JP5016338B2

JP5016338B2 - 光酸発生剤および光反応性組成物

光酸発生剤および光反応性組成物 Download PDF

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Publication number: JP5016338B2
Authority: JP; Japan
Prior art keywords: bis; bithiophene; group; diylbis; sulfonium
Prior art date: 2007-03-26
Legal status : Expired - Fee Related

Application number

JP2007079758A

Other languages

English (en)

Japanese (ja)

Other versions

JP2008239519A5 (enExample

JP2008239519A (ja

Inventor

勝政山本

三千雄鈴木

Current Assignee

Sumitomo Seika Chemicals Co Ltd

Original Assignee

Sumitomo Seika Chemicals Co Ltd

Priority date

2007-03-26

Filing date

2007-03-26

Publication date

2012-09-05

2007-03-26 Application filed by Sumitomo Seika Chemicals Co Ltd filed Critical Sumitomo Seika Chemicals Co Ltd

2007-03-26 Priority to JP2007079758A priority Critical patent/JP5016338B2/ja

2008-10-09 Publication of JP2008239519A publication Critical patent/JP2008239519A/ja

2010-03-25 Publication of JP2008239519A5 publication Critical patent/JP2008239519A5/ja

2012-09-05 Application granted granted Critical

2012-09-05 Publication of JP5016338B2 publication Critical patent/JP5016338B2/ja

Status Expired - Fee Related legal-status Critical Current

2027-03-26 Anticipated expiration legal-status Critical

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239000000203 mixture Substances 0.000 title claims abstract description 51
OHZAHWOAMVVGEL-UHFFFAOYSA-N 2,2'-bithiophene Chemical compound C1=CSC(C=2SC=CC=2)=C1 OHZAHWOAMVVGEL-UHFFFAOYSA-N 0.000 claims abstract description 56
125000001424 substituent group Chemical group 0.000 claims abstract description 35
150000003839 salts Chemical class 0.000 claims abstract description 28
239000002253 acid Substances 0.000 claims abstract description 27
125000003367 polycyclic group Chemical group 0.000 claims abstract description 6
125000002911 monocyclic heterocycle group Chemical group 0.000 claims abstract description 5
-1 inorganic acid ion Chemical class 0.000 claims description 187
150000001875 compounds Chemical class 0.000 claims description 32
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 14
125000004432 carbon atom Chemical group C* 0.000 claims description 11
125000001620 monocyclic carbocycle group Chemical group 0.000 claims description 6
125000002837 carbocyclic group Chemical group 0.000 claims description 5
125000003545 alkoxy group Chemical group 0.000 claims description 4
125000000217 alkyl group Chemical group 0.000 claims description 4
125000001624 naphthyl group Chemical group 0.000 claims description 4
125000001544 thienyl group Chemical group 0.000 claims description 4
125000004414 alkyl thio group Chemical group 0.000 claims description 3
125000005843 halogen group Chemical group 0.000 claims description 3
125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 claims description 2
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical class S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 claims 1
238000006243 chemical reaction Methods 0.000 abstract description 40
230000035484 reaction time Effects 0.000 abstract description 5
230000035945 sensitivity Effects 0.000 abstract description 5
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 abstract description 4
125000002950 monocyclic group Chemical group 0.000 abstract 1
RWSOTUBLDIXVET-UHFFFAOYSA-O sulfonium Chemical compound [SH3+] RWSOTUBLDIXVET-UHFFFAOYSA-O 0.000 description 86
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 33
125000000590 4-methylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 29
125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 24
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 21
238000006482 condensation reaction Methods 0.000 description 20
MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 19
229910052783 alkali metal Inorganic materials 0.000 description 17
239000007864 aqueous solution Substances 0.000 description 15
239000013078 crystal Substances 0.000 description 15
AFVFQIVMOAPDHO-UHFFFAOYSA-N methanesulfonic acid Substances CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 15
239000000243 solution Substances 0.000 description 15
238000003756 stirring Methods 0.000 description 15
239000007795 chemical reaction product Substances 0.000 description 14
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 14
150000003462 sulfoxides Chemical class 0.000 description 13
239000012141 concentrate Substances 0.000 description 12
229910052731 fluorine Inorganic materials 0.000 description 12
NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 12
229910052739 hydrogen Inorganic materials 0.000 description 10
238000000034 method Methods 0.000 description 10
229910052760 oxygen Inorganic materials 0.000 description 10
229910052717 sulfur Inorganic materials 0.000 description 10
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 9
IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 9
LVTHXRLARFLXNR-UHFFFAOYSA-M potassium;1,1,2,2,3,3,4,4,4-nonafluorobutane-1-sulfonate Chemical class [K+].[O-]S(=O)(=O)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F LVTHXRLARFLXNR-UHFFFAOYSA-M 0.000 description 9
LWNGJAHMBMVCJR-UHFFFAOYSA-N (2,3,4,5,6-pentafluorophenoxy)boronic acid Chemical compound OB(O)OC1=C(F)C(F)=C(F)C(F)=C1F LWNGJAHMBMVCJR-UHFFFAOYSA-N 0.000 description 8
238000010521 absorption reaction Methods 0.000 description 8
239000003795 chemical substances by application Substances 0.000 description 8
230000000052 comparative effect Effects 0.000 description 8
229940098779 methanesulfonic acid Drugs 0.000 description 8
238000001914 filtration Methods 0.000 description 7
MJWNJEJCQHNDNM-UHFFFAOYSA-N 1-methyl-4-(4-methylphenyl)sulfinylbenzene Chemical compound C1=CC(C)=CC=C1S(=O)C1=CC=C(C)C=C1 MJWNJEJCQHNDNM-UHFFFAOYSA-N 0.000 description 6
NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 6
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 6
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 6
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
229940063013 borate ion Drugs 0.000 description 6
238000004519 manufacturing process Methods 0.000 description 6
239000003960 organic solvent Substances 0.000 description 6
229910052700 potassium Inorganic materials 0.000 description 6
239000011591 potassium Substances 0.000 description 6
229910052708 sodium Inorganic materials 0.000 description 6
239000011734 sodium Substances 0.000 description 6
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 5
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 5
QZEBXOMPTUTXOI-UHFFFAOYSA-N SSC1=CC=C(C2=CC=CS2)S1 Chemical compound SSC1=CC=C(C2=CC=CS2)S1 QZEBXOMPTUTXOI-UHFFFAOYSA-N 0.000 description 5
230000000694 effects Effects 0.000 description 5
238000000921 elemental analysis Methods 0.000 description 5
RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
238000004128 high performance liquid chromatography Methods 0.000 description 5
238000002844 melting Methods 0.000 description 5
230000008018 melting Effects 0.000 description 5
239000002904 solvent Substances 0.000 description 5
LEDPSBGADKSDKI-UHFFFAOYSA-N 1-methoxy-4-(4-methoxyphenyl)sulfinylbenzene Chemical compound C1=CC(OC)=CC=C1S(=O)C1=CC=C(OC)C=C1 LEDPSBGADKSDKI-UHFFFAOYSA-N 0.000 description 4
HZNVUJQVZSTENZ-UHFFFAOYSA-N 2,3-dichloro-5,6-dicyano-1,4-benzoquinone Chemical compound ClC1=C(Cl)C(=O)C(C#N)=C(C#N)C1=O HZNVUJQVZSTENZ-UHFFFAOYSA-N 0.000 description 4
IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 4
239000007810 chemical reaction solvent Substances 0.000 description 4
239000000460 chlorine Substances 0.000 description 4
150000007522 mineralic acids Chemical class 0.000 description 4
238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 4
150000007524 organic acids Chemical class 0.000 description 4
229920000642 polymer Polymers 0.000 description 4
238000006116 polymerization reaction Methods 0.000 description 4
LCIOIBLOWNIOOF-UHFFFAOYSA-N (2,3-difluorophenoxy)boronic acid Chemical compound OB(O)OC1=CC=CC(F)=C1F LCIOIBLOWNIOOF-UHFFFAOYSA-N 0.000 description 3
XWCKWTGFRGOTNX-UHFFFAOYSA-N 1-(2,4-dimethylphenyl)sulfinyl-2,4-dimethylbenzene Chemical compound CC1=CC(C)=CC=C1S(=O)C1=CC=C(C)C=C1C XWCKWTGFRGOTNX-UHFFFAOYSA-N 0.000 description 3
125000004860 4-ethylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])C([H])([H])[H] 0.000 description 3
125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 description 3
125000004861 4-isopropyl phenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 3
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
UVSSPWOKVSKHCU-UHFFFAOYSA-N [2-(trifluoromethyl)phenoxy]boronic acid Chemical compound OB(O)OC1=CC=CC=C1C(F)(F)F UVSSPWOKVSKHCU-UHFFFAOYSA-N 0.000 description 3
125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 3
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
238000011156 evaluation Methods 0.000 description 3
239000011521 glass Substances 0.000 description 3
230000020169 heat generation Effects 0.000 description 3
239000003112 inhibitor Substances 0.000 description 3
238000005259 measurement Methods 0.000 description 3
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 3
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
238000002156 mixing Methods 0.000 description 3
239000000178 monomer Substances 0.000 description 3
229920003986 novolac Polymers 0.000 description 3
RUOJZAUFBMNUDX-UHFFFAOYSA-N propylene carbonate Chemical compound CC1COC(=O)O1 RUOJZAUFBMNUDX-UHFFFAOYSA-N 0.000 description 3
DLYUQMMRRRQYAE-UHFFFAOYSA-N tetraphosphorus decaoxide Chemical compound O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 3
YNMOCOVMVLEFTQ-UHFFFAOYSA-N 1-butoxy-4-(4-butoxyphenyl)sulfinylbenzene Chemical compound C1=CC(OCCCC)=CC=C1S(=O)C1=CC=C(OCCCC)C=C1 YNMOCOVMVLEFTQ-UHFFFAOYSA-N 0.000 description 2
ZMAMWZGXGKVHAD-UHFFFAOYSA-N 1-butyl-4-(4-butylphenyl)sulfinylbenzene Chemical compound C1=CC(CCCC)=CC=C1S(=O)C1=CC=C(CCCC)C=C1 ZMAMWZGXGKVHAD-UHFFFAOYSA-N 0.000 description 2
YDLTZPSNBGEXFJ-UHFFFAOYSA-N 1-ethoxy-4-(4-ethoxyphenyl)sulfinylbenzene Chemical compound C1=CC(OCC)=CC=C1S(=O)C1=CC=C(OCC)C=C1 YDLTZPSNBGEXFJ-UHFFFAOYSA-N 0.000 description 2
BNZXXGYQOJEXFD-UHFFFAOYSA-N 1-ethyl-4-(4-ethylphenyl)sulfinylbenzene Chemical compound C1=CC(CC)=CC=C1S(=O)C1=CC=C(CC)C=C1 BNZXXGYQOJEXFD-UHFFFAOYSA-N 0.000 description 2
GVYKABJIEOOUOX-UHFFFAOYSA-N 1-fluoro-4-(4-fluorophenyl)sulfinylbenzene Chemical compound C1=CC(F)=CC=C1S(=O)C1=CC=C(F)C=C1 GVYKABJIEOOUOX-UHFFFAOYSA-N 0.000 description 2
KTSCVUAOZGZAJW-UHFFFAOYSA-N 1-methylsulfanyl-4-(4-methylsulfanylphenyl)sulfinylbenzene Chemical compound C1=CC(SC)=CC=C1S(=O)C1=CC=C(SC)C=C1 KTSCVUAOZGZAJW-UHFFFAOYSA-N 0.000 description 2
YKQHKGKTRFCZHR-UHFFFAOYSA-N 1-propan-2-yl-4-(4-propan-2-ylphenyl)sulfinylbenzene Chemical compound C1=CC(C(C)C)=CC=C1S(=O)C1=CC=C(C(C)C)C=C1 YKQHKGKTRFCZHR-UHFFFAOYSA-N 0.000 description 2
VAJFPULOICWGIM-UHFFFAOYSA-N 1-propan-2-yloxy-4-(4-propan-2-yloxyphenyl)sulfinylbenzene Chemical compound C1=CC(OC(C)C)=CC=C1S(=O)C1=CC=C(OC(C)C)C=C1 VAJFPULOICWGIM-UHFFFAOYSA-N 0.000 description 2
PFSQZRJOMSCCHE-UHFFFAOYSA-N 1-propoxy-4-(4-propoxyphenyl)sulfinylbenzene Chemical compound C1=CC(OCCC)=CC=C1S(=O)C1=CC=C(OCCC)C=C1 PFSQZRJOMSCCHE-UHFFFAOYSA-N 0.000 description 2
SOPHXAWFFIVWOS-UHFFFAOYSA-N 1-propyl-4-(4-propylphenyl)sulfinylbenzene Chemical compound C1=CC(CCC)=CC=C1S(=O)C1=CC=C(CCC)C=C1 SOPHXAWFFIVWOS-UHFFFAOYSA-N 0.000 description 2
WVXLLHWEQSZBLW-UHFFFAOYSA-N 2-(4-acetyl-2-methoxyphenoxy)acetic acid Chemical compound COC1=CC(C(C)=O)=CC=C1OCC(O)=O WVXLLHWEQSZBLW-UHFFFAOYSA-N 0.000 description 2
XLLIQLLCWZCATF-UHFFFAOYSA-N 2-methoxyethyl acetate Chemical compound COCCOC(C)=O XLLIQLLCWZCATF-UHFFFAOYSA-N 0.000 description 2
DUZUYBOBIMKSPF-UHFFFAOYSA-N 2-naphthalen-2-ylsulfanylnaphthalene Chemical compound C1=CC=CC2=CC(SC=3C=C4C=CC=CC4=CC=3)=CC=C21 DUZUYBOBIMKSPF-UHFFFAOYSA-N 0.000 description 2
AKYIWBKPINOXJY-UHFFFAOYSA-N 2-thiophen-2-ylsulfanylthiophene Chemical compound C=1C=CSC=1SC1=CC=CS1 AKYIWBKPINOXJY-UHFFFAOYSA-N 0.000 description 2
YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 description 2
UDAAWQWWHSCSMS-UHFFFAOYSA-N 5-propylsulfanyl-7-thiabicyclo[4.1.0]hepta-1(6),2,4-triene Chemical compound CCCSC1=CC=CC2=C1S2 UDAAWQWWHSCSMS-UHFFFAOYSA-N 0.000 description 2
KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 2
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 2
JJHHIJFTHRNPIK-UHFFFAOYSA-N Diphenyl sulfoxide Chemical compound C=1C=CC=CC=1S(=O)C1=CC=CC=C1 JJHHIJFTHRNPIK-UHFFFAOYSA-N 0.000 description 2
239000004593 Epoxy Substances 0.000 description 2
QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 2
PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
229910052782 aluminium Inorganic materials 0.000 description 2
XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 2
VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
238000004458 analytical method Methods 0.000 description 2
PXKLMJQFEQBVLD-UHFFFAOYSA-N bisphenol F Chemical compound C1=CC(O)=CC=C1CC1=CC=C(O)C=C1 PXKLMJQFEQBVLD-UHFFFAOYSA-N 0.000 description 2
125000002091 cationic group Chemical group 0.000 description 2
238000000576 coating method Methods 0.000 description 2
GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical class C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 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
LZCLXQDLBQLTDK-UHFFFAOYSA-N ethyl 2-hydroxypropanoate Chemical compound CCOC(=O)C(C)O LZCLXQDLBQLTDK-UHFFFAOYSA-N 0.000 description 2
125000001153 fluoro group Chemical group F* 0.000 description 2
125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 description 2
150000002500 ions Chemical class 0.000 description 2
230000001678 irradiating effect Effects 0.000 description 2
125000003253 isopropoxy group Chemical group [H]C([H])([H])C([H])(O*)C([H])([H])[H] 0.000 description 2
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
239000007788 liquid Substances 0.000 description 2
IVSZLXZYQVIEFR-UHFFFAOYSA-N m-xylene Chemical group CC1=CC=CC(C)=C1 IVSZLXZYQVIEFR-UHFFFAOYSA-N 0.000 description 2
239000000463 material Substances 0.000 description 2
QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 2
229910052753 mercury Inorganic materials 0.000 description 2
125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 description 2
239000011259 mixed solution Substances 0.000 description 2
125000006606 n-butoxy group Chemical group 0.000 description 2
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
125000003506 n-propoxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])O* 0.000 description 2
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
BKIMMITUMNQMOS-UHFFFAOYSA-N nonane Chemical compound CCCCCCCCC BKIMMITUMNQMOS-UHFFFAOYSA-N 0.000 description 2
235000005985 organic acids Nutrition 0.000 description 2
150000002921 oxetanes Chemical class 0.000 description 2
125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 2
229910052698 phosphorus Inorganic materials 0.000 description 2
GLGXXYFYZWQGEL-UHFFFAOYSA-M potassium;trifluoromethanesulfonate Chemical class [K+].[O-]S(=O)(=O)C(F)(F)F GLGXXYFYZWQGEL-UHFFFAOYSA-M 0.000 description 2
239000000047 product Substances 0.000 description 2
238000007086 side reaction Methods 0.000 description 2
QBJDFZSOZNDVDE-UHFFFAOYSA-M sodium;1,1,2,2,3,3,4,4,4-nonafluorobutane-1-sulfonate Chemical class [Na+].[O-]S(=O)(=O)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F QBJDFZSOZNDVDE-UHFFFAOYSA-M 0.000 description 2
XGPOMXSYOKFBHS-UHFFFAOYSA-M sodium;trifluoromethanesulfonate Chemical class [Na+].[O-]S(=O)(=O)C(F)(F)F XGPOMXSYOKFBHS-UHFFFAOYSA-M 0.000 description 2
239000007787 solid Substances 0.000 description 2
125000003003 spiro group Chemical group 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
125000005409 triarylsulfonium group Chemical group 0.000 description 2
ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 description 2
QAEDZJGFFMLHHQ-UHFFFAOYSA-N trifluoroacetic anhydride Chemical compound FC(F)(F)C(=O)OC(=O)C(F)(F)F QAEDZJGFFMLHHQ-UHFFFAOYSA-N 0.000 description 2
125000001889 triflyl group Chemical group FC(F)(F)S(*)(=O)=O 0.000 description 2
UNMJLQGKEDTEKJ-UHFFFAOYSA-N (3-ethyloxetan-3-yl)methanol Chemical compound CCC1(CO)COC1 UNMJLQGKEDTEKJ-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
ZXHDVRATSGZISC-UHFFFAOYSA-N 1,2-bis(ethenoxy)ethane Chemical compound C=COCCOC=C ZXHDVRATSGZISC-UHFFFAOYSA-N 0.000 description 1
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239000000539 dimer Substances 0.000 description 1
OBUXZYGZZJCYID-UHFFFAOYSA-L dipotassium;9,10-dioxoanthracene-1,5-disulfonate Chemical class [K+].[K+].O=C1C=2C(S(=O)(=O)[O-])=CC=CC=2C(=O)C2=C1C=CC=C2S([O-])(=O)=O OBUXZYGZZJCYID-UHFFFAOYSA-L 0.000 description 1
OBTFKRQJZSUBCQ-UHFFFAOYSA-L dipotassium;benzene-1,3-disulfonate Chemical class [K+].[K+].[O-]S(=O)(=O)C1=CC=CC(S([O-])(=O)=O)=C1 OBTFKRQJZSUBCQ-UHFFFAOYSA-L 0.000 description 1
OFASSSMJNCWWTP-UHFFFAOYSA-L disodium;9,10-dioxoanthracene-1,5-disulfonate Chemical class [Na+].[Na+].O=C1C=2C(S(=O)(=O)[O-])=CC=CC=2C(=O)C2=C1C=CC=C2S([O-])(=O)=O OFASSSMJNCWWTP-UHFFFAOYSA-L 0.000 description 1
XWPWZOJBTOJEGW-UHFFFAOYSA-L disodium;benzene-1,3-disulfonate Chemical class [Na+].[Na+].[O-]S(=O)(=O)C1=CC=CC(S([O-])(=O)=O)=C1 XWPWZOJBTOJEGW-UHFFFAOYSA-L 0.000 description 1
YQGOJNYOYNNSMM-UHFFFAOYSA-N eosin Chemical compound [Na+].OC(=O)C1=CC=CC=C1C1=C2C=C(Br)C(=O)C(Br)=C2OC2=C(Br)C(O)=C(Br)C=C21 YQGOJNYOYNNSMM-UHFFFAOYSA-N 0.000 description 1
CCIVGXIOQKPBKL-UHFFFAOYSA-M ethanesulfonate Chemical compound CCS([O-])(=O)=O CCIVGXIOQKPBKL-UHFFFAOYSA-M 0.000 description 1
238000006266 etherification reaction Methods 0.000 description 1
229940116333 ethyl lactate Drugs 0.000 description 1
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239000010408 film Substances 0.000 description 1
230000002070 germicidal effect Effects 0.000 description 1
RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 description 1
FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 1
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 1
125000002768 hydroxyalkyl group Chemical group 0.000 description 1
239000003999 initiator Substances 0.000 description 1
229910052740 iodine Inorganic materials 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
239000012948 isocyanate Substances 0.000 description 1
150000002513 isocyanates Chemical class 0.000 description 1
FDZZZRQASAIRJF-UHFFFAOYSA-M malachite green Chemical compound [Cl-].C1=CC(N(C)C)=CC=C1C(C=1C=CC=CC=1)=C1C=CC(=[N+](C)C)C=C1 FDZZZRQASAIRJF-UHFFFAOYSA-M 0.000 description 1
229940107698 malachite green Drugs 0.000 description 1
229910001507 metal halide Inorganic materials 0.000 description 1
150000005309 metal halides Chemical class 0.000 description 1
CXKWCBBOMKCUKX-UHFFFAOYSA-M methylene blue Chemical compound [Cl-].C1=CC(N(C)C)=CC2=[S+]C3=CC(N(C)C)=CC=C3N=C21 CXKWCBBOMKCUKX-UHFFFAOYSA-M 0.000 description 1
229960000907 methylthioninium chloride Drugs 0.000 description 1
SFBTTWXNCQVIEC-UHFFFAOYSA-N o-Vinylanisole Chemical compound COC1=CC=CC=C1C=C SFBTTWXNCQVIEC-UHFFFAOYSA-N 0.000 description 1
TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
AHHWIHXENZJRFG-UHFFFAOYSA-N oxetane Chemical compound C1COC1 AHHWIHXENZJRFG-UHFFFAOYSA-N 0.000 description 1
IVUSOGDLVUEEQB-UHFFFAOYSA-N oxido(dioxo)-$l^{5}-stibane Chemical compound [O-][Sb](=O)=O IVUSOGDLVUEEQB-UHFFFAOYSA-N 0.000 description 1
NWVVVBRKAWDGAB-UHFFFAOYSA-N p-methoxyphenol Chemical compound COC1=CC=C(O)C=C1 NWVVVBRKAWDGAB-UHFFFAOYSA-N 0.000 description 1
LPNBBFKOUUSUDB-UHFFFAOYSA-N p-toluenecarboxylic acid Natural products CC1=CC=C(C(O)=O)C=C1 LPNBBFKOUUSUDB-UHFFFAOYSA-N 0.000 description 1
JOXIMZWYDAKGHI-UHFFFAOYSA-N p-toluenesulfonic acid Substances CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
UCUUFSAXZMGPGH-UHFFFAOYSA-N penta-1,4-dien-3-one Chemical compound C=CC(=O)C=C UCUUFSAXZMGPGH-UHFFFAOYSA-N 0.000 description 1
125000000538 pentafluorophenyl group Chemical group FC1=C(F)C(F)=C(*)C(F)=C1F 0.000 description 1
125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
JGTNAGYHADQMCM-UHFFFAOYSA-N perfluorobutanesulfonic acid Chemical compound OS(=O)(=O)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F JGTNAGYHADQMCM-UHFFFAOYSA-N 0.000 description 1
238000006552 photochemical reaction Methods 0.000 description 1
229920000137 polyphosphoric acid Polymers 0.000 description 1
229920001451 polypropylene glycol Polymers 0.000 description 1
SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical class [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 1
XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical class [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
BWILYWWHXDGKQA-UHFFFAOYSA-M potassium propanoate Chemical class [K+].CCC([O-])=O BWILYWWHXDGKQA-UHFFFAOYSA-M 0.000 description 1
CUNPJFGIODEJLQ-UHFFFAOYSA-M potassium;2,2,2-trifluoroacetate Chemical class [K+].[O-]C(=O)C(F)(F)F CUNPJFGIODEJLQ-UHFFFAOYSA-M 0.000 description 1
GHKGUEZUGFJUEJ-UHFFFAOYSA-M potassium;4-methylbenzenesulfonate Chemical class [K+].CC1=CC=C(S([O-])(=O)=O)C=C1 GHKGUEZUGFJUEJ-UHFFFAOYSA-M 0.000 description 1
DKEYEXQVFHUPLU-UHFFFAOYSA-M potassium;4-methylbenzoate Chemical class [K+].CC1=CC=C(C([O-])=O)C=C1 DKEYEXQVFHUPLU-UHFFFAOYSA-M 0.000 description 1
BMAWOUMCJNTMPB-UHFFFAOYSA-M potassium;9,10-dioxoanthracene-1-sulfonate Chemical class [K+].O=C1C2=CC=CC=C2C(=O)C2=C1C=CC=C2S(=O)(=O)[O-] BMAWOUMCJNTMPB-UHFFFAOYSA-M 0.000 description 1
ORLDOQWUTSYDAC-UHFFFAOYSA-M potassium;9,10-dioxoanthracene-2-sulfonate Chemical class [K+].C1=CC=C2C(=O)C3=CC(S(=O)(=O)[O-])=CC=C3C(=O)C2=C1 ORLDOQWUTSYDAC-UHFFFAOYSA-M 0.000 description 1
JEVKEOBMAMOJLP-UHFFFAOYSA-M potassium;butane-1-sulfonate Chemical class [K+].CCCCS([O-])(=O)=O JEVKEOBMAMOJLP-UHFFFAOYSA-M 0.000 description 1
RWMKSKOZLCXHOK-UHFFFAOYSA-M potassium;butanoate Chemical class [K+].CCCC([O-])=O RWMKSKOZLCXHOK-UHFFFAOYSA-M 0.000 description 1
CHUPNGGCNPHUEN-UHFFFAOYSA-M potassium;ethanesulfonate Chemical class [K+].CCS([O-])(=O)=O CHUPNGGCNPHUEN-UHFFFAOYSA-M 0.000 description 1
XWIJIXWOZCRYEL-UHFFFAOYSA-M potassium;methanesulfonate Chemical class [K+].CS([O-])(=O)=O XWIJIXWOZCRYEL-UHFFFAOYSA-M 0.000 description 1
WQEDQSDEIXNCCI-UHFFFAOYSA-M potassium;nonanoate Chemical class [K+].CCCCCCCCC([O-])=O WQEDQSDEIXNCCI-UHFFFAOYSA-M 0.000 description 1
SJVZUJVRHXYCSP-UHFFFAOYSA-M potassium;octane-1-sulfonate Chemical class [K+].CCCCCCCCS([O-])(=O)=O SJVZUJVRHXYCSP-UHFFFAOYSA-M 0.000 description 1
OPCDHYPGIGFJGH-UHFFFAOYSA-M potassium;pentanoate Chemical class [K+].CCCCC([O-])=O OPCDHYPGIGFJGH-UHFFFAOYSA-M 0.000 description 1
ZQUDHVGNIZTEDK-UHFFFAOYSA-M potassium;propane-1-sulfonate Chemical class [K+].CCCS([O-])(=O)=O ZQUDHVGNIZTEDK-UHFFFAOYSA-M 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
HJWLCRVIBGQPNF-UHFFFAOYSA-N prop-2-enylbenzene Chemical compound C=CCC1=CC=CC=C1 HJWLCRVIBGQPNF-UHFFFAOYSA-N 0.000 description 1
125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
LLHKCFNBLRBOGN-UHFFFAOYSA-N propylene glycol methyl ether acetate Chemical compound COCC(C)OC(C)=O LLHKCFNBLRBOGN-UHFFFAOYSA-N 0.000 description 1
125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
238000000746 purification Methods 0.000 description 1
238000011160 research Methods 0.000 description 1
229920005989 resin Polymers 0.000 description 1
239000011347 resin Substances 0.000 description 1
GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 1
229960001755 resorcinol Drugs 0.000 description 1
GGCZERPQGJTIQP-UHFFFAOYSA-M sodium 2-anthraquinonesulfonate Chemical class [Na+].C1=CC=C2C(=O)C3=CC(S(=O)(=O)[O-])=CC=C3C(=O)C2=C1 GGCZERPQGJTIQP-UHFFFAOYSA-M 0.000 description 1
229940077386 sodium benzenesulfonate Drugs 0.000 description 1
WXMKPNITSTVMEF-UHFFFAOYSA-M sodium benzoate Chemical class [Na+].[O-]C(=O)C1=CC=CC=C1 WXMKPNITSTVMEF-UHFFFAOYSA-M 0.000 description 1
MFBOGIVSZKQAPD-UHFFFAOYSA-M sodium butyrate Chemical class [Na+].CCCC([O-])=O MFBOGIVSZKQAPD-UHFFFAOYSA-M 0.000 description 1
JXKPEJDQGNYQSM-UHFFFAOYSA-M sodium propionate Chemical class [Na+].CCC([O-])=O JXKPEJDQGNYQSM-UHFFFAOYSA-M 0.000 description 1
229910001495 sodium tetrafluoroborate Inorganic materials 0.000 description 1
UYCAUPASBSROMS-UHFFFAOYSA-M sodium;2,2,2-trifluoroacetate Chemical class [Na+].[O-]C(=O)C(F)(F)F UYCAUPASBSROMS-UHFFFAOYSA-M 0.000 description 1
MNCGMVDMOKPCSQ-UHFFFAOYSA-M sodium;2-phenylethenesulfonate Chemical compound [Na+].[O-]S(=O)(=O)C=CC1=CC=CC=C1 MNCGMVDMOKPCSQ-UHFFFAOYSA-M 0.000 description 1
KVCGISUBCHHTDD-UHFFFAOYSA-M sodium;4-methylbenzenesulfonate Chemical class [Na+].CC1=CC=C(S([O-])(=O)=O)C=C1 KVCGISUBCHHTDD-UHFFFAOYSA-M 0.000 description 1
GNCGTEQGBYYYBX-UHFFFAOYSA-M sodium;4-methylbenzoate Chemical class [Na+].CC1=CC=C(C([O-])=O)C=C1 GNCGTEQGBYYYBX-UHFFFAOYSA-M 0.000 description 1
MZSDGDXXBZSFTG-UHFFFAOYSA-M sodium;benzenesulfonate Chemical class [Na+].[O-]S(=O)(=O)C1=CC=CC=C1 MZSDGDXXBZSFTG-UHFFFAOYSA-M 0.000 description 1
XQCHMGAOAWZUPI-UHFFFAOYSA-M sodium;butane-1-sulfonate Chemical class [Na+].CCCCS([O-])(=O)=O XQCHMGAOAWZUPI-UHFFFAOYSA-M 0.000 description 1
KQFAFFYKLIBKDE-UHFFFAOYSA-M sodium;ethanesulfonate Chemical class [Na+].CCS([O-])(=O)=O KQFAFFYKLIBKDE-UHFFFAOYSA-M 0.000 description 1
KKVTYAVXTDIPAP-UHFFFAOYSA-M sodium;methanesulfonate Chemical class [Na+].CS([O-])(=O)=O KKVTYAVXTDIPAP-UHFFFAOYSA-M 0.000 description 1
LTOCMXUTASYUOC-UHFFFAOYSA-M sodium;nonanoate Chemical class [Na+].CCCCCCCCC([O-])=O LTOCMXUTASYUOC-UHFFFAOYSA-M 0.000 description 1
HRQDCDQDOPSGBR-UHFFFAOYSA-M sodium;octane-1-sulfonate Chemical class [Na+].CCCCCCCCS([O-])(=O)=O HRQDCDQDOPSGBR-UHFFFAOYSA-M 0.000 description 1
LHYPLJGBYPAQAK-UHFFFAOYSA-M sodium;pentanoate Chemical class [Na+].CCCCC([O-])=O LHYPLJGBYPAQAK-UHFFFAOYSA-M 0.000 description 1
NPAWNPCNZAPTKA-UHFFFAOYSA-M sodium;propane-1-sulfonate Chemical class [Na+].CCCS([O-])(=O)=O NPAWNPCNZAPTKA-UHFFFAOYSA-M 0.000 description 1
JQIUXBSYPZSDIU-UHFFFAOYSA-N spiro[bicyclo[2.2.2]octane-3,3'-oxetane] Chemical compound C1OCC11C(CC2)CCC2C1 JQIUXBSYPZSDIU-UHFFFAOYSA-N 0.000 description 1
HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 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
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
239000010409 thin film Substances 0.000 description 1
DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 description 1
125000003944 tolyl group Chemical group 0.000 description 1
WLOQLWBIJZDHET-UHFFFAOYSA-N triphenylsulfonium Chemical compound C1=CC=CC=C1[S+](C=1C=CC=CC=1)C1=CC=CC=C1 WLOQLWBIJZDHET-UHFFFAOYSA-N 0.000 description 1
239000012953 triphenylsulfonium Substances 0.000 description 1
WUUHFRRPHJEEKV-UHFFFAOYSA-N tripotassium borate Chemical compound [K+].[K+].[K+].[O-]B([O-])[O-] WUUHFRRPHJEEKV-UHFFFAOYSA-N 0.000 description 1
229960000834 vinyl ether Drugs 0.000 description 1
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
229910052724 xenon Inorganic materials 0.000 description 1
FHNFHKCVQCLJFQ-UHFFFAOYSA-N xenon atom Chemical compound [Xe] FHNFHKCVQCLJFQ-UHFFFAOYSA-N 0.000 description 1