CA1043890A - Cellules d'affichage electrochromiques contenant des sels substitues de bipyridinium - Google Patents

Cellules d'affichage electrochromiques contenant des sels substitues de bipyridinium

Info

Publication number: CA1043890A
Authority: CA; Canada
Prior art keywords: cell; group; display cell; image display; compound
Prior art date: 1974-05-17
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

CA200,241A

Other languages

English (en)

Other versions

CA200241S (en

Inventor

Johannes J. Ponjee

Hendrik T. Van Dam

Cornelis J. Schoot

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.)

Koninklijke Philips NV

Original Assignee

Philips Gloeilampenfabrieken NV

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.)

1974-05-17

Filing date

1974-05-17

Publication date

1978-12-05

1974-05-17 Application filed by Philips Gloeilampenfabrieken NV filed Critical Philips Gloeilampenfabrieken NV

1974-05-17 Priority to CA200,241A priority Critical patent/CA1043890A/fr

1978-12-05 Application granted granted Critical

1978-12-05 Publication of CA1043890A publication Critical patent/CA1043890A/fr

Status Expired legal-status Critical Current

Links

239000000126 substance Substances 0.000 title claims description 32
150000003839 salts Chemical class 0.000 title abstract description 7
150000001875 compounds Chemical class 0.000 claims abstract description 44
239000007788 liquid Substances 0.000 claims abstract description 8
CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 claims abstract description 5
239000002244 precipitate Substances 0.000 claims abstract description 5
125000001453 quaternary ammonium group Chemical group 0.000 claims abstract description 4
-1 morpholinocarbonylmethyl group Chemical group 0.000 claims description 13
125000000217 alkyl group Chemical group 0.000 claims description 12
125000004432 carbon atom Chemical group C* 0.000 claims description 12
150000001450 anions Chemical class 0.000 claims description 9
239000000047 product Substances 0.000 claims description 9
239000007864 aqueous solution Substances 0.000 claims description 7
239000007795 chemical reaction product Substances 0.000 claims description 6
150000002500 ions Chemical class 0.000 claims description 6
230000009467 reduction Effects 0.000 claims description 6
239000000243 solution Substances 0.000 claims description 6
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 6
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 4
150000004820 halides Chemical class 0.000 claims description 4
230000002441 reversible effect Effects 0.000 claims description 4
MWVTWFVJZLCBMC-UHFFFAOYSA-N 4,4'-bipyridine Chemical group C1=NC=CC(C=2C=CN=CC=2)=C1 MWVTWFVJZLCBMC-UHFFFAOYSA-N 0.000 claims description 3
125000003342 alkenyl group Chemical group 0.000 claims description 3
238000009835 boiling Methods 0.000 claims description 3
150000001768 cations Chemical class 0.000 claims description 3
229910052736 halogen Inorganic materials 0.000 claims description 3
150000002367 halogens Chemical class 0.000 claims description 3
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
239000003880 polar aprotic solvent Substances 0.000 claims description 3
229910001513 alkali metal bromide Inorganic materials 0.000 claims description 2
125000005078 alkoxycarbonylalkyl group Chemical group 0.000 claims description 2
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
239000000203 mixture Substances 0.000 claims description 2
125000003884 phenylalkyl group Chemical group 0.000 claims description 2
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
125000001814 trioxo-lambda(7)-chloranyloxy group Chemical group *OCl(=O)(=O)=O 0.000 claims 2
125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims 1
150000002825 nitriles Chemical class 0.000 claims 1
229910052794 bromium Inorganic materials 0.000 abstract description 5
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 abstract description 4
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 abstract description 4
238000004040 coloring Methods 0.000 abstract description 3
PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 9
XOLBLPGZBRYERU-UHFFFAOYSA-N tin dioxide Chemical compound O=[Sn]=O XOLBLPGZBRYERU-UHFFFAOYSA-N 0.000 description 8
ROFVEXUMMXZLPA-UHFFFAOYSA-N Bipyridyl Chemical group N1=CC=CC=C1C1=CC=CC=N1 ROFVEXUMMXZLPA-UHFFFAOYSA-N 0.000 description 6
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 6
230000015572 biosynthetic process Effects 0.000 description 6
229910052799 carbon Inorganic materials 0.000 description 6
238000006243 chemical reaction Methods 0.000 description 6
239000000460 chlorine Substances 0.000 description 6
PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 6
229910052737 gold Inorganic materials 0.000 description 6
239000010931 gold Substances 0.000 description 6
JHJLBTNAGRQEKS-UHFFFAOYSA-M sodium bromide Chemical compound [Na+].[Br-] JHJLBTNAGRQEKS-UHFFFAOYSA-M 0.000 description 6
125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 5
239000011347 resin Substances 0.000 description 5
229920005989 resin Polymers 0.000 description 5
229920005439 Perspex® Polymers 0.000 description 4
125000004429 atom Chemical group 0.000 description 4
229910001914 chlorine tetroxide Inorganic materials 0.000 description 4
229910052759 nickel Inorganic materials 0.000 description 4
229910052757 nitrogen Inorganic materials 0.000 description 4
239000004926 polymethyl methacrylate Substances 0.000 description 4
239000000758 substrate Substances 0.000 description 4
125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 4
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 3
238000009792 diffusion process Methods 0.000 description 3
239000011521 glass Substances 0.000 description 3
150000005837 radical ions Chemical class 0.000 description 3
150000003254 radicals Chemical class 0.000 description 3
238000007086 side reaction Methods 0.000 description 3
ULTHEAFYOOPTTB-UHFFFAOYSA-N 1,4-dibromobutane Chemical compound BrCCCCBr ULTHEAFYOOPTTB-UHFFFAOYSA-N 0.000 description 2
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 2
229940077484 ammonium bromide Drugs 0.000 description 2
TZCXTZWJZNENPQ-UHFFFAOYSA-L barium sulfate Chemical compound [Ba+2].[O-]S([O-])(=O)=O TZCXTZWJZNENPQ-UHFFFAOYSA-L 0.000 description 2
230000008901 benefit Effects 0.000 description 2
230000008859 change Effects 0.000 description 2
229910052801 chlorine Inorganic materials 0.000 description 2
239000004922 lacquer Substances 0.000 description 2
239000000463 material Substances 0.000 description 2
238000000034 method Methods 0.000 description 2
125000003136 n-heptyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
WTEVQBCEXWBHNA-YFHOEESVSA-N neral Chemical compound CC(C)=CCC\C(C)=C/C=O WTEVQBCEXWBHNA-YFHOEESVSA-N 0.000 description 2
239000012476 oxidizable substance Substances 0.000 description 2
VLTRZXGMWDSKGL-UHFFFAOYSA-M perchlorate Inorganic materials [O-]Cl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-M 0.000 description 2
BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
229910052709 silver Inorganic materials 0.000 description 2
239000004332 silver Substances 0.000 description 2
101100087530 Caenorhabditis elegans rom-1 gene Proteins 0.000 description 1
WTEVQBCEXWBHNA-UHFFFAOYSA-N Citral Natural products CC(C)=CCCC(C)=CC=O WTEVQBCEXWBHNA-UHFFFAOYSA-N 0.000 description 1
CWYNVVGOOAEACU-UHFFFAOYSA-N Fe2+ Chemical class [Fe+2] CWYNVVGOOAEACU-UHFFFAOYSA-N 0.000 description 1
241000282326 Felis catus Species 0.000 description 1
241001272567 Hominoidea Species 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
WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
101100305983 Mus musculus Rom1 gene Proteins 0.000 description 1
UZIQYAYUUNMDMU-UHFFFAOYSA-N N.[Br+] Chemical compound N.[Br+] UZIQYAYUUNMDMU-UHFFFAOYSA-N 0.000 description 1
229910002651 NO3 Inorganic materials 0.000 description 1
NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 1
229910021607 Silver chloride Inorganic materials 0.000 description 1
229910006853 SnOz Inorganic materials 0.000 description 1
GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 1
239000000010 aprotic solvent Substances 0.000 description 1
229910052788 barium Inorganic materials 0.000 description 1
DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium atom Chemical compound [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 0.000 description 1
159000000009 barium salts Chemical class 0.000 description 1
229940092690 barium sulfate Drugs 0.000 description 1
229940075397 calomel Drugs 0.000 description 1
150000001721 carbon Chemical group 0.000 description 1
239000004568 cement Substances 0.000 description 1
WTEVQBCEXWBHNA-JXMROGBWSA-N citral A Natural products CC(C)=CCC\C(C)=C\C=O WTEVQBCEXWBHNA-JXMROGBWSA-N 0.000 description 1
239000003086 colorant Substances 0.000 description 1
239000004020 conductor Substances 0.000 description 1
230000008878 coupling Effects 0.000 description 1
238000010168 coupling process Methods 0.000 description 1
238000005859 coupling reaction Methods 0.000 description 1
125000004122 cyclic group Chemical group 0.000 description 1
230000007423 decrease Effects 0.000 description 1
238000000151 deposition Methods 0.000 description 1
230000008021 deposition Effects 0.000 description 1
ZOMNIUBKTOKEHS-UHFFFAOYSA-L dimercury dichloride Chemical compound Cl[Hg][Hg]Cl ZOMNIUBKTOKEHS-UHFFFAOYSA-L 0.000 description 1
239000007772 electrode material Substances 0.000 description 1
238000004070 electrodeposition Methods 0.000 description 1
229910052739 hydrogen Inorganic materials 0.000 description 1
239000001257 hydrogen Substances 0.000 description 1
125000004435 hydrogen atom Chemical class [H]* 0.000 description 1
238000007689 inspection Methods 0.000 description 1
229910052740 iodine Inorganic materials 0.000 description 1
QTWZICCBKBYHDM-UHFFFAOYSA-N leucomethylene blue Chemical compound C1=C(N(C)C)C=C2SC3=CC(N(C)C)=CC=C3NC2=C1 QTWZICCBKBYHDM-UHFFFAOYSA-N 0.000 description 1
229910052744 lithium Inorganic materials 0.000 description 1
238000004519 manufacturing process Methods 0.000 description 1
229910052751 metal Inorganic materials 0.000 description 1
239000002184 metal Substances 0.000 description 1
125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
230000003647 oxidation Effects 0.000 description 1
238000007254 oxidation reaction Methods 0.000 description 1
229910052763 palladium Inorganic materials 0.000 description 1
230000008447 perception Effects 0.000 description 1
VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 1
229910052697 platinum Inorganic materials 0.000 description 1
238000002360 preparation method Methods 0.000 description 1
125000004076 pyridyl group Chemical group 0.000 description 1
230000004044 response Effects 0.000 description 1
HKZLPVFGJNLROG-UHFFFAOYSA-M silver monochloride Chemical compound [Cl-].[Ag+] HKZLPVFGJNLROG-UHFFFAOYSA-M 0.000 description 1
YPNVIBVEFVRZPJ-UHFFFAOYSA-L silver sulfate Chemical compound [Ag+].[Ag+].[O-]S([O-])(=O)=O YPNVIBVEFVRZPJ-UHFFFAOYSA-L 0.000 description 1
229910000367 silver sulfate Inorganic materials 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000011734 sodium Substances 0.000 description 1
239000002904 solvent Substances 0.000 description 1
238000003860 storage Methods 0.000 description 1
125000001424 substituent group Chemical group 0.000 description 1
125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 description 1
230000002194 synthesizing effect Effects 0.000 description 1
229920002994 synthetic fiber Polymers 0.000 description 1
229920003002 synthetic resin Polymers 0.000 description 1
239000000057 synthetic resin Substances 0.000 description 1
125000005207 tetraalkylammonium group Chemical group 0.000 description 1
DZLFLBLQUQXARW-UHFFFAOYSA-N tetrabutylammonium Chemical compound CCCC[N+](CCCC)(CCCC)CCCC DZLFLBLQUQXARW-UHFFFAOYSA-N 0.000 description 1
STOSPPMGXZPHKP-UHFFFAOYSA-N tetrachlorohydroquinone Chemical compound OC1=C(Cl)C(Cl)=C(O)C(Cl)=C1Cl STOSPPMGXZPHKP-UHFFFAOYSA-N 0.000 description 1
DDFYFBUWEBINLX-UHFFFAOYSA-M tetramethylammonium bromide Chemical compound [Br-].C[N+](C)(C)C DDFYFBUWEBINLX-UHFFFAOYSA-M 0.000 description 1
OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
230000000007 visual effect Effects 0.000 description 1

Landscapes

Pyridine Compounds (AREA)

CA200,241A 1974-05-17 1974-05-17 Cellules d'affichage electrochromiques contenant des sels substitues de bipyridinium Expired CA1043890A (fr)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
CA200,241A CA1043890A (fr)	1974-05-17	1974-05-17	Cellules d'affichage electrochromiques contenant des sels substitues de bipyridinium

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
CA200,241A CA1043890A (fr)	1974-05-17	1974-05-17	Cellules d'affichage electrochromiques contenant des sels substitues de bipyridinium

Publications (1)

Publication Number	Publication Date
CA1043890A true CA1043890A (fr)	1978-12-05

Family

ID=4100108

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA200,241A Expired CA1043890A (fr)	1974-05-17	1974-05-17	Cellules d'affichage electrochromiques contenant des sels substitues de bipyridinium

Country Status (1)

Country	Link
CA (1)	CA1043890A (fr)

1974
- 1974-05-17 CA CA200,241A patent/CA1043890A/fr not_active Expired

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