JP6726281B2 - ノルボルナジエン及び無水マレイン酸由来の重合体並びにその利用 - Google Patents
ノルボルナジエン及び無水マレイン酸由来の重合体並びにその利用 Download PDFInfo
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- JP6726281B2 JP6726281B2 JP2018533664A JP2018533664A JP6726281B2 JP 6726281 B2 JP6726281 B2 JP 6726281B2 JP 2018533664 A JP2018533664 A JP 2018533664A JP 2018533664 A JP2018533664 A JP 2018533664A JP 6726281 B2 JP6726281 B2 JP 6726281B2
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- Prior art keywords
- alkyl
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- maleic anhydride
- polymer
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- 229920000642 polymer Polymers 0.000 title claims description 354
- SJYNFBVQFBRSIB-UHFFFAOYSA-N norbornadiene Chemical compound C1=CC2C=CC1C2 SJYNFBVQFBRSIB-UHFFFAOYSA-N 0.000 title claims description 174
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 title claims description 130
- 239000000203 mixture Substances 0.000 claims description 212
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 187
- 239000000178 monomer Substances 0.000 claims description 164
- 239000001257 hydrogen Substances 0.000 claims description 111
- 229910052739 hydrogen Inorganic materials 0.000 claims description 111
- 150000002431 hydrogen Chemical class 0.000 claims description 86
- 125000000217 alkyl group Chemical group 0.000 claims description 67
- -1 (2- (2-methoxyethoxy) ethoxy) methyl Chemical group 0.000 claims description 60
- 125000006545 (C1-C9) alkyl group Chemical group 0.000 claims description 55
- BQTPKSBXMONSJI-UHFFFAOYSA-N 1-cyclohexylpyrrole-2,5-dione Chemical compound O=C1C=CC(=O)N1C1CCCCC1 BQTPKSBXMONSJI-UHFFFAOYSA-N 0.000 claims description 52
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 46
- 125000000041 C6-C10 aryl group Chemical group 0.000 claims description 44
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 38
- 150000001875 compounds Chemical class 0.000 claims description 38
- 229920001897 terpolymer Polymers 0.000 claims description 38
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 36
- 239000002904 solvent Substances 0.000 claims description 35
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 33
- PEEHTFAAVSWFBL-UHFFFAOYSA-N Maleimide Chemical compound O=C1NC(=O)C=C1 PEEHTFAAVSWFBL-UHFFFAOYSA-N 0.000 claims description 32
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 32
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 claims description 31
- 125000004400 (C1-C12) alkyl group Chemical group 0.000 claims description 27
- 239000000654 additive Substances 0.000 claims description 25
- 239000003431 cross linking reagent Substances 0.000 claims description 25
- HIDBROSJWZYGSZ-UHFFFAOYSA-N 1-phenylpyrrole-2,5-dione Chemical compound O=C1C=CC(=O)N1C1=CC=CC=C1 HIDBROSJWZYGSZ-UHFFFAOYSA-N 0.000 claims description 24
- 229910052736 halogen Inorganic materials 0.000 claims description 19
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 18
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 17
- 150000002367 halogens Chemical class 0.000 claims description 17
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 16
- 239000002585 base Substances 0.000 claims description 16
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 16
- 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 description 15
- 125000003118 aryl group Chemical group 0.000 claims description 15
- 238000010438 heat treatment Methods 0.000 claims description 15
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 claims description 14
- 239000002318 adhesion promoter Substances 0.000 claims description 14
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 14
- 238000000576 coating method Methods 0.000 claims description 13
- LLHKCFNBLRBOGN-UHFFFAOYSA-N propylene glycol methyl ether acetate Chemical compound COCC(C)OC(C)=O LLHKCFNBLRBOGN-UHFFFAOYSA-N 0.000 claims description 13
- 125000006763 (C3-C9) cycloalkyl group Chemical group 0.000 claims description 12
- 239000011248 coating agent Substances 0.000 claims description 12
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 12
- JFNLZVQOOSMTJK-KNVOCYPGSA-N norbornene Chemical compound C1[C@@H]2CC[C@H]1C=C2 JFNLZVQOOSMTJK-KNVOCYPGSA-N 0.000 claims description 12
- 125000001181 organosilyl group Chemical group [SiH3]* 0.000 claims description 12
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 11
- 125000004104 aryloxy group Chemical group 0.000 claims description 10
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 10
- 125000005553 heteroaryloxy group Chemical group 0.000 claims description 10
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 10
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 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
- 125000001072 heteroaryl group Chemical group 0.000 claims description 9
- 229910052799 carbon Inorganic materials 0.000 claims description 7
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 7
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims description 6
- 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 claims description 6
- 125000004423 acyloxy group Chemical group 0.000 claims description 6
- 239000003963 antioxidant agent Substances 0.000 claims description 6
- 125000000000 cycloalkoxy group Chemical group 0.000 claims description 6
- 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 claims description 6
- 239000004094 surface-active agent Substances 0.000 claims description 6
- 125000004642 (C1-C12) alkoxy group Chemical group 0.000 claims description 5
- 125000006652 (C3-C12) cycloalkyl group Chemical group 0.000 claims description 5
- 150000001602 bicycloalkyls Chemical group 0.000 claims description 5
- 239000000758 substrate Substances 0.000 claims description 5
- WXCILQOPRQRIRP-UHFFFAOYSA-N 1-(2-phenylethyl)bicyclo[2.2.1]hepta-2,5-diene Chemical compound C1(=CC=CC=C1)CCC12C=CC(C=C1)C2 WXCILQOPRQRIRP-UHFFFAOYSA-N 0.000 claims description 4
- YDGBGLKCFQULNS-UHFFFAOYSA-N 1-(2-phenylethyl)pyrrole-2,5-dione Chemical compound O=C1C=CC(=O)N1CCC1=CC=CC=C1 YDGBGLKCFQULNS-UHFFFAOYSA-N 0.000 claims description 4
- MKRBAPNEJMFMHU-UHFFFAOYSA-N 1-benzylpyrrole-2,5-dione Chemical compound O=C1C=CC(=O)N1CC1=CC=CC=C1 MKRBAPNEJMFMHU-UHFFFAOYSA-N 0.000 claims description 4
- JNPCNDJVEUEFBO-UHFFFAOYSA-N 1-butylpyrrole-2,5-dione Chemical compound CCCCN1C(=O)C=CC1=O JNPCNDJVEUEFBO-UHFFFAOYSA-N 0.000 claims description 4
- WBBLXRUVUDHWRI-UHFFFAOYSA-N 2-octylbicyclo[2.2.1]hepta-2,5-diene Chemical compound C(CCCCCCC)C=1C2C=CC(C1)C2 WBBLXRUVUDHWRI-UHFFFAOYSA-N 0.000 claims description 4
- QCFMSULWFHOYEH-UHFFFAOYSA-N 3-bicyclo[2.2.1]hepta-2,5-dienylmethanol Chemical compound C1C2C(CO)=CC1C=C2 QCFMSULWFHOYEH-UHFFFAOYSA-N 0.000 claims description 4
- RRPMRBRLPCXFBC-UHFFFAOYSA-N 3-butylbicyclo[2.2.1]hepta-2,5-diene Chemical compound C1C2C(CCCC)=CC1C=C2 RRPMRBRLPCXFBC-UHFFFAOYSA-N 0.000 claims description 4
- JEOYYXQQAYFMQR-UHFFFAOYSA-N 3-hexylbicyclo[2.2.1]hepta-2,5-diene Chemical compound C1C2C(CCCCCC)=CC1C=C2 JEOYYXQQAYFMQR-UHFFFAOYSA-N 0.000 claims description 4
- OGJJVYFQXFXJKU-UHFFFAOYSA-N 3-methylbicyclo[2.2.1]hepta-2,5-diene Chemical compound C1C2C(C)=CC1C=C2 OGJJVYFQXFXJKU-UHFFFAOYSA-N 0.000 claims description 4
- 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 description 4
- 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 description 4
- 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 description 4
- VTWPBVSOSWNXAX-UHFFFAOYSA-N 5-decylbicyclo[2.2.1]hept-2-ene Chemical compound C1C2C(CCCCCCCCCC)CC1C=C2 VTWPBVSOSWNXAX-UHFFFAOYSA-N 0.000 claims description 4
- WMWDGZLDLRCDRG-UHFFFAOYSA-N 5-hexylbicyclo[2.2.1]hept-2-ene Chemical compound C1C2C(CCCCCC)CC1C=C2 WMWDGZLDLRCDRG-UHFFFAOYSA-N 0.000 claims description 4
- GOLQZWYZZWIBCA-UHFFFAOYSA-N 5-octylbicyclo[2.2.1]hept-2-ene Chemical compound C1C2C(CCCCCCCC)CC1C=C2 GOLQZWYZZWIBCA-UHFFFAOYSA-N 0.000 claims description 4
- FWBBSFIFLBYIPZ-UHFFFAOYSA-N C(C)C=1C(OC(C1)=O)=O.C(C)/C=1/C(=O)OC(C1)=O Chemical compound C(C)C=1C(OC(C1)=O)=O.C(C)/C=1/C(=O)OC(C1)=O FWBBSFIFLBYIPZ-UHFFFAOYSA-N 0.000 claims description 4
- VVSFXIWGCFLLNE-UHFFFAOYSA-N C(C)C=1C(OC(C1CC)=O)=O.C(C)/C=1/C(=O)OC(C1CC)=O Chemical compound C(C)C=1C(OC(C1CC)=O)=O.C(C)/C=1/C(=O)OC(C1CC)=O VVSFXIWGCFLLNE-UHFFFAOYSA-N 0.000 claims description 4
- PZWXTAVCHFHUSD-UHFFFAOYSA-N CC1C(NC(C1)=O)=O.CC1=CC(=O)NC1=O Chemical compound CC1C(NC(C1)=O)=O.CC1=CC(=O)NC1=O PZWXTAVCHFHUSD-UHFFFAOYSA-N 0.000 claims description 4
- 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 description 4
- LHBCABZGFKFGJD-UHFFFAOYSA-N CC=1C(OC(C1C(F)(F)F)=O)=O.C/C=1/C(=O)OC(C1C(F)(F)F)=O Chemical compound CC=1C(OC(C1C(F)(F)F)=O)=O.C/C=1/C(=O)OC(C1C(F)(F)F)=O LHBCABZGFKFGJD-UHFFFAOYSA-N 0.000 claims description 4
- 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 description 4
- MXUBCJXBVAVUJK-UHFFFAOYSA-N FC(C=1C(OC(C1)=O)=O)(F)F.FC(/C=1/C(=O)OC(C1)=O)(F)F Chemical compound FC(C=1C(OC(C1)=O)=O)(F)F.FC(/C=1/C(=O)OC(C1)=O)(F)F MXUBCJXBVAVUJK-UHFFFAOYSA-N 0.000 claims description 4
- RJFCRUYLEJTOIA-UHFFFAOYSA-N FC(C=1C(OC(C1C(F)(F)F)=O)=O)(F)F.FC(/C=1/C(=O)OC(C1C(F)(F)F)=O)(F)F Chemical compound FC(C=1C(OC(C1C(F)(F)F)=O)=O)(F)F.FC(/C=1/C(=O)OC(C1C(F)(F)F)=O)(F)F RJFCRUYLEJTOIA-UHFFFAOYSA-N 0.000 claims description 4
- SEEYREPSKCQBBF-UHFFFAOYSA-N n-methylmaleimide Chemical compound CN1C(=O)C=CC1=O SEEYREPSKCQBBF-UHFFFAOYSA-N 0.000 claims description 4
- 125000003518 norbornenyl group Chemical group C12(C=CC(CC1)C2)* 0.000 claims description 4
- OBRQPLUPQGLJLH-UHFFFAOYSA-N tert-butyl bicyclo[2.2.1]hepta-2,5-diene-3-carboxylate Chemical compound C1C2C(C(=O)OC(C)(C)C)=CC1C=C2 OBRQPLUPQGLJLH-UHFFFAOYSA-N 0.000 claims description 4
- WWQJGCNAASZVOR-UHFFFAOYSA-N trimethylsilyl bicyclo[2.2.1]hepta-2,5-diene-3-carboxylate Chemical compound C1C2C(C(=O)O[Si](C)(C)C)=CC1C=C2 WWQJGCNAASZVOR-UHFFFAOYSA-N 0.000 claims description 4
- KVMGTLWDHXMQCT-UHFFFAOYSA-N [N-]=[N+]=[N-].[N-]=[N+]=[N-].S(=O)(=O)=C1C(C=CC(C1)=O)=O Chemical group [N-]=[N+]=[N-].[N-]=[N+]=[N-].S(=O)(=O)=C1C(C=CC(C1)=O)=O KVMGTLWDHXMQCT-UHFFFAOYSA-N 0.000 claims description 3
- 125000003545 alkoxy group Chemical group 0.000 claims description 3
- 125000005439 maleimidyl group Chemical group C1(C=CC(N1*)=O)=O 0.000 claims description 3
- 239000003513 alkali Substances 0.000 claims 1
- 239000000243 solution Substances 0.000 description 120
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 62
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 56
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 46
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 45
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 33
- 238000006243 chemical reaction Methods 0.000 description 32
- 229910052757 nitrogen Inorganic materials 0.000 description 31
- 238000003756 stirring Methods 0.000 description 29
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 28
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 26
- WGTYBPLFGIVFAS-UHFFFAOYSA-M tetramethylammonium hydroxide Chemical compound [OH-].C[N+](C)(C)C WGTYBPLFGIVFAS-UHFFFAOYSA-M 0.000 description 26
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 26
- 230000000052 comparative effect Effects 0.000 description 25
- 239000000463 material Substances 0.000 description 24
- 238000005033 Fourier transform infrared spectroscopy Methods 0.000 description 23
- 238000011161 development Methods 0.000 description 23
- 238000005227 gel permeation chromatography Methods 0.000 description 23
- 230000018109 developmental process Effects 0.000 description 22
- 239000012153 distilled water Substances 0.000 description 22
- 229920001903 high density polyethylene Polymers 0.000 description 22
- 239000004700 high-density polyethylene Substances 0.000 description 22
- 238000000034 method Methods 0.000 description 22
- 239000012299 nitrogen atmosphere Substances 0.000 description 22
- 229920001343 polytetrafluoroethylene Polymers 0.000 description 22
- 239000004810 polytetrafluoroethylene Substances 0.000 description 22
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 20
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 18
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 18
- 239000000126 substance Substances 0.000 description 18
- 230000005855 radiation Effects 0.000 description 17
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 16
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 16
- 239000003795 chemical substances by application Substances 0.000 description 16
- 230000014509 gene expression Effects 0.000 description 16
- 229910052710 silicon Inorganic materials 0.000 description 16
- 239000010703 silicon Substances 0.000 description 16
- 230000000930 thermomechanical effect Effects 0.000 description 15
- 229920001577 copolymer Polymers 0.000 description 14
- 150000002118 epoxides Chemical class 0.000 description 14
- 150000002148 esters Chemical class 0.000 description 14
- 229920005989 resin Polymers 0.000 description 14
- 239000011347 resin Substances 0.000 description 14
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 13
- 230000000996 additive effect Effects 0.000 description 13
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 12
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 12
- 239000011541 reaction mixture Substances 0.000 description 12
- LGJCFVYMIJLQJO-UHFFFAOYSA-N 1-dodecylperoxydodecane Chemical compound CCCCCCCCCCCCOOCCCCCCCCCCCC LGJCFVYMIJLQJO-UHFFFAOYSA-N 0.000 description 11
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 11
- 239000003054 catalyst Substances 0.000 description 11
- 238000011109 contamination Methods 0.000 description 11
- 239000012456 homogeneous solution Substances 0.000 description 11
- 238000004377 microelectronic Methods 0.000 description 11
- 230000005693 optoelectronics Effects 0.000 description 11
- 239000002245 particle Substances 0.000 description 11
- 239000011148 porous material Substances 0.000 description 11
- 239000004593 Epoxy Substances 0.000 description 10
- BGTOWKSIORTVQH-UHFFFAOYSA-N cyclopentanone Chemical compound O=C1CCCC1 BGTOWKSIORTVQH-UHFFFAOYSA-N 0.000 description 10
- 230000009477 glass transition Effects 0.000 description 10
- 239000012528 membrane Substances 0.000 description 10
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 9
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 9
- 239000001301 oxygen Substances 0.000 description 9
- 229910052760 oxygen Inorganic materials 0.000 description 9
- 238000005191 phase separation Methods 0.000 description 9
- 238000007142 ring opening reaction Methods 0.000 description 9
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
- 238000001723 curing Methods 0.000 description 8
- 125000001424 substituent group Chemical group 0.000 description 8
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 description 7
- 239000004642 Polyimide Substances 0.000 description 7
- 206010042602 Supraventricular extrasystoles Diseases 0.000 description 7
- 239000007983 Tris buffer Substances 0.000 description 7
- 239000002253 acid Substances 0.000 description 7
- 238000004458 analytical method Methods 0.000 description 7
- 238000004132 cross linking Methods 0.000 description 7
- 229910000040 hydrogen fluoride Inorganic materials 0.000 description 7
- 229920001721 polyimide Polymers 0.000 description 7
- 238000006116 polymerization reaction Methods 0.000 description 7
- 238000002360 preparation method Methods 0.000 description 7
- 238000002411 thermogravimetry Methods 0.000 description 7
- KBPLFHHGFOOTCA-UHFFFAOYSA-N 1-Octanol Chemical compound CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- 238000004090 dissolution Methods 0.000 description 6
- 125000001183 hydrocarbyl group Chemical group 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- 125000002872 norbornadienyl group Chemical group C12=C(C=C(CC1)C2)* 0.000 description 6
- 229920000647 polyepoxide Polymers 0.000 description 6
- 230000035882 stress Effects 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 5
- 230000015572 biosynthetic process Effects 0.000 description 5
- 239000003822 epoxy resin Substances 0.000 description 5
- 230000032050 esterification Effects 0.000 description 5
- 238000005886 esterification reaction Methods 0.000 description 5
- 238000003384 imaging method Methods 0.000 description 5
- 239000003999 initiator Substances 0.000 description 5
- 238000004519 manufacturing process Methods 0.000 description 5
- 238000005259 measurement Methods 0.000 description 5
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 4
- 238000005481 NMR spectroscopy Methods 0.000 description 4
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 4
- 125000003710 aryl alkyl group Chemical group 0.000 description 4
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Classifications
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- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F232/00—Copolymers of cyclic compounds containing no unsaturated aliphatic radicals in a side chain, and having one or more carbon-to-carbon double bonds in a carbocyclic ring system
- C08F232/02—Copolymers of cyclic compounds containing no unsaturated aliphatic radicals in a side chain, and having one or more carbon-to-carbon double bonds in a carbocyclic ring system having no condensed rings
- C08F232/06—Copolymers of cyclic compounds containing no unsaturated aliphatic radicals in a side chain, and having one or more carbon-to-carbon double bonds in a carbocyclic ring system having no condensed rings having two or more carbon-to-carbon double bonds
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F32/00—Homopolymers and copolymers of cyclic compounds having no unsaturated aliphatic radicals in a side chain, and having one or more carbon-to-carbon double bonds in a carbocyclic ring system
- C08F32/08—Homopolymers and copolymers of cyclic compounds having no unsaturated aliphatic radicals in a side chain, and having one or more carbon-to-carbon double bonds in a carbocyclic ring system having two condensed rings
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L47/00—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, at least one having two or more carbon-to-carbon double bonds; Compositions of derivatives of such polymers
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F2/00—Processes of polymerisation
- C08F2/46—Polymerisation initiated by wave energy or particle radiation
- C08F2/48—Polymerisation initiated by wave energy or particle radiation by ultraviolet or visible light
- C08F2/50—Polymerisation initiated by wave energy or particle radiation by ultraviolet or visible light with sensitising agents
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F22/00—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals each having only one carbon-to-carbon double bond, and at least one being terminated by a carboxyl radical and containing at least one other carboxyl radical in the molecule; Salts, anhydrides, esters, amides, imides or nitriles thereof
- C08F22/04—Anhydrides, e.g. cyclic anhydrides
- C08F22/06—Maleic anhydride
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F232/00—Copolymers of cyclic compounds containing no unsaturated aliphatic radicals in a side chain, and having one or more carbon-to-carbon double bonds in a carbocyclic ring system
- C08F232/08—Copolymers of cyclic compounds containing no unsaturated aliphatic radicals in a side chain, and having one or more carbon-to-carbon double bonds in a carbocyclic ring system having condensed rings
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- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F32/00—Homopolymers and copolymers of cyclic compounds having no unsaturated aliphatic radicals in a side chain, and having one or more carbon-to-carbon double bonds in a carbocyclic ring system
- C08F32/02—Homopolymers and copolymers of cyclic compounds having no unsaturated aliphatic radicals in a side chain, and having one or more carbon-to-carbon double bonds in a carbocyclic ring system having no condensed rings
- C08F32/06—Homopolymers and copolymers of cyclic compounds having no unsaturated aliphatic radicals in a side chain, and having one or more carbon-to-carbon double bonds in a carbocyclic ring system having no condensed rings having two or more carbon-to-carbon double bonds
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L45/00—Compositions of homopolymers or copolymers of compounds having no unsaturated aliphatic radicals in side chain, and having one or more carbon-to-carbon double bonds in a carbocyclic or in a heterocyclic ring system; Compositions of derivatives of such polymers
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- G—PHYSICS
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- 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
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- 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
- G03F7/16—Coating processes; Apparatus therefor
- G03F7/162—Coating on a rotating support, e.g. using a whirler or a spinner
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- G—PHYSICS
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- 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
- G03F7/16—Coating processes; Apparatus therefor
- G03F7/168—Finishing the coated layer, e.g. drying, baking, soaking
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- 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
- G03F7/20—Exposure; Apparatus therefor
- G03F7/2002—Exposure; Apparatus therefor with visible light or UV light, through an original having an opaque pattern on a transparent support, e.g. film printing, projection printing; by reflection of visible or UV light from an original such as a printed image
-
- 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
- G03F7/26—Processing photosensitive materials; Apparatus therefor
- G03F7/30—Imagewise removal using liquid means
- G03F7/32—Liquid compositions therefor, e.g. developers
- G03F7/322—Aqueous alkaline compositions
-
- 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
- G03F7/26—Processing photosensitive materials; Apparatus therefor
- G03F7/40—Treatment after imagewise removal, e.g. baking
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- Chemical & Material Sciences (AREA)
- Physics & Mathematics (AREA)
- Medicinal Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- General Physics & Mathematics (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Exposure And Positioning Against Photoresist Photosensitive Materials (AREA)
- Materials For Photolithography (AREA)
- Compositions Of Macromolecular Compounds (AREA)
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| US201562273553P | 2015-12-31 | 2015-12-31 | |
| US62/273,553 | 2015-12-31 | ||
| PCT/US2016/069375 WO2017117483A1 (en) | 2015-12-31 | 2016-12-30 | Polymers derived from norbornadiene and maleic anhydride and use thereof |
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| JP2019503415A JP2019503415A (ja) | 2019-02-07 |
| JP2019503415A5 JP2019503415A5 (enExample) | 2020-02-20 |
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| TWI692674B (zh) * | 2015-12-31 | 2020-05-01 | 日商住友電木股份有限公司 | 衍生自降莰二烯和馬來酸酐之聚合物及其用途 |
| EP3837266A1 (en) | 2018-08-17 | 2021-06-23 | Massachusetts Institute of Technology | Degradable polymers of a cyclic silyl ether and uses thereof |
| JP7322372B2 (ja) * | 2018-09-28 | 2023-08-08 | 住友ベークライト株式会社 | ポリマー、樹脂組成物、及び、樹脂膜 |
| WO2021060080A1 (ja) * | 2019-09-26 | 2021-04-01 | 住友ベークライト株式会社 | ポリマー、感光性樹脂組成物、樹脂膜、および電子装置 |
| EP4058501A1 (en) | 2019-11-15 | 2022-09-21 | Massachusetts Institute of Technology | Functional oligomers and functional polymers including hydroxylated polymers and conjugates thereof and uses thereof |
| US20210200092A1 (en) * | 2019-12-31 | 2021-07-01 | Taiwan Semiconductor Manufacturing Co., Ltd. | Method of forming photoresist pattern |
| WO2022164503A1 (en) | 2021-02-01 | 2022-08-04 | Massachusetts Institute Of Technology | Reprocessable compositions |
| WO2022256399A2 (en) * | 2021-06-01 | 2022-12-08 | Massachusetts Institute Of Technology | Latent-fluoride containing polymers for triggered degradation |
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| WO1989007786A1 (en) | 1988-02-17 | 1989-08-24 | Tosoh Corporation | Photoresist composition |
| JPH02146045A (ja) * | 1988-02-17 | 1990-06-05 | Tosoh Corp | フォトレジスト組成物 |
| JP2638887B2 (ja) * | 1988-02-26 | 1997-08-06 | 東ソー株式会社 | 感光性組成物 |
| JP2961722B2 (ja) | 1991-12-11 | 1999-10-12 | ジェイエスアール株式会社 | 感放射線性樹脂組成物 |
| JPH0570639A (ja) * | 1991-09-12 | 1993-03-23 | Mitsui Petrochem Ind Ltd | 環状オレフイン樹脂組成物 |
| KR960009295B1 (ko) * | 1991-09-12 | 1996-07-18 | 미쓰이세끼유 가가꾸고오교오 가부시끼가이샤 | 환상올레핀 수지 조성물 |
| US6013413A (en) * | 1997-02-28 | 2000-01-11 | Cornell Research Foundation, Inc. | Alicyclic nortricyclene polymers and co-polymers |
| KR100254472B1 (ko) * | 1997-11-01 | 2000-05-01 | 김영환 | 신규한 말레이미드계 또는 지방족 환형 올레핀계 단량체와 이들 단량체들의 공중합체수지 및 이수지를 이용한 포토레지스트 |
| JP3262108B2 (ja) | 1998-09-09 | 2002-03-04 | 東レ株式会社 | ポジ型感光性樹脂組成物 |
| JP2002201226A (ja) | 2000-12-28 | 2002-07-19 | Jsr Corp | 共重合体およびそれを用いた感放射線性樹脂組成物 |
| JP3952756B2 (ja) | 2001-11-29 | 2007-08-01 | 日本ゼオン株式会社 | 感放射線性樹脂組成物及びその利用 |
| US7799883B2 (en) | 2005-02-22 | 2010-09-21 | Promerus Llc | Norbornene-type polymers, compositions thereof and lithographic process using such compositions |
| JP4684139B2 (ja) * | 2005-10-17 | 2011-05-18 | 信越化学工業株式会社 | レジスト保護膜材料及びパターン形成方法 |
| JP4666166B2 (ja) * | 2005-11-28 | 2011-04-06 | 信越化学工業株式会社 | レジスト下層膜材料及びパターン形成方法 |
| US7745104B2 (en) * | 2006-08-10 | 2010-06-29 | Shin-Etsu Chemical Co., Ltd. | Bottom resist layer composition and patterning process using the same |
| US8541523B2 (en) | 2010-04-05 | 2013-09-24 | Promerus, Llc | Norbornene-type polymers, compositions thereof and lithographic process using such compositions |
| JP5579553B2 (ja) | 2010-09-17 | 2014-08-27 | 信越化学工業株式会社 | レジスト下層膜材料、レジスト下層膜形成方法、パターン形成方法 |
| US8715900B2 (en) | 2011-07-14 | 2014-05-06 | Promerus, Llc | Self-imageable layer forming polymer and compositions thereof |
| TWI554534B (zh) | 2012-09-25 | 2016-10-21 | 住友電木股份有限公司 | 含馬來醯亞胺之環烯烴聚合物及其應用 |
| TWI627217B (zh) | 2013-09-16 | 2018-06-21 | 日商住友電木股份有限公司 | 經胺處理之順丁烯二酸酐聚合物、組成物及其應用 |
| TWI621634B (zh) * | 2013-09-16 | 2018-04-21 | 日商住友電木股份有限公司 | 經胺處理之具有懸垂矽基之順丁烯二酸酐聚合物、組成物及其應用 |
| JP6445525B2 (ja) * | 2014-03-06 | 2018-12-26 | 住友ベークライト株式会社 | ポリマー、感光性樹脂組成物および電子装置 |
| TWI692674B (zh) * | 2015-12-31 | 2020-05-01 | 日商住友電木股份有限公司 | 衍生自降莰二烯和馬來酸酐之聚合物及其用途 |
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| US20180044449A1 (en) | 2018-02-15 |
| US9834627B2 (en) | 2017-12-05 |
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| TW201740189A (zh) | 2017-11-16 |
| CN108473749A (zh) | 2018-08-31 |
| WO2017117483A1 (en) | 2017-07-06 |
| TWI692674B (zh) | 2020-05-01 |
| US20170190810A1 (en) | 2017-07-06 |
| US9944730B2 (en) | 2018-04-17 |
| KR101930045B1 (ko) | 2018-12-17 |
| JP2019503415A (ja) | 2019-02-07 |
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