JP4687898B2 - 含フッ素ケイ素化合物、シリコーン樹脂、それを用いたレジスト組成物、及びパターン形成方法 - Google Patents
含フッ素ケイ素化合物、シリコーン樹脂、それを用いたレジスト組成物、及びパターン形成方法 Download PDFInfo
- Publication number
- JP4687898B2 JP4687898B2 JP2006069010A JP2006069010A JP4687898B2 JP 4687898 B2 JP4687898 B2 JP 4687898B2 JP 2006069010 A JP2006069010 A JP 2006069010A JP 2006069010 A JP2006069010 A JP 2006069010A JP 4687898 B2 JP4687898 B2 JP 4687898B2
- Authority
- JP
- Japan
- Prior art keywords
- group
- carbon atoms
- atom
- branched
- bis
- 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.)
- Expired - Fee Related
Links
- 239000000203 mixture Substances 0.000 title claims description 68
- 229910052731 fluorine Inorganic materials 0.000 title claims description 54
- 239000011737 fluorine Substances 0.000 title claims description 46
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 title claims description 44
- 229920002050 silicone resin Polymers 0.000 title claims description 40
- 238000000034 method Methods 0.000 title claims description 34
- 150000003377 silicon compounds Chemical class 0.000 title claims description 33
- 125000004432 carbon atom Chemical group C* 0.000 claims description 133
- 125000004122 cyclic group Chemical group 0.000 claims description 60
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 58
- 239000002253 acid Substances 0.000 claims description 41
- 125000000962 organic group Chemical group 0.000 claims description 41
- 125000003545 alkoxy group Chemical group 0.000 claims description 36
- 125000003367 polycyclic group Chemical group 0.000 claims description 35
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 32
- 125000005843 halogen group Chemical group 0.000 claims description 29
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 27
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 27
- 239000000758 substrate Substances 0.000 claims description 25
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 16
- 229910052799 carbon Inorganic materials 0.000 claims description 15
- 125000001153 fluoro group Chemical group F* 0.000 claims description 12
- 239000003960 organic solvent Substances 0.000 claims description 12
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 9
- 238000010438 heat treatment Methods 0.000 claims description 7
- 238000010894 electron beam technology Methods 0.000 claims description 6
- -1 t-butoxycarbonyl group Chemical group 0.000 description 396
- 239000000178 monomer Substances 0.000 description 68
- 229910000077 silane Inorganic materials 0.000 description 46
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 45
- 125000000217 alkyl group Chemical group 0.000 description 37
- 125000003118 aryl group Chemical group 0.000 description 37
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 37
- 229920005989 resin Polymers 0.000 description 35
- 239000011347 resin Substances 0.000 description 35
- 150000001412 amines Chemical class 0.000 description 34
- 238000005530 etching Methods 0.000 description 33
- 230000015572 biosynthetic process Effects 0.000 description 26
- 229910052757 nitrogen Inorganic materials 0.000 description 26
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 24
- 238000003786 synthesis reaction Methods 0.000 description 22
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 21
- 239000007983 Tris buffer Substances 0.000 description 21
- 125000000524 functional group Chemical group 0.000 description 20
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 20
- 229910052710 silicon Inorganic materials 0.000 description 20
- 238000006243 chemical reaction Methods 0.000 description 19
- 125000001731 2-cyanoethyl group Chemical group [H]C([H])(*)C([H])([H])C#N 0.000 description 18
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 17
- 239000000243 solution Substances 0.000 description 17
- 229920000642 polymer Polymers 0.000 description 16
- 125000001424 substituent group Chemical group 0.000 description 16
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
- 150000001875 compounds Chemical class 0.000 description 15
- 125000006165 cyclic alkyl group Chemical group 0.000 description 15
- SNRUBQQJIBEYMU-UHFFFAOYSA-N dodecane Chemical compound CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 14
- 239000010703 silicon Substances 0.000 description 14
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 14
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 13
- 125000003710 aryl alkyl group Chemical group 0.000 description 13
- 150000002430 hydrocarbons Chemical group 0.000 description 13
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 12
- 125000001624 naphthyl group Chemical group 0.000 description 12
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 12
- 238000009835 boiling Methods 0.000 description 11
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 11
- 239000010410 layer Substances 0.000 description 11
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 11
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 11
- KZJRKRQSDZGHEC-UHFFFAOYSA-N 2,2,2-trifluoro-1-phenylethanone Chemical compound FC(F)(F)C(=O)C1=CC=CC=C1 KZJRKRQSDZGHEC-UHFFFAOYSA-N 0.000 description 10
- RGSFGYAAUTVSQA-UHFFFAOYSA-N Cyclopentane Chemical compound C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 10
- 125000002947 alkylene group Chemical group 0.000 description 10
- 239000002585 base Substances 0.000 description 10
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 10
- 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 10
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 10
- 238000004821 distillation Methods 0.000 description 10
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 10
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 9
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- 150000001721 carbon Chemical group 0.000 description 9
- 239000000047 product Substances 0.000 description 9
- YXHKONLOYHBTNS-UHFFFAOYSA-N Diazomethane Chemical class C=[N+]=[N-] YXHKONLOYHBTNS-UHFFFAOYSA-N 0.000 description 8
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 8
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 8
- 125000004093 cyano group Chemical group *C#N 0.000 description 8
- 239000007789 gas Substances 0.000 description 8
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 7
- 230000001588 bifunctional effect Effects 0.000 description 7
- 238000009833 condensation Methods 0.000 description 7
- 230000005494 condensation Effects 0.000 description 7
- 125000000753 cycloalkyl group Chemical group 0.000 description 7
- 125000001033 ether group Chemical group 0.000 description 7
- 150000002596 lactones Chemical group 0.000 description 7
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 7
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 7
- UMRZSTCPUPJPOJ-KNVOCYPGSA-N norbornane Chemical group C1C[C@H]2CC[C@@H]1C2 UMRZSTCPUPJPOJ-KNVOCYPGSA-N 0.000 description 7
- 125000004043 oxo group Chemical group O=* 0.000 description 7
- 125000005010 perfluoroalkyl group Chemical group 0.000 description 7
- 229910052717 sulfur Inorganic materials 0.000 description 7
- 125000004434 sulfur atom Chemical group 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- NCJZVRPXSSYDBG-UHFFFAOYSA-N 2,2,2-trifluoro-1-(4-methoxyphenyl)ethanone Chemical compound COC1=CC=C(C(=O)C(F)(F)F)C=C1 NCJZVRPXSSYDBG-UHFFFAOYSA-N 0.000 description 6
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- 125000004453 alkoxycarbonyl group Chemical group 0.000 description 6
- 150000001244 carboxylic acid anhydrides Chemical class 0.000 description 6
- 125000004210 cyclohexylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 6
- 125000004185 ester group Chemical group 0.000 description 6
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 6
- 238000001459 lithography Methods 0.000 description 6
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 6
- 239000012299 nitrogen atmosphere Substances 0.000 description 6
- 125000005188 oxoalkyl group Chemical group 0.000 description 6
- 229910052760 oxygen Inorganic materials 0.000 description 6
- 239000001301 oxygen Substances 0.000 description 6
- 230000005855 radiation Effects 0.000 description 6
- 239000002994 raw material Substances 0.000 description 6
- 230000008961 swelling Effects 0.000 description 6
- WGTYBPLFGIVFAS-UHFFFAOYSA-M tetramethylammonium hydroxide Chemical compound [OH-].C[N+](C)(C)C WGTYBPLFGIVFAS-UHFFFAOYSA-M 0.000 description 6
- ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 description 6
- LJHFIVQEAFAURQ-ZPUQHVIOSA-N (NE)-N-[(2E)-2-hydroxyiminoethylidene]hydroxylamine Chemical class O\N=C\C=N\O LJHFIVQEAFAURQ-ZPUQHVIOSA-N 0.000 description 5
- VINRTVDNUHIWCB-UHFFFAOYSA-N 2,2,2-trifluoro-1-(2,4,6-trimethylphenyl)ethanone Chemical compound CC1=CC(C)=C(C(=O)C(F)(F)F)C(C)=C1 VINRTVDNUHIWCB-UHFFFAOYSA-N 0.000 description 5
- DYILUJUELMWXAL-UHFFFAOYSA-N 2,2,2-trifluoro-1-(4-methylphenyl)ethanone Chemical compound CC1=CC=C(C(=O)C(F)(F)F)C=C1 DYILUJUELMWXAL-UHFFFAOYSA-N 0.000 description 5
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 5
- 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 5
- 125000004864 4-thiomethylphenyl group Chemical group 0.000 description 5
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 5
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 5
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 5
- 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 description 5
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 5
- GPRLTFBKWDERLU-UHFFFAOYSA-N bicyclo[2.2.2]octane Chemical compound C1CC2CCC1CC2 GPRLTFBKWDERLU-UHFFFAOYSA-N 0.000 description 5
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 5
- 229910052801 chlorine Inorganic materials 0.000 description 5
- 125000004851 cyclopentylmethyl group Chemical group C1(CCCC1)C* 0.000 description 5
- 238000011161 development Methods 0.000 description 5
- 230000018109 developmental process Effects 0.000 description 5
- 229910001882 dioxygen Inorganic materials 0.000 description 5
- KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical class [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 description 5
- DMEGYFMYUHOHGS-UHFFFAOYSA-N heptamethylene Natural products C1CCCCCC1 DMEGYFMYUHOHGS-UHFFFAOYSA-N 0.000 description 5
- 238000004519 manufacturing process Methods 0.000 description 5
- 239000000463 material Substances 0.000 description 5
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 5
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 5
- 125000004433 nitrogen atom Chemical group N* 0.000 description 5
- 229920001296 polysiloxane Polymers 0.000 description 5
- 230000035945 sensitivity Effects 0.000 description 5
- 229910052814 silicon oxide Inorganic materials 0.000 description 5
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 5
- 125000003944 tolyl group Chemical group 0.000 description 5
- 238000012546 transfer Methods 0.000 description 5
- KYXIHKXHBSORRJ-UHFFFAOYSA-N 1-(2,4-dimethylphenyl)-2,2,2-trifluoroethanone Chemical compound CC1=CC=C(C(=O)C(F)(F)F)C(C)=C1 KYXIHKXHBSORRJ-UHFFFAOYSA-N 0.000 description 4
- 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 4
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 4
- OJGMBLNIHDZDGS-UHFFFAOYSA-N N-Ethylaniline Chemical compound CCNC1=CC=CC=C1 OJGMBLNIHDZDGS-UHFFFAOYSA-N 0.000 description 4
- 238000005481 NMR spectroscopy Methods 0.000 description 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 238000010521 absorption reaction Methods 0.000 description 4
- 125000003342 alkenyl group Chemical group 0.000 description 4
- 125000005428 anthryl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C3C(*)=C([H])C([H])=C([H])C3=C([H])C2=C1[H] 0.000 description 4
- 239000003054 catalyst Substances 0.000 description 4
- 238000006482 condensation reaction Methods 0.000 description 4
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 4
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 4
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 4
- 238000001312 dry etching Methods 0.000 description 4
- 238000005516 engineering process Methods 0.000 description 4
- 150000002148 esters Chemical class 0.000 description 4
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
- 125000001072 heteroaryl group Chemical group 0.000 description 4
- 238000006460 hydrolysis reaction Methods 0.000 description 4
- 238000006459 hydrosilylation reaction Methods 0.000 description 4
- 125000003136 n-heptyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 4
- KVBGVZZKJNLNJU-UHFFFAOYSA-N naphthalene-2-sulfonic acid Chemical compound C1=CC=CC2=CC(S(=O)(=O)O)=CC=C21 KVBGVZZKJNLNJU-UHFFFAOYSA-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
- 238000010992 reflux Methods 0.000 description 4
- 150000003839 salts Chemical class 0.000 description 4
- 239000002356 single layer Substances 0.000 description 4
- 150000003459 sulfonic acid esters Chemical class 0.000 description 4
- 125000004665 trialkylsilyl group Chemical group 0.000 description 4
- JOLQKTGDSGKSKJ-UHFFFAOYSA-N 1-ethoxypropan-2-ol Chemical compound CCOCC(C)O JOLQKTGDSGKSKJ-UHFFFAOYSA-N 0.000 description 3
- ARXJGSRGQADJSQ-UHFFFAOYSA-N 1-methoxypropan-2-ol Chemical compound COCC(C)O ARXJGSRGQADJSQ-UHFFFAOYSA-N 0.000 description 3
- JHQDBQYFKARISA-UHFFFAOYSA-N 2,2,2-trifluoro-1-(2-methylphenyl)ethanone Chemical compound CC1=CC=CC=C1C(=O)C(F)(F)F JHQDBQYFKARISA-UHFFFAOYSA-N 0.000 description 3
- KJXSTIJHXKFZKV-UHFFFAOYSA-N 2-(cyclohexylmethylsulfanyl)cyclohexan-1-one;trifluoromethanesulfonic acid Chemical compound [O-]S(=O)(=O)C(F)(F)F.O=C1CCCCC1[SH+]CC1CCCCC1 KJXSTIJHXKFZKV-UHFFFAOYSA-N 0.000 description 3
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 3
- ROHFGMGEQXPABC-UHFFFAOYSA-N 3-triethoxysilylbicyclo[2.2.1]heptane-5-carboxylic acid Chemical compound C1C2C([Si](OCC)(OCC)OCC)CC1CC2C(O)=O ROHFGMGEQXPABC-UHFFFAOYSA-N 0.000 description 3
- MIRMQYRFENXIKM-UHFFFAOYSA-N C1CCCCCCCCCCC1.C1CCCCCCCCCCC1.C1CCCCCCCCCCC1.C1CCCCCCCCCCC1.CCCCCCCCCCCC Chemical compound C1CCCCCCCCCCC1.C1CCCCCCCCCCC1.C1CCCCCCCCCCC1.C1CCCCCCCCCCC1.CCCCCCCCCCCC MIRMQYRFENXIKM-UHFFFAOYSA-N 0.000 description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 3
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 3
- 229910004298 SiO 2 Inorganic materials 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 3
- 125000004036 acetal group Chemical group 0.000 description 3
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 3
- 239000003377 acid catalyst Substances 0.000 description 3
- 125000005074 adamantylmethyl group Chemical group 0.000 description 3
- 125000002723 alicyclic group Chemical group 0.000 description 3
- 125000005036 alkoxyphenyl group Chemical group 0.000 description 3
- 125000003282 alkyl amino group Chemical group 0.000 description 3
- 150000001408 amides Chemical class 0.000 description 3
- 125000003277 amino group Chemical group 0.000 description 3
- 238000006664 bond formation reaction Methods 0.000 description 3
- 125000005587 carbonate group Chemical group 0.000 description 3
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 3
- 239000000460 chlorine Substances 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 238000004132 cross linking Methods 0.000 description 3
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
- UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 3
- 238000004090 dissolution Methods 0.000 description 3
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 description 3
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
- 229930195733 hydrocarbon Natural products 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- 238000007654 immersion Methods 0.000 description 3
- 150000002500 ions Chemical class 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 229940098779 methanesulfonic acid Drugs 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- PSZYNBSKGUBXEH-UHFFFAOYSA-N naphthalene-1-sulfonic acid Chemical compound C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-N 0.000 description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 3
- 125000002868 norbornyl group Chemical group C12(CCC(CC1)C2)* 0.000 description 3
- 230000000269 nucleophilic effect Effects 0.000 description 3
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 239000012044 organic layer Substances 0.000 description 3
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 3
- 125000005561 phenanthryl group Chemical group 0.000 description 3
- 238000001020 plasma etching Methods 0.000 description 3
- 238000012545 processing Methods 0.000 description 3
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 3
- 125000006239 protecting group Chemical group 0.000 description 3
- 238000000746 purification Methods 0.000 description 3
- 230000007261 regionalization Effects 0.000 description 3
- 238000004904 shortening Methods 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 125000000547 substituted alkyl group Chemical group 0.000 description 3
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 3
- 125000000101 thioether group Chemical group 0.000 description 3
- ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 description 3
- WMGVPDQNPUQRND-UHFFFAOYSA-N (2-methylphenyl)acetonitrile Chemical compound CC1=CC=CC=C1CC#N WMGVPDQNPUQRND-UHFFFAOYSA-N 0.000 description 2
- 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 2
- XQFGVGNRDPFKFJ-UHFFFAOYSA-N 1,2,3,5,6,7-hexahydropyrrolo[1,2-b]pyridazine Chemical compound N1CCC=C2CCCN21 XQFGVGNRDPFKFJ-UHFFFAOYSA-N 0.000 description 2
- YFISYXOGMSGFRE-UHFFFAOYSA-N 1-(3,4-dimethoxyphenyl)-2,2,2-trifluoroethanone Chemical compound COC1=CC=C(C(=O)C(F)(F)F)C=C1OC YFISYXOGMSGFRE-UHFFFAOYSA-N 0.000 description 2
- SCKJMHAZRHWHTP-UHFFFAOYSA-N 1-(4-benzylphenyl)-2,2,2-trifluoroethanone Chemical compound C1=CC(C(=O)C(F)(F)F)=CC=C1CC1=CC=CC=C1 SCKJMHAZRHWHTP-UHFFFAOYSA-N 0.000 description 2
- FJLUATLTXUNBOT-UHFFFAOYSA-N 1-Hexadecylamine Chemical compound CCCCCCCCCCCCCCCCN FJLUATLTXUNBOT-UHFFFAOYSA-N 0.000 description 2
- OXHNLMTVIGZXSG-UHFFFAOYSA-N 1-Methylpyrrole Chemical compound CN1C=CC=C1 OXHNLMTVIGZXSG-UHFFFAOYSA-N 0.000 description 2
- WNQSKPOIYILBMI-UHFFFAOYSA-N 1-[butylsulfonyl(diazo)methyl]sulfonylbutane Chemical compound CCCCS(=O)(=O)C(=[N+]=[N-])S(=O)(=O)CCCC WNQSKPOIYILBMI-UHFFFAOYSA-N 0.000 description 2
- GYQQFWWMZYBCIB-UHFFFAOYSA-N 1-[diazo-(4-methylphenyl)sulfonylmethyl]sulfonyl-4-methylbenzene Chemical compound C1=CC(C)=CC=C1S(=O)(=O)C(=[N+]=[N-])S(=O)(=O)C1=CC=C(C)C=C1 GYQQFWWMZYBCIB-UHFFFAOYSA-N 0.000 description 2
- 238000005160 1H NMR spectroscopy Methods 0.000 description 2
- PAPNRQCYSFBWDI-UHFFFAOYSA-N 2,5-Dimethyl-1H-pyrrole Chemical compound CC1=CC=C(C)N1 PAPNRQCYSFBWDI-UHFFFAOYSA-N 0.000 description 2
- VZSRBBMJRBPUNF-UHFFFAOYSA-N 2-(2,3-dihydro-1H-inden-2-ylamino)-N-[3-oxo-3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propyl]pyrimidine-5-carboxamide Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C(=O)NCCC(N1CC2=C(CC1)NN=N2)=O VZSRBBMJRBPUNF-UHFFFAOYSA-N 0.000 description 2
- KKOOSMDBEULUDH-UHFFFAOYSA-N 2-[butan-2-ylsulfonyl(diazo)methyl]sulfonylbutane Chemical compound CCC(C)S(=O)(=O)C(=[N+]=[N-])S(=O)(=O)C(C)CC KKOOSMDBEULUDH-UHFFFAOYSA-N 0.000 description 2
- DRYBUHKBBRHEAE-UHFFFAOYSA-N 2-[diazo(propan-2-ylsulfonyl)methyl]sulfonylpropane Chemical compound CC(C)S(=O)(=O)C(=[N+]=[N-])S(=O)(=O)C(C)C DRYBUHKBBRHEAE-UHFFFAOYSA-N 0.000 description 2
- SAFWZKVQMVOANB-UHFFFAOYSA-N 2-[tert-butylsulfonyl(diazo)methyl]sulfonyl-2-methylpropane Chemical compound CC(C)(C)S(=O)(=O)C(=[N+]=[N-])S(=O)(=O)C(C)(C)C SAFWZKVQMVOANB-UHFFFAOYSA-N 0.000 description 2
- 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 description 2
- KDSNLYIMUZNERS-UHFFFAOYSA-N 2-methylpropanamine Chemical compound CC(C)CN KDSNLYIMUZNERS-UHFFFAOYSA-N 0.000 description 2
- VQGHOUODWALEFC-UHFFFAOYSA-N 2-phenylpyridine Chemical compound C1=CC=CC=C1C1=CC=CC=N1 VQGHOUODWALEFC-UHFFFAOYSA-N 0.000 description 2
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 2
- NXCPNMMVLIOWCK-UHFFFAOYSA-N 3,3,3-trifluoro-2-(trifluoromethyl)propane-1,2-diol Chemical compound OCC(O)(C(F)(F)F)C(F)(F)F NXCPNMMVLIOWCK-UHFFFAOYSA-N 0.000 description 2
- JJYPMNFTHPTTDI-UHFFFAOYSA-N 3-methylaniline Chemical compound CC1=CC=CC(N)=C1 JJYPMNFTHPTTDI-UHFFFAOYSA-N 0.000 description 2
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 description 2
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 2
- YXZXRYDYTRYFAF-UHFFFAOYSA-M 4-methylbenzenesulfonate;triphenylsulfanium Chemical compound CC1=CC=C(S([O-])(=O)=O)C=C1.C1=CC=CC=C1[S+](C=1C=CC=CC=1)C1=CC=CC=C1 YXZXRYDYTRYFAF-UHFFFAOYSA-M 0.000 description 2
- MJGQMEJOQAULGB-UHFFFAOYSA-M 4-methylbenzenesulfonate;tris[4-[(2-methylpropan-2-yl)oxy]phenyl]sulfanium Chemical compound CC1=CC=C(S([O-])(=O)=O)C=C1.C1=CC(OC(C)(C)C)=CC=C1[S+](C=1C=CC(OC(C)(C)C)=CC=1)C1=CC=C(OC(C)(C)C)C=C1 MJGQMEJOQAULGB-UHFFFAOYSA-M 0.000 description 2
- XLSZMDLNRCVEIJ-UHFFFAOYSA-N 4-methylimidazole Chemical compound CC1=CNC=N1 XLSZMDLNRCVEIJ-UHFFFAOYSA-N 0.000 description 2
- 125000000590 4-methylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 2
- FFWSICBKRCICMR-UHFFFAOYSA-N 5-methyl-2-hexanone Chemical compound CC(C)CCC(C)=O FFWSICBKRCICMR-UHFFFAOYSA-N 0.000 description 2
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 2
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 2
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-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
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 2
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- KDXKERNSBIXSRK-YFKPBYRVSA-N L-lysine Chemical compound NCCCC[C@H](N)C(O)=O KDXKERNSBIXSRK-YFKPBYRVSA-N 0.000 description 2
- KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 description 2
- 239000004472 Lysine Substances 0.000 description 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
- JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 2
- AFBPFSWMIHJQDM-UHFFFAOYSA-N N-methylaniline Chemical compound CNC1=CC=CC=C1 AFBPFSWMIHJQDM-UHFFFAOYSA-N 0.000 description 2
- ATHHXGZTWNVVOU-UHFFFAOYSA-N N-methylformamide Chemical compound CNC=O ATHHXGZTWNVVOU-UHFFFAOYSA-N 0.000 description 2
- PVNIIMVLHYAWGP-UHFFFAOYSA-N Niacin Chemical compound OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- 239000004793 Polystyrene Substances 0.000 description 2
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 2
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
- 229910004541 SiN Inorganic materials 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 2
- GLGXSTXZLFQYKJ-UHFFFAOYSA-N [cyclohexylsulfonyl(diazo)methyl]sulfonylcyclohexane Chemical compound C1CCCCC1S(=O)(=O)C(=[N+]=[N-])S(=O)(=O)C1CCCCC1 GLGXSTXZLFQYKJ-UHFFFAOYSA-N 0.000 description 2
- 125000001539 acetonyl group Chemical group [H]C([H])([H])C(=O)C([H])([H])* 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 125000004423 acyloxy group Chemical group 0.000 description 2
- ORILYTVJVMAKLC-UHFFFAOYSA-N adamantane Chemical compound C1C(C2)CC3CC1CC2C3 ORILYTVJVMAKLC-UHFFFAOYSA-N 0.000 description 2
- 230000001476 alcoholic effect Effects 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 125000004450 alkenylene group Chemical group 0.000 description 2
- 125000004183 alkoxy alkyl group Chemical group 0.000 description 2
- 125000005037 alkyl phenyl group Chemical group 0.000 description 2
- 125000004414 alkyl thio group Chemical group 0.000 description 2
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 2
- 229910021529 ammonia Inorganic materials 0.000 description 2
- HOPRXXXSABQWAV-UHFFFAOYSA-N anhydrous collidine Natural products CC1=CC=NC(C)=C1C HOPRXXXSABQWAV-UHFFFAOYSA-N 0.000 description 2
- 150000004982 aromatic amines Chemical class 0.000 description 2
- 125000000732 arylene group Chemical group 0.000 description 2
- 125000005355 arylox oalkyl group Chemical group 0.000 description 2
- 125000004429 atom Chemical group 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- 229940092714 benzenesulfonic acid Drugs 0.000 description 2
- WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 2
- 150000004657 carbamic acid derivatives Chemical class 0.000 description 2
- 239000011203 carbon fibre reinforced carbon Substances 0.000 description 2
- 125000001309 chloro group Chemical group Cl* 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 238000013329 compounding Methods 0.000 description 2
- 238000007796 conventional method Methods 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 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 2
- PAFZNILMFXTMIY-UHFFFAOYSA-N cyclohexylamine Chemical compound NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 description 2
- 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 description 2
- DIOQZVSQGTUSAI-UHFFFAOYSA-N decane Chemical compound CCCCCCCCCC DIOQZVSQGTUSAI-UHFFFAOYSA-N 0.000 description 2
- JQVDAXLFBXTEQA-UHFFFAOYSA-N dibutylamine Chemical compound CCCCNCCCC JQVDAXLFBXTEQA-UHFFFAOYSA-N 0.000 description 2
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 2
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 2
- 238000009792 diffusion process Methods 0.000 description 2
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 2
- 125000005982 diphenylmethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 2
- LTYMSROWYAPPGB-UHFFFAOYSA-O diphenylsulfanium Chemical compound C=1C=CC=CC=1[SH+]C1=CC=CC=C1 LTYMSROWYAPPGB-UHFFFAOYSA-O 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
- 238000011156 evaluation Methods 0.000 description 2
- NBVXSUQYWXRMNV-UHFFFAOYSA-N fluoromethane Chemical compound FC NBVXSUQYWXRMNV-UHFFFAOYSA-N 0.000 description 2
- 239000012634 fragment Substances 0.000 description 2
- 238000002290 gas chromatography-mass spectrometry Methods 0.000 description 2
- 125000000623 heterocyclic group Chemical group 0.000 description 2
- 125000004836 hexamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 125000004464 hydroxyphenyl group Chemical group 0.000 description 2
- 150000003949 imides Chemical class 0.000 description 2
- 125000001841 imino group Chemical group [H]N=* 0.000 description 2
- IVYPNXXAYMYVSP-UHFFFAOYSA-N indole-3-methanol Chemical compound C1=CC=C2C(CO)=CNC2=C1 IVYPNXXAYMYVSP-UHFFFAOYSA-N 0.000 description 2
- 125000003253 isopropoxy group Chemical group [H]C([H])([H])C([H])(O*)C([H])([H])[H] 0.000 description 2
- 150000002576 ketones Chemical class 0.000 description 2
- 125000000686 lactone group Chemical group 0.000 description 2
- 125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- GZNNMGJAIPPJBM-UHFFFAOYSA-N methyl 3,3,3-trifluoro-2-hydroxy-2-(trifluoromethyl)propanoate Chemical compound COC(=O)C(O)(C(F)(F)F)C(F)(F)F GZNNMGJAIPPJBM-UHFFFAOYSA-N 0.000 description 2
- JDEJGVSZUIJWBM-UHFFFAOYSA-N n,n,2-trimethylaniline Chemical compound CN(C)C1=CC=CC=C1C JDEJGVSZUIJWBM-UHFFFAOYSA-N 0.000 description 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
- CDZOGLJOFWFVOZ-UHFFFAOYSA-N n-propylaniline Chemical compound CCCNC1=CC=CC=C1 CDZOGLJOFWFVOZ-UHFFFAOYSA-N 0.000 description 2
- 230000007935 neutral effect Effects 0.000 description 2
- IZJVVXCHJIQVOL-UHFFFAOYSA-N nitro(phenyl)methanesulfonic acid Chemical class OS(=O)(=O)C([N+]([O-])=O)C1=CC=CC=C1 IZJVVXCHJIQVOL-UHFFFAOYSA-N 0.000 description 2
- 229920003986 novolac Polymers 0.000 description 2
- RNVCVTLRINQCPJ-UHFFFAOYSA-N o-toluidine Chemical compound CC1=CC=CC=C1N RNVCVTLRINQCPJ-UHFFFAOYSA-N 0.000 description 2
- 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 description 2
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 2
- RZXMPPFPUUCRFN-UHFFFAOYSA-N p-toluidine Chemical compound CC1=CC=C(N)C=C1 RZXMPPFPUUCRFN-UHFFFAOYSA-N 0.000 description 2
- DPBLXKKOBLCELK-UHFFFAOYSA-N pentan-1-amine Chemical compound CCCCCN DPBLXKKOBLCELK-UHFFFAOYSA-N 0.000 description 2
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 2
- SUSQOBVLVYHIEX-UHFFFAOYSA-N phenylacetonitrile Chemical compound N#CCC1=CC=CC=C1 SUSQOBVLVYHIEX-UHFFFAOYSA-N 0.000 description 2
- 229920002120 photoresistant polymer Polymers 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- 229920002223 polystyrene Polymers 0.000 description 2
- 150000003139 primary aliphatic amines Chemical class 0.000 description 2
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 2
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 2
- UBQKCCHYAOITMY-UHFFFAOYSA-N pyridin-2-ol Chemical compound OC1=CC=CC=N1 UBQKCCHYAOITMY-UHFFFAOYSA-N 0.000 description 2
- 150000005619 secondary aliphatic amines Chemical class 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 125000003107 substituted aryl group Chemical group 0.000 description 2
- 238000006467 substitution reaction Methods 0.000 description 2
- KZNICNPSHKQLFF-UHFFFAOYSA-N succinimide Chemical compound O=C1CCC(=O)N1 KZNICNPSHKQLFF-UHFFFAOYSA-N 0.000 description 2
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 description 2
- RWSOTUBLDIXVET-UHFFFAOYSA-O sulfonium Chemical compound [SH3+] RWSOTUBLDIXVET-UHFFFAOYSA-O 0.000 description 2
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 2
- 150000003510 tertiary aliphatic amines Chemical class 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- 125000003396 thiol group Chemical group [H]S* 0.000 description 2
- 229910052718 tin Inorganic materials 0.000 description 2
- QQQSFSZALRVCSZ-UHFFFAOYSA-N triethoxysilane Chemical compound CCO[SiH](OCC)OCC QQQSFSZALRVCSZ-UHFFFAOYSA-N 0.000 description 2
- YUYCVXFAYWRXLS-UHFFFAOYSA-N trimethoxysilane Chemical compound CO[SiH](OC)OC YUYCVXFAYWRXLS-UHFFFAOYSA-N 0.000 description 2
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 2
- 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 2
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- FNGOYZKCMRJOHA-UHFFFAOYSA-N (2,3-dimethylphenyl) 4-methylbenzenesulfonate Chemical compound C1=CC(C)=CC=C1S(=O)(=O)OC1=CC=CC(C)=C1C FNGOYZKCMRJOHA-UHFFFAOYSA-N 0.000 description 1
- GCIYMCNGLUNWNR-UHFFFAOYSA-N (2,4-dinitrophenyl)methyl 4-methylbenzenesulfonate Chemical compound C1=CC(C)=CC=C1S(=O)(=O)OCC1=CC=C([N+]([O-])=O)C=C1[N+]([O-])=O GCIYMCNGLUNWNR-UHFFFAOYSA-N 0.000 description 1
- MCJPJAJHPRCILL-UHFFFAOYSA-N (2,6-dinitrophenyl)methyl 4-methylbenzenesulfonate Chemical compound C1=CC(C)=CC=C1S(=O)(=O)OCC1=C([N+]([O-])=O)C=CC=C1[N+]([O-])=O MCJPJAJHPRCILL-UHFFFAOYSA-N 0.000 description 1
- FEBGMAXIQMQKCB-UHFFFAOYSA-N (2-methoxy-2-oxoethyl) 3-[bis(2-acetyloxyethyl)amino]propanoate Chemical compound COC(=O)COC(=O)CCN(CCOC(C)=O)CCOC(C)=O FEBGMAXIQMQKCB-UHFFFAOYSA-N 0.000 description 1
- IOLNSDKWTPJYDO-UHFFFAOYSA-N (2-methoxy-2-oxoethyl) 3-[bis(2-hydroxyethyl)amino]propanoate Chemical compound COC(=O)COC(=O)CCN(CCO)CCO IOLNSDKWTPJYDO-UHFFFAOYSA-N 0.000 description 1
- NIZONLAIJCNVBD-UHFFFAOYSA-N (2-oxooxolan-3-yl) 3-[bis(2-acetyloxyethyl)amino]propanoate Chemical compound CC(=O)OCCN(CCOC(C)=O)CCC(=O)OC1CCOC1=O NIZONLAIJCNVBD-UHFFFAOYSA-N 0.000 description 1
- RBGBQMOBKHHECH-VKHMYHEASA-N (2s)-2-(methoxyamino)propanoic acid Chemical compound CON[C@@H](C)C(O)=O RBGBQMOBKHHECH-VKHMYHEASA-N 0.000 description 1
- NCBOCTJTXKCXFY-UHFFFAOYSA-N (3-amino-3-cyanopropyl) acetate Chemical compound CC(=O)OCCC(N)C#N NCBOCTJTXKCXFY-UHFFFAOYSA-N 0.000 description 1
- HXMDFDFPGNMPMX-UHFFFAOYSA-N (3-amino-3-cyanopropyl) formate Chemical compound N#CC(N)CCOC=O HXMDFDFPGNMPMX-UHFFFAOYSA-N 0.000 description 1
- ONAOTAXCIBIMTP-UHFFFAOYSA-N (4-amino-3-cyanobutyl) acetate Chemical compound C(C)(=O)OCCC(C#N)CN ONAOTAXCIBIMTP-UHFFFAOYSA-N 0.000 description 1
- RSJQHQQTFMPRAV-UHFFFAOYSA-N (4-amino-3-cyanobutyl) formate Chemical compound C(=O)OCCC(C#N)CN RSJQHQQTFMPRAV-UHFFFAOYSA-N 0.000 description 1
- DLQPKWPSFFLCCR-UHFFFAOYSA-N 1,1,1-trifluoro-3-methyl-2-(trifluoromethyl)butane-2,3-diol Chemical compound CC(C)(O)C(O)(C(F)(F)F)C(F)(F)F DLQPKWPSFFLCCR-UHFFFAOYSA-N 0.000 description 1
- UJPMYEOUBPIPHQ-UHFFFAOYSA-N 1,1,1-trifluoroethane Chemical compound CC(F)(F)F UJPMYEOUBPIPHQ-UHFFFAOYSA-N 0.000 description 1
- JGTNAGYHADQMCM-UHFFFAOYSA-M 1,1,2,2,3,3,4,4,4-nonafluorobutane-1-sulfonate Chemical compound [O-]S(=O)(=O)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F JGTNAGYHADQMCM-UHFFFAOYSA-M 0.000 description 1
- 150000005045 1,10-phenanthrolines Chemical class 0.000 description 1
- LEEANUDEDHYDTG-UHFFFAOYSA-N 1,2-dimethoxypropane Chemical compound COCC(C)OC LEEANUDEDHYDTG-UHFFFAOYSA-N 0.000 description 1
- 125000002030 1,2-phenylene group Chemical group [H]C1=C([H])C([*:1])=C([*:2])C([H])=C1[H] 0.000 description 1
- GEYOCULIXLDCMW-UHFFFAOYSA-N 1,2-phenylenediamine Chemical compound NC1=CC=CC=C1N GEYOCULIXLDCMW-UHFFFAOYSA-N 0.000 description 1
- GXQDWDBEBPVVPE-UHFFFAOYSA-N 1,3,4,5,6-pentafluorocyclohexa-2,4-diene-1-sulfonic acid Chemical compound OS(=O)(=O)C1(F)C=C(F)C(F)=C(F)C1F GXQDWDBEBPVVPE-UHFFFAOYSA-N 0.000 description 1
- 125000005838 1,3-cyclopentylene group Chemical group [H]C1([H])C([H])([H])C([H])([*:2])C([H])([H])C1([H])[*:1] 0.000 description 1
- NBXKUSNBCPPKRA-UHFFFAOYSA-N 1,4,7,10,13-pentaoxa-16-azacyclooctadecane Chemical compound C1COCCOCCOCCOCCOCCN1 NBXKUSNBCPPKRA-UHFFFAOYSA-N 0.000 description 1
- BJUOQSZSDIHZNP-UHFFFAOYSA-N 1,4,7,10-tetraoxa-13-azacyclopentadecane Chemical compound C1COCCOCCOCCOCCN1 BJUOQSZSDIHZNP-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- 125000004955 1,4-cyclohexylene group Chemical group [H]C1([H])C([H])([H])C([H])([*:1])C([H])([H])C([H])([H])C1([H])[*:2] 0.000 description 1
- FLNQAPQQAZVRDA-UHFFFAOYSA-N 1-(2-(2-Hydroxyethoxy)ethyl)piperazine Chemical compound OCCOCCN1CCNCC1 FLNQAPQQAZVRDA-UHFFFAOYSA-N 0.000 description 1
- WDQFELCEOPFLCZ-UHFFFAOYSA-N 1-(2-hydroxyethyl)pyrrolidin-2-one Chemical compound OCCN1CCCC1=O WDQFELCEOPFLCZ-UHFFFAOYSA-N 0.000 description 1
- DYPQUENOGZXOGE-UHFFFAOYSA-N 1-(4-chlorophenyl)-2,2,2-trifluoroethanone Chemical compound FC(F)(F)C(=O)C1=CC=C(Cl)C=C1 DYPQUENOGZXOGE-UHFFFAOYSA-N 0.000 description 1
- PZVBUCIVSPSAAL-UHFFFAOYSA-N 1-(4-ethoxy-3,5-dimethylphenyl)-2,2,2-trifluoroethanone Chemical compound CCOC1=C(C)C=C(C(=O)C(F)(F)F)C=C1C PZVBUCIVSPSAAL-UHFFFAOYSA-N 0.000 description 1
- JEIHSRORUWXJGF-UHFFFAOYSA-N 1-[(2-methylpropan-2-yl)oxy]propan-2-yl acetate Chemical compound CC(=O)OC(C)COC(C)(C)C JEIHSRORUWXJGF-UHFFFAOYSA-N 0.000 description 1
- NKIWSDRSTPWUHG-UHFFFAOYSA-N 1-[2-(2-methoxyethoxymethoxy)ethyl]piperidine Chemical compound COCCOCOCCN1CCCCC1 NKIWSDRSTPWUHG-UHFFFAOYSA-N 0.000 description 1
- UMVLAFUCAJHPHY-UHFFFAOYSA-N 1-[2-(2-methoxyethoxymethoxy)ethyl]pyrrolidine Chemical compound COCCOCOCCN1CCCC1 UMVLAFUCAJHPHY-UHFFFAOYSA-N 0.000 description 1
- MHRHOLZTKDOBMG-UHFFFAOYSA-N 1-[2-(methoxymethoxy)ethyl]piperidine Chemical compound COCOCCN1CCCCC1 MHRHOLZTKDOBMG-UHFFFAOYSA-N 0.000 description 1
- GCBSYFJJZJJUBC-UHFFFAOYSA-N 1-[2-(methoxymethoxy)ethyl]pyrrolidine Chemical compound COCOCCN1CCCC1 GCBSYFJJZJJUBC-UHFFFAOYSA-N 0.000 description 1
- GLYOFBNLYMTEPS-UHFFFAOYSA-N 1-[diazo(2-methylpropylsulfonyl)methyl]sulfonyl-2-methylpropane Chemical compound CC(C)CS(=O)(=O)C(=[N+]=[N-])S(=O)(=O)CC(C)C GLYOFBNLYMTEPS-UHFFFAOYSA-N 0.000 description 1
- WUYAQJZXAJBVFT-UHFFFAOYSA-N 1-[diazo(propylsulfonyl)methyl]sulfonylpropane Chemical compound CCCS(=O)(=O)C(=[N+]=[N-])S(=O)(=O)CCC WUYAQJZXAJBVFT-UHFFFAOYSA-N 0.000 description 1
- APDQMXRYEXVECM-UHFFFAOYSA-N 1-[tert-butylsulfonyl(diazo)methyl]sulfonylhexane Chemical compound C(CCCCC)S(=O)(=O)C(S(=O)(=O)C(C)(C)C)=[N+]=[N-] APDQMXRYEXVECM-UHFFFAOYSA-N 0.000 description 1
- 125000004973 1-butenyl group Chemical group C(=CCC)* 0.000 description 1
- DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical compound CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 description 1
- DDPLKUDCQKROTF-UHFFFAOYSA-N 1-cyclohexyl-2-methyl-2-(4-methylphenyl)sulfonylpropan-1-one Chemical compound C1=CC(C)=CC=C1S(=O)(=O)C(C)(C)C(=O)C1CCCCC1 DDPLKUDCQKROTF-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
- BMVXCPBXGZKUPN-UHFFFAOYSA-N 1-hexanamine Chemical compound CCCCCCN BMVXCPBXGZKUPN-UHFFFAOYSA-N 0.000 description 1
- 125000006039 1-hexenyl group Chemical group 0.000 description 1
- NYQIHTIWGPMKHT-UHFFFAOYSA-N 1-hydroxypyrrolidine-2,5-dione;4-methylbenzenesulfonic acid Chemical compound ON1C(=O)CCC1=O.CC1=CC=C(S(O)(=O)=O)C=C1 NYQIHTIWGPMKHT-UHFFFAOYSA-N 0.000 description 1
- FFKFRQVYUILJCW-UHFFFAOYSA-N 1-hydroxypyrrolidine-2,5-dione;methanesulfonic acid Chemical compound CS(O)(=O)=O.ON1C(=O)CCC1=O FFKFRQVYUILJCW-UHFFFAOYSA-N 0.000 description 1
- VCVDBBLMXDOXEY-UHFFFAOYSA-N 1-hydroxypyrrolidine-2,5-dione;naphthalene-1-sulfonic acid Chemical compound ON1C(=O)CCC1=O.C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 VCVDBBLMXDOXEY-UHFFFAOYSA-N 0.000 description 1
- SSVBQZNCZVTJPT-UHFFFAOYSA-N 1-hydroxypyrrolidine-2,5-dione;naphthalene-2-sulfonic acid Chemical compound ON1C(=O)CCC1=O.C1=CC=CC2=CC(S(=O)(=O)O)=CC=C21 SSVBQZNCZVTJPT-UHFFFAOYSA-N 0.000 description 1
- XAJXGUBHPFWEIH-UHFFFAOYSA-N 1-hydroxypyrrolidine-2,5-dione;pentane-1-sulfonic acid Chemical compound ON1C(=O)CCC1=O.CCCCCS(O)(=O)=O XAJXGUBHPFWEIH-UHFFFAOYSA-N 0.000 description 1
- GQKQQNRKHNXSSO-UHFFFAOYSA-N 1-hydroxypyrrolidine-2,5-dione;propane-1-sulfonic acid Chemical compound CCCS(O)(=O)=O.ON1C(=O)CCC1=O GQKQQNRKHNXSSO-UHFFFAOYSA-N 0.000 description 1
- KCPXFMZEOQLCPM-UHFFFAOYSA-N 1-hydroxypyrrolidine-2,5-dione;propane-2-sulfonic acid Chemical compound CC(C)S(O)(=O)=O.ON1C(=O)CCC1=O KCPXFMZEOQLCPM-UHFFFAOYSA-N 0.000 description 1
- WXPWTKPQXYLOJH-UHFFFAOYSA-N 1-methoxy-4-(4-methoxyphenyl)sulfonylbenzene Chemical compound C1=CC(OC)=CC=C1S(=O)(=O)C1=CC=C(OC)C=C1 WXPWTKPQXYLOJH-UHFFFAOYSA-N 0.000 description 1
- XLOXYWLRAKCDQL-UHFFFAOYSA-N 1-methyl-4-[(4-methylphenyl)sulfonylmethylsulfonyl]benzene Chemical compound C1=CC(C)=CC=C1S(=O)(=O)CS(=O)(=O)C1=CC=C(C)C=C1 XLOXYWLRAKCDQL-UHFFFAOYSA-N 0.000 description 1
- AVFZOVWCLRSYKC-UHFFFAOYSA-N 1-methylpyrrolidine Chemical compound CN1CCCC1 AVFZOVWCLRSYKC-UHFFFAOYSA-N 0.000 description 1
- RUFPHBVGCFYCNW-UHFFFAOYSA-N 1-naphthylamine Chemical compound C1=CC=C2C(N)=CC=CC2=C1 RUFPHBVGCFYCNW-UHFFFAOYSA-N 0.000 description 1
- KWKAKUADMBZCLK-UHFFFAOYSA-N 1-octene Chemical group CCCCCCC=C KWKAKUADMBZCLK-UHFFFAOYSA-N 0.000 description 1
- 125000006023 1-pentenyl group Chemical group 0.000 description 1
- 125000006017 1-propenyl group Chemical group 0.000 description 1
- BAXOFTOLAUCFNW-UHFFFAOYSA-N 1H-indazole Chemical class C1=CC=C2C=NNC2=C1 BAXOFTOLAUCFNW-UHFFFAOYSA-N 0.000 description 1
- JCWQTARLYJDDRE-UHFFFAOYSA-N 2,2,2-trifluoro-1-(4-methylsulfanylphenyl)ethanone Chemical compound CSC1=CC=C(C(=O)C(F)(F)F)C=C1 JCWQTARLYJDDRE-UHFFFAOYSA-N 0.000 description 1
- ZSOFAYWPBVQQFQ-UHFFFAOYSA-N 2,2,2-trifluoro-1-(4-methylsulfonylphenyl)ethanone Chemical compound CS(=O)(=O)C1=CC=C(C(=O)C(F)(F)F)C=C1 ZSOFAYWPBVQQFQ-UHFFFAOYSA-N 0.000 description 1
- OSXBYCLYYVYZOX-UHFFFAOYSA-N 2,2,2-trifluoro-1-(4-phenylmethoxyphenyl)ethanone Chemical compound C1=CC(C(=O)C(F)(F)F)=CC=C1OCC1=CC=CC=C1 OSXBYCLYYVYZOX-UHFFFAOYSA-N 0.000 description 1
- BMVJZJPRNPFVCH-UHFFFAOYSA-N 2,2,2-trifluoro-1-[4-(2-phenoxyethoxy)phenyl]ethanone Chemical compound C1=CC(C(=O)C(F)(F)F)=CC=C1OCCOC1=CC=CC=C1 BMVJZJPRNPFVCH-UHFFFAOYSA-N 0.000 description 1
- CZYKJGCKVBXLGF-UHFFFAOYSA-N 2,2,2-trifluoro-1-thiophen-2-ylethanone Chemical compound FC(F)(F)C(=O)C1=CC=CS1 CZYKJGCKVBXLGF-UHFFFAOYSA-N 0.000 description 1
- AVSVJSGDSPDFLH-UHFFFAOYSA-N 2,2,2-trifluoroethylbenzene Chemical compound FC(F)(F)CC1=CC=CC=C1 AVSVJSGDSPDFLH-UHFFFAOYSA-N 0.000 description 1
- WBDPKZCMVAISAL-UHFFFAOYSA-N 2,3,4-triethylpyridine Chemical compound CCC1=CC=NC(CC)=C1CC WBDPKZCMVAISAL-UHFFFAOYSA-N 0.000 description 1
- QHUHPERZCBUMRK-UHFFFAOYSA-N 2,3-dimethoxypyridine Chemical compound COC1=CC=CN=C1OC QHUHPERZCBUMRK-UHFFFAOYSA-N 0.000 description 1
- WKAXDAMWMOBXMP-UHFFFAOYSA-N 2,3-diphenylpyridine Chemical compound C1=CC=CC=C1C1=CC=CN=C1C1=CC=CC=C1 WKAXDAMWMOBXMP-UHFFFAOYSA-N 0.000 description 1
- MOLRNXJUYCXJTN-UHFFFAOYSA-N 2,4-dimethyl-2-(4-methylphenyl)sulfonylpentan-3-one Chemical compound CC(C)C(=O)C(C)(C)S(=O)(=O)C1=CC=C(C)C=C1 MOLRNXJUYCXJTN-UHFFFAOYSA-N 0.000 description 1
- LXQOQPGNCGEELI-UHFFFAOYSA-N 2,4-dinitroaniline Chemical compound NC1=CC=C([N+]([O-])=O)C=C1[N+]([O-])=O LXQOQPGNCGEELI-UHFFFAOYSA-N 0.000 description 1
- QFUSCYRJMXLNRB-UHFFFAOYSA-N 2,6-dinitroaniline Chemical compound NC1=C([N+]([O-])=O)C=CC=C1[N+]([O-])=O QFUSCYRJMXLNRB-UHFFFAOYSA-N 0.000 description 1
- VYONOYYDEFODAJ-UHFFFAOYSA-N 2-(1-Aziridinyl)ethanol Chemical compound OCCN1CC1 VYONOYYDEFODAJ-UHFFFAOYSA-N 0.000 description 1
- FYVMBPXFPFAECB-UHFFFAOYSA-N 2-(1-methylpyrrolidin-2-yl)ethanol Chemical compound CN1CCCC1CCO FYVMBPXFPFAECB-UHFFFAOYSA-N 0.000 description 1
- MWFLUYFYHANMCM-UHFFFAOYSA-N 2-(2-hydroxyethyl)isoindole-1,3-dione Chemical compound C1=CC=C2C(=O)N(CCO)C(=O)C2=C1 MWFLUYFYHANMCM-UHFFFAOYSA-N 0.000 description 1
- XGLVDUUYFKXKPL-UHFFFAOYSA-N 2-(2-methoxyethoxy)-n,n-bis[2-(2-methoxyethoxy)ethyl]ethanamine Chemical compound COCCOCCN(CCOCCOC)CCOCCOC XGLVDUUYFKXKPL-UHFFFAOYSA-N 0.000 description 1
- FWHZIWSDWTWHOE-UHFFFAOYSA-N 2-(aminomethyl)-4-(methoxymethoxy)butanenitrile Chemical compound COCOCCC(C#N)CN FWHZIWSDWTWHOE-UHFFFAOYSA-N 0.000 description 1
- DLVAYGKLIWFILM-UHFFFAOYSA-N 2-(aminomethyl)-4-methoxybutanenitrile Chemical compound COCCC(CN)C#N DLVAYGKLIWFILM-UHFFFAOYSA-N 0.000 description 1
- PCRVZSFUOGJTLM-UHFFFAOYSA-N 2-(aminomethyl)pentanedinitrile Chemical compound NCC(C#N)CCC#N PCRVZSFUOGJTLM-UHFFFAOYSA-N 0.000 description 1
- LVPZSMIBSMMLPI-UHFFFAOYSA-N 2-(diethylamino)acetonitrile Chemical compound CCN(CC)CC#N LVPZSMIBSMMLPI-UHFFFAOYSA-N 0.000 description 1
- NRTKFSQKHCMEMO-UHFFFAOYSA-N 2-(methoxymethoxy)-n,n-bis[2-(methoxymethoxy)ethyl]ethanamine Chemical compound COCOCCN(CCOCOC)CCOCOC NRTKFSQKHCMEMO-UHFFFAOYSA-N 0.000 description 1
- KKFDCBRMNNSAAW-UHFFFAOYSA-N 2-(morpholin-4-yl)ethanol Chemical compound OCCN1CCOCC1 KKFDCBRMNNSAAW-UHFFFAOYSA-N 0.000 description 1
- KZTWONRVIPPDKH-UHFFFAOYSA-N 2-(piperidin-1-yl)ethanol Chemical compound OCCN1CCCCC1 KZTWONRVIPPDKH-UHFFFAOYSA-N 0.000 description 1
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 1
- IZXIZTKNFFYFOF-UHFFFAOYSA-N 2-Oxazolidone Chemical compound O=C1NCCO1 IZXIZTKNFFYFOF-UHFFFAOYSA-N 0.000 description 1
- OIALIKXMLIAOSN-UHFFFAOYSA-N 2-Propylpyridine Chemical compound CCCC1=CC=CC=N1 OIALIKXMLIAOSN-UHFFFAOYSA-N 0.000 description 1
- ZFOHYVABZSHZFF-UHFFFAOYSA-N 2-[(z)-tert-butylsulfonyl(diazo)methyl]sulfonyl-2-methylbutane Chemical class CCC(C)(C)S(=O)(=O)C(=[N+]=[N-])S(=O)(=O)C(C)(C)C ZFOHYVABZSHZFF-UHFFFAOYSA-N 0.000 description 1
- SIWDZKLZIXWZHP-UHFFFAOYSA-N 2-[bis(2-acetyloxyethyl)amino]ethyl 2-acetyloxyacetate Chemical compound CC(=O)OCCN(CCOC(C)=O)CCOC(=O)COC(C)=O SIWDZKLZIXWZHP-UHFFFAOYSA-N 0.000 description 1
- YLNHOJPBLKPYLM-UHFFFAOYSA-N 2-[bis(2-butanoyloxyethyl)amino]ethyl butanoate Chemical compound CCCC(=O)OCCN(CCOC(=O)CCC)CCOC(=O)CCC YLNHOJPBLKPYLM-UHFFFAOYSA-N 0.000 description 1
- IIBYXAJIXZFSSE-UHFFFAOYSA-N 2-[diazo(2-methylbutan-2-ylsulfonyl)methyl]sulfonyl-2-methylbutane Chemical compound CCC(C)(C)S(=O)(=O)C(=[N+]=[N-])S(=O)(=O)C(C)(C)CC IIBYXAJIXZFSSE-UHFFFAOYSA-N 0.000 description 1
- FTPALKUEAPIMPZ-UHFFFAOYSA-N 2-[diazo(pentan-2-ylsulfonyl)methyl]sulfonylpentane Chemical compound CCCC(C)S(=O)(=O)C(=[N+]=[N-])S(=O)(=O)C(C)CCC FTPALKUEAPIMPZ-UHFFFAOYSA-N 0.000 description 1
- WILHWJCFXRWDIT-UHFFFAOYSA-N 2-acetyloxyethyl 3-[bis(2-acetyloxyethyl)amino]propanoate Chemical compound CC(=O)OCCOC(=O)CCN(CCOC(C)=O)CCOC(C)=O WILHWJCFXRWDIT-UHFFFAOYSA-N 0.000 description 1
- OQTRAYNNXPMMIT-UHFFFAOYSA-N 2-acetyloxyethyl 3-morpholin-4-ylpropanoate Chemical compound CC(=O)OCCOC(=O)CCN1CCOCC1 OQTRAYNNXPMMIT-UHFFFAOYSA-N 0.000 description 1
- QFPYWIXREIQTOD-UHFFFAOYSA-N 2-amino-4-hydroxybutanenitrile Chemical compound N#CC(N)CCO QFPYWIXREIQTOD-UHFFFAOYSA-N 0.000 description 1
- YHGPQUBSJFECHI-UHFFFAOYSA-N 2-amino-4-methoxybutanenitrile Chemical compound COCCC(N)C#N YHGPQUBSJFECHI-UHFFFAOYSA-N 0.000 description 1
- PCFUWBOSXMKGIP-UHFFFAOYSA-N 2-benzylpyridine Chemical compound C=1C=CC=NC=1CC1=CC=CC=C1 PCFUWBOSXMKGIP-UHFFFAOYSA-N 0.000 description 1
- OFLSKXBALZCMCX-UHFFFAOYSA-N 2-butoxypyridine Chemical compound CCCCOC1=CC=CC=N1 OFLSKXBALZCMCX-UHFFFAOYSA-N 0.000 description 1
- ADSOSINJPNKUJK-UHFFFAOYSA-N 2-butylpyridine Chemical compound CCCCC1=CC=CC=N1 ADSOSINJPNKUJK-UHFFFAOYSA-N 0.000 description 1
- VPLBMEBNIHGDEH-UHFFFAOYSA-N 2-chloroethanesulfonic acid;1-hydroxypyrrolidine-2,5-dione Chemical compound OS(=O)(=O)CCCl.ON1C(=O)CCC1=O VPLBMEBNIHGDEH-UHFFFAOYSA-N 0.000 description 1
- BFSVOASYOCHEOV-UHFFFAOYSA-N 2-diethylaminoethanol Chemical compound CCN(CC)CCO BFSVOASYOCHEOV-UHFFFAOYSA-N 0.000 description 1
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 1
- NRGGMCIBEHEAIL-UHFFFAOYSA-N 2-ethylpyridine Chemical compound CCC1=CC=CC=N1 NRGGMCIBEHEAIL-UHFFFAOYSA-N 0.000 description 1
- OJLFRIQSJMTSQI-UHFFFAOYSA-N 2-hydroxyethyl 3-[bis(2-hydroxyethyl)amino]propanoate Chemical compound OCCOC(=O)CCN(CCO)CCO OJLFRIQSJMTSQI-UHFFFAOYSA-N 0.000 description 1
- ZKBIJBKTDGKZBN-UHFFFAOYSA-N 2-hydroxyisoindole-1,3-dione;methanesulfonic acid Chemical compound CS(O)(=O)=O.C1=CC=C2C(=O)N(O)C(=O)C2=C1 ZKBIJBKTDGKZBN-UHFFFAOYSA-N 0.000 description 1
- JHRRHLBGYSQONK-UHFFFAOYSA-N 2-methoxyethyl 2-morpholin-4-ylacetate Chemical compound COCCOC(=O)CN1CCOCC1 JHRRHLBGYSQONK-UHFFFAOYSA-N 0.000 description 1
- PSHZXHHHUPZONE-UHFFFAOYSA-N 2-methoxyethyl 2-morpholin-4-ylethyl carbonate Chemical compound COCCOC(=O)OCCN1CCOCC1 PSHZXHHHUPZONE-UHFFFAOYSA-N 0.000 description 1
- UHAMIDBURABUIC-UHFFFAOYSA-N 2-methoxyethyl 3-[bis(2-acetyloxyethyl)amino]propanoate Chemical compound COCCOC(=O)CCN(CCOC(C)=O)CCOC(C)=O UHAMIDBURABUIC-UHFFFAOYSA-N 0.000 description 1
- TYZFXMHAWJEFTK-UHFFFAOYSA-N 2-methoxyethyl 3-morpholin-4-ylpropanoate Chemical compound COCCOC(=O)CCN1CCOCC1 TYZFXMHAWJEFTK-UHFFFAOYSA-N 0.000 description 1
- IWTFOFMTUOBLHG-UHFFFAOYSA-N 2-methoxypyridine Chemical compound COC1=CC=CC=N1 IWTFOFMTUOBLHG-UHFFFAOYSA-N 0.000 description 1
- CTSZPNIMMLSKDV-UHFFFAOYSA-N 2-methyl-1-pyrroline Chemical compound CC1=NCCC1 CTSZPNIMMLSKDV-UHFFFAOYSA-N 0.000 description 1
- IIFFFBSAXDNJHX-UHFFFAOYSA-N 2-methyl-n,n-bis(2-methylpropyl)propan-1-amine Chemical compound CC(C)CN(CC(C)C)CC(C)C IIFFFBSAXDNJHX-UHFFFAOYSA-N 0.000 description 1
- NJBCRXCAPCODGX-UHFFFAOYSA-N 2-methyl-n-(2-methylpropyl)propan-1-amine Chemical compound CC(C)CNCC(C)C NJBCRXCAPCODGX-UHFFFAOYSA-N 0.000 description 1
- GELMWIVBBPAMIO-UHFFFAOYSA-N 2-methylbutan-2-amine Chemical compound CCC(C)(C)N GELMWIVBBPAMIO-UHFFFAOYSA-N 0.000 description 1
- BSKHPKMHTQYZBB-UHFFFAOYSA-N 2-methylpyridine Chemical compound CC1=CC=CC=N1 BSKHPKMHTQYZBB-UHFFFAOYSA-N 0.000 description 1
- QFABNUVNDKOIEH-UHFFFAOYSA-N 2-methylsulfanylcyclohexan-1-one Chemical compound CSC1CCCCC1=O QFABNUVNDKOIEH-UHFFFAOYSA-N 0.000 description 1
- OOSOCAXREAGIGA-UHFFFAOYSA-N 2-morpholin-4-ylacetonitrile Chemical compound N#CCN1CCOCC1 OOSOCAXREAGIGA-UHFFFAOYSA-N 0.000 description 1
- ZDTRMJAWAIZCSV-UHFFFAOYSA-N 2-morpholin-4-ylethyl acetate Chemical compound CC(=O)OCCN1CCOCC1 ZDTRMJAWAIZCSV-UHFFFAOYSA-N 0.000 description 1
- DPJCXCZTLWNFOH-UHFFFAOYSA-N 2-nitroaniline Chemical compound NC1=CC=CC=C1[N+]([O-])=O DPJCXCZTLWNFOH-UHFFFAOYSA-N 0.000 description 1
- 125000004135 2-norbornyl group Chemical group [H]C1([H])C([H])([H])C2([H])C([H])([H])C1([H])C([H])([H])C2([H])* 0.000 description 1
- DXSVEKMQLJOJLA-UHFFFAOYSA-N 2-oxopropyl 3-[bis(2-acetyloxyethyl)amino]propanoate Chemical compound CC(=O)COC(=O)CCN(CCOC(C)=O)CCOC(C)=O DXSVEKMQLJOJLA-UHFFFAOYSA-N 0.000 description 1
- YJMUIOUBJAVDFS-UHFFFAOYSA-N 2-oxopropyl 3-[bis(2-hydroxyethyl)amino]propanoate Chemical compound CC(=O)COC(=O)CCN(CCO)CCO YJMUIOUBJAVDFS-UHFFFAOYSA-N 0.000 description 1
- FTYAXYWEDPWJCJ-UHFFFAOYSA-N 2-pentan-3-ylpyridine Chemical compound CCC(CC)C1=CC=CC=N1 FTYAXYWEDPWJCJ-UHFFFAOYSA-N 0.000 description 1
- WFCSWCVEJLETKA-UHFFFAOYSA-N 2-piperazin-1-ylethanol Chemical compound OCCN1CCNCC1 WFCSWCVEJLETKA-UHFFFAOYSA-N 0.000 description 1
- CLVBVRODHJFTGF-UHFFFAOYSA-N 2-piperidin-1-ylacetonitrile Chemical compound N#CCN1CCCCC1 CLVBVRODHJFTGF-UHFFFAOYSA-N 0.000 description 1
- BJCDLTBTUIMEOQ-UHFFFAOYSA-N 2-piperidin-1-ylethyl acetate Chemical compound CC(=O)OCCN1CCCCC1 BJCDLTBTUIMEOQ-UHFFFAOYSA-N 0.000 description 1
- ZTDDAUJXOBVPMN-UHFFFAOYSA-N 2-piperidin-1-ylethyl propanoate Chemical compound CCC(=O)OCCN1CCCCC1 ZTDDAUJXOBVPMN-UHFFFAOYSA-N 0.000 description 1
- BXGYBSJAZFGIPX-UHFFFAOYSA-N 2-pyridin-2-ylethanol Chemical compound OCCC1=CC=CC=N1 BXGYBSJAZFGIPX-UHFFFAOYSA-N 0.000 description 1
- NPRYXVXVLCYBNS-UHFFFAOYSA-N 2-pyrrolidin-1-ylacetonitrile Chemical compound N#CCN1CCCC1 NPRYXVXVLCYBNS-UHFFFAOYSA-N 0.000 description 1
- UJOVGKWFOULAPW-UHFFFAOYSA-N 2-pyrrolidin-1-ylethyl acetate Chemical compound CC(=O)OCCN1CCCC1 UJOVGKWFOULAPW-UHFFFAOYSA-N 0.000 description 1
- YFZWNECOESTBQL-UHFFFAOYSA-N 2-pyrrolidin-1-ylethyl formate Chemical compound O=COCCN1CCCC1 YFZWNECOESTBQL-UHFFFAOYSA-N 0.000 description 1
- RSEBUVRVKCANEP-UHFFFAOYSA-N 2-pyrroline Chemical compound C1CC=CN1 RSEBUVRVKCANEP-UHFFFAOYSA-N 0.000 description 1
- AUFVJZSDSXXFOI-UHFFFAOYSA-N 2.2.2-cryptand Chemical compound C1COCCOCCN2CCOCCOCCN1CCOCCOCC2 AUFVJZSDSXXFOI-UHFFFAOYSA-N 0.000 description 1
- JZIBVTUXIVIFGC-UHFFFAOYSA-N 2H-pyrrole Chemical compound C1C=CC=N1 JZIBVTUXIVIFGC-UHFFFAOYSA-N 0.000 description 1
- WGTASENVNYJZBK-UHFFFAOYSA-N 3,4,5-trimethoxyamphetamine Chemical compound COC1=CC(CC(C)N)=CC(OC)=C1OC WGTASENVNYJZBK-UHFFFAOYSA-N 0.000 description 1
- MPBZUKLDHPOCLS-UHFFFAOYSA-N 3,5-dinitroaniline Chemical compound NC1=CC([N+]([O-])=O)=CC([N+]([O-])=O)=C1 MPBZUKLDHPOCLS-UHFFFAOYSA-N 0.000 description 1
- YLZOPXRUQYQQID-UHFFFAOYSA-N 3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)-1-[4-[2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidin-5-yl]piperazin-1-yl]propan-1-one Chemical compound N1N=NC=2CN(CCC=21)CCC(=O)N1CCN(CC1)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F YLZOPXRUQYQQID-UHFFFAOYSA-N 0.000 description 1
- LFFKXGFSDGRFQA-UHFFFAOYSA-N 3-(diethylamino)propanenitrile Chemical compound CCN(CC)CCC#N LFFKXGFSDGRFQA-UHFFFAOYSA-N 0.000 description 1
- DIOYEFVIHLBWJX-UHFFFAOYSA-N 3-(diethylamino)propanoic acid Chemical compound CCN(CC)CCC(O)=O DIOYEFVIHLBWJX-UHFFFAOYSA-N 0.000 description 1
- SSZDOZBFTFGNRJ-UHFFFAOYSA-N 3-[bis(2-acetyloxyethyl)amino]propanoic acid Chemical compound CC(=O)OCCN(CCC(O)=O)CCOC(C)=O SSZDOZBFTFGNRJ-UHFFFAOYSA-N 0.000 description 1
- XXQWLJYLTCWMBF-UHFFFAOYSA-N 3-[bis(2-formyloxyethyl)amino]propanoic acid Chemical compound O=COCCN(CCC(=O)O)CCOC=O XXQWLJYLTCWMBF-UHFFFAOYSA-N 0.000 description 1
- HHHQGSPGSZWCEQ-UHFFFAOYSA-N 3-[bis(2-hydroxyethyl)amino]propanoic acid Chemical compound OCCN(CCO)CCC(O)=O HHHQGSPGSZWCEQ-UHFFFAOYSA-N 0.000 description 1
- BICCMIWYAQHGQH-UHFFFAOYSA-N 3-[bis(2-methoxyethyl)azaniumyl]propanoate Chemical compound COCCN(CCOC)CCC(O)=O BICCMIWYAQHGQH-UHFFFAOYSA-N 0.000 description 1
- ZCAZBYJRGHWXKN-UHFFFAOYSA-N 3-[bis[2-(methoxymethoxy)ethyl]amino]propanoic acid Chemical compound COCOCCN(CCC(O)=O)CCOCOC ZCAZBYJRGHWXKN-UHFFFAOYSA-N 0.000 description 1
- FLROJJGKUKLCAE-UHFFFAOYSA-N 3-amino-2-methylphenol Chemical compound CC1=C(N)C=CC=C1O FLROJJGKUKLCAE-UHFFFAOYSA-N 0.000 description 1
- ZAGZIOYVEIDDJA-UHFFFAOYSA-N 3-aminopyrazine-2-carboxylic acid Chemical compound NC1=NC=CN=C1C(O)=O ZAGZIOYVEIDDJA-UHFFFAOYSA-N 0.000 description 1
- OQGRZXSBFFEBQJ-UHFFFAOYSA-M 3-bicyclo[2.2.1]heptanyl-methyl-(2-oxocyclohexyl)sulfanium;trifluoromethanesulfonate Chemical compound [O-]S(=O)(=O)C(F)(F)F.C1C(C2)CCC2C1[S+](C)C1CCCCC1=O OQGRZXSBFFEBQJ-UHFFFAOYSA-M 0.000 description 1
- 125000004975 3-butenyl group Chemical group C(CC=C)* 0.000 description 1
- HICUGGYRYZOXJI-UHFFFAOYSA-N 3-ethylcyclopentene Chemical compound CCC1CCC=C1 HICUGGYRYZOXJI-UHFFFAOYSA-N 0.000 description 1
- 125000006041 3-hexenyl group Chemical group 0.000 description 1
- JSGVZVOGOQILFM-UHFFFAOYSA-N 3-methoxy-1-butanol Chemical compound COC(C)CCO JSGVZVOGOQILFM-UHFFFAOYSA-N 0.000 description 1
- MFKRHJVUCZRDTF-UHFFFAOYSA-N 3-methoxy-3-methylbutan-1-ol Chemical compound COC(C)(C)CCO MFKRHJVUCZRDTF-UHFFFAOYSA-N 0.000 description 1
- BJATUPPYBZHEIO-UHFFFAOYSA-N 3-methyl-2-phenylpyridine Chemical compound CC1=CC=CN=C1C1=CC=CC=C1 BJATUPPYBZHEIO-UHFFFAOYSA-N 0.000 description 1
- PYNCMYJUSGEXEQ-UHFFFAOYSA-N 3-methyl-3-pyrrolidin-1-yloxolan-2-one Chemical compound C1CCCN1C1(C)CCOC1=O PYNCMYJUSGEXEQ-UHFFFAOYSA-N 0.000 description 1
- WXVKGHVDWWXBJX-UHFFFAOYSA-N 3-morpholin-4-ylpropanenitrile Chemical compound N#CCCN1CCOCC1 WXVKGHVDWWXBJX-UHFFFAOYSA-N 0.000 description 1
- YUYHRSGXZZVNMS-UHFFFAOYSA-N 3-morpholin-4-ylpropanoic acid Chemical compound OC(=O)CCN1CCOCC1 YUYHRSGXZZVNMS-UHFFFAOYSA-N 0.000 description 1
- XJCVRTZCHMZPBD-UHFFFAOYSA-N 3-nitroaniline Chemical compound NC1=CC=CC([N+]([O-])=O)=C1 XJCVRTZCHMZPBD-UHFFFAOYSA-N 0.000 description 1
- MECNWXGGNCJFQJ-UHFFFAOYSA-N 3-piperidin-1-ylpropane-1,2-diol Chemical compound OCC(O)CN1CCCCC1 MECNWXGGNCJFQJ-UHFFFAOYSA-N 0.000 description 1
- YZICFVIUVMCCOC-UHFFFAOYSA-N 3-piperidin-1-ylpropanenitrile Chemical compound N#CCCN1CCCCC1 YZICFVIUVMCCOC-UHFFFAOYSA-N 0.000 description 1
- LPDGWMLCUHULJF-UHFFFAOYSA-N 3-piperidin-1-ylpropanoic acid Chemical compound OC(=O)CCN1CCCCC1 LPDGWMLCUHULJF-UHFFFAOYSA-N 0.000 description 1
- MFPZRSWYUKWRIQ-UHFFFAOYSA-N 3-pyrrolidin-1-ylpropane-1,2-diol Chemical compound OCC(O)CN1CCCC1 MFPZRSWYUKWRIQ-UHFFFAOYSA-N 0.000 description 1
- PDVYZQGNSCSKPG-UHFFFAOYSA-N 3-pyrrolidin-1-ylpropanenitrile Chemical compound N#CCCN1CCCC1 PDVYZQGNSCSKPG-UHFFFAOYSA-N 0.000 description 1
- BRSKDXVJFXXUKX-UHFFFAOYSA-N 3-pyrrolidin-1-ylpropanoic acid Chemical compound OC(=O)CCN1CCCC1 BRSKDXVJFXXUKX-UHFFFAOYSA-N 0.000 description 1
- XFGRBBAEAXVKSK-UHFFFAOYSA-N 3-trimethoxysilylbicyclo[2.2.1]heptane-5-carboxylic acid Chemical compound C1C2C([Si](OC)(OC)OC)CC1CC2C(O)=O XFGRBBAEAXVKSK-UHFFFAOYSA-N 0.000 description 1
- LVNQVIZBPSRXAN-UHFFFAOYSA-N 4,7,13,18-tetraoxa-1,10-diazabicyclo[8.5.5]icosane Chemical compound C1COCCOCCN2CCOCCN1CCOCC2 LVNQVIZBPSRXAN-UHFFFAOYSA-N 0.000 description 1
- OPINGEJZOITHCL-UHFFFAOYSA-N 4-(diethylamino)oxan-2-one Chemical compound CCN(CC)C1CCOC(=O)C1 OPINGEJZOITHCL-UHFFFAOYSA-N 0.000 description 1
- LLNPIUABYPBVFJ-UHFFFAOYSA-N 4-[2-(2-methoxyethoxymethoxy)ethyl]morpholine Chemical compound COCCOCOCCN1CCOCC1 LLNPIUABYPBVFJ-UHFFFAOYSA-N 0.000 description 1
- GPNQTMNCYJMZDB-UHFFFAOYSA-N 4-[2-(methoxymethoxy)ethyl]morpholine Chemical compound COCOCCN1CCOCC1 GPNQTMNCYJMZDB-UHFFFAOYSA-N 0.000 description 1
- ALYNCZNDIQEVRV-UHFFFAOYSA-N 4-aminobenzoic acid Chemical compound NC1=CC=C(C(O)=O)C=C1 ALYNCZNDIQEVRV-UHFFFAOYSA-N 0.000 description 1
- RIQNDLCIGMPRCW-UHFFFAOYSA-N 4-aminobutan-1-ol;3-aminopropan-1-ol Chemical compound NCCCO.NCCCCO RIQNDLCIGMPRCW-UHFFFAOYSA-N 0.000 description 1
- GMBSSKQHIDAWCV-UHFFFAOYSA-N 4-diazoheptane Chemical class C(CC)C(=[N+]=[N-])CCC GMBSSKQHIDAWCV-UHFFFAOYSA-N 0.000 description 1
- WVSYONICNIDYBE-UHFFFAOYSA-M 4-fluorobenzenesulfonate Chemical compound [O-]S(=O)(=O)C1=CC=C(F)C=C1 WVSYONICNIDYBE-UHFFFAOYSA-M 0.000 description 1
- IPHKNRHRHVRLTH-UHFFFAOYSA-N 4-formyloxybutyl 3-[bis(2-formyloxyethyl)amino]propanoate Chemical compound O=COCCCCOC(=O)CCN(CCOC=O)CCOC=O IPHKNRHRHVRLTH-UHFFFAOYSA-N 0.000 description 1
- HDHQZCHIXUUSMK-UHFFFAOYSA-N 4-hydroxy-2-quinolone Chemical compound C1=CC=C2C(O)=CC(=O)NC2=C1 HDHQZCHIXUUSMK-UHFFFAOYSA-N 0.000 description 1
- VCLUTORDCGANOB-UHFFFAOYSA-N 4-hydroxybutyl 3-[bis(2-hydroxyethyl)amino]propanoate Chemical compound OCCCCOC(=O)CCN(CCO)CCO VCLUTORDCGANOB-UHFFFAOYSA-N 0.000 description 1
- AOMKYCIOFLWFBM-UHFFFAOYSA-M 4-methylbenzenesulfonate;[4-[(2-methylpropan-2-yl)oxy]phenyl]-diphenylsulfanium Chemical compound CC1=CC=C(S([O-])(=O)=O)C=C1.C1=CC(OC(C)(C)C)=CC=C1[S+](C=1C=CC=CC=1)C1=CC=CC=C1 AOMKYCIOFLWFBM-UHFFFAOYSA-M 0.000 description 1
- RAXMFFZNRKLKLH-UHFFFAOYSA-M 4-methylbenzenesulfonate;[4-[(2-methylpropan-2-yl)oxy]phenyl]-phenyliodanium Chemical compound CC1=CC=C(S([O-])(=O)=O)C=C1.C1=CC(OC(C)(C)C)=CC=C1[I+]C1=CC=CC=C1 RAXMFFZNRKLKLH-UHFFFAOYSA-M 0.000 description 1
- MNYVHIDJVUQXKZ-UHFFFAOYSA-M 4-methylbenzenesulfonate;trimethylsulfanium Chemical compound C[S+](C)C.CC1=CC=C(S([O-])(=O)=O)C=C1 MNYVHIDJVUQXKZ-UHFFFAOYSA-M 0.000 description 1
- WJEQCFQCLZICPS-UHFFFAOYSA-N 4-morpholin-4-yloxan-2-one Chemical compound C1COC(=O)CC1N1CCOCC1 WJEQCFQCLZICPS-UHFFFAOYSA-N 0.000 description 1
- TYMLOMAKGOJONV-UHFFFAOYSA-N 4-nitroaniline Chemical compound NC1=CC=C([N+]([O-])=O)C=C1 TYMLOMAKGOJONV-UHFFFAOYSA-N 0.000 description 1
- ATCGHKBXRIOBDX-UHFFFAOYSA-N 4-nonan-5-ylpyridine Chemical compound CCCCC(CCCC)C1=CC=NC=C1 ATCGHKBXRIOBDX-UHFFFAOYSA-N 0.000 description 1
- WMYPMMDDCUOFEX-UHFFFAOYSA-N 4-piperidin-1-yloxolan-2-one Chemical compound C1OC(=O)CC1N1CCCCC1 WMYPMMDDCUOFEX-UHFFFAOYSA-N 0.000 description 1
- RGUKYNXWOWSRET-UHFFFAOYSA-N 4-pyrrolidin-1-ylpyridine Chemical compound C1CCCN1C1=CC=NC=C1 RGUKYNXWOWSRET-UHFFFAOYSA-N 0.000 description 1
- YSHMQTRICHYLGF-UHFFFAOYSA-N 4-tert-butylpyridine Chemical compound CC(C)(C)C1=CC=NC=C1 YSHMQTRICHYLGF-UHFFFAOYSA-N 0.000 description 1
- 125000006043 5-hexenyl group Chemical group 0.000 description 1
- TYOXIFXYEIILLY-UHFFFAOYSA-N 5-methyl-2-phenyl-1h-imidazole Chemical compound N1C(C)=CN=C1C1=CC=CC=C1 TYOXIFXYEIILLY-UHFFFAOYSA-N 0.000 description 1
- UYLYISCHTFVYHN-UHFFFAOYSA-N 7-oxabicyclo[2.2.1]heptane-3-carboxylic acid Chemical compound C1CC2C(C(=O)O)CC1O2 UYLYISCHTFVYHN-UHFFFAOYSA-N 0.000 description 1
- CYHOMWAPJJPNMW-UHFFFAOYSA-N 8-methyl-8-azabicyclo[3.2.1]octan-3-ol Chemical compound C1C(O)CC2CCC1N2C CYHOMWAPJJPNMW-UHFFFAOYSA-N 0.000 description 1
- 239000004925 Acrylic resin Substances 0.000 description 1
- 229920000178 Acrylic resin Polymers 0.000 description 1
- GFFGJBXGBJISGV-UHFFFAOYSA-N Adenine Chemical class NC1=NC=NC2=C1N=CN2 GFFGJBXGBJISGV-UHFFFAOYSA-N 0.000 description 1
- 229910018125 Al-Si Inorganic materials 0.000 description 1
- 229910018520 Al—Si Inorganic materials 0.000 description 1
- 239000004475 Arginine Substances 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 1
- WNADMDKXCVOZLW-UHFFFAOYSA-N C(C)O[Si](C1C2CC(C(C1)C2)C(=O)O)(OCC)OCC.C(C)O[Si](C2CC1CCC2C1)(OCC)OCC Chemical compound C(C)O[Si](C1C2CC(C(C1)C2)C(=O)O)(OCC)OCC.C(C)O[Si](C2CC1CCC2C1)(OCC)OCC WNADMDKXCVOZLW-UHFFFAOYSA-N 0.000 description 1
- HPFODLCEBDTPKR-UHFFFAOYSA-N C1(C(C=CC=C1)C)(C)S(=O)(=O)C(=[N+]=[N-])S(=O)(=O)C1(C(C=CC=C1)C)C Chemical compound C1(C(C=CC=C1)C)(C)S(=O)(=O)C(=[N+]=[N-])S(=O)(=O)C1(C(C=CC=C1)C)C HPFODLCEBDTPKR-UHFFFAOYSA-N 0.000 description 1
- WSFDZYFBPPCZOZ-UHFFFAOYSA-N C1(CCCCC1)OC(C(C)N1CCCCC1)=O Chemical compound C1(CCCCC1)OC(C(C)N1CCCCC1)=O WSFDZYFBPPCZOZ-UHFFFAOYSA-N 0.000 description 1
- XHRXGFQOLPTYGJ-UHFFFAOYSA-N CC1=CC=C(S([O-])(=O)=O)C=C1.O=C1CCCCC1[SH+]CC1CCCCC1 Chemical compound CC1=CC=C(S([O-])(=O)=O)C=C1.O=C1CCCCC1[SH+]CC1CCCCC1 XHRXGFQOLPTYGJ-UHFFFAOYSA-N 0.000 description 1
- XCMLOOCHPWZTDA-UHFFFAOYSA-N CO[Si](C1C2CC(C(C1)C2)C(=O)O)(OC)OC.CO[Si](C2CC1CCC2C1)(OC)OC Chemical compound CO[Si](C1C2CC(C(C1)C2)C(=O)O)(OC)OC.CO[Si](C2CC1CCC2C1)(OC)OC XCMLOOCHPWZTDA-UHFFFAOYSA-N 0.000 description 1
- NQORLFQPPUEQSA-UHFFFAOYSA-N CS(=O)(=O)O.ON1C(=O)C2C3C=CC(C2C1=O)C3 Chemical class CS(=O)(=O)O.ON1C(=O)C2C3C=CC(C2C1=O)C3 NQORLFQPPUEQSA-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 1
- PMPVIKIVABFJJI-UHFFFAOYSA-N Cyclobutane Chemical compound C1CCC1 PMPVIKIVABFJJI-UHFFFAOYSA-N 0.000 description 1
- LVZWSLJZHVFIQJ-UHFFFAOYSA-N Cyclopropane Chemical compound C1CC1 LVZWSLJZHVFIQJ-UHFFFAOYSA-N 0.000 description 1
- MHZGKXUYDGKKIU-UHFFFAOYSA-N Decylamine Chemical compound CCCCCCCCCCN MHZGKXUYDGKKIU-UHFFFAOYSA-N 0.000 description 1
- XBPCUCUWBYBCDP-UHFFFAOYSA-N Dicyclohexylamine Chemical compound C1CCCCC1NC1CCCCC1 XBPCUCUWBYBCDP-UHFFFAOYSA-N 0.000 description 1
- 229920001174 Diethylhydroxylamine Polymers 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- XXRCUYVCPSWGCC-UHFFFAOYSA-N Ethyl pyruvate Chemical compound CCOC(=O)C(C)=O XXRCUYVCPSWGCC-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 1
- SAHAYCLKIFYFLP-UHFFFAOYSA-N FC(S(=O)(=O)O)(F)F.ON1C(=O)C2C3C=CC(C2C1=O)C3 Chemical class FC(S(=O)(=O)O)(F)F.ON1C(=O)C2C3C=CC(C2C1=O)C3 SAHAYCLKIFYFLP-UHFFFAOYSA-N 0.000 description 1
- WHUUTDBJXJRKMK-UHFFFAOYSA-N Glutamic acid Natural products OC(=O)C(N)CCC(O)=O WHUUTDBJXJRKMK-UHFFFAOYSA-N 0.000 description 1
- DKEXFJVMVGETOO-LURJTMIESA-N Gly-Leu Chemical compound CC(C)C[C@@H](C(O)=O)NC(=O)CN DKEXFJVMVGETOO-LURJTMIESA-N 0.000 description 1
- 239000004471 Glycine Substances 0.000 description 1
- NYHBQMYGNKIUIF-UUOKFMHZSA-N Guanosine Chemical class C1=NC=2C(=O)NC(N)=NC=2N1[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O NYHBQMYGNKIUIF-UUOKFMHZSA-N 0.000 description 1
- WJYIASZWHGOTOU-UHFFFAOYSA-N Heptylamine Chemical compound CCCCCCCN WJYIASZWHGOTOU-UHFFFAOYSA-N 0.000 description 1
- 101000692259 Homo sapiens Phosphoprotein associated with glycosphingolipid-enriched microdomains 1 Proteins 0.000 description 1
- HCUARRIEZVDMPT-UHFFFAOYSA-N Indole-2-carboxylic acid Chemical compound C1=CC=C2NC(C(=O)O)=CC2=C1 HCUARRIEZVDMPT-UHFFFAOYSA-N 0.000 description 1
- QNAYBMKLOCPYGJ-REOHCLBHSA-N L-alanine Chemical compound C[C@H](N)C(O)=O QNAYBMKLOCPYGJ-REOHCLBHSA-N 0.000 description 1
- ODKSFYDXXFIFQN-BYPYZUCNSA-P L-argininium(2+) Chemical compound NC(=[NH2+])NCCC[C@H]([NH3+])C(O)=O ODKSFYDXXFIFQN-BYPYZUCNSA-P 0.000 description 1
- CKLJMWTZIZZHCS-REOHCLBHSA-N L-aspartic acid Chemical compound OC(=O)[C@@H](N)CC(O)=O CKLJMWTZIZZHCS-REOHCLBHSA-N 0.000 description 1
- WHUUTDBJXJRKMK-VKHMYHEASA-N L-glutamic acid Chemical compound OC(=O)[C@@H](N)CCC(O)=O WHUUTDBJXJRKMK-VKHMYHEASA-N 0.000 description 1
- HNDVDQJCIGZPNO-YFKPBYRVSA-N L-histidine Chemical compound OC(=O)[C@@H](N)CC1=CN=CN1 HNDVDQJCIGZPNO-YFKPBYRVSA-N 0.000 description 1
- AGPKZVBTJJNPAG-WHFBIAKZSA-N L-isoleucine Chemical compound CC[C@H](C)[C@H](N)C(O)=O AGPKZVBTJJNPAG-WHFBIAKZSA-N 0.000 description 1
- ROHFNLRQFUQHCH-YFKPBYRVSA-N L-leucine Chemical compound CC(C)C[C@H](N)C(O)=O ROHFNLRQFUQHCH-YFKPBYRVSA-N 0.000 description 1
- FFEARJCKVFRZRR-BYPYZUCNSA-N L-methionine Chemical compound CSCC[C@H](N)C(O)=O FFEARJCKVFRZRR-BYPYZUCNSA-N 0.000 description 1
- COLNVLDHVKWLRT-QMMMGPOBSA-N L-phenylalanine Chemical compound OC(=O)[C@@H](N)CC1=CC=CC=C1 COLNVLDHVKWLRT-QMMMGPOBSA-N 0.000 description 1
- AYFVYJQAPQTCCC-GBXIJSLDSA-N L-threonine Chemical compound C[C@@H](O)[C@H](N)C(O)=O AYFVYJQAPQTCCC-GBXIJSLDSA-N 0.000 description 1
- ROHFNLRQFUQHCH-UHFFFAOYSA-N Leucine Natural products CC(C)CC(N)C(O)=O ROHFNLRQFUQHCH-UHFFFAOYSA-N 0.000 description 1
- PEEHTFAAVSWFBL-UHFFFAOYSA-N Maleimide Chemical compound O=C1NC(=O)C=C1 PEEHTFAAVSWFBL-UHFFFAOYSA-N 0.000 description 1
- AFVFQIVMOAPDHO-UHFFFAOYSA-M Methanesulfonate Chemical compound CS([O-])(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-M 0.000 description 1
- BAVYZALUXZFZLV-UHFFFAOYSA-O Methylammonium ion Chemical compound [NH3+]C BAVYZALUXZFZLV-UHFFFAOYSA-O 0.000 description 1
- VKEQBMCRQDSRET-UHFFFAOYSA-N Methylone Chemical compound CNC(C)C(=O)C1=CC=C2OCOC2=C1 VKEQBMCRQDSRET-UHFFFAOYSA-N 0.000 description 1
- DHRYUWTZILQCSH-UHFFFAOYSA-N N#CCC1C=CC(OC)=CC1=NOS(=O)(=O)C1=CC=C(C)C=C1 Chemical compound N#CCC1C=CC(OC)=CC1=NOS(=O)(=O)C1=CC=C(C)C=C1 DHRYUWTZILQCSH-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
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
- VIWZVFVJPXTXPA-UHFFFAOYSA-N N-(2-Carboxymethyl)-morpholine Chemical compound OC(=O)CN1CCOCC1 VIWZVFVJPXTXPA-UHFFFAOYSA-N 0.000 description 1
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 1
- AFCARXCZXQIEQB-UHFFFAOYSA-N N-[3-oxo-3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propyl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C(CCNC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)N1CC2=C(CC1)NN=N2 AFCARXCZXQIEQB-UHFFFAOYSA-N 0.000 description 1
- AKNUHUCEWALCOI-UHFFFAOYSA-N N-ethyldiethanolamine Chemical compound OCCN(CC)CCO AKNUHUCEWALCOI-UHFFFAOYSA-N 0.000 description 1
- AHVYPIQETPWLSZ-UHFFFAOYSA-N N-methyl-pyrrolidine Natural products CN1CC=CC1 AHVYPIQETPWLSZ-UHFFFAOYSA-N 0.000 description 1
- OHLUUHNLEMFGTQ-UHFFFAOYSA-N N-methylacetamide Chemical compound CNC(C)=O OHLUUHNLEMFGTQ-UHFFFAOYSA-N 0.000 description 1
- SWPCFSVOBPPHBL-UHFFFAOYSA-N NCCC(=O)OC1CCOC1=O Chemical compound NCCC(=O)OC1CCOC1=O SWPCFSVOBPPHBL-UHFFFAOYSA-N 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- QFOOBAOUMBWKCO-UHFFFAOYSA-N OC(COC(C1C(C2)C=CC2C1)=O)(C(F)(F)F)C(F)(F)F Chemical compound OC(COC(C1C(C2)C=CC2C1)=O)(C(F)(F)F)C(F)(F)F QFOOBAOUMBWKCO-UHFFFAOYSA-N 0.000 description 1
- ZYRQKIUVOUMBNB-UHFFFAOYSA-N OC(COC(C1C(CC2)CC2C1)=O)(C(F)(F)F)C(F)(F)F Chemical compound OC(COC(C1C(CC2)CC2C1)=O)(C(F)(F)F)C(F)(F)F ZYRQKIUVOUMBNB-UHFFFAOYSA-N 0.000 description 1
- OGUFPWUWNQSMRT-UHFFFAOYSA-N OCCC(C(=O)OCC#N)CN Chemical compound OCCC(C(=O)OCC#N)CN OGUFPWUWNQSMRT-UHFFFAOYSA-N 0.000 description 1
- ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 description 1
- 102100026066 Phosphoprotein associated with glycosphingolipid-enriched microdomains 1 Human genes 0.000 description 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 1
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 description 1
- 101000987219 Sus scrofa Pregnancy-associated glycoprotein 1 Proteins 0.000 description 1
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 description 1
- AYFVYJQAPQTCCC-UHFFFAOYSA-N Threonine Natural products CC(O)C(N)C(O)=O AYFVYJQAPQTCCC-UHFFFAOYSA-N 0.000 description 1
- 239000004473 Threonine Substances 0.000 description 1
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 1
- SLINHMUFWFWBMU-UHFFFAOYSA-N Triisopropanolamine Chemical compound CC(O)CN(CC(C)O)CC(C)O SLINHMUFWFWBMU-UHFFFAOYSA-N 0.000 description 1
- ISAKRJDGNUQOIC-UHFFFAOYSA-N Uracil Chemical class O=C1C=CNC(=O)N1 ISAKRJDGNUQOIC-UHFFFAOYSA-N 0.000 description 1
- DRTQHJPVMGBUCF-XVFCMESISA-N Uridine Chemical class O[C@@H]1[C@H](O)[C@@H](CO)O[C@H]1N1C(=O)NC(=O)C=C1 DRTQHJPVMGBUCF-XVFCMESISA-N 0.000 description 1
- 229910008938 W—Si Inorganic materials 0.000 description 1
- XPZWRXYDVYKMSN-UHFFFAOYSA-N [(e)-diazo(2-methylbutan-2-ylsulfonyl)methyl]sulfonylcyclohexane Chemical compound CCC(C)(C)S(=O)(=O)C(=[N+]=[N-])S(=O)(=O)C1CCCCC1 XPZWRXYDVYKMSN-UHFFFAOYSA-N 0.000 description 1
- YPPVLYIFEAESGO-UHFFFAOYSA-N [2,3-bis(methylsulfonyloxy)phenyl] methanesulfonate Chemical compound CS(=O)(=O)OC1=CC=CC(OS(C)(=O)=O)=C1OS(C)(=O)=O YPPVLYIFEAESGO-UHFFFAOYSA-N 0.000 description 1
- DCYQPMGIYRPCBA-UHFFFAOYSA-N [2,3-bis(trifluoromethylsulfonyloxy)phenyl] trifluoromethanesulfonate Chemical compound FC(F)(F)S(=O)(=O)OC1=CC=CC(OS(=O)(=O)C(F)(F)F)=C1OS(=O)(=O)C(F)(F)F DCYQPMGIYRPCBA-UHFFFAOYSA-N 0.000 description 1
- OIHCCWXZFYNOJS-UHFFFAOYSA-N [2,3-bis-(4-methylphenyl)sulfonyloxyphenyl] 4-methylbenzenesulfonate Chemical compound C1=CC(C)=CC=C1S(=O)(=O)OC1=CC=CC(OS(=O)(=O)C=2C=CC(C)=CC=2)=C1OS(=O)(=O)C1=CC=C(C)C=C1 OIHCCWXZFYNOJS-UHFFFAOYSA-N 0.000 description 1
- ZUSQIFOBBBRZIR-UHFFFAOYSA-N [4-(2,2,2-trifluoroacetyl)phenyl] acetate Chemical compound CC(=O)OC1=CC=C(C(=O)C(F)(F)F)C=C1 ZUSQIFOBBBRZIR-UHFFFAOYSA-N 0.000 description 1
- VORHQBCYQIHPFJ-UHFFFAOYSA-N [4-(2,2,2-trifluoroacetyl)phenyl] methanesulfonate Chemical compound CS(=O)(=O)OC1=CC=C(C(=O)C(F)(F)F)C=C1 VORHQBCYQIHPFJ-UHFFFAOYSA-N 0.000 description 1
- HKKMPPDCCCBZHM-UHFFFAOYSA-M [4-[(2-methylpropan-2-yl)oxy]phenyl]-diphenylsulfanium;trifluoromethanesulfonate Chemical compound [O-]S(=O)(=O)C(F)(F)F.C1=CC(OC(C)(C)C)=CC=C1[S+](C=1C=CC=CC=1)C1=CC=CC=C1 HKKMPPDCCCBZHM-UHFFFAOYSA-M 0.000 description 1
- ISFXMNADAJKIEG-UHFFFAOYSA-M [4-[(2-methylpropan-2-yl)oxy]phenyl]-phenyliodanium;trifluoromethanesulfonate Chemical compound [O-]S(=O)(=O)C(F)(F)F.C1=CC(OC(C)(C)C)=CC=C1[I+]C1=CC=CC=C1 ISFXMNADAJKIEG-UHFFFAOYSA-M 0.000 description 1
- CTCKOPRVSJSTDI-UHFFFAOYSA-N [N]=S(=O)=O Chemical compound [N]=S(=O)=O CTCKOPRVSJSTDI-UHFFFAOYSA-N 0.000 description 1
- YZKPMQYQDNZVOA-UHFFFAOYSA-N [[(4-chlorophenyl)-cyanomethylidene]amino] benzenesulfonate Chemical compound C1=CC(Cl)=CC=C1C(C#N)=NOS(=O)(=O)C1=CC=CC=C1 YZKPMQYQDNZVOA-UHFFFAOYSA-N 0.000 description 1
- DUEWIMJKSQKVJB-UHFFFAOYSA-N [[5-[cyano(phenyl)methylidene]thiophen-2-ylidene]amino] 4-methylbenzenesulfonate Chemical compound C1=CC(C)=CC=C1S(=O)(=O)ON=C(S1)C=CC1=C(C#N)C1=CC=CC=C1 DUEWIMJKSQKVJB-UHFFFAOYSA-N 0.000 description 1
- WJQLVLRNUROQSL-UHFFFAOYSA-N [[5-[cyano(phenyl)methylidene]thiophen-2-ylidene]amino] octane-1-sulfonate Chemical compound C1=CC(=NOS(=O)(=O)CCCCCCCC)SC1=C(C#N)C1=CC=CC=C1 WJQLVLRNUROQSL-UHFFFAOYSA-N 0.000 description 1
- GLCCGSHEKBXUGH-UHFFFAOYSA-N [[5-[cyano-(2-methylphenyl)methylidene]thiophen-2-ylidene]amino] 4-methylbenzenesulfonate Chemical compound C1=CC(C)=CC=C1S(=O)(=O)ON=C(S1)C=CC1=C(C#N)C1=CC=CC=C1C GLCCGSHEKBXUGH-UHFFFAOYSA-N 0.000 description 1
- LMBCUZJGJVCPSD-UHFFFAOYSA-N [[cyano(phenyl)methylidene]amino] 4-methylbenzenesulfonate Chemical compound C1=CC(C)=CC=C1S(=O)(=O)ON=C(C#N)C1=CC=CC=C1 LMBCUZJGJVCPSD-UHFFFAOYSA-N 0.000 description 1
- SOLHUHOMYHSYTJ-UHFFFAOYSA-N [[cyano(phenyl)methylidene]amino] 4-nitro-2-(trifluoromethyl)benzenesulfonate Chemical compound FC(F)(F)C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)ON=C(C#N)C1=CC=CC=C1 SOLHUHOMYHSYTJ-UHFFFAOYSA-N 0.000 description 1
- BEYLCDIPKBCBGC-UHFFFAOYSA-N [[cyano(phenyl)methylidene]amino] 4-nitrobenzenesulfonate Chemical compound C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)ON=C(C#N)C1=CC=CC=C1 BEYLCDIPKBCBGC-UHFFFAOYSA-N 0.000 description 1
- KOMVIYNHRYVHAN-UHFFFAOYSA-N [[cyano(thiophen-2-yl)methylidene]amino] benzenesulfonate Chemical compound C=1C=CC=CC=1S(=O)(=O)ON=C(C#N)C1=CC=CS1 KOMVIYNHRYVHAN-UHFFFAOYSA-N 0.000 description 1
- UHNRALZVSXNUTL-UHFFFAOYSA-N [[cyano-(2,4-dichlorophenyl)methylidene]amino] benzenesulfonate Chemical compound ClC1=CC(Cl)=CC=C1C(C#N)=NOS(=O)(=O)C1=CC=CC=C1 UHNRALZVSXNUTL-UHFFFAOYSA-N 0.000 description 1
- YLEGKVDNSYZTCN-UHFFFAOYSA-N [[cyano-(2,6-dichlorophenyl)methylidene]amino] benzenesulfonate Chemical compound ClC1=CC=CC(Cl)=C1C(C#N)=NOS(=O)(=O)C1=CC=CC=C1 YLEGKVDNSYZTCN-UHFFFAOYSA-N 0.000 description 1
- LOVKRNMQTUTWQJ-UHFFFAOYSA-N [[cyano-(4-methoxyphenyl)methylidene]amino] 2-chlorobenzenesulfonate Chemical compound C1=CC(OC)=CC=C1C(C#N)=NOS(=O)(=O)C1=CC=CC=C1Cl LOVKRNMQTUTWQJ-UHFFFAOYSA-N 0.000 description 1
- OGYIZEXHMFOOOY-UHFFFAOYSA-N [[cyano-(4-methoxyphenyl)methylidene]amino] benzenesulfonate Chemical compound C1=CC(OC)=CC=C1C(C#N)=NOS(=O)(=O)C1=CC=CC=C1 OGYIZEXHMFOOOY-UHFFFAOYSA-N 0.000 description 1
- QFKJMDYQKVPGNM-UHFFFAOYSA-N [benzenesulfonyl(diazo)methyl]sulfonylbenzene Chemical compound C=1C=CC=CC=1S(=O)(=O)C(=[N+]=[N-])S(=O)(=O)C1=CC=CC=C1 QFKJMDYQKVPGNM-UHFFFAOYSA-N 0.000 description 1
- DUJLILQBTCLTDQ-UHFFFAOYSA-N [cyclopentylsulfonyl(diazo)methyl]sulfonylcyclopentane Chemical compound C1CCCC1S(=O)(=O)C(=[N+]=[N-])S(=O)(=O)C1CCCC1 DUJLILQBTCLTDQ-UHFFFAOYSA-N 0.000 description 1
- JIUIIWVYHWSFAZ-UHFFFAOYSA-N ac1o0v2m Chemical class O.O.O.O.O JIUIIWVYHWSFAZ-UHFFFAOYSA-N 0.000 description 1
- 125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 150000001251 acridines Chemical class 0.000 description 1
- 125000002252 acyl group Chemical group 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 150000003835 adenosine derivatives Chemical class 0.000 description 1
- 230000032683 aging Effects 0.000 description 1
- 235000004279 alanine Nutrition 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 229940045714 alkyl sulfonate alkylating agent Drugs 0.000 description 1
- 150000008052 alkyl sulfonates Chemical class 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- 150000003862 amino acid derivatives Chemical class 0.000 description 1
- 229960004050 aminobenzoic acid Drugs 0.000 description 1
- 150000003927 aminopyridines Chemical class 0.000 description 1
- 235000019270 ammonium chloride Nutrition 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 150000001448 anilines Chemical class 0.000 description 1
- 125000005577 anthracene group Chemical group 0.000 description 1
- 229940054051 antipsychotic indole derivative Drugs 0.000 description 1
- 229940027998 antiseptic and disinfectant acridine derivative Drugs 0.000 description 1
- 229940027991 antiseptic and disinfectant quinoline derivative Drugs 0.000 description 1
- ODKSFYDXXFIFQN-UHFFFAOYSA-N arginine Natural products OC(=O)C(N)CCCNC(N)=N ODKSFYDXXFIFQN-UHFFFAOYSA-N 0.000 description 1
- 235000009697 arginine Nutrition 0.000 description 1
- 125000005228 aryl sulfonate group Chemical group 0.000 description 1
- 235000003704 aspartic acid Nutrition 0.000 description 1
- JXLHNMVSKXFWAO-UHFFFAOYSA-N azane;7-fluoro-2,1,3-benzoxadiazole-4-sulfonic acid Chemical compound N.OS(=O)(=O)C1=CC=C(F)C2=NON=C12 JXLHNMVSKXFWAO-UHFFFAOYSA-N 0.000 description 1
- 229920005601 base polymer Polymers 0.000 description 1
- 150000007514 bases Chemical class 0.000 description 1
- SRSXLGNVWSONIS-UHFFFAOYSA-M benzenesulfonate Chemical compound [O-]S(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-M 0.000 description 1
- 229940077388 benzenesulfonate Drugs 0.000 description 1
- AAUAWZGILBBROA-UHFFFAOYSA-N benzenesulfonic acid;1-hydroxypiperidine-2,6-dione Chemical class ON1C(=O)CCCC1=O.OS(=O)(=O)C1=CC=CC=C1 AAUAWZGILBBROA-UHFFFAOYSA-N 0.000 description 1
- LIOXIFDNVZABQS-UHFFFAOYSA-N benzenesulfonic acid;1-hydroxypyrrolidine-2,5-dione Chemical compound ON1C(=O)CCC1=O.OS(=O)(=O)C1=CC=CC=C1 LIOXIFDNVZABQS-UHFFFAOYSA-N 0.000 description 1
- CXJVMJWCNFOERL-UHFFFAOYSA-N benzenesulfonylsulfonylbenzene Chemical compound C=1C=CC=CC=1S(=O)(=O)S(=O)(=O)C1=CC=CC=C1 CXJVMJWCNFOERL-UHFFFAOYSA-N 0.000 description 1
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 description 1
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
- OQFSQFPPLPISGP-UHFFFAOYSA-N beta-carboxyaspartic acid Natural products OC(=O)C(N)C(C(O)=O)C(O)=O OQFSQFPPLPISGP-UHFFFAOYSA-N 0.000 description 1
- HXYXVFUUHSZSNV-UHFFFAOYSA-N bicyclo[2.2.1]hept-2-ene-5-carbonyl chloride Chemical compound C1C2C(C(=O)Cl)CC1C=C2 HXYXVFUUHSZSNV-UHFFFAOYSA-N 0.000 description 1
- 230000005540 biological transmission Effects 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 125000006267 biphenyl group Chemical group 0.000 description 1
- VDPDRYUUTXEEIE-UHFFFAOYSA-N bis-methylsulphonyl methane Natural products CS(=O)(=O)CS(C)(=O)=O VDPDRYUUTXEEIE-UHFFFAOYSA-N 0.000 description 1
- WTXDNMDDFAESOT-UHFFFAOYSA-M bis[4-[(2-methylpropan-2-yl)oxy]phenyl]-phenylsulfanium;4-methylbenzenesulfonate Chemical compound CC1=CC=C(S([O-])(=O)=O)C=C1.C1=CC(OC(C)(C)C)=CC=C1[S+](C=1C=CC(OC(C)(C)C)=CC=1)C1=CC=CC=C1 WTXDNMDDFAESOT-UHFFFAOYSA-M 0.000 description 1
- SSCOHVUVCBYNFB-UHFFFAOYSA-M bis[4-[(2-methylpropan-2-yl)oxy]phenyl]-phenylsulfanium;trifluoromethanesulfonate Chemical compound [O-]S(=O)(=O)C(F)(F)F.C1=CC(OC(C)(C)C)=CC=C1[S+](C=1C=CC(OC(C)(C)C)=CC=1)C1=CC=CC=C1 SSCOHVUVCBYNFB-UHFFFAOYSA-M 0.000 description 1
- 229940006460 bromide ion Drugs 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 1
- QDHFHIQKOVNCNC-UHFFFAOYSA-M butane-1-sulfonate Chemical compound CCCCS([O-])(=O)=O QDHFHIQKOVNCNC-UHFFFAOYSA-M 0.000 description 1
- QPXMRCTYZIAUQD-UHFFFAOYSA-M butane-1-sulfonate;triphenylsulfanium Chemical compound CCCCS([O-])(=O)=O.C1=CC=CC=C1[S+](C=1C=CC=CC=1)C1=CC=CC=C1 QPXMRCTYZIAUQD-UHFFFAOYSA-M 0.000 description 1
- 125000004369 butenyl group Chemical group C(=CCC)* 0.000 description 1
- 125000004106 butoxy group Chemical group [*]OC([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- 125000006226 butoxyethyl group Chemical group 0.000 description 1
- BBONZYOYSUGYFA-UHFFFAOYSA-N butyl 3-morpholin-4-ylpropanoate Chemical compound CCCCOC(=O)CCN1CCOCC1 BBONZYOYSUGYFA-UHFFFAOYSA-N 0.000 description 1
- 229940043232 butyl acetate Drugs 0.000 description 1
- 125000000609 carbazolyl group Chemical class C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 description 1
- 229910002091 carbon monoxide Inorganic materials 0.000 description 1
- 239000003610 charcoal Substances 0.000 description 1
- KYKAJFCTULSVSH-UHFFFAOYSA-N chloro(fluoro)methane Chemical compound F[C]Cl KYKAJFCTULSVSH-UHFFFAOYSA-N 0.000 description 1
- 125000000068 chlorophenyl group Chemical group 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
- 125000000259 cinnolinyl group Chemical class N1=NC(=CC2=CC=CC=C12)* 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000003431 cross linking reagent Substances 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- BSRJKQXCXYEDEW-UHFFFAOYSA-N cyanomethyl 3-(diethylamino)propanoate Chemical compound CCN(CC)CCC(=O)OCC#N BSRJKQXCXYEDEW-UHFFFAOYSA-N 0.000 description 1
- MFHARVKJGFXNJI-UHFFFAOYSA-N cyanomethyl 3-[bis(2-methoxyethyl)amino]propanoate Chemical compound COCCN(CCOC)CCC(=O)OCC#N MFHARVKJGFXNJI-UHFFFAOYSA-N 0.000 description 1
- UMNKQXGKQDYOBN-UHFFFAOYSA-N cyanomethyl 3-[bis[2-(methoxymethoxy)ethyl]amino]propanoate Chemical compound COCOCCN(CCOCOC)CCC(=O)OCC#N UMNKQXGKQDYOBN-UHFFFAOYSA-N 0.000 description 1
- MSSSIIZBSGQTLN-UHFFFAOYSA-N cyanomethyl 3-piperidin-1-ylpropanoate Chemical compound N#CCOC(=O)CCN1CCCCC1 MSSSIIZBSGQTLN-UHFFFAOYSA-N 0.000 description 1
- SFFDITYNQBKGDV-UHFFFAOYSA-N cyanomethyl propanoate Chemical compound CCC(=O)OCC#N SFFDITYNQBKGDV-UHFFFAOYSA-N 0.000 description 1
- 125000000596 cyclohexenyl group Chemical group C1(=CCCCC1)* 0.000 description 1
- 125000002933 cyclohexyloxy group Chemical group C1(CCCCC1)O* 0.000 description 1
- ODOYKCYDOVBTAR-UHFFFAOYSA-N cyclohexylsulfonylsulfonylcyclohexane Chemical compound C1CCCCC1S(=O)(=O)S(=O)(=O)C1CCCCC1 ODOYKCYDOVBTAR-UHFFFAOYSA-N 0.000 description 1
- NISGSNTVMOOSJQ-UHFFFAOYSA-N cyclopentanamine Chemical compound NC1CCCC1 NISGSNTVMOOSJQ-UHFFFAOYSA-N 0.000 description 1
- 125000001887 cyclopentyloxy group Chemical group C1(CCCC1)O* 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- OVLXQLQBOCAFDH-UHFFFAOYSA-M dicyclohexyl(phenyl)sulfanium;4-methylbenzenesulfonate Chemical compound CC1=CC=C(S([O-])(=O)=O)C=C1.C1CCCCC1[S+](C=1C=CC=CC=1)C1CCCCC1 OVLXQLQBOCAFDH-UHFFFAOYSA-M 0.000 description 1
- NSXRYFKEEKGLHO-UHFFFAOYSA-M dicyclohexyl(phenyl)sulfanium;trifluoromethanesulfonate Chemical compound [O-]S(=O)(=O)C(F)(F)F.C1CCCCC1[S+](C=1C=CC=CC=1)C1CCCCC1 NSXRYFKEEKGLHO-UHFFFAOYSA-M 0.000 description 1
- FVCOIAYSJZGECG-UHFFFAOYSA-N diethylhydroxylamine Chemical compound CCN(O)CC FVCOIAYSJZGECG-UHFFFAOYSA-N 0.000 description 1
- 229940043279 diisopropylamine Drugs 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- CYQUIWZGOBANMJ-UHFFFAOYSA-M dimethyl(phenyl)sulfanium;trifluoromethanesulfonate Chemical compound [O-]S(=O)(=O)C(F)(F)F.C[S+](C)C1=CC=CC=C1 CYQUIWZGOBANMJ-UHFFFAOYSA-M 0.000 description 1
- XXBDWLFCJWSEKW-UHFFFAOYSA-N dimethylbenzylamine Chemical compound CN(C)CC1=CC=CC=C1 XXBDWLFCJWSEKW-UHFFFAOYSA-N 0.000 description 1
- JGUQDUKBUKFFRO-CIIODKQPSA-N dimethylglyoxime Chemical compound O/N=C(/C)\C(\C)=N\O JGUQDUKBUKFFRO-CIIODKQPSA-N 0.000 description 1
- LAWOZCWGWDVVSG-UHFFFAOYSA-N dioctylamine Chemical compound CCCCCCCCNCCCCCCCC LAWOZCWGWDVVSG-UHFFFAOYSA-N 0.000 description 1
- UMIKAXKFQJWKCV-UHFFFAOYSA-M diphenyliodanium;4-methylbenzenesulfonate Chemical compound CC1=CC=C(S([O-])(=O)=O)C=C1.C=1C=CC=CC=1[I+]C1=CC=CC=C1 UMIKAXKFQJWKCV-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
- WEHWNAOGRSTTBQ-UHFFFAOYSA-N dipropylamine Chemical compound CCCNCCC WEHWNAOGRSTTBQ-UHFFFAOYSA-N 0.000 description 1
- JRBPAEWTRLWTQC-UHFFFAOYSA-N dodecylamine Chemical compound CCCCCCCCCCCCN JRBPAEWTRLWTQC-UHFFFAOYSA-N 0.000 description 1
- XBRDBODLCHKXHI-UHFFFAOYSA-N epolamine Chemical compound OCCN1CCCC1 XBRDBODLCHKXHI-UHFFFAOYSA-N 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 125000006232 ethoxy propyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000005448 ethoxyethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])C([H])([H])* 0.000 description 1
- 125000005745 ethoxymethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])* 0.000 description 1
- CWAFVXWRGIEBPL-UHFFFAOYSA-N ethoxysilane Chemical compound CCO[SiH3] CWAFVXWRGIEBPL-UHFFFAOYSA-N 0.000 description 1
- IIIBKVMTKMLDFJ-UHFFFAOYSA-N ethyl 2-pyrrolidin-1-ylacetate Chemical compound CCOC(=O)CN1CCCC1 IIIBKVMTKMLDFJ-UHFFFAOYSA-N 0.000 description 1
- RVBSTKZJNIUIAT-UHFFFAOYSA-N ethyl 3-[bis(2-acetyloxyethyl)amino]propanoate Chemical compound CCOC(=O)CCN(CCOC(C)=O)CCOC(C)=O RVBSTKZJNIUIAT-UHFFFAOYSA-N 0.000 description 1
- WFTLLQNZESXWLJ-UHFFFAOYSA-N ethyl 3-[bis(2-hydroxyethyl)amino]propanoate Chemical compound CCOC(=O)CCN(CCO)CCO WFTLLQNZESXWLJ-UHFFFAOYSA-N 0.000 description 1
- WRBIQTVRBWJCQT-UHFFFAOYSA-N ethyl 3-morpholin-4-ylpropanoate Chemical compound CCOC(=O)CCN1CCOCC1 WRBIQTVRBWJCQT-UHFFFAOYSA-N 0.000 description 1
- 229940116333 ethyl lactate Drugs 0.000 description 1
- 229940117360 ethyl pyruvate Drugs 0.000 description 1
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 1
- 150000002221 fluorine Chemical class 0.000 description 1
- 125000003709 fluoroalkyl group Chemical group 0.000 description 1
- 125000001207 fluorophenyl group Chemical group 0.000 description 1
- 150000002244 furazanes Chemical class 0.000 description 1
- 125000002541 furyl group Chemical group 0.000 description 1
- JVZRCNQLWOELDU-UHFFFAOYSA-N gamma-Phenylpyridine Natural products C1=CC=CC=C1C1=CC=NC=C1 JVZRCNQLWOELDU-UHFFFAOYSA-N 0.000 description 1
- 235000013922 glutamic acid Nutrition 0.000 description 1
- 239000004220 glutamic acid Substances 0.000 description 1
- 108010050848 glycylleucine Proteins 0.000 description 1
- UYTPUPDQBNUYGX-UHFFFAOYSA-N guanine Chemical class O=C1NC(N)=NC2=C1N=CN2 UYTPUPDQBNUYGX-UHFFFAOYSA-N 0.000 description 1
- 125000005842 heteroatom Chemical group 0.000 description 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-M hexanoate Chemical compound CCCCCC([O-])=O FUZZWVXGSFPDMH-UHFFFAOYSA-M 0.000 description 1
- 125000006038 hexenyl group Chemical group 0.000 description 1
- 125000003707 hexyloxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])O* 0.000 description 1
- HNDVDQJCIGZPNO-UHFFFAOYSA-N histidine Natural products OC(=O)C(N)CC1=CN=CN1 HNDVDQJCIGZPNO-UHFFFAOYSA-N 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 150000002460 imidazoles Chemical class 0.000 description 1
- 150000002461 imidazolidines Chemical class 0.000 description 1
- 150000002462 imidazolines Chemical class 0.000 description 1
- 125000002883 imidazolyl group Chemical group 0.000 description 1
- 150000002466 imines Chemical group 0.000 description 1
- 125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 description 1
- 150000002475 indoles Chemical class 0.000 description 1
- 125000003387 indolinyl group Chemical class N1(CCC2=CC=CC=C12)* 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 230000010354 integration Effects 0.000 description 1
- 229940079865 intestinal antiinfectives imidazole derivative Drugs 0.000 description 1
- 229910052741 iridium Inorganic materials 0.000 description 1
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 description 1
- 125000002510 isobutoxy group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])O* 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
- 150000002518 isoindoles Chemical class 0.000 description 1
- AGPKZVBTJJNPAG-UHFFFAOYSA-N isoleucine Natural products CCC(C)C(N)C(O)=O AGPKZVBTJJNPAG-UHFFFAOYSA-N 0.000 description 1
- 229960000310 isoleucine Drugs 0.000 description 1
- JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 description 1
- 150000002537 isoquinolines Chemical class 0.000 description 1
- ZLTPDFXIESTBQG-UHFFFAOYSA-N isothiazole Chemical compound C=1C=NSC=1 ZLTPDFXIESTBQG-UHFFFAOYSA-N 0.000 description 1
- CTAPFRYPJLPFDF-UHFFFAOYSA-N isoxazole Chemical compound C=1C=NOC=1 CTAPFRYPJLPFDF-UHFFFAOYSA-N 0.000 description 1
- 230000031700 light absorption Effects 0.000 description 1
- CCERQOYLJJULMD-UHFFFAOYSA-M magnesium;carbanide;chloride Chemical compound [CH3-].[Mg+2].[Cl-] CCERQOYLJJULMD-UHFFFAOYSA-M 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- RTWNYYOXLSILQN-UHFFFAOYSA-N methanediamine Chemical compound NCN RTWNYYOXLSILQN-UHFFFAOYSA-N 0.000 description 1
- 229930182817 methionine Natural products 0.000 description 1
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 description 1
- ARYZCSRUUPFYMY-UHFFFAOYSA-N methoxysilane Chemical compound CO[SiH3] ARYZCSRUUPFYMY-UHFFFAOYSA-N 0.000 description 1
- SUHOWDMWVWQBPK-UHFFFAOYSA-N methyl 2-[4-(2,2,2-trifluoroacetyl)phenoxy]acetate Chemical compound COC(=O)COC1=CC=C(C(=O)C(F)(F)F)C=C1 SUHOWDMWVWQBPK-UHFFFAOYSA-N 0.000 description 1
- REGWVSTWPUXKJS-UHFFFAOYSA-N methyl 2-piperidin-1-ylacetate Chemical compound COC(=O)CN1CCCCC1 REGWVSTWPUXKJS-UHFFFAOYSA-N 0.000 description 1
- BDBUYOTTWWGIDJ-UHFFFAOYSA-N methyl 2-thiomorpholin-4-ylacetate Chemical compound COC(=O)CN1CCSCC1 BDBUYOTTWWGIDJ-UHFFFAOYSA-N 0.000 description 1
- NKYGUYBTYSZAAJ-UHFFFAOYSA-N methyl 3-[2-cyanoethyl(2-hydroxyethyl)amino]propanoate Chemical compound COC(=O)CCN(CCO)CCC#N NKYGUYBTYSZAAJ-UHFFFAOYSA-N 0.000 description 1
- ODOCEKVZTLEAAP-UHFFFAOYSA-N methyl 3-[2-hydroxyethyl-(3-methoxy-3-oxopropyl)amino]propanoate Chemical compound COC(=O)CCN(CCO)CCC(=O)OC ODOCEKVZTLEAAP-UHFFFAOYSA-N 0.000 description 1
- WYPIYJCVKPAZOQ-UHFFFAOYSA-N methyl 3-[bis(2-acetyloxyethyl)amino]propanoate Chemical compound COC(=O)CCN(CCOC(C)=O)CCOC(C)=O WYPIYJCVKPAZOQ-UHFFFAOYSA-N 0.000 description 1
- PDLCQBOPNILNFH-UHFFFAOYSA-N methyl 3-[bis(2-hydroxyethyl)amino]propanoate Chemical compound COC(=O)CCN(CCO)CCO PDLCQBOPNILNFH-UHFFFAOYSA-N 0.000 description 1
- BHTBQFHOJIBPKY-UHFFFAOYSA-N methyl 3-[bis(2-methoxyethyl)amino]propanoate Chemical compound COCCN(CCOC)CCC(=O)OC BHTBQFHOJIBPKY-UHFFFAOYSA-N 0.000 description 1
- YDNHCHDMPIHHGH-UHFFFAOYSA-N methyl 3-[bis(3-methoxy-3-oxopropyl)amino]propanoate Chemical compound COC(=O)CCN(CCC(=O)OC)CCC(=O)OC YDNHCHDMPIHHGH-UHFFFAOYSA-N 0.000 description 1
- BKQUFNJLMGRJHL-UHFFFAOYSA-N methyl 3-[cyanomethyl(2-hydroxyethyl)amino]propanoate Chemical compound COC(=O)CCN(CCO)CC#N BKQUFNJLMGRJHL-UHFFFAOYSA-N 0.000 description 1
- ZCOLLGOATUZZNL-UHFFFAOYSA-N methyl 3-[cyanomethyl(2-methoxyethyl)amino]propanoate Chemical compound COCCN(CC#N)CCC(=O)OC ZCOLLGOATUZZNL-UHFFFAOYSA-N 0.000 description 1
- BDJSOPWXYLFTNW-UHFFFAOYSA-N methyl 3-methoxypropanoate Chemical compound COCCC(=O)OC BDJSOPWXYLFTNW-UHFFFAOYSA-N 0.000 description 1
- YMSLLIGKMYXCPK-UHFFFAOYSA-N methyl 3-morpholin-4-ylpropanoate Chemical compound COC(=O)CCN1CCOCC1 YMSLLIGKMYXCPK-UHFFFAOYSA-N 0.000 description 1
- ANAJGIRVGQSWEN-UHFFFAOYSA-N methyl 3-piperidin-1-ylpropanoate Chemical compound COC(=O)CCN1CCCCC1 ANAJGIRVGQSWEN-UHFFFAOYSA-N 0.000 description 1
- JHYKOXJKJHTKTE-UHFFFAOYSA-N methyl 3-pyrrolidin-1-ylpropanoate Chemical compound COC(=O)CCN1CCCC1 JHYKOXJKJHTKTE-UHFFFAOYSA-N 0.000 description 1
- RMAZRAQKPTXZNL-UHFFFAOYSA-N methyl bicyclo[2.2.1]hept-2-ene-5-carboxylate Chemical compound C1C2C(C(=O)OC)CC1C=C2 RMAZRAQKPTXZNL-UHFFFAOYSA-N 0.000 description 1
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- 150000002780 morpholines Chemical class 0.000 description 1
- DILRJUIACXKSQE-UHFFFAOYSA-N n',n'-dimethylethane-1,2-diamine Chemical compound CN(C)CCN DILRJUIACXKSQE-UHFFFAOYSA-N 0.000 description 1
- VGIVLIHKENZQHQ-UHFFFAOYSA-N n,n,n',n'-tetramethylmethanediamine Chemical compound CN(C)CN(C)C VGIVLIHKENZQHQ-UHFFFAOYSA-N 0.000 description 1
- SRLHDBRENZFCIN-UHFFFAOYSA-N n,n-di(butan-2-yl)butan-2-amine Chemical compound CCC(C)N(C(C)CC)C(C)CC SRLHDBRENZFCIN-UHFFFAOYSA-N 0.000 description 1
- ZQJAONQEOXOVNR-UHFFFAOYSA-N n,n-di(nonyl)nonan-1-amine Chemical compound CCCCCCCCCN(CCCCCCCCC)CCCCCCCCC ZQJAONQEOXOVNR-UHFFFAOYSA-N 0.000 description 1
- FRQONEWDWWHIPM-UHFFFAOYSA-N n,n-dicyclohexylcyclohexanamine Chemical compound C1CCCCC1N(C1CCCCC1)C1CCCCC1 FRQONEWDWWHIPM-UHFFFAOYSA-N 0.000 description 1
- NILJCGYQNXKIRL-UHFFFAOYSA-N n,n-dicyclopentylcyclopentanamine Chemical compound C1CCCC1N(C1CCCC1)C1CCCC1 NILJCGYQNXKIRL-UHFFFAOYSA-N 0.000 description 1
- CLZGJKHEVKJLLS-UHFFFAOYSA-N n,n-diheptylheptan-1-amine Chemical compound CCCCCCCN(CCCCCCC)CCCCCCC CLZGJKHEVKJLLS-UHFFFAOYSA-N 0.000 description 1
- DIAIBWNEUYXDNL-UHFFFAOYSA-N n,n-dihexylhexan-1-amine Chemical compound CCCCCCN(CCCCCC)CCCCCC DIAIBWNEUYXDNL-UHFFFAOYSA-N 0.000 description 1
- DAZXVJBJRMWXJP-UHFFFAOYSA-N n,n-dimethylethylamine Chemical compound CCN(C)C DAZXVJBJRMWXJP-UHFFFAOYSA-N 0.000 description 1
- PSHKMPUSSFXUIA-UHFFFAOYSA-N n,n-dimethylpyridin-2-amine Chemical compound CN(C)C1=CC=CC=N1 PSHKMPUSSFXUIA-UHFFFAOYSA-N 0.000 description 1
- XTAZYLNFDRKIHJ-UHFFFAOYSA-N n,n-dioctyloctan-1-amine Chemical compound CCCCCCCCN(CCCCCCCC)CCCCCCCC XTAZYLNFDRKIHJ-UHFFFAOYSA-N 0.000 description 1
- OOHAUGDGCWURIT-UHFFFAOYSA-N n,n-dipentylpentan-1-amine Chemical compound CCCCCN(CCCCC)CCCCC OOHAUGDGCWURIT-UHFFFAOYSA-N 0.000 description 1
- QVPWDPDVDVVXIB-UHFFFAOYSA-N n-(2-hydroxyethyl)pyridine-4-carboxamide Chemical compound OCCNC(=O)C1=CC=NC=C1 QVPWDPDVDVVXIB-UHFFFAOYSA-N 0.000 description 1
- PDYUCXOQBNSGKN-UHFFFAOYSA-N n-[2,2,2-trifluoro-1-(2,4,6-trimethylphenyl)ethylidene]hydroxylamine Chemical compound CC1=CC(C)=C(C(=NO)C(F)(F)F)C(C)=C1 PDYUCXOQBNSGKN-UHFFFAOYSA-N 0.000 description 1
- OBYVIBDTOCAXSN-UHFFFAOYSA-N n-butan-2-ylbutan-2-amine Chemical compound CCC(C)NC(C)CC OBYVIBDTOCAXSN-UHFFFAOYSA-N 0.000 description 1
- 125000006606 n-butoxy group Chemical group 0.000 description 1
- PZYDAVFRVJXFHS-UHFFFAOYSA-N n-cyclohexyl-2-pyrrolidone Chemical compound O=C1CCCN1C1CCCCC1 PZYDAVFRVJXFHS-UHFFFAOYSA-N 0.000 description 1
- GMTCPFCMAHMEMT-UHFFFAOYSA-N n-decyldecan-1-amine Chemical compound CCCCCCCCCCNCCCCCCCCCC GMTCPFCMAHMEMT-UHFFFAOYSA-N 0.000 description 1
- MJCJUDJQDGGKOX-UHFFFAOYSA-N n-dodecyldodecan-1-amine Chemical compound CCCCCCCCCCCCNCCCCCCCCCCCC MJCJUDJQDGGKOX-UHFFFAOYSA-N 0.000 description 1
- SMBYUOXUISCLCF-UHFFFAOYSA-N n-ethyl-n-methylpropan-1-amine Chemical compound CCCN(C)CC SMBYUOXUISCLCF-UHFFFAOYSA-N 0.000 description 1
- NJWMENBYMFZACG-UHFFFAOYSA-N n-heptylheptan-1-amine Chemical compound CCCCCCCNCCCCCCC NJWMENBYMFZACG-UHFFFAOYSA-N 0.000 description 1
- NQYKSVOHDVVDOR-UHFFFAOYSA-N n-hexadecylhexadecan-1-amine Chemical compound CCCCCCCCCCCCCCCCNCCCCCCCCCCCCCCCC NQYKSVOHDVVDOR-UHFFFAOYSA-N 0.000 description 1
- PXSXRABJBXYMFT-UHFFFAOYSA-N n-hexylhexan-1-amine Chemical compound CCCCCCNCCCCCC PXSXRABJBXYMFT-UHFFFAOYSA-N 0.000 description 1
- DYFFAVRFJWYYQO-UHFFFAOYSA-N n-methyl-n-phenylaniline Chemical compound C=1C=CC=CC=1N(C)C1=CC=CC=C1 DYFFAVRFJWYYQO-UHFFFAOYSA-N 0.000 description 1
- MFHKEJIIHDNPQE-UHFFFAOYSA-N n-nonylnonan-1-amine Chemical compound CCCCCCCCCNCCCCCCCCC MFHKEJIIHDNPQE-UHFFFAOYSA-N 0.000 description 1
- JACMPVXHEARCBO-UHFFFAOYSA-N n-pentylpentan-1-amine Chemical compound CCCCCNCCCCC JACMPVXHEARCBO-UHFFFAOYSA-N 0.000 description 1
- NTNWKDHZTDQSST-UHFFFAOYSA-N naphthalene-1,2-diamine Chemical compound C1=CC=CC2=C(N)C(N)=CC=C21 NTNWKDHZTDQSST-UHFFFAOYSA-N 0.000 description 1
- 229960003512 nicotinic acid Drugs 0.000 description 1
- 235000001968 nicotinic acid Nutrition 0.000 description 1
- 239000011664 nicotinic acid Substances 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 150000002825 nitriles Chemical group 0.000 description 1
- 125000005246 nonafluorobutyl group Chemical group FC(F)(F)C(F)(F)C(F)(F)C(F)(F)* 0.000 description 1
- FJDUDHYHRVPMJZ-UHFFFAOYSA-N nonan-1-amine Chemical compound CCCCCCCCCN FJDUDHYHRVPMJZ-UHFFFAOYSA-N 0.000 description 1
- IOQPZZOEVPZRBK-UHFFFAOYSA-N octan-1-amine Chemical compound CCCCCCCCN IOQPZZOEVPZRBK-UHFFFAOYSA-N 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- 150000007978 oxazole derivatives Chemical class 0.000 description 1
- 150000002923 oximes Chemical class 0.000 description 1
- LJGSUFJICGWYLT-UHFFFAOYSA-N oxiran-2-ylmethyl 3-piperidin-1-ylpropanoate Chemical compound C1OC1COC(=O)CCN1CCCCC1 LJGSUFJICGWYLT-UHFFFAOYSA-N 0.000 description 1
- XWRUCQQZEVLMAN-UHFFFAOYSA-N oxolan-2-ylmethyl 3-(2-hydroxyethylamino)propanoate Chemical compound OCCNCCC(=O)OCC1CCCO1 XWRUCQQZEVLMAN-UHFFFAOYSA-N 0.000 description 1
- LCJLCKSXBYGANE-UHFFFAOYSA-N oxolan-2-ylmethyl 3-[bis(2-acetyloxyethyl)amino]propanoate Chemical compound CC(=O)OCCN(CCOC(C)=O)CCC(=O)OCC1CCCO1 LCJLCKSXBYGANE-UHFFFAOYSA-N 0.000 description 1
- 125000000636 p-nitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)[N+]([O-])=O 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 238000000059 patterning Methods 0.000 description 1
- 125000004817 pentamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 description 1
- 125000004115 pentoxy group Chemical group [*]OC([H])([H])C([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- 229940100684 pentylamine Drugs 0.000 description 1
- 229940083254 peripheral vasodilators imidazoline derivative Drugs 0.000 description 1
- 229940083251 peripheral vasodilators purine derivative Drugs 0.000 description 1
- 150000005053 phenanthridines Chemical class 0.000 description 1
- 150000002988 phenazines Chemical class 0.000 description 1
- COLNVLDHVKWLRT-UHFFFAOYSA-N phenylalanine Natural products OC(=O)C(N)CC1=CC=CC=C1 COLNVLDHVKWLRT-UHFFFAOYSA-N 0.000 description 1
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 1
- 125000000286 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
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 description 1
- LFSXCDWNBUNEEM-UHFFFAOYSA-N phthalazine Chemical class C1=NN=CC2=CC=CC=C21 LFSXCDWNBUNEEM-UHFFFAOYSA-N 0.000 description 1
- XKJCHHZQLQNZHY-UHFFFAOYSA-N phthalimide Chemical compound C1=CC=C2C(=O)NC(=O)C2=C1 XKJCHHZQLQNZHY-UHFFFAOYSA-N 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 150000004885 piperazines Chemical class 0.000 description 1
- 150000003053 piperidines Chemical class 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 229910021420 polycrystalline silicon Inorganic materials 0.000 description 1
- 229920005591 polysilicon Polymers 0.000 description 1
- 239000011148 porous material Substances 0.000 description 1
- 125000001844 prenyl group Chemical group [H]C([*])([H])C([H])=C(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 238000002360 preparation method Methods 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
- 125000006233 propoxy propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])OC([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000006225 propoxyethyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])OC([H])([H])C([H])([H])* 0.000 description 1
- 125000005767 propoxymethyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])[#8]C([H])([H])* 0.000 description 1
- 125000004742 propyloxycarbonyl group Chemical group 0.000 description 1
- 125000001042 pteridinyl group Chemical class N1=C(N=CC2=NC=CN=C12)* 0.000 description 1
- 150000003212 purines Chemical class 0.000 description 1
- 150000003216 pyrazines Chemical class 0.000 description 1
- 150000003217 pyrazoles Chemical class 0.000 description 1
- 150000003218 pyrazolidines Chemical class 0.000 description 1
- 150000003219 pyrazolines Chemical class 0.000 description 1
- 125000001725 pyrenyl group Chemical group 0.000 description 1
- 150000004892 pyridazines Chemical class 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- DVECLMOWYVDJRM-UHFFFAOYSA-N pyridine-3-sulfonic acid Chemical compound OS(=O)(=O)C1=CC=CN=C1 DVECLMOWYVDJRM-UHFFFAOYSA-N 0.000 description 1
- 150000003222 pyridines Chemical class 0.000 description 1
- ZDYVRSLAEXCVBX-UHFFFAOYSA-N pyridinium p-toluenesulfonate Chemical compound C1=CC=[NH+]C=C1.CC1=CC=C(S([O-])(=O)=O)C=C1 ZDYVRSLAEXCVBX-UHFFFAOYSA-N 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 229940083082 pyrimidine derivative acting on arteriolar smooth muscle Drugs 0.000 description 1
- 150000003230 pyrimidines Chemical class 0.000 description 1
- 150000003233 pyrroles Chemical class 0.000 description 1
- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 description 1
- 150000003235 pyrrolidines Chemical class 0.000 description 1
- ZVJHJDDKYZXRJI-UHFFFAOYSA-N pyrroline Natural products C1CC=NC1 ZVJHJDDKYZXRJI-UHFFFAOYSA-N 0.000 description 1
- 150000003236 pyrrolines Chemical class 0.000 description 1
- QZZYYBQGTSGDPP-UHFFFAOYSA-N quinoline-3-carbonitrile Chemical compound C1=CC=CC2=CC(C#N)=CN=C21 QZZYYBQGTSGDPP-UHFFFAOYSA-N 0.000 description 1
- 150000003248 quinolines Chemical class 0.000 description 1
- 150000003252 quinoxalines Chemical class 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 230000001603 reducing effect Effects 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 239000011342 resin composition Substances 0.000 description 1
- BHRZNVHARXXAHW-UHFFFAOYSA-N sec-butylamine Chemical compound CCC(C)N BHRZNVHARXXAHW-UHFFFAOYSA-N 0.000 description 1
- 239000004065 semiconductor Substances 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 150000004756 silanes Chemical class 0.000 description 1
- SCPYDCQAZCOKTP-UHFFFAOYSA-N silanol Chemical compound [SiH3]O SCPYDCQAZCOKTP-UHFFFAOYSA-N 0.000 description 1
- 229920005573 silicon-containing polymer Polymers 0.000 description 1
- 229910000033 sodium borohydride Inorganic materials 0.000 description 1
- 239000012279 sodium borohydride Substances 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 229960002317 succinimide Drugs 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 229940066771 systemic antihistamines piperazine derivative Drugs 0.000 description 1
- 125000004213 tert-butoxy group Chemical group [H]C([H])([H])C(O*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- XULQYKHYHOXCJI-UHFFFAOYSA-N tert-butyl 2-piperidin-1-ylethyl carbonate Chemical compound CC(C)(C)OC(=O)OCCN1CCCCC1 XULQYKHYHOXCJI-UHFFFAOYSA-N 0.000 description 1
- WMOVHXAZOJBABW-UHFFFAOYSA-N tert-butyl acetate Chemical compound CC(=O)OC(C)(C)C WMOVHXAZOJBABW-UHFFFAOYSA-N 0.000 description 1
- JAELLLITIZHOGQ-UHFFFAOYSA-N tert-butyl propanoate Chemical compound CCC(=O)OC(C)(C)C JAELLLITIZHOGQ-UHFFFAOYSA-N 0.000 description 1
- YBRBMKDOPFTVDT-UHFFFAOYSA-N tert-butylamine Chemical compound CC(C)(C)N YBRBMKDOPFTVDT-UHFFFAOYSA-N 0.000 description 1
- 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- FAGUFWYHJQFNRV-UHFFFAOYSA-N tetraethylenepentamine Chemical compound NCCNCCNCCNCCN FAGUFWYHJQFNRV-UHFFFAOYSA-N 0.000 description 1
- 125000004192 tetrahydrofuran-2-yl group Chemical group [H]C1([H])OC([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000004187 tetrahydropyran-2-yl group Chemical group [H]C1([H])OC([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- LPSKDVINWQNWFE-UHFFFAOYSA-M tetrapropylazanium;hydroxide Chemical compound [OH-].CCC[N+](CCC)(CCC)CCC LPSKDVINWQNWFE-UHFFFAOYSA-M 0.000 description 1
- 229920001187 thermosetting polymer Polymers 0.000 description 1
- 150000007979 thiazole derivatives Chemical class 0.000 description 1
- 150000003568 thioethers Chemical class 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- 150000003624 transition metals Chemical class 0.000 description 1
- 238000002834 transmittance Methods 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
- ABVVEAHYODGCLZ-UHFFFAOYSA-N tridecan-1-amine Chemical compound CCCCCCCCCCCCCN ABVVEAHYODGCLZ-UHFFFAOYSA-N 0.000 description 1
- SWZDQOUHBYYPJD-UHFFFAOYSA-N tridodecylamine Chemical compound CCCCCCCCCCCCN(CCCCCCCCCCCC)CCCCCCCCCCCC SWZDQOUHBYYPJD-UHFFFAOYSA-N 0.000 description 1
- IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 description 1
- AANIRNIRVXARSN-UHFFFAOYSA-M trifluoromethanesulfonate;trimethylsulfanium Chemical compound C[S+](C)C.[O-]S(=O)(=O)C(F)(F)F AANIRNIRVXARSN-UHFFFAOYSA-M 0.000 description 1
- UPWIJTYOHJOEOX-UHFFFAOYSA-M trifluoromethanesulfonate;trinaphthalen-1-ylsulfanium Chemical compound [O-]S(=O)(=O)C(F)(F)F.C1=CC=C2C([S+](C=3C4=CC=CC=C4C=CC=3)C=3C4=CC=CC=C4C=CC=3)=CC=CC2=C1 UPWIJTYOHJOEOX-UHFFFAOYSA-M 0.000 description 1
- TUODWSVQODNTSU-UHFFFAOYSA-M trifluoromethanesulfonate;tris[4-[(2-methylpropan-2-yl)oxy]phenyl]sulfanium Chemical compound [O-]S(=O)(=O)C(F)(F)F.C1=CC(OC(C)(C)C)=CC=C1[S+](C=1C=CC(OC(C)(C)C)=CC=1)C1=CC=C(OC(C)(C)C)C=C1 TUODWSVQODNTSU-UHFFFAOYSA-M 0.000 description 1
- 125000001889 triflyl group Chemical group FC(F)(F)S(*)(=O)=O 0.000 description 1
- RKBCYCFRFCNLTO-UHFFFAOYSA-N triisopropylamine Chemical compound CC(C)N(C(C)C)C(C)C RKBCYCFRFCNLTO-UHFFFAOYSA-N 0.000 description 1
- 125000003258 trimethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])[*:1] 0.000 description 1
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- ODHXBMXNKOYIBV-UHFFFAOYSA-N triphenylamine Chemical compound C1=CC=CC=C1N(C=1C=CC=CC=1)C1=CC=CC=C1 ODHXBMXNKOYIBV-UHFFFAOYSA-N 0.000 description 1
- YFTHZRPMJXBUME-UHFFFAOYSA-N tripropylamine Chemical compound CCCN(CCC)CCC YFTHZRPMJXBUME-UHFFFAOYSA-N 0.000 description 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
- 229910052721 tungsten Inorganic materials 0.000 description 1
- WQJQOUPTWCFRMM-UHFFFAOYSA-N tungsten disilicide Chemical compound [Si]#[W]#[Si] WQJQOUPTWCFRMM-UHFFFAOYSA-N 0.000 description 1
- 229910021342 tungsten silicide Inorganic materials 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic System
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
- G03F7/075—Silicon-containing compounds
- G03F7/0757—Macromolecular compounds containing Si-O, Si-C or Si-N bonds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic System
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/18—Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic System
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/18—Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages
- C07F7/1804—Compounds having Si-O-C linkages
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
- G03F7/0046—Photosensitive materials with perfluoro compounds, e.g. for dry lithography
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
- G03F7/039—Macromolecular compounds which are photodegradable, e.g. positive electron resists
-
- 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
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S430/00—Radiation imagery chemistry: process, composition, or product thereof
- Y10S430/1053—Imaging affecting physical property or radiation sensitive material, or producing nonplanar or printing surface - process, composition, or product: radiation sensitive composition or product or process of making binder containing
- Y10S430/1055—Radiation sensitive composition or product or process of making
- Y10S430/106—Binder containing
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S430/00—Radiation imagery chemistry: process, composition, or product thereof
- Y10S430/1053—Imaging affecting physical property or radiation sensitive material, or producing nonplanar or printing surface - process, composition, or product: radiation sensitive composition or product or process of making binder containing
- Y10S430/1055—Radiation sensitive composition or product or process of making
- Y10S430/106—Binder containing
- Y10S430/108—Polyolefin or halogen containing
Description
[1]下記一般式(2)で表される含フッ素ケイ素化合物。
(式中、X1、X2、X3は水素原子、水酸基、ハロゲン原子、炭素数1〜6の直鎖状、分岐状又は環状のアルコキシ基、又は炭素数1〜20の直鎖状、分岐状、環状又は多環状骨格を持つ一価の有機基を表す。R1、R2はそれぞれ独立に水素原子、又は炭素数1〜20の直鎖状、分岐状、環状又は多環状骨格を持つ一価の有機基を表す。R1、R2は互いに結合してこれらが結合する炭素原子と共に環を形成してもよい。W1、W2はそれぞれ独立にメチレン基又は酸素原子を表す。R6は水素原子、メチル基、フッ素原子又はトリフルオロメチル基を表す。pは0又は1、qは1を表す。)
[2]下記一般式(2a)で表される繰り返し単位を有することを特徴とする含フッ素シリコーン樹脂。
(式中、X1a、X2a、X3aのうち少なくとも一つは酸素原子を表し、残りは水素原子、水酸基、ハロゲン原子、炭素数1〜20の直鎖状、分岐状、環状又は多環状骨格を持つ一価の有機基、又は炭素数1〜6の直鎖状、分岐状又は環状のアルコキシ基を表す。R 1、R2はそれぞれ独立に水素原子、又は炭素数1〜20の直鎖状、分岐状、環状又は多環状骨格を持つ一価の有機基を表す。R1、R2は互いに結合してこれらが結合する炭素原子と共に環を形成してもよい。W1、W2はそれぞれ独立にメチレン基又は酸素原子を表す。R6は水素原子、メチル基、フッ素原子又はトリフルオロメチル基を表す。pは0又は1、qは1を表す。)
[3](A)[2]記載のシリコーン樹脂、
(B)酸発生剤、
(C)有機溶剤
を含有してなるレジスト組成物。
[4](1)[3]記載のレジスト組成物を基板上に塗布する工程と、
(2)次いで加熱処理後、フォトマスクを介して波長300nm以下の高エネルギー線もしくは電子線で露光する工程と、
(3)必要に応じて加熱処理した後、現像液を用いて現像する工程と
を含むことを特徴とするパターン形成方法。
(式中、X1、X2、X3は水素原子、水酸基、ハロゲン原子、炭素数1〜6の直鎖状、分岐状又は環状のアルコキシ基、又は炭素数1〜20の直鎖状、分岐状、環状又は多環状骨格を持つ一価の有機基を表す。Yは二価の有機基を表す。R1、R2はそれぞれ独立に水素原子、又は炭素数1〜20の直鎖状、分岐状、環状又は多環状骨格を持つ一価の有機基を表す。R1、R2は互いに結合してこれらが結合する炭素原子と共に環を形成してもよい。)
これらの二価の有機基のうち、脂環を含有するものが特に好ましい。含まれる脂環としては、シクロペンタン、シクロヘキサン、[2.2.1]ヘプタン(ノルボルナン)、ビシクロ[2.2.2]オクタン、テトラシクロ[4.4.0.12,5.17,10]ドデカン(テトラシクロドデカン)が挙げられ、このうち、[2.2.1]ヘプタン又はテトラシクロ[4.4.0.12,5.17,10]ドデカンを有するものが特に好ましい。
更に、[2.2.1]ヘプタン又はテトラシクロ[4.4.0.12,5.17,10]ドデカンを有するもののうち、下記一般式で表される二価の有機基が特に好ましい。
(式中、W1、W2はそれぞれ独立にメチレン基又は酸素原子を表す。R6は水素原子、メチル基、フッ素原子又はトリフルオロメチル基を表す。p、qはそれぞれ独立に1又は0を表す。なお、本式は、
の二つのいずれか又は両方を代表して表す。)
下記一般式
(R1、R2は上記の通り。Y’は炭素−炭素二重結合を有し、この炭素−炭素二重結合にSiH基の水素原子が付加することによってYの二価の有機基が形成される一価の有機基を示す。)
好ましくは下記式(ii)
(R1、R2、R6、W1、W2、p、qは上記の通り。)
の化合物と、H−SiX1X2X3(X1、X2、X3は上記の通り)とのヒドロシリル化反応により得ることができる。この場合、式(i)、(ii)の化合物、即ち不飽和結合、特に好ましい二重結合を有する化合物は、本発明者らが先に出願した特願2006−022319号に詳しく述べられている方法等により製造することができる。ヒドロシリル化反応は通常、白金、パラジウム、イリジウム等の遷移金属触媒の存在下、反応基質を加熱することにより行う。反応は無溶媒で行うが、反応基質が固体である場合等には、n−ヘキサン、n−ヘプタン、n−オクタン、ベンゼン、トルエン、キシレン等の炭化水素類、アセトン、メチルエチルケトン等のケトン類、ジエチルエーテル、ジ−n−ブチルエーテル、テトラヒドロフラン、1,4−ジオキサン等のエーテル類等から選択した1種又は2種以上の溶媒を補助的に用いることもできる。
(式中、X1a、X2a、X3aのうち少なくとも一つは酸素原子を表し、残りは水素原子、水酸基、ハロゲン原子、炭素数1〜20の直鎖状、分岐状、環状又は多環状骨格を持つ一価の有機基、又は炭素数1〜6の直鎖状、分岐状又は環状のアルコキシ基を表す。Yは二価の有機基を表す。R1、R2はそれぞれ独立に水素原子、又は炭素数1〜20の直鎖状、分岐状、環状又は多環状骨格を持つ一価の有機基を表す。W1、W2はそれぞれ独立にメチレン基又は酸素原子を表す。R1、R2は互いに結合してこれらが結合する炭素原子と共に環を形成してもよい。R6は水素原子、メチル基、フッ素原子又はトリフルオロメチル基を表す。p、qはそれぞれ独立に0又は1を表す。)
(式中、R3は官能基として無保護又は酸分解性保護基で保護されたカルボキシル基を持ち、そのカルボキシル基の他にハロゲン原子、酸素又はイオウ原子を含んでいてもよい炭素数3〜20の直鎖状、分岐状もしくは環状又は多環状骨格を持った有機基を表す。R4は官能基としてラクトン環又はカルボン酸無水物を有し、そのラクトン環又はカルボン酸無水物の他にハロゲン原子、酸素又はイオウ原子を含んでいてもよい炭素数4〜16の有機基を表す。R5は官能基としてヒドロキシ基を持ち、ハロゲン原子、酸素原子又はイオウ原子を含んでいてもよい炭素数3〜20の直鎖状、分岐状もしくは環状又は多環状骨格を持った有機基を表す。X4、X5、X6、X7、X8、X9、X10、X11、X12は水素原子、水酸基、ハロゲン原子、炭素数1〜6の直鎖状、分岐状又は環状のアルコキシ基、又は炭素数1〜20の直鎖状、分岐状、環状又は多環状骨格を持つ一価の有機基を表す。)
(式中、R3、R4、R5は前記と同様である。X4a、X5a、X6aのうち少なくとも一つは酸素原子を表し、残りは水素原子、水酸基、ハロゲン原子、炭素数1〜20の直鎖状、分岐状、環状又は多環状骨格を持つ一価の有機基、又は炭素数1〜6の直鎖状、分岐状又は環状のアルコキシ基を表す。X7a、X8a、X9aのうち少なくとも一つは酸素原子を表し、残りは水素原子、水酸基、ハロゲン原子、炭素数1〜20の直鎖状、分岐状、環状又は多環状骨格を持つ一価の有機基、又は炭素数1〜6の直鎖状、分岐状又は環状のアルコキシ基を表す。X10a、X11a、X12aのうち少なくとも一つは酸素原子を表し、残りは水素原子、水酸基、ハロゲン原子、炭素数1〜20の直鎖状、分岐状、環状又は多環状骨格を持つ一価の有機基、又は炭素数1〜6の直鎖状、分岐状又は環状のアルコキシ基を表す。)
(式中、R3aは水素原子、メチル基又はトリフルオロメチル基を表し、R3bは水素原子又は酸不安定基を表し、rは0又は1を表す。X4、X5、X6は前記と同様である。)
(式中、R5a、R5bは炭素数1〜8のアルキル基又はパーフルオロアルキル基を表し、互いに結合してこれらが結合する炭素原子と共に環を形成してもよい。R5c、R5dは炭素数1〜8のアルキル基又はパーフルオロアルキル基を表し、互いに結合してこれらが結合する炭素原子と共に環を形成してもよい。R5e、R5fは炭素数1〜8のアルキル基又はパーフルオロアルキル基を表し、互いに結合してこれらが結合する炭素原子と共に環を形成してもよい。tは0又は1を表す。X10、X11、X12は前記と同様である。)
(式中、X13、X14、X15、X16、X17、X18、X19、X20、X21は水素原子、水酸基、ハロゲン原子、炭素数1〜6の直鎖状、分岐状又は環状のアルコキシ基を表す。R7、R8a、R8bは炭素数1〜20の直鎖状、分岐状、環状又は多環状骨格を持つアルキル基又はパーフルオロアルキル基を表す。)
(式中、R7、R8a、R8bは前記と同様である。X13a、X14a、X15a、X16aのうち少なくとも一つは酸素原子を表し、残りは水素原子、水酸基、ハロゲン原子、炭素数1〜20の直鎖状、分岐状、環状又は多環状骨格を持つ一価の有機基、又は炭素数1〜6の直鎖状、分岐状又は環状のアルコキシ基を表す。X17a、X18a、X19aのうち少なくとも一つは酸素原子を表し、残りは水素原子、水酸基、ハロゲン原子、炭素数1〜20の直鎖状、分岐状、環状又は多環状骨格を持つ一価の有機基、又は炭素数1〜6の直鎖状、分岐状又は環状のアルコキシ基を表す。X20a、X21aのうち少なくとも一つは酸素原子を表し、残りは水素原子、水酸基、ハロゲン原子、炭素数1〜20の直鎖状、分岐状、環状又は多環状骨格を持つ一価の有機基、又は炭素数1〜6の直鎖状、分岐状又は環状のアルコキシ基を表す。)
(A)ベース樹脂として上記シリコーン樹脂、
(B)酸発生剤、
(C)有機溶剤
を含有する。
更に、(D)含窒素有機化合物
を含有するものが好ましい。
i.下記一般式(P1a−1)、(P1a−2)又は(P1b)のオニウム塩、
ii.下記一般式(P2)のジアゾメタン誘導体、
iii.下記一般式(P3)のグリオキシム誘導体、
iv.下記一般式(P4)のビススルホン誘導体、
v.下記一般式(P5)のN−ヒドロキシイミド化合物のスルホン酸エステル、
vi.β−ケトスルホン酸誘導体、
vii.ジスルホン誘導体、
viii.ニトロベンジルスルホネート誘導体、
ix.スルホン酸エステル誘導体、
x.オキシムスルホン酸エステル
等が挙げられる。
(式中、R101a、R101b、R101cはそれぞれ炭素数1〜12の直鎖状、分岐状又は環状のアルキル基、アルケニル基、オキソアルキル基、炭素数6〜20のアリール基又は炭素数7〜12のアラルキル基又はアリールオキソアルキル基を示し、これらの基の水素原子の一部又は全部がアルコキシ基等によって置換されていてもよい。また、R101bとR101cとは環を形成してもよく、環を形成する場合には、R101b、R101cはそれぞれ炭素数1〜6のアルキレン基を表す。K-は非求核性対向イオンを表す。)
(式中、R102a、R102bはそれぞれ炭素数1〜8の直鎖状、分岐状又は環状のアルキル基を表す。R103は炭素数1〜10の直鎖状、分岐状又は環状のアルキレン基を表す。R104a、R104bはそれぞれ炭素数3〜7の2−オキソアルキル基を表す。K-は非求核性対向イオンを表す。)
(式中、R107、R108、R109は炭素数1〜12の直鎖状、分岐状又は環状のアルキル基又はハロゲン化アルキル基、炭素数6〜20のアリール基又はハロゲン化アリール基、又は炭素数7〜12のアラルキル基を表す。R108、R109は互いに結合して環状構造を形成してもよく、環状構造を形成する場合、R108、R109はそれぞれ炭素数1〜6の直鎖状、分岐状のアルキレン基を表す。)
(式中、R110は炭素数6〜10のアリーレン基、炭素数1〜6のアルキレン基又は炭素数2〜6のアルケニレン基を示し、これらの基の水素原子の一部又は全部は更に炭素数1〜4の直鎖状又は分岐状のアルキル基又はアルコキシ基、ニトロ基、アセチル基又はフェニル基で置換されていてもよい。R111は炭素数1〜8の直鎖状、分岐状又は置換のアルキル基、アルケニル基、アルコキシアルキル基、フェニル基又はナフチル基を示し、これらの基の水素原子の一部又は全部は更に炭素数1〜4のアルキル基又はアルコキシ基、炭素数1〜4のアルキル基、アルコキシ基、ニトロ基又はアセチル基で置換されていてもよいフェニル基、炭素数3〜5のヘテロ芳香族基又は塩素原子、フッ素原子で置換されていてもよい。)
ジフェニルジスルホン、ジシクロヘキシルジスルホン等のジスルホン誘導体。
p−トルエンスルホン酸2,6−ジニトロベンジル、p−トルエンスルホン酸2,4−ジニトロベンジル等のニトロベンジルスルホネート誘導体。
1,2,3−トリス(メタンスルホニルオキシ)ベンゼン、1,2,3−トリス(トリフルオロメタンスルホニルオキシ)ベンゼン、1,2,3−トリス(p−トルエンスルホニルオキシ)ベンゼン等のスルホン酸エステル誘導体。
N(X)n(Y)3-n (D)−1
(上式中、nは1、2又は3である。側鎖Xは同一でも異なっていてもよく、下記一般式(X)−1〜(X)−3で表すことができる。側鎖Yは同一又は異種の、水素原子もしくは直鎖状、分岐状又は環状の炭素数1〜20のアルキル基を示し、エーテル基もしくはヒドロキシル基を含んでもよい。また、X同士が結合して環を形成してもよい。)
(上式中、R300、R302、R305は炭素数1〜4の直鎖状又は分岐状のアルキレン基であり、R301、R304は水素原子、又は炭素数1〜20の直鎖状、分岐状又は環状のアルキル基であり、ヒドロキシ基、エーテル基、エステル基、ラクトン環を1個あるいは複数個含んでいてもよい。R303は単結合、又は炭素数1〜4の直鎖状又は分岐状のアルキレン基であり、R306は炭素数1〜20の直鎖状、分岐状又は環状のアルキル基であり、ヒドロキシ基、エーテル基、エステル基、ラクトン環を1個あるいは複数個含んでいてもよい。)
(上式中、Xは前述の通り、R307は炭素数2〜20の直鎖状又は分岐状のアルキレン基であり、カルボニル基、エーテル基、エステル基又はスルフィドを1個あるいは複数個含んでいてもよい。)
(上式中、X、R307、nは前述の通り、R308、R309は同一又は異種の炭素数1〜4の直鎖状又は分岐状のアルキレン基である。)
(上式中、R310は炭素数2〜20の直鎖状、分岐状又は環状の極性官能基を有するアルキル基であり、極性官能基として水酸基、カルボニル基、エステル基、エーテル基、スルフィド基、カーボネート基、シアノ基、アセタール基を1個あるいは複数個含む。R311、R312、R313は水素原子、炭素数1〜10の直鎖状、分岐状又は環状のアルキル基、アリール基又はアラルキル基である。)
(上式中、R314は水素原子、炭素数1〜10の直鎖状、分岐状又は環状のアルキル基、アリール基又はアラルキル基である。R315は炭素数1〜20の直鎖状、分岐状又は環状の極性官能基を有するアルキル基であり、極性官能基としてエステル基、アセタール基、シアノ基を一つ以上含み、その他に水酸基、カルボニル基、エーテル基、スルフィド基、カーボネート基を一つ以上含んでいてもよい。)
(上式中、Aは窒素原子又は≡C−R322である。Bは窒素原子又は≡C−R323である。R316は炭素数2〜20の直鎖状、分岐状又は環状の極性官能基を有するアルキル基であり、極性官能基としては水酸基、カルボニル基、エステル基、エーテル基、スルフィド基、カーボネート基、シアノ基又はアセタール基を一つ以上含む。R317、R318、R319、R320は水素原子、炭素数1〜10の直鎖状、分岐状又は環状のアルキル基又はアリール基であるか、又はR317とR318、R319とR320はそれぞれ結合してベンゼン環、ナフタレン環あるいはピリジン環を形成してもよい。R321は水素原子、炭素数1〜10の直鎖状、分岐状又は環状のアルキル基又はアリール基である。R322、R323は水素原子、炭素数1〜10の直鎖状、分岐状又は環状のアルキル基又はアリール基である。R321とR323は結合してベンゼン環又はナフタレン環を形成してもよい。)
(上式中、R324は炭素数6〜20のアリール基又は炭素数4〜20のヘテロ芳香族基であって、水素原子の一部又は全部が、ハロゲン原子、炭素数1〜20の直鎖状、分岐状又は環状のアルキル基、炭素数6〜20のアリール基、炭素数7〜20のアラルキル基、炭素数1〜10のアルコキシ基、炭素数1〜10のアシルオキシ基、又は炭素数1〜10のアルキルチオ基で置換されていてもよい。R325はCO2R326、OR327又はシアノ基である。R326は一部のメチレン基が酸素原子で置換されていてもよい炭素数1〜10のアルキル基である。R327は一部のメチレン基が酸素原子で置換されていてもよい炭素数1〜10のアルキル基又はアシル基である。R328は単結合、メチレン基、エチレン基、硫黄原子又は−O(CH2CH2O)n−基である。n=0,1,2,3又は4である。R329は水素原子、メチル基、エチル基又はフェニル基である。Xは窒素原子又はCR330である。Yは窒素原子又はCR331である。Zは窒素原子又はCR332である。R330、R331、R332はそれぞれ独立に水素原子、メチル基又はフェニル基であるか、あるいはR330とR331又はR331とR332が結合して、炭素数6〜20の芳香環又は炭素数2〜20のヘテロ芳香環を形成してもよい。)
(上式中、R333は水素又は炭素数1〜10の直鎖状、分岐状又は環状のアルキル基である。R334及びR335はそれぞれ独立に、エーテル、カルボニル、エステル、アルコール、スルフィド、ニトリル、アミン、イミン、アミド等の極性官能基を一つ又は複数含んでいてもよい炭素数1〜20のアルキル基、炭素数6〜20のアリール基又は炭素数7〜20のアラルキル基であって、水素原子の一部がハロゲン原子で置換されていてもよい。R334とR335は互いに結合して、炭素数2〜20のヘテロ環又はヘテロ芳香環を形成してもよい。)
5−ノルボルネン−2−カルボン酸2−ヒドロキシ−3,3,3−トリフルオロ−2−トリフルオロメチルプロピル31.8g、塩化白金酸5%イソプロピルアルコール溶液1.0g、トリメトキシシラン25.0gの混合物を窒素雰囲気下、80℃で18時間加熱撹拌した。反応終了後、低沸成分を減圧留去し、続いて減圧蒸留を行い、目的物35.6gを得た(収率81%)。
5−ノルボルネン−2−カルボン酸2−ヒドロキシ−3,3,3−トリフルオロ−2−トリフルオロメチルプロピル31.8g、塩化白金酸5%イソプロピルアルコール溶液1.0g、トリエトキシシラン36.0gの混合物を窒素雰囲気下、80℃で18時間加熱撹拌した。反応終了後、低沸成分を減圧留去し、続いて減圧蒸留を行い、目的物40.6gを得た(収率84%)。
沸点:143℃/0.1kPa
GC−MS(EI):(m/z)+=119,163,395,436。主要異性体4種ともこれらのマスフラグメントを与えた。
19F−NMR(283MHz;トリフルオロ酢酸標準):δ=−76.5〜−76.1(6F)ppm。
5−ノルボルネン−2−カルボン酸2−ヒドロキシ−1,1−ジメチル−3,3,3−トリフルオロ−2−トリフルオロメチルプロピル34.6g、塩化白金酸5%イソプロピルアルコール溶液1.0g、トリメトキシシラン25.0gの混合物を窒素雰囲気下、80℃で24時間加熱撹拌した。反応終了後、低沸成分を減圧留去し、続いて減圧蒸留を行い、目的物36.5gを得た(収率78%)。
5−ノルボルネン−2−カルボン酸2−ヒドロキシ−1,1−ジメチル−3,3,3−トリフルオロ−2−トリフルオロメチルプロピル34.6g、塩化白金酸5%イソプロピルアルコール溶液1.0g、トリエトキシシラン36.0gの混合物を窒素雰囲気下、80℃で24時間加熱撹拌した。反応終了後、低沸成分を減圧留去し、続いて減圧蒸留を行い、目的物38.0gを得た(収率75%)。
沸点:128℃/0.1kPa
GC−MS(EI):(m/z)+=163,189,256,464。主要異性体4種ともこれらのマスフラグメントを与えた。
19F−NMR(283MHz;トリフルオロ酢酸標準):δ=−70.2〜−69.7(6F)ppm。
5−ノルボルネン−2−カルボン酸1−[1−ヒドロキシ−2,2,2−トリフルオロ−1−(トリフルオロメチル)エチル]シクロペンチル37.2g、塩化白金酸5%イソプロピルアルコール溶液1.0g、トリメトキシシラン25.0gの混合物を窒素雰囲気下、80℃で24時間加熱撹拌した。反応終了後、低沸成分を減圧留去し、続いて減圧蒸留を行い、目的物34.6gを得た(収率70%)。
5−ノルボルネン−2−カルボン酸1−[1−ヒドロキシ−2,2,2−トリフルオロ−1−(トリフルオロメチル)エチル]シクロペンチル37.2g、塩化白金酸5%イソプロピルアルコール溶液1.0g、トリエトキシシラン36.0gの混合物を窒素雰囲気下、80℃で24時間加熱撹拌した。反応終了後、低沸成分を減圧留去し、続いて減圧蒸留を行い、目的物40.2gを得た(収率75%)。
[Polymer−1の合成]
撹拌機、還流器、滴下ロート、温度計を備えた200mlの四つ口フラスコに酢酸0.2g、水20g、エタノール20gを仕込んで30℃に保ち、ここにシランモノマー2の9.6g(20mmol)、シランモノマー7の10.8g(30mmol)、シランモノマー10の16.4g(50mmol)をエタノール40gに溶解させた溶液を3時間かけて滴下した。引き続き30℃で20時間熟成させた後、この反応混合物をメチルイソブチルケトンで希釈し、有機層が中性となるまで水洗を繰り返した後、濃縮することによってオリゴマー28.9gを得た。
これをトルエン50gを用いて撹拌機、還流器、温度計を備えた100mlの三つ口フラスコに洗い込み、ここに水酸化カリウム56mgを加えて20時間加熱還流した。冷却後、反応液をメチルイソブチルケトンで希釈し、有機層が中性となるまで水洗を繰り返した後、濃縮することによってポリマー25.3gを得た。
NMRとGPC分析の結果、このものは下記式で示される重量平均分子量3,200のPolymer−1であることが確認できた。
表1に示したシランモノマーの組み合わせにより、Polymer−1の合成と同様の操作によりPolymer−2〜16を得た。表1に収量及び重量平均分子量(Mw、GPCポリスチレン換算)を併記する。
レジスト調製例
表2に示す組成で上記ポリマー(Polymer−1〜16)、酸発生剤(PAG1:トリフェニルスルホニウムノナフルオロ−n−ブタンスルホネート)、塩基性化合物をプロピレングリコールモノメチルエーテルアセテート(PGMEA)に溶解したのち、孔径0.2μmのフィルターを用いて濾過し、ポジ型レジスト膜形成用塗布液を調製した。次に、得られたレジスト溶液をスピンコーターで日産化学工業(株)製DUV−30J(55nm)を成膜したシリコンウエハーに塗布し、110℃で90秒間ベークして膜厚200nmのレジスト膜を形成した。これをArFエキシマレーザーステッパー((株)ニコン製、NSR−S305B、NA=0.68、σ=0.85)を用いて露光し、90℃で90秒間ベークを行った後、2.38質量%のテトラメチルアンモニウムヒドロキシド水溶液で60秒間現像を行って、ポジ型パターンを得た。
得られたレジストパターンを次のように評価した。
評価方法:
0.18μmのラインアンドスペースを1:1で解像する露光量を最適露光量(Eop、mJ/cm2)として、この露光量において分離しているラインアンドスペースの最小線幅を評価レジストの解像度とする。
使用したレジスト組成物及び得られた限界解像度を表2に示す。
下記モノマーの合成
[参考例1−1]1,1,1−トリフルオロ−2−トリフルオロメチル−3−メチル−2,3−ブタンジオールの合成
1Mメチルマグネシウムクロリドのテトラヒドロフラン溶液1,260mlをフラスコに収め、50℃以下にて、2−ヒドロキシ−3,3,3−トリフルオロ−2−トリフルオロメチルプロピオン酸メチル73.0gを滴下した。室温で1時間撹拌した後、塩化アンモニウム水溶液を加え、通常の後処理操作を行った。n−ヘプタンより再結晶を行い、目的物59.1gを得た(収率81%)。
融点:48℃(36℃開始 昇温1℃/分)
1H−NMR(600MHz in DMSO−d6):δ=1.31(6H,s),5.25(1H,s),7.43(1H,s)ppm
[参考例1−1]で得たアルコール55.0g及びトリエチルアミン32.0gをトルエン300mlに溶解した。10℃にて5−ノルボルネン−2−カルボン酸クロリド49.5gを加え、そのままの温度で3時間撹拌した。水100mlを30℃以下で加え、通常の後処理操作を行った。減圧蒸留を行い、目的物を得た(収率80%)。
沸点:65℃/16Pa
IR(NaCl):ν=3241,2979,1706,1257,1236,1193,1172,1153,1137,987,723cm-1
主要異性体の1H−NMR(600MHz in DMSO−d6):δ=1.23−1.29(3H,m),1.62(3H,s),1.63(3H,s),1.76(1H,dt),2.84(1H,br),2.94(1H,q),3.08(1H,br),5.84(1H,dd)6.17(1H,dd),8.31(1H,s)ppm
主要異性体の19F−NMR(565MHz in DMSO−d6 トリフルオロ酢酸標準):δ=−70.1(3F,t),−70.0(3F,t)ppm
下記モノマーの合成
[参考例2−1]3,3,3−トリフルオロ−2−トリフルオロメチル−1,2−プロパンジオールの合成
水素化ホウ素ナトリウム25.0g、水500g、ジエチルエーテル500gの混合物に、撹拌下、2−ヒドロキシ−3,3,3−トリフルオロ−2−トリフルオロメチルプロピオン酸メチル100gを滴下した。10時間撹拌後、塩酸を加えて反応を停止した。分液により得られた有機層を濃縮、続いて蒸留することにより、3,3,3−トリフルオロ−2−トリフルオロメチル−1,2−プロパンジオール83.9gを得た(収率96%)。
沸点:138℃
融点:47℃
[参考例2−2]上記モノマーの合成
[参考例2−1]で得たアルコール50.0g、5−ノルボルネン−2−カルボン酸メチル76.7g、トルエン50ml、ナトリウムメトキシド300mgの混合物を、反応により生じるメタノールを留去しながら20時間加熱還流した。反応液を冷却後、通常の水系後処理(aqueous work−up)、減圧濃縮を行い、粗生成物を得た。減圧蒸留により精製を行い、目的物を得た(収率76%)。
沸点:51〜53℃/16Pa
Claims (4)
- 下記一般式(2a)で表される繰り返し単位を有することを特徴とする含フッ素シリコーン樹脂。
(式中、X1a、X2a、X3aのうち少なくとも一つは酸素原子を表し、残りは水素原子、水酸基、ハロゲン原子、炭素数1〜20の直鎖状、分岐状、環状又は多環状骨格を持つ一価の有機基、又は炭素数1〜6の直鎖状、分岐状又は環状のアルコキシ基を表す。R 1、R2はそれぞれ独立に水素原子、又は炭素数1〜20の直鎖状、分岐状、環状又は多環状骨格を持つ一価の有機基を表す。R1、R2は互いに結合してこれらが結合する炭素原子と共に環を形成してもよい。W1、W2はそれぞれ独立にメチレン基又は酸素原子を表す。R6は水素原子、メチル基、フッ素原子又はトリフルオロメチル基を表す。pは0又は1、qは1を表す。) - (A)請求項2記載のシリコーン樹脂、
(B)酸発生剤、
(C)有機溶剤
を含有してなるレジスト組成物。 - (1)請求項3記載のレジスト組成物を基板上に塗布する工程と、
(2)次いで加熱処理後、フォトマスクを介して波長300nm以下の高エネルギー線もしくは電子線で露光する工程と、
(3)必要に応じて加熱処理した後、現像液を用いて現像する工程と
を含むことを特徴とするパターン形成方法。
Priority Applications (4)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2006069010A JP4687898B2 (ja) | 2006-03-14 | 2006-03-14 | 含フッ素ケイ素化合物、シリコーン樹脂、それを用いたレジスト組成物、及びパターン形成方法 |
US11/713,709 US7485408B2 (en) | 2006-03-14 | 2007-03-05 | Fluorine-containing silicon compounds, silicone resins, resist compositions, and patterning process |
KR1020070024369A KR100998127B1 (ko) | 2006-03-14 | 2007-03-13 | 불소 함유 규소 화합물, 실리콘 수지, 그를 이용한레지스트 조성물 및 패턴 형성 방법 |
TW096108769A TWI348594B (en) | 2006-03-14 | 2007-03-14 | Fluorine-containing silicon compounds, silicone resins, resist compositions, and patterning process |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2006069010A JP4687898B2 (ja) | 2006-03-14 | 2006-03-14 | 含フッ素ケイ素化合物、シリコーン樹脂、それを用いたレジスト組成物、及びパターン形成方法 |
Publications (2)
Publication Number | Publication Date |
---|---|
JP2007246596A JP2007246596A (ja) | 2007-09-27 |
JP4687898B2 true JP4687898B2 (ja) | 2011-05-25 |
Family
ID=38518263
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2006069010A Expired - Fee Related JP4687898B2 (ja) | 2006-03-14 | 2006-03-14 | 含フッ素ケイ素化合物、シリコーン樹脂、それを用いたレジスト組成物、及びパターン形成方法 |
Country Status (4)
Country | Link |
---|---|
US (1) | US7485408B2 (ja) |
JP (1) | JP4687898B2 (ja) |
KR (1) | KR100998127B1 (ja) |
TW (1) | TWI348594B (ja) |
Families Citing this family (12)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP4626758B2 (ja) * | 2005-07-07 | 2011-02-09 | 信越化学工業株式会社 | 含フッ素環状構造を有するケイ素化合物及びシリコーン樹脂、それを用いたレジスト組成物、及びパターン形成方法 |
JP4509080B2 (ja) * | 2006-09-28 | 2010-07-21 | 信越化学工業株式会社 | シルセスキオキサン系化合物混合物及び加水分解性シラン化合物、その製造方法及びそれを用いたレジスト組成物並びにパターン形成方法及び基板の加工方法 |
US8034965B2 (en) | 2007-11-09 | 2011-10-11 | Shin-Etsu Chemical Co., Ltd. | Norbornane skeleton structure-containing organosilicon compound and method of producing same |
TWI516527B (zh) * | 2009-12-10 | 2016-01-11 | 信越化學工業股份有限公司 | 光固化性樹脂組成物,圖案形成法和基板保護膜,以及使用該組成物之膜狀黏著劑及黏著片 |
JP5726632B2 (ja) * | 2011-05-19 | 2015-06-03 | メルクパフォーマンスマテリアルズIp合同会社 | 感光性シロキサン樹脂組成物 |
TWI567498B (zh) | 2012-04-06 | 2017-01-21 | Az電子材料盧森堡有限公司 | 負型感光性矽氧烷組成物 |
TWI567497B (zh) * | 2012-04-06 | 2017-01-21 | Az電子材料盧森堡有限公司 | 負型感光性矽氧烷組成物 |
WO2016013344A1 (ja) * | 2014-07-24 | 2016-01-28 | 日産化学工業株式会社 | カラーフィルター下層膜形成用樹脂組成物 |
JP6268111B2 (ja) * | 2015-02-06 | 2018-01-24 | 信越化学工業株式会社 | フッ素含有ケイ素化合物、その製造方法、及びフッ素含有ケイ素樹脂の製造方法 |
JP6451599B2 (ja) | 2015-11-10 | 2019-01-16 | 信越化学工業株式会社 | 重合性単量体、高分子化合物、レジスト材料、及びパターン形成方法 |
JP7111031B2 (ja) * | 2018-03-23 | 2022-08-02 | 信越化学工業株式会社 | 感光性樹脂組成物、感光性樹脂積層体、及びパターン形成方法 |
CN111825840B (zh) * | 2020-06-23 | 2022-04-22 | 湖北航天化学技术研究所 | 一种含巯基氟硅树脂、uv光固化超疏水防护涂料及制备方法 |
Citations (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2002128788A (ja) * | 2000-10-19 | 2002-05-09 | Jsr Corp | ケイ素含有脂環式化合物 |
JP2002268227A (ja) * | 2001-03-13 | 2002-09-18 | Shin Etsu Chem Co Ltd | 高分子化合物、レジスト材料及びパターン形成方法 |
JP2002278073A (ja) * | 2001-03-16 | 2002-09-27 | Jsr Corp | 感放射線性樹脂組成物 |
JP2005114942A (ja) * | 2003-10-07 | 2005-04-28 | Shin Etsu Chem Co Ltd | 感放射線性樹脂組成物並びにこれを用いたパターン形成方法 |
WO2005037846A1 (ja) * | 2003-10-15 | 2005-04-28 | Jsr Corporation | シラン化合物、ポリシロキサンおよび感放射線性樹脂組成物 |
WO2005087841A1 (ja) * | 2004-03-17 | 2005-09-22 | Jsr Corporation | 感放射線性樹脂組成物 |
JP2007015974A (ja) * | 2005-07-07 | 2007-01-25 | Shin Etsu Chem Co Ltd | 含フッ素環状構造を有するケイ素化合物及びシリコーン樹脂、それを用いたレジスト組成物、及びパターン形成方法 |
JP2007212941A (ja) * | 2006-02-13 | 2007-08-23 | Shin Etsu Chem Co Ltd | レジスト組成物並びにこれを用いたパターン形成方法 |
Family Cites Families (19)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP3830183B2 (ja) | 1995-09-29 | 2006-10-04 | 東京応化工業株式会社 | オキシムスルホネート化合物及びレジスト用酸発生剤 |
JP3587413B2 (ja) | 1995-12-20 | 2004-11-10 | 東京応化工業株式会社 | 化学増幅型レジスト組成物及びそれに用いる酸発生剤 |
JP3798458B2 (ja) | 1996-02-02 | 2006-07-19 | 東京応化工業株式会社 | オキシムスルホネート化合物及びレジスト用酸発生剤 |
TW432257B (en) * | 1997-01-31 | 2001-05-01 | Shinetsu Chemical Co | High molecular weight silicone compound, chemically amplified positive resist composition and patterning method |
JP3505990B2 (ja) | 1997-01-31 | 2004-03-15 | 信越化学工業株式会社 | 高分子シリコーン化合物、化学増幅ポジ型レジスト材料及びパターン形成方法 |
TW550439B (en) * | 1997-07-01 | 2003-09-01 | Ciba Sc Holding Ag | New oxime sulfonates as latent acids and compositions and photoresists comprising said oxime sulfonates |
JP3533951B2 (ja) | 1997-08-06 | 2004-06-07 | 信越化学工業株式会社 | 高分子シリコーン化合物、レジスト材料及びパターン形成方法 |
KR100452670B1 (ko) * | 1997-08-06 | 2005-10-11 | 신에쓰 가가꾸 고교 가부시끼가이샤 | 고분자실리콘화합물,레지스트재료및패턴형성방법 |
SG78412A1 (en) * | 1999-03-31 | 2001-02-20 | Ciba Sc Holding Ag | Oxime derivatives and the use thereof as latent acids |
JP2001215714A (ja) | 2000-02-02 | 2001-08-10 | Fuji Photo Film Co Ltd | 感放射線性樹脂組成物 |
JP2002055346A (ja) * | 2000-08-11 | 2002-02-20 | Sony Corp | 液晶配向膜の形成方法および液晶表示装置の製造方法 |
JP2002220471A (ja) | 2001-01-29 | 2002-08-09 | Jsr Corp | ポリシロキサン |
JP2003020335A (ja) | 2001-05-01 | 2003-01-24 | Jsr Corp | ポリシロキサンおよび感放射線性樹脂組成物 |
DE60234409D1 (de) * | 2001-06-29 | 2009-12-31 | Jsr Corp | Säuregenerator, Sulfonsäure, Sulfonsäurederivate und strahlungsempfindliche Zusammensetzung |
JP3826777B2 (ja) | 2001-12-05 | 2006-09-27 | Jsr株式会社 | 感放射線性樹脂組成物 |
JP4079799B2 (ja) * | 2003-02-24 | 2008-04-23 | セントラル硝子株式会社 | 含フッ素化合物の製法 |
JP2005222040A (ja) * | 2003-12-30 | 2005-08-18 | Rohm & Haas Electronic Materials Llc | Si−成分を含むフォトレジスト組成物 |
JP2006022319A (ja) | 2004-06-11 | 2006-01-26 | Shin Etsu Chem Co Ltd | 硬化性パーフルオロポリエーテル組成物及びその硬化物を用いたゴム及びゲル製品 |
US20050277731A1 (en) * | 2004-06-11 | 2005-12-15 | Shin-Etsu Chemical Co., Ltd. | Curable perfluoropolyether compositions and rubber or gel articles comprising the same |
-
2006
- 2006-03-14 JP JP2006069010A patent/JP4687898B2/ja not_active Expired - Fee Related
-
2007
- 2007-03-05 US US11/713,709 patent/US7485408B2/en active Active
- 2007-03-13 KR KR1020070024369A patent/KR100998127B1/ko active IP Right Grant
- 2007-03-14 TW TW096108769A patent/TWI348594B/zh not_active IP Right Cessation
Patent Citations (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2002128788A (ja) * | 2000-10-19 | 2002-05-09 | Jsr Corp | ケイ素含有脂環式化合物 |
JP2002268227A (ja) * | 2001-03-13 | 2002-09-18 | Shin Etsu Chem Co Ltd | 高分子化合物、レジスト材料及びパターン形成方法 |
JP2002278073A (ja) * | 2001-03-16 | 2002-09-27 | Jsr Corp | 感放射線性樹脂組成物 |
JP2005114942A (ja) * | 2003-10-07 | 2005-04-28 | Shin Etsu Chem Co Ltd | 感放射線性樹脂組成物並びにこれを用いたパターン形成方法 |
WO2005037846A1 (ja) * | 2003-10-15 | 2005-04-28 | Jsr Corporation | シラン化合物、ポリシロキサンおよび感放射線性樹脂組成物 |
WO2005087841A1 (ja) * | 2004-03-17 | 2005-09-22 | Jsr Corporation | 感放射線性樹脂組成物 |
JP2007015974A (ja) * | 2005-07-07 | 2007-01-25 | Shin Etsu Chem Co Ltd | 含フッ素環状構造を有するケイ素化合物及びシリコーン樹脂、それを用いたレジスト組成物、及びパターン形成方法 |
JP2007212941A (ja) * | 2006-02-13 | 2007-08-23 | Shin Etsu Chem Co Ltd | レジスト組成物並びにこれを用いたパターン形成方法 |
Also Published As
Publication number | Publication date |
---|---|
JP2007246596A (ja) | 2007-09-27 |
KR100998127B1 (ko) | 2010-12-02 |
KR20070093846A (ko) | 2007-09-19 |
TWI348594B (en) | 2011-09-11 |
TW200804987A (en) | 2008-01-16 |
US20070218402A1 (en) | 2007-09-20 |
US7485408B2 (en) | 2009-02-03 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
JP4687898B2 (ja) | 含フッ素ケイ素化合物、シリコーン樹脂、それを用いたレジスト組成物、及びパターン形成方法 | |
JP4488229B2 (ja) | 環状構造を有する含フッ素単量体、その製造方法、重合体、フォトレジスト組成物及びパターン形成方法 | |
JP4687878B2 (ja) | 高分子化合物、レジスト材料及びパターン形成方法 | |
JP4013044B2 (ja) | レジスト材料、及びパターン形成方法 | |
JP4831307B2 (ja) | 新規なエステル化合物、高分子化合物、レジスト材料及びパターン形成方法 | |
KR101042460B1 (ko) | 환상 구조를 갖는 불소 함유 단량체, 그의 제조 방법,중합체, 포토레지스트 조성물 및 패턴 형성 방법 | |
JP4666177B2 (ja) | 高分子化合物、化学増幅ポジ型レジスト材料及びパターン形成方法 | |
JP4431888B2 (ja) | 含フッ素重合性化合物、その製造方法、この化合物から得られる高分子化合物、レジスト材料及びこれを用いたパターン形成方法 | |
JP4085034B2 (ja) | 化合物、高分子化合物、レジスト材料及びパターン形成方法 | |
JP4371206B2 (ja) | エステル化合物、高分子化合物、レジスト材料、及びパターン形成方法 | |
US7037995B2 (en) | Tertiary (meth)acrylates having lactone structure, polymers, resist compositions and patterning process | |
JP2006213835A (ja) | 高分子化合物、レジスト材料及びパターン形成方法 | |
JP4626758B2 (ja) | 含フッ素環状構造を有するケイ素化合物及びシリコーン樹脂、それを用いたレジスト組成物、及びパターン形成方法 | |
JP4302585B2 (ja) | 重合性化合物、高分子化合物及びポジ型レジスト材料並びにこれを用いたパターン形成方法 | |
JP4407814B2 (ja) | レジスト材料及びパターン形成方法 | |
JP4240202B2 (ja) | スルホン酸エステル基を有する高分子化合物、レジスト材料及びパターン形成方法 | |
JP4178360B2 (ja) | 脂環構造を有する新規エポキシ化合物、高分子化合物、レジスト材料、及びパターン形成方法 | |
JP4016270B2 (ja) | 高分子化合物、レジスト材料及びパターン形成方法 | |
JP4186051B2 (ja) | 新規なエステル化合物、高分子化合物、レジスト材料及びパターン形成方法 |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
A621 | Written request for application examination |
Free format text: JAPANESE INTERMEDIATE CODE: A621 Effective date: 20080125 |
|
A977 | Report on retrieval |
Free format text: JAPANESE INTERMEDIATE CODE: A971007 Effective date: 20100215 |
|
A131 | Notification of reasons for refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A131 Effective date: 20100224 |
|
A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20100331 |
|
TRDD | Decision of grant or rejection written | ||
A01 | Written decision to grant a patent or to grant a registration (utility model) |
Free format text: JAPANESE INTERMEDIATE CODE: A01 Effective date: 20110119 |
|
A01 | Written decision to grant a patent or to grant a registration (utility model) |
Free format text: JAPANESE INTERMEDIATE CODE: A01 |
|
A61 | First payment of annual fees (during grant procedure) |
Free format text: JAPANESE INTERMEDIATE CODE: A61 Effective date: 20110201 |
|
R150 | Certificate of patent or registration of utility model |
Ref document number: 4687898 Country of ref document: JP Free format text: JAPANESE INTERMEDIATE CODE: R150 |
|
FPAY | Renewal fee payment (event date is renewal date of database) |
Free format text: PAYMENT UNTIL: 20140225 Year of fee payment: 3 |
|
LAPS | Cancellation because of no payment of annual fees |