JP2010209335A - 金属含有ポリアミック酸の架橋体、金属含有ポリイミドの架橋体、その製造方法及びそれを利用したポリイミドフィルム - Google Patents
金属含有ポリアミック酸の架橋体、金属含有ポリイミドの架橋体、その製造方法及びそれを利用したポリイミドフィルム Download PDFInfo
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- JP2010209335A JP2010209335A JP2010053868A JP2010053868A JP2010209335A JP 2010209335 A JP2010209335 A JP 2010209335A JP 2010053868 A JP2010053868 A JP 2010053868A JP 2010053868 A JP2010053868 A JP 2010053868A JP 2010209335 A JP2010209335 A JP 2010209335A
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- Prior art keywords
- metal
- group
- polyamic acid
- product
- polyimide
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- 229910052751 metal Inorganic materials 0.000 title claims abstract description 138
- 239000002184 metal Substances 0.000 title claims abstract description 138
- 229920001721 polyimide Polymers 0.000 title claims abstract description 119
- 229920005575 poly(amic acid) Polymers 0.000 title claims abstract description 93
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 19
- 239000004952 Polyamide Substances 0.000 title 1
- 229920002647 polyamide Polymers 0.000 title 1
- 239000004642 Polyimide Substances 0.000 claims abstract description 98
- 239000000047 product Substances 0.000 claims abstract description 85
- 239000000126 substance Substances 0.000 claims abstract description 48
- -1 diamine compound Chemical class 0.000 claims abstract description 43
- 150000008065 acid anhydrides Chemical class 0.000 claims abstract description 31
- 125000000524 functional group Chemical group 0.000 claims abstract description 30
- 239000007795 chemical reaction product Substances 0.000 claims abstract description 11
- 238000006482 condensation reaction Methods 0.000 claims abstract description 8
- 239000003054 catalyst Substances 0.000 claims description 50
- 238000004132 cross linking Methods 0.000 claims description 38
- 238000006243 chemical reaction Methods 0.000 claims description 32
- 125000002524 organometallic group Chemical group 0.000 claims description 30
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims description 19
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 19
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims description 19
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 18
- 125000005843 halogen group Chemical group 0.000 claims description 14
- 238000010438 heat treatment Methods 0.000 claims description 13
- 238000000034 method Methods 0.000 claims description 13
- 239000010931 gold Substances 0.000 claims description 12
- 239000010936 titanium Substances 0.000 claims description 12
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 claims description 10
- 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 claims description 10
- 125000003118 aryl group Chemical group 0.000 claims description 10
- 229910052707 ruthenium Inorganic materials 0.000 claims description 10
- 239000003446 ligand Substances 0.000 claims description 9
- ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 claims description 7
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 claims description 7
- 125000003545 alkoxy group Chemical group 0.000 claims description 7
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 claims description 7
- 229910052737 gold Inorganic materials 0.000 claims description 7
- 229910052750 molybdenum Inorganic materials 0.000 claims description 7
- 239000011733 molybdenum Substances 0.000 claims description 7
- 229910052759 nickel Inorganic materials 0.000 claims description 7
- 229910052762 osmium Inorganic materials 0.000 claims description 7
- SYQBFIAQOQZEGI-UHFFFAOYSA-N osmium atom Chemical compound [Os] SYQBFIAQOQZEGI-UHFFFAOYSA-N 0.000 claims description 7
- 229910052763 palladium Inorganic materials 0.000 claims description 7
- 229910052697 platinum Inorganic materials 0.000 claims description 7
- 229910052715 tantalum Inorganic materials 0.000 claims description 7
- GUVRBAGPIYLISA-UHFFFAOYSA-N tantalum atom Chemical compound [Ta] GUVRBAGPIYLISA-UHFFFAOYSA-N 0.000 claims description 7
- 229910052719 titanium Inorganic materials 0.000 claims description 7
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 claims description 7
- 239000010937 tungsten Substances 0.000 claims description 7
- 229910052721 tungsten Inorganic materials 0.000 claims description 7
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims description 6
- 125000000962 organic group Chemical group 0.000 claims description 6
- 125000000041 C6-C10 aryl group Chemical group 0.000 claims description 5
- VSZWPYCFIRKVQL-UHFFFAOYSA-N selanylidenegallium;selenium Chemical compound [Se].[Se]=[Ga].[Se]=[Ga] VSZWPYCFIRKVQL-UHFFFAOYSA-N 0.000 claims description 5
- 239000002253 acid Substances 0.000 claims description 3
- 229910052723 transition metal Inorganic materials 0.000 claims description 3
- 150000003624 transition metals Chemical class 0.000 claims description 3
- 239000012327 Ruthenium complex Substances 0.000 claims description 2
- QCWXUUIWCKQGHC-UHFFFAOYSA-N Zirconium Chemical compound [Zr] QCWXUUIWCKQGHC-UHFFFAOYSA-N 0.000 claims description 2
- 229910052726 zirconium Inorganic materials 0.000 claims description 2
- 239000007859 condensation product Substances 0.000 claims 2
- 239000002243 precursor Substances 0.000 abstract description 2
- 230000015572 biosynthetic process Effects 0.000 description 45
- 238000003786 synthesis reaction Methods 0.000 description 43
- 230000000052 comparative effect Effects 0.000 description 17
- VZSRBBMJRBPUNF-UHFFFAOYSA-N 2-(2,3-dihydro-1H-inden-2-ylamino)-N-[3-oxo-3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propyl]pyrimidine-5-carboxamide Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C(=O)NCCC(N1CC2=C(CC1)NN=N2)=O VZSRBBMJRBPUNF-UHFFFAOYSA-N 0.000 description 15
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 14
- 239000000758 substrate Substances 0.000 description 11
- 239000010408 film Substances 0.000 description 10
- 238000002834 transmittance Methods 0.000 description 9
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 8
- 239000002904 solvent Substances 0.000 description 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 7
- 125000000217 alkyl group Chemical group 0.000 description 6
- 238000005033 Fourier transform infrared spectroscopy Methods 0.000 description 5
- 150000001875 compounds Chemical class 0.000 description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 5
- 229910052757 nitrogen Inorganic materials 0.000 description 5
- 125000003837 (C1-C20) alkyl group Chemical group 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 4
- 150000001336 alkenes Chemical class 0.000 description 4
- 150000008064 anhydrides Chemical group 0.000 description 4
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 4
- 150000003949 imides Chemical class 0.000 description 4
- 230000000704 physical effect Effects 0.000 description 4
- WLPUWLXVBWGYMZ-UHFFFAOYSA-N tricyclohexylphosphine Chemical compound C1CCCCC1P(C1CCCCC1)C1CCCCC1 WLPUWLXVBWGYMZ-UHFFFAOYSA-N 0.000 description 4
- QMMFVYPAHWMCMS-UHFFFAOYSA-N Dimethyl sulfide Chemical compound CSC QMMFVYPAHWMCMS-UHFFFAOYSA-N 0.000 description 3
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 150000001408 amides Chemical class 0.000 description 3
- 229910052801 chlorine Inorganic materials 0.000 description 3
- 238000000113 differential scanning calorimetry Methods 0.000 description 3
- UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 3
- 238000005755 formation reaction Methods 0.000 description 3
- 125000005842 heteroatom Chemical group 0.000 description 3
- 125000000623 heterocyclic group Chemical group 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 3
- 125000001827 mesitylenyl group Chemical group [H]C1=C(C(*)=C(C([H])=C1C([H])([H])[H])C([H])([H])[H])C([H])([H])[H] 0.000 description 3
- 229920000642 polymer Polymers 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- 125000001424 substituent group Chemical group 0.000 description 3
- RUKVGXGTVPPWDD-UHFFFAOYSA-N 1,3-bis(2,4,6-trimethylphenyl)imidazolidine Chemical compound CC1=CC(C)=CC(C)=C1N1CN(C=2C(=CC(C)=CC=2C)C)CC1 RUKVGXGTVPPWDD-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
- 238000001157 Fourier transform infrared spectrum Methods 0.000 description 2
- LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 description 2
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
- 238000005481 NMR spectroscopy Methods 0.000 description 2
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 2
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 2
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- 125000003342 alkenyl group Chemical group 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 125000001309 chloro group Chemical group Cl* 0.000 description 2
- 125000004122 cyclic group Chemical group 0.000 description 2
- 238000011161 development Methods 0.000 description 2
- 239000000539 dimer Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- DNJIEGIFACGWOD-UHFFFAOYSA-N ethanethiol Chemical compound CCS DNJIEGIFACGWOD-UHFFFAOYSA-N 0.000 description 2
- 229910052731 fluorine Inorganic materials 0.000 description 2
- 125000001153 fluoro group Chemical group F* 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 238000009616 inductively coupled plasma Methods 0.000 description 2
- 239000004973 liquid crystal related substance Substances 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 238000005649 metathesis reaction Methods 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 230000003287 optical effect Effects 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- 229910052698 phosphorus Inorganic materials 0.000 description 2
- 239000011574 phosphorus Substances 0.000 description 2
- 239000004033 plastic Substances 0.000 description 2
- 238000006068 polycondensation reaction Methods 0.000 description 2
- 238000006116 polymerization reaction Methods 0.000 description 2
- 230000009257 reactivity Effects 0.000 description 2
- 238000007152 ring opening metathesis polymerisation reaction Methods 0.000 description 2
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 2
- IGNTWNVBGLNYDV-UHFFFAOYSA-N triisopropylphosphine Chemical compound CC(C)P(C(C)C)C(C)C IGNTWNVBGLNYDV-UHFFFAOYSA-N 0.000 description 2
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 2
- YWWDBCBWQNCYNR-UHFFFAOYSA-N trimethylphosphine Chemical compound CP(C)C YWWDBCBWQNCYNR-UHFFFAOYSA-N 0.000 description 2
- 125000006735 (C1-C20) heteroalkyl group Chemical group 0.000 description 1
- 125000006649 (C2-C20) alkynyl group Chemical group 0.000 description 1
- 125000006736 (C6-C20) aryl group Chemical group 0.000 description 1
- 125000006739 (C7-C20) heteroarylalkyl group Chemical group 0.000 description 1
- WMKGGPCROCCUDY-UHFFFAOYSA-N 1,5-diphenylpenta-1,4-dien-3-one Chemical compound C=1C=CC=CC=1C=CC(=O)C=CC1=CC=CC=C1 WMKGGPCROCCUDY-UHFFFAOYSA-N 0.000 description 1
- XUSNPFGLKGCWGN-UHFFFAOYSA-N 3-[4-(3-aminopropyl)piperazin-1-yl]propan-1-amine Chemical compound NCCCN1CCN(CCCN)CC1 XUSNPFGLKGCWGN-UHFFFAOYSA-N 0.000 description 1
- WCXGOVYROJJXHA-UHFFFAOYSA-N 3-[4-[4-(3-aminophenoxy)phenyl]sulfonylphenoxy]aniline Chemical compound NC1=CC=CC(OC=2C=CC(=CC=2)S(=O)(=O)C=2C=CC(OC=3C=C(N)C=CC=3)=CC=2)=C1 WCXGOVYROJJXHA-UHFFFAOYSA-N 0.000 description 1
- QQGYZOYWNCKGEK-UHFFFAOYSA-N 5-[(1,3-dioxo-2-benzofuran-5-yl)oxy]-2-benzofuran-1,3-dione Chemical compound C1=C2C(=O)OC(=O)C2=CC(OC=2C=C3C(=O)OC(C3=CC=2)=O)=C1 QQGYZOYWNCKGEK-UHFFFAOYSA-N 0.000 description 1
- ZHBXLZQQVCDGPA-UHFFFAOYSA-N 5-[(1,3-dioxo-2-benzofuran-5-yl)sulfonyl]-2-benzofuran-1,3-dione Chemical compound C1=C2C(=O)OC(=O)C2=CC(S(=O)(=O)C=2C=C3C(=O)OC(C3=CC=2)=O)=C1 ZHBXLZQQVCDGPA-UHFFFAOYSA-N 0.000 description 1
- ROFVEXUMMXZLPA-UHFFFAOYSA-N Bipyridyl Chemical group N1=CC=CC=C1C1=CC=CC=N1 ROFVEXUMMXZLPA-UHFFFAOYSA-N 0.000 description 1
- 125000003358 C2-C20 alkenyl group Chemical group 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- 239000004971 Cross linker Substances 0.000 description 1
- RPNUMPOLZDHAAY-UHFFFAOYSA-N Diethylenetriamine Chemical compound NCCNCCN RPNUMPOLZDHAAY-UHFFFAOYSA-N 0.000 description 1
- VURFVHCLMJOLKN-UHFFFAOYSA-N Diphosphine Natural products PP VURFVHCLMJOLKN-UHFFFAOYSA-N 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 1
- 241000282414 Homo sapiens Species 0.000 description 1
- WRYCSMQKUKOKBP-UHFFFAOYSA-N Imidazolidine Chemical compound C1CNCN1 WRYCSMQKUKOKBP-UHFFFAOYSA-N 0.000 description 1
- KWYHDKDOAIKMQN-UHFFFAOYSA-N N,N,N',N'-tetramethylethylenediamine Chemical compound CN(C)CCN(C)C KWYHDKDOAIKMQN-UHFFFAOYSA-N 0.000 description 1
- NIPNSKYNPDTRPC-UHFFFAOYSA-N N-[2-oxo-2-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethyl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C(CNC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)N1CC2=C(CC1)NN=N2 NIPNSKYNPDTRPC-UHFFFAOYSA-N 0.000 description 1
- AFCARXCZXQIEQB-UHFFFAOYSA-N N-[3-oxo-3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propyl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C(CCNC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)N1CC2=C(CC1)NN=N2 AFCARXCZXQIEQB-UHFFFAOYSA-N 0.000 description 1
- ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 description 1
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical group OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 description 1
- DGEZNRSVGBDHLK-UHFFFAOYSA-N [1,10]phenanthroline Chemical compound C1=CN=C2C3=NC=CC=C3C=CC2=C1 DGEZNRSVGBDHLK-UHFFFAOYSA-N 0.000 description 1
- 125000004018 acid anhydride group Chemical group 0.000 description 1
- 150000004703 alkoxides Chemical class 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 150000004984 aromatic diamines Chemical class 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 230000002902 bimodal effect Effects 0.000 description 1
- ZDZHCHYQNPQSGG-UHFFFAOYSA-N binaphthyl group Chemical group C1(=CC=CC2=CC=CC=C12)C1=CC=CC2=CC=CC=C12 ZDZHCHYQNPQSGG-UHFFFAOYSA-N 0.000 description 1
- 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 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000003739 carbamimidoyl group Chemical group C(N)(=N)* 0.000 description 1
- 125000002837 carbocyclic group Chemical group 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 238000010924 continuous production Methods 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 239000003431 cross linking reagent Substances 0.000 description 1
- 125000004093 cyano group Chemical group *C#N 0.000 description 1
- 238000006352 cycloaddition reaction Methods 0.000 description 1
- 150000001925 cycloalkenes Chemical class 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- 150000004985 diamines Chemical class 0.000 description 1
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 1
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
- 229940043279 diisopropylamine Drugs 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- OAKJQQAXSVQMHS-UHFFFAOYSA-N hydrazine group Chemical group NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 1
- 125000005597 hydrazone group Chemical group 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 229910010272 inorganic material Inorganic materials 0.000 description 1
- 239000011147 inorganic material Substances 0.000 description 1
- 230000031700 light absorption Effects 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- HZVOZRGWRWCICA-UHFFFAOYSA-N methanediyl Chemical compound [CH2] HZVOZRGWRWCICA-UHFFFAOYSA-N 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
- 239000012788 optical film Substances 0.000 description 1
- 239000011368 organic material Substances 0.000 description 1
- 238000012536 packaging technology Methods 0.000 description 1
- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 1
- 229910000073 phosphorus hydride Inorganic materials 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 229920000768 polyamine Polymers 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- 239000011253 protective coating Substances 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 238000011002 quantification Methods 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 229960004889 salicylic acid Drugs 0.000 description 1
- 238000007789 sealing Methods 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 125000000542 sulfonic acid group Chemical group 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 150000003464 sulfur compounds Chemical class 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 125000005270 trialkylamine group Chemical group 0.000 description 1
- TUQOTMZNTHZOKS-UHFFFAOYSA-N tributylphosphine Chemical compound CCCCP(CCCC)CCCC TUQOTMZNTHZOKS-UHFFFAOYSA-N 0.000 description 1
- RXJKFRMDXUJTEX-UHFFFAOYSA-N triethylphosphine Chemical compound CCP(CC)CC RXJKFRMDXUJTEX-UHFFFAOYSA-N 0.000 description 1
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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
- C08G73/1075—Partially aromatic polyimides
- C08G73/1078—Partially aromatic polyimides wholly aromatic in the diamino moiety
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- 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
- C08G73/1046—Polyimides containing oxygen in the form of ether bonds in the main chain
- C08G73/105—Polyimides containing oxygen in the form of ether bonds in the main chain with oxygen only in the diamino moiety
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- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J2379/00—Characterised by the use of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing nitrogen with or without oxygen, or carbon only, not provided for in groups C08J2361/00 - C08J2377/00
- C08J2379/04—Polycondensates having nitrogen-containing heterocyclic rings in the main chain; Polyhydrazides; Polyamide acids or similar polyimide precursors
- C08J2379/08—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
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Abstract
【解決手段】金属と、下記化学式1の酸無水物とジアミン化合物との縮合反応生成物であるポリアミック酸の架橋体とを含む金属含有ポリアミック酸の架橋体。
前記式中、Cy環は、架橋可能な官能基を有するC5−C20の炭素環または架橋可能な官能基を有するC4−C20のヘテロ環である。
【選択図】なし
Description
Cl及びBrなどのハロゲン原子;
メチル基、エチル基、イソプロピル基、ブチル基などのC1−C20のアルキル基;
置換または非置換のフェニル基、トリル基、メシチル基などのC6−C20の芳香族基;
アンモニア、モノ−、ジ−、トリアルキルアミンなどのアミン系、メチルアミン、エチルアミン、ジメチルアミン、ジエチルアミン、ジイソプロピルアミン、トリメチルアミン、トリエチルアミン、エチレンジアミン、テトラメチルエチレンジアミン、ジエチレントリアミンなどのポリアミン系物質を含むヘテロ原子含有リガンド;
ピリジン系、ピペリジン系、イミダ系、ピロリジン系、ピペリジン系、ピラジン系、N,N’−二置換のイミダゾリジンなどのイミダゾリジン、N,N’−ジメシチルイミダゾリジンなどのイミダゾリジニリデン系、オキサゾール系、チアゾール系;
アルコキシド、ハロアルコキシドなどの酸素含有リガンド、
メタンチオール、エタンチオール、硫化ジメチルなどの硫黄化合物;
トリメチルホスフィン、トリエチルホスフィン、トリイソプロピルホスフィン、トリブチルホスフィン、トリシクロヘキシルホスフィン、置換または非置換のアミノアルキルジシクロヘキシルホスフィンまたは第4級アンモニウム塩を含むヘテロシクロアルキルジシクロヘキシルホスフィンなどのリン含有リガンド、
サリチル酸、サリチルイミド、ビピリジル、エチレン(ビスジフェニルホスフィン)、ジホスフィンビナフチルを含むビナフチルなどのジホスフィン系、フェナントロリン系、ビス(ジベンジリデン)アセトンなどのビ−またはマルチデンテートリガンド;などを挙げることができる。
Aは、
nは、10ないし500の数である。
Aは、
Aは、
化学式3の化合物0.6437g(2.593mmol)をDMAc 8.5mlに溶かし、これを、化学式4のBAPS 1.0656g(2.463mmol)をDMAc 8.5mlに溶かした溶液に添加及び混合して、これを常温で18時間反応させてポリアミック酸を得た。
金属含有ポリアミック酸の架橋体の製造時、有機金属触媒であるベンジリデン[1,3−ビス(2,4,6−トリメチルフェニル)−2−イミダゾリジニリデン]ジクロロ(トリシクロホスフィン)ルテニウムの含量が0.00855gが使われて、金属触媒(有機金属触媒由来の金属)の含有量が、ポリアミック酸と触媒との総重量を基準として0.05wt%に変わったことを除いては、合成例1−1と同じ方法によって実施して、金属含有ポリイミドの架橋体を製造した。
金属含有ポリアミック酸の架橋体の製造時、有機金属触媒であるベンジリデン[1,3−ビス(2,4,6−トリメチルフェニル)−2−イミダゾリジニリデン]ジクロロ(トリシクロホスフィン)ルテニウムの含量が0.00171gが使われて、金属触媒(有機金属触媒由来の金属)の含有量が、ポリアミック酸と触媒との総重量を基準として0.01wt%に変わったことを除いては、合成例1−1と同じ方法によって実施して、金属含有ポリイミドの架橋体を製造した。
化学式3の化合物0.6437g(2.593mmol)をDMAc 8.5mlに溶かし、これを、化学式4のBAPS 1.0656g(2.463mmol)をDMAc 8.5mlに溶かした溶液に添加及び混合し、これを常温で18時間反応してポリアミック酸を得た。
化学式3の化合物0.6437g(2.593mmol)をDMAc 8.5mlに溶かし、これを、化学式4のBAPS 1.0656g(2.463mmol)をDMAc 8.5mlに溶かした溶液に添加及び混合し、これを常温で18時間反応してポリアミック酸を得た。
Claims (25)
- 金属と、
下記化学式1の酸無水物とジアミン化合物との縮合反応生成物であるポリアミック酸の架橋体とを含む金属含有ポリアミック酸の架橋体:
- 前記
前記式中、Rは、水素原子、C1−C10のアルキル基、C1−C10のアルキルオキシ基、C6−C10のアリール基またはハロゲン原子であることを特徴とする請求項1に記載の金属含有ポリアミック酸の架橋体。 - 前記ジアミン化合物は、下記化学式2で表示されるジアミン化合物である請求項1または2に記載の金属含有ポリアミック酸の架橋体:
- 前記金属は、ルテニウム(Ru)、タングステン(W)、モリブデン(Mo)、オスミウム(Os)、チタン(Ti)、ニッケル(Ni)、タンタル(Ta)、ジルコニウム(Zr)、白金(Pt)、パラジウム(Pd)および金(Au)よりなる群から選択された一つ以上である請求項1〜3のいずれかに記載の金属含有ポリアミック酸の架橋体。
- 前記金属の含有量は、金属含有ポリアミック酸の架橋体を基準として0.0001ないし2.5wt%である請求項1〜4のいずれかに記載の金属含有ポリアミック酸の架橋体。
- 架橋可能な官能基を有していない化学式21の付加的な二無水物をさらに含む請求項1〜5のいずれかに記載の金属含有ポリアミック酸の架橋体:
- 金属と、
下記化学式1の酸無水物とジアミン化合物との縮合反応及びイミド化の生成物であるポリイミドの架橋体とを含む金属含有ポリイミドの架橋体:
- 前記
前記式中、Rは、水素原子、C1−C10のアルキル基、C1−C10のアルキルオキシ基、C6−C10のアリール基またはハロゲン原子である請求項7に記載の金属含有ポリイミドの架橋体。 - 前記ジアミン化合物は、下記化学式2で表示されるジアミン化合物である請求項7または8に記載の金属含有ポリイミドの架橋体:
- 前記金属は、ルテニウム(Ru)、タングステン(W)、モリブデン(Mo)、オスミウム(Os)、チタン(Ti)、ニッケル(Ni)、タンタル(Ta)、ジルコニウム(Zr)、白金(Pt)、パラジウム(Pd)および金(Au)よりなる群から選択された一つ以上である請求項7〜9のいずれかに記載の金属含有ポリイミドの架橋体。
- 前記金属の含有量は、金属含有ポリイミドの架橋体を基準として0.0001ないし2.5wt%であることを特徴とする請求項7〜10のいずれかに記載の金属含有ポリイミドの架橋体。
- 架橋可能な官能基を有していない化学式21の付加的な二無水物をさらに含む請求項7〜11のいずれかに記載の金属含有ポリイミドの架橋体:
- 下記化学式1で表示される酸無水物とジアミン化合物との縮合反応を実施してポリアミック酸を形成する工程と、
前記ポリアミック酸を有機金属触媒下で低温架橋反応を実施して、金属含有ポリアミック酸の架橋体を形成する工程と、
前記金属含有ポリアミック酸の架橋体を熱処理してイミド化する工程とを含む、金属含有ポリイミドの架橋体を得る金属含有ポリイミドの架橋体の製造方法:
- 前記有機金属触媒が、ルテニウム系錯体、タングステン系錯体、モリブデン系錯体、オスミウム系錯体、ニッケル系錯体、チタン系錯体、タンタル系錯体、ジルコニウム系錯体、白金系錯体、パラジウム系錯体および金系錯体よりなる群から選択された一つ以上である請求項13に記載の金属含有ポリイミドの架橋体の製造方法。
- 前記低温架橋反応が、20℃ないし150℃で行われる請求項13または14に記載の金属含有ポリイミドの架橋体の製造方法。
- 前記イミド化工程以前に、80ないし250℃で熱処理する工程を経る請求項13〜15のいずれかに記載の金属含有ポリイミドの架橋体の製造方法。
- 前記イミド化工程以前に、0.000001ないし0.1atm、80ないし250℃で熱処理する工程を経る請求項13〜16のいずれかに記載の金属含有ポリイミドの架橋体の製造方法。
- 前記イミド化工程の熱処理が、200ないし270℃で行われる請求項13〜17のいずれかに記載の金属含有ポリイミドの架橋体の製造方法。
- 前記ジアミン化合物が、下記化学式2で表示されるジアミン化合物である請求項13〜18のいずれかに記載の金属含有ポリイミドの架橋体の製造方法:
- 金属と、
下記化学式1の酸無水物とジアミン化合物との縮合反応及びイミド化の生成物であるポリイミドの架橋体とを含む金属含有ポリイミドの架橋体を含むポリイミドフィルム:
- 前記
前記式中、Rは、水素原子、C1−C10のアルキル基、C1−C10のアルキルオキシ基、C6−C10のアリール基またはハロゲン原子である請求項20に記載のポリイミドフィルム。 - 前記ジアミン化合物が、下記化学式2で表示されるジアミン化合物である請求項20または21に記載のポリイミドフィルム:
- 前記金属は、ルテニウム(Ru)、タングステン(W)、モリブデン(Mo)、オスミウム(Os)、チタン(Ti)、ニッケル(Ni)、タンタル(Ta)、ジルコニウム(Zr)、白金(Pt)、パラジウム(Pd)および金(Au)よりなる群から選択された一つ以上である請求項20〜22のいずれかに記載のポリイミドフィルム。
- 前記金属の含有量は、金属含有ポリイミドの架橋体を基準として0.0001ないし2.5wt%であることを特徴とする請求項20〜23のいずれかに記載のポリイミドフィルム。
- 化学式1で表示される酸無水物、化学式2で表示されるジアミン化合物、及び化学式20で表示される有機金属触媒の反応生成物として、前記酸無水物とジアミン化合物からポリアミック酸が形成され、前記ポリアミック酸が前記有機金属触媒の存在下で架橋されて、金属含有ポリアミック酸の架橋体が形成され、前記金属含有ポリアミック酸の架橋体を熱処理及びイミド化して、金属含有ポリイミドの架橋体が形成されてなる反応生成物:
Lはリガンドであり、
nは1ないし5の整数であり、
Rは水素原子または有機基である。
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