TWI288859B - Sulfonate derivatives and the use thereof as latent acids - Google Patents

Info

Publication number

TWI288859B

TWI288859B TW092102265A TW92102265A TWI288859B TW I288859 B TWI288859 B TW I288859B TW 092102265 A TW092102265 A TW 092102265A TW 92102265 A TW92102265 A TW 92102265A TW I288859 B TWI288859 B TW I288859B

Authority

TW

Taiwan

Prior art keywords

nr21r22

alkyl

group

cycloalkyl

phenyl

Prior art date

2002-02-06

Links

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• 239000002253 acid Substances 0.000 title claims abstract description 206
• 150000007513 acids Chemical class 0.000 title description 4
• 125000001273 sulfonato group Chemical class [O-]S(*)(=O)=O 0.000 title 1
• -1 anthracyl Chemical group 0.000 claims abstract description 489
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 177
• 229920002120 photoresistant polymer Polymers 0.000 claims abstract description 128
• 150000001875 compounds Chemical class 0.000 claims abstract description 118
• 239000000203 mixture Substances 0.000 claims abstract description 113
• 125000001624 naphthyl group Chemical group 0.000 claims abstract description 99
• 239000001257 hydrogen Substances 0.000 claims abstract description 95
• 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 95
• 125000005561 phenanthryl group Chemical group 0.000 claims abstract description 52
• 125000001072 heteroaryl group Chemical group 0.000 claims abstract description 45
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 41
• 230000009471 action Effects 0.000 claims abstract description 33
• 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims abstract description 14
• 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims abstract description 5
• 125000000217 alkyl group Chemical group 0.000 claims description 467
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 287
• 125000001188 haloalkyl group Chemical group 0.000 claims description 217
• 229910052736 halogen Inorganic materials 0.000 claims description 181
• 150000002367 halogens Chemical class 0.000 claims description 176
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 71
• 229920000642 polymer Polymers 0.000 claims description 68
• 125000003545 alkoxy group Chemical group 0.000 claims description 62
• 125000001424 substituent group Chemical group 0.000 claims description 61
• 238000000576 coating method Methods 0.000 claims description 50
• 150000002431 hydrogen Chemical class 0.000 claims description 45
• 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 claims description 43
• 229920005989 resin Polymers 0.000 claims description 43
• 239000011347 resin Substances 0.000 claims description 43
• 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 41
• 239000011248 coating agent Substances 0.000 claims description 40
• 238000000034 method Methods 0.000 claims description 39
• 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 37
• 239000000126 substance Substances 0.000 claims description 32
• 125000004414 alkyl thio group Chemical group 0.000 claims description 31
• 125000003118 aryl group Chemical group 0.000 claims description 31
• HKOOXMFOFWEVGF-UHFFFAOYSA-N phenylhydrazine Chemical group NNC1=CC=CC=C1 HKOOXMFOFWEVGF-UHFFFAOYSA-N 0.000 claims description 31
• 125000003342 alkenyl group Chemical group 0.000 claims description 29
• 125000000392 cycloalkenyl group Chemical group 0.000 claims description 28
• 239000000178 monomer Substances 0.000 claims description 28
• 125000002088 tosyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])S(*)(=O)=O 0.000 claims description 28
• UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 27
• OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 25
• 125000005605 benzo group Chemical group 0.000 claims description 25
• 125000004432 carbon atom Chemical group C* 0.000 claims description 25
• 125000005278 alkyl sulfonyloxy group Chemical group 0.000 claims description 24
• 125000002178 anthracenyl group Chemical group C1(=CC=CC2=CC3=CC=CC=C3C=C12)* 0.000 claims description 24
• 229940067157 phenylhydrazine Drugs 0.000 claims description 24
• 239000000758 substrate Substances 0.000 claims description 23
• 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 22
• 125000006678 phenoxycarbonyl group Chemical group 0.000 claims description 22
• 239000000463 material Substances 0.000 claims description 20
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 19
• 125000003396 thiol group Chemical class [H]S* 0.000 claims description 19
• 125000002947 alkylene group Chemical group 0.000 claims description 18
• 239000004305 biphenyl Substances 0.000 claims description 18
• ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 18
• 235000010290 biphenyl Nutrition 0.000 claims description 17
• 125000006267 biphenyl group Chemical group 0.000 claims description 17
• 239000003795 chemical substances by application Substances 0.000 claims description 17
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 17
• 239000002904 solvent Substances 0.000 claims description 17
• USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical group C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 claims description 16
• 238000004090 dissolution Methods 0.000 claims description 16
• 125000005843 halogen group Chemical group 0.000 claims description 16
• 229910052757 nitrogen Inorganic materials 0.000 claims description 16
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 15
• AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 claims description 14
• 238000004132 cross linking Methods 0.000 claims description 14
• 101150114598 Arl5a gene Proteins 0.000 claims description 13
• 101100379717 Mus musculus Arl4d gene Proteins 0.000 claims description 13
• 150000001335 aliphatic alkanes Chemical class 0.000 claims description 13
• 125000004122 cyclic group Chemical group 0.000 claims description 13
• 239000003112 inhibitor Substances 0.000 claims description 13
• 125000002252 acyl group Chemical group 0.000 claims description 12
• 229910052799 carbon Inorganic materials 0.000 claims description 12
• 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 claims description 12
• 239000000654 additive Substances 0.000 claims description 11
• 239000000853 adhesive Substances 0.000 claims description 11
• 230000001070 adhesive effect Effects 0.000 claims description 11
• 239000000460 chlorine Substances 0.000 claims description 11
• 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 claims description 11
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 10
• 229910052801 chlorine Inorganic materials 0.000 claims description 10
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 10
• 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 claims description 10
• 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 10
• DSSYKIVIOFKYAU-XCBNKYQSSA-N (R)-camphor Chemical compound C1C[C@@]2(C)C(=O)C[C@@H]1C2(C)C DSSYKIVIOFKYAU-XCBNKYQSSA-N 0.000 claims description 9
• 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 9
• 230000004927 fusion Effects 0.000 claims description 8
• 238000007639 printing Methods 0.000 claims description 7
• 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 7
• 125000003944 tolyl group Chemical group 0.000 claims description 7
• 125000003302 alkenyloxy group Chemical group 0.000 claims description 6
• 125000005427 anthranyl group Chemical group 0.000 claims description 6
• 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 6
• 238000006467 substitution reaction Methods 0.000 claims description 6
• 125000006710 (C2-C12) alkenyl group Chemical group 0.000 claims description 5
• 241000723346 Cinnamomum camphora Species 0.000 claims description 5
• 125000004423 acyloxy group Chemical group 0.000 claims description 5
• 229910052794 bromium Inorganic materials 0.000 claims description 5
• 229960000846 camphor Drugs 0.000 claims description 5
• 229930008380 camphor Natural products 0.000 claims description 5
• 239000007789 gas Substances 0.000 claims description 5
• 125000005059 halophenyl group Chemical group 0.000 claims description 5
• 238000004519 manufacturing process Methods 0.000 claims description 5
• 229910052760 oxygen Inorganic materials 0.000 claims description 5
• 239000001301 oxygen Substances 0.000 claims description 5
• 150000003254 radicals Chemical class 0.000 claims description 5
• 229910021653 sulphate ion Inorganic materials 0.000 claims description 5
• 101150010802 CVC2 gene Proteins 0.000 claims description 4
• ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 4
• 241000196324 Embryophyta Species 0.000 claims description 4
• 125000000304 alkynyl group Chemical group 0.000 claims description 4
• MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 claims description 4
• GPAYUJZHTULNBE-UHFFFAOYSA-O diphenylphosphanium Chemical compound C=1C=CC=CC=1[PH2+]C1=CC=CC=C1 GPAYUJZHTULNBE-UHFFFAOYSA-O 0.000 claims description 4
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
• 239000000976 ink Substances 0.000 claims description 4
• 125000005146 naphthylsulfonyl group Chemical group C1(=CC=CC2=CC=CC=C12)S(=O)(=O)* 0.000 claims description 4
• NIHNNTQXNPWCJQ-UHFFFAOYSA-N o-biphenylenemethane Natural products C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 claims description 4
• 125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 4
• 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims description 3
• KEQGZUUPPQEDPF-UHFFFAOYSA-N 1,3-dichloro-5,5-dimethylimidazolidine-2,4-dione Chemical compound CC1(C)N(Cl)C(=O)N(Cl)C1=O KEQGZUUPPQEDPF-UHFFFAOYSA-N 0.000 claims description 3
• 125000006539 C12 alkyl 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 claims description 3
• PJANXHGTPQOBST-VAWYXSNFSA-N Stilbene Natural products C=1C=CC=CC=1/C=C/C1=CC=CC=C1 PJANXHGTPQOBST-VAWYXSNFSA-N 0.000 claims description 3
• QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims description 3
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 3
• 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 3
• 125000002993 cycloalkylene group Chemical group 0.000 claims description 3
• GPAYUJZHTULNBE-UHFFFAOYSA-N diphenylphosphine Chemical compound C=1C=CC=CC=1PC1=CC=CC=C1 GPAYUJZHTULNBE-UHFFFAOYSA-N 0.000 claims description 3
• PJANXHGTPQOBST-UHFFFAOYSA-N stilbene Chemical compound C=1C=CC=CC=1C=CC1=CC=CC=C1 PJANXHGTPQOBST-UHFFFAOYSA-N 0.000 claims description 3
• 235000021286 stilbenes Nutrition 0.000 claims description 3
• 125000006702 (C1-C18) alkyl group Chemical group 0.000 claims description 2
• ICWAQZZLBRUGRU-UHFFFAOYSA-N SON(N)C1=CC=CC=C1 Chemical compound SON(N)C1=CC=CC=C1 ICWAQZZLBRUGRU-UHFFFAOYSA-N 0.000 claims description 2
• 125000004104 aryloxy group Chemical group 0.000 claims description 2
• SRSXLGNVWSONIS-UHFFFAOYSA-M benzenesulfonate Chemical compound [O-]S(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-M 0.000 claims description 2
• 210000004556 brain Anatomy 0.000 claims description 2
• 125000001309 chloro group Chemical group Cl* 0.000 claims description 2
• ZVEZMVFBMOOHAT-UHFFFAOYSA-N nonane-1-thiol Chemical compound CCCCCCCCCS ZVEZMVFBMOOHAT-UHFFFAOYSA-N 0.000 claims description 2
• XSXHWVKGUXMUQE-UHFFFAOYSA-N osmium dioxide Inorganic materials O=[Os]=O XSXHWVKGUXMUQE-UHFFFAOYSA-N 0.000 claims description 2
• SNOOUWRIMMFWNE-UHFFFAOYSA-M sodium;6-[(3,4,5-trimethoxybenzoyl)amino]hexanoate Chemical compound [Na+].COC1=CC(C(=O)NCCCCCC([O-])=O)=CC(OC)=C1OC SNOOUWRIMMFWNE-UHFFFAOYSA-M 0.000 claims description 2
• 241000234282 Allium Species 0.000 claims 16
• 235000002732 Allium cepa var. cepa Nutrition 0.000 claims 16
• 229940045799 anthracyclines and related substance Drugs 0.000 claims 3
• 125000005740 oxycarbonyl group Chemical group [*:1]OC([*:2])=O 0.000 claims 3
• 125000004149 thio group Chemical group *S* 0.000 claims 3
• YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Natural products C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 claims 2
• 229920001076 Cutan Polymers 0.000 claims 2
• 102000016736 Cyclin Human genes 0.000 claims 2
• 108050006400 Cyclin Proteins 0.000 claims 2
• UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 claims 2
• 125000005577 anthracene group Chemical group 0.000 claims 2
• 125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 claims 2
• 229910017048 AsF6 Inorganic materials 0.000 claims 1
• HNUALPPJLMYHDK-UHFFFAOYSA-N C[CH]C Chemical compound C[CH]C HNUALPPJLMYHDK-UHFFFAOYSA-N 0.000 claims 1
• 101100379727 Caenorhabditis elegans arl-5 gene Proteins 0.000 claims 1
• 240000004244 Cucurbita moschata Species 0.000 claims 1
• 235000009854 Cucurbita moschata Nutrition 0.000 claims 1
• 235000009852 Cucurbita pepo Nutrition 0.000 claims 1
• YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical group [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims 1
• 102000005890 Spectrin Human genes 0.000 claims 1
• 108010019965 Spectrin Proteins 0.000 claims 1
• 229940037003 alum Drugs 0.000 claims 1
• 125000000319 biphenyl-4-yl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims 1
• 239000002738 chelating agent Substances 0.000 claims 1
• 229940125810 compound 20 Drugs 0.000 claims 1
• 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims 1
• JAXFJECJQZDFJS-XHEPKHHKSA-N gtpl8555 Chemical compound OC(=O)C[C@H](N)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](C(C)C)C(=O)N1CCC[C@@H]1C(=O)N[C@H](B1O[C@@]2(C)[C@H]3C[C@H](C3(C)C)C[C@H]2O1)CCC1=CC=C(F)C=C1 JAXFJECJQZDFJS-XHEPKHHKSA-N 0.000 claims 1
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 1
• CPRRHERYRRXBRZ-SRVKXCTJSA-N methyl n-[(2s)-1-[[(2s)-1-hydroxy-3-[(3s)-2-oxopyrrolidin-3-yl]propan-2-yl]amino]-4-methyl-1-oxopentan-2-yl]carbamate Chemical compound COC(=O)N[C@@H](CC(C)C)C(=O)N[C@H](CO)C[C@@H]1CCNC1=O CPRRHERYRRXBRZ-SRVKXCTJSA-N 0.000 claims 1
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 1
• JHYBWOJWPAOJDQ-UHFFFAOYSA-N phenoxysulfanyloxybenzene Chemical compound C=1C=CC=CC=1OSOC1=CC=CC=C1 JHYBWOJWPAOJDQ-UHFFFAOYSA-N 0.000 claims 1
• 125000006327 phenyl hydrazinyl group Chemical group [H]N(*)N([H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims 1
• WVDDGKGOMKODPV-ZQBYOMGUSA-N phenyl(114C)methanol Chemical compound O[14CH2]C1=CC=CC=C1 WVDDGKGOMKODPV-ZQBYOMGUSA-N 0.000 claims 1
• 239000003016 pheromone Substances 0.000 claims 1
• 230000001235 sensitizing effect Effects 0.000 claims 1
• 235000020354 squash Nutrition 0.000 claims 1
• 125000004646 sulfenyl group Chemical group S(*)* 0.000 claims 1
• 238000012876 topography Methods 0.000 claims 1
• 125000004957 naphthylene group Chemical group 0.000 abstract 1
• 239000002585 base Substances 0.000 description 65
• PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 49
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• 239000000243 solution Substances 0.000 description 36
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• 239000003513 alkali Substances 0.000 description 27
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 24
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