TWI692674B - 衍生自降莰二烯和馬來酸酐之聚合物及其用途 - Google Patents
衍生自降莰二烯和馬來酸酐之聚合物及其用途 Download PDFInfo
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- TWI692674B TWI692674B TW105143893A TW105143893A TWI692674B TW I692674 B TWI692674 B TW I692674B TW 105143893 A TW105143893 A TW 105143893A TW 105143893 A TW105143893 A TW 105143893A TW I692674 B TWI692674 B TW I692674B
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- Prior art keywords
- alkyl
- polymer
- general formula
- maleic anhydride
- composition
- Prior art date
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- 229920000642 polymer Polymers 0.000 title claims abstract description 320
- SJYNFBVQFBRSIB-UHFFFAOYSA-N norbornadiene Chemical compound C1=CC2C=CC1C2 SJYNFBVQFBRSIB-UHFFFAOYSA-N 0.000 title claims abstract description 139
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 title claims abstract description 84
- 239000000203 mixture Substances 0.000 claims abstract description 191
- 239000000178 monomer Substances 0.000 claims abstract description 124
- 150000001875 compounds Chemical class 0.000 claims abstract description 37
- PEEHTFAAVSWFBL-UHFFFAOYSA-N Maleimide Chemical compound O=C1NC(=O)C=C1 PEEHTFAAVSWFBL-UHFFFAOYSA-N 0.000 claims abstract description 22
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 110
- 239000001257 hydrogen Substances 0.000 claims description 49
- 229910052739 hydrogen Inorganic materials 0.000 claims description 49
- BQTPKSBXMONSJI-UHFFFAOYSA-N 1-cyclohexylpyrrole-2,5-dione Chemical compound O=C1C=CC(=O)N1C1CCCCC1 BQTPKSBXMONSJI-UHFFFAOYSA-N 0.000 claims description 44
- 150000002431 hydrogen Chemical class 0.000 claims description 33
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 claims description 31
- 239000002904 solvent Substances 0.000 claims description 31
- JFNLZVQOOSMTJK-KNVOCYPGSA-N norbornene Chemical compound C1[C@@H]2CC[C@H]1C=C2 JFNLZVQOOSMTJK-KNVOCYPGSA-N 0.000 claims description 29
- 125000000217 alkyl group Chemical group 0.000 claims description 28
- 125000006545 (C1-C9) alkyl group Chemical group 0.000 claims description 27
- 239000000654 additive Substances 0.000 claims description 24
- 238000000034 method Methods 0.000 claims description 24
- 239000011248 coating agent Substances 0.000 claims description 21
- 238000000576 coating method Methods 0.000 claims description 21
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 20
- 239000003431 cross linking reagent Substances 0.000 claims description 19
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 18
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 18
- 238000007142 ring opening reaction Methods 0.000 claims description 18
- 125000000041 C6-C10 aryl group Chemical group 0.000 claims description 17
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 16
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 13
- 230000005693 optoelectronics Effects 0.000 claims description 13
- 125000004400 (C1-C12) alkyl group Chemical group 0.000 claims description 12
- 239000002318 adhesion promoter Substances 0.000 claims description 12
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 12
- LLHKCFNBLRBOGN-UHFFFAOYSA-N propylene glycol methyl ether acetate Chemical compound COCC(C)OC(C)=O LLHKCFNBLRBOGN-UHFFFAOYSA-N 0.000 claims description 12
- 229910052736 halogen Inorganic materials 0.000 claims description 11
- 150000002367 halogens Chemical class 0.000 claims description 11
- 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 9
- 238000004519 manufacturing process Methods 0.000 claims description 9
- 229920001897 terpolymer Polymers 0.000 claims description 9
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 8
- 125000001181 organosilyl group Chemical group [SiH3]* 0.000 claims description 8
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 7
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 7
- 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 6
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 6
- 239000004094 surface-active agent Substances 0.000 claims description 6
- 125000006763 (C3-C9) cycloalkyl group Chemical group 0.000 claims description 5
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 5
- 230000008569 process Effects 0.000 claims description 5
- 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
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 4
- 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 4
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 4
- 125000001072 heteroaryl group Chemical group 0.000 claims description 4
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 4
- 239000000758 substrate Substances 0.000 claims description 4
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 3
- 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 description 3
- 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 3
- 125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 claims description 3
- 125000000000 cycloalkoxy group Chemical group 0.000 claims description 3
- 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 3
- SEEYREPSKCQBBF-UHFFFAOYSA-N n-methylmaleimide Chemical compound CN1C(=O)C=CC1=O SEEYREPSKCQBBF-UHFFFAOYSA-N 0.000 claims description 3
- 125000004642 (C1-C12) alkoxy group Chemical group 0.000 claims description 2
- 125000006652 (C3-C12) cycloalkyl group Chemical group 0.000 claims description 2
- 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 2
- 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 2
- 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 2
- JNPCNDJVEUEFBO-UHFFFAOYSA-N 1-butylpyrrole-2,5-dione Chemical compound CCCCN1C(=O)C=CC1=O JNPCNDJVEUEFBO-UHFFFAOYSA-N 0.000 claims description 2
- 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 2
- 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 2
- 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 2
- 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 2
- 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 2
- 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 2
- 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 2
- VTWPBVSOSWNXAX-UHFFFAOYSA-N 5-decylbicyclo[2.2.1]hept-2-ene Chemical compound C1C2C(CCCCCCCCCC)CC1C=C2 VTWPBVSOSWNXAX-UHFFFAOYSA-N 0.000 claims description 2
- WMWDGZLDLRCDRG-UHFFFAOYSA-N 5-hexylbicyclo[2.2.1]hept-2-ene Chemical compound C1C2C(CCCCCC)CC1C=C2 WMWDGZLDLRCDRG-UHFFFAOYSA-N 0.000 claims description 2
- GOLQZWYZZWIBCA-UHFFFAOYSA-N 5-octylbicyclo[2.2.1]hept-2-ene Chemical compound C1C2C(CCCCCCCC)CC1C=C2 GOLQZWYZZWIBCA-UHFFFAOYSA-N 0.000 claims description 2
- 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 2
- 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 2
- 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 2
- 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 2
- 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 2
- 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 2
- 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 2
- 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 2
- KVMGTLWDHXMQCT-UHFFFAOYSA-N [N-]=[N+]=[N-].[N-]=[N+]=[N-].S(=O)(=O)=C1C(C=CC(C1)=O)=O Chemical compound [N-]=[N+]=[N-].[N-]=[N+]=[N-].S(=O)(=O)=C1C(C=CC(C1)=O)=O KVMGTLWDHXMQCT-UHFFFAOYSA-N 0.000 claims description 2
- 125000002619 bicyclic group Chemical group 0.000 claims description 2
- 125000005293 bicycloalkoxy group Chemical group 0.000 claims description 2
- 125000005553 heteroaryloxy group Chemical group 0.000 claims description 2
- 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 2
- MXVZVCCKUVRGQC-UHFFFAOYSA-N 3-hexylpyrrole-2,5-dione Chemical compound CCCCCCC1=CC(=O)NC1=O MXVZVCCKUVRGQC-UHFFFAOYSA-N 0.000 claims 1
- IYMZEPRSPLASMS-UHFFFAOYSA-N 3-phenylpyrrole-2,5-dione Chemical compound O=C1NC(=O)C(C=2C=CC=CC=2)=C1 IYMZEPRSPLASMS-UHFFFAOYSA-N 0.000 claims 1
- 125000004104 aryloxy group Chemical group 0.000 claims 1
- 150000001602 bicycloalkyls Chemical group 0.000 claims 1
- 150000001993 dienes Chemical class 0.000 claims 1
- JAGYXYUAYDLKNO-UHFFFAOYSA-N hepta-2,5-diene Chemical compound CC=CCC=CC JAGYXYUAYDLKNO-UHFFFAOYSA-N 0.000 claims 1
- 239000007800 oxidant agent Substances 0.000 claims 1
- 229940124530 sulfonamide Drugs 0.000 claims 1
- 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 1
- 239000003989 dielectric material Substances 0.000 abstract description 6
- 239000012776 electronic material Substances 0.000 abstract description 2
- 229920006029 tetra-polymer Polymers 0.000 abstract 1
- 239000000243 solution Substances 0.000 description 131
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 59
- -1 propyl acetyl Chemical group 0.000 description 58
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 56
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-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
- 238000006243 chemical reaction Methods 0.000 description 34
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 32
- 239000000463 material Substances 0.000 description 30
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 28
- 229910052757 nitrogen Inorganic materials 0.000 description 28
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 28
- 238000003756 stirring Methods 0.000 description 27
- 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
- 235000012431 wafers Nutrition 0.000 description 26
- 230000000052 comparative effect Effects 0.000 description 25
- 238000012512 characterization method Methods 0.000 description 24
- 238000005033 Fourier transform infrared spectroscopy Methods 0.000 description 23
- 238000005227 gel permeation chromatography Methods 0.000 description 23
- 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
- 239000012299 nitrogen atmosphere Substances 0.000 description 22
- 229920001343 polytetrafluoroethylene Polymers 0.000 description 22
- 239000004810 polytetrafluoroethylene Substances 0.000 description 22
- 230000005855 radiation Effects 0.000 description 22
- 238000011161 development Methods 0.000 description 21
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 20
- 0 *C(C1)C2C=CC1C2 Chemical compound *C(C1)C2C=CC1C2 0.000 description 19
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 19
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 18
- 239000004593 Epoxy Substances 0.000 description 18
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 18
- 229920001577 copolymer Polymers 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
- 229920005989 resin Polymers 0.000 description 16
- 239000011347 resin Substances 0.000 description 16
- 239000000126 substance Substances 0.000 description 16
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 15
- 239000002585 base Substances 0.000 description 15
- 239000003795 chemical substances by application Substances 0.000 description 15
- 230000000930 thermomechanical effect Effects 0.000 description 15
- 239000003054 catalyst Substances 0.000 description 14
- 150000002148 esters Chemical class 0.000 description 13
- 238000010438 heat treatment Methods 0.000 description 13
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 12
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 description 12
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 12
- 230000014509 gene expression Effects 0.000 description 12
- 239000011541 reaction mixture Substances 0.000 description 12
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 11
- 239000000356 contaminant Substances 0.000 description 11
- 239000012456 homogeneous solution Substances 0.000 description 11
- 238000003384 imaging method Methods 0.000 description 11
- 239000002245 particle Substances 0.000 description 11
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- 229910052710 silicon Inorganic materials 0.000 description 11
- 239000010703 silicon Substances 0.000 description 11
- LGJCFVYMIJLQJO-UHFFFAOYSA-N 1-dodecylperoxydodecane Chemical compound CCCCCCCCCCCCOOCCCCCCCCCCCC LGJCFVYMIJLQJO-UHFFFAOYSA-N 0.000 description 10
- BGTOWKSIORTVQH-UHFFFAOYSA-N cyclopentanone Chemical compound O=C1CCCC1 BGTOWKSIORTVQH-UHFFFAOYSA-N 0.000 description 10
- 238000001914 filtration Methods 0.000 description 10
- 230000009477 glass transition Effects 0.000 description 10
- 238000004377 microelectronic Methods 0.000 description 10
- 239000001301 oxygen Substances 0.000 description 10
- 229910052760 oxygen Inorganic materials 0.000 description 10
- 239000005977 Ethylene Substances 0.000 description 9
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 9
- 238000004132 cross linking Methods 0.000 description 9
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 9
- 238000005191 phase separation Methods 0.000 description 9
- 125000001424 substituent group Chemical group 0.000 description 9
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 8
- 239000002253 acid Substances 0.000 description 8
- 238000006116 polymerization reaction Methods 0.000 description 8
- 238000002360 preparation method Methods 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
- 230000015572 biosynthetic process Effects 0.000 description 7
- 125000000753 cycloalkyl group Chemical group 0.000 description 7
- 238000004090 dissolution Methods 0.000 description 7
- 229910000040 hydrogen fluoride Inorganic materials 0.000 description 7
- 125000002872 norbornadienyl group Chemical group C12=C(C=C(CC1)C2)* 0.000 description 7
- 230000003287 optical effect Effects 0.000 description 7
- 229920001721 polyimide Polymers 0.000 description 7
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 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
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
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Images
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Landscapes
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- Exposure And Positioning Against Photoresist Photosensitive Materials (AREA)
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| WO2020037236A1 (en) | 2018-08-17 | 2020-02-20 | 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 |
| KR20220069051A (ko) * | 2019-09-26 | 2022-05-26 | 스미또모 베이크라이트 가부시키가이샤 | 폴리머, 감광성 수지 조성물, 수지막, 및 전자 장치 |
| WO2021096591A1 (en) | 2019-11-15 | 2021-05-20 | 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 |
| EP4284854A1 (en) | 2021-02-01 | 2023-12-06 | 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 |
Citations (3)
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| US5569711A (en) * | 1991-09-12 | 1996-10-29 | Mitsui Petrochemical Industries, Ltd. | Cycloolefin resin composition |
| US6165672A (en) * | 1997-11-01 | 2000-12-26 | Hyundai Electronics Industries Co., Ltd. | Maleimide or alicyclic olefin-based monomers, copolymer resin of these monomers and photoresist using the resin |
| US20150252132A1 (en) * | 2014-03-06 | 2015-09-10 | Sumitomo Bakelite Co., Ltd. | Polymer, photosensitive resin composition and electronic device |
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| JPH02146045A (ja) * | 1988-02-17 | 1990-06-05 | Tosoh Corp | フォトレジスト組成物 |
| US5212043A (en) | 1988-02-17 | 1993-05-18 | Tosho Corporation | Photoresist composition comprising a non-aromatic resin having no aromatic structures derived from units of an aliphatic cyclic hydrocarbon and units of maleic anhydride and/or maleimide and a photosensitive agent |
| 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 |
| US6013413A (en) * | 1997-02-28 | 2000-01-11 | Cornell Research Foundation, Inc. | Alicyclic nortricyclene polymers and co-polymers |
| 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 |
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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 |
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2016
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- 2016-12-30 WO PCT/US2016/069375 patent/WO2017117483A1/en not_active Ceased
- 2016-12-30 KR KR1020187018753A patent/KR101930045B1/ko active Active
- 2016-12-30 CN CN201680076530.1A patent/CN108473749B/zh active Active
- 2016-12-30 US US15/394,970 patent/US9834627B2/en active Active
- 2016-12-30 JP JP2018533664A patent/JP6726281B2/ja active Active
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2017
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Also Published As
| Publication number | Publication date |
|---|---|
| US20170190810A1 (en) | 2017-07-06 |
| US9834627B2 (en) | 2017-12-05 |
| KR101930045B1 (ko) | 2018-12-17 |
| JP6726281B2 (ja) | 2020-07-22 |
| US9944730B2 (en) | 2018-04-17 |
| JP2019503415A (ja) | 2019-02-07 |
| KR20180082607A (ko) | 2018-07-18 |
| CN108473749A (zh) | 2018-08-31 |
| US20180044449A1 (en) | 2018-02-15 |
| CN108473749B (zh) | 2019-11-26 |
| TW201740189A (zh) | 2017-11-16 |
| WO2017117483A1 (en) | 2017-07-06 |
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