JPWO2017209197A1 - ポリイミド前駆体、ポリイミド、ポリイミドフィルム、及び基板、並びにポリイミドの製造に使用されるテトラカルボン酸二無水物 - Google Patents
ポリイミド前駆体、ポリイミド、ポリイミドフィルム、及び基板、並びにポリイミドの製造に使用されるテトラカルボン酸二無水物 Download PDFInfo
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- JPWO2017209197A1 JPWO2017209197A1 JP2018520967A JP2018520967A JPWO2017209197A1 JP WO2017209197 A1 JPWO2017209197 A1 JP WO2017209197A1 JP 2018520967 A JP2018520967 A JP 2018520967A JP 2018520967 A JP2018520967 A JP 2018520967A JP WO2017209197 A1 JPWO2017209197 A1 JP WO2017209197A1
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- following chemical
- polyimide
- reaction
- Prior art date
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- 229920001721 polyimide Polymers 0.000 title claims abstract description 311
- 239000004642 Polyimide Substances 0.000 title claims abstract description 225
- 239000002243 precursor Substances 0.000 title claims abstract description 138
- 239000000758 substrate Substances 0.000 title claims description 58
- 238000002360 preparation method Methods 0.000 title description 2
- 239000000126 substance Substances 0.000 claims abstract description 278
- 150000000000 tetracarboxylic acids Chemical class 0.000 claims abstract description 85
- -1 olefin compound Chemical class 0.000 claims description 151
- 238000000034 method Methods 0.000 claims description 69
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 68
- 239000003960 organic solvent Substances 0.000 claims description 64
- 125000003118 aryl group Chemical group 0.000 claims description 45
- 150000001875 compounds Chemical class 0.000 claims description 43
- 125000000217 alkyl group Chemical group 0.000 claims description 37
- 230000008569 process Effects 0.000 claims description 36
- 239000003054 catalyst Substances 0.000 claims description 35
- 229910052763 palladium Inorganic materials 0.000 claims description 34
- 239000002253 acid Substances 0.000 claims description 32
- 125000004432 carbon atom Chemical group C* 0.000 claims description 32
- 239000003795 chemical substances by application Substances 0.000 claims description 25
- 239000005749 Copper compound Substances 0.000 claims description 23
- 150000001880 copper compounds Chemical class 0.000 claims description 23
- 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 19
- 239000003377 acid catalyst Substances 0.000 claims description 18
- 239000002966 varnish Substances 0.000 claims description 18
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 17
- 239000001257 hydrogen Substances 0.000 claims description 17
- 229910052739 hydrogen Inorganic materials 0.000 claims description 17
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 17
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims description 16
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 15
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 claims description 14
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 claims description 13
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 claims description 12
- 229910002091 carbon monoxide Inorganic materials 0.000 claims description 12
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims description 11
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 11
- 229910052751 metal Inorganic materials 0.000 claims description 11
- 239000002184 metal Substances 0.000 claims description 11
- 125000002723 alicyclic group Chemical group 0.000 claims description 10
- 125000005103 alkyl silyl group Chemical group 0.000 claims description 10
- 125000001931 aliphatic group Chemical group 0.000 claims description 9
- 229910052799 carbon Inorganic materials 0.000 claims description 9
- 150000008064 anhydrides Chemical class 0.000 claims description 7
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims description 7
- 125000006158 tetracarboxylic acid group Chemical group 0.000 claims description 7
- 238000007254 oxidation reaction Methods 0.000 claims description 6
- 125000001424 substituent group Chemical group 0.000 claims description 5
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 5
- 150000008065 acid anhydrides Chemical class 0.000 claims description 3
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 claims description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
- 238000006243 chemical reaction Methods 0.000 description 251
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 127
- 150000004985 diamines Chemical class 0.000 description 112
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 96
- 239000002904 solvent Substances 0.000 description 92
- 239000000243 solution Substances 0.000 description 91
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 88
- 239000007787 solid Substances 0.000 description 82
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 81
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 70
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 63
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 62
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 56
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 51
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 50
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 49
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 48
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 48
- 239000000203 mixture Substances 0.000 description 48
- 238000003756 stirring Methods 0.000 description 47
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 45
- 238000005160 1H NMR spectroscopy Methods 0.000 description 43
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- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 40
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 40
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- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 32
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 32
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 32
- ZSWFCLXCOIISFI-UHFFFAOYSA-N cyclopentadiene Chemical compound C1C=CC=C1 ZSWFCLXCOIISFI-UHFFFAOYSA-N 0.000 description 31
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 30
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 description 27
- 238000010438 heat treatment Methods 0.000 description 27
- 239000011521 glass Substances 0.000 description 26
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 25
- 238000000262 chemical ionisation mass spectrometry Methods 0.000 description 25
- 239000010408 film Substances 0.000 description 25
- 229910052757 nitrogen Inorganic materials 0.000 description 25
- 230000000704 physical effect Effects 0.000 description 25
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 24
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 24
- 150000001298 alcohols Chemical class 0.000 description 24
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 24
- 239000005340 laminated glass Substances 0.000 description 24
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 24
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 22
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 22
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 21
- 239000002585 base Substances 0.000 description 21
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 20
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 20
- 150000001408 amides Chemical class 0.000 description 20
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 20
- DKGAVHZHDRPRBM-UHFFFAOYSA-N tertiry butyl alcohol Natural products CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 20
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 19
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 19
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 18
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 18
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 18
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 18
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 18
- 239000008096 xylene Substances 0.000 description 18
- 238000004458 analytical method Methods 0.000 description 17
- 235000013877 carbamide Nutrition 0.000 description 17
- 239000010410 layer Substances 0.000 description 17
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 17
- 150000003672 ureas Chemical class 0.000 description 17
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 16
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 16
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 16
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 16
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 16
- 150000002170 ethers Chemical class 0.000 description 16
- 150000008282 halocarbons Chemical class 0.000 description 16
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 16
- 238000004519 manufacturing process Methods 0.000 description 16
- 150000002825 nitriles Chemical class 0.000 description 16
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 16
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 15
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 15
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 15
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 15
- 235000019253 formic acid Nutrition 0.000 description 15
- HLBLWEWZXPIGSM-UHFFFAOYSA-N 4-Aminophenyl ether Chemical compound C1=CC(N)=CC=C1OC1=CC=C(N)C=C1 HLBLWEWZXPIGSM-UHFFFAOYSA-N 0.000 description 14
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 14
- 239000000178 monomer Substances 0.000 description 14
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- 150000007513 acids Chemical class 0.000 description 13
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- 239000000706 filtrate Substances 0.000 description 13
- 238000002156 mixing Methods 0.000 description 13
- 239000001301 oxygen Substances 0.000 description 13
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- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
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- 238000001914 filtration Methods 0.000 description 12
- 239000012528 membrane Substances 0.000 description 12
- 239000012299 nitrogen atmosphere Substances 0.000 description 12
- 229920005575 poly(amic acid) Polymers 0.000 description 12
- 239000004810 polytetrafluoroethylene Substances 0.000 description 12
- 229920001343 polytetrafluoroethylene Polymers 0.000 description 12
- 150000003457 sulfones Chemical class 0.000 description 12
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- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 11
- ORTQZVOHEJQUHG-UHFFFAOYSA-L copper(II) chloride Chemical compound Cl[Cu]Cl ORTQZVOHEJQUHG-UHFFFAOYSA-L 0.000 description 11
- 229910052500 inorganic mineral Inorganic materials 0.000 description 11
- 235000010755 mineral Nutrition 0.000 description 11
- 239000011707 mineral Substances 0.000 description 11
- 238000000746 purification Methods 0.000 description 11
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- 235000017557 sodium bicarbonate Nutrition 0.000 description 10
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- 239000012298 atmosphere Substances 0.000 description 9
- 230000015572 biosynthetic process Effects 0.000 description 9
- 150000001733 carboxylic acid esters Chemical class 0.000 description 9
- 230000000052 comparative effect Effects 0.000 description 9
- VHILMKFSCRWWIJ-UHFFFAOYSA-N dimethyl acetylenedicarboxylate Chemical compound COC(=O)C#CC(=O)OC VHILMKFSCRWWIJ-UHFFFAOYSA-N 0.000 description 9
- 229940098779 methanesulfonic acid Drugs 0.000 description 9
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- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 8
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- 239000007795 chemical reaction product Substances 0.000 description 8
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- 238000004817 gas chromatography Methods 0.000 description 8
- FFUAGWLWBBFQJT-UHFFFAOYSA-N hexamethyldisilazane Chemical compound C[Si](C)(C)N[Si](C)(C)C FFUAGWLWBBFQJT-UHFFFAOYSA-N 0.000 description 8
- 150000002576 ketones Chemical class 0.000 description 8
- KJIFKLIQANRMOU-UHFFFAOYSA-N oxidanium;4-methylbenzenesulfonate Chemical compound O.CC1=CC=C(S(O)(=O)=O)C=C1 KJIFKLIQANRMOU-UHFFFAOYSA-N 0.000 description 8
- 239000007800 oxidant agent Substances 0.000 description 8
- SMUQFGGVLNAIOZ-UHFFFAOYSA-N quinaldine Chemical compound C1=CC=CC2=NC(C)=CC=C21 SMUQFGGVLNAIOZ-UHFFFAOYSA-N 0.000 description 8
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- PYOKUURKVVELLB-UHFFFAOYSA-N trimethyl orthoformate Chemical compound COC(OC)OC PYOKUURKVVELLB-UHFFFAOYSA-N 0.000 description 8
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- 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 7
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 7
- 229910052783 alkali metal Inorganic materials 0.000 description 7
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 7
- 229910052794 bromium Inorganic materials 0.000 description 7
- 150000002148 esters Chemical class 0.000 description 7
- 229910052736 halogen Inorganic materials 0.000 description 7
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- HWTDMFJYBAURQR-UHFFFAOYSA-N 80-82-0 Chemical compound OS(=O)(=O)C1=CC=CC=C1[N+]([O-])=O HWTDMFJYBAURQR-UHFFFAOYSA-N 0.000 description 1
- XRYJJJJNCOBNEY-UHFFFAOYSA-N 9-oxatricyclo[4.2.1.02,5]nonane-3,4,7,8-tetracarboxylic acid Chemical compound O1C2C3C(C(=O)O)C(C(O)=O)C3C1C(C(O)=O)C2C(O)=O XRYJJJJNCOBNEY-UHFFFAOYSA-N 0.000 description 1
- FIPWRIJSWJWJAI-UHFFFAOYSA-N Butyl carbitol 6-propylpiperonyl ether Chemical compound C1=C(CCC)C(COCCOCCOCCCC)=CC2=C1OCO2 FIPWRIJSWJWJAI-UHFFFAOYSA-N 0.000 description 1
- BMTAFVWTTFSTOG-UHFFFAOYSA-N Butylate Chemical compound CCSC(=O)N(CC(C)C)CC(C)C BMTAFVWTTFSTOG-UHFFFAOYSA-N 0.000 description 1
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 1
- 244000201986 Cassia tora Species 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- JJLJMEJHUUYSSY-UHFFFAOYSA-L Copper hydroxide Chemical compound [OH-].[OH-].[Cu+2] JJLJMEJHUUYSSY-UHFFFAOYSA-L 0.000 description 1
- 239000005750 Copper hydroxide Substances 0.000 description 1
- 239000005751 Copper oxide Substances 0.000 description 1
- 229910021589 Copper(I) bromide Inorganic materials 0.000 description 1
- 229910021591 Copper(I) chloride Inorganic materials 0.000 description 1
- 229910021590 Copper(II) bromide Inorganic materials 0.000 description 1
- 229920001076 Cutan Polymers 0.000 description 1
- ZPAKUZKMGJJMAA-UHFFFAOYSA-N Cyclohexane-1,2,4,5-tetracarboxylic acid Chemical compound OC(=O)C1CC(C(O)=O)C(C(O)=O)CC1C(O)=O ZPAKUZKMGJJMAA-UHFFFAOYSA-N 0.000 description 1
- 239000004805 Cyclohexane-1,2-dicarboxylic acid Substances 0.000 description 1
- MQJKPEGWNLWLTK-UHFFFAOYSA-N Dapsone Chemical compound C1=CC(N)=CC=C1S(=O)(=O)C1=CC=C(N)C=C1 MQJKPEGWNLWLTK-UHFFFAOYSA-N 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- QZRGKCOWNLSUDK-UHFFFAOYSA-N Iodochlorine Chemical compound ICl QZRGKCOWNLSUDK-UHFFFAOYSA-N 0.000 description 1
- 229910021578 Iron(III) chloride Inorganic materials 0.000 description 1
- 239000012359 Methanesulfonyl chloride Substances 0.000 description 1
- IOVCWXUNBOPUCH-UHFFFAOYSA-N Nitrous acid Chemical compound ON=O IOVCWXUNBOPUCH-UHFFFAOYSA-N 0.000 description 1
- LQOPXMZSGSTGMF-UHFFFAOYSA-N O=C(C1C2C3CC1CC3)OC2=O Chemical compound O=C(C1C2C3CC1CC3)OC2=O LQOPXMZSGSTGMF-UHFFFAOYSA-N 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- 239000004952 Polyamide Substances 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 229910000564 Raney nickel Inorganic materials 0.000 description 1
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 description 1
- DTQVDTLACAAQTR-UHFFFAOYSA-M Trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-M 0.000 description 1
- DSVGQVZAZSZEEX-UHFFFAOYSA-N [C].[Pt] Chemical compound [C].[Pt] DSVGQVZAZSZEEX-UHFFFAOYSA-N 0.000 description 1
- RAOSIAYCXKBGFE-UHFFFAOYSA-K [Cu+3].[O-]P([O-])([O-])=O Chemical compound [Cu+3].[O-]P([O-])([O-])=O RAOSIAYCXKBGFE-UHFFFAOYSA-K 0.000 description 1
- GPWHDDKQSYOYBF-UHFFFAOYSA-N ac1l2u0q Chemical class Br[Br-]Br GPWHDDKQSYOYBF-UHFFFAOYSA-N 0.000 description 1
- GOKIPOOTKLLKDI-UHFFFAOYSA-N acetic acid;iron Chemical compound [Fe].CC(O)=O.CC(O)=O.CC(O)=O GOKIPOOTKLLKDI-UHFFFAOYSA-N 0.000 description 1
- 125000005595 acetylacetonate group Chemical group 0.000 description 1
- YBCVMFKXIKNREZ-UHFFFAOYSA-N acoh acetic acid Chemical class CC(O)=O.CC(O)=O YBCVMFKXIKNREZ-UHFFFAOYSA-N 0.000 description 1
- 239000008186 active pharmaceutical agent Substances 0.000 description 1
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 125000003368 amide group Chemical group 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 235000019270 ammonium chloride Nutrition 0.000 description 1
- 238000002048 anodisation reaction Methods 0.000 description 1
- 239000002518 antifoaming agent Substances 0.000 description 1
- 239000000010 aprotic solvent Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 239000011324 bead Substances 0.000 description 1
- ZVSKZLHKADLHSD-UHFFFAOYSA-N benzanilide Chemical compound C=1C=CC=CC=1C(=O)NC1=CC=CC=C1 ZVSKZLHKADLHSD-UHFFFAOYSA-N 0.000 description 1
- SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 description 1
- 229940092714 benzenesulfonic acid Drugs 0.000 description 1
- CSKNSYBAZOQPLR-UHFFFAOYSA-N benzenesulfonyl chloride Chemical compound ClS(=O)(=O)C1=CC=CC=C1 CSKNSYBAZOQPLR-UHFFFAOYSA-N 0.000 description 1
- HFACYLZERDEVSX-UHFFFAOYSA-N benzidine Chemical compound C1=CC(N)=CC=C1C1=CC=C(N)C=C1 HFACYLZERDEVSX-UHFFFAOYSA-N 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- BKDVBBSUAGJUBA-UHFFFAOYSA-N bicyclo[2.2.2]oct-7-ene-2,3,5,6-tetracarboxylic acid Chemical compound C1=CC2C(C(O)=O)C(C(=O)O)C1C(C(O)=O)C2C(O)=O BKDVBBSUAGJUBA-UHFFFAOYSA-N 0.000 description 1
- 230000005540 biological transmission Effects 0.000 description 1
- CODNYICXDISAEA-UHFFFAOYSA-N bromine monochloride Chemical compound BrCl CODNYICXDISAEA-UHFFFAOYSA-N 0.000 description 1
- ODWXUNBKCRECNW-UHFFFAOYSA-M bromocopper(1+) Chemical compound Br[Cu+] ODWXUNBKCRECNW-UHFFFAOYSA-M 0.000 description 1
- 239000001110 calcium chloride Substances 0.000 description 1
- 229910001628 calcium chloride Inorganic materials 0.000 description 1
- 150000001718 carbodiimides Chemical class 0.000 description 1
- 238000003763 carbonization Methods 0.000 description 1
- 238000005266 casting Methods 0.000 description 1
- 239000000919 ceramic Substances 0.000 description 1
- 239000012295 chemical reaction liquid Substances 0.000 description 1
- 239000012320 chlorinating reagent Substances 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 description 1
- 238000004891 communication Methods 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 229910001956 copper hydroxide Inorganic materials 0.000 description 1
- 229910000431 copper oxide Inorganic materials 0.000 description 1
- 229910000365 copper sulfate Inorganic materials 0.000 description 1
- OXBLHERUFWYNTN-UHFFFAOYSA-M copper(I) chloride Chemical compound [Cu]Cl OXBLHERUFWYNTN-UHFFFAOYSA-M 0.000 description 1
- ARUVKPQLZAKDPS-UHFFFAOYSA-L copper(II) sulfate Chemical compound [Cu+2].[O-][S+2]([O-])([O-])[O-] ARUVKPQLZAKDPS-UHFFFAOYSA-L 0.000 description 1
- NKNDPYCGAZPOFS-UHFFFAOYSA-M copper(i) bromide Chemical compound Br[Cu] NKNDPYCGAZPOFS-UHFFFAOYSA-M 0.000 description 1
- DOBRDRYODQBAMW-UHFFFAOYSA-N copper(i) cyanide Chemical compound [Cu+].N#[C-] DOBRDRYODQBAMW-UHFFFAOYSA-N 0.000 description 1
- OPQARKPSCNTWTJ-UHFFFAOYSA-L copper(ii) acetate Chemical compound [Cu+2].CC([O-])=O.CC([O-])=O OPQARKPSCNTWTJ-UHFFFAOYSA-L 0.000 description 1
- SBTSVTLGWRLWOD-UHFFFAOYSA-L copper(ii) triflate Chemical compound [Cu+2].[O-]S(=O)(=O)C(F)(F)F.[O-]S(=O)(=O)C(F)(F)F SBTSVTLGWRLWOD-UHFFFAOYSA-L 0.000 description 1
- ITFUHOHJQIDNQW-UHFFFAOYSA-L copper;2,2-dimethylpropanoate Chemical compound [Cu+2].CC(C)(C)C([O-])=O.CC(C)(C)C([O-])=O ITFUHOHJQIDNQW-UHFFFAOYSA-L 0.000 description 1
- DYROSKSLMAPFBZ-UHFFFAOYSA-L copper;2-hydroxypropanoate Chemical compound [Cu+2].CC(O)C([O-])=O.CC(O)C([O-])=O DYROSKSLMAPFBZ-UHFFFAOYSA-L 0.000 description 1
- KOKFUFYHQQCNNJ-UHFFFAOYSA-L copper;2-methylpropanoate Chemical compound [Cu+2].CC(C)C([O-])=O.CC(C)C([O-])=O KOKFUFYHQQCNNJ-UHFFFAOYSA-L 0.000 description 1
- MRYMYQPDGZIGDM-UHFFFAOYSA-L copper;4-methylbenzenesulfonate Chemical compound [Cu+2].CC1=CC=C(S([O-])(=O)=O)C=C1.CC1=CC=C(S([O-])(=O)=O)C=C1 MRYMYQPDGZIGDM-UHFFFAOYSA-L 0.000 description 1
- PUHAKHQMSBQAKT-UHFFFAOYSA-L copper;butanoate Chemical compound [Cu+2].CCCC([O-])=O.CCCC([O-])=O PUHAKHQMSBQAKT-UHFFFAOYSA-L 0.000 description 1
- GBRBMTNGQBKBQE-UHFFFAOYSA-L copper;diiodide Chemical compound I[Cu]I GBRBMTNGQBKBQE-UHFFFAOYSA-L 0.000 description 1
- LZJJVTQGPPWQFS-UHFFFAOYSA-L copper;propanoate Chemical compound [Cu+2].CCC([O-])=O.CCC([O-])=O LZJJVTQGPPWQFS-UHFFFAOYSA-L 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 125000004122 cyclic group Chemical group 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
- SSJXIUAHEKJCMH-UHFFFAOYSA-N cyclohexane-1,2-diamine Chemical compound NC1CCCCC1N SSJXIUAHEKJCMH-UHFFFAOYSA-N 0.000 description 1
- QSAWQNUELGIYBC-UHFFFAOYSA-N cyclohexane-1,2-dicarboxylic acid Chemical compound OC(=O)C1CCCCC1C(O)=O QSAWQNUELGIYBC-UHFFFAOYSA-N 0.000 description 1
- HRYUOPWKEXOLLL-UHFFFAOYSA-N dec-3-ene-1,2,7,8-tetracarboxylic acid Chemical compound CCC(C(O)=O)C(C(O)=O)CCC=CC(C(O)=O)CC(O)=O HRYUOPWKEXOLLL-UHFFFAOYSA-N 0.000 description 1
- GUIAWEJKSYXUFP-UHFFFAOYSA-N decane-2,3,6,7-tetracarboxylic acid Chemical compound CCC(C(CCC(C(CC)C(=O)O)C(=O)O)C(=O)O)C(=O)O GUIAWEJKSYXUFP-UHFFFAOYSA-N 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 238000007033 dehydrochlorination reaction Methods 0.000 description 1
- 150000001991 dicarboxylic acids Chemical class 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- FVRDWQRPXYJEJK-UHFFFAOYSA-N dimethyl tricyclo[6.2.1.02,7]undeca-2(7),4,9-triene-4,5-dicarboxylate Chemical compound COC(=O)C1=C(CC2=C(C1)C1CC2C=C1)C(=O)OC FVRDWQRPXYJEJK-UHFFFAOYSA-N 0.000 description 1
- SLMNTWPOOQWWIU-UHFFFAOYSA-N diphenyl but-2-ynedioate Chemical compound C=1C=CC=CC=1OC(=O)C#CC(=O)OC1=CC=CC=C1 SLMNTWPOOQWWIU-UHFFFAOYSA-N 0.000 description 1
- OPTPSVGIMYCMQJ-UHFFFAOYSA-N dipropyl but-2-ynedioate Chemical compound CCCOC(=O)C#CC(=O)OCCC OPTPSVGIMYCMQJ-UHFFFAOYSA-N 0.000 description 1
- BXKDSDJJOVIHMX-UHFFFAOYSA-N edrophonium chloride Chemical compound [Cl-].CC[N+](C)(C)C1=CC=CC(O)=C1 BXKDSDJJOVIHMX-UHFFFAOYSA-N 0.000 description 1
- 238000005265 energy consumption Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- FRYHCSODNHYDPU-UHFFFAOYSA-N ethanesulfonyl chloride Chemical compound CCS(Cl)(=O)=O FRYHCSODNHYDPU-UHFFFAOYSA-N 0.000 description 1
- 229920002457 flexible plastic Polymers 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- OMRRUNXAWXNVFW-UHFFFAOYSA-N fluoridochlorine Chemical compound ClF OMRRUNXAWXNVFW-UHFFFAOYSA-N 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 239000006260 foam Substances 0.000 description 1
- 230000009477 glass transition Effects 0.000 description 1
- 150000002366 halogen compounds Chemical class 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 238000007654 immersion Methods 0.000 description 1
- 229910017053 inorganic salt Inorganic materials 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- CBEQRNSPHCCXSH-UHFFFAOYSA-N iodine monobromide Chemical compound IBr CBEQRNSPHCCXSH-UHFFFAOYSA-N 0.000 description 1
- 238000005342 ion exchange Methods 0.000 description 1
- 150000002500 ions Chemical group 0.000 description 1
- RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 description 1
- RUTXIHLAWFEWGM-UHFFFAOYSA-H iron(3+) sulfate Chemical compound [Fe+3].[Fe+3].[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O RUTXIHLAWFEWGM-UHFFFAOYSA-H 0.000 description 1
- 229910000360 iron(III) sulfate Inorganic materials 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 125000000654 isopropylidene group Chemical group C(C)(C)=* 0.000 description 1
- 125000005647 linker group Chemical group 0.000 description 1
- 229940018564 m-phenylenediamine Drugs 0.000 description 1
- 229920002521 macromolecule Polymers 0.000 description 1
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 1
- 239000011259 mixed solution Substances 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 238000010943 off-gassing Methods 0.000 description 1
- 239000013307 optical fiber Substances 0.000 description 1
- 239000011368 organic material Substances 0.000 description 1
- 150000002940 palladium Chemical class 0.000 description 1
- JKDRQYIYVJVOPF-FDGPNNRMSA-L palladium(ii) acetylacetonate Chemical compound [Pd+2].C\C([O-])=C\C(C)=O.C\C([O-])=C\C(C)=O JKDRQYIYVJVOPF-FDGPNNRMSA-L 0.000 description 1
- NCAIGTHBQTXTLR-UHFFFAOYSA-N phentermine hydrochloride Chemical compound [Cl-].CC(C)([NH3+])CC1=CC=CC=C1 NCAIGTHBQTXTLR-UHFFFAOYSA-N 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 238000000206 photolithography Methods 0.000 description 1
- 229960005235 piperonyl butoxide Drugs 0.000 description 1
- 239000002985 plastic film Substances 0.000 description 1
- 229920006255 plastic film Polymers 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 239000002685 polymerization catalyst Substances 0.000 description 1
- 229960003975 potassium Drugs 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000013615 primer Substances 0.000 description 1
- 239000002987 primer (paints) Substances 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- JQRYUMGHOUYJFW-UHFFFAOYSA-N pyridine;trihydrobromide Chemical compound [Br-].[Br-].[Br-].C1=CC=[NH+]C=C1.C1=CC=[NH+]C=C1.C1=CC=[NH+]C=C1 JQRYUMGHOUYJFW-UHFFFAOYSA-N 0.000 description 1
- 238000001226 reprecipitation Methods 0.000 description 1
- 230000000630 rising effect Effects 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 238000006884 silylation reaction Methods 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- ZCJHLBHJGLCVRU-UHFFFAOYSA-N stk208316 Chemical compound C12C(=O)C3C(C=C4)CC4C3C(=O)C2C2C=CC1C2 ZCJHLBHJGLCVRU-UHFFFAOYSA-N 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 230000008961 swelling Effects 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- ITYJXDJNDNGLGA-UHFFFAOYSA-N tetramethyl tetracyclo[6.2.2.13,6.02,7]tridec-11-ene-4,5,9,10-tetracarboxylate Chemical compound COC(=O)C1C2C3C4C=CC(C3C(C1C(=O)OC)C2)C(C4C(=O)OC)C(=O)OC ITYJXDJNDNGLGA-UHFFFAOYSA-N 0.000 description 1
- KXTNCNQBUZFKQZ-UHFFFAOYSA-N tetramethyl tetracyclo[6.2.2.13,6.02,7]tridecane-4,5,9,10-tetracarboxylate Chemical compound COC(=O)C1C2C3C4C(C(C(C3C(C1C(=O)OC)CC2)C4)C(=O)OC)C(=O)OC KXTNCNQBUZFKQZ-UHFFFAOYSA-N 0.000 description 1
- 238000005979 thermal decomposition reaction Methods 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- 150000003628 tricarboxylic acids Chemical class 0.000 description 1
- GKASDNZWUGIAMG-UHFFFAOYSA-N triethyl orthoformate Chemical compound CCOC(OCC)OCC GKASDNZWUGIAMG-UHFFFAOYSA-N 0.000 description 1
- GRGCWBWNLSTIEN-UHFFFAOYSA-N trifluoromethanesulfonyl chloride Chemical compound FC(F)(F)S(Cl)(=O)=O GRGCWBWNLSTIEN-UHFFFAOYSA-N 0.000 description 1
- FNZBSNUICNVAAM-UHFFFAOYSA-N trimethyl-[methyl-[methyl-(methyl-phenyl-trimethylsilyloxysilyl)oxy-phenylsilyl]oxy-phenylsilyl]oxysilane Chemical compound C=1C=CC=CC=1[Si](C)(O[Si](C)(C)C)O[Si](C)(C=1C=CC=CC=1)O[Si](C)(O[Si](C)(C)C)C1=CC=CC=C1 FNZBSNUICNVAAM-UHFFFAOYSA-N 0.000 description 1
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 238000000870 ultraviolet spectroscopy Methods 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/74—Esters of carboxylic acids having an esterified carboxyl group bound to a carbon atom of a ring other than a six-membered aromatic ring
- C07C69/753—Esters of carboxylic acids having an esterified carboxyl group bound to a carbon atom of a ring other than a six-membered aromatic ring of polycyclic acids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
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Abstract
Description
1. 下記化学式(1−1)で表される繰り返し単位を少なくとも1種含み、
化学式(1−1)で表される繰り返し単位の合計含有量が、全繰り返し単位に対して、50モル%以上であることを特徴とするポリイミド前駆体。
3. 前記化学式(1−2)で表される繰り返し単位の合計含有量が、全繰り返し単位に対して、50モル%以上であることを特徴とする前記項2に記載のポリイミド前駆体。
化学式(2−1)で表される繰り返し単位の合計含有量が、全繰り返し単位に対して、50モル%以上であることを特徴とするポリイミド。
6. 前記化学式(2−2)で表される繰り返し単位の合計含有量が、全繰り返し単位に対して、50モル%以上であることを特徴とする前記項5に記載のポリイミド。
8. 前記項1〜3のいずれかに記載のポリイミド前駆体から得られるポリイミド、または前記項4〜6のいずれかに記載のポリイミドから主としてなるフィルム。
9. 前記項1〜3のいずれかに記載のポリイミド前駆体、または前記項4〜6のいずれかに記載のポリイミドを含むワニス。
10. 前記項1〜3のいずれかに記載のポリイミド前駆体、または前記項4〜6のいずれかに記載のポリイミドを含むワニスを用いて得られたポリイミドフィルム。
11. 前記項1〜3のいずれかに記載のポリイミド前駆体から得られるポリイミド、または前記項4〜6のいずれかに記載のポリイミドを含むことを特徴とするディスプレイ用、タッチパネル用、または太陽電池用の基板。
14. 下記化学式(M−3)で表されるテトラエステル化合物。
と脂肪族スルホン酸クロリドまたは芳香族スルホン酸クロリドとを反応させて、下記化学式(M−A−2)で表されるオレフィン化合物
を得る工程、
(B)前記化学式(M−A−2)で表されるオレフィン化合物を、パラジウム触媒と銅化合物存在下、アルコール化合物と一酸化炭素と反応させて、下記化学式(M−A−3)で表されるテトラエステル化合物
を得る工程、
(C)前記化学式(M−A−3)で表されるテトラエステル化合物より、下記化学式(M−3)で表されるテトラエステル化合物
を得る工程、
(D)前記化学式(M−3)で表されるテトラエステル化合物の酸化反応により、下記化学式(M−2)で表されるテトラエステル化合物
を得る工程、
(E)前記化学式(M−2)で表されるテトラエステル化合物を酸触媒の存在下、有機溶媒中で反応させて、下記化学式(M−1)で表されるテトラカルボン酸二無水物
18. 下記化学式(M−6)で表されるジハロゲノジカルボン酸無水物。
を得る工程、
(C)前記化学式(M−6)で表されるジハロゲノジカルボン酸無水物を無水マレイン酸と反応させて、下記化学式(M−4−1)で表されるテトラカルボン酸二無水物
を得る工程、
(E)前記化学式(M−5−1)で表されるテトラエステル化合物を金属触媒存在下、水素と反応させて、下記化学式(M−5−2)で表されるテトラエステル化合物
を得る工程、
(F)前記化学式(M−5−2)で表されるテトラエステル化合物を酸触媒の存在下、有機溶媒中で反応させて、下記化学式(M−4−2)で表されるテトラカルボン酸二無水物
を得る工程、
(C)前記化学式(M−C−4)で表されるジエステル化合物を、パラジウム触媒及び銅化合物存在下、アルコール化合物と一酸化炭素と反応させて、下記化学式(M−C−5)で表されるテトラエステル化合物
を得る工程、
(D)前記化学式(M−C−5)で表されるテトラエステル化合物を酸触媒の存在下、有機溶媒中で反応させて、下記化学式(M−9)で表されるテトラカルボン酸二無水物
本発明のポリイミド前駆体は、溶媒中でテトラカルボン酸成分としてのテトラカルボン酸二無水物とジアミン成分とを略等モル、好ましくはテトラカルボン酸成分に対するジアミン成分のモル比[ジアミン成分のモル数/テトラカルボン酸成分のモル数]が好ましくは0.90〜1.10、より好ましくは0.95〜1.05の割合で、例えば120℃以下の比較的低温度でイミド化を抑制しながら反応することによって、ポリイミド前駆体溶液組成物として好適に得ることができる。
テトラカルボン酸二無水物を任意のアルコールと反応させ、ジエステルジカルボン酸を得た後、塩素化試薬(チオニルクロライド、オキサリルクロライドなど)と反応させ、ジエステルジカルボン酸クロライドを得る。このジエステルジカルボン酸クロライドとジアミンを−20〜120℃、好ましくは−5〜80℃の範囲で1〜72時間攪拌することで、ポリイミド前駆体が得られる。80℃以上で反応させる場合、分子量が重合時の温度履歴に依存して変動し、また熱によりイミド化が進行することから、ポリイミド前駆体を安定して製造できなくなる可能性がある。また、ジエステルジカルボン酸とジアミンを、リン系縮合剤や、カルボジイミド縮合剤などを用いて脱水縮合することでも、簡便にポリイミド前駆体が得られる。
あらかじめ、ジアミンとシリル化剤を反応させ、シリル化されたジアミンを得る。必要に応じて、蒸留等により、シリル化されたジアミンの精製を行う。そして、脱水された溶剤中にシリル化されたジアミンを溶解させておき、攪拌しながら、テトラカルボン酸二無水物を徐々に添加し、0〜120℃、好ましくは5〜80℃の範囲で1〜72時間攪拌することで、ポリイミド前駆体が得られる。80℃以上で反応させる場合、分子量が重合時の温度履歴に依存して変動し、また熱によりイミド化が進行することから、ポリイミド前駆体を安定して製造できなくなる可能性がある。
1)の方法で得られたポリアミド酸溶液とシリル化剤を混合し、0〜120℃、好ましくは5〜80℃の範囲で1〜72時間攪拌することで、ポリイミド前駆体が得られる。80℃以上で反応させる場合、分子量が重合時の温度履歴に依存して変動し、また熱によりイミド化が進行することから、ポリイミド前駆体を安定して製造できなくなる可能性がある。
第1工程では、R5’、R6’が−CH2−である化学式(M−1)のテトラカルボン酸二無水物(DMADA)を合成する場合、p−ベンゾキノン(BQ)とシクロペンタジエン(CP)とを反応させて、1,4,4a,5,8,8a,9a,10a−オクタヒドロ−1,4:5,8−ジメタノアントラセン−9,10−ジオン(DNBQ)を合成する。R5’、R6’が−CH2CH2−である化学式(M−1)のテトラカルボン酸二無水物を合成する場合、ここで、シクロペンタジエン(CP)に代えて、1,3−シクロヘキサジエンをBQと反応させればよい。
第2工程では、第1工程で得られたDNBQと水素化ホウ素ナトリウムとを反応させて、1,4,4a,5,8,8a,9,9a,10,10a−デカヒドロ−1,4:5,8−ジメタノアントラセン−9,10−ジオール(DNHQ)を合成する。
第3工程では、塩基存在下で、第2工程で得られたDNHQとメタンスルホン酸クロリドとを反応させて、1,4,4a,5,8,8a,9,9a,10,10a−デカヒドロ−1,4:5,8−ジメタノアントラセン−9,10−ジイル ジメタンスルホネート(DNCMS;この場合、Rは−CH3〔−SO2Rはメシル基(−SO2CH3)〕)を合成する。メタンスルホン酸クロリドに代えて、その他の脂肪族スルホン酸クロリドまたは芳香族スルホン酸クロリドを使用することもできる。
第4工程では、パラジウム触媒と銅化合物存在下、メタノール類と一酸化炭素を、第3工程で得られたDNCMSとを反応させて、テトラメチル−9,10−ビス((メチルスルホニル)オキシ)テトラデカヒドロ−1,4:5,8−ジメタノアントラセン−2,3,6,7−テトラカルボキシレート(DNMTE;この場合、R11〜R14はメチル基)を合成する。メタノールに代えて、所望のエステル化合物に対応するその他のアルコール化合物を使用することもできる。
第5工程では、第4工程で得られたDNMTEの脱メタンスルホニル化反応により、テトラメチル−1,2,3,4,4a,5,6,7,8,9a−デカヒドロ−1,4:5,8−ジメタノアントラセン−2,3,6,7−テトラカルボキシレート(DMHAE)を合成する。この第5工程で得られる化合物は、前記化学式(M−3)で表されるテトラエステル化合物であり、新規な化合物である。
第6工程では、第5工程で得られたDMHAEの芳香族化反応(酸化反応)により、テトラメチル−1,2,3,4,5,6,7,8−オクタヒドロ−1,4:5,8−ジメタノアントラセン−2,3,6,7−テトラカルボキシレート(DMAME)を合成する。この第6工程で得られる化合物は、前記化学式(M−2)で表されるテトラエステル化合物であり、新規な化合物である。
第7工程では、第6工程で得られたDMAMEの無水化反応により、3a,4,6,6a,9a,10,12,12a−オクタヒドロ−1H,3H−4,12:6,10−ジメタノアントラ[2,3−c:6,7−c’]ジフラン−1,3,7,9−テトラオン(DMADA)を合成する。この第7工程で得られる化合物が、前記化学式(M−1)で表されるテトラカルボン酸二無水物である。
第1工程では、5−ノルボルネン−2,3−ジカルボン酸無水物(NA)と1,3−ブタジエンとを反応させて、3a,4,4a,5,8,8a,9,9a−オクタヒドロ−4,9−メタノナフト[2,3−c]フラン−1,3−ジオン(OMNA)を合成する。この第1工程で得られる化合物は、前記化学式(M−7)で表されるジカルボン酸無水物であり、新規な化合物である。
第2工程では、第1工程で得られたOMNAと、ジハロゲン化剤としての臭素とを反応させて、6,7−ジブロモデカヒドロ−4,9−メタノナフト[2,3−c]フラン−1,3−ジオン(DBDNA;この場合、X11、X12は−Br)を合成する。臭素に代えて、後述する、その他のジハロゲン化剤を使用することもできる。この第2工程で得られる化合物は、前記化学式(M−6)で表されるジハロゲノジカルボン酸無水物であり、新規な化合物である。
第3工程では、第2工程で得られたDBDNAと無水マレイン酸とを反応させて、3a,4,4a,5,5a,8a,9,9a,10,10a−デカヒドロ−1H,3H−4,10−エタノ−5,9−メタノナフト[2,3−c:6,7−c’]ジフラン−1,3,6,8−テトラオン(EEMDA)を合成する。この第3工程で得られる化合物は、R7が−CH=CH−である前記化学式(M−4)で表されるテトラカルボン酸二無水物であり、新規な化合物である。
第4工程では、第3工程で得られたEEMDAとメタノール類とを反応させて、テトラメチル−1,4,4a,5,6,7,8,8a−オクタヒドロ−1,4−エタノ−5,8−メタノナフタレン−6,7,10,11−テトラカルボキシレート(EEMDE;この場合、R21〜R24はメチル基)を合成する。メタノールに代えて、所望のエステル化合物に対応するその他のアルコール化合物を使用することもできる。この第4工程で得られる化合物は、R7が−CH=CH−である前記化学式(M−5)で表されるテトラエステル化合物であり、新規な化合物である。
第5工程では、第4工程で得られたEEMDEを水素と反応させて、テトラメチル−デカヒドロ−1,4−エタノ−5,8−メタノナフタレン−2,3,6,7−テトラカルボキシレート(EMDE)を合成する。この第5工程で得られる化合物は、R7が−CH2CH2−である前記化学式(M−5)で表されるテトラエステル化合物であり、新規な化合物である。
第6工程では、第5工程で得られたEMDEの無水化反応により、デカヒドロ−1H,3H−4,10−エタノ−5,9−メタノナフト[2,3−c:6,7−c’]ジフラン−1,3,6,8−テトラオン(EMDA)を合成する。この第6工程で得られる化合物が、R7が−CH2CH2−である前記化学式(M−4)で表されるテトラカルボン酸二無水物である。
第1工程では、R4が−CH2−である化学式(M−9)のテトラカルボン酸二無水物(BNDA)を合成する場合、シス−1,4−ジクロロ−2−ブテン(DCB)とシクロペンタジエン(CP)とを反応させて、5,6−ビス(クロロメチル)ビシクロ[2.2.1]ヘプト−2−エン(BCMN)を合成する。R4が−CH2CH2−である化学式(M−9)のテトラカルボン酸二無水物を合成する場合、ここで、シクロペンタジエン(CP)に代えて、1,3−シクロヘキサジエンをDCBと反応させればよい。
第2工程では、第1工程で得られたBCMNと塩基との反応により脱塩化水素化させて、5,6−ジメチレンビシクロ[2.2.1]ヘプト−2−エン(CYDE)を合成する。
第3工程では、第2工程で得られたCYDEとアセチレンジカルボン酸ジメチル(DMAD)とを反応させて、ジメチル1,4,5,8−テトラヒドロ−1,4−メタノナフタレン−6,7−ジカルボキシレート(CYME;この場合、R31、R32はメチル基)を合成する。アセチレンジカルボン酸ジメチルに代えて、後述する、その他のアセチレンジカルボン酸ジエステルを使用することもできる。
第4工程では、第3工程で得られたCYMEの芳香族化反応(酸化反応)により、ジメチル1,4−ジヒドロ−1,4−メタノナフタレン−6,7−ジカルボキシレート(CYPDM)を合成する。
第5工程では、パラジウム触媒及び銅化合物存在下、第4工程で得られたCYPDMとメタノール類と一酸化炭素とを反応させて、テトラメチル−1,2,3,4−テトラヒドロ−1,4−メタノナフタレン−2,3,6,7−テトラカルボキシレート(BNME;この場合、R31〜R34はメチル基)を合成する。メタノールに代えて、所望のエステル化合物に対応するその他のアルコール化合物を使用することもできる。
第6工程では、第5工程で得られたBNMEの無水化反応により、3a,4,10,10a−テトラヒドロ−1H,3H−4,10−メタノナフト[2,3−c:6,7−c’]ジフラン−1,3,6,8−テトラオン(BNDA)を合成する。この第6工程で得られる化合物が、前記化学式(M−9)で表されるテトラカルボン酸二無水物である。
[全光透過率]
紫外可視分光光度計/V−650DS(日本分光製)を用いて、膜厚10μmのポリイミドフィルムの全光透過率(380nm〜780nmにおける平均透過率)を測定した。
ポリイミドフィルムをIEC−540(S)規格のダンベル形状に打ち抜いて試験片(幅:4mm)とし、ORIENTEC社製TENSILONを用いて、チャック間長30mm、引張速度2mm/分で、初期の引張弾性率、破断点伸度、破断強度を測定した。
膜厚10μmのポリイミドフィルムを幅4mmの短冊状に切り取って試験片とし、TMA/SS6100(エスアイアイ・ナノテクノロジー株式会社製)を用い、チャック間長15mm、荷重2g、昇温速度20℃/分で500℃まで昇温した。得られたTMA曲線から、100℃から250℃までの線熱膨張係数を求めた。また、TMA曲線の変曲点をTg(ガラス転移温度)とした。
膜厚10μmのポリイミドフィルムを試験片とし、TAインスツルメント社製 熱重量測定装置(Q5000IR)を用い、窒素気流中、昇温速度10℃/分で25℃から600℃まで昇温した。得られた重量曲線から、5%重量減少温度を求めた。
DABAN: 4,4’−ジアミノベンズアニリド
PPD: p−フェニレンジアミン
TFMB: 2,2’−ビス(トリフルオロメチル)ベンジジン
4,4’−ODA: 4,4’−オキシジアニリン
TPE−R: 1,3−ビス(4−アミノフェノキシ)ベンゼン
BAPB: 4,4’−ビス(4−アミノフェノキシ)ビフェニル
tra−DACH:トランス−1,4−ジアミノシクロヘキサン
[テトラカルボン酸成分]
TNDA:テトラデカヒドロ−1H,3H−4,12:5,11:6,10−トリメタノアントラ[2,3−c:6,7−c’]ジフラン−1,3,7,9−テトラオン
BNDA:3a,4,10,10a−テトラヒドロ−1H,3H−4,10−メタノナフト[2,3−c:6,7−c’]ジフラン−1,3,6,8−テトラオン
DMADA:3a,4,6,6a,9a,10,12,12a−オクタヒドロ−1H,3H−4,12:6,10−ジメタノアントラ[2,3−c:6,7−c’]ジフラン−1,3,7,9−テトラオン
EMDAdx:(3aR,4R,5S,5aR,8aS,9R,10S,10aS)−デカヒドロ−1H,3H−4,10−エタノ−5,9−メタノナフト[2,3−c:6,7−c’]ジフラン−1,3,6,8−テトラオン
EMDAxx:(3aR,4R,5S,5aS,8aR,9R,10S,10aS)−デカヒドロ−1H,3H−4,10−エタノ−5,9−メタノナフト[2,3−c:6,7−c’]ジフラン−1,3,6,8−テトラオン
NMP: N−メチル−2−ピロリドン
DMAc: N,N−ジメチルアセトアミド
CI−MS(m/z); 241(M+1)
CI−MS(m/z); 245(M+1)
CI−MS(m/z); 401(M+1)
CI−MS(m/z); 637(M+1)
CI−MS(m/z); 445(M+1)
CI−MS(m/z); 442(M+1)
CI−MS(m/z); 351(M+1)
CI−MS(m/z); 219(M+1)
CI−MS(m/z); 379(M+1)
CI−MS(m/z); 314(M+1)
CI−MS(m/z); 407(M+1)
1H−NMR(CDCl3,σ(ppm)); 1.25(d,J=11Hz,1H),1.49(d,J=9.0Hz,2H),1.79(d,J=9.0Hz,2H),2.00(s,2H),2.14(s,2H),2.24(d,J=11Hz,1H),2.51(s,2H),2.90(s,2H),3.02(t,J=2.0Hz,2H),3.63(s,6H),3.64(s,6H)
CI−MS(m/z); 409(M+1)
CI−MS(m/z); 317(M+1)
CI−MS(m/z); 219(M+1)
CI−MS(m/z); 379(M+1)
CI−MS(m/z); 314(M+1)
CI−MS(m/z); 407(M+1)
CI−MS(m/z); 409(M+1)
CI−MS(m/z); 317(M+1)
CI−MS(m/z); 191(M+1)
CI−MS(m/z); 119(M+1)
CI−MS(m/z); 261(M+1)
CI−MS(m/z); 259(M+1)
CI−MS(m/z); 377(M+1)
CI−MS(m/z); 285(M+1)
窒素ガスで置換した反応容器中にDABAN 0.60g(2.6ミリモル)を入れ、NMPを、仕込みモノマー総質量(ジアミン成分とカルボン酸成分の総和)が 20質量%となる量の6.29gを加え、室温で1時間攪拌した。この溶液にTNDA 1.12g(2.6ミリモル)を徐々に加えた。室温で48時間撹拌し、均一で粘稠なポリイミド前駆体溶液を得た。
窒素ガスで置換した反応容器中にDABAN 1.00g(4.4ミリモル)とPPD 0.07g(0.6ミリモル)とBAPB 0.46g(1.3ミリモル)を入れ、NMPを、仕込みモノマー総質量(ジアミン成分とカルボン酸成分の総和)が 25質量%となる量の11.54gを加え、室温で1時間攪拌した。この溶液にTNDA 2.32g(6.3ミリモル)を徐々に加えた。室温で48時間撹拌し、均一で粘稠なポリイミド前駆体溶液を得た。
窒素ガスで置換した反応容器中にBAPB 1.00g(2.7ミリモル)を入れ、NMPを、仕込みモノマー総質量(ジアミン成分とカルボン酸成分の総和)が 25質量%となる量の6.00gを加え、室温で1時間攪拌した。この溶液にTNDA 1.00g(2.7ミリモル)を徐々に加えた。室温で48時間撹拌し、均一で粘稠なポリイミド前駆体溶液を得た。
窒素ガスで置換した反応容器中に4,4’−ODA 0.70g(3.5ミリモル)を入れ、DMAcを、仕込みモノマー総質量(ジアミン成分とカルボン酸成分の総和)が 20質量%となる量の7.95gを加え、室温で1時間攪拌した。この溶液にTNDA 1.29g(3.5ミリモル)を徐々に加えた。室温で48時間撹拌し、均一で粘稠なポリイミド前駆体溶液を得た。
窒素ガスで置換した反応容器中にDABAN 0.23g(1.0ミリモル)を入れ、NMPを、仕込みモノマー総質量(ジアミン成分とカルボン酸成分の総和)が 16質量%となる量の2.70gを加え、室温で1時間攪拌した。この溶液に実施例S−3で得られたBNDA 0.29g(1.0ミリモル)を徐々に加えた。室温で48時間撹拌し、均一で粘稠なポリイミド前駆体溶液を得た。
窒素ガスで置換した反応容器中にPPD 0.40g(3.7ミリモル)を入れ、NMPを、仕込みモノマー総質量(ジアミン成分とカルボン酸成分の総和)が 20質量%となる量の5.81gを加え、室温で1時間攪拌した。この溶液に実施例S−3で得られたBNDA 1.05g(3.7ミリモル)を徐々に加えた。室温で48時間撹拌し、均一で粘稠なポリイミド前駆体溶液を得た。
窒素ガスで置換した反応容器中にTFMB 1.52g(4.7ミリモル)を入れ、NMPを、仕込みモノマー総質量(ジアミン成分とカルボン酸成分の総和)が 20質量%となる量の11.41gを加え、室温で1時間攪拌した。この溶液に実施例S−3で得られたBNDA 1.35g(4.7ミリモル)を徐々に加えた。室温で48時間撹拌し、均一で粘稠なポリイミド前駆体溶液を得た。
窒素ガスで置換した反応容器中にDABAN 0.40g(1.8ミリモル)とTFMB 0.70g(2.2ミリモル)とBAPB 0.16g(0.4ミリモル)を入れ、NMPを、仕込みモノマー総質量(ジアミン成分とカルボン酸成分の総和)が 20質量%となる量の10.00gを加え、室温で1時間攪拌した。この溶液に実施例S−3で得られたBNDA 1.24g(4.4ミリモル)を徐々に加えた。室温で48時間撹拌し、均一で粘稠なポリイミド前駆体溶液を得た。
窒素ガスで置換した反応容器中にtra−DACH 0.39g(3.5ミリモル)を入れ、NMPを、仕込みモノマー総質量(ジアミン成分とカルボン酸成分の総和)が 11質量%となる量の11.14gを加え、室温で1時間攪拌した。この溶液に実施例S−3で得られたBNDA 0.98g(3.5ミリモル)を徐々に加えた。室温で48時間撹拌し、均一で粘稠なポリイミド前駆体溶液を得た。
窒素ガスで置換した反応容器中に4,4’−ODA 0.60g(3.0ミリモル)を入れ、NMPを、仕込みモノマー総質量(ジアミン成分とカルボン酸成分の総和)が 10質量%となる量の13.06gを加え、室温で1時間攪拌した。この溶液に実施例S−3で得られたBNDA 0.85g(3.0ミリモル)を徐々に加えた。室温で48時間撹拌し、均一で粘稠なポリイミド前駆体溶液を得た。
窒素ガスで置換した反応容器中に4,4’−ODA 0.70g(3.5ミリモル)を入れ、NMPを、仕込みモノマー総質量(ジアミン成分とカルボン酸成分の総和)が 7質量%となる量の25.57gを加え、室温で1時間攪拌した。この溶液に実施例S−1で得られたDMADA 1.22g(3.5ミリモル)を徐々に加えた。室温で48時間撹拌し、均一で粘稠なポリイミド前駆体溶液を得た。
窒素ガスで置換した反応容器中にTPE−R 1.20g(4.1ミリモル)を入れ、NMPを、仕込みモノマー総質量(ジアミン成分とカルボン酸成分の総和)が 25質量%となる量の11.39gを加え、室温で1時間攪拌した。この溶液に実施例S−2−2で得られたEMDAxx 1.32g(4.1ミリモル)を徐々に加えた。室温で48時間撹拌し、均一で粘稠なポリイミド前駆体溶液を得た。
Claims (21)
- 下記化学式(1−1)で表される繰り返し単位を少なくとも1種含み、
化学式(1−1)で表される繰り返し単位の合計含有量が、全繰り返し単位に対して、50モル%以上であることを特徴とするポリイミド前駆体。
- 前記化学式(1−2)で表される繰り返し単位の合計含有量が、全繰り返し単位に対して、50モル%以上であることを特徴とする請求項2に記載のポリイミド前駆体。
- 下記化学式(2−1)で表される繰り返し単位を少なくとも1種含み、
化学式(2−1)で表される繰り返し単位の合計含有量が、全繰り返し単位に対して、50モル%以上であることを特徴とするポリイミド。
- 前記化学式(2−2)で表される繰り返し単位の合計含有量が、全繰り返し単位に対して、50モル%以上であることを特徴とする請求項5に記載のポリイミド。
- 請求項1〜3のいずれかに記載のポリイミド前駆体から得られるポリイミド。
- 請求項1〜3のいずれかに記載のポリイミド前駆体から得られるポリイミド、または請求項4〜6のいずれかに記載のポリイミドから主としてなるフィルム。
- 請求項1〜3のいずれかに記載のポリイミド前駆体、または請求項4〜6のいずれかに記載のポリイミドを含むワニス。
- 請求項1〜3のいずれかに記載のポリイミド前駆体、または請求項4〜6のいずれかに記載のポリイミドを含むワニスを用いて得られたポリイミドフィルム。
- 請求項1〜3のいずれかに記載のポリイミド前駆体から得られるポリイミド、または請求項4〜6のいずれかに記載のポリイミドを含むことを特徴とするディスプレイ用、タッチパネル用、または太陽電池用の基板。
- (A)塩基存在下、下記化学式(M−A−1)で表されるオレフィン化合物
と脂肪族スルホン酸クロリドまたは芳香族スルホン酸クロリドとを反応させて、下記化学式(M−A−2)で表されるオレフィン化合物
を得る工程、
(B)前記化学式(M−A−2)で表されるオレフィン化合物を、パラジウム触媒と銅化合物存在下、アルコール化合物と一酸化炭素と反応させて、下記化学式(M−A−3)で表されるテトラエステル化合物
を得る工程、
(C)前記化学式(M−A−3)で表されるテトラエステル化合物より、下記化学式(M−3)で表されるテトラエステル化合物
を得る工程、
(D)前記化学式(M−3)で表されるテトラエステル化合物の酸化反応により、下記化学式(M−2)で表されるテトラエステル化合物
を得る工程、
(E)前記化学式(M−2)で表されるテトラエステル化合物を酸触媒の存在下、有機溶媒中で反応させて、下記化学式(M−1)で表されるテトラカルボン酸二無水物
を得る工程、
を含むことを特徴とするテトラカルボン酸二無水物の製造方法。 - (A)下記化学式(M−B)で表されるジカルボン酸無水物
(B)前記化学式(M−7)で表されるジカルボン酸無水物とジハロゲン化剤とを反応させて、下記化学式(M−6)で表されるジハロゲノジカルボン酸無水物
を得る工程、
(C)前記化学式(M−6)で表されるジハロゲノジカルボン酸無水物を無水マレイン酸と反応させて、下記化学式(M−4−1)で表されるテトラカルボン酸二無水物
(D)前記化学式(M−4−1)で表されるテトラカルボン酸二無水物を、酸の存在下、アルコール化合物と反応させて、下記化学式(M−5−1)で表されるテトラエステル化合物
を得る工程、
(E)前記化学式(M−5−1)で表されるテトラエステル化合物を金属触媒存在下、水素と反応させて、下記化学式(M−5−2)で表されるテトラエステル化合物
を得る工程、
(F)前記化学式(M−5−2)で表されるテトラエステル化合物を酸触媒の存在下、有機溶媒中で反応させて、下記化学式(M−4−2)で表されるテトラカルボン酸二無水物
を含むことを特徴とするテトラカルボン酸二無水物の製造方法。 - (A)下記化学式(M−C−1)で表されるジエン化合物
と下記化学式(M−C−2)で表されるアセチレン化合物
とを反応させて、下記化学式(M−C−3)で表されるジエステル化合物
を得る工程、
(B)前記化学式(M−C−3)で表されるジエステル化合物の酸化反応により、下記化学式(M−C−4)で表されるジエステル化合物
を得る工程、
(C)前記化学式(M−C−4)で表されるジエステル化合物を、パラジウム触媒及び銅化合物存在下、アルコール化合物と一酸化炭素と反応させて、下記化学式(M−C−5)で表されるテトラエステル化合物
を得る工程、
(D)前記化学式(M−C−5)で表されるテトラエステル化合物を酸触媒の存在下、有機溶媒中で反応させて、下記化学式(M−9)で表されるテトラカルボン酸二無水物
を得る工程、
を含むことを特徴とするテトラカルボン酸二無水物の製造方法。
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