monocyclic cycloalkane structures such as a cyclobutane structure, a cyclopentane structure, a cyclohexane structure, a cyclooctane structure and a cyclodecane structure and;
- polycyclic cycloalkane structures such as a bicyclo[2.2.1]heptane structure, a bicyclo[2.2.2]octane structure, an adamantane structure and a tricyclodecane structure; and the like.
- Among these, R1, R2 and R3 represent preferably a hydrogen atom or a linear hydrocarbon group, more preferably a hydrogen atom or an alkyl group, still more preferably an alkyl group, and particularly preferably a methyl group or an ethyl group.
- The group constituted with R1, R2, R3 and the carbon atom to which R1, R2 and R3 bond is preferably a t-butyl group or a t-amyl group.
- Examples of the linear hydrocarbon group having 1 to 30 carbon atoms that constitutes A include groups obtained by eliminating at least one hydrogen atom from a linear hydrocarbon such as:
- an alkane such as methane, ethane, propane, butane, isobutane, n-pentane, isopentane, n-hexane and isohexane;
- an alkene such as ethene, propene, n-butene, isobutene, n-pentene and isopentene;
- an alkyne such as ethyne, propyne, butyne and pentyne; and the like.
- Examples of the alicyclic hydrocarbon group having 3 to 30 carbon atoms that constitutes A include groups obtained by eliminating at least one hydrogen atom from an alicyclic hydrocarbon such as:
- a monocyclic cycloalkane such as cyclopropane, cyclobutane, cyclopentane, cyclohexane, cyclooctane and cyclodecane;
- a polycyclic cycloalkane such as norbornane, adamantane and tricyclodecane;
- a monocyclic cycloalkene such as cyclopropene, cyclobutene, cyclopentene, cyclohexene, cyclooctene and cyclodecene;
- a polycyclic cycloalkene such as norbornene and tricyclodecene; and the like.
- Examples of the fluorine atom-free substituent which may be included in the linear hydrocarbon group and the alicyclic hydrocarbon group include a cyano group, a nitro group, and the like.
- Examples of the group that is obtained by combining: at least one group selected from the group consisting of a hydrogen atom, the linear hydrocarbon group and the alicyclic hydrocarbon group; and at least one group selected from the group consisting of —O—, —CO—, —COO—, —SO2O—, —NR—, —NRSO2—, —NRSO2O— and —NRCO—, which constitute A, include cyclic ether groups, cyclic ketone groups, lactone groups, sultone groups, cyclic amino groups, cyclic sulfonamide groups, cyclic oxysulfonamide groups, lactam groups, alkoxy groups, acyl groups, acyloxy groups, alkylsulfonyloxy groups, alkoxysulfonyl groups, alkylamino groups, dialkylamino groups, alkoxyalkyl groups, acylalkyl groups, acyloxyalkyl groups, alkoxyalkyl groups, alkylsulfonyloxyalkyl groups, alkyliminosulfonyl groups, alkylsulfonylamidoalkyl groups, alkyliminosulfonyloxyalkyl groups, alkoxysulfonylamidoalkyl groups, alkyliminocarbonylalkyl groups, alkylcarbonyliminoalkyl groups, a hydroxy group, a formyl group, a carboxy group, a sulfo group, an amino group, and the like.
- Examples of the monovalent hydrocarbon group having 1 to 10 carbon atoms which may be represented by R include groups similar to those exemplified as the monovalent hydrocarbon group having 1 to 10 carbon atoms in connection with R1, R2 and R3, as described above, and the like.
- Preferably, n is an integer of 1 to 3, more preferably 1 or 2, and still more preferably 1 in light of the ease in synthesis of the compound (1).
- The lower limit of the sum of the atomic masses of the atoms constituting A is 120, preferably 150, more preferably 200, still more preferably 250, and particularly preferably 290. When the sum of the atomic masses of the atoms constituting A is less than the lower limit, the volatility of the compound generated from the compound (1) after the exposure tends to be elevated, and as a result, the photoresist composition may lead to deterioration of the rectangularity of a cross-sectional shape.
- The upper limit of the sum of the atomic masses of the atoms constituting A is preferably 1,000, more preferably 800, still more preferably 600, and particularly preferably 500. When the sum of the atomic masses of the atoms constituting A is greater than the upper limit, the dispersibility of the compound (1) in the resist film may be reduced, resulting in the tendency that the rectangularity of a cross-sectional shape, the LWR performance, the resolving ability and the depth of focus of the photoresist composition are deteriorated.
- The compound (1) is exemplified by compounds represented by the following formulae (i1) to (i21) (hereinafter, may be also referred to as “compounds (i1) to (i-21)”), and the like.
- The compound (1) is preferably the compound represented by the above formula (2) (hereinafter, may be also referred to as “compound (2)”).
- In the above formula (2), R1, R2, R3 and n are as defined in the above formula (1); R4 represents a hydrogen atom or a monovalent hydrocarbon group having 1 to 10 carbon atoms; R5 represents a divalent hydrocarbon group having 1 to 10 carbon atoms, wherein R4 and R5 optionally taken together represent an alicyclic structure by binding with each other, together with the nitrogen atom to which R4 and R5 bond; R6 represents a group having a valency of n that is obtained by combining: at least one group selected from the group consisting of a hydrogen atom, a linear hydrocarbon group having 1 to 30 carbon atoms and an alicyclic hydrocarbon group having 3 to 30 carbon atoms; and at least one group selected from the group consisting of —O—, —CO—, —COO—, —SO2O—, —NR—, —NRSO2—, —NRSO2O— and —NRCO—, wherein a part or all of hydrogen atoms included in the linear hydrocarbon group and the alicyclic hydrocarbon group are unsubstituted or substituted with a fluorine atom-free group, wherein R represents a hydrogen atom or a monovalent hydrocarbon group having 1 to 10 carbon atoms, and wherein in the formula (2), a value obtained by the formula of: {[(a formula mass of R4)+(a formula mass of R5)+(an atomic mass of nitrogen)]×n+(a formula mass of R6)} is no less than 120.
- Examples of the monovalent hydrocarbon group having 1 to 10 carbon atoms which may be represented by R4 include groups similar to those exemplified as the monovalent hydrocarbon group in connection with R1, R2 and R3, as described above.
- Examples of the divalent hydrocarbon group having 1 to 10 carbon atoms represented by R5 include groups derived by eliminating one hydrogen atom from a group exemplified as the monovalent hydrocarbon group in connection with R1, R2 and R3, as described above, and the like.
- Examples of the ring structure which may be represented by R4 and R5 by binding with each other, together with the nitrogen atom to which R4 and R5 bond include:
- monocyclic azacycloalkane structures such as an azacyclopropane structure, an azacyclobutane structure, an azacyclopentane structure (pyrrolidine structure), an azacyclohexane structure (piperidine structure), an azacycloheptane structure, an azacyclooctane structure and an azacyclodecane structure;
- polycyclic azacycloalkane structures such as an azabicyclo[2.2.1]heptane structure, an azabicyclo[2.2.2]octane structure, an azatricyclo[3.3.1.13,7]decane structure; and the like.
- Among these, monocyclic azacycloalkane structures are preferred, an azacyclopentane structure and an azacyclohexane structure are more preferred, and an azacyclohexane structure is still more preferred.
- Examples of the linear hydrocarbon group having 1 to 30 carbon atoms that constitutes R6 include groups similar to those exemplified as the linear hydrocarbon group in connection with the groups that constitute A, and the like.
- Examples of the alicyclic hydrocarbon group having 3 to 30 carbon atoms that constitutes R6 include groups similar to those exemplified as the alicyclic hydrocarbon group in connection with the groups that constitute A, and the like.
- Examples of the group, which is represented by R6, having a valency of n that is obtained by combining: at least one selected from the group consisting of a hydrogen atom, a linear hydrocarbon group and an alicyclic hydrocarbon group; and at least one group selected from the group consisting of —O—, —CO—, —COO—, —SO2O—, —NR—, —NRSO2—, —NRSO2O— and —NRCO— include cyclic ether groups, cyclic ketone groups, lactone groups, sultone groups, cyclic amino groups, cyclic sulfonamide groups, cyclic oxysulfonamide groups, lactam groups, alkoxy groups, acyl groups, acyloxy groups, alkylsulfonyloxy groups, alkoxysulfonyl groups, alkylamino groups, dialkylamino groups, alkoxyalkyl groups, acylalkyl groups, acyloxyalkyl groups, alkoxyalkyl groups, alkylsulfonyloxyalkyl groups, alkyliminosulfonyl groups, alkylsulfonylamidoalkyl groups, alkyliminosulfonyloxyalkyl groups, alkoxysulfonylamidoalkyl groups, alkyliminocarbonylalkyl groups, alkylcarbonyliminoalkyl groups, a hydroxy group, a formyl group, a carboxy group, a sulfo group, an amino group, and the like.
- Examples of the fluorine atom-free substituent that may be included in R6 include a cyano group, a nitro group, and the like.
- The lower limit of the value obtained by the formula of: [(a formula mass of R4+a formula mass of R5+an atomic mass of nitrogen)×n+(a formula mass of R6)] (hereinafter, may be also referred to as “the total atomic mass (1)”) in the above formula (2) is 120, preferably 150, more preferably 200, still more preferably 250, and particularly preferably 290. When the total atomic mass (1) is less than the lower limit, the volatility of the compound generated from the compound (2) after the exposure may be elevated, resulting in the tendency that the rectangularity of a cross-sectional shape of the photoresist composition is deteriorated.
- The upper limit of the total atomic mass (1) is preferably 1,000, more preferably 800, still more preferably 600, and particularly preferably 500. When the total atomic mass (1) is greater than the upper limit, the dispersibility of the compound (2) in the resist film may be reduced, resulting in the tendency that the photoresist composition leads to deterioration of the rectangularity of a cross-sectional shape, the LWR performance, the resolving ability and the depth of focus. It is to be noted that the formula mass of the group as referred to means a sum of atomic masses of the atoms constituting the group.
- The compound (2) is exemplified by the compounds (i1) to (i15), (i19), and (i20), and the like.
- The compound (2) is preferably the compound (i). The compound (i) is represented by the above formula (3).
- In the above formula (3), R1 to R5 are as defined in the above formula (2); R7, R8 and R9 each independently represent at least one group selected from the group consisting of a hydrogen atom, a linear hydrocarbon group having 1 to 30 carbon atoms and an alicyclic hydrocarbon group having 3 to 30 carbon atoms, or a group that is obtained by combining: the at least one group selected from the group consisting of a hydrogen atom, a linear hydrocarbon group having 1 to 30 carbon atoms and an alicyclic hydrocarbon group having 3 to 30 carbon atoms; and the at least one group selected from the group consisting of —O—, —CO—, —COO—, —SO2O—, —NR—, —NRSO2—, —NRSO2O— and —NRCO—, wherein at least two of R7, R8 and R9 optionally taken together represent a ring structure by binding with each other, together with the carbon atom to which the at least two of R7, R8 and R9 bond; and X represents —O—, —CO—, —COO—, —SO2O—, —NR—, —NRSO2—, —NRSO2O— or —NRCO—, and wherein a sum of formula masses of R4, R5, X, R7, R8 and R9 and atomic masses of the nitrogen and the carbon in the formula (3) is no less than 120.
- Examples of the linear hydrocarbon group having 1 to 30 carbon atoms and the alicyclic hydrocarbon group having 3 to 30 carbon atoms which may be represented by R7, R8 or R9 include groups similar to those exemplified as the linear hydrocarbon group and the alicyclic hydrocarbon group in connection with A in the above formula (1), and the like.
- Examples of the group that is obtained by combining: the at least one group selected from the group consisting of a hydrogen atom, a linear hydrocarbon group having 1 to 30 carbon atoms and an alicyclic hydrocarbon group having 3 to 30 carbon atoms; and the at least one group selected from the group consisting of —O—, —CO—, —COO—, —SO2O—, —NR—, —NRSO2—, —NRSO2O— and —NRCO— include cyclic ether groups, cyclic ketone groups, lactone groups, sultone groups, cyclic amino groups, cyclic sulfonamide groups, cyclic oxysulfonamide groups, lactam groups, alkoxy groups, acyl groups, acyloxy groups, alkylsulfonyloxy groups, alkoxysulfonyl groups, alkylamino groups, dialkylamino groups, alkoxyalkyl groups, acylalkyl groups, acyloxyalkyl groups, alkoxyalkyl groups, alkylsulfonyloxyalkyl groups, alkyliminosulfonyl groups, alkylsulfonylamidoalkyl groups, alkyliminosulfonyloxyalkyl groups, alkoxysulfonylamidoalkyl groups, alkyliminocarbonylalkyl groups, alkylcarbonyliminoalkyl groups, a hydroxy group, a formyl group, a carboxy group, a sulfo group, an amino group, and the like.
- R7, R8 and R9 represent preferably a hydrogen atom, a linear hydrocarbon group or an alkoxycarbonylalkyl group, more preferably a hydrogen atom, a methyl group or an ethoxycarbonyl group, and still more preferably a hydrogen atom or an ethoxycarbonyl group.
- Examples of the ring structure taken together represented by at least two of R7, R8 and R9 by binding with each other, together with the carbon atom to which the at least two of R7, R8 and R9 bond include:
- monocyclic alicyclic structures such as a cyclopentane structure and a cyclohexane structure;
- polycyclic alicyclic structures such as a norbornane structure, an adamantane structure and a camphor structure; and the like.
- Among these, polycyclic alicyclic structures are preferred, and an adamantane structure and a camphor structure are more preferred.
- X represents preferably —O—, —COO— or —SO2O—, more preferably —COO—, —SO2O—, and still more preferably —COO—*, —SO2O—* (* denotes a binding site to R5 in the above formula (3)).
- The lower limit of the sum of the formula masses of R4, R5, X, R7, R8 and R9 and the atomic masses of the nitrogen and the carbon in the formula (3) (hereinafter, may be also referred to as “the total atomic mass (2)”) is 120, preferably 150, more preferably 200, still more preferably 250, and particularly preferably 290. When the total atomic mass (2) is less than the lower limit, the volatility of the compound generated from the compound (i) after the exposure may be elevated, resulting in the tendency that the rectangularity of a cross-sectional shape of the photoresist composition is deteriorated.
- The upper limit of the total atomic mass (2) is preferably 1,000, more preferably 800, still more preferably 600, and particularly preferably 500. When the total atomic mass (2) is greater than the upper limit, the dispersibility of the compound (i) in the resist film may be reduced, resulting in the tendency that the photoresist composition leads to deterioration of the rectangularity of a cross-sectional shape, the LWR performance, the resolving ability and the depth of focus.
- Examples of the compound (i) include the compounds (i-1) to (i-15), and the like.
- The compound (i) can be synthesized in accordance with the following reaction scheme, for example.
- In the reaction scheme, R1, R2 and R3 each independently represent a hydrogen atom or a monovalent hydrocarbon group having 1 to 10 carbon atoms, wherein in a case where the monovalent hydrocarbon group is present in a plurality of number, at least two of these hydrocarbon groups optionally taken together represent a ring structure by binding with each other, together with the carbon atom to which the at least two of these hydrocarbon groups bond; R4 represents a hydrogen atom or a monovalent hydrocarbon group having 1 to 10 carbon atoms; R5 represents a divalent hydrocarbon group having 1 to 10 carbon atoms, wherein R4 and R5 optionally taken together represent an alicyclic structure by binding with each other, together with the nitrogen atom to which R4 and R5 bond; R7, R8 and R9 each independently represent at least one group selected from the group consisting of a hydrogen atom, a linear hydrocarbon group having 1 to 30 carbon atoms and an alicyclic hydrocarbon group having 3 to 30 carbon atoms, or a group that is obtained by combining: the at least one group selected from the group consisting of a hydrogen atom, a linear hydrocarbon group having 1 to 30 carbon atoms and an alicyclic hydrocarbon group having 3 to 30 carbon atoms; and the at least one group selected from the group consisting of —O—, —CO—, —COO—, —SO2O—, —NR—, —NRSO2—, —NRSO2O— and —NRCO—, wherein at least two of R7, R8 and R9 optionally taken together represent a ring structure by binding with each other, together with the carbon atom to which the at least two of R7, R8 and R9 bond; and X represents —O—, —CO—, —COO—, —SO2O—, —NR—, —NRSO2—, —NRSO2O— or —NRCO—; and Y and Z represent a group that forms X through a condensation reaction.
- The combination of Y with Z and the resulting X are exemplified by the following, and the like:
- when one of Y and Z represents a hydroxy group or a halogen atom and the rest of Y and Z represents a hydroxy group, —O— as X is obtained;
- when one of Y and Z represents a hydroxy group and the rest of Y and Z represents a halocarbonyl group, a carboxy group or an acid anhydride group, —COO— as X is obtained;
- when one of Y and Z represents a hydroxy group and the rest of Y and Z represents a halosulfonyl group or a sulfo group, —SO2O— as X is obtained;
- when one of Y and Z represents —NHR and the rest of Y and Z represents a halogen atom, —NR— as X is obtained;
- when one of Y and Z represents —NHR and the rest of Y and Z represents a halosulfonyl group or a sulfo group, —NRSO2— as X is obtained;
- when one of Y and Z represents —NHR and the rest of Y and Z represents a halosulfonyloxy group or a sulfoxy group, —NRSO2O— as X is obtained; and
- when one of Y and Z represents —NHR and the rest of Y and Z represents a halocarbonyl group, a carboxy group or an acid anhydride group, —NRCO— as X is obtained.
- The compound (i) that includes X can be obtained, for example, by reacting the compound that includes Y with the compound that includes Z, in a solvent such as dichloromethane in the presence of a base such as triethylamine or dimethylaminopyridine (DMAP).
- The content of the acid diffusion control agent (C) with respect of the acid generating agent (B) is preferably 1 mol % to 100 mol %, more preferably 3 mol % to 70 mol %, and still more preferably 5 mol % to 50 mol %, in light of the possibility that the photoresist composition leads to an improvement of the LWR performance, an EL (Exposure Latitude) performance and the rectangularity of a cross-sectional shape. When the content of the acid diffusion control agent (C) falls within the above range, the photoresist composition may lead to an improvement of the rectangularity of a cross-sectional shape, the LWR performance, the resolving ability and the sensitivity.
- Moreover, the amount of the acid diffusion control agent (C) with respect to 100 parts by mass of the polymer (A) is preferably no less than 0.1 parts by mass and no greater than 30 parts by mass, more preferably no less than 0.5 parts by mass and no greater than 20 parts by mass, and still more preferably no less than 1 part by mass and no greater than 15 parts by mass.
- The photoresist composition according to the embodiment of the present invention may contain (D) other acid diffusion controller, as needed. When the photoresist composition further contains the other acid diffusion controller (D) in addition to the acid diffusion control agent (C), the rectangularity of a cross-sectional shape, the LWR performance, the resolving ability and the depth of focus may be further improved. Although it is not necessarily clear why the aforementioned effect may be further improved when the other acid diffusion controller (D) is further contained, it may be presumed, for example, that a degree of diffusion of the compound as a whole contained in the acid diffusion control agent can be adjusted; and the like. The mode of incorporation of the other acid diffusion controller (D) in the photoresist composition may be in an acid diffusion control agent form which is a low molecular weight compound (hereinafter, may be also referred to as “(D) other acid diffusion control agent” or “other acid diffusion control agent (D)”, as appropriate), as described later, or in a form of an acid diffusion control group incorporated into the polymer as a part thereof, or in both of these forms.
- The other acid diffusion control agent (D) is exemplified by a compound represented by the following formula (5) (hereinafter, may be also referred to as “nitrogen-containing compound (I)”), a compound including two nitrogen atoms in a single molecule (hereinafter, may be also referred to as “nitrogen-containing compound (II)”), a compound including three nitrogen atoms (hereinafter, may be also referred to as “nitrogen-containing compound (III)”), an amide group-containing compound, a urea compound, a nitrogen-containing heterocyclic compound, and the like.
- In the above formula (5), R10, R11 and R12 each independently represent a hydrogen atom, a linear, branched or cyclic alkyl group, an aryl group or an aralkyl group each unsubstituted or substituted.
- Examples of the nitrogen-containing compound (I) include monoalkylamines such as n-hexylamine; dialkylamines such as di-n-butylamine; trialkylamines such as triethylamine; aromatic amines such as aniline; and the like.
- Examples of the nitrogen-containing compound (II) include ethylenediamine, N,N,N′,N′-tetramethylethylenediamine, and the like.
- Examples of the nitrogen-containing compound (III) include polyamine compounds such as polyethyleneimine and polyallylamine; polymers of dimethylaminoethylacrylamide, etc.; and the like.
- Examples of the amide group-containing compound include formamide, N-methylformamide, N,N-dimethylformamide, acetamide, N-methylacetamide, N,N-dimethylacetamide, propionamide, benzamide, pyrrolidone, N-methylpyrrolidone, and the like.
- Examples of the urea compound include urea, methylurea, 1,1-dimethylurea, 1,3-dimethylurea, 1,1,3,3-tetramethylurea, 1,3-diphenylurea, tributylthiourea, and the like.
- Examples of the nitrogen-containing heterocyclic compound include pyridines such as pyridine and 2-methylpyridine, pyrazine, pyrazole, and the like.
- A compound that includes an acid-labile group may also be used as the nitrogen-containing organic compound. Examples of such a nitrogen-containing organic compound that includes an acid-labile group include N-(t-butoxycarbonyl)piperidine, N-(t-butoxycarbonyl)imidazole, N-(t-butoxycarbonyl)benzimidazole, N-(t-butoxycarbonyl)-2-phenylbenzimidazole, N-(t-butoxycarbonyl)di-n-octylamine, N-(t-butoxycarbonyl)-diethanolamine, N-(t-butoxycarbonyl)-dicyclohexylamine, N-(t-butoxycarbonyl)-diphenylamine, N-(t-butoxycarbonyl)-4-hydroxypiperidine, and the like.
- Moreover, a photodegradable base that is sensitized upon an exposure to generate a weak acid may be used as the other acid diffusion controller (D). Examples of the photodegradable base include onium salt compounds that are degraded upon an exposure and lose its acid diffusion controlling ability, and the like. Examples of the onium salt compound include a sulfonium salt compound represented by the following formula (6-1), an iodonium salt compound represented by the following formula (6-2), and the like.
- In the above formulae (6-1) and (6-2), le to R17 each independently represent a hydrogen atom, an alkyl group, an alkoxy group, a hydroxy group or a halogen atom; E− and Q− each independently represent OH−, RβCOO−, Rβ—SO3 − or an anion represented by the following formula (6-3), wherein Rβ represents an alkyl group, an aryl group or an aralkyl group.
- In the above formula (6-3), R18 represents a linear or branched alkyl group having 1 to 12 carbon atoms, or a linear or branched alkoxyl group having 1 to 12 carbon atoms, wherein a part or all of hydrogen atoms included in the linear or branched alkyl group and the linear or branched alkoxyl group are unsubstituted or substituted with a fluorine atom; and u is an integer of 0 to 2.
- In a case where the other acid diffusion controller (D) is the other acid diffusion control agent (D), the content of the other acid diffusion controller (D) with respect of the acid generating agent (B) is preferably 1 mol % to 100 mol %, more preferably 3 mol % to 70 mol %, and still more preferably 5 mol % to 50 mol %. When the content of the other acid diffusion control agent (D) is greater than the upper limit, the photoresist composition may lead to deterioration of the sensitivity, the rectangularity of a cross-sectional shape, the LWR performance, the resolving ability and the depth of focus.
- Moreover, the amount of the other acid diffusion control agent (D) with respect to 100 parts by mass of the polymer (A) is preferably 0 to 20 parts by mass, more preferably 0.1 parts by mass to 15 parts by mass, and still more preferably 0.3 parts by mass to 10 parts by mass.
- The photoresist composition according to the embodiment of the present invention may contain (E) a fluorine-containing polymer (except for those corresponding to the polymer (A)). When the photoresist composition contains the fluorine-containing polymer (E), in forming a resist film, the fluorine-containing polymer (E) tends to be unevenly distributed in the vicinity of the surface of the resist film due to oil repellent characteristics of the fluorine-containing polymer in the film, and thus elution of the acid generating agent, the acid diffusion control agent and the like into a liquid immersion medium can be inhibited during an exposure through the liquid immersion medium. In addition, due to water repellent characteristics of the fluorine-containing polymer (E), an advancing contact angle of the liquid immersion medium on the resist film can be controlled to fall within a desired range, whereby formation of bubble defects can be inhibited. Furthermore, a larger receding contact angle of the liquid immersion medium on the resist film is attained, thereby enabling an exposure by high-speed scanning without being accompanied by residual water beads. Thus, when the photoresist composition contains the fluorine-containing polymer (E), a resist film suitable for a liquid immersion lithography process can be formed.
- The fluorine-containing polymer (E) is not particularly limited as long as the fluorine-containing polymer (E) contains a fluorine atom; however, it is preferred that the fluorine-containing polymer (E) has a higher content (% by mass) of fluorine atoms than that of the polymer (A) in the photoresist composition. When the fluorine-containing polymer (E) has a higher content (% by mass) of fluorine atoms than that of the polymer (A), a higher degree of the aforementioned uneven distribution is attained, leading to an improvement of characteristics such as water repellency and elution inhibitory ability of the resulting resist film.
- The content of fluorine atoms of the fluorine-containing polymer (E) falls within a range of preferably no less than 1% by mass, more preferably 2% by mass to 60% by mass, still more preferably 4% by mass to 40% by mass, and particularly preferably 7% by mass to 30% by mass. When the content of fluorine atoms of the fluorine-containing polymer (E) is less than the lower limit, the hydrophobicity of the surface of the resist film may be deteriorated. It is to be noted that the content (% by mass) of fluorine atoms of the polymer can be calculated based on the structure of the polymer as determined by 13C-NMR spectroscopy.
- The fluorine-containing polymer (E) preferably has at least one selected from the group consisting of the following structural unit (Ea) and the following structural unit (Eb). The fluorine-containing polymer (E) may have one, or two or more types of the structural unit (Ea) and/or the structural unit (Eb).
- The structural unit (Ea) is represented by the following formula (7a). When the fluorine-containing polymer (E) has the structural unit (Ea), the content of fluorine atoms thereof can be adjusted.
- In the above formula (7a), RD represents a hydrogen atom, a methyl group or a trifluoromethyl group; G represents a single bond, an oxygen atom, a sulfur atom, —CO—O—, —SO2—O—NH—, —CO—NH— or —O—CO—NH—; RE represents a monovalent linear hydrocarbon group having 1 to 6 carbon atoms and having at least one fluorine atom, or a monovalent aliphatic cyclic hydrocarbon group having 4 to 20 carbon atoms and having at least one fluorine atom.
- Examples of the linear hydrocarbon group having 1 to 6 carbon atoms and having at least one fluorine atom which may be represented by RE include a trifluoromethyl group, a 2,2,2-trifluoroethyl group, a perfluoroethyl group, a 2,2,3,3,3-pentafluoropropyl group, a 1,1,1,3,3,3-hexafluoropropyl group, a perfluoro-n-propyl group, a perfluoro-i-propyl group, a perfluoro-n-butyl group, a perfluoro-i-butyl group, a perfluoro-t-butyl group, a 2,2,3,3,4,4,5,5-octafluoropentyl group, a perfluorohexyl group, and the like.
- Examples of the aliphatic cyclic hydrocarbon group having 4 to 20 carbon atoms and having at least one fluorine atom which may be represented by RE include a monofluorocyclopentyl group, a difluorocyclopentyl group, a perfluorocyclopentyl group, a monofluorocyclohexyl group, a difluorocyclopentyl group, a perfluorocyclohexylmethyl group, a fluoronorbornyl group, a fluoroadamantyl group, a fluorobornyl group, a fluoroisobornyl group, a fluorotricyclodecyl group, a fluorotetracyclodecyl group, and the like.
- Examples of the monomer that gives the structural unit (Ea) include (meth)acrylic acid trifluoromethyl ester, (meth)acrylic acid 2,2,2-trifluoroethyl ester, (meth)acrylic acid perfluoroethyl ester, (meth)acrylic acid perfluoro-n-propyl ester, (meth)acrylic acid perfluoro-i-propyl ester, (meth)acrylic acid perfluoro-n-butyl ester, (meth)acrylic acid perfluoro-i-butyl ester, (meth)acrylic acid perfluoro-t-butyl ester, (meth)acrylic acid 2-(1,1,1,3,3,3-hexafluoropropyl) ester, (meth)acrylic acid 1-(2,2,3,3,4,4,5,5-octafluoropentyl) ester, (meth)acrylic acid perfluorocyclohexylmethyl ester, (meth)acrylic acid 1-(2,2,3,3,3-pentafluoropropyl) ester, (meth)acrylic acid monofluorocyclopentyl ester, (meth)acrylic acid difluorocyclopentyl ester, (meth)acrylic acid perfluorocyclopentyl ester, (meth)acrylic acid monofluorocyclohexyl ester, (meth)acrylic acid difluorocyclopentyl ester, (meth)acrylic acid perfluorocyclohexylmethyl ester, (meth)acrylic acid fluoronorbornyl ester, (meth)acrylic acid fluoroadamantyl ester, (meth)acrylic acid fluorobornyl ester, (meth)acrylic acid fluoroisobornyl ester, (meth)acrylic acid fluorotricyclodecyl ester, (meth)acrylic acid fluorotetracyclodecyl ester, and the like.
- The proportion of structural unit (Ea) with respect to the total structural units constituting the fluorine-containing polymer (E) is preferably 5 mol % to 80 mol %, more preferably 10 mol % to 60 mol %, and still more preferably 15 mol % to 40 mol %. When the proportion of the structural unit (Ea) falls within the above range, a larger dynamic contact angle on the surface of the resist film may be attained in an exposure through a liquid immersion medium.
- The structural unit (Eb) is represented by the following formula (7b). When the fluorine-containing polymer (E) has the structural unit (Eb), the hydrophobicity thereof may be enhanced, leading to a further improvement of the dynamic contact angle on the surface of the resist film formed from the photoresist composition.
- In the above formula (7b), RF represents a hydrogen atom, a methyl group or a trifluoromethyl group; R19 represents a hydrocarbon group having 1 to 20 carbon atoms and a valency of (s+1), which may further include an oxygen atom, a sulfur atom, —NR′—, a carbonyl group, —CO—O— or —CO—NH— at an end of R19 on the R2° side, wherein R′ represents a hydrogen atom or a monovalent organic group; R20 represents a single bond, a divalent linear hydrocarbon group having 1 to 10 carbon atoms or a divalent aliphatic cyclic hydrocarbon group having 4 to 20 carbon atoms; X2 represents a divalent linear hydrocarbon group having 1 to 20 carbon atoms and having at least one fluorine atom; A1 represents an oxygen atom, —NR″—, —CO—O—* or —SO2—O—*, wherein R″ represents a hydrogen atom or a monovalent organic group, and * denotes a binding site to R19; R21 represents a hydrogen atom or a monovalent organic group; and s is an integer of 1 to 3, wherein in a case where s is 2 or 3, a plurality of R20s are identical to or different with each other, a plurality of X2s are identical to or different with each other, a plurality of A1s are identical to or different with each other, and a plurality of R21s are identical to or different with each other.
- R21 preferably represents a hydrogen atom in light of the possibility of an increase of the solubility of the fluorine-containing polymer (E) in an alkaline developer solution.
- Examples of the monovalent organic group which may be represented by R21 include hydrocarbon groups having 1 to 30 carbon atoms and optionally including an acid-labile group, an alkali-labile group or a substituent, and the like.
- Examples of the structural unit (Eb) include structural units represented by the following formulae (7b-1) to (7b-3), and the like.
- In the above formulae (7b-1) to (7b-3), R19′ represents a divalent linear, branched or cyclic saturated or unsaturated hydrocarbon group having 1 to 20 carbon atoms; and RF, X2, R21 and s are as defined in the above formula (7b), wherein in a case where s is 2 or 3, a plurality of X2s are identical to or different with each other, and a plurality of R21s are identical to or different with each other.
- The proportion of the structural unit (7b) with respect to the total structural units constituting the fluorine-containing polymer (E) is preferably 0 mol % to 90 mol %, more preferably 5 mol % to 85 mol %, and still more preferably 10 mol % to 80 mol %. When the proportion of the structural unit (7b) falls within the above range, the degree of a decrease of the dynamic contact angle on the surface of the resist film formed from the photoresist composition in a development with an alkali may be reduced.
- The fluorine-containing polymer (E) may have, in addition to the structural units (Ea) and (Eb), a structural unit that includes an acid-labile group (hereinafter, may be also referred to as “structural unit (Ec)”) (except for those corresponding to the structural unit (Eb)). When the fluorine-containing polymer (E) has the structural unit (Ec), the configuration of the resulting resist pattern may be more favorable. Examples of the structural unit (Ec) include the structural unit (I) mentioned hereinabove in connection with the polymer (A), and the like.
- The proportion of the structural unit (Ec) with respect to the total structural units constituting the fluorine-containing polymer (E) is preferably 10 mol % to 90 mol %, more preferably 20 mol % to 85 mol %, still more preferably 30 mol % to 80 mol %, and particularly preferably 50 mol % to 75 mol %. When the proportion of the structural unit (Ec) is less than the lower limit, formation of development defects in the resist pattern may not be sufficiently inhibited. When the proportion of the structural unit (Ec) is greater than the upper limit, the hydrophobicity of the surface of the resulting resist film may be deteriorated.
- Also, the fluorine-containing polymer (E) may have, in addition to the structural units described above, other structural unit, such as, for example: a structural unit that includes an alkali-soluble group, a structural unit that includes at least one structure selected from the group consisting of a lactone structure, a cyclic carbonate structure and a sultone structure, a structural unit that includes an alicyclic group, etc. Examples of the alkali-soluble group include a carboxy group, a sulfonamide group, a sulfo group, and the like. Examples of the structural unit that includes at least one structure selected from the group consisting of a lactone structure, a cyclic carbonate structure and a sultone structure include the structural unit (II) mentioned hereinabove in connection with the polymer (A), and the like.
- The proportion of the other structural unit with respect to the total structural units constituting the fluorine-containing polymer (E) is typically no greater than 30 mol %, and preferably no greater than 20 mol %. When the proportion of the other structural unit is greater than the upper limit, the pattern formability of the photoresist composition may be deteriorated.
- The amount of the fluorine-containing polymer (E) in the photoresist composition with respect to 100 parts by mass of the polymer (A) is preferably 0 to 20 parts by mass, more preferably 0.5 parts by mass to 15 parts by mass, and still more preferably 1 part by mass to 10 parts by mass. When the amount of the fluorine-containing polymer (E) is greater than the upper limit, the pattern formability of the photoresist composition may be deteriorated.
- The photoresist composition according to the embodiment of the present invention typically contains (F) a solvent. The solvent (F) is not particularly limited as long as it is capable of dissolving or dispersing at least the polymer (A), the acid generator (B) and the acid diffusion control agent (C), as well as the other acid diffusion controller (D) contained as desired, and the like.
- The solvent (F) is exemplified by an alcohol solvent, an ether solvent, a ketone solvent, an amide solvent, an ester solvent, a hydrocarbon solvent, and the like.
- Examples of the alcohol solvent include:
- monohydric alcohol solvents such as methanol, ethanol, n-propanol, iso-propanol, n-butanol, iso-butanol, sec-butanol, tert-butanol, n-pentanol, iso-pentanol, 2-methylbutanol, sec-pentanol, tert-pentanol, 3-methoxybutanol, n-hexanol, 2-methylpentanol, sec-hexanol, 2-ethylbutanol, sec-heptanol, 3-heptanol, n-octanol, 2-ethylhexanol, sec-octanol, n-nonyl alcohol, 2,6-dimethyl-4-heptanol, n-decanol, sec-undecyl alcohol, trimethylnonyl alcohol, sec-tetradecyl alcohol, sec-heptadecyl alcohol, furfuryl alcohol, phenol, cyclohexanol, methylcyclohexanol, 3,3,5-trimethylcyclohexanol, benzyl alcohol and diacetone alcohol;
- polyhydric alcohol solvents such as ethylene glycol, 1,2-propylene glycol, 1,3-butylene glycol, 2,4-pentanediol, 2-methyl-2,4-pentanediol, 2,5-hexanediol, 2,4-heptanediol, 2-ethyl-1,3-hexanediol, diethylene glycol, dipropylene glycol, triethylene glycol and tripropylene glycol;
- polyhydric alcohol partial ether solvents such as ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, ethylene glycol monopropyl ether, ethylene glycol monobutyl ether, ethylene glycol monohexyl ether, ethylene glycol monophenyl ether, ethylene glycol mono-2-ethylbutyl ether, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, diethylene glycol monopropyl ether, diethylene glycol monobutyl ether, diethylene glycol monohexyl ether, propylene glycol monomethyl ether, propylene glycol monoethyl ether, propylene glycol monopropyl ether, propylene glycol monobutyl ether, dipropylene glycol monomethyl ether, dipropylene glycol monoethyl ether and dipropylene glycol monopropyl ether; and the like.
- Examples of the ether solvent include:
- dialkyl ether solvents such as diethyl ether, dipropyl ether and dibutyl ether;
- cyclic ether solvents such as tetrahydrofuran and tetrahydropyran;
- aromatic ring-containing ether solvents such as diphenyl ether and anisole (methyl phenyl ether); and the like.
- Examples of the ketone solvent include:
- linear ketone solvents such as acetone, methyl ethyl ketone, methyl n-propyl ketone, methyl n-butyl ketone, diethyl ketone, methyl iso-butyl ketone, 2-heptanone (methyl n-pentyl ketone), ethyl n-butyl ketone, methyl n-hexyl ketone, di-iso-butyl ketone and trimethylnonanone;
- cyclic ketone solvents such as cyclopentanone, cyclohexanone, cycloheptanone, cyclooctanone and methylcyclohexanone;
- 2,4-pentanedione, acetonylacetone and acetophenone; and the like.
- Examples of the amide solvent include:
- cyclic amide solvents such as N,N′-dimethylimidazolidinone and N-methylpyrrolidone;
- linear amide solvents such as N-methylformamide, N,N-dimethylformamide, N,N-diethylformamide, acetamide, N-methylacetamide, N,N-dimethylacetamide and N-methylpropionamide; and the like.
- Examples of the ester solvent include:
- acetic acid ester solvents such as methyl acetate, ethyl acetate, n-propyl acetate, iso-propyl acetate, n-butyl acetate, iso-butyl acetate, sec-butyl acetate, n-pentyl acetate, i-pentyl acetate, sec-pentyl acetate, 3-methoxybutyl acetate, methylpentyl acetate, 2-ethylbutyl acetate, 2-ethylhexyl acetate, benzyl acetate, cyclohexyl acetate, methylcyclohexyl acetate and n-nonyl acetate;
- polyhydric alcohol partial ether acetate solvents such as ethylene glycol monomethyl ether acetate, ethylene glycol monoethyl ether acetate, diethylene glycol monomethyl ether acetate, diethylene glycol monoethyl ether acetate, diethylene glycol mono-n-butyl ether acetate, propylene glycol monomethyl ether acetate, propylene glycol monoethyl ether acetate, propylene glycol monopropyl ether acetate, propylene glycol monobutyl ether acetate, dipropylene glycol monomethyl ether acetate and dipropylene glycol monoethyl ether acetate;
- carbonate solvents such as diethyl carbonate;
- glycol diacetate, methoxytriglycol acetate, ethyl propionate, n-butyl propionate, iso-amyl propionate, diethyl oxalate, di-n-butyl oxalate, methyl acetoacetate, ethyl acetoacetate, methyl lactate, ethyl lactate, n-butyl lactate, n-amyl lactate, diethyl malonate, dimethyl phthalate and diethyl phthalate; and the like.
- Examples of the hydrocarbon solvent include:
- aliphatic hydrocarbon solvents such as n-pentane, iso-pentane, n-hexane, iso-hexane, n-heptane, iso-heptane, 2,2,4-trimethylpentane, n-octane, iso-octane, cyclohexane and methylcyclohexane;
- aromatic hydrocarbon solvents such as benzene, toluene, xylene, mesitylene, ethylbenzene, trimethylbenzene, methylethylbenzene, n-propylbenzene, iso-propylbenzene, diethylbenzene, iso-butylbenzene, triethylbenzene, di-iso-propylbenzene and n-amylnaphthalene; and the like.
- Among these, an ester solvent and a ketone solvent are preferred, a polyhydric alcohol partial ether acetate solvent and a cyclic ketone solvent are more preferred, and propylene glycol monomethyl ether acetate and cyclohexanone are still more preferred. The photoresist composition may contain one, or two or more types of the solvent (F).
- The photoresist composition may contain other optional component(s) in addition to the aforementioned components (A) to (F). The other optional component(s) may be exemplified by an uneven distribution accelerator, a surfactant, an alicyclic skeleton-containing compound, a sensitizing agent, and the like. These other optional components each may be used alone, or in combination of two or more types thereof.
- Uneven Distribution Accelerator
- The uneven distribution accelerator exhibits the effect of more efficiently segregating the fluorine-containing polymer (E) on the surface of the resist film. When the photoresist composition contains the uneven distribution accelerator, the amount of the fluorine-containing polymer (E) added may be reduced as compared with conventional levels. Therefore, the elution of the components from the resist film into a liquid immersion liquid may be further suppressed and/or an exposure through a liquid immersion medium may be carried out at a higher speed by high speed scanning, without deteriorating characteristics such as the rectangularity of a cross-sectional shape, the LWR performance, the resolving ability and the depth of focus; as a result, the hydrophobicity of the surface of the resist film, which inhibits defects attributed to the liquid immersion, e.g., watermark defects, may be enhanced. As an exemplary uneven distribution accelerator having such features, a low molecular weight compound having a relative permittivity of no less than 30 and no greater than 200, and a boiling point at 1 atm of no less than 100° C. may be used. The compound is specifically exemplified by a lactone compound, a carbonate compound, a nitrile compound, a polyhydric alcohol, and the like.
- Examples of the lactone compound include γ-butyrolactone, valerolactone, mevalonic lactone, norbornanelactone, and the like.
- Examples of the carbonate compound include propylene carbonate, ethylene carbonate, butylene carbonate, vinylene carbonate, and the like.
- Examples of the nitrile compound include succinonitrile, and the like.
- Examples of the polyhydric alcohol include glycerin, and the like.
- The amount of the uneven distribution accelerator in the photoresist composition with respect to 100 parts by mass of the total polymer(s) is preferably 10 parts by mass to 500 parts by mass, more preferably 15 parts by mass to 300 parts by mass, and still more preferably 20 parts by mass to 100 parts by mass.
- Surfactant
- The surfactant exhibits the effect of improving a coating property, striation, developability, and the like. Examples of the surfactant include nonionic surfactants such as polyoxyethylene lauryl ether, polyoxyethylene stearyl ether, polyoxyethylene oleyl ether, polyoxyethylene n-octylphenyl ether, polyoxyethylene n-nonylphenyl ether, polyethylene glycol dilaurate and polyethylene glycol distearate; and commercially available products such as KP341 (manufactured by Shin-Etsu Chemical Co., Ltd.), Polyflow No. 75 and No. 95 (each manufactured by Kyoeisha Chemical Co., Ltd.), EFTOP EF301, EF303 and EF352 (each manufactured by Tochem Products Co. Ltd.), Megaface F171 and F173 (each manufactured by DIC Corporation), Fluorad FC430 and FC431 (each manufactured by Sumitomo 3M Limited), ASAHI GUARD AG710, Surflon S-382, SC-101, SC-102, SC-103, SC-104, SC-105 and SC-106 (each manufactured by Asahi Glass Co., Ltd.); and the like. The amount of the surfactant in the photoresist composition with respect to 100 parts by mass of the polymer (A) is typically no greater than 2 parts by mass.
- Alicyclic Skeleton-Containing Compound
- The alicyclic skeleton-containing compound exhibits the effect of improving dry etching resistance, a pattern configuration, adhesiveness to substrate, and the like.
- Examples of the alicyclic skeleton-containing compound include:
- adamantane derivatives such as 1-adamantanecarboxylic acid, 2-adamantanone and t-butyl 1-adamantanecarboxylate;
- deoxycholic acid esters such as t-butyl deoxycholate, t-butoxycarbonylmethyl deoxycholate and 2-ethoxyethyl deoxycholate;
- lithocholic acid esters such as t-butyl lithocholate, t-butoxycarbonylmethyl lithocholate and 2-ethoxyethyl lithocholate;
- 3-[2-hydroxy-2,2-bis(trifluoromethyl)ethyl]tetracyclo[4.4.0.12,5.17,10]dodecane and 2-hydroxy-9-methoxycarbonyl-5-oxo-4-oxa-tricyclo[4.2.1.03,7]nonane; and the like. The amount of the alicyclic skeleton-containing compound in the photoresist composition with respect to 100 parts by mass of the polymer (A) is typically no greater than 5 parts by mass.
- Sensitizing Agent
- The sensitizing agent exhibits the action of increasing the amount of an acid generated from the acid generating agent (B) and the like, and exerts the effect of improving “apparent sensitivity” of the photoresist composition.
- Examples of the sensitizing agent include carbazoles, acetophenones, benzophenones, naphthalenes, phenols, biacetyl, eosin, rose bengal, pyrenes, anthracenes, phenothiazines, and the like. These sensitizing agents may be used either alone, or in combination of two or more types thereof. The amount of the sensitizing agent in the photoresist composition with respect to 100 parts by mass of the polymer (A) is typically no greater than 2 parts by mass.
- The photoresist composition according to the embodiment of the present invention may be prepared, for example, by mixing the polymer (A), the acid generator (B) and the acid diffusion control agent (C), as well as the optional component(s) and the solvent (F) each contained as needed in a predetermined ratio. After the mixing, the photoresist composition is preferably filtered through a filter with a pore size of about 0.2 μm, for example. The solid content concentration of the photoresist composition is typically 0.1% by mass to 50% by mass, preferably 0.5% by mass to 30% by mass, and more preferably 1% by mass to 20% by mass.
- A resist pattern forming method according to another embodiment of the present invention includes:
- providing a resist film using the photoresist composition according to the embodiment of the present invention (hereinafter, may be also referred to as “resist film-providing step”);
- exposing the resist film (hereinafter, may be also referred to as “exposure step”); and
- developing the resist film exposed (hereinafter, may be also referred to as “development step”).
- According to the resist pattern-forming method, since the aforementioned photoresist composition is used, a resist pattern can be formed that exhibits superior rectangularity of a cross-sectional shape, decreased LWR and a superior resolving ability, while attaining a greater depth of focus. Hereinafter, each step will be explained.
- In the resist film-providing step, the photoresist composition according to the embodiment of the present invention is coated on a substrate by appropriate coating means such as spin-coating, cast coating and roll coating to provide a resist film. Examples of the substrate include silicon wafers, wafers covered with silicon dioxide or an antireflective film, and the like. Specifically, after the photoresist composition is coated such that the resulting resist film has a predetermined film thickness, prebaking (PB) is carried out to permit the solvent present in the coating film to be volatilized, resulting in the formation of the resist film. The temperature of PB is typically 60° C. to 140° C., and preferably 80° C. to 120° C. The time period of PB is typically 5 sec to 600 sec, and preferably 10 sec to 300 sec.
- In the exposure step, the resist film provided in the resist film-providing step is exposed. The exposure is carried out, for example, by irradiating the resist film with an exposure light through a photomask (through a liquid immersion medium such as water, as needed). The exposure light is exemplified by: an electromagnetic wave such as a visible light ray, an ultraviolet ray, a far ultraviolet ray, an X-ray and a γ-ray; a charged particle ray such as an electron beam and an α-ray; and the like, in accordance with the line width of the intended pattern. Among these, a far ultraviolet ray and an electron beam are preferred, an ArF excimer laser beam (wavelength: 193 nm), a KrF excimer laser beam (wavelength: 248 nm) and an electron beam are more preferred, and an ArF excimer laser beam and an electron beam are still more preferred.
- It is preferred that post exposure baking (PEB) is carried out after the exposure, to facilitate the dissociation of the acid-labile group of the polymer (A) which is mediated by the acid generated from the acid generator (B) at exposed sites of the resist film upon the exposure. This PEB makes the difference of the solubility in a developer solution between at a site subjected to the exposure (light-exposed site) and a site not subjected to the exposure (light-unexposed site). The temperature of the PEB is typically 50° C. to 180° C., and preferably 80° C. to 130° C. The time period of the PEB is typically 5 sec to 600 sec, and preferably 10 sec to 300 sec.
- In the development step, the resist film exposed is developed with a developer solution to form a predetermined resist pattern. After the development, washing with a rinse agent such as water or an alcohol followed by drying is typically carried out.
- In the case of a development with an alkali, examples of the developer solution include aqueous alkali solutions prepared by dissolving at least one type of alkaline compounds such as sodium hydroxide, potassium hydroxide, sodium carbonate, sodium silicate, sodium metasilicate, aqueous ammonia, ethylamine, n-propylamine, diethylamine, di-n-propylamine, triethylamine, methyldiethylamine, ethyldimethylamine, triethanolamine, tetramethylammonium hydroxide (TMAH), pyrrole, piperidine, choline, 1,8-diazabicyclo-[5.4.0]-7-undecene and 1,5-diazabicyclo-[4.3.0]-5-nonene; and the like. Among these, an aqueous TMAH solution is preferred, and a 2.38% by mass aqueous TMAH solution is more preferred.
- Alternatively, in the case of a development with an organic solvent, the developer solution is exemplified by: an organic solvent such as a hydrocarbon solvent, an ether solvent, an ester solvent, a ketone solvent and an alcohol solvent; and a solvent containing an organic solvent. Examples of the organic solvent include one, or two or more types of the solvents enumerated in connection with the solvent (F) which may be contained in the abovementioned photoresist composition, and the like. Among these, an ester solvent and a ketone solvent are preferred. As the ester solvent, acetic acid ester solvents are preferred, and n-butyl acetate is more preferred. As the ketone solvent, linear ketones are preferred, and 2-heptanone is more preferred.
- In addition, in a case where an exposure through a liquid immersion medium is carried out, a liquid immersion liquid-insoluble protective film for liquid immersion may be provided on the resist film for the purpose of avoiding a direct contact of the resist film with a liquid immersion liquid before the exposure step. As the protective film for liquid immersion, any one of a solvent-peelable protective film that is peeled by a solvent before the development step (see, for example, Japanese Unexamined Patent Application, Publication No. 2006-227632) and a developer solution-peelable protective film that is peeled concomitantly with the development in the development step (see, for example, WO 2005-069076 and WO 2006-035790) may be used. However, a developer solution-peelable protective film for liquid immersion is preferably used in light of throughput.
- An acid diffusion control agent according to still another embodiment of the present invention contains the compound (1). The compound (1) is represented by the above formula (1).
- In the above formula (1), R1, R2 and R3 each independently represent a hydrogen atom or a monovalent hydrocarbon group having 1 to 10 carbon atoms, wherein in a case where the monovalent hydrocarbon group is present in a plurality of number, at least two of these hydrocarbon groups optionally taken together represent a ring structure by binding with each other, together with the carbon atom to which the at least two of these hydrocarbon groups bond; A represents a group having a valency of n that is obtained by combining: at least one group selected from the group consisting of a hydrogen atom, a linear hydrocarbon group having 1 to 30 carbon atoms and an alicyclic hydrocarbon group having 3 to 30 carbon atoms; at least one group selected from the group consisting of —O—, —CO—, —COO—, —SO2O—, —NR—, —NRSO2—, —NRSO2O— and —NRCO—; and n nitrogen atoms as a binding site to the carbonyl group in the above formula (1), wherein a sum of atomic masses of the atoms constituting A is no less than 120, wherein a part or all of hydrogen atoms included in the linear hydrocarbon group and the alicyclic hydrocarbon group are unsubstituted or substituted with a fluorine atom-free group, and wherein R represents a hydrogen atom or a monovalent hydrocarbon group having 1 to 10 carbon atoms; and n is an integer of 1 to 4.
- The compound (1) is preferably the compound (2).
- In the above formula (2), R1, R2, R3 and n are as defined in the above formula (1); R4 represents a hydrogen atom or a monovalent hydrocarbon group having 1 to 10 carbon atoms; R5 represents a divalent hydrocarbon group having 1 to 10 carbon atoms, wherein R4 and R5 optionally taken together represent an alicyclic structure by binding with each other, together with the nitrogen atom to which R4 and R5 bond; R6 represents a group having a valency of n that is obtained by combining: at least one group selected from the group consisting of a hydrogen atom, a linear hydrocarbon group having 1 to 30 carbon atoms and an alicyclic hydrocarbon group having 3 to 30 carbon atoms; and at least one group selected from the group consisting of —O—, —CO—, —COO—, —SO2O—, —NR—, —NRSO2—, —NRSO2O— and —NRCO—, wherein a part or all of hydrogen atoms included in the linear hydrocarbon group and the alicyclic hydrocarbon group are unsubstituted or substituted with a fluorine atom-free group, wherein R represents a hydrogen atom or a monovalent hydrocarbon group having 1 to 10 carbon atoms, and wherein in the formula (2), a value obtained by the formula of: {[(a formula mass of R4)+(a formula mass of R5)+(an atomic mass of nitrogen)]×n+(a formula mass of R6)} is no less than 120.
- The compound (2) is preferably the compound (3).
- In the above formula (3), R1 to R5 are as defined in the above formula (2); R7, R8 and R9 each independently represent at least one group selected from the group consisting of a hydrogen atom, a linear hydrocarbon group having 1 to 30 carbon atoms and an alicyclic hydrocarbon group having 3 to 30 carbon atoms, or a group that is obtained by combining: the at least one group selected from the group consisting of a hydrogen atom, a linear hydrocarbon group having 1 to 30 carbon atoms and an alicyclic hydrocarbon group having 3 to 30 carbon atoms; and at least one group selected from the group consisting of —O—, —CO—, —COO—, —SO2O—, —NR—, —NRSO2—, —NRSO2O— and —NRCO—, wherein at least two of R7, R8 and R9 optionally taken together represent a ring structure by binding with each other, together with the carbon atom to which the at least two of R7, R8 and R9 bond; and X represents —O—, —CO—, —COO—, —SO2O—, —NR—, —NRSO2—, —NRSO2O— or —NRCO—, and wherein a sum of formula masses of R4, R5, X, R7, R8 and R9 and atomic masses of the nitrogen and the carbon in the formula (3) is no less than 120.
- The acid diffusion control agent according to the embodiment of the present invention has been explained in connection with the acid diffusion control agent (C) contained in the photoresist composition.
- A compound according to yet still another embodiment of the present invention is represented by the above formula (3).
- In the above formula (3), R1, R2 and R3 each independently represent a hydrogen atom or a monovalent hydrocarbon group having 1 to 10 carbon atoms, wherein in a case where the monovalent hydrocarbon group is present in a plurality of number, at least two of these hydrocarbon groups optionally taken together represent a ring structure by binding with each other, together with the carbon atom to which the at least two of these hydrocarbon groups bond; R4 represents a hydrogen atom or a monovalent hydrocarbon group having 1 to 10 carbon atoms; R5 represents a divalent hydrocarbon group having 1 to 10 carbon atoms, wherein R4 and R5 optionally taken together represent an alicyclic structure by binding with each other, together with the nitrogen atom to which R4 and R5 bond; R7, R8 and R9 each independently represent at least one group selected from the group consisting of a hydrogen atom, a linear hydrocarbon group having 1 to 30 carbon atoms and an alicyclic hydrocarbon group having 3 to 30 carbon atoms, or a group that is obtained by combining: the at least one group selected from the group consisting of a hydrogen atom, a linear hydrocarbon group having 1 to 30 carbon atoms and an alicyclic hydrocarbon group having 3 to 30 carbon atoms; and at least one group selected from the group consisting of —O—, —CO—, —COO—, —SO2O—, —NR—, —NRSO2—, —NRSO2O— and —NRCO—, wherein at least two of R7, R8 and R9 optionally taken together represent a ring structure by binding with each other, together with the carbon atom to which the at least two of R7, R8 and R9 bond; and X represents —O—, —CO—, —COO—, —SO2O—, —NR—, —NRSO2—, —NRSO2O— or —NRCO—, and wherein a sum of formula masses of R4, R5, X, R7, R8 and R9 and atomic masses of the nitrogen and the carbon in the formula (3) is no less than 120.
- The compound according to the embodiment of the present invention is the aforementioned compound (i), and has been explained in the section of the acid diffusion control agent (C) in connection with the photoresist composition.
- Hereinafter, the present invention is explained in detail by way of Examples, but the present invention is not in any way limited by Examples. Measuring methods for various types of physical properties are shown below.
- 1H-NMR analysis and 13C-NMR analysis of the compound, as well as 13C-NMR analysis for the determination of the proportion of each constituent unit and the content of fluorine atoms of the polymer were carried out using a nuclear magnetic resonance spectrometer (JNM-ECX400, manufactured by JEOL, Ltd.).
- Compounds (i-1) to (i-4), which fell under the compound (i), were synthesized in accordance with the following reaction scheme.
- In the above scheme: L represents C and Rα represents an adamantyl group, an ethoxycarbonylmethyl group or a camphor group; or L represents S═O and Rα represents a methyl group.
- Into a 200 mL eggplant-shaped flask were charged 3.00 g (13.9 mmol) of N-t-amyloxycarbonyl-4-hydroxypiperidine, 2.11 g (20.9 mmol) of triethylamine, 0.034 g of dimethylaminopyridine (0.279 mmol) and 40 g of dichloromethane, and the mixture was cooled to 0° C. on an ice bath. Next, to this mixture, 3.32 g (16.7 mmol) of 1-adamantylcarboxylic acid chloride dissolved in 20 g of dichloromethane was added dropwise over 10 min. Thereafter, the mixture was stirred at 0° C. for 30 min, and then stirred at room temperature for 20 hrs. After the reaction was quenched by the addition of water, the reaction mixture was extracted with dichloromethane, followed by washing with water and purification by way of column chromatography to obtain 4.62 g of a compound represented by the following formula (i-1) (hereinafter, may be also referred to as “compound (i-1)”) (yield: 87.8%).
- Compounds represented by the following formulae (i-2) to (i-4) were each synthesized in a similar manner to Example 1 except that the corresponding other derivative was used in place of 1-adamantylcarboxylic acid chloride.
- Monomers used in the synthesis of the polymer (A) and the fluorine-containing polymer (E) are shown below.
- A monomer solution was prepared by dissolving 9.01 g (50 mol %) of the compound (M-1) and 10.99 g (50 mol %) of the compound (M-2) in 40 g of 2-butanone, and further dissolving therein 0.81 g (5 mol % with respect to the total mol number of the compounds) of AIBN as a polymerization initiator. A 100 mL three-neck flask containing 20 g of 2-butanone was purged with a nitrogen gas for 30 min, and then heated to 80° C. with stirring, and the monomer solution prepared above was added dropwise over 3 hrs using a dropping funnel. The time of the start of the dropwise addition was regarded as the time of the start of the polymerization reaction, and the polymerization reaction was allowed to proceed for 6 hrs. After the completion of the polymerization reaction, the polymerization reaction solution was water-cooled to 30° C. or below. The cooled polymerization reaction solution was poured into 400 g of methanol, and the deposited white powder was filtered off. The filtered white powder was washed twice with 80 g of methanol, followed by filtration, and dried at 50° C. for 17 hrs to obtain a polymer (A-1) as a white powder (recovered amount: 15.6 g; yield: 78%). The polymer (A-1) had an Mw of 7,200 and an Mw/Mn of 1.52. The result of 13C-NMR analysis indicated that the proportions of the structural unit derived from the compound (M-1) and the structural unit derived from (M-2) were 50.2 mol % and 49.8 mol %, respectively. The content of low molecular weight components in the polymer (A-1) was 0.04% by mass.
- After 55.0 g (65 mol %) of the compound (M-4), 45.0 g (35 mol %) of the compound (M-5), 4 g of AIBN and 1 g of t-dodecyl mercaptan were dissolved in 100 g of propylene glycol monomethyl ether, the polymerization was allowed to proceed for 16 hrs under a nitrogen atmosphere, while maintaining the reaction temperature of 70° C. After the completion of the polymerization reaction, the polymerization reaction solution was added dropwise to 1,000 g of n-hexane to solidify and purify the polymer. Next, 150 g of propylene glycol monomethyl ether was added to the polymer, then 150 g of methanol, 34 g of triethylamine and 6 g of water were further added, and a hydrolysis reaction was allowed to proceed for 8 hrs while the mixture was refluxed at the boiling point thereof. After the completion of the reaction, the solvent and triethylamine were distilled under vacuum. The resulting polymer was dissolved in 150 g of acetone, and the solution was added dropwise to 2,000 g of water to permit solidification. The formed white powder was filtered off, and dried at 50° C. for 17 hrs to obtain a polymer (A-2) as a white powder (65.7 g; yield: 76.6%). The polymer (A-2) had an Mw of 10,000 and an Mw/Mn of 2.1. The result of 13C-NMR analysis indicated that the proportions of the structural unit derived from p-hydroxystyrene and the structural unit derived from the compound (M-5) were 65.4 mol % and 34.6 mol %, respectively. The content of low molecular weight components in the polymer (A-2) was 0.05% by mass.
- A monomer solution was prepared by dissolving 79.9 g (70 mol %) of the compound (M-1) and 20.91 g (30 mol %) of the compound (M-3) in 100 g of 2-butanone, and further dissolving 4.77 g of dimethyl 2,2′-azobisisobutyrate as a polymerization initiator. A 1,000 mL three-neck flask containing 100 g of 2-butanone was purged with nitrogen gas for 30 min, and then heated to 80° C. with stirring, and the monomer solution prepared above was added dropwise over 3 hrs using a dropping funnel. The time of the start of the dropwise addition was regarded as the time of the start of the polymerization reaction, and the polymerization reaction was allowed to proceed for 6 hrs. After the completion of the polymerization reaction, the polymerization reaction solution was water-cooled to 30° C. or below. The polymerization reaction solution was transferred to a 2 L separatory funnel, and then the polymerization reaction solution was homogeneously diluted with 150 g of n-hexane. Into the diluted polymerization reaction solution was charged 600 g of methanol and mixed therewith, then 30 g of distilled water was charged, followed by further stirring, and then the mixture was left to stand for 30 min. Thereafter, the underlayer was recovered, and the solvent was substituted to prepare a propylene glycol monomethyl ether acetate solution of a polymer (E-1) (yield: 60%). The polymer (E-1) had an Mw of 7,200 and an Mw/Mn of 2.00. The result of 13C-NMR analysis indicated that the proportions of the structural unit derived from the compound (M-1) and the structural unit derived from the compound (M-3) were 71.1 mol % and 28.9 mol %, respectively. The content of low molecular weight components in the polymer (E-1) was 0.07% by mass.
- Components used in the preparation of the photoresist composition are shown below.
- triphenylsulfonium 2-(adamantan-1-yl)-1,1-difluoroethane-1-sulfonate (compound represented by the following formula (B-1))
- C-1: compound (i-1) synthesized above (compound represented by the above formula (i-1))
- C-2: compound (i-2) synthesized above (compound represented by the above formula (i-2))
- C-3: compound (i-3) synthesized above (compound represented by the above formula (i-3))
- C-4: compound (i-4) synthesized above (compound represented by the above formula (i-4))
- CC-1: N-t-amyloxycarbonyl-4-hydroxypiperidine (compound represented by the following formula (CC-1))
- F-1: propylene glycol monomethyl ether acetate
- F-2: cyclohexanone
- G-1: γ-butyrolactone
- A photoresist composition (J-1) was prepared by mixing 100 parts by mass of (A-1) as the polymer (A), 8.5 parts by mass of (B-1) as the acid generating agent (B), 30 mol % (mol % with respect to the acid generating agent (B)) of (C-1) as the acid diffusion control agent (C), 3 parts by mass of (E-1) as the fluorine atom-containing polymer (E), 2,240 parts by mass of (F-1) and 960 parts by mass (F-2) as the solvent (F), as well as 30 parts by mass of (G-1) as the uneven distribution accelerator (G).
- Photoresist compositions (J-2) to (J-4) and (CJ-1) were prepared in a similar manner to Example 5 except that the type and the content of each component were as specified in Table 1.
-
TABLE 1 Composition (E) Fluorine (B) Acid atom-containing (G) Uneven distri- (A) Polymer generating agent (C) Acid diffusion polymer (F) Solvent bution accelerator amount amount control agent amount amount amount Photoresist (parts (parts amount (parts (parts (parts Composition type by mass) type by mass) type (mol %) type by mass) type by mass) type by mass) Example 5 J-1 A-1 100 B-1 8.5 C-1 30 E-1 3 F-1/F-2 2,240/960 G-1 30 Example 6 J-2 A-1 100 B-1 8.5 C-2 30 E-1 3 F-1/F-2 2,240/960 G-1 30 Example 7 J-3 A-1 100 B-1 8.5 C-3 30 E-1 3 F-1/F-2 2,240/960 G-1 30 Example 8 J-4 A-1 100 B-1 8.5 C-4 30 E-1 3 F-1/F-2 2,240/960 G-1 30 Comparative CJ-1 A-1 100 B-1 8.5 CC-1 30 E-1 3 F-1/F-2 2,240/960 G-1 30 Example 1 - Development with Alkali
- An underlayer antireflective film having a film thickness of 105 nm was provided on the surface of a 12-inch silicon wafer by coating a composition for forming an underlayer antireflective film (ARC66, manufactured by Brewer Science) on the surface of the 12-inch silicon wafer using a spin coater (CLEAN TRACK ACT12, manufactured by Tokyo Electron Limited), and thereafter heating the same to 205° C. for 60 sec. Each photoresist composition was coated on the underlayer antireflective film using the spin coater, and subjected to PB at 90° C.60 sec. Thereafter, cooling was carried out at 23° C. for 30 sec to provide a resist film having a film thickness of 90 nm. Next, the resist film was exposed using an ArF excimer laser Immersion Scanner (NSR-S610C, manufactured by NIKON) through a 40 nm line-and-space (1L1S) mask pattern, under optical conditions involving NA of 1.3 and dipole (Sigma: 0.977/0.782). After the exposure, PEB was carried out at 90° C. for 60 sec. Thereafter, a development with a 2.38% by mass aqueous TMAH solution was carried out, followed by washing with water and drying to form a positive resist pattern.
- Development with Organic Solvent
- A negative resist pattern was formed in a similar manner to the abovementioned “Development with Alkali” except that n-butyl acetate was used in place of the 2.38% by mass aqueous TMAH solution as the developer solution and the step of washing with water was skipped.
- The photoresist compositions were evaluated through measurements for resist patterns formed therefrom. The results of the evaluations are shown in Table 2. The symbol “-” in Table 2 indicates a reference for evaluation. A scanning electron microscope (S-9380, manufactured by Hitachi High-Technologies Corporation) was used in the measurement of the resist patterns.
- LWR Performance
- The resist pattern formed was observed from above the pattern using the scanning electron microscope. The line width was measured at arbitrary points of 50 in total, and a 3 Sigma value was determined from the distribution of the measurements, and the value was designated as “LWR performance”. The smaller value indicates a more favorable LWR performance. The LWR performance was evaluated to be “A” (favorable) in the case of an improvement of the LWR performance by no less than 10% as compared with the photoresist composition according to Comparative Example 1 (which means a value indicative of the LWR performance being no greater than 90% of a value for the photoresist composition according to Comparative Example 1) being found, and to be “B” (unfavorable) in the case of an improvement of the LWR performance by less than 10% being found.
- Resolving Ability
- A dimension of the minimum resist pattern which was resolved at an optimum exposure dose was designated as “resolving ability”. The smaller value indicates a more favorable resolving ability. The resolving ability was evaluated to be “A” (favorable) in the case of an improvement of the resolving ability by no less than 10% as compared with the photoresist composition according to Comparative Example 1 (which means a value indicative of the resolving ability being no greater than 90% of a value for the photoresist composition according to Comparative Example 1) being found, and to be “B” (unfavorable) in the case of an improvement of the resolving ability by less than 10% being found.
- Rectangularity of Cross-Sectional Shape
- The cross-sectional shape of the resist pattern which was resolved at the optimum exposure dose was observed, and a line width Lb in the middle portion of the resist pattern and a line width La at the top of the resist pattern were measured. The rectangularity of the cross-sectional shape was evaluated to be “A” (favorable) in a case where the La/Lb value fell within a range of no less than 0.9 and no greater than 1.1, and to be “B” (unfavorable) in a case where the La/Lb value was less than 0.9 or greater than 1.1.
- Depth of Focus
- On the resist pattern which was resolved at the optimum exposure dose, the dimension when the focus was shifted along the depth direction was observed, and a latitude of the depth direction in which the pattern dimension fell within the range of 90% to 110% of the reference while not accompanied by a bridge and/or residue was measured, and the measurement result was defined as the “depth of focus”. The greater value indicates a more favorable depth of focus. The depth of focus was evaluated to be “A” (favorable) in the case of an improvement of the depth of focus by no less than 10% as compared with the photoresist composition according to Comparative Example 1 (which means a value indicative of the depth of focus being no less than 110% of a value for the photoresist composition according to Comparative Example 1) being found, and to be “B” (unfavorable) in the case of an improvement of the depth of focus by less than 10% being found.
-
TABLE 2 Evaluation results development with alkali development with organic solvent LWR rectangularity depth LWR rectangularity depth Photoresist perfor- resolving of cross-sec- of perfor- resolving of cross-sec- of composition mance ability tional shape focus mance ability tional shape focus Example 5 J-1 A A A A A A A A Example 6 J-2 A A A A A A A A Example 7 J-3 A A A A A A A A Example 8 J-4 A A A A A A A A Comparative CJ-1 — — B — — — B — Example 1 - A photoresist composition (J-5) was prepared by mixing 100 parts by mass of (A-2) as the polymer (A), 20 parts by mass of (B-1) as the acid generating agent (B), 30 mol % (molar ratio with respect to the acid generating agent (B)) of (C-1) as the acid diffusion control agent (C) as well as 4,280 parts by mass of (F-1) and 1,830 parts by mass of (F-2) as the solvent (F).
- Photoresist compositions (J-6) to (J-8) were prepared in a similar manner to Example 11 except that the type and the content of each component were as specified in Table 3.
- Each photoresist composition shown in Table 3 below was coated on the surface of an 8-inch silicon wafer using a spin coater (CLEAN TRACK ACT8, manufactured by Tokyo Electron Limited), and subjected to PB at 90° C. for 60 sec. Thereafter, cooling was carried out at 23° C. for 30 sec, whereby a resist film having a film thickness of 50 nm was provided. Next, this resist film was irradiated with an electron beam using a simplified electron beam writer (HL800D, manufactured by Hitachi, Ltd., power: 50 KeV, electric current density: 5.0 ampere/cm2). After the irradiation, PEB was carried out at 130° C. for 60 sec. Thereafter, a development was carried out at 23° C. for 30 sec using a 2.38% by mass aqueous TMAH solution as a developer solution, followed by washing with water and drying to form a positive resist pattern.
- Evaluations were made on the resist patterns formed in a similar manner to those described in the aforementioned “Formation of Resist Pattern through Exposure by Way of ArF Excimer Laser Beam” (the photoresist composition according to Comparative Example 2 being employed as a reference for each evaluation). The results of the evaluations are collectively shown in Table 3. The symbol “-” in Table 3 indicates a reference for evaluation.
-
TABLE 3 Composition (B) acid (A) polymer generating agent (C) acid diffusion Evaluation results amount amount control agent (F) solvent LWR rectangularity Photoresist (parts (parts amount amount (parts perfor- resolving of cross-sec- composition type by mass) type by mass) type (mol %) type by mass) mance ability tional shape Example 9 J-5 A-2 100 B-1 20 C-1 30 F-1/F-2 4,280/1,830 A A A Example 10 J-6 A-2 100 B-1 20 C-2 30 F-1/F-2 4,280/1,830 A A A Example 11 J-7 A-2 100 B-1 20 C-3 30 F-1/F-2 4,280/1,830 A A A Example 12 J-8 A-2 100 B-1 20 C-4 30 F-1/F-2 4,280/1,830 A A A Comparative CJ-2 A-2 100 B-1 20 CC-1 30 F-1/F-2 4,280/1,830 — — B Example 2 - From the results shown in Tables 2 and 3, it is found that in both cases of the exposure by way of an ArF excimer laser beam and the exposure by way of an electron beam, and also in both cases the development with an alkali and the development with an organic solvent, the photoresist compositions according to Examples enable a resist pattern to be obtained which exhibits superior pattern configuration, decreased LWR and a superior resolving ability, while attaining a greater depth of focus.
- The photoresist composition according to the embodiments of the present invention and the resist pattern-forming method using the photoresist composition enable a resist pattern to be formed that exhibits superior rectangularity of a cross-sectional shape, decreased LWR and a superior resolving ability, while attaining a greater depth of focus. The acid diffusion control agent according to the present invention can be suitably used as an acid diffusion control agent component of the photoresist composition. Moreover, the compound according to the present invention can be suitably used as the acid diffusion control agent. Therefore, these can be suitably used in pattern formation involved in the production of semiconductor devices, in which further progress of miniaturization is expected in the future.
Claims (9)
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2012058033 | 2012-03-14 | ||
JP2012-058033 | 2012-03-14 | ||
PCT/JP2013/056543 WO2013137157A1 (en) | 2012-03-14 | 2013-03-08 | Photoresist composition, method for forming resist pattern, acid diffusion control agent and compound |
Related Parent Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/JP2013/056543 Continuation WO2013137157A1 (en) | 2012-03-14 | 2013-03-08 | Photoresist composition, method for forming resist pattern, acid diffusion control agent and compound |
Publications (3)
Publication Number | Publication Date |
---|---|
US20150004544A1 US20150004544A1 (en) | 2015-01-01 |
US20150309406A9 true US20150309406A9 (en) | 2015-10-29 |
US9557641B2 US9557641B2 (en) | 2017-01-31 |
Family
ID=49161066
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US14/486,532 Active 2033-07-23 US9557641B2 (en) | 2012-03-14 | 2014-09-15 | Photoresist composition, resist pattern-forming method, acid diffusion control agent, and compound |
Country Status (5)
Country | Link |
---|---|
US (1) | US9557641B2 (en) |
JP (1) | JP6075369B2 (en) |
KR (1) | KR102075960B1 (en) |
TW (1) | TWI575313B (en) |
WO (1) | WO2013137157A1 (en) |
Families Citing this family (41)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP6222057B2 (en) * | 2014-11-25 | 2017-11-01 | 信越化学工業株式会社 | Chemically amplified resist material and pattern forming method |
US10324377B2 (en) * | 2015-06-15 | 2019-06-18 | Tokyo Ohka Kogyo Co., Ltd. | Resist composition and method of forming resist pattern |
JP6665528B2 (en) * | 2015-12-25 | 2020-03-13 | Jsr株式会社 | Radiation-sensitive resin composition, cured film, method for forming the same, and display element |
JP7042551B2 (en) * | 2016-09-20 | 2022-03-28 | 東京応化工業株式会社 | Resist composition and resist pattern forming method |
JP6780092B2 (en) | 2017-03-31 | 2020-11-04 | 富士フイルム株式会社 | Actinic light-sensitive or radiation-sensitive resin composition, resist film, pattern forming method, manufacturing method of electronic device |
KR102402138B1 (en) * | 2017-11-28 | 2022-05-25 | 아사히 가세이 가부시키가이샤 | Negative photosensitive resin composition, manufacturing method thereof, and manufacturing method of cured relief pattern |
WO2019167570A1 (en) * | 2018-03-01 | 2019-09-06 | 富士フイルム株式会社 | Actinic-light-sensitive or radiation-sensitive resin composition, resist film, pattern formation method, and method for manufacturing electronic device |
WO2019188595A1 (en) | 2018-03-26 | 2019-10-03 | 富士フイルム株式会社 | Photosensitive resin composition, production method therefor, resist film, pattern formation method, and method for producing electronic device |
JPWO2020105505A1 (en) | 2018-11-22 | 2021-10-21 | 富士フイルム株式会社 | Actinic light-sensitive or radiation-sensitive resin composition, resist film, pattern forming method, manufacturing method of electronic device |
EP3919980A4 (en) | 2019-01-28 | 2022-03-30 | FUJIFILM Corporation | Active-light-sensitive or radiation-sensitive resin composition, resist film, pattern formation method, and method for manufacturing electronic device |
CN113168098B (en) | 2019-01-28 | 2024-03-29 | 富士胶片株式会社 | Actinic-ray-or radiation-sensitive resin composition, resist film, pattern forming method, and method for manufacturing electronic device |
EP3919528A4 (en) | 2019-01-28 | 2022-03-30 | FUJIFILM Corporation | Actinic ray-sensitive or radiation-sensitive resin composition, resist film, pattern formation method, and electronic device manufacturing method |
TWI836094B (en) | 2019-06-21 | 2024-03-21 | 日商富士軟片股份有限公司 | Photosensitive radiation or radiation-sensitive resin composition, photoresist film, pattern forming method, manufacturing method of electronic device |
WO2020261784A1 (en) | 2019-06-25 | 2020-12-30 | 富士フイルム株式会社 | Production method for radiation-sensitive resin composition |
EP3992179A4 (en) | 2019-06-28 | 2022-11-02 | FUJIFILM Corporation | Method for producing active light sensitive or radiation sensitive resin composition, pattern forming method, and method for producing electronic device |
CN114270264A (en) | 2019-08-26 | 2022-04-01 | 富士胶片株式会社 | Actinic-ray-sensitive or radiation-sensitive resin composition, pattern forming method, resist film, and method for producing electronic device |
EP4024132A4 (en) | 2019-08-28 | 2022-11-02 | FUJIFILM Corporation | Active-light-sensitive or radiation-sensitive resin composition, resist film, pattern formation method, method for manufacturing electronic device, compound, and resin |
KR20220034157A (en) | 2019-08-29 | 2022-03-17 | 후지필름 가부시키가이샤 | Actinic ray-sensitive or radiation-sensitive resin composition, actinic ray-sensitive or radiation-sensitive film, pattern formation method, and method for manufacturing an electronic device |
TW202128970A (en) | 2019-08-29 | 2021-08-01 | 日商富士軟片股份有限公司 | Active light ray-sensitive or radiation-sensitive resin composition, active light ray-sensitive or radiation-sensitive film, method for forming pattern, and method for producing electronic device |
JP7310471B2 (en) * | 2019-09-12 | 2023-07-19 | Jsr株式会社 | Pattern forming method and composition |
WO2021060348A1 (en) | 2019-09-26 | 2021-04-01 | 富士フイルム株式会社 | Heat-conducting layer production method, laminate production method, and semiconductor device production method |
JP7219822B2 (en) | 2019-09-30 | 2023-02-08 | 富士フイルム株式会社 | Actinic ray- or radiation-sensitive resin composition, actinic ray- or radiation-sensitive film, pattern forming method, and electronic device manufacturing method |
CN115362412A (en) | 2020-03-30 | 2022-11-18 | 富士胶片株式会社 | Actinic-ray-or radiation-sensitive resin composition, actinic-ray-or radiation-sensitive film, pattern formation method, method for producing electronic device, actinic-ray-or radiation-sensitive resin composition for photomask production, and method for producing photomask |
WO2021200179A1 (en) | 2020-03-31 | 2021-10-07 | 富士フイルム株式会社 | Actinic-ray-sensitive or radiation-sensitive resin composition, actinic-ray-sensitive or radiation-sensitive film, method for forming pattern, and method for producing electronic device |
WO2021251086A1 (en) | 2020-06-10 | 2021-12-16 | 富士フイルム株式会社 | Active-ray-sensitive or radiation-sensitive resin composition, resist film, pattern formation method, method for manufacturing electronic device, and compound |
KR20230006907A (en) | 2020-06-10 | 2023-01-11 | 후지필름 가부시키가이샤 | Actinic ray-sensitive or radiation-sensitive resin composition, resist film, pattern formation method, electronic device manufacturing method |
WO2022158323A1 (en) | 2021-01-22 | 2022-07-28 | 富士フイルム株式会社 | Pattern formation method and method for producing electronic device |
EP4293055A4 (en) | 2021-02-09 | 2024-08-14 | Fujifilm Corp | Active-ray-sensitive or radiation-sensitive resin composition, resist film, method for forming positive-working pattern, and method for manufacturing electronic device |
KR20230131900A (en) | 2021-02-12 | 2023-09-14 | 후지필름 가부시키가이샤 | Actinic ray-sensitive or radiation-sensitive resin composition, resist film, pattern formation method, electronic device manufacturing method |
JPWO2022172602A1 (en) | 2021-02-15 | 2022-08-18 | ||
WO2022209733A1 (en) | 2021-03-29 | 2022-10-06 | 富士フイルム株式会社 | Active light-sensitive or radiation-sensitive resin composition, resist film, method for forming pattern, and method for producing electronic device |
KR20230158040A (en) | 2021-04-16 | 2023-11-17 | 후지필름 가부시키가이샤 | Actinic ray-sensitive or radiation-sensitive resin composition, resist film, pattern formation method, electronic device manufacturing method, and compound |
EP4372018A1 (en) | 2021-07-14 | 2024-05-22 | FUJIFILM Corporation | Active light-sensitive or radiation-sensitive resin composition, resist film, pattern forming method, and method for producing electronic device |
KR20240019832A (en) | 2021-07-14 | 2024-02-14 | 후지필름 가부시키가이샤 | Pattern formation method, manufacturing method of electronic device |
EP4372466A1 (en) | 2021-07-14 | 2024-05-22 | FUJIFILM Corporation | Pattern forming method, electronic device manufacturing method, actinic ray-sensitive or radiation-sensitive resin composition, and resist film |
KR20240036064A (en) | 2021-08-25 | 2024-03-19 | 후지필름 가부시키가이샤 | Chemical solution, pattern formation method |
IL311594A (en) | 2021-09-29 | 2024-05-01 | Fujifilm Corp | Actinic ray-sensitive or radiation-sensitive resin composition and method for producing resist pattern |
JPWO2023106171A1 (en) | 2021-12-10 | 2023-06-15 | ||
KR20240103044A (en) | 2021-12-23 | 2024-07-03 | 후지필름 가부시키가이샤 | Actinic ray-sensitive or radiation-sensitive resin composition, actinic ray-sensitive or radiation-sensitive film, pattern formation method, electronic device manufacturing method, and compound |
WO2023157635A1 (en) | 2022-02-16 | 2023-08-24 | 富士フイルム株式会社 | Actinic-ray-sensitive or radiation-sensitive resin composition, actinic-ray-sensitive or radiation-sensitive film, pattern forming method, method for producing electronic device, and compound |
KR20240135851A (en) | 2022-02-25 | 2024-09-12 | 후지필름 가부시키가이샤 | Active light-sensitive or radiation-sensitive resin composition, resist film, pattern forming method, and method for manufacturing electronic device |
Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2011048175A (en) * | 2009-08-27 | 2011-03-10 | Jsr Corp | Radiation sensitive resin composition |
US20120052441A1 (en) * | 2010-08-26 | 2012-03-01 | Masayoshi Sagehashi | Nitrogen-containing organic compound, chemically amplified positive resist composition, and patterning process |
US20120214099A1 (en) * | 2008-01-08 | 2012-08-23 | International Business Machines Corporation | Photoresist compositions |
US20120282548A1 (en) * | 2010-01-08 | 2012-11-08 | Fujifilm Corporation | Pattern forming method, actinic ray-sensitive or radiation-sensitive resin composition and resist film |
Family Cites Families (14)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
KR950005301B1 (en) * | 1990-09-04 | 1995-05-23 | 주식회사대웅제약 | Novel quinolone carbocylic acid deriverjives |
JP4425405B2 (en) | 2000-02-04 | 2010-03-03 | Jsr株式会社 | Positive radiation sensitive resin composition |
JP2006227632A (en) | 2003-02-20 | 2006-08-31 | Tokyo Ohka Kogyo Co Ltd | Immersion lithography process-use resist protection film forming material, composite film and resist pattern forming method |
WO2005069076A1 (en) | 2004-01-15 | 2005-07-28 | Jsr Corporation | Upper layer film forming composition for liquid immersion and method of forming photoresist pattern |
KR101108754B1 (en) | 2004-09-30 | 2012-03-14 | 제이에스알 가부시끼가이샤 | Copolymer and top coating composition |
JP2006321770A (en) | 2005-05-20 | 2006-11-30 | Eiweiss Kk | 1,1-dimethylpropyloxycarbonyl group-containing compound and utilization thereof |
US7838198B2 (en) * | 2007-12-13 | 2010-11-23 | International Business Machines Corporation | Photoresist compositions and method for multiple exposures with multiple layer resist systems |
JP5175579B2 (en) * | 2008-02-25 | 2013-04-03 | 富士フイルム株式会社 | Positive resist composition and pattern forming method using the same |
CN102483574B (en) | 2009-07-17 | 2014-07-09 | Jsr株式会社 | Radiation-sensitive resin composition and compound |
JP5450114B2 (en) * | 2010-01-08 | 2014-03-26 | 富士フイルム株式会社 | Pattern forming method, chemically amplified resist composition, and resist film |
JP5422402B2 (en) | 2010-01-08 | 2014-02-19 | 富士フイルム株式会社 | Pattern forming method, chemically amplified resist composition, and resist film |
KR101831685B1 (en) * | 2010-01-25 | 2018-02-23 | 롬 앤드 하스 일렉트로닉 머트어리얼즈 엘엘씨 | Photoresist comprising nitrogen-containing compound |
JP5440515B2 (en) * | 2011-01-14 | 2014-03-12 | 信越化学工業株式会社 | Resist material and pattern forming method |
JP5618958B2 (en) * | 2011-09-22 | 2014-11-05 | 富士フイルム株式会社 | Pattern forming method, actinic ray-sensitive or radiation-sensitive resin composition, resist film, method for producing electronic device, and electronic device |
-
2013
- 2013-03-08 KR KR1020147025087A patent/KR102075960B1/en active IP Right Grant
- 2013-03-08 WO PCT/JP2013/056543 patent/WO2013137157A1/en active Application Filing
- 2013-03-08 JP JP2014504844A patent/JP6075369B2/en active Active
- 2013-03-11 TW TW102108443A patent/TWI575313B/en active
-
2014
- 2014-09-15 US US14/486,532 patent/US9557641B2/en active Active
Patent Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US20120214099A1 (en) * | 2008-01-08 | 2012-08-23 | International Business Machines Corporation | Photoresist compositions |
JP2011048175A (en) * | 2009-08-27 | 2011-03-10 | Jsr Corp | Radiation sensitive resin composition |
US20120282548A1 (en) * | 2010-01-08 | 2012-11-08 | Fujifilm Corporation | Pattern forming method, actinic ray-sensitive or radiation-sensitive resin composition and resist film |
US20120052441A1 (en) * | 2010-08-26 | 2012-03-01 | Masayoshi Sagehashi | Nitrogen-containing organic compound, chemically amplified positive resist composition, and patterning process |
Non-Patent Citations (1)
Title |
---|
Machine translation of JP 2011-048175 (no date). * |
Also Published As
Publication number | Publication date |
---|---|
TWI575313B (en) | 2017-03-21 |
WO2013137157A1 (en) | 2013-09-19 |
KR102075960B1 (en) | 2020-02-11 |
US9557641B2 (en) | 2017-01-31 |
JP6075369B2 (en) | 2017-02-08 |
KR20140135972A (en) | 2014-11-27 |
TW201344353A (en) | 2013-11-01 |
JPWO2013137157A1 (en) | 2015-08-03 |
US20150004544A1 (en) | 2015-01-01 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
US9557641B2 (en) | Photoresist composition, resist pattern-forming method, acid diffusion control agent, and compound | |
US10088750B2 (en) | Acid diffusion control agent, radiation-sensitive resin composition, resist pattern-forming method, compound, and production method | |
JP6115377B2 (en) | Resin composition and resist pattern forming method | |
US9594303B2 (en) | Resist pattern-forming method and photoresist composition | |
KR102239635B1 (en) | Resist composition, method of forming resist pattern and solvent for resist | |
TW201405249A (en) | Method for forming negative resist pattern and photoresist composition | |
JPWO2012053396A1 (en) | Resist pattern forming method and radiation-sensitive resin composition | |
US20130260315A1 (en) | Radiation-sensitive resin composition, pattern-forming method, polymer, and compound | |
US20150355550A1 (en) | Production method of semiconductor element, and ion implantation method | |
JP6241226B2 (en) | Photoresist composition, resist pattern forming method, polymer and compound | |
WO2017057203A1 (en) | Radiation sensitive resin composition and resist pattern forming method | |
JP6319291B2 (en) | Radiation sensitive resin composition, resist pattern forming method, radiation sensitive acid generator and compound | |
JP5867298B2 (en) | Photoresist composition and resist pattern forming method | |
JP6069691B2 (en) | Acid diffusion controller, radiation sensitive resin composition, and resist pattern forming method | |
KR102248827B1 (en) | Radiation-sensitive resin composition, method for forming resist pattern, acid generator, and compound | |
JP6036545B2 (en) | Photoresist composition, resist pattern forming method, polymer and compound | |
KR102294069B1 (en) | Radiation-sensitive resin composition, method for forming resist pattern, polymer, compound and method for manufacturing the same | |
JP6079128B2 (en) | Photoresist composition and resist pattern forming method |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
AS | Assignment |
Owner name: JSR CORPORATION, JAPAN Free format text: ASSIGNMENT OF ASSIGNORS INTEREST;ASSIGNOR:NAMAI, HAYATO;REEL/FRAME:033887/0607 Effective date: 20140904 |
|
STCF | Information on status: patent grant |
Free format text: PATENTED CASE |
|
MAFP | Maintenance fee payment |
Free format text: PAYMENT OF MAINTENANCE FEE, 4TH YEAR, LARGE ENTITY (ORIGINAL EVENT CODE: M1551); ENTITY STATUS OF PATENT OWNER: LARGE ENTITY Year of fee payment: 4 |
|
MAFP | Maintenance fee payment |
Free format text: PAYMENT OF MAINTENANCE FEE, 8TH YEAR, LARGE ENTITY (ORIGINAL EVENT CODE: M1552); ENTITY STATUS OF PATENT OWNER: LARGE ENTITY Year of fee payment: 8 |