TW201004934A

TW201004934A - Sulfonium derivatives and the use therof as latent acids

Sulfonium derivatives and the use therof as latent acids Download PDF

Info

Publication number: TW201004934A
Authority: TW; Taiwan
Prior art keywords: group; alkyl; interrupted; nr5r6; acid
Prior art date: 2008-06-12

Application number

TW098119527A

Other languages

English (en)

Chinese (zh)

Inventor

Yuichi Nishimae

Toshikage Asakura

Hitoshi Yamato

Original Assignee

Ciba Holding Inc

Priority date

2008-06-12

Filing date

2009-06-11

Publication date

2010-02-01

2009-06-11 Application filed by Ciba Holding Inc filed Critical Ciba Holding Inc

2010-02-01 Publication of TW201004934A publication Critical patent/TW201004934A/zh

Links

239000002253 acid Substances 0.000 title claims abstract description 203
150000007513 acids Chemical class 0.000 title abstract description 14
RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical class S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 title description 8
229940083123 ganglion-blocking adreneregic sulfonium derivative Drugs 0.000 title 1
-1 camphoryl Chemical group 0.000 claims abstract description 344
150000001875 compounds Chemical class 0.000 claims abstract description 214
229910052736 halogen Inorganic materials 0.000 claims abstract description 44
150000002367 halogens Chemical class 0.000 claims abstract description 42
239000001257 hydrogen Substances 0.000 claims abstract description 42
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 42
125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims abstract description 32
229910052760 oxygen Inorganic materials 0.000 claims abstract description 21
150000002431 hydrogen Chemical class 0.000 claims abstract description 19
125000006710 (C2-C12) alkenyl group Chemical group 0.000 claims abstract description 16
229910052717 sulfur Inorganic materials 0.000 claims abstract description 14
125000000217 alkyl group Chemical group 0.000 claims description 178
229920000642 polymer Polymers 0.000 claims description 173
239000000203 mixture Substances 0.000 claims description 150
OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 72
125000000753 cycloalkyl group Chemical group 0.000 claims description 59
229920002120 photoresistant polymer Polymers 0.000 claims description 58
238000000576 coating method Methods 0.000 claims description 53
238000000034 method Methods 0.000 claims description 48
239000011248 coating agent Substances 0.000 claims description 42
239000000126 substance Substances 0.000 claims description 42
125000001188 haloalkyl group Chemical group 0.000 claims description 41
125000000392 cycloalkenyl group Chemical group 0.000 claims description 35
239000000463 material Substances 0.000 claims description 35
125000001624 naphthyl group Chemical group 0.000 claims description 35
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 34
MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 claims description 32
125000001424 substituent group Chemical group 0.000 claims description 32
229910052799 carbon Inorganic materials 0.000 claims description 28
125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 25
125000003342 alkenyl group Chemical group 0.000 claims description 24
125000001072 heteroaryl group Chemical group 0.000 claims description 24
101100533877 Hypocrea jecorina (strain QM6a) sor8 gene Proteins 0.000 claims description 23
239000000758 substrate Substances 0.000 claims description 21
230000009471 action Effects 0.000 claims description 19
239000004305 biphenyl Substances 0.000 claims description 19
ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 19
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 18
239000002904 solvent Substances 0.000 claims description 18
125000002947 alkylene group Chemical group 0.000 claims description 17
235000010290 biphenyl Nutrition 0.000 claims description 17
UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 claims description 16
239000000654 additive Substances 0.000 claims description 16
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238000004090 dissolution Methods 0.000 claims description 16
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229910052786 argon Inorganic materials 0.000 claims description 15
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UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 14
125000004432 carbon atom Chemical group C* 0.000 claims description 14
238000007639 printing Methods 0.000 claims description 14
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VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 10
125000005278 alkyl sulfonyloxy group Chemical group 0.000 claims description 10
125000004414 alkyl thio group Chemical group 0.000 claims description 10
125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 claims description 10
125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 9
125000005843 halogen group Chemical group 0.000 claims description 9
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 8
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230000001965 increasing effect Effects 0.000 claims description 3
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101150026756 sir1 gene Proteins 0.000 claims description 3
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VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 claims 1
241000196324 Embryophyta Species 0.000 claims 1
ICWAQZZLBRUGRU-UHFFFAOYSA-N SON(N)C1=CC=CC=C1 Chemical compound SON(N)C1=CC=CC=C1 ICWAQZZLBRUGRU-UHFFFAOYSA-N 0.000 claims 1
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KUCISDUQDQAGRU-UHFFFAOYSA-N benzene;azide Chemical compound [N-]=[N+]=[N-].C1=CC=CC=C1 KUCISDUQDQAGRU-UHFFFAOYSA-N 0.000 claims 1
238000003776 cleavage reaction Methods 0.000 claims 1
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HKOOXMFOFWEVGF-UHFFFAOYSA-N phenylhydrazine Chemical compound NNC1=CC=CC=C1 HKOOXMFOFWEVGF-UHFFFAOYSA-N 0.000 claims 1
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238000005708 tetrahydropyranylation reaction Methods 0.000 description 1
ZYSDERHSJJEJDS-UHFFFAOYSA-M tetrakis-decylazanium;hydroxide Chemical compound [OH-].CCCCCCCCCC[N+](CCCCCCCCCC)(CCCCCCCCCC)CCCCCCCCCC ZYSDERHSJJEJDS-UHFFFAOYSA-M 0.000 description 1
PQMJQYONVLIFOV-UHFFFAOYSA-N tetramethylrhodamine ethyl ester(1+) Chemical class CCOC(=O)C1=CC=CC=C1C1=C2C=CC(=[N+](C)C)C=C2OC2=CC(N(C)C)=CC=C21 PQMJQYONVLIFOV-UHFFFAOYSA-N 0.000 description 1
239000003451 thiazide diuretic agent Substances 0.000 description 1
CBDKQYKMCICBOF-UHFFFAOYSA-N thiazoline Chemical compound C1CN=CS1 CBDKQYKMCICBOF-UHFFFAOYSA-N 0.000 description 1
125000005503 thioxanyl group Chemical group 0.000 description 1
HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 description 1
239000004408 titanium dioxide Substances 0.000 description 1
XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 description 1
238000005809 transesterification reaction Methods 0.000 description 1
238000012546 transfer Methods 0.000 description 1
125000005409 triarylsulfonium group Chemical group 0.000 description 1
AYNNSCRYTDRFCP-UHFFFAOYSA-N triazene Chemical compound NN=N AYNNSCRYTDRFCP-UHFFFAOYSA-N 0.000 description 1
125000004306 triazinyl group Chemical group 0.000 description 1
125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 description 1
IVIIAEVMQHEPAY-UHFFFAOYSA-N tridodecyl phosphite Chemical compound CCCCCCCCCCCCOP(OCCCCCCCCCCCC)OCCCCCCCCCCCC IVIIAEVMQHEPAY-UHFFFAOYSA-N 0.000 description 1
WTVXIBRMWGUIMI-UHFFFAOYSA-N trifluoro($l^{1}-oxidanylsulfonyl)methane Chemical group [O]S(=O)(=O)C(F)(F)F WTVXIBRMWGUIMI-UHFFFAOYSA-N 0.000 description 1
CNUJLMSKURPSHE-UHFFFAOYSA-N trioctadecyl phosphite Chemical class CCCCCCCCCCCCCCCCCCOP(OCCCCCCCCCCCCCCCCCC)OCCCCCCCCCCCCCCCCCC CNUJLMSKURPSHE-UHFFFAOYSA-N 0.000 description 1
KQBSGRWMSNFIPG-UHFFFAOYSA-N trioxane Chemical compound C1COOOC1 KQBSGRWMSNFIPG-UHFFFAOYSA-N 0.000 description 1
WLOQLWBIJZDHET-UHFFFAOYSA-N triphenylsulfonium Chemical compound C1=CC=CC=C1[S+](C=1C=CC=CC=1)C1=CC=CC=C1 WLOQLWBIJZDHET-UHFFFAOYSA-N 0.000 description 1
239000012953 triphenylsulfonium Substances 0.000 description 1
LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical class OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
WGKLOLBTFWFKOD-UHFFFAOYSA-N tris(2-nonylphenyl) phosphite Chemical compound CCCCCCCCCC1=CC=CC=C1OP(OC=1C(=CC=CC=1)CCCCCCCCC)OC1=CC=CC=C1CCCCCCCCC WGKLOLBTFWFKOD-UHFFFAOYSA-N 0.000 description 1
238000009281 ultraviolet germicidal irradiation Methods 0.000 description 1
239000002023 wood Substances 0.000 description 1
150000007964 xanthones Chemical class 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
229910052725 zinc Inorganic materials 0.000 description 1
239000011701 zinc Substances 0.000 description 1