JP2021178956A - フッ素化アミド化合物、フッ素化含窒素複素環含有化合物およびフッ素化化合物 - Google Patents
フッ素化アミド化合物、フッ素化含窒素複素環含有化合物およびフッ素化化合物 Download PDFInfo
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- JP2021178956A JP2021178956A JP2021080688A JP2021080688A JP2021178956A JP 2021178956 A JP2021178956 A JP 2021178956A JP 2021080688 A JP2021080688 A JP 2021080688A JP 2021080688 A JP2021080688 A JP 2021080688A JP 2021178956 A JP2021178956 A JP 2021178956A
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- -1 amide compound Chemical class 0.000 title claims abstract description 230
- 150000001875 compounds Chemical class 0.000 title claims description 135
- 125000000962 organic group Chemical group 0.000 claims description 53
- 125000001424 substituent group Chemical group 0.000 claims description 39
- 238000006116 polymerization reaction Methods 0.000 claims description 26
- 125000003118 aryl group Chemical group 0.000 claims description 17
- 125000000623 heterocyclic group Chemical group 0.000 claims description 16
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 16
- 125000003545 alkoxy group Chemical group 0.000 claims description 14
- 125000005843 halogen group Chemical group 0.000 claims description 13
- 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 claims description 11
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical group C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 claims description 3
- 239000000758 substrate Substances 0.000 claims description 2
- 125000001183 hydrocarbyl group Chemical group 0.000 claims 1
- 125000005462 imide group Chemical group 0.000 claims 1
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 134
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 111
- 239000000243 solution Substances 0.000 description 73
- 229910052757 nitrogen Inorganic materials 0.000 description 58
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 56
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 51
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 50
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 45
- 238000002411 thermogravimetry Methods 0.000 description 41
- 239000002904 solvent Substances 0.000 description 35
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 33
- 238000006243 chemical reaction Methods 0.000 description 30
- 239000000203 mixture Substances 0.000 description 29
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 27
- 230000004580 weight loss Effects 0.000 description 26
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 25
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 25
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 24
- SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 24
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 18
- 238000003756 stirring Methods 0.000 description 18
- 238000005033 Fourier transform infrared spectroscopy Methods 0.000 description 16
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 16
- 238000000113 differential scanning calorimetry Methods 0.000 description 16
- 238000005227 gel permeation chromatography Methods 0.000 description 16
- 238000005160 1H NMR spectroscopy Methods 0.000 description 15
- 230000009477 glass transition Effects 0.000 description 15
- 238000003763 carbonization Methods 0.000 description 13
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 13
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 12
- 238000005481 NMR spectroscopy Methods 0.000 description 12
- 238000009826 distribution Methods 0.000 description 12
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 12
- 239000000047 product Substances 0.000 description 12
- 238000002834 transmittance Methods 0.000 description 12
- 0 *c1ccc(*)cc1 Chemical compound *c1ccc(*)cc1 0.000 description 11
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 11
- 239000012043 crude product Substances 0.000 description 11
- 239000012153 distilled water Substances 0.000 description 11
- 150000002430 hydrocarbons Chemical group 0.000 description 11
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 11
- SRDQTCUHAMDAMG-UHFFFAOYSA-N 1,1,2,2,3,3,4,4,5,5,6,6,7,7,8,8-hexadecafluoro-1,8-diiodooctane Chemical compound FC(F)(I)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)I SRDQTCUHAMDAMG-UHFFFAOYSA-N 0.000 description 9
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 9
- 238000010438 heat treatment Methods 0.000 description 9
- 150000003949 imides Chemical group 0.000 description 9
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 9
- 239000000843 powder Substances 0.000 description 9
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 description 8
- GTDPSWPPOUPBNX-UHFFFAOYSA-N ac1mqpva Chemical compound CC12C(=O)OC(=O)C1(C)C1(C)C2(C)C(=O)OC1=O GTDPSWPPOUPBNX-UHFFFAOYSA-N 0.000 description 8
- 125000000217 alkyl group Chemical group 0.000 description 8
- 125000004432 carbon atom Chemical group C* 0.000 description 8
- 238000000921 elemental analysis Methods 0.000 description 8
- APXJLYIVOFARRM-UHFFFAOYSA-N 4-[2-(3,4-dicarboxyphenyl)-1,1,1,3,3,3-hexafluoropropan-2-yl]phthalic acid Chemical compound C1=C(C(O)=O)C(C(=O)O)=CC=C1C(C(F)(F)F)(C(F)(F)F)C1=CC=C(C(O)=O)C(C(O)=O)=C1 APXJLYIVOFARRM-UHFFFAOYSA-N 0.000 description 7
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 7
- 239000011521 glass Substances 0.000 description 7
- 238000004519 manufacturing process Methods 0.000 description 7
- 239000000463 material Substances 0.000 description 7
- 238000000034 method Methods 0.000 description 7
- FDRPZJWMPZUHBN-UHFFFAOYSA-N triazin-2-ium;chloride Chemical class Cl.C1=CN=NN=C1 FDRPZJWMPZUHBN-UHFFFAOYSA-N 0.000 description 7
- CYSGHNMQYZDMIA-UHFFFAOYSA-N 1,3-Dimethyl-2-imidazolidinon Chemical compound CN1CCN(C)C1=O CYSGHNMQYZDMIA-UHFFFAOYSA-N 0.000 description 6
- NVKGJHAQGWCWDI-UHFFFAOYSA-N 4-[4-amino-2-(trifluoromethyl)phenyl]-3-(trifluoromethyl)aniline Chemical compound FC(F)(F)C1=CC(N)=CC=C1C1=CC=C(N)C=C1C(F)(F)F NVKGJHAQGWCWDI-UHFFFAOYSA-N 0.000 description 6
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 6
- 125000001153 fluoro group Chemical group F* 0.000 description 6
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 6
- 239000004793 Polystyrene Substances 0.000 description 5
- 125000002947 alkylene group Chemical group 0.000 description 5
- 239000012298 atmosphere Substances 0.000 description 5
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical group C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 5
- 229910052731 fluorine Inorganic materials 0.000 description 5
- 238000005259 measurement Methods 0.000 description 5
- 229920002223 polystyrene Polymers 0.000 description 5
- 238000000967 suction filtration Methods 0.000 description 5
- 238000005292 vacuum distillation Methods 0.000 description 5
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 4
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 4
- 235000002597 Solanum melongena Nutrition 0.000 description 4
- WKDNYTOXBCRNPV-UHFFFAOYSA-N bpda Chemical compound C1=C2C(=O)OC(=O)C2=CC(C=2C=C3C(=O)OC(C3=CC=2)=O)=C1 WKDNYTOXBCRNPV-UHFFFAOYSA-N 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- 230000018044 dehydration Effects 0.000 description 4
- 238000006297 dehydration reaction Methods 0.000 description 4
- 150000005690 diesters Chemical class 0.000 description 4
- 238000002474 experimental method Methods 0.000 description 4
- 230000002140 halogenating effect Effects 0.000 description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 4
- KWGKDLIKAYFUFQ-UHFFFAOYSA-M lithium chloride Chemical compound [Li+].[Cl-] KWGKDLIKAYFUFQ-UHFFFAOYSA-M 0.000 description 4
- 238000002844 melting Methods 0.000 description 4
- 230000008018 melting Effects 0.000 description 4
- 230000000379 polymerizing effect Effects 0.000 description 4
- 238000007363 ring formation reaction Methods 0.000 description 4
- 150000003462 sulfoxides Chemical class 0.000 description 4
- JOQDDLBOAIKFQX-UHFFFAOYSA-N 1,1,2,2,3,3,4,4,5,5,6,6-dodecafluoro-1,6-diiodohexane Chemical compound FC(F)(I)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)I JOQDDLBOAIKFQX-UHFFFAOYSA-N 0.000 description 3
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000000654 additive Substances 0.000 description 3
- 125000002029 aromatic hydrocarbon group Chemical group 0.000 description 3
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 description 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 239000004305 biphenyl Chemical group 0.000 description 3
- 235000010290 biphenyl Nutrition 0.000 description 3
- 125000006367 bivalent amino carbonyl group Chemical group [H]N([*:1])C([*:2])=O 0.000 description 3
- 229910052799 carbon Inorganic materials 0.000 description 3
- 150000001721 carbon Chemical group 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
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- 125000002950 monocyclic group Chemical group 0.000 description 3
- 238000000465 moulding Methods 0.000 description 3
- 239000002243 precursor Substances 0.000 description 3
- 230000035484 reaction time Effects 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- NAWXUBYGYWOOIX-SFHVURJKSA-N (2s)-2-[[4-[2-(2,4-diaminoquinazolin-6-yl)ethyl]benzoyl]amino]-4-methylidenepentanedioic acid Chemical compound C1=CC2=NC(N)=NC(N)=C2C=C1CCC1=CC=C(C(=O)N[C@@H](CC(=C)C(O)=O)C(O)=O)C=C1 NAWXUBYGYWOOIX-SFHVURJKSA-N 0.000 description 2
- YZBBUYKPTHDZHF-KNVGNIICSA-N (3R)-7,2'-dihydroxy-4'-methoxyisoflavanol Chemical compound OC1=CC(OC)=CC=C1[C@H]1C(O)C2=CC=C(O)C=C2OC1 YZBBUYKPTHDZHF-KNVGNIICSA-N 0.000 description 2
- VLVCDUSVTXIWGW-UHFFFAOYSA-N 4-iodoaniline Chemical compound NC1=CC=C(I)C=C1 VLVCDUSVTXIWGW-UHFFFAOYSA-N 0.000 description 2
- WMWOMMJQVXRFAP-UHFFFAOYSA-N 5-chloro-4,6-dimethoxytriazine Chemical compound COC1=NN=NC(OC)=C1Cl WMWOMMJQVXRFAP-UHFFFAOYSA-N 0.000 description 2
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 2
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- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 2
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- AMXOYNBUYSYVKV-UHFFFAOYSA-M lithium bromide Chemical compound [Li+].[Br-] AMXOYNBUYSYVKV-UHFFFAOYSA-M 0.000 description 2
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- YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 description 1
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- FFCSRWGYGMRBGD-UHFFFAOYSA-N 3-iodoaniline Chemical compound NC1=CC=CC(I)=C1 FFCSRWGYGMRBGD-UHFFFAOYSA-N 0.000 description 1
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- MXNBXEFODBPXBQ-UHFFFAOYSA-N Cc(cc1)ccc1N(C(c1ccccc11)=O)C1=O Chemical compound Cc(cc1)ccc1N(C(c1ccccc11)=O)C1=O MXNBXEFODBPXBQ-UHFFFAOYSA-N 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
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- GTGBOBFVMZPKJQ-UHFFFAOYSA-N NC1=CC=C(C(C(C(C(C(C(C(C(C(C=C2)=CC=C2N)(F)F)(F)F)(F)F)(F)F)(F)F)(F)F)(F)F)(F)F)C=C1 Chemical compound NC1=CC=C(C(C(C(C(C(C(C(C(C(C=C2)=CC=C2N)(F)F)(F)F)(F)F)(F)F)(F)F)(F)F)(F)F)(F)F)C=C1 GTGBOBFVMZPKJQ-UHFFFAOYSA-N 0.000 description 1
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- TXVHTIQJNYSSKO-UHFFFAOYSA-N benzo[e]pyrene Chemical group C1=CC=C2C3=CC=CC=C3C3=CC=CC4=CC=C1C2=C34 TXVHTIQJNYSSKO-UHFFFAOYSA-N 0.000 description 1
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- DDTBPAQBQHZRDW-UHFFFAOYSA-N cyclododecane Chemical group C1CCCCCCCCCCC1 DDTBPAQBQHZRDW-UHFFFAOYSA-N 0.000 description 1
- 125000001162 cycloheptenyl group Chemical group C1(=CCCCCC1)* 0.000 description 1
- 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 description 1
- 125000000596 cyclohexenyl group Chemical group C1(=CCCCC1)* 0.000 description 1
- 125000004113 cyclononanyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 125000000522 cyclooctenyl group Chemical group C1(=CCCCCCC1)* 0.000 description 1
- 125000000640 cyclooctyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- KYTNZWVKKKJXFS-UHFFFAOYSA-N cycloundecane Chemical group C1CCCCCCCCCC1 KYTNZWVKKKJXFS-UHFFFAOYSA-N 0.000 description 1
- 125000004855 decalinyl group Chemical group C1(CCCC2CCCCC12)* 0.000 description 1
- 239000003989 dielectric material Substances 0.000 description 1
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical group C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 1
- 125000006840 diphenylmethane group Chemical group 0.000 description 1
- 238000005401 electroluminescence Methods 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- 125000004185 ester group Chemical group 0.000 description 1
- 238000005530 etching Methods 0.000 description 1
- 239000004210 ether based solvent Substances 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- 238000001125 extrusion Methods 0.000 description 1
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 239000012210 heat-resistant fiber Substances 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 239000011810 insulating material Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 239000004973 liquid crystal related substance Substances 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 125000000896 monocarboxylic acid group Chemical group 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 125000002872 norbornadienyl group Chemical group C12=C(C=C(CC1)C2)* 0.000 description 1
- 125000003518 norbornenyl group Chemical group C12(C=CC(CC1)C2)* 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 125000005582 pentacene group Chemical group 0.000 description 1
- 230000002093 peripheral effect Effects 0.000 description 1
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 1
- YNPNZTXNASCQKK-UHFFFAOYSA-N phenanthrene Chemical group C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 description 1
- UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 1
- FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 description 1
- 238000009832 plasma treatment Methods 0.000 description 1
- 229920002480 polybenzimidazole Polymers 0.000 description 1
- 229920000867 polyelectrolyte Polymers 0.000 description 1
- 239000002861 polymer material Substances 0.000 description 1
- 239000011253 protective coating Substances 0.000 description 1
- 125000005581 pyrene group Chemical group 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 235000009566 rice Nutrition 0.000 description 1
- 238000005488 sandblasting Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- PHICBFWUYUCFKS-UHFFFAOYSA-N spiro[4.4]nonane Chemical group C1CCCC21CCCC2 PHICBFWUYUCFKS-UHFFFAOYSA-N 0.000 description 1
- 238000000859 sublimation Methods 0.000 description 1
- 230000008022 sublimation Effects 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 150000003457 sulfones Chemical group 0.000 description 1
- 238000009864 tensile test Methods 0.000 description 1
- 125000005579 tetracene group Chemical group 0.000 description 1
- 125000004306 triazinyl group Chemical group 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- 125000005580 triphenylene group Chemical group 0.000 description 1
- 238000000870 ultraviolet spectroscopy Methods 0.000 description 1
- 239000002966 varnish Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C63/00—Compounds having carboxyl groups bound to a carbon atoms of six-membered aromatic rings
- C07C63/68—Compounds having carboxyl groups bound to a carbon atoms of six-membered aromatic rings containing halogen
- C07C63/72—Polycyclic acids
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- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
- C08G73/06—Polycondensates having nitrogen-containing heterocyclic rings in the main chain of the macromolecule
- C08G73/10—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
- C08G73/1067—Wholly aromatic polyimides, i.e. having both tetracarboxylic and diamino moieties aromatically bound
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- C07C211/43—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
- C07C211/44—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to only one six-membered aromatic ring
- C07C211/52—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to only one six-membered aromatic ring the carbon skeleton being further substituted by halogen atoms or by nitro or nitroso groups
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
- C07C233/64—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings
- C07C233/77—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by amino groups
- C07C233/80—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by amino groups with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by a carbon atom of a six-membered aromatic ring
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D251/00—Heterocyclic compounds containing 1,3,5-triazine rings
- C07D251/02—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings
- C07D251/12—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D251/26—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with only hetero atoms directly attached to ring carbon atoms
- C07D251/30—Only oxygen atoms
- C07D251/34—Cyanuric or isocyanuric esters
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- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G69/00—Macromolecular compounds obtained by reactions forming a carboxylic amide link in the main chain of the macromolecule
- C08G69/02—Polyamides derived from amino-carboxylic acids or from polyamines and polycarboxylic acids
- C08G69/26—Polyamides derived from amino-carboxylic acids or from polyamines and polycarboxylic acids derived from polyamines and polycarboxylic acids
- C08G69/32—Polyamides derived from amino-carboxylic acids or from polyamines and polycarboxylic acids derived from polyamines and polycarboxylic acids from aromatic diamines and aromatic dicarboxylic acids with both amino and carboxylic groups aromatically bound
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- C08G69/00—Macromolecular compounds obtained by reactions forming a carboxylic amide link in the main chain of the macromolecule
- C08G69/42—Polyamides containing atoms other than carbon, hydrogen, oxygen, and nitrogen
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- C08G73/06—Polycondensates having nitrogen-containing heterocyclic rings in the main chain of the macromolecule
- C08G73/10—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
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- C08G73/06—Polycondensates having nitrogen-containing heterocyclic rings in the main chain of the macromolecule
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Abstract
Description
また、本開示では誘電率が低く、かつ、誘電損失が低いフッ素化含窒素複素環含有化合物を提供することを目的とする。
また、本開示では新規のフッ素化化合物を提供することを目的とする。
式(1a):
式(1b):
式(3):
式(3a):
式(3b):
また、本開示によれば、上記のフッ素化アミド化合物、または、上記のフッ素化含窒素複素環含有化合物を含有するプリント基板が提供される。
また、本開示によれば、誘電率が低く、かつ、誘電損失が低いフッ素化含窒素複素環含有化合物を提供することができる。
また、本開示によれば、新規のフッ素化化合物を提供することができる。
本開示のフッ素化アミド化合物は、式(1)で示される繰り返し単位を有する。
対数粘度ηinh=ln(溶液粘度/溶媒粘度)/溶液濃度
本開示のフッ素化含窒素複素環含有化合物は、式(3)で示される繰り返し単位を有する。
式(3):
フッ素化含窒素複素環含有化合物の誘電率および誘電損失をより一層低くすることができることから、フッ素化含窒素複素環含有化合物としては、平均重合度が比較的大きなポリマーであってよく、たとえば、平均重合度が100超のポリマーであってもよい。
対数粘度ηinh=ln(溶液粘度/溶媒粘度)/溶液濃度
本開示のフッ素化アミド化合物は、式(4)で示されるフッ素化化合物(4)を、後述する製造方法により製造した後、得られたフッ素化化合物(4)と式(5)で示される化合物(5)とを重合させることにより、好適に製造することができる。
式(6a):
式(4B):
シクロプロパン環、シクロブタン環、シクロペンタン環、シクロヘキサン環、シクロヘプタン環、シクロオクタン環、シクロノナン環、シクロデカン環、シクロウンデカン環、シクロドデカン環などの単環の飽和炭化水素環;
シクロプロペン環、シクロブテン環、シクロプロペン環、シクロヘキセン環、シクロヘプテン環、シクロオクテン環などの単環の非芳香族不飽和炭化水素環;
ノルボルネン環、ノルボルナジエン環、デカヒドロナフタレン環、ビシクロウンデカン環、スピロビシクロペンタン環などの多環の非芳香族炭化水素環;
ベンゼン環、ナフタレン環、フェナントレン環、アントラセン環、フルオレン環、テトラセン環、クリセン環、ピレン環、ペンタセン環、ベンゾピレン環、トリフェニレン環、ペリレン環、ビフェニル環、ターフェニル環、ジフェニルメタン環、ジフェニルエーテル環、ジフェニルスルホン環、ジフェニルケトン環などの芳香族炭化水素環;
などが挙げられる。
式(9):
R−OH
(式(9)中、Rは、置換基を有していてもよい直鎖状もしくは分岐鎖状のアルキル基または置換基を有していてもよい芳香族基である。)
本開示のフッ素化含窒素複素環含有化合物は、上記の製造方法によりフッ素化アミド化合物を得た後、フッ素化アミド化合物を脱水環化させることにより、好適に製造することができる。また、フッ素化アミド化合物を製造する際に、フッ素化化合物(4)と化合物(5)との重合を加温状態で行った場合には、化合物の一部または全部が脱水環化して、式(3)で示される繰り返し単位を有する化合物が形成され、結果として、生成物の一部または全部として、本開示のフッ素化含窒素複素環含有化合物が得られることがある。すなわち、本開示には、フッ素化アミド化合物およびフッ素化含窒素複素環含有化合物の混合物も含まれる。
(2)赤外スペクトル(FT−IR):日本分光(株)製FT/IR−4200
(3)核磁気共鳴スペクトル(NMR):BRUKER製AC400P
(4)熱重量測定(TGA):(株)日立ハイテクサイエンス製TG/DTA7300、昇温速度10℃/min
(5)示差走査熱量測定(DSC):(株)日立ハイテクサイエンス製DSC7000、昇温速度10℃/min
(6)熱機械分析(TMA):(株)日立ハイテクサイエンス製TMA7000、昇温速度10℃/min
(7)動的粘弾性測定(DMA):(株)日立ハイテクサイエンス製DMA7100、昇温速度2℃/min
(8)引張試験:(株)島津製作所製オートグラフAGS−D型、引張速度10mm/min
(9)紫外可視分光光度計:(株)島津製作所UV−1800
(10)屈折率測定:Metricon Model 2010/M PRISM COUPLER
(11)誘電率測定:AET製誘電率・誘電正接測定装置(空洞共振器タイプ、10GHz)
1,6−ビス(4−アミノフェニル)ドデカフルオロヘキサン(APDF6)
FT−IR(KBr、cm−1):3444(N−H)、3057(C−H)、1609(C=C)、1185(C−F)
1H−NMR(DMSO−d6、ppm):5.82(s,4H,NH2)、6.62(d,4H,Ar−H)、7.20(d,4H,Ar−H)
13C−NMR(DMSO−d6、ppm):113.0、127.6、152.4
19F−NMR(DMSO−d6、ppm):−122.2、−121.5、−108.0
融点:79.4℃(DSC)
元素分析:計算値 C,44.64%;H,2.50%;N,5.78%
実測値 C,44.66%;H,2.72%;N,5.49%
1,8−ビス(4−アミノフェニル)ヘキサデカフルオロオクタン(APHF8)
FT−IR(KBr、cm−1):3489〜3392(N−H)、3050 (C−H)、1581(C=C)、1259〜1145(C−F)
1H−NMR(DMSO−d6、ppm):5.86(s,4H,NH2)、6.66(d,4H,Ar−H)、7.22(d,4H,Ar−H)
13C−NMR(DMSO−d6、ppm):113.0、127.8、152.4
19F−NMR(DMSO−d6、ppm):−121.7、−121.1、−107.5
融点:85.8℃(DSC)
元素分析:計算値 C,41.16%;H,2.08%;N,4.80%
実測値 C,41.23%;H,2.28%;N,4.85%
1,6−ビス(p−トリル)ドデカフルオロヘキサン(TDF6)
1H−NMR(CDCl3、ppm):2.34(s、6H、CH3)、7.41(d、4H、Ar−H)、7.51(d、4H、Ar−H)
13C−NMR(CDCl3、ppm):20.86、126.46、129.67,136.58,136.67,138.60,138.71,142.90
19F−NMR(CDCl3、ppm):−109.72、−121.57、−122.13
1,6−ビス(4−カルボキシフェニル)ドデカフルオロヘキサン(CPDF6)
1H−NMR(DMSO−d6、ppm):7.80(d、4H、Ar−H)、8.13(d、4H、Ar−H)、13.50(s、1H、COOH)
13C−NMR(DMSO−d6、ppm):127.15,129.93,131.19,134.74,136.57,136.66,138.70,166.23
19F−NMR(DMSO−d6、ppm):−110.41、−121.57、−122.04
ビス(4,6−ジメトキシ−1,3,5−トリアジン−2−イル)−p−ドデカフルオロヘキシレンジベンゾエート(p−DFBBT)
1H−NMR(CDCl3、ppm):4.09(s、12H、CH3)、7.76(d、4H、Ar−H)、8.30(s、4H、Ar−H)
13C−NMR(CDCl3、ppm):56.20、127.64,130.90,131.61,137.01,137.10,139.19,161.54,170.70,171.13,174.39
19F−NMR(CDCl3、ppm):−112.65、−122.53、−123.10
フッ素化アミド化合物およびフッ素化含窒素複素環含有化合物(イミド化合物:APDF6−BPDA)
FT−IR(KBr、cm−1):1778(C=O)、1734(C=O)、1389(C−N)、1185(C−F)、740(イミド環)
溶解性:有機溶媒に不溶
5%重量減少温度:520℃(空気中)、555℃(窒素中)(TGA)
10%重量減少温度:550℃(空気中)、576℃(窒素中)(TGA)
炭化収率:53%(窒素中、800℃)(TGA)
ガラス転移温度:210℃(DMA)
熱膨張係数:43ppm/℃
カットオフ波長:389nm
500nmでの透過率:28%
平均屈折率(nave):1.579(d線)
屈折率から求められる誘電率(ε):2.72(ε=1.10×nave 2)
フッ素化アミド化合物およびフッ素化含窒素複素環含有化合物(イミド化合物:APDF6−6FDA)
FT−IR(KBr、cm−1):1789(C=O)、1725(C=O)、1376(C−N)、1199(C−F)、745(イミド環)
1H−NMR(CDCl3、ppm):7.65(d,4H,Ar−H)、7.76(d,4H,Ar−H)、7.91(d,2H,Ar−H)、7.96(s,2H,Ar−H)、8.08(d,2H,Ar−H)
19F−NMR(CDCl3、ppm):−126.8、−126.4、−115.9、−68.4
対数粘度(ηinh):0.52dL/g(0.5 g/dL濃度のNMP溶液、30℃測定)
GPC:数平均分子量(Mn)47000、分子量分布(Mw/Mn)2.5
溶解性:NMP、DMAc、DMF、DMI、THF、クロロホルム、アセトン、メタノール、酢酸エチル、THF、シクロヘキサンに室温で溶解
5%重量減少温度:509℃(空気中)、524℃(窒素中)(TGA)
10%重量減少温度:527℃(空気中)、544℃(窒素中)(TGA)
炭化収率:52%(窒素中、800℃)(TGA)
ガラス転移温度:221℃(DSC)、215℃(DMA)、213℃(TMA)
熱膨張係数(CTE):92ppm/℃
引張破断強度:58MPa
破断伸び:9.3%
引張弾性率:1.6GPa
カットオフ波長:337nm
500nmでの透過率:80%
平均屈折率(nave):1.526(d線)
屈折率から求められる誘電率(ε):2.55(ε=1.10×nave 2)
10GHzにおける誘電率(Dk):2.54
10GHzにおける誘電正接(Df):0.0022
フッ素化アミド化合物およびフッ素化含窒素複素環含有化合物(イミド化合物:APDF6−BPDA/6FDA(50/50))
FT−IR(KBr、cm−1):1792(C=O)、1741(C=O)、1380(C−N)、1179(C−F)、721(イミド環)
対数粘度(ηinh):0.43dL/g(0.5 g/dL濃度のNMP溶液、30℃測定)
溶解性:NMP、DMAc、DMFに室温で溶解
5%重量減少温度:503℃(空気中)、526℃(窒素中)(TGA)
10%重量減少温度:526℃(空気中)、550℃(窒素中)(TGA)
炭化収率:49%(窒素中、800℃)(TGA)
ガラス転移温度:205℃(DSC)、208℃(DMA)、210℃(TMA)
熱膨張係数(CTE):73(ppm/℃)
カットオフ波長:365nm
500nmでの透過率:73%
平均屈折率(nave):1.562(d線)
屈折率から求められる誘電率(ε):2.68(ε=1.10×nave 2)
10GHzにおける誘電率(Dk):2.58
10GHzにおける誘電正接(Df):0.0025
フッ素化アミド化合物およびフッ素化含窒素複素環含有化合物(イミド化合物:APHF8−BPDA)
FT−IR(KBr、cm−1):1782(C=O)、1725(C=O)、1375(C−N)、1205(C−F)、739(イミド環)
溶解性:有機溶媒に不溶
5%重量減少温度:521℃(空気中)、545℃(窒素中)(TGA)
10%重量減少温度:547℃(空気中)、564℃(窒素中)(TGA)
炭化収率:48%(窒素中、800℃)(TGA)
ガラス転移温度:190℃(DMA)
平均屈折率(nave):1.551(d線)
屈折率から求められる誘電率(ε):2.65(ε=1.10×nave 2)
10GHzにおける誘電率(Dk):2.72
10GHzにおける誘電正接(Df):0.0014
フッ素化アミド化合物およびフッ素化含窒素複素環含有化合物(イミド化合物:APHF8−6FDA)
FT−IR(KBr、cm−1):1793(C=O)、1742(C=O)、1381(C−N)、1180(C−F)、720(イミド環)
対数粘度(ηinh):0.51dL/g(0.5g/dL濃度のNMP溶液、30℃測定)
GPC:数平均分子量(Mn)27000、分子量分布(Mw/Mn)1.6
溶解性:NMP、DMAc、DMF、DMI、THF、クロロホルムに室温で溶解
5%重量減少温度:497℃(空気中)、524℃(窒素中)(TGA)
10%重量減少温度:516℃(空気中)、544℃(窒素中)(TGA)
炭化収率:49%(窒素中、800℃)(TGA)
ガラス転移温度:194℃(DSC)、190℃(DMA)、188℃(TMA)
熱膨張係数(CTE):85(ppm/℃)
引張破断強度:59MPa
破断伸び:4.8%
引張弾性率:1.7GPa
カットオフ波長:330nm
500nmでの透過率:83%
平均屈折率(nave):1.511(d線)
屈折率から求められる誘電率(ε):2.51(ε=1.10×nave 2)
10GHzにおける誘電率(Dk):2.39
10GHzにおける誘電正接(Df):0.0016
フッ素化アミド化合物(6FTA−p−DFBBT)
FT−IR(KBr、cm−1):3366(N−H)、1664(C=O)、1519(C=C)
1H−NMR(DMSO−d6、ppm):5.38(s、4H、NH2)、6.79(d、2H、Ar−H)、6.93(d、2H、Ar−H)、7.26(s、2H、Ar−H)、7.83(d、4H、Ar−H)、8.17(d、4H、Ar−H)、9.94(s、2H、NHCO)
対数粘度(ηinh):0.34dL/g(0.5g/dL濃度のNMP溶液、30℃測定)
GPC:数平均分子量(Mn)25000、分子量分布(Mw/Mn)2.0
溶解性:NMP、DMAc、DMF、DMSO、THF、アセトン、メタノールに室温で溶解
フッ素化アミド化合物(6FTAPh−p−DFBBT)
FT−IR(KBr、cm−1):3341(NHCO)、1672(C=O)、1598(C=C)、1532(C=C)
1H−NMR(CDCl3、ppm):6.36(s、2H、Ar−NH−Ar)、6.93(m、10H、Ar−H)、7.22(s、2H、Ar−H)、7.63(t、4H、Ar−H)、7.83−7.90(m、8H、Ar−H)、8.80(s、2H、NHCO)
対数粘度(ηinh):0.37dL/g(0.5g/dL濃度のNMP溶液、30℃測定)
GPC:数平均分子量(Mn)59000、分子量分布(Mw/Mn)1.3
溶解性:NMP,DMAc,DMF,DMSO,THF,クロロホルム,アセトンに室温で溶解
フッ素化含窒素複素環含有化合物(イミダゾール化合物:6FTA−p−DFBBT)
FT−IR(KBr、cm−1):1551(C=C)、1451(C=N)、723(C−F)
元素分析:測定値 C,49.72%;H,2.33%;N,6.60%
計算値 C,50.37%;H,1.93%;N,6.71%
溶解性:NMPに溶解
ガラス転移温度:240℃(DSC測定)
5%重量減少温度:429℃(空気中)、442℃(窒素中)(TGA)
10%重量減少温度:478℃(空気中)、497℃(窒素中)(TGA)
炭化収率:57%(窒素中、800℃)(TGA)
カットオフ波長:342nm
500nmにおける光透過率:86%
平均屈折率(nave):1.565(d線)
屈折率から求められる誘電率(ε):2.69(ε=1.10×nave 2)
フッ素化含窒素複素環含有化合物(イミダゾール化合物:6FTAPh−p−DFBBT)
FT−IR(KBr、cm−1):1596(C=C)、1503(C=C)、1455(C=N)
溶解性:NMP、DMAc、DMF,THFに室温で溶解
ガラス転移温度:211℃(DSC)
5%重量減少温度:503℃(空気中)、519℃(窒素中)(TGA)
10%重量減少温度:532℃(空気中)、542℃(窒素中)(TGA)
炭化収率:61%(窒素中、800℃)(TGA)
カットオフ波長:340nm
500nmにおける光透過率:77%
平均屈折率(nave):1.545(d線)
屈折率から求められる誘電率(ε):2.63(ε=1.10×nave 2)
1,6−ビス(3−アミノフェニル)ドデカフルオロヘキサン(mAPDF6)
1H−NMR(CDCl3、ppm):3.81(s,4H,NH2)、6.83(d,2H,Ar−H)、6.85(s,2H,Ar−H)、6.95(d,2H,Ar−H)、7.24(t,2H,Ar−H)
13C−NMR(CDCl3、ppm):113.1、116.9、118.2、129.6,130.3,146.7
19F−NMR(CDCl3、ppm):−121.9、−121.3、−110.7
融点:79.4℃(DSC)
元素分析:計算値 C,44.64%;H,2.50%;N,5.78%
実測値 C,44.75%;H,2.80%;N,5.52%
1,6−ビス(4−クロロカルボニルフェニル)ドデカフルオロヘキサン(CCPDF6)
FT−IR、1H−NMR、13C−NMR、19F−NMRおよび元素分析によって構造を確認した。
FT−IR(KBr、cm−1):3063(Ar−H)、1746(C=O)、1142(C−F)
1H−NMR(CDCl3、ppm):8.24(d,4H,Ar−H)、7.75(d,4H,Ar−H)
13C−NMR(CDCl3、ppm):127.78、131.40、135.49,136.44、167.76、
19F−NMR(CDCl3、ppm):−111.33、−121.10、−121.60
融点:129〜130℃
元素分析:計算値 C,41.48%;H,1.39%
実測値 C,41.43%;H,1.48%
フッ素化アミド化合物およびフッ素化含窒素複素環含有化合物(イミド化合物:APDF6/BisAAF(50/50)−6FDA)
数平均分子量(Mn):31000、分子量分布(Mw/Mn):2.5(GPC)
溶解性:NMP、DMAc、シクロヘキサノン、THF、クロロホルム、酢酸エチル、アセトンに室温で溶解
5%重量減少温度:502℃(空気中)、524℃(窒素中)(TGA)
10%重量減少温度:522℃(空気中)、542℃(窒素中)(TGA)
炭化収率:52%(窒素中、800℃)(TGA)
ガラス転移温度:265℃(DSC)、258℃(DMA)、267℃(TMA)
熱膨張係数(CTE):62(ppm/℃)
カットオフ波長:354nm
500nmでの透過率:84%
平均屈折率(nave):1.537(d線)
屈折率から求められる誘電率(ε):2.60(ε=1.10×nave 2)
10GHzにおける誘電率(Dk):2.49
10GHzにおける誘電正接(Df):0.0043
フッ素化アミド化合物およびフッ素化含窒素複素環含有化合物(イミド化合物:APDF6/TFMB(50/50)−6FDA)
数平均分子量(Mn):50000、分子量分布(Mw/Mn):1.8(GPC)
溶解性:NMP、DMAc、シクロヘキサノン、THF、クロロホルム、酢酸エチル、アセトンに室温で溶解
5%重量減少温度:505℃(空気中)、538℃(窒素中)(TGA)
10%重量減少温度:525℃(空気中)、560℃(窒素中)(TGA)
炭化収率:52%(窒素中、800℃)(TGA)
ガラス転移温度:268℃(DSC)、257℃(DMA)、261℃(TMA)
熱膨張係数(CTE):43(ppm/℃)
カットオフ波長:355nm
500nmでの透過率:83%
平均屈折率(nave):1.538(d線)
屈折率から求められる誘電率(ε):2.60(ε=1.10×nave 2)
10GHzにおける誘電率(Dk):2.52
10GHzにおける誘電正接(Df):0.0039
フッ素化アミド化合物およびフッ素化含窒素複素環含有化合物(イミド化合物:APHF8/BisAAF(50/50)−6FDA)
数平均分子量(Mn):30000、分子量分布(Mw/Mn):2.4(GPC)
溶解性:NMP、DMAc、THF、クロロホルム、酢酸エチル、アセトンに室温で溶解
5%重量減少温度:509℃(空気中)、520℃(窒素中)(TGA)
10%重量減少温度:529℃(空気中)、539℃(窒素中)(TGA)
炭化収率:51%(窒素中、800℃)(TGA)
ガラス転移温度:252℃(DSC)、247℃(DMA)、246℃(TMA)
熱膨張係数(CTE):75(ppm/℃)
カットオフ波長:352nm
500nmでの透過率:73%
平均屈折率(nave):1.528(d線)
屈折率から求められる誘電率(ε):2.57(ε=1.10×nave 2)
10GHzにおける誘電率(Dk):2.49
10GHzにおける誘電正接(Df):0.0023
フッ素化アミド化合物およびフッ素化含窒素複素環含有化合物(イミド化合物:APHF8/TFMB(50/50)−6FDA)
数平均分子量(Mn):55000、分子量分布(Mw/Mn):2.4(GPC)
溶解性:NMP、DMAc、シクロヘキサノン、THF、クロロホルム、酢酸エチル、アセトンに室温で溶解
5%重量減少温度:525℃(空気中)、529℃(窒素中)(TGA)
10%重量減少温度:545℃(空気中)、550℃(窒素中)(TGA)
炭化収率:51%(窒素中、800℃)(TGA)
ガラス転移温度:255℃(DSC)、241℃(DMA)、239℃(TMA)
熱膨張係数(CTE):55(ppm/℃)
カットオフ波長:350nm
500nmでの透過率:80%
平均屈折率(nave):1.528(d線)
屈折率から求められる誘電率(ε):2.57(ε=1.10×nave 2)
10GHzにおける誘電率(Dk):2.57
10GHzにおける誘電正接(Df):0.0031
フッ素化アミド化合物およびフッ素化含窒素複素環含有化合物(イミド化合物:BisAAF−6FDA)
数平均分子量(Mn)26000、分子量分布(Mw/Mn)2.3(GPC)
溶解性:DMF、DMAc、THF、クロロホルム、酢酸エチル、アセトンに室温で溶解
5%重量減少温度:508℃(空気中)、524℃(窒素中)(TGA)
10%重量減少温度:525℃(空気中)、539℃(窒素中)(TGA)
炭化収率:54%(窒素中、800℃)(TGA)
ガラス転移温度:311℃(DSC)、313℃(DMA)、310℃(TMA)
熱膨張係数(CTE):69ppm/℃
カットオフ波長:354nm
500nmでの透過率:88%
平均屈折率(nave):1.550(d線)
屈折率から求められる誘電率(ε):2.64(ε=1.10×nave 2)
10GHzにおける誘電率(Dk):2.65
10GHzにおける誘電正接(Df):0.0070
フッ素化アミド化合物およびフッ素化含窒素複素環含有化合物(イミド化合物:TFMB−6FDA)
数平均分子量(Mn)21000、分子量分布(Mw/Mn)1.9(GPC)
溶解性:DMF、DMAc、シクロヘキサノン、THF、酢酸エチル、アセトンに室温で溶解
5%重量減少温度:527℃(空気中)、530℃(窒素中)(TGA)
10%重量減少温度:543℃(空気中)、552℃(窒素中)(TGA)
炭化収率:52%(窒素中、800℃)(TGA)
ガラス転移温度:332℃(DSC)、331℃(DMA)、323℃(TMA)
熱膨張係数(CTE):68ppm/℃
カットオフ波長:351nm
500nmでの透過率:84%
平均屈折率(nave):1.554(d線)
屈折率から求められる誘電率(ε):2.66(ε=1.10×nave 2)
10GHzにおける誘電率(Dk):2.74
10GHzにおける誘電正接(Df):0.0066
Claims (12)
- 式(1)で示される繰り返し単位の平均重合度が2〜100である請求項1に記載のフッ素化アミド化合物。
- 式(3)で示される繰り返し単位の平均重合度が2〜100である請求項5に記載のフッ素化含窒素複素環含有化合物。
- 請求項1〜4のいずれかに記載のフッ素化アミド化合物、または、請求項5〜8のいずれかに記載のフッ素化含窒素複素環含有化合物を含有する低誘電体。
- 請求項1〜4のいずれかに記載のフッ素化アミド化合物、または、請求項5〜8のいずれかに記載のフッ素化含窒素複素環含有化合物を含有するプリント基板。
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