JPS6224034B2 - - Google Patents

Info

Publication number: JPS6224034B2
Authority: JP; Japan
Prior art keywords: formula; polymer; isothianaphthene; carbon atoms; conductive
Prior art date: 1984-06-15
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Expired

Application number

JP59121956A

Other languages

English (en)

Japanese (ja)

Other versions

JPS6112784A (ja

Inventor

Masao Kobayashi

Udoru Furetsudo

Jee Hiigaa Aran

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

RIIJENTSU OBU ZA UNIV OBU KARIFUORUNIA ZA

Original Assignee

RIIJENTSU OBU ZA UNIV OBU KARIFUORUNIA ZA

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1984-06-15

Filing date

1984-06-15

Publication date

1987-05-26

1984-06-15 Application filed by RIIJENTSU OBU ZA UNIV OBU KARIFUORUNIA ZA filed Critical RIIJENTSU OBU ZA UNIV OBU KARIFUORUNIA ZA

1984-06-15 Priority to JP59121956A priority Critical patent/JPS6112784A/ja

1985-05-22 Priority to US06/736,984 priority patent/US4640748A/en

1985-05-30 Priority to CA000482753A priority patent/CA1248690A/fr

1985-05-31 Priority to EP85303864A priority patent/EP0164974B1/fr

1985-05-31 Priority to AT85303864T priority patent/ATE53046T1/de

1985-05-31 Priority to DE8585303864T priority patent/DE3577860D1/de

1986-01-21 Publication of JPS6112784A publication Critical patent/JPS6112784A/ja

1987-05-26 Publication of JPS6224034B2 publication Critical patent/JPS6224034B2/ja

Status Granted legal-status Critical Current

Links

125000004432 carbon atom Chemical group C* 0.000 claims description 16
150000001450 anions Chemical class 0.000 claims description 12
LYTMVABTDYMBQK-UHFFFAOYSA-N 2-benzothiophene Chemical group C1=CC=CC2=CSC=C21 LYTMVABTDYMBQK-UHFFFAOYSA-N 0.000 claims description 10
239000011244 liquid electrolyte Substances 0.000 claims description 8
239000000758 substrate Substances 0.000 claims description 8
229910052739 hydrogen Inorganic materials 0.000 claims description 7
239000010409 thin film Substances 0.000 claims description 7
229920001940 conductive polymer Polymers 0.000 claims description 5
238000006116 polymerization reaction Methods 0.000 claims description 5
150000002430 hydrocarbons Chemical class 0.000 claims description 4
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
239000001257 hydrogen Substances 0.000 claims description 3
239000004215 Carbon black (E152) Substances 0.000 claims description 2
229930195733 hydrocarbon Natural products 0.000 claims description 2
229920000642 polymer Polymers 0.000 description 23
-1 isothianaphthene compound Chemical class 0.000 description 18
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 16
239000003115 supporting electrolyte Substances 0.000 description 13
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 12
239000000463 material Substances 0.000 description 11
238000010521 absorption reaction Methods 0.000 description 10
239000000243 solution Substances 0.000 description 10
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
238000000862 absorption spectrum Methods 0.000 description 9
238000000034 method Methods 0.000 description 9
125000003118 aryl group Chemical group 0.000 description 8
239000010408 film Substances 0.000 description 8
125000000217 alkyl group Chemical group 0.000 description 7
239000003960 organic solvent Substances 0.000 description 7
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
239000013078 crystal Substances 0.000 description 6
239000003792 electrolyte Substances 0.000 description 6
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 6
125000004435 hydrogen atom Chemical group [H]* 0.000 description 5
229910052757 nitrogen Inorganic materials 0.000 description 5
230000004044 response Effects 0.000 description 5
239000002904 solvent Substances 0.000 description 5
229910052717 sulfur Inorganic materials 0.000 description 5
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 4
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 4
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 4
MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 4
150000001875 compounds Chemical class 0.000 description 4
238000010586 diagram Methods 0.000 description 4
239000011521 glass Substances 0.000 description 4
238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 4
BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 4
239000002244 precipitate Substances 0.000 description 4
239000000047 product Substances 0.000 description 4
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
229910013684 LiClO 4 Inorganic materials 0.000 description 3
239000007864 aqueous solution Substances 0.000 description 3
JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 description 3
150000004649 carbonic acid derivatives Chemical class 0.000 description 3
150000001768 cations Chemical class 0.000 description 3
AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 3
150000002825 nitriles Chemical class 0.000 description 3
125000004433 nitrogen atom Chemical group N* 0.000 description 3
125000004430 oxygen atom Chemical group O* 0.000 description 3
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
230000000379 polymerizing effect Effects 0.000 description 3
150000003839 salts Chemical class 0.000 description 3
239000011734 sodium Substances 0.000 description 3
UGNWTBMOAKPKBL-UHFFFAOYSA-N tetrachloro-1,4-benzoquinone Chemical compound ClC1=C(Cl)C(=O)C(Cl)=C(Cl)C1=O UGNWTBMOAKPKBL-UHFFFAOYSA-N 0.000 description 3
238000005160 1H NMR spectroscopy Methods 0.000 description 2
YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 description 2
OZJPLYNZGCXSJM-UHFFFAOYSA-N 5-valerolactone Chemical compound O=C1CCCCO1 OZJPLYNZGCXSJM-UHFFFAOYSA-N 0.000 description 2
229910017008 AsF 6 Inorganic materials 0.000 description 2
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 2
XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 2
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
JRNVZBWKYDBUCA-UHFFFAOYSA-N N-chlorosuccinimide Chemical compound ClN1C(=O)CCC1=O JRNVZBWKYDBUCA-UHFFFAOYSA-N 0.000 description 2
PHXQIAWFIIMOKG-UHFFFAOYSA-N NClO Chemical compound NClO PHXQIAWFIIMOKG-UHFFFAOYSA-N 0.000 description 2
PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 2
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 2
230000015572 biosynthetic process Effects 0.000 description 2
229940075397 calomel Drugs 0.000 description 2
229910052799 carbon Inorganic materials 0.000 description 2
238000006243 chemical reaction Methods 0.000 description 2
150000008280 chlorinated hydrocarbons Chemical class 0.000 description 2
238000004040 coloring Methods 0.000 description 2
125000004122 cyclic group Chemical group 0.000 description 2
230000006866 deterioration Effects 0.000 description 2
ZOMNIUBKTOKEHS-UHFFFAOYSA-L dimercury dichloride Chemical compound Cl[Hg][Hg]Cl ZOMNIUBKTOKEHS-UHFFFAOYSA-L 0.000 description 2
238000000921 elemental analysis Methods 0.000 description 2
150000002170 ethers Chemical class 0.000 description 2
IIEWJVIFRVWJOD-UHFFFAOYSA-N ethyl cyclohexane Natural products CCC1CCCCC1 IIEWJVIFRVWJOD-UHFFFAOYSA-N 0.000 description 2
150000002576 ketones Chemical class 0.000 description 2
239000004973 liquid crystal related substance Substances 0.000 description 2
238000004519 manufacturing process Methods 0.000 description 2
238000002844 melting Methods 0.000 description 2
230000008018 melting Effects 0.000 description 2
239000012528 membrane Substances 0.000 description 2
TZIHFWKZFHZASV-UHFFFAOYSA-N methyl formate Chemical compound COC=O TZIHFWKZFHZASV-UHFFFAOYSA-N 0.000 description 2
239000000203 mixture Substances 0.000 description 2
239000000178 monomer Substances 0.000 description 2
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
230000007935 neutral effect Effects 0.000 description 2
230000003287 optical effect Effects 0.000 description 2
OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical class OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 description 2
IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical class N1C(N=C2C3=CC=CC=C3C(N=C3C4=CC=CC=C4C(=N4)N3)=N2)=C(C=CC=C2)C2=C1N=C1C2=CC=CC=C2C4=N1 IEQIEDJGQAUEQZ-UHFFFAOYSA-N 0.000 description 2
229910052697 platinum Inorganic materials 0.000 description 2
RUOJZAUFBMNUDX-UHFFFAOYSA-N propylene carbonate Chemical compound CC1COC(=O)O1 RUOJZAUFBMNUDX-UHFFFAOYSA-N 0.000 description 2
JUJWROOIHBZHMG-UHFFFAOYSA-O pyridinium Chemical compound C1=CC=[NH+]C=C1 JUJWROOIHBZHMG-UHFFFAOYSA-O 0.000 description 2
WVIICGIFSIBFOG-UHFFFAOYSA-N pyrylium Chemical compound C1=CC=[O+]C=C1 WVIICGIFSIBFOG-UHFFFAOYSA-N 0.000 description 2
239000007787 solid Substances 0.000 description 2
150000003462 sulfoxides Chemical class 0.000 description 2
238000003786 synthesis reaction Methods 0.000 description 2
WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
KGKAYWMGPDWLQZ-UHFFFAOYSA-N 1,2-bis(bromomethyl)benzene Chemical compound BrCC1=CC=CC=C1CBr KGKAYWMGPDWLQZ-UHFFFAOYSA-N 0.000 description 1
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
JWUJQDFVADABEY-UHFFFAOYSA-N 2-methyltetrahydrofuran Chemical compound CC1CCCO1 JWUJQDFVADABEY-UHFFFAOYSA-N 0.000 description 1
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
CMJLMPKFQPJDKP-UHFFFAOYSA-N 3-methylthiolane 1,1-dioxide Chemical compound CC1CCS(=O)(=O)C1 CMJLMPKFQPJDKP-UHFFFAOYSA-N 0.000 description 1
229910016467 AlCl 4 Inorganic materials 0.000 description 1
229910020366 ClO 4 Inorganic materials 0.000 description 1
KMTRUDSVKNLOMY-UHFFFAOYSA-N Ethylene carbonate Chemical compound O=C1OCCO1 KMTRUDSVKNLOMY-UHFFFAOYSA-N 0.000 description 1
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
229910015015 LiAsF 6 Inorganic materials 0.000 description 1
229910013063 LiBF 4 Inorganic materials 0.000 description 1
229910013870 LiPF 6 Inorganic materials 0.000 description 1
229910012513 LiSbF 6 Inorganic materials 0.000 description 1
NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 1
UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 1
229910019398 NaPF6 Inorganic materials 0.000 description 1
UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 1
229910019142 PO4 Inorganic materials 0.000 description 1
RFFFKMOABOFIDF-UHFFFAOYSA-N Pentanenitrile Chemical compound CCCCC#N RFFFKMOABOFIDF-UHFFFAOYSA-N 0.000 description 1
229920003171 Poly (ethylene oxide) Polymers 0.000 description 1
239000004793 Polystyrene Substances 0.000 description 1
UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 description 1
FNYLWPVRPXGIIP-UHFFFAOYSA-N Triamterene Chemical compound NC1=NC2=NC(N)=NC(N)=C2N=C1C1=CC=CC=C1 FNYLWPVRPXGIIP-UHFFFAOYSA-N 0.000 description 1
239000002253 acid Substances 0.000 description 1
229910052783 alkali metal Inorganic materials 0.000 description 1
229910001413 alkali metal ion Inorganic materials 0.000 description 1
150000001340 alkali metals Chemical class 0.000 description 1
PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
229910000147 aluminium phosphate Inorganic materials 0.000 description 1
150000001408 amides Chemical class 0.000 description 1
150000001412 amines Chemical class 0.000 description 1
238000004458 analytical method Methods 0.000 description 1
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
238000005452 bending Methods 0.000 description 1
239000004327 boric acid Substances 0.000 description 1
150000001642 boronic acid derivatives Chemical class 0.000 description 1
KVNRLNFWIYMESJ-UHFFFAOYSA-N butyronitrile Chemical compound CCCC#N KVNRLNFWIYMESJ-UHFFFAOYSA-N 0.000 description 1
125000005626 carbonium group Chemical group 0.000 description 1
238000010538 cationic polymerization reaction Methods 0.000 description 1
239000003086 colorant Substances 0.000 description 1
238000004891 communication Methods 0.000 description 1
239000004020 conductor Substances 0.000 description 1
238000007796 conventional method Methods 0.000 description 1
238000001816 cooling Methods 0.000 description 1
238000000151 deposition Methods 0.000 description 1
239000012769 display material Substances 0.000 description 1
238000001035 drying Methods 0.000 description 1
238000010828 elution Methods 0.000 description 1
238000005265 energy consumption Methods 0.000 description 1
150000002148 esters Chemical class 0.000 description 1
ZUNGGJHBMLMRFJ-UHFFFAOYSA-O ethoxy-hydroxy-oxophosphanium Chemical compound CCO[P+](O)=O ZUNGGJHBMLMRFJ-UHFFFAOYSA-O 0.000 description 1
ZJXZSIYSNXKHEA-UHFFFAOYSA-N ethyl dihydrogen phosphate Chemical compound CCOP(O)(O)=O ZJXZSIYSNXKHEA-UHFFFAOYSA-N 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
239000011888 foil Substances 0.000 description 1
229910052736 halogen Inorganic materials 0.000 description 1
125000005843 halogen group Chemical group 0.000 description 1
229910052738 indium Inorganic materials 0.000 description 1
229910010272 inorganic material Inorganic materials 0.000 description 1
239000011147 inorganic material Substances 0.000 description 1
239000012212 insulator Substances 0.000 description 1
150000002500 ions Chemical class 0.000 description 1
239000010410 layer Substances 0.000 description 1
WABPQHHGFIMREM-UHFFFAOYSA-N lead(0) Chemical compound [Pb] WABPQHHGFIMREM-UHFFFAOYSA-N 0.000 description 1
230000031700 light absorption Effects 0.000 description 1
GLNWILHOFOBOFD-UHFFFAOYSA-N lithium sulfide Chemical compound [Li+].[Li+].[S-2] GLNWILHOFOBOFD-UHFFFAOYSA-N 0.000 description 1
229910001537 lithium tetrachloroaluminate Inorganic materials 0.000 description 1
229910001496 lithium tetrafluoroborate Inorganic materials 0.000 description 1
230000007334 memory performance Effects 0.000 description 1
229910052751 metal Inorganic materials 0.000 description 1
239000002184 metal Substances 0.000 description 1
CAAULPUQFIIOTL-UHFFFAOYSA-N methyl dihydrogen phosphate Chemical compound COP(O)(O)=O CAAULPUQFIIOTL-UHFFFAOYSA-N 0.000 description 1
125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 1
239000012046 mixed solvent Substances 0.000 description 1
239000004570 mortar (masonry) Substances 0.000 description 1
239000012452 mother liquor Substances 0.000 description 1
SKECXRFZFFAANN-UHFFFAOYSA-N n,n-dimethylmethanethioamide Chemical compound CN(C)C=S SKECXRFZFFAANN-UHFFFAOYSA-N 0.000 description 1
229910052759 nickel Inorganic materials 0.000 description 1
150000002828 nitro derivatives Chemical class 0.000 description 1
239000012299 nitrogen atmosphere Substances 0.000 description 1
239000011356 non-aqueous organic solvent Substances 0.000 description 1
QGLKJKCYBOYXKC-UHFFFAOYSA-N nonaoxidotritungsten Chemical compound O=[W]1(=O)O[W](=O)(=O)O[W](=O)(=O)O1 QGLKJKCYBOYXKC-UHFFFAOYSA-N 0.000 description 1
239000011368 organic material Substances 0.000 description 1
239000007800 oxidant agent Substances 0.000 description 1
230000001590 oxidative effect Effects 0.000 description 1
229910052760 oxygen Inorganic materials 0.000 description 1
239000001301 oxygen Substances 0.000 description 1
VLTRZXGMWDSKGL-UHFFFAOYSA-M perchlorate Inorganic materials [O-]Cl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-M 0.000 description 1
239000010452 phosphate Substances 0.000 description 1
229920000767 polyaniline Polymers 0.000 description 1
229920000728 polyester Polymers 0.000 description 1
229920006254 polymer film Polymers 0.000 description 1
239000002861 polymer material Substances 0.000 description 1
239000003505 polymerization initiator Substances 0.000 description 1
229920000128 polypyrrole Polymers 0.000 description 1
229920002223 polystyrene Polymers 0.000 description 1
229920000123 polythiophene Polymers 0.000 description 1
238000001556 precipitation Methods 0.000 description 1
FVSKHRXBFJPNKK-UHFFFAOYSA-N propionitrile Chemical compound CCC#N FVSKHRXBFJPNKK-UHFFFAOYSA-N 0.000 description 1
239000011241 protective layer Substances 0.000 description 1
239000003586 protic polar solvent Substances 0.000 description 1
238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 1
230000002441 reversible effect Effects 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
229910001545 sodium hexafluoroantimonate(V) Inorganic materials 0.000 description 1
229910001542 sodium hexafluoroarsenate(V) Inorganic materials 0.000 description 1
FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Inorganic materials [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 1
BAZAXWOYCMUHIX-UHFFFAOYSA-M sodium perchlorate Chemical compound [Na+].[O-]Cl(=O)(=O)=O BAZAXWOYCMUHIX-UHFFFAOYSA-M 0.000 description 1
229910001488 sodium perchlorate Inorganic materials 0.000 description 1
VGTPCRGMBIAPIM-UHFFFAOYSA-M sodium thiocyanate Chemical compound [Na+].[S-]C#N VGTPCRGMBIAPIM-UHFFFAOYSA-M 0.000 description 1
239000007784 solid electrolyte Substances 0.000 description 1
238000004544 sputter deposition Methods 0.000 description 1
238000003756 stirring Methods 0.000 description 1
239000000126 substance Substances 0.000 description 1
HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 1
239000011593 sulfur Substances 0.000 description 1
150000003464 sulfur compounds Chemical class 0.000 description 1
QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
239000000725 suspension Substances 0.000 description 1
229930192474 thiophene Natural products 0.000 description 1
XOLBLPGZBRYERU-UHFFFAOYSA-N tin dioxide Chemical compound O=[Sn]=O XOLBLPGZBRYERU-UHFFFAOYSA-N 0.000 description 1
229910001887 tin oxide Inorganic materials 0.000 description 1
229910000314 transition metal oxide Inorganic materials 0.000 description 1
239000012780 transparent material Substances 0.000 description 1
229960001288 triamterene Drugs 0.000 description 1
229910001930 tungsten oxide Inorganic materials 0.000 description 1
238000005406 washing Methods 0.000 description 1
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1

Landscapes

Electrochromic Elements, Electrophoresis, Or Variable Reflection Or Absorption Elements (AREA)
Polyoxymethylene Polymers And Polymers With Carbon-To-Carbon Bonds (AREA)
Devices For Indicating Variable Information By Combining Individual Elements (AREA)

JP59121956A 1984-05-31 1984-06-15 エレクトロクロミツク表示装置 Granted JPS6112784A (ja)

Priority Applications (6)

Application Number	Priority Date	Filing Date	Title
JP59121956A JPS6112784A (ja)	1984-06-15	1984-06-15	エレクトロクロミツク表示装置
US06/736,984 US4640748A (en)	1984-05-31	1985-05-22	Polyisothianaphtene, a new conducting polymer
CA000482753A CA1248690A (fr)	1984-05-31	1985-05-30	Poly-iso-thianaphthene, ou polymere conducteur nouveau genre
EP85303864A EP0164974B1 (fr)	1984-05-31	1985-05-31	Polymère ayant une structure d'isothianaphtène et dispositif d'affichage électrochromique
AT85303864T ATE53046T1 (de)	1984-05-31	1985-05-31	Polymere mit isothianaphthen-struktur und elektrochromische anzeigevorrichtung.
DE8585303864T DE3577860D1 (de)	1984-05-31	1985-05-31	Polymere mit isothianaphthen-struktur und elektrochromische anzeigevorrichtung.

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
JP59121956A JPS6112784A (ja)	1984-06-15	1984-06-15	エレクトロクロミツク表示装置

Publications (2)

Publication Number	Publication Date
JPS6112784A JPS6112784A (ja)	1986-01-21
JPS6224034B2 true JPS6224034B2 (fr)	1987-05-26

Family

ID=14824065

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
JP59121956A Granted JPS6112784A (ja)	1984-05-31	1984-06-15	エレクトロクロミツク表示装置

Country Status (1)

Country	Link
JP (1)	JPS6112784A (fr)

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JP5803527B2 (ja) *	2011-09-30	2015-11-04	株式会社ニデック	有機機能性素子
CN110139859A (zh) *	2016-12-28	2019-08-16	昭和电工株式会社	稠合杂多环式化合物及使用了该化合物的导电性聚合物的制造方法

1984
- 1984-06-15 JP JP59121956A patent/JPS6112784A/ja active Granted

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JPS6112784A (ja)	1986-01-21

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2004-06-15	EXPY	Cancellation because of completion of term

Publication	Publication Date	Title
US4795242A (en)	1989-01-03	Conducting substituted polyisothianaphthenes
US4640748A (en)	1987-02-03	Polyisothianaphtene, a new conducting polymer
KR960009685B1 (ko)	1996-07-23	자기 도우프된 중합체의 제조방법
US5589565A (en)	1996-12-31	Water-soluble conducting polyphenylene vinylene polymers
US20100324306A1 (en)	2010-12-23	Electrochromic materials
JPH05214080A (ja)	1993-08-24	フッ素化チオフェン、これらのチオフェンから誘導されたポリマー及びこれらのポリマーを含む導電性ポリマー
EP2338925A1 (fr)	2011-06-29	Composé conjugué d'électron , son procédé de fabrication et polymère conjugué d'électron obtenu à l'aide de celui-ci
US4772940A (en)	1988-09-20	Polymer having isothianaphthene structure and electrochromic display
Kim et al.	2024	Transmissive-to-black electrochromic switching of pendant Viologen polymer with superior long-term operation stability
US5569708A (en)	1996-10-29	Self-doped polymers
JP3464513B2 (ja)	2003-11-10	全固体エレクトロクロミック素子及びその製造方法
EP0164974B1 (fr)	1990-05-23	Polymère ayant une structure d'isothianaphtène et dispositif d'affichage électrochromique
JPH075716B2 (ja)	1995-01-25	Ｎ，ｎ’―ジフェニルベンジジン重合体の製造方法
JPS6224034B2 (fr)	1987-05-26
WO2006029344A2 (fr)	2006-03-16	Materiau electrochrome (ec) vert et dispositif
US5310781A (en)	1994-05-10	Self-doped polymers from polyaniline with bronsted acid groups
US5863981A (en)	1999-01-26	Electrically conducting water-soluble self-doping polyaniline polymers and the aqueous solutions thereof
JP2942710B2 (ja)	1999-08-30	水溶性自己ドープ型導電性ポリマー複合体及びその製造方法
US7298541B2 (en)	2007-11-20	Green electrochromic (EC) material and device
US5760169A (en)	1998-06-02	Self-doped polymers
Qian et al.	2020	The influence of pendent anions on electrochemical and electrochromic properties of thiophene-triphenylamine-based polymeric ionic liquids
JP2012181437A (ja)	2012-09-20	新規有機高分子化合物およびそれを有するエレクトロクロミック素子
JPH02252727A (ja)	1990-10-11	ポリイソチアナフテン系重合体及び導電性材料
JPS6117581A (ja)	1986-01-25	イソチアナフテン構造を有する重合体
JPS6337119A (ja)	1988-02-17	新規な電解重合体およびそれを用いたエレクトロミツク表示素子