EP2162787A1 - Halbelektroaktives material mit organischen verbindungen mit positiver und negativer redoxaktivität, verfahren und kit zur herstellung solch eines materials, elektrisch gesteuerte vorrichtung und glasur mit solch einem halbelektroaktivem material - Google Patents
Halbelektroaktives material mit organischen verbindungen mit positiver und negativer redoxaktivität, verfahren und kit zur herstellung solch eines materials, elektrisch gesteuerte vorrichtung und glasur mit solch einem halbelektroaktivem materialInfo
- Publication number
- EP2162787A1 EP2162787A1 EP08806090A EP08806090A EP2162787A1 EP 2162787 A1 EP2162787 A1 EP 2162787A1 EP 08806090 A EP08806090 A EP 08806090A EP 08806090 A EP08806090 A EP 08806090A EP 2162787 A1 EP2162787 A1 EP 2162787A1
- Authority
- EP
- European Patent Office
- Prior art keywords
- electroactive
- semi
- charges
- ionic
- liquid
- Prior art date
- 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.)
- Withdrawn
Links
- 150000002894 organic compounds Chemical class 0.000 title claims abstract description 42
- 239000011263 electroactive material Substances 0.000 title claims abstract description 38
- 239000000463 material Substances 0.000 title claims description 13
- 238000000034 method Methods 0.000 title claims description 7
- 230000000694 effects Effects 0.000 title description 7
- 229920000642 polymer Polymers 0.000 claims abstract description 67
- 239000007788 liquid Substances 0.000 claims abstract description 33
- 150000001768 cations Chemical class 0.000 claims abstract description 32
- 239000011159 matrix material Substances 0.000 claims abstract description 25
- 238000005325 percolation Methods 0.000 claims abstract description 19
- 230000003381 solubilizing effect Effects 0.000 claims abstract description 9
- 230000003647 oxidation Effects 0.000 claims abstract description 5
- 238000007254 oxidation reaction Methods 0.000 claims abstract description 5
- 238000006722 reduction reaction Methods 0.000 claims abstract description 5
- 239000011521 glass Substances 0.000 claims description 38
- 229920001577 copolymer Polymers 0.000 claims description 29
- 229920001609 Poly(3,4-ethylenedioxythiophene) Polymers 0.000 claims description 27
- 229920002981 polyvinylidene fluoride Polymers 0.000 claims description 24
- 150000003839 salts Chemical class 0.000 claims description 24
- 239000004793 Polystyrene Substances 0.000 claims description 23
- 229920002223 polystyrene Polymers 0.000 claims description 21
- 239000002904 solvent Substances 0.000 claims description 20
- -1 phenothiazine Chemical class 0.000 claims description 19
- 150000001875 compounds Chemical class 0.000 claims description 17
- 239000002608 ionic liquid Substances 0.000 claims description 15
- 238000004519 manufacturing process Methods 0.000 claims description 12
- 230000001590 oxidative effect Effects 0.000 claims description 12
- 239000003792 electrolyte Substances 0.000 claims description 11
- 239000000758 substrate Substances 0.000 claims description 11
- 239000002253 acid Substances 0.000 claims description 10
- 229920001746 electroactive polymer Polymers 0.000 claims description 10
- 239000000203 mixture Substances 0.000 claims description 10
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- 239000004696 Poly ether ether ketone Substances 0.000 claims description 8
- 239000004642 Polyimide Substances 0.000 claims description 8
- MHCFAGZWMAWTNR-UHFFFAOYSA-M lithium perchlorate Chemical compound [Li+].[O-]Cl(=O)(=O)=O MHCFAGZWMAWTNR-UHFFFAOYSA-M 0.000 claims description 8
- 229910001486 lithium perchlorate Inorganic materials 0.000 claims description 8
- 229920002530 polyetherether ketone Polymers 0.000 claims description 8
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- RUOJZAUFBMNUDX-UHFFFAOYSA-N propylene carbonate Chemical compound CC1COC(=O)O1 RUOJZAUFBMNUDX-UHFFFAOYSA-N 0.000 claims description 8
- 238000001704 evaporation Methods 0.000 claims description 7
- 230000008020 evaporation Effects 0.000 claims description 7
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 6
- 230000005540 biological transmission Effects 0.000 claims description 6
- KTWOOEGAPBSYNW-UHFFFAOYSA-N ferrocene Chemical group [Fe+2].C=1C=C[CH-]C=1.C=1C=C[CH-]C=1 KTWOOEGAPBSYNW-UHFFFAOYSA-N 0.000 claims description 6
- 238000009472 formulation Methods 0.000 claims description 6
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- 230000007928 solubilization Effects 0.000 claims description 6
- 238000005063 solubilization Methods 0.000 claims description 6
- BQCIDUSAKPWEOX-UHFFFAOYSA-N 1,1-Difluoroethene Chemical compound FC(F)=C BQCIDUSAKPWEOX-UHFFFAOYSA-N 0.000 claims description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 5
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 claims description 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 4
- 229920003171 Poly (ethylene oxide) Polymers 0.000 claims description 4
- 239000004952 Polyamide Substances 0.000 claims description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 4
- 238000003490 calendering Methods 0.000 claims description 4
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- 238000010438 heat treatment Methods 0.000 claims description 4
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- 229920002037 poly(vinyl butyral) polymer Polymers 0.000 claims description 4
- 229920002647 polyamide Polymers 0.000 claims description 4
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- 229920000867 polyelectrolyte Polymers 0.000 claims description 4
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- 239000005038 ethylene vinyl acetate Substances 0.000 claims description 3
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- 239000004814 polyurethane Substances 0.000 claims description 3
- ZPTRYWVRCNOTAS-UHFFFAOYSA-M 1-ethyl-3-methylimidazol-3-ium;trifluoromethanesulfonate Chemical compound CC[N+]=1C=CN(C)C=1.[O-]S(=O)(=O)C(F)(F)F ZPTRYWVRCNOTAS-UHFFFAOYSA-M 0.000 claims description 2
- OHVSCUACGMLPGP-UHFFFAOYSA-N 1-methyl-10h-phenothiazine 5-oxide Chemical compound N1C2=CC=CC=C2S(=O)C2=C1C(C)=CC=C2 OHVSCUACGMLPGP-UHFFFAOYSA-N 0.000 claims description 2
- CJVYYDCBKKKIPD-UHFFFAOYSA-N 1-n,1-n,2-n,2-n-tetramethylbenzene-1,2-diamine Chemical compound CN(C)C1=CC=CC=C1N(C)C CJVYYDCBKKKIPD-UHFFFAOYSA-N 0.000 claims description 2
- WJFKNYWRSNBZNX-UHFFFAOYSA-N 10H-phenothiazine Chemical compound C1=CC=C2NC3=CC=CC=C3SC2=C1 WJFKNYWRSNBZNX-UHFFFAOYSA-N 0.000 claims description 2
- GVTGSIMRZRYNEI-UHFFFAOYSA-N 5,10-dimethylphenazine Chemical compound C1=CC=C2N(C)C3=CC=CC=C3N(C)C2=C1 GVTGSIMRZRYNEI-UHFFFAOYSA-N 0.000 claims description 2
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Divinylene sulfide Natural products C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims description 2
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 2
- 239000005977 Ethylene Substances 0.000 claims description 2
- KMTRUDSVKNLOMY-UHFFFAOYSA-N Ethylene carbonate Chemical compound O=C1OCCO1 KMTRUDSVKNLOMY-UHFFFAOYSA-N 0.000 claims description 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical class OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 2
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 claims description 2
- 229920000265 Polyparaphenylene Polymers 0.000 claims description 2
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 claims description 2
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 claims description 2
- 150000001298 alcohols Chemical class 0.000 claims description 2
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims description 2
- 150000003863 ammonium salts Chemical class 0.000 claims description 2
- YUWITRJKUGXRGB-UHFFFAOYSA-N bis(2-thiophen-3-ylethyl) decanedioate Chemical compound C1=CSC=C1CCOC(=O)CCCCCCCCC(=O)OCCC=1C=CSC=1 YUWITRJKUGXRGB-UHFFFAOYSA-N 0.000 claims description 2
- 238000004140 cleaning Methods 0.000 claims description 2
- ILZSSCVGGYJLOG-UHFFFAOYSA-N cobaltocene Chemical class [Co+2].C=1C=C[CH-]C=1.C=1C=C[CH-]C=1 ILZSSCVGGYJLOG-UHFFFAOYSA-N 0.000 claims description 2
- OYSLMAQEMAJMCL-UHFFFAOYSA-N ethyl thiophene-3-carboxylate Chemical compound CCOC(=O)C=1C=CSC=1 OYSLMAQEMAJMCL-UHFFFAOYSA-N 0.000 claims description 2
- 239000008187 granular material Substances 0.000 claims description 2
- 150000004693 imidazolium salts Chemical class 0.000 claims description 2
- 238000010348 incorporation Methods 0.000 claims description 2
- 150000002576 ketones Chemical class 0.000 claims description 2
- 238000003475 lamination Methods 0.000 claims description 2
- 150000002825 nitriles Chemical class 0.000 claims description 2
- 229950000688 phenothiazine Drugs 0.000 claims description 2
- 150000002990 phenothiazines Chemical class 0.000 claims description 2
- 229920002098 polyfluorene Polymers 0.000 claims description 2
- 229920000137 polyphosphoric acid Polymers 0.000 claims description 2
- 229920000128 polypyrrole Polymers 0.000 claims description 2
- 229920001021 polysulfide Polymers 0.000 claims description 2
- 230000001681 protective effect Effects 0.000 claims description 2
- WVIICGIFSIBFOG-UHFFFAOYSA-N pyrylium Chemical compound C1=CC=[O+]C=C1 WVIICGIFSIBFOG-UHFFFAOYSA-N 0.000 claims description 2
- 150000004053 quinones Chemical class 0.000 claims description 2
- NLDYACGHTUPAQU-UHFFFAOYSA-N tetracyanoethylene Chemical group N#CC(C#N)=C(C#N)C#N NLDYACGHTUPAQU-UHFFFAOYSA-N 0.000 claims description 2
- 125000003831 tetrazolyl group Chemical group 0.000 claims description 2
- 229930192474 thiophene Natural products 0.000 claims description 2
- ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 claims description 2
- 150000008648 triflates Chemical class 0.000 claims description 2
- ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 claims description 2
- 238000005406 washing Methods 0.000 claims description 2
- 125000005678 ethenylene group Chemical class [H]C([*:1])=C([H])[*:2] 0.000 claims 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 2
- XHZPRMZZQOIPDS-UHFFFAOYSA-N 2-Methyl-2-[(1-oxo-2-propenyl)amino]-1-propanesulfonic acid Chemical compound OS(=O)(=O)CC(C)(C)NC(=O)C=C XHZPRMZZQOIPDS-UHFFFAOYSA-N 0.000 claims 1
- JOWXBGIZDALBJW-UHFFFAOYSA-N 3h-dioxepine Chemical compound C1OOC=CC=C1 JOWXBGIZDALBJW-UHFFFAOYSA-N 0.000 claims 1
- 229910006069 SO3H Inorganic materials 0.000 claims 1
- 238000010276 construction Methods 0.000 claims 1
- 239000000945 filler Substances 0.000 claims 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims 1
- VWBWQOUWDOULQN-UHFFFAOYSA-N nmp n-methylpyrrolidone Chemical compound CN1CCCC1=O.CN1CCCC1=O VWBWQOUWDOULQN-UHFFFAOYSA-N 0.000 claims 1
- 238000010422 painting Methods 0.000 claims 1
- 239000002861 polymer material Substances 0.000 claims 1
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 claims 1
- BFKJFAAPBSQJPD-UHFFFAOYSA-N tetrafluoroethene Chemical group FC(F)=C(F)F BFKJFAAPBSQJPD-UHFFFAOYSA-N 0.000 claims 1
- 239000010410 layer Substances 0.000 description 57
- 239000002033 PVDF binder Substances 0.000 description 21
- 239000000243 solution Substances 0.000 description 13
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 9
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 6
- DOIRQSBPFJWKBE-UHFFFAOYSA-N dibutyl phthalate Chemical compound CCCCOC(=O)C1=CC=CC=C1C(=O)OCCCC DOIRQSBPFJWKBE-UHFFFAOYSA-N 0.000 description 6
- 229920006370 Kynar Polymers 0.000 description 4
- 229910052751 metal Inorganic materials 0.000 description 4
- 239000002184 metal Substances 0.000 description 4
- XOLBLPGZBRYERU-UHFFFAOYSA-N tin dioxide Chemical compound O=[Sn]=O XOLBLPGZBRYERU-UHFFFAOYSA-N 0.000 description 4
- 230000002745 absorbent Effects 0.000 description 3
- 239000002250 absorbent Substances 0.000 description 3
- 239000011149 active material Substances 0.000 description 3
- 239000000853 adhesive Substances 0.000 description 3
- 230000001070 adhesive effect Effects 0.000 description 3
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- 238000002845 discoloration Methods 0.000 description 3
- 239000008151 electrolyte solution Substances 0.000 description 3
- 238000007654 immersion Methods 0.000 description 3
- 229910003437 indium oxide Inorganic materials 0.000 description 3
- PJXISJQVUVHSOJ-UHFFFAOYSA-N indium(iii) oxide Chemical compound [O-2].[O-2].[O-2].[In+3].[In+3] PJXISJQVUVHSOJ-UHFFFAOYSA-N 0.000 description 3
- 229910052718 tin Inorganic materials 0.000 description 3
- 239000011787 zinc oxide Substances 0.000 description 3
- ALJHHTHBYJROOG-UHFFFAOYSA-N 7-(dimethylamino)phenothiazin-3-one Chemical compound C1=CC(=O)C=C2SC3=CC(N(C)C)=CC=C3N=C21 ALJHHTHBYJROOG-UHFFFAOYSA-N 0.000 description 2
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 2
- 229910006404 SnO 2 Inorganic materials 0.000 description 2
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 2
- 150000008043 acidic salts Chemical class 0.000 description 2
- 238000004040 coloring Methods 0.000 description 2
- 230000000763 evoking effect Effects 0.000 description 2
- 238000010030 laminating Methods 0.000 description 2
- MCVFFRWZNYZUIJ-UHFFFAOYSA-M lithium;trifluoromethanesulfonate Chemical compound [Li+].[O-]S(=O)(=O)C(F)(F)F MCVFFRWZNYZUIJ-UHFFFAOYSA-M 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- 229920001200 poly(ethylene-vinyl acetate) Polymers 0.000 description 2
- 229920001798 poly[2-(acrylamido)-2-methyl-1-propanesulfonic acid] polymer Polymers 0.000 description 2
- 239000005020 polyethylene terephthalate Substances 0.000 description 2
- 229920000139 polyethylene terephthalate Polymers 0.000 description 2
- 238000005204 segregation Methods 0.000 description 2
- 238000010186 staining Methods 0.000 description 2
- AKRWNTONLXDQJE-UHFFFAOYSA-N 2-thiophen-3-ylethyl octanoate Chemical compound CCCCCCCC(=O)OCCC=1C=CSC=1 AKRWNTONLXDQJE-UHFFFAOYSA-N 0.000 description 1
- SDFLTYHTFPTIGX-UHFFFAOYSA-N 9-methylcarbazole Chemical compound C1=CC=C2N(C)C3=CC=CC=C3C2=C1 SDFLTYHTFPTIGX-UHFFFAOYSA-N 0.000 description 1
- 239000004604 Blowing Agent Substances 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- 229910004298 SiO 2 Inorganic materials 0.000 description 1
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-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
- 230000003667 anti-reflective effect Effects 0.000 description 1
- 229910052787 antimony Inorganic materials 0.000 description 1
- WATWJIUSRGPENY-UHFFFAOYSA-N antimony atom Chemical compound [Sb] WATWJIUSRGPENY-UHFFFAOYSA-N 0.000 description 1
- INDFXCHYORWHLQ-UHFFFAOYSA-N bis(trifluoromethylsulfonyl)azanide;1-butyl-3-methylimidazol-3-ium Chemical compound CCCCN1C=C[N+](C)=C1.FC(F)(F)S(=O)(=O)[N-]S(=O)(=O)C(F)(F)F INDFXCHYORWHLQ-UHFFFAOYSA-N 0.000 description 1
- LRESCJAINPKJTO-UHFFFAOYSA-N bis(trifluoromethylsulfonyl)azanide;1-ethyl-3-methylimidazol-3-ium Chemical compound CCN1C=C[N+](C)=C1.FC(F)(F)S(=O)(=O)[N-]S(=O)(=O)C(F)(F)F LRESCJAINPKJTO-UHFFFAOYSA-N 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- DQXBYHZEEUGOBF-UHFFFAOYSA-N but-3-enoic acid;ethene Chemical compound C=C.OC(=O)CC=C DQXBYHZEEUGOBF-UHFFFAOYSA-N 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 239000012792 core layer Substances 0.000 description 1
- 230000008021 deposition Effects 0.000 description 1
- 238000007598 dipping method Methods 0.000 description 1
- 150000002019 disulfides Chemical class 0.000 description 1
- 239000007772 electrode material Substances 0.000 description 1
- 239000005329 float glass Substances 0.000 description 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- 239000010931 gold Substances 0.000 description 1
- 229920001519 homopolymer Polymers 0.000 description 1
- 238000005470 impregnation Methods 0.000 description 1
- 229910052738 indium Inorganic materials 0.000 description 1
- 239000011256 inorganic filler Substances 0.000 description 1
- 229910003475 inorganic filler Inorganic materials 0.000 description 1
- 238000005342 ion exchange Methods 0.000 description 1
- 230000031700 light absorption Effects 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 229910000480 nickel oxide Inorganic materials 0.000 description 1
- GNRSAWUEBMWBQH-UHFFFAOYSA-N oxonickel Chemical compound [Ni]=O GNRSAWUEBMWBQH-UHFFFAOYSA-N 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 239000004417 polycarbonate Substances 0.000 description 1
- 229920000515 polycarbonate Polymers 0.000 description 1
- 239000013047 polymeric layer Substances 0.000 description 1
- 239000011970 polystyrene sulfonate Substances 0.000 description 1
- 229960002796 polystyrene sulfonate Drugs 0.000 description 1
- 239000005077 polysulfide Substances 0.000 description 1
- 150000008117 polysulfides Polymers 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 description 1
- 238000006479 redox reaction Methods 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 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
- 239000011877 solvent mixture Substances 0.000 description 1
- 239000003115 supporting electrolyte Substances 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 229910001887 tin oxide Inorganic materials 0.000 description 1
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 description 1
- 229910052721 tungsten Inorganic materials 0.000 description 1
- 239000010937 tungsten Substances 0.000 description 1
- 238000002604 ultrasonography Methods 0.000 description 1
Classifications
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B32—LAYERED PRODUCTS
- B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
- B32B17/00—Layered products essentially comprising sheet glass, or glass, slag, or like fibres
- B32B17/06—Layered products essentially comprising sheet glass, or glass, slag, or like fibres comprising glass as the main or only constituent of a layer, next to another layer of a specific material
- B32B17/10—Layered products essentially comprising sheet glass, or glass, slag, or like fibres comprising glass as the main or only constituent of a layer, next to another layer of a specific material of synthetic resin
- B32B17/10005—Layered products essentially comprising sheet glass, or glass, slag, or like fibres comprising glass as the main or only constituent of a layer, next to another layer of a specific material of synthetic resin laminated safety glass or glazing
- B32B17/10009—Layered products essentially comprising sheet glass, or glass, slag, or like fibres comprising glass as the main or only constituent of a layer, next to another layer of a specific material of synthetic resin laminated safety glass or glazing characterized by the number, the constitution or treatment of glass sheets
- B32B17/10036—Layered products essentially comprising sheet glass, or glass, slag, or like fibres comprising glass as the main or only constituent of a layer, next to another layer of a specific material of synthetic resin laminated safety glass or glazing characterized by the number, the constitution or treatment of glass sheets comprising two outer glass sheets
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K9/00—Tenebrescent materials, i.e. materials for which the range of wavelengths for energy absorption is changed as a result of excitation by some form of energy
- C09K9/02—Organic tenebrescent materials
-
- G—PHYSICS
- G02—OPTICS
- G02F—OPTICAL DEVICES OR ARRANGEMENTS FOR THE CONTROL OF LIGHT BY MODIFICATION OF THE OPTICAL PROPERTIES OF THE MEDIA OF THE ELEMENTS INVOLVED THEREIN; NON-LINEAR OPTICS; FREQUENCY-CHANGING OF LIGHT; OPTICAL LOGIC ELEMENTS; OPTICAL ANALOGUE/DIGITAL CONVERTERS
- G02F1/00—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics
- G02F1/01—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour
- G02F1/15—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour based on an electrochromic effect
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- G—PHYSICS
- G02—OPTICS
- G02F—OPTICAL DEVICES OR ARRANGEMENTS FOR THE CONTROL OF LIGHT BY MODIFICATION OF THE OPTICAL PROPERTIES OF THE MEDIA OF THE ELEMENTS INVOLVED THEREIN; NON-LINEAR OPTICS; FREQUENCY-CHANGING OF LIGHT; OPTICAL LOGIC ELEMENTS; OPTICAL ANALOGUE/DIGITAL CONVERTERS
- G02F1/00—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics
- G02F1/01—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour
- G02F1/15—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour based on an electrochromic effect
- G02F1/1503—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour based on an electrochromic effect caused by oxidation-reduction reactions in organic liquid solutions, e.g. viologen solutions
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- G—PHYSICS
- G02—OPTICS
- G02F—OPTICAL DEVICES OR ARRANGEMENTS FOR THE CONTROL OF LIGHT BY MODIFICATION OF THE OPTICAL PROPERTIES OF THE MEDIA OF THE ELEMENTS INVOLVED THEREIN; NON-LINEAR OPTICS; FREQUENCY-CHANGING OF LIGHT; OPTICAL LOGIC ELEMENTS; OPTICAL ANALOGUE/DIGITAL CONVERTERS
- G02F1/00—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics
- G02F1/01—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour
- G02F1/15—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour based on an electrochromic effect
- G02F1/1514—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour based on an electrochromic effect characterised by the electrochromic material, e.g. by the electrodeposited material
- G02F1/1516—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour based on an electrochromic effect characterised by the electrochromic material, e.g. by the electrodeposited material comprising organic material
- G02F1/15165—Polymers
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- G—PHYSICS
- G02—OPTICS
- G02F—OPTICAL DEVICES OR ARRANGEMENTS FOR THE CONTROL OF LIGHT BY MODIFICATION OF THE OPTICAL PROPERTIES OF THE MEDIA OF THE ELEMENTS INVOLVED THEREIN; NON-LINEAR OPTICS; FREQUENCY-CHANGING OF LIGHT; OPTICAL LOGIC ELEMENTS; OPTICAL ANALOGUE/DIGITAL CONVERTERS
- G02F1/00—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics
- G02F1/01—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour
- G02F1/15—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour based on an electrochromic effect
- G02F2001/1502—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour based on an electrochromic effect complementary cell
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T156/00—Adhesive bonding and miscellaneous chemical manufacture
- Y10T156/10—Methods of surface bonding and/or assembly therefor
- Y10T156/1002—Methods of surface bonding and/or assembly therefor with permanent bending or reshaping or surface deformation of self sustaining lamina
- Y10T156/1039—Surface deformation only of sandwich or lamina [e.g., embossed panels]
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/24—Structurally defined web or sheet [e.g., overall dimension, etc.]
- Y10T428/24942—Structurally defined web or sheet [e.g., overall dimension, etc.] including components having same physical characteristic in differing degree
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/31504—Composite [nonstructural laminate]
Definitions
- SEMI-ELECTROACTIVE MATERIAL COMPRISING ORGANIC COMPOUNDS WITH POSITIVE OR NEGATIVE REDOX ACTIVITY, METHOD AND KIT FOR PRODUCING SAID MATERIAL, ELECTROCOMMANDABLE DEVICE AND GLAZING USING SUCH SEMI-ELECTROACTIVE MATERIAL
- the present invention relates to an electroactive material also said semi-electroactive device for electrically controllable said variable optical properties and / or energy, said semi-electroactive material containing organic compounds with positive or negative redox activity, on a method and a kit of manufacture of this material, on an electrically controllable device comprising a self-supporting layer of polymer with complementary redox activity, namely respectively negative or positive and on glazings using such a semi-electroactive material.
- the electroactive material (or system) of the invention is sometimes referred to interchangeably as a semi-electroactive material (or system), evoking the fact that this material (or system) is capable of forming an electrochemical half-cell.
- Such a device can be defined generally as comprising the following stack of layers: a first substrate with a glass function;
- a second electronically conducting layer with an associated current supply A second electronically conducting layer with an associated current supply
- Electroactive systems with known layers comprise two separate layers of electroactive material by an electrolyte, the electroactive material of at least one of the two layers being electrochromic.
- the two electroactive materials are electrochromic materials, these may be identical or different.
- one of the electroactive materials is electrochromic and the other is not, it will act as a counterelectrode not participating in the process of coloring and discoloration of the system. Under the action of an electric current, the ionic charges of the electrolyte insert into one of the layers of electrochromic material and disinhibit the other layer of electrochromic material or counterelectrode to obtain a contrast of color.
- PEDOT poly (3,4-ethylenedioxythiophene)
- PEDOT poly (3,4-ethylenedioxythiophene)
- Such electroactive systems are not always satisfactory, in particular require a relatively high voltage (greater than 2V) to obtain an acceptable color contrast for the commercial operation of the electrically controllable device.
- the electroactive systems with known electroactive organic compounds comprise an active medium composed of a solvent in which at least two organic electroactive compounds are solubilized, one being an electrochromic material and the other being a counter-electrode material which can also be electrochromic.
- a polymer can be used as a thickener.
- Such systems work by reaction oxidation and reduction of electroactive compounds. Salt can also be added to facilitate charge transport and oxidation-reduction reactions.
- the applicant company has sought a solution to these problems, and has discovered on this occasion a new structure of polymer / organic hybrid electroactive system that allows coloring at a low voltage (less than 2V). Such a decrease in the coloration potential has the effect of increasing the durability of the electrically controllable device, the electroactive medium and the electronically conductive layers of this device being less electrochemically stressed.
- one of the electroactive compounds is in the form of a polymer layer, the segregation phenomena are avoided.
- an electrochemically active, inorganic or polymeric layer which is negative, that is to say which can be reduced and / or accept electrons and cations acting as compensation charges, such as an oxide layer; of tungsten, polyviologen or polythiophene such as PEDOT, or positive, ie which can oxidize and / or eject electrons and cations acting as compensation charges, such as nickel oxide layer or polyaniline; and an electrolyte containing at least one redox active material which may be a positive redox active material such as a metallocene, or a negative redox active material such as a viologen, depending on whether the electrochemically active polymer layer is negative or positive.
- US 6 178 034 B1 also discloses systems of the aforementioned type comprising an electrochromic polymer layer and an electrochromic non-polymer organic compound electrolytic layer. Lists of these polymers and compounds are presented herein but without description of any need to associate complementary staining components.
- the subject of the present invention is therefore a semi-electroactive material of electrically controllable device with variable optical / energy properties, characterized in that it comprises a self-supporting polymer matrix in which is inserted an electroactive system comprising or consisting of:
- At least one electroactive organic compound capable of oxidizing and / or ejecting electrons and cations acting as compensation charges; or at least one electroactive organic compound capable of being reduced and / or of accepting electrons and cations acting as compensation charges;
- ions acting as compensation charges are meant ions Li + , H + , etc., which can be inserted into or disinsert in the electroactive compounds at the same time as the electrons.
- An electroactive organic compound capable of oxidizing and / or ejecting electrons and cations acting as compensation charges means a compound with a positive redox activity, which may be an anodic electrochrome or a non-electrochromic compound. , playing then only the role of reservoir ionic charges or against electrode.
- An electroactive organic compound capable of being reduced and / or of accepting electrons and cations acting as compensation charges means a compound with negative redox activity, which may be a cathodic electrochromic or a non-electrochromic compound, then playing only the role of reservoir ionic charges or against electrode.
- the ionic charges may be borne by the electroactive organic compound (s) and / or by at least one ionic salt and / or at least one solubilized acid in said liquid and / or said self-supporting polymer matrix.
- the solubilizing liquid may consist of a solvent or a mixture of solvents and / or at least one ionic liquid or molten salt at ambient temperature, the said ionic liquid or molten salt, or the said ionic liquids or molten salts then constituting a solubilization liquid.
- the electroactive organic compound (s) capable of being reduced and / or of accepting electrons and cations acting as compensation charges may be chosen from bipyridiniums or viologenes such as 1,1'-diethyl-4-diperchlorate, 4 '- bipyridinium, pyraziniums, pyrimidiniums, quinoxaliniums, pyryliums, pyridiniums, tetrazoliums, verdazyls, quinones, quinodimethanes, tricyanovinylbenzenes, tetracyanoethylene, polysulfides and disulfides, and all polymeric derivatives electroactive compounds of the electroactive compounds which have just been mentioned.
- bipyridiniums or viologenes such as 1,1'-diethyl-4-diperchlorate, 4 '- bipyridinium, pyraziniums, pyrimidiniums, quinoxaliniums, pyryliums,
- the one or more electroactive organic compounds capable of oxidizing and / or ejecting electrons and cations acting as compensation charges can be chosen from metallocenes, such as cobaltocenes, ferrocenes, N, N, N N, N'-tetramethylphenylenediamine (TMPD), phenothiazines such as phenothiazine, dihydrophenazines such as 5,10-dihydro-5,10-dimethylphenazine, reduced methylphenothiazone (MPT), methylene violet bernthsen (MVB), Verdazyls, as well as all derivatives electroactive polymers of the electroactive compounds which have just been mentioned.
- metallocenes such as cobaltocenes, ferrocenes, N, N, N N N, N'-tetramethylphenylenediamine (TMPD)
- phenothiazines such as phenothiazine
- dihydrophenazines such
- the ionic salt (s) may be chosen from lithium perchlorate, trifluoromethanesulfonate or triflate salts, trifluoromethanesulfonylimide salts and ammonium salts.
- the acid (s) may be chosen from sulfuric acid (H 2 SO 4 ), triflic acid (CF 3 SO 3 H), phosphoric acid (H 3 PO 4 ) and polyphosphoric acid (H n + 2 P n 0 3n + i).
- concentration of the ionic salt (s) and / or acid (s) in the solvent or solvent mixture is in particular less than or equal to 5 moles / liter, preferably less than or equal to 2 moles / liter, more or less more preferred, less than or equal to 1 mole / liter.
- the or each solvent may be chosen from those having a boiling point of at least 95 ° C., preferably at least 150 ° C.
- the solvent (s) may be chosen from dimethylsulfoxide, N, N-dimethylformamide, N, N-dimethylacetamide, propylene carbonate, ethylene carbonate and N-methyl-2-pyrrolidone (1-methyl-2).
- pyrrolidinone gamma-butyrolactone, ethylene glycols, alcohols, ketones, nitriles and water.
- the ionic liquid or liquids may be chosen from imidazolium salts, such as 1-ethyl-3-methylimidazolium tetrafluoroborate (emim-BF 4 ), 1-ethyl-3-methylimidazolium trifluoromethanesulfonate (emim-CF 3 SO 3 ), 1-ethyl-3-methylimidazolium bis (trifluoromethylsulfonyl) imide (emim-N (CF 3 SO 2 ) 2 or emim-TSFI) and 1-butyl-3-methylimidazolium bis (trifluoromethylsulphonyl) imide (bmim-N ( CF 3 SO 2 ) 2 or bmim-TSFI).
- imidazolium salts such as 1-ethyl-3-methylimidazolium tetrafluoroborate (emim-BF 4 ), 1-ethyl-3-methylimidazolium trifluoromethanesulf
- the autosupported polymer matrix may consist of at least one polymer layer in which said liquid has penetrated to the core.
- the matrix polymer (s) and the liquid may be chosen so that the self-supporting active medium withstands a temperature corresponding to the temperature necessary for a subsequent lamination or calendering step, namely at a temperature of at least 80 ° C. in particular of at least 100 ° C.
- the polymer constituting at least one layer may be a homo- or copolymer in the form of a non-porous film capable of swelling in said liquid.
- the film has in particular a thickness of less than 1 mm, preferably of 10 to 500 ⁇ m, more preferably of 50 to 120 ⁇ m.
- the polymer constituting at least one layer may also be a homo- or copolymer in the form of a porous film, said porous film optionally being capable of swelling in the liquid comprising ionic charges and whose porosity after swelling is chosen for allow the percolation of the ionic charges in the thickness of the film impregnated with liquid.
- Said film then has a thickness of less than 1 mm, preferably less than 800 ⁇ m, more preferably 10 to 500 ⁇ m, and even more preferably 50 to 120 ⁇ m.
- the polymer or the polymers of the polymer matrix are advantageously chosen so as to be able to withstand laminating and calendering conditions, possibly under heating.
- the polymeric material constituting at least one layer may be chosen from:
- the homo- or copolymers having no ionic charges in which case they are borne by the electroactive organic compound (s) and / or by at least one solubilized ionic or acidic salt and / or by at least one ionic liquid or salt; melted; homo or copolymers comprising ionic charges, in which case additional charges making it possible to increase the percolation rate may be carried by the electroactive organic compound (s) and / or by at least one solubilized ionic or acidic salt and / or by minus an ionic liquid or molten salt; and
- Mixtures of at least one homo- or copolymer not bearing ionic charges and at least one homo- or copolymer containing ionic charges, in which case additional charges making it possible to increase the percolation rate may be carried by the or the electroactive organic compounds and / or by at least one ionic salt or solubilized acid and / or by at least one ionic liquid or molten salt.
- the polymer matrix may consist of a film based on a homo- or copolymer comprising ionic charges, capable of giving itself a film essentially capable of ensuring the desired percolation rate for the electroactive system or a speed of percolation greater than this and a homo- or copolymer with or without ionic charges, able to give by itself a film that does not necessarily ensure the desired percolation rate but essentially able to ensure the holding mechanically, the contents of each of these two homo- or copolymers being adjusted so that both the desired percolation rate and the mechanical strength of the resulting self-supporting organic active medium are ensured.
- the polymer or polymers of the polymer matrix not comprising ionic charges may be chosen from copolymers of ethylene, vinyl acetate and optionally at least one other comonomer, such as the ethylene-vinyl acetate copolymers (EVA); polyurethane (PU); polyvinyl butyral (PVB); polyimides (PI); polyamides (PA); polystyrene
- EVA ethylene-vinyl acetate copolymers
- PU polyurethane
- PVB polyvinyl butyral
- PI polyimides
- PA polyamides
- PS polyvinylidene fluoride
- PVDF polyvinylidene fluoride
- PEEK polyether ether ketones
- the polymers are chosen from the same family as they are prepared in the form of porous or non-porous films, the porosity being provided by the blowing agent used during the manufacture of the film.
- Preferred polymers in the case of the non-porous film include polyurethane (PU) or copolymers of ethylene-vinyl acetate (EVA).
- Preferred polymers in the case of the porous film include polyvinylidene fluoride.
- the polymer or polymers of the polymer matrix bearing ionic or polyelectrolyte charges may be chosen from sulphonated polymers which have been exchanged for H + ions of SO 3 H groups by the ions of the desired ionic charges, this ion exchange having taken place before and / or simultaneously with the swelling of the polyelectrolyte in the liquid having ionic charges.
- the sulphonated polymer may be chosen from sulphonated tetrafluoroethylene copolymers, sulphonated polystyrenes (PSS), sulphonated polystyrene copolymers, poly (2-acrylamido-2-methyl-1-propanesulfonic acid) (PAMPS), polyetheretherketones (PEEK ) sulphonated and sulphonated polyimides.
- PSS sulphonated polystyrenes
- PAMPS poly (2-acrylamido-2-methyl-1-propanesulfonic acid)
- PEEK polyetheretherketones
- the support may comprise from one to three layers.
- a stack of at least two layers may have been formed from electrolyte polymer layers and / or non-electrolytes before penetration to the heart of the liquid, then was inflated by said liquid.
- the two outer layers of the stack may be low-swelling layers to promote the mechanical strength of said material and the core layer is a high-swelling layer to promote the percolation rate of the ionic charges.
- the self-supporting polymer matrix may be nanostructured by the incorporation of nanoparticles of inorganic fillers or nanoparticles, in particular of SiO 2 nanoparticles, in particular by a few percent with respect to the mass of polymer in the support. This makes it possible to improve certain properties of said support such as the mechanical strength.
- the present invention also relates to a method for manufacturing a semi-electroactive material as defined above, characterized in that polymer granules are mixed with a solvent and, if it is desired to manufacture a porous polymer matrix, a pore-forming agent, pouring the resulting formulation on a support and after evaporation of the solvent, removing the pore-forming agent by washing in a suitable solvent for example if it was not removed during the evaporation of the above-mentioned solvent, the resulting self-supported film is removed, then the impregnation of said film is carried out by the solubilization liquid of the semi-electroactive system, and then, if necessary, draining is carried out.
- the immersion can then be carried out for a period of 2 minutes to 3 hours.
- Immersion can be carried out under heating, for example at a temperature of 40 to 80 ° C.
- Immersion can also be performed with the application of ultrasound to aid in the penetration of the solubilizing liquid into the matrix.
- the present invention also relates to a kit for manufacturing the electroactive material as defined above, characterized in that it consists of:
- the present invention also relates to an electrically controllable device comprising the following stack of layers:
- a second electronically conducting layer with an associated current supply A second electronically conducting layer with an associated current supply
- the electroactive system consists of the following stack of layers: a semi-electroactive material as defined above; and
- Cations acting as compensation charges can also be inserted or disinserted in the electroactive polymers of the self-supporting layer.
- the substrates with a glass function are chosen in particular from glass (float glass, etc.) and transparent polymers, such as poly (methyl methacrylate) (PMMA), polycarbonate (PC), polyethylene terephthalate (PET), polyethylene naphthoate (PEN) and cycloolefin copolymers (COC).
- PMMA poly (methyl methacrylate)
- PC polycarbonate
- PET polyethylene terephthalate
- PEN polyethylene naphthoate
- COC cycloolefin copolymers
- the electronically conductive layers are in particular metal-type layers, such as layers of silver, gold, platinum and copper; or transparent conductive oxide (TCO) type layers, such as tin doped indium oxide (In 2 Os: Sn or ITO), antimony doped indium oxide (In 2 Os: S b ), tin oxide fluorine-doped (SnO 2 : F) and zinc oxide doped with aluminum (ZnO: Al); or TCO / metal / TCO multilayers, the TCO and the metal being in particular chosen from those enumerated above; or NiC r / metal / NiC r multilayers, the metal being in particular chosen from those enumerated above.
- TCO transparent conductive oxide
- the electroconductive materials are generally transparent oxides whose electronic conduction has been amplified by doping such as In 2 Os: Sn, In 2 Os: Sb, ZnO: Al or SnO 2 : F .
- Tin doped indium oxide In 2 O 3 : Sn or ITO
- one of the electroconductive materials may be metallic in nature.
- the polymer capable of being reduced and / or of accepting electrons and cations acting as compensation charges is chosen from among the polyviologenes is chosen in particular from polyviologenes, polymers containing units or groups bispyridinium, pyrylium, pyrazinium, or quinoxalium, polyarylenes and polyheteroarylenes such as polythiophenes such as for example poly (3,4-ethylenedioxythiophene) (PEDOT), poly [3,3-dimethyl-3,4-dihydro-2H-thieno-3, 4-b) dioxepine] (ProD0T-Me 2 ), polyisothianophtene, polyisothianaphthene (PITN), polyimides, polyquinones and polydisulfides.
- polyviologenes polymers containing units or groups bispyridinium, pyrylium, pyrazinium, or quinoxalium
- polyarylenes and polyheteroarylenes such as poly
- the polymer capable of oxidizing and / or ejecting electrons and cations acting as charges of compensation is chosen in particular from polyarylamines, such as polyanilines, polyarylenes, such as polyphenylenes or polyfluorenes, polyheteroarylenes such as polypyrroles, for instance poly (N-sulfonatopropoxy-3,4-propylenedioxypyrrole) (PProDOP-NPrS) ), polylindoles, thiophene copolymers such as poly [octanoic acid 2-thiophen-3-yl ethyl ester] (POTE), poly [decanedioic acid bis- (2-thiophen-3-yl-ethyl) ester] (PDATE), poly ⁇ 2- [3-thienylcarbonyl) oxy] ethyl-3-thiophene carboxylate ⁇ (PTOET), poly ⁇ 2,3-bis [3-thienylcarbonyl)
- a motor vehicle roof which can be activated autonomously, or a side window or a rear window for a motor vehicle or a rear-view mirror; - a windshield or a portion of the windshield of a motor vehicle, an airplane or a ship, an automobile roof;
- the electrically controllable device can operate in transmission or in reflection.
- the substrates may be transparent, flat or curved, clear or tinted in the mass, opaque or opacified, polygonal in shape or at least partially curved. At least one of the substrates may incorporate another feature, such as solar control, anti-reflective, or self-cleaning functionality.
- the present invention also relates to a method of manufacturing the electrically controllable device as defined above, characterized in that it assembles the various layers that compose it by calendering or laminating possibly under heating. In the case where the electrically controllable device is intended to constitute a glazing unit, the above method also comprises the mounting of the different layers in single or multiple glazing.
- PEDOT / PSS poly (3, 4-ethylenedioxythiophene) / polystyrene sulfonate sold under the name Baytron ® P by the Company "HC Stark”.
- PVDF Poly (vinylidene fluoride) In these examples, was carried out the deposition of wet formulations of PEDOT / PSS (Baytron ® P) following the CPC 105D recipe for "HC Stark” Company.
- the glass used in these examples is a glass provided with an electroconductive layer of SnC> 2: F, sold under the name "K-glass TM” by the company "Pilkington”.
- PVDF films used was poly powder (polyvinylidene fluoride) manufactured by my company "Arkema” under the name “Kynar ®” in 2501 or 2821.
- PVDF Vinyl ® 2501
- dibutyl phthalate 12 g
- acetone 12 g
- the formulation was stirred for two hours and cast on a glass plate. After evaporation of the solvent, the PVDF film was removed from the glass plate under a trickle of water.
- a semi-electroactive solution was prepared by mixing 0.23 g of ferrocene and 0.27 g of sodium perchlorate. lithium in 40 ml of propylene carbonate. The solution was stirred for 1 hour.
- the self-supported semi-electroactive medium was obtained by immersing the PVDF film about 80 microns thick in diethyl ether for 5 minutes and then in the semi- electroactive solution for 5 minutes.
- the PVDF film impregnated with semi-electroactive solution was then wiped between two absorbent papers before being deposited on a bare K-glass glass plate.
- a double-sided adhesive frame was used as a seal and the K-glass plate coated with PEDOT / PSS was deposited on the semi-electroactive film to terminate the electrochromic device.
- the electrochromic device thus manufactured has a light transmission of 42% in the decolorized state, at a voltage of 1.5V and 13.5% in the colored state at a voltage of -1.5V. After 1000 cycles of discoloration and coloration the performance of the electrochromic device remained unchanged.
- - SnO2 layer glass F coated with a layer of PEDOT / PSS; - semi-electroactive system: ferrocene + lithium trifluoromethanesulfonate + propylene carbonate
- An electrochromic device was made using a bare K-glass plate and a K-glass plate on which a layer of PEDOT / PSS had been deposited.
- PVDF Self-supporting film by mixing 3.5 g of PVDF (Kynar ® 2821), 6.5 g of dibutyl phthalate and 12 g of acetone. The formulation was stirred for two hours and cast on a glass plate. After evaporation of the solvent, the PVDF film was removed from the glass plate under a trickle of water.
- a semi-electroactive solution was prepared by mixing 0.23 g of ferrocene and 0.39 g of lithium trifluoromethanesulfonate in 40 ml of propylene carbonate. The solution was stirred for 1 hour.
- the self-supported semi-electroactive medium was obtained by immersing the PVDF film about 80 microns thick in diethyl ether for 5 minutes and then in the semi- electroactive solution for 5 minutes.
- the PVDF film impregnated with semi-electroactive solution was then wiped between two absorbent papers before being deposited on a bare K-glass glass plate.
- a double-sided adhesive frame was used as a seal and the K-glass plate coated with PEDOT / PSS was deposited on the semi-electroactive film to terminate the electrochromic device.
- the electrochromic device thus manufactured has a light transmission of 45% in the decolorized state at a voltage of 1.5V and 15% in the colored state at a voltage of -1.5V. After 100 cycles of discoloration and coloration the performance of the electrochromic device remained unchanged.
- An electrochromic device was manufactured using two K-glass plates on each of which a PEDOT / PSS layer had been deposited (wet 180 micron deposit). Before assembly, the PEDOT / PSS layers were reduced in a solution of acetonitrile and lithium perchlorate at 1M.
- An electrolyte solution was prepared by solubilizing 0.27 g of lithium perchlorate in 40 ml of propylene carbonate. The solution was stirred for 1 hour.
- the self-supporting electrolyte was obtained by dipping for 5 minutes the PVDF film about 80 microns thick 5 minutes in diethyl ether and then 5 minutes in the electrolyte solution.
- the PVDF film impregnated with electrolyte solution was then wiped between two absorbent papers before being deposited on one of the two K-glass plates covered with PEDOT / PSS.
- a double-sided adhesive frame was used as a seal and the second K-glass plate covered with PEDOT / PSS was deposited on the self-supported electrolyte film to terminate the electrochromic device.
- the electrochromic device thus manufactured has a light transmission of 18% in the decolorized state under a voltage of OV and 10.5% in the colored state under a voltage of -2V.
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- Optics & Photonics (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Electrochromic Elements, Electrophoresis, Or Variable Reflection Or Absorption Elements (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
FR0755987A FR2917849B1 (fr) | 2007-06-25 | 2007-06-25 | Materiau semi-electroactif renfermant des composes organiques a activite redox positive ou negative, procede et kit de fabrication de ce materiau, dispositif electrocommandable et vitrages utilisant un tel materiau |
PCT/FR2008/051161 WO2009007602A1 (fr) | 2007-06-25 | 2008-06-25 | Materiau semi-electroactif renfermant des composes organiques a activite redox positive ou negative, procede et kit de fabrication de ce materiau, dispositif electrocommandable et vitrages utilisant un tel materiau semi-electroactif |
Publications (1)
Publication Number | Publication Date |
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EP2162787A1 true EP2162787A1 (de) | 2010-03-17 |
Family
ID=38963091
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
EP08806090A Withdrawn EP2162787A1 (de) | 2007-06-25 | 2008-06-25 | Halbelektroaktives material mit organischen verbindungen mit positiver und negativer redoxaktivität, verfahren und kit zur herstellung solch eines materials, elektrisch gesteuerte vorrichtung und glasur mit solch einem halbelektroaktivem material |
Country Status (9)
Country | Link |
---|---|
US (1) | US20100172011A1 (de) |
EP (1) | EP2162787A1 (de) |
JP (1) | JP2010531379A (de) |
KR (1) | KR20100025534A (de) |
CN (1) | CN101689002A (de) |
BR (1) | BRPI0813399A2 (de) |
CA (1) | CA2692035A1 (de) |
FR (1) | FR2917849B1 (de) |
WO (1) | WO2009007602A1 (de) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP2239626A1 (de) * | 2008-01-31 | 2010-10-13 | Fundacion Cidetec | Bei umgebungstemperatur formulierbare und verwendbare elektrochrome zusammensetzungen mit viologenen |
Families Citing this family (14)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US8183390B1 (en) | 2006-07-24 | 2012-05-22 | The United States Of America As Represented By The Secretary Of The Navy | Bis(thienyl)isopyrazoles and process for preparing and method for using bis(thienyl)isopyrazoles |
US7456295B1 (en) | 2006-11-25 | 2008-11-25 | The United States Of America As Represented By The Secretary Of The Navy | Bis(thienyl)isopyrazoles and process for preparing and method for using bis(thienyl)isopyrazoles |
US8427812B1 (en) | 2008-07-24 | 2013-04-23 | The United States Of America As Represented By The Secretary Of The Navy | Electroactive polymer based supercapacitors including a cathode having BBL or Pry-BBL |
US9782949B2 (en) | 2008-05-30 | 2017-10-10 | Corning Incorporated | Glass laminated articles and layered articles |
AU2011292398A1 (en) | 2010-08-20 | 2013-03-07 | Centre National De La Recherche Scientifique | Films containing electrically conductive polymers |
WO2013142552A1 (en) | 2012-03-21 | 2013-09-26 | Bayer Materialscience Ag | Roll-to-roll manufacturing processes for producing self-healing electroactive polymer devices |
KR20150002811A (ko) * | 2012-04-12 | 2015-01-07 | 바이엘 머티리얼사이언스 아게 | 개선된 성능의 eap 트랜스듀서 |
CN102690646B (zh) * | 2012-06-04 | 2014-10-15 | 仝泽彬 | 一种电致变色材料及电致变色器件 |
EP2885867A4 (de) | 2012-08-16 | 2016-04-13 | Bayer Ip Gmbh | Elektrische anschlüsse für gewalzten dielektrische elastomerwandler |
TWI565737B (zh) | 2015-12-16 | 2017-01-11 | 財團法人工業技術研究院 | 多孔疏水性含氟高分子膜與其形成方法 |
CN105623642B (zh) * | 2016-02-24 | 2017-12-26 | 青岛科技大学 | 一种新型电致变色材料P(6NIIn‑co‑EDOT)及其制备方法 |
KR102596288B1 (ko) * | 2016-11-29 | 2023-10-30 | 엘지디스플레이 주식회사 | 접촉 감응 소자 및 그를 포함하는 표시 장치 |
CN108409964A (zh) * | 2018-05-18 | 2018-08-17 | 东华大学 | 以离子液体为骨架的聚离子液体及其制备方法 |
EP4038450A4 (de) * | 2019-10-02 | 2023-10-25 | Gentex Corporation | Elektrooptische elemente und verfahren zum bilden |
Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
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US5910854A (en) * | 1993-02-26 | 1999-06-08 | Donnelly Corporation | Electrochromic polymeric solid films, manufacturing electrochromic devices using such solid films, and processes for making such solid films and devices |
Family Cites Families (14)
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DE69426040T2 (de) * | 1993-02-26 | 2001-05-17 | Donnelly Corp | Elektrochrome polymerische Festfilme, Herstellung elektrochromer Vorrichtungen mit solchen Filmen, und Verfahren zur Herstellung solcher Festfilme und Vorrichtungen |
WO1996013754A1 (en) * | 1994-10-26 | 1996-05-09 | Donnelly Corporation | Electrochromic devices and methods of preparation |
WO1999032926A1 (fr) * | 1997-12-19 | 1999-07-01 | Nippon Mitsubishi Oil Corporation | Element electrochimique |
ES2164029B1 (es) * | 2000-07-07 | 2003-05-16 | Fico Mirrors Sa | Dispositivo electrocromico y aplicaciones correspondientes. |
US6620342B1 (en) * | 2000-10-23 | 2003-09-16 | Atofina Chemicals, Inc. | Narrow composition distribution polyvinylidene fluoride RECLT films, processes, articles of manufacture and compositions |
US6747780B2 (en) * | 2001-06-25 | 2004-06-08 | University Of Washington | Electrochromic organic polymer synthesis and devices utilizing electrochromic organic polymers |
JP2003015163A (ja) * | 2001-06-27 | 2003-01-15 | Nippon Oil Corp | エレクトロクロミック素子 |
JP2003043526A (ja) * | 2001-07-26 | 2003-02-13 | Nippon Oil Corp | エレクトロクロミック素子 |
JP2004029432A (ja) * | 2002-06-26 | 2004-01-29 | Nippon Oil Corp | エレクトロクロミック素子 |
JP2004029433A (ja) * | 2002-06-26 | 2004-01-29 | Nippon Oil Corp | エレクトロクロミック素子 |
FR2857759B1 (fr) * | 2003-07-16 | 2005-12-23 | Saint Gobain | Film electrocommandable a proprietes optiques et/ou energetiques variables |
JP4184404B2 (ja) * | 2005-12-08 | 2008-11-19 | 日立マクセル株式会社 | 電気化学素子用セパレータおよび電気化学素子 |
JP2007227087A (ja) * | 2006-02-22 | 2007-09-06 | Toin Gakuen | 色素増感型光電変換素子 |
FR2917848B1 (fr) * | 2007-06-25 | 2009-09-25 | Saint Gobain | Materiau electroactif renfermant des composes organiques a activites redox respectivement positive et negative, procede et kit de fabrication de ce materiau, dispositif electrocommandable et vitrages utlisant un tel materiau |
-
2007
- 2007-06-25 FR FR0755987A patent/FR2917849B1/fr not_active Expired - Fee Related
-
2008
- 2008-06-25 CN CN200880022162A patent/CN101689002A/zh active Pending
- 2008-06-25 CA CA002692035A patent/CA2692035A1/fr not_active Abandoned
- 2008-06-25 US US12/666,334 patent/US20100172011A1/en not_active Abandoned
- 2008-06-25 EP EP08806090A patent/EP2162787A1/de not_active Withdrawn
- 2008-06-25 WO PCT/FR2008/051161 patent/WO2009007602A1/fr active Application Filing
- 2008-06-25 JP JP2010514064A patent/JP2010531379A/ja active Pending
- 2008-06-25 BR BRPI0813399 patent/BRPI0813399A2/pt not_active IP Right Cessation
- 2008-06-25 KR KR20097026969A patent/KR20100025534A/ko not_active Application Discontinuation
Patent Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5910854A (en) * | 1993-02-26 | 1999-06-08 | Donnelly Corporation | Electrochromic polymeric solid films, manufacturing electrochromic devices using such solid films, and processes for making such solid films and devices |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP2239626A1 (de) * | 2008-01-31 | 2010-10-13 | Fundacion Cidetec | Bei umgebungstemperatur formulierbare und verwendbare elektrochrome zusammensetzungen mit viologenen |
EP2239626A4 (de) * | 2008-01-31 | 2011-08-03 | Fundacion Cidetec | Bei umgebungstemperatur formulierbare und verwendbare elektrochrome zusammensetzungen mit viologenen |
Also Published As
Publication number | Publication date |
---|---|
KR20100025534A (ko) | 2010-03-09 |
CN101689002A (zh) | 2010-03-31 |
FR2917849B1 (fr) | 2009-09-25 |
BRPI0813399A2 (pt) | 2014-12-30 |
US20100172011A1 (en) | 2010-07-08 |
FR2917849A1 (fr) | 2008-12-26 |
WO2009007602A1 (fr) | 2009-01-15 |
CA2692035A1 (fr) | 2009-01-15 |
JP2010531379A (ja) | 2010-09-24 |
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