JP6873874B2 - ジアミン、ポリアミド酸、ポリイミド及びポリイミド溶液 - Google Patents
ジアミン、ポリアミド酸、ポリイミド及びポリイミド溶液 Download PDFInfo
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- JP6873874B2 JP6873874B2 JP2017175295A JP2017175295A JP6873874B2 JP 6873874 B2 JP6873874 B2 JP 6873874B2 JP 2017175295 A JP2017175295 A JP 2017175295A JP 2017175295 A JP2017175295 A JP 2017175295A JP 6873874 B2 JP6873874 B2 JP 6873874B2
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- Prior art keywords
- polyimide
- solvent
- reaction
- solution
- diamine
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- 229920001721 polyimide Polymers 0.000 title claims description 125
- 239000004642 Polyimide Substances 0.000 title claims description 104
- 150000004985 diamines Chemical class 0.000 title claims description 53
- 229920005575 poly(amic acid) Polymers 0.000 title claims description 37
- 125000003118 aryl group Chemical group 0.000 claims description 12
- 125000004185 ester group Chemical group 0.000 claims description 11
- 125000001033 ether group Chemical group 0.000 claims description 9
- 230000009477 glass transition Effects 0.000 claims description 9
- 239000007787 solid Substances 0.000 claims description 9
- 125000001931 aliphatic group Chemical group 0.000 claims description 7
- 239000002904 solvent Substances 0.000 description 97
- 238000006243 chemical reaction Methods 0.000 description 78
- 239000000243 solution Substances 0.000 description 68
- 238000000034 method Methods 0.000 description 62
- -1 tetracarboxylic acid dianhydride Chemical class 0.000 description 40
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 38
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 27
- 229930185605 Bisphenol Natural products 0.000 description 25
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 25
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 24
- 238000004519 manufacturing process Methods 0.000 description 23
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 22
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 21
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 20
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 19
- 239000000843 powder Substances 0.000 description 19
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 18
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 18
- 239000000126 substance Substances 0.000 description 17
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 17
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 16
- 239000002253 acid Substances 0.000 description 16
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- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 12
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- 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 12
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 description 11
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- YLQWCDOCJODRMT-UHFFFAOYSA-N fluoren-9-one Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3C2=C1 YLQWCDOCJODRMT-UHFFFAOYSA-N 0.000 description 11
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 10
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- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 9
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 9
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 9
- 150000001408 amides Chemical class 0.000 description 9
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 9
- 239000002585 base Substances 0.000 description 9
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 9
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- 238000006722 reduction reaction Methods 0.000 description 9
- 239000008096 xylene Substances 0.000 description 9
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 8
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 8
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 8
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 8
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- 239000000758 substrate Substances 0.000 description 8
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 8
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 7
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 7
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 7
- 238000000862 absorption spectrum Methods 0.000 description 7
- 238000006266 etherification reaction Methods 0.000 description 7
- 239000011521 glass Substances 0.000 description 7
- 150000007524 organic acids Chemical class 0.000 description 7
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 7
- 239000002994 raw material Substances 0.000 description 7
- 229910052717 sulfur Inorganic materials 0.000 description 7
- 239000011593 sulfur Substances 0.000 description 7
- 125000001834 xanthenyl group Chemical group C1=CC=CC=2OC3=CC=CC=C3C(C12)* 0.000 description 7
- URLKBWYHVLBVBO-UHFFFAOYSA-N Para-Xylene Chemical group CC1=CC=C(C)C=C1 URLKBWYHVLBVBO-UHFFFAOYSA-N 0.000 description 6
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 230000015572 biosynthetic process Effects 0.000 description 6
- 150000001875 compounds Chemical class 0.000 description 6
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 6
- BGTOWKSIORTVQH-UHFFFAOYSA-N cyclopentanone Chemical compound O=C1CCCC1 BGTOWKSIORTVQH-UHFFFAOYSA-N 0.000 description 6
- 238000001914 filtration Methods 0.000 description 6
- 239000012535 impurity Substances 0.000 description 6
- 239000005453 ketone based solvent Substances 0.000 description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 6
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 6
- 229960001755 resorcinol Drugs 0.000 description 6
- 125000006158 tetracarboxylic acid group Chemical group 0.000 description 6
- 239000002966 varnish Substances 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 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 5
- 238000004458 analytical method Methods 0.000 description 5
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 5
- 239000003153 chemical reaction reagent Substances 0.000 description 5
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 5
- 230000018044 dehydration Effects 0.000 description 5
- 238000006297 dehydration reaction Methods 0.000 description 5
- 238000010438 heat treatment Methods 0.000 description 5
- 229910052739 hydrogen Inorganic materials 0.000 description 5
- 239000001257 hydrogen Substances 0.000 description 5
- 239000000178 monomer Substances 0.000 description 5
- 238000012360 testing method Methods 0.000 description 5
- 238000005406 washing Methods 0.000 description 5
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 4
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 4
- 238000005160 1H NMR spectroscopy Methods 0.000 description 4
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 4
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 4
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 4
- JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 4
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- 150000004820 halides Chemical class 0.000 description 4
- FUZZWVXGSFPDMH-UHFFFAOYSA-M hexanoate Chemical compound CCCCCC([O-])=O FUZZWVXGSFPDMH-UHFFFAOYSA-M 0.000 description 4
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- CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 4
- BSKHPKMHTQYZBB-UHFFFAOYSA-N 2-methylpyridine Chemical compound CC1=CC=CC=N1 BSKHPKMHTQYZBB-UHFFFAOYSA-N 0.000 description 3
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- GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 2
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- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical class OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- HDFRDWFLWVCOGP-UHFFFAOYSA-N carbonothioic O,S-acid Chemical class OC(S)=O HDFRDWFLWVCOGP-UHFFFAOYSA-N 0.000 description 1
- 238000010531 catalytic reduction reaction Methods 0.000 description 1
- 239000002734 clay mineral Substances 0.000 description 1
- 239000011362 coarse particle Substances 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000011889 copper foil Substances 0.000 description 1
- 229930003836 cresol Natural products 0.000 description 1
- 239000003431 cross linking reagent Substances 0.000 description 1
- 150000004292 cyclic ethers Chemical class 0.000 description 1
- CURBACXRQKTCKZ-UHFFFAOYSA-N cyclobutane-1,2,3,4-tetracarboxylic acid Chemical compound OC(=O)C1C(C(O)=O)C(C(O)=O)C1C(O)=O CURBACXRQKTCKZ-UHFFFAOYSA-N 0.000 description 1
- 238000006356 dehydrogenation reaction Methods 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 125000006159 dianhydride group Chemical group 0.000 description 1
- 229940028356 diethylene glycol monobutyl ether Drugs 0.000 description 1
- XXJWXESWEXIICW-UHFFFAOYSA-N diethylene glycol monoethyl ether Chemical compound CCOCCOCCO XXJWXESWEXIICW-UHFFFAOYSA-N 0.000 description 1
- 229940075557 diethylene glycol monoethyl ether Drugs 0.000 description 1
- 238000000113 differential scanning calorimetry Methods 0.000 description 1
- HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- JBTWLSYIZRCDFO-UHFFFAOYSA-N ethyl methyl carbonate Chemical compound CCOC(=O)OC JBTWLSYIZRCDFO-UHFFFAOYSA-N 0.000 description 1
- 229940093476 ethylene glycol Drugs 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000003063 flame retardant Substances 0.000 description 1
- GAEKPEKOJKCEMS-UHFFFAOYSA-N gamma-valerolactone Chemical compound CC1CCC(=O)O1 GAEKPEKOJKCEMS-UHFFFAOYSA-N 0.000 description 1
- 238000001879 gelation Methods 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 239000011964 heteropoly acid Substances 0.000 description 1
- 238000007602 hot air drying Methods 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- 150000004679 hydroxides Chemical class 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- YAMHXTCMCPHKLN-UHFFFAOYSA-N imidazolidin-2-one Chemical compound O=C1NCCN1 YAMHXTCMCPHKLN-UHFFFAOYSA-N 0.000 description 1
- 150000003949 imides Chemical class 0.000 description 1
- 239000011256 inorganic filler Substances 0.000 description 1
- 229910003475 inorganic filler Inorganic materials 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 229910017053 inorganic salt Inorganic materials 0.000 description 1
- 239000011810 insulating material Substances 0.000 description 1
- 239000003456 ion exchange resin Substances 0.000 description 1
- 229920003303 ion-exchange polymer Polymers 0.000 description 1
- 238000000752 ionisation method Methods 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- GJRQTCIYDGXPES-UHFFFAOYSA-N iso-butyl acetate Natural products CC(C)COC(C)=O GJRQTCIYDGXPES-UHFFFAOYSA-N 0.000 description 1
- FGKJLKRYENPLQH-UHFFFAOYSA-M isocaproate Chemical compound CC(C)CCC([O-])=O FGKJLKRYENPLQH-UHFFFAOYSA-M 0.000 description 1
- JMMWKPVZQRWMSS-UHFFFAOYSA-N isopropanol acetate Natural products CC(C)OC(C)=O JMMWKPVZQRWMSS-UHFFFAOYSA-N 0.000 description 1
- 229940011051 isopropyl acetate Drugs 0.000 description 1
- GWYFCOCPABKNJV-UHFFFAOYSA-M isovalerate Chemical compound CC(C)CC([O-])=O GWYFCOCPABKNJV-UHFFFAOYSA-M 0.000 description 1
- OQAGVSWESNCJJT-UHFFFAOYSA-N isovaleric acid methyl ester Natural products COC(=O)CC(C)C OQAGVSWESNCJJT-UHFFFAOYSA-N 0.000 description 1
- 150000002596 lactones Chemical class 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 229940018564 m-phenylenediamine Drugs 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- GBMDVOWEEQVZKZ-UHFFFAOYSA-N methanol;hydrate Chemical compound O.OC GBMDVOWEEQVZKZ-UHFFFAOYSA-N 0.000 description 1
- SKTCDJAMAYNROS-UHFFFAOYSA-N methoxycyclopentane Chemical compound COC1CCCC1 SKTCDJAMAYNROS-UHFFFAOYSA-N 0.000 description 1
- CZRKJHRIILZWRC-UHFFFAOYSA-N methyl acetate;propane-1,2-diol Chemical compound COC(C)=O.CC(O)CO CZRKJHRIILZWRC-UHFFFAOYSA-N 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 239000002808 molecular sieve Substances 0.000 description 1
- YKYONYBAUNKHLG-UHFFFAOYSA-N n-Propyl acetate Natural products CCCOC(C)=O YKYONYBAUNKHLG-UHFFFAOYSA-N 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
- 230000008520 organization Effects 0.000 description 1
- JCGNDDUYTRNOFT-UHFFFAOYSA-N oxolane-2,4-dione Chemical compound O=C1COC(=O)C1 JCGNDDUYTRNOFT-UHFFFAOYSA-N 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 239000003504 photosensitizing agent Substances 0.000 description 1
- 239000003505 polymerization initiator Substances 0.000 description 1
- 230000000379 polymerizing effect Effects 0.000 description 1
- 229910000028 potassium bicarbonate Inorganic materials 0.000 description 1
- 235000015497 potassium bicarbonate Nutrition 0.000 description 1
- 239000011736 potassium bicarbonate Substances 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 235000011181 potassium carbonates Nutrition 0.000 description 1
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
- 229940086066 potassium hydrogencarbonate Drugs 0.000 description 1
- BDAWXSQJJCIFIK-UHFFFAOYSA-N potassium methoxide Chemical compound [K+].[O-]C BDAWXSQJJCIFIK-UHFFFAOYSA-N 0.000 description 1
- WYVAMUWZEOHJOQ-UHFFFAOYSA-N propionic anhydride Chemical compound CCC(=O)OC(=O)CC WYVAMUWZEOHJOQ-UHFFFAOYSA-N 0.000 description 1
- 229940090181 propyl acetate Drugs 0.000 description 1
- RUOJZAUFBMNUDX-UHFFFAOYSA-N propylene carbonate Chemical compound CC1COC(=O)O1 RUOJZAUFBMNUDX-UHFFFAOYSA-N 0.000 description 1
- KOUKXHPPRFNWPP-UHFFFAOYSA-N pyrazine-2,5-dicarboxylic acid;hydrate Chemical compound O.OC(=O)C1=CN=C(C(O)=O)C=N1 KOUKXHPPRFNWPP-UHFFFAOYSA-N 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000013557 residual solvent Substances 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 238000005070 sampling Methods 0.000 description 1
- 239000004065 semiconductor Substances 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 235000017550 sodium carbonate Nutrition 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- 230000003595 spectral effect Effects 0.000 description 1
- MDSIYHVHIUDLDT-UHFFFAOYSA-N spiro[fluorene-9,9'-xanthene]-2,2'-diol Chemical compound C1=CC=CC=2OC3=CC=C(C=C3C3(C12)C1=CC=CC=C1C=1C=CC(=CC13)O)O MDSIYHVHIUDLDT-UHFFFAOYSA-N 0.000 description 1
- 230000003068 static effect Effects 0.000 description 1
- 230000001629 suppression Effects 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- YJBKVPRVZAQTPY-UHFFFAOYSA-J tetrachlorostannane;dihydrate Chemical compound O.O.Cl[Sn](Cl)(Cl)Cl YJBKVPRVZAQTPY-UHFFFAOYSA-J 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- NJRXVEJTAYWCQJ-UHFFFAOYSA-N thiomalic acid Chemical compound OC(=O)CC(S)C(O)=O NJRXVEJTAYWCQJ-UHFFFAOYSA-N 0.000 description 1
- NBOMNTLFRHMDEZ-UHFFFAOYSA-N thiosalicylic acid Chemical compound OC(=O)C1=CC=CC=C1S NBOMNTLFRHMDEZ-UHFFFAOYSA-N 0.000 description 1
- 239000011135 tin Substances 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- 239000011573 trace mineral Substances 0.000 description 1
- 235000013619 trace mineral Nutrition 0.000 description 1
- 238000005809 transesterification reaction Methods 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- SRPWOOOHEPICQU-UHFFFAOYSA-N trimellitic anhydride Chemical compound OC(=O)C1=CC=C2C(=O)OC(=O)C2=C1 SRPWOOOHEPICQU-UHFFFAOYSA-N 0.000 description 1
- YFTHZRPMJXBUME-UHFFFAOYSA-N tripropylamine Chemical compound CCCN(CCC)CCC YFTHZRPMJXBUME-UHFFFAOYSA-N 0.000 description 1
- 239000000326 ultraviolet stabilizing agent Substances 0.000 description 1
- 238000001291 vacuum drying Methods 0.000 description 1
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 1
- 239000010887 waste solvent Substances 0.000 description 1
- 239000003643 water by type Substances 0.000 description 1
- 230000002087 whitening effect Effects 0.000 description 1
- 239000010457 zeolite Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- PAPBSGBWRJIAAV-UHFFFAOYSA-N ε-Caprolactone Chemical compound O=C1CCCCCO1 PAPBSGBWRJIAAV-UHFFFAOYSA-N 0.000 description 1
Images
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- Pyrane Compounds (AREA)
- Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
Description
本発明のポリイミドのモノマーである、本発明のジアミンは上記一般式(1)で表される。上記一般式(1)中、X1はエステル基またはエーテル基を表し、ジアミンの製造容易性の観点からエステル基が好ましい。
本発明のポリアミド酸は上記一般式(2)で表され、本発明のポリイミドは上記一般式(3)で表される。上記一般式(2)及び(3)中、X1はエステル基又はエーテル基を表し、上記一般式(1)で表されるジアミンの製造容易性の観点からエステル基が好ましい。
本発明のポリイミド溶液は、上述したポリイミドと有機溶媒とを含有する。ポリイミド溶液中のポリイミド濃度は、ポリイミドフィルムの製造容易性の観点から、固形分濃度で5重量%以上であることが好ましく、ポリイミド溶液を用いて塗工されたフィルムの平滑性を確保する観点から5〜40重量%、特に5〜20重量%であることが好ましい。
本発明のポリアミド酸を製造する方法は特に限定されず、公知の方法を適用することができる。より具体的には、上述した上記一般式(1)で表されるジアミン、及び必要に応じ併用する他のジアミンを後述する重合溶媒に溶解し、これに上述した本発明のポリアミド酸及びポリイミドを構成するテトラカルボン酸二無水物を徐々に添加し、0〜100℃、好ましくは20〜60℃で、0.5〜100時間、好ましくは1〜72時間攪拌する。
本発明のポリイミドは、上記の方法で得られたポリアミド酸を脱水閉環反応(イミド化反応)することで製造することができる。イミド化反応の方法としては、熱イミド化反応と化学イミド化反応が例示される。
・装置:(株)島津製作所製 LC−2010C
・カラム:一般財団法人 化学物質評価研究機構製 L−column ODS(5μm、4.6mmφ×250mm)
・移動相:A液=50%メタノール水、B液=メタノール。なお、B液濃度に付、下記の通り濃度を変化させ分析を行った。
・B液濃度:0%(0分)→100%(30分)→100%(40分)。
・流量:1.0ml/分
・カラム温度:40℃
・検出波長:UV 254nm
なお、以下実施例にて記載した各成分の含量及び純度は上記条件で測定したHPLCの面積百分率である。
1H−NMR及び13C−NMRは、内部標準としてテトラメチルシランを用い、溶媒としてDMSO−d6を用いて、JEOL−ESC400分光計によって記録した。
・装置:Waters社製 Xevo G2 Q−Tof
・カラム:化学物質評価研究機構製 L−Column2 ODS(2μm、2.1mmφ×100mm)
・カラム温度:40℃
・検出波長:UV 220−500nm
・移動相:A液=10mM酢酸アンモニウム水、B液=メタノール。なお、B液濃度に付、下記の通り濃度を変化させ分析を行った。
B液濃度:60%(0min)→65%(25min)→100%(35min)
・移動相流量:0.3ml/min
・検出法:Q−Tof
・イオン化法:ESI(+、−)法
・Ion Source:電圧(+)2.0kV、(−)1.5kV、温度120℃
・Sampling Cone :電圧 30V、ガスフロー50L/h
・Desolvation Gas:温度500℃、ガスフロー1000L/h
フーリエ変換赤外分光光度計(日本分光社製FT−IR4100)を用い、KBrプレート法にて本発明のジアミンの赤外線吸収スペクトルを測定した。
本発明のジアミンの1H−NMR及び13C−NMRは、内部標準としてテトラメチルシランを用い、溶媒としてDMSO−d6を用いて、JEOL−ECP400分光計によって記録した。
ネッチジャパン社製示差走査熱量分析装置(DSC3100)を用いて、窒素雰囲気中、昇温速度5℃/分で測定した。
本発明のジアミンが十分高い純度を有していることを確認するため、ジェイ・サイエンス・ラボ(株)社製 有機微量元素分析装置(JM10)を用いて、元素分析を行った。
フーリエ変換赤外分光光度計(日本分光社製FT−IR4100)を用い、透過法にて本発明のポリイミドの薄膜の赤外線吸収スペクトルを測定した。
ポリイミドの粉末をN,N−ジメチルアセトアミド(DMAc)に溶解し、またはポリアミド酸ワニスを希釈して0.5重量%のDMAc溶液とし、オストワルド粘度計を用いて30℃で還元粘度を測定した。この値は実質的に固有粘度と見なすことができ、この値が高い程分子量が高いことを表す。
ネッチジャパン(株)社製熱機械分析装置(TMA4000)を用い、試験片に一定の静荷重(膜厚20μmのフィルムに対して10g)をかけ、昇温速度5℃/分で昇温して、試験片の長さを計測し、TMA曲線を得た。
試験片が急激に伸びる温度の前後の曲線にそれぞれ接線を引き、2つの接線の交点より、ガラス転移温度(Tg)を求めた。Tgが高いほど、物理的耐熱性が高いことを表す。
ネッチジャパン社製熱機械分析装置(TMA4000)を用いて、熱機械分析により、荷重0.5g/膜厚1μm、昇温速度5℃/分における試験片の伸びより、100〜200℃の範囲での平均値としてポリイミドフィルム(膜厚約20μm)のCTEを求めた。この値が低い程、熱寸法安定性に優れていることを表す。
得られたポリイミド粉末10mgに対し、有機溶媒1mL(固形分濃度約1重量%)をサンプル管に入れ、試験管ミキサーを用いて5分間撹拌して溶解状態を目視で確認した。評価基準は以下の通り。
++:室温で溶解
+:加熱して溶解
―:不溶
ナス型フラスコに、製造例1に記載の方法と同様の製法により製造した、上記式(4)で表されるビスフェノール(3.658g、10.0mmol)を脱水テトラヒドロフラン(THF、64.2mL)に溶かし、更に脱酸剤としてピリジン(4.85mL、60.0mmol)を添加し、セプタムキャップで密栓してA液とした。
次に別の三口フラスコ中、4−ニトロ安息香酸クロリド(5.587g、30.1mmol)を脱水THF(9.4mL)に溶解し、セプタムキャップで密栓してB液とした。B液を氷浴で冷却し、マグネチックスターラーで攪拌しながら、B液にA液をシリンジでゆっくりと滴下した。
滴下終了後、冷却下で数時間攪拌し、更に室温で12時間撹拌した。反応終了後、析出物を濾別し、THFで洗浄したのち、塩化物イオンが検出されなくなるまで水で洗浄した。メタノールで溶媒置換してから120℃で12時間真空乾燥し、淡黄色の粗生成物4.6g(収率:70%)が得られた(融点301℃)。FT−IRおよび1H−NMRスペクトルを測定して分析したところ、目的とする高純度のジニトロ体であることを確認した。
前記反応終了後、水素バブリングを継続したまま室温まで冷却し、Pd/Cを濾過により除去した。得られた濾液をエバポレーターで濃縮し、水(200mL)を加えて白色の粗生成物を析出させた。得られた粗生成物を水およびメタノールで洗浄・濾過し、120℃で12時間真空乾燥して、白色の生成物3.3g(収率86%)を得た。この生成物の分析結果を以下に示す。
・FT−IRスペクトル(KBr、cm−1):3459/3363/3217(アミン、N−H伸縮振動)、3060(芳香族C−H伸縮振動)、1714(エステルC=O伸縮振動)、1631(NH2変角振動)、1516(1,4−フェニレン基)、1479(置換フェニル基)、1281(エステル+キサンテン基C−O−C伸縮振動)。
・1H−NMRスペクトル(400MHz,DMSO−d6,δ,ppm):1H−NMRスペクトル(400MHz,DMSO−d6,δ,ppm):8.00(d、2H、J=7.6Hz、フルオレン基4,8−プロトン)、7.78(d、2H、J=8.7Hz、アニリン3,5−プロトン)、7.62(d、2H、J=8.8Hz、アニリン3’,5’−プロトン)、7.45(td、2H、J=7.5、1.0Hz、フルオレン基3,7−プロトン)、7.39(d、1H、J=8.9Hz、キサンテン基8−プロトン)、7.30(td、2H、J=7.6、1.0Hz、フルオレン基2,6−プロトン)、7.22(sd、1H、J=2.4Hz、キサンテン基4−プロトン)、7.19(d、2H、J=7.6Hz、フルオレン基1,5−プロトン)、7.15(dd、1H、J=8.9、2.7Hz、キサンテン基7−プロトン)、6.73(dd、1H、J=8.6、2.4Hz、キサンテン基2−プロトン)、6.63(d、2H、J=8.8Hz、アニリン2,6−プロトン)、6.52(d、2H、J=8.8Hz、アニリン2’,6’−プロトン)、6.29(d、1H、J=8.5Hz、キサンテン基1−プロトン)、6.20(s、2H、アミン)、6.13(s、2H、アミン)、6.03(sd、1H、J=2.7Hz、キサンテン基5−プロトン)。
・元素分析(分子量602.65):推定値(%)C;77.73、H;4.35、N;4.65、分析値C;77.25、H;4.48、N;4.78。
よく乾燥した密閉反応容器に、2,2’−ビス(トリフルオロメチル)ベンジジン(以下、TFMBと称することもある)1mmol、および実施例1と同様の製法により製造した、上記式(5)で表されるジアミン(1mmol)を入れ、モレキュラーシーブス4Aで十分に脱水したジメチルアセトアミド(以下、DMAcと称することもある)を入れて溶解した。この溶液に1,2,3,4−シクロブタンテトラカルボン酸二無水物(CBDA)粉末(2mmol)を加え、初期の全溶質濃度30重量%より重合反応を開始した。反応開始後、室温で72時間攪拌することで均一で粘稠なポリアミド酸溶液が得られた。なお、反応中、溶液粘度が高くなりすぎたため、DMAcを適宜追加し、最終溶質濃度は21%であった。
・ガラス転移温度(Tg):352℃
・CTE:17.9ppm/K
実施例2において、本発明の式(5)で表されるジアミン使用しない代わりに、TFMBを2mmol使用する以外は実施例2に準じて重合を行った後、熱イミド化工程を経てポリイミドフィルムを作製し、膜物性評価を行った。得られたポリイミドは如何なる溶媒にも不溶であり、溶液加工性を有していなかった。
ジアミンとして以下式(10):
・ガラス転移温度(Tg):364℃
・CTE:26.0ppm/K
DMF:N,N−ジメチルホルムアミド
DMAc:N,N−ジメチルアセトアミド
NMP:N−メチルピロリドン
GBL:γ―ブチロラクトン
CPN:シクロペンタノン
Claims (6)
- 請求項3に記載のポリイミドを固形分濃度で5重量%以上含むポリイミド溶液。
- 請求項3に記載のポリイミドを含むポリイミドフィルム。
- ガラス転移温度が250℃以上である、請求項3に記載のポリイミド、又は請求項5に記載のポリイミドフィルム。
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