JP2018538396A5 - - Google Patents

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Publication number

JP2018538396A5

JP2018538396A5 JP2018527885A JP2018527885A JP2018538396A5 JP 2018538396 A5 JP2018538396 A5 JP 2018538396A5 JP 2018527885 A JP2018527885 A JP 2018527885A JP 2018527885 A JP2018527885 A JP 2018527885A JP 2018538396 A5 JP2018538396 A5 JP 2018538396A5

Authority

JP

Japan

Prior art keywords

alkyl

formula

group

composition

hept

Prior art date

2016-11-30

Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)

Granted

Links

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• 239000000203 mixture Substances 0.000 claims 25
• 229910052739 hydrogen Inorganic materials 0.000 claims 9
• 239000001257 hydrogen Substances 0.000 claims 9
• 150000001875 compounds Chemical class 0.000 claims 8
• BEHBBKCBARHMJQ-UHFFFAOYSA-N 5-(2-phenylethyl)bicyclo[2.2.1]hept-2-ene Chemical compound C1C(C=C2)CC2C1CCC1=CC=CC=C1 BEHBBKCBARHMJQ-UHFFFAOYSA-N 0.000 claims 7
• 150000002431 hydrogen Chemical class 0.000 claims 7
• FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical group O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 claims 7
• -1 perfluoro Chemical group 0.000 claims 7
• 229920000642 polymer Polymers 0.000 claims 7
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 6
• 125000000041 C6-C10 aryl group Chemical group 0.000 claims 5
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 5
• 239000000178 monomer Substances 0.000 claims 5
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims 4
• PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims 3
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims 3
• 239000002253 acid Substances 0.000 claims 3
• 125000000217 alkyl group Chemical group 0.000 claims 3
• 239000002585 base Substances 0.000 claims 3
• 229920001577 copolymer Polymers 0.000 claims 3
• 229910052736 halogen Inorganic materials 0.000 claims 3
• 150000002367 halogens Chemical class 0.000 claims 3
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 3
• 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 3
• 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 3
• 229910052757 nitrogen Inorganic materials 0.000 claims 3
• 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 claims 2
• 125000004642 (C1-C12) alkoxy group Chemical group 0.000 claims 2
• 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 2
• 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims 2
• AOBIOSPNXBMOAT-UHFFFAOYSA-N 2-[2-(oxiran-2-ylmethoxy)ethoxymethyl]oxirane Chemical compound C1OC1COCCOCC1CO1 AOBIOSPNXBMOAT-UHFFFAOYSA-N 0.000 claims 2
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 2
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 2
• LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims 2
• SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 claims 2
• 125000004104 aryloxy group Chemical group 0.000 claims 2
• 239000011248 coating agent Substances 0.000 claims 2
• 238000000576 coating method Methods 0.000 claims 2
• 125000000000 cycloalkoxy group Chemical group 0.000 claims 2
• 239000003822 epoxy resin Substances 0.000 claims 2
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 2
• 125000004433 nitrogen atom Chemical group N* 0.000 claims 2
• 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 claims 2
• 229920000647 polyepoxide Polymers 0.000 claims 2
• 229920001451 polypropylene glycol Polymers 0.000 claims 2
• LLHKCFNBLRBOGN-UHFFFAOYSA-N propylene glycol methyl ether acetate Chemical compound COCC(C)OC(C)=O LLHKCFNBLRBOGN-UHFFFAOYSA-N 0.000 claims 2
• 239000002904 solvent Substances 0.000 claims 2
• LWHOMMCIJIJIGV-UHFFFAOYSA-N (1,3-dioxobenzo[de]isoquinolin-2-yl) trifluoromethanesulfonate Chemical compound C1=CC(C(N(OS(=O)(=O)C(F)(F)F)C2=O)=O)=C3C2=CC=CC3=C1 LWHOMMCIJIJIGV-UHFFFAOYSA-N 0.000 claims 1
• 125000004400 (C1-C12) alkyl group Chemical group 0.000 claims 1
• 125000006652 (C3-C12) cycloalkyl group Chemical group 0.000 claims 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 claims 1
• GEWWCWZGHNIUBW-UHFFFAOYSA-N 1-(4-nitrophenyl)propan-2-one Chemical compound CC(=O)CC1=CC=C([N+]([O-])=O)C=C1 GEWWCWZGHNIUBW-UHFFFAOYSA-N 0.000 claims 1
• UDHAWRUAECEBHC-UHFFFAOYSA-N 1-iodo-4-methylbenzene Chemical compound CC1=CC=C(I)C=C1 UDHAWRUAECEBHC-UHFFFAOYSA-N 0.000 claims 1
• KUBDPQJOLOUJRM-UHFFFAOYSA-N 2-(chloromethyl)oxirane;4-[2-(4-hydroxyphenyl)propan-2-yl]phenol Chemical compound ClCC1CO1.C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 KUBDPQJOLOUJRM-UHFFFAOYSA-N 0.000 claims 1
• PUBNJSZGANKUGX-UHFFFAOYSA-N 2-(dimethylamino)-2-[(4-methylphenyl)methyl]-1-(4-morpholin-4-ylphenyl)butan-1-one Chemical compound C=1C=C(N2CCOCC2)C=CC=1C(=O)C(CC)(N(C)C)CC1=CC=C(C)C=C1 PUBNJSZGANKUGX-UHFFFAOYSA-N 0.000 claims 1
• UHFFVFAKEGKNAQ-UHFFFAOYSA-N 2-benzyl-2-(dimethylamino)-1-(4-morpholin-4-ylphenyl)butan-1-one Chemical group C=1C=C(N2CCOCC2)C=CC=1C(=O)C(CC)(N(C)C)CC1=CC=CC=C1 UHFFVFAKEGKNAQ-UHFFFAOYSA-N 0.000 claims 1
• MECNWXGGNCJFQJ-UHFFFAOYSA-N 3-piperidin-1-ylpropane-1,2-diol Chemical compound OCC(O)CN1CCCCC1 MECNWXGGNCJFQJ-UHFFFAOYSA-N 0.000 claims 1
• QHPQWRBYOIRBIT-UHFFFAOYSA-N 4-tert-butylphenol Chemical compound CC(C)(C)C1=CC=C(O)C=C1 QHPQWRBYOIRBIT-UHFFFAOYSA-N 0.000 claims 1
• VCOXSVQMANZZDY-UHFFFAOYSA-N 5-[2-(2-methoxyethoxy)ethoxymethyl]bicyclo[2.2.1]hept-2-ene Chemical compound C1C2C(COCCOCCOC)CC1C=C2 VCOXSVQMANZZDY-UHFFFAOYSA-N 0.000 claims 1
• AAVXIUYWYBDQHZ-UHFFFAOYSA-N 5-[2-[2-(2-methoxyethoxy)ethoxy]ethoxymethyl]bicyclo[2.2.1]hept-2-ene Chemical compound C1C2C(COCCOCCOCCOC)CC1C=C2 AAVXIUYWYBDQHZ-UHFFFAOYSA-N 0.000 claims 1
• UDOJACSDSIHAAT-UHFFFAOYSA-N 5-benzylbicyclo[2.2.1]hept-2-ene Chemical compound C1C(C=C2)CC2C1CC1=CC=CC=C1 UDOJACSDSIHAAT-UHFFFAOYSA-N 0.000 claims 1
• VTWPBVSOSWNXAX-UHFFFAOYSA-N 5-decylbicyclo[2.2.1]hept-2-ene Chemical compound C1C2C(CCCCCCCCCC)CC1C=C2 VTWPBVSOSWNXAX-UHFFFAOYSA-N 0.000 claims 1
• WMWDGZLDLRCDRG-UHFFFAOYSA-N 5-hexylbicyclo[2.2.1]hept-2-ene Chemical group C1C2C(CCCCCC)CC1C=C2 WMWDGZLDLRCDRG-UHFFFAOYSA-N 0.000 claims 1
• GOLQZWYZZWIBCA-UHFFFAOYSA-N 5-octylbicyclo[2.2.1]hept-2-ene Chemical compound C1C2C(CCCCCCCC)CC1C=C2 GOLQZWYZZWIBCA-UHFFFAOYSA-N 0.000 claims 1
• KYLPQLWKHHJEAR-UHFFFAOYSA-N CC=1C(OC(C1)=O)=O.C/C=1/C(=O)OC(C1)=O Chemical compound CC=1C(OC(C1)=O)=O.C/C=1/C(=O)OC(C1)=O KYLPQLWKHHJEAR-UHFFFAOYSA-N 0.000 claims 1
• WLWGMIVKTGHSKH-UHFFFAOYSA-N CC=1C(OC(C1C)=O)=O.C/C=1/C(=O)OC(C1C)=O Chemical compound CC=1C(OC(C1C)=O)=O.C/C=1/C(=O)OC(C1C)=O WLWGMIVKTGHSKH-UHFFFAOYSA-N 0.000 claims 1
• BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 claims 1
• XJPULZCCXIUSHH-UHFFFAOYSA-N FC(S(=O)(=O)[C-](S(=O)(=O)C(F)(F)F)S(=O)(=O)C(F)(F)F)(F)F.C(C)(=O)C1=CC=C(C=C1)SC1=CC=C(C=C1)[S+](C1CCC(CC1)SC1=CC=CC=C1)C1=CC=C(C=C1)SC1=CC=C(C=C1)C(C)=O Chemical compound FC(S(=O)(=O)[C-](S(=O)(=O)C(F)(F)F)S(=O)(=O)C(F)(F)F)(F)F.C(C)(=O)C1=CC=C(C=C1)SC1=CC=C(C=C1)[S+](C1CCC(CC1)SC1=CC=CC=C1)C1=CC=C(C=C1)SC1=CC=C(C=C1)C(C)=O XJPULZCCXIUSHH-UHFFFAOYSA-N 0.000 claims 1
• 239000002202 Polyethylene glycol Substances 0.000 claims 1
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims 1
• SJWNMXYJLKDWOG-UHFFFAOYSA-N [2-(4-methoxynaphthalen-1-yl)-2-oxoethyl]-dimethylsulfanium Chemical compound C1=CC=C2C(OC)=CC=C(C(=O)C[S+](C)C)C2=C1 SJWNMXYJLKDWOG-UHFFFAOYSA-N 0.000 claims 1
• 125000004423 acyloxy group Chemical group 0.000 claims 1
• 239000000654 additive Substances 0.000 claims 1
• 230000000996 additive effect Effects 0.000 claims 1
• 239000002318 adhesion promoter Substances 0.000 claims 1
• 239000003513 alkali Substances 0.000 claims 1
• 125000003545 alkoxy group Chemical group 0.000 claims 1
• 239000003963 antioxidant agent Substances 0.000 claims 1
• 125000002619 bicyclic group Chemical group 0.000 claims 1
• 150000001602 bicycloalkyls Chemical group 0.000 claims 1
• XUCHXOAWJMEFLF-UHFFFAOYSA-N bisphenol F diglycidyl ether Chemical compound C1OC1COC(C=C1)=CC=C1CC(C=C1)=CC=C1OCC1CO1 XUCHXOAWJMEFLF-UHFFFAOYSA-N 0.000 claims 1
• GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical compound C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 claims 1
• 150000002118 epoxides Chemical class 0.000 claims 1
• CQXUNKLAPFJGBF-UHFFFAOYSA-N ethyl 4h-pyrimidine-3-carboxylate Chemical compound CCOC(=O)N1CC=CN=C1 CQXUNKLAPFJGBF-UHFFFAOYSA-N 0.000 claims 1
• 238000010438 heat treatment Methods 0.000 claims 1
• 125000001072 heteroaryl group Chemical group 0.000 claims 1
• 125000005553 heteroaryloxy group Chemical group 0.000 claims 1
• 125000005842 heteroatom Chemical group 0.000 claims 1
• 238000000034 method Methods 0.000 claims 1
• 238000004377 microelectronic Methods 0.000 claims 1
• 125000002950 monocyclic group Chemical group 0.000 claims 1
• 230000005693 optoelectronics Effects 0.000 claims 1
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 1
• 229920001223 polyethylene glycol Polymers 0.000 claims 1
• 125000000714 pyrimidinyl group Chemical group 0.000 claims 1
• 239000000758 substrate Substances 0.000 claims 1
• 239000004094 surface-active agent Substances 0.000 claims 1
• 0 *C(C(O1)=O)=C(*)C1=O Chemical compound *C(C(O1)=O)=C(*)C1=O 0.000 description 10
• PXVIZSSPQARPSP-UHFFFAOYSA-N CCC(CC)C(CC1)[NH]=C(NC2)N1CC2C1C(CC)C1 Chemical compound CCC(CC)C(CC1)[NH]=C(NC2)N1CC2C1C(CC)C1 PXVIZSSPQARPSP-UHFFFAOYSA-N 0.000 description 1
• PPYCXXSOUPZUTG-UHFFFAOYSA-N CCC(CC)c1cc(C(c2cccc(C(C)C(O)OC(C)C3CC3)c2)=O)ccc1 Chemical compound CCC(CC)c1cc(C(c2cccc(C(C)C(O)OC(C)C3CC3)c2)=O)ccc1 PPYCXXSOUPZUTG-UHFFFAOYSA-N 0.000 description 1