Electrochromic solution containing hydrazone compound and device manufactured with same

• US 6,587,251 B2
• Filed: 06/24/2002
• Issued: 07/01/2003
• Est. Priority Date: 09/04/2001
• Status: Expired due to Fees

• Current Assignee: Exon Science, Inc.
• Original Assignee: Exon Science, Inc.
• Inventors: Hsu, Kuang-Mei, Wang, Fu-Shing
• Primary Examiner(s): Dang, Hung Xuan
• Assistant Examiner(s): TRA, TUYEN Q
• Application Number:
  US10/179,142
• Publication Number:
  US 20030063365A1
• Time in Patent Office: 372 Days
• Field of Search: 359/265, 359/266, 359/267, 359/268, 359/269, 359/270, 359/271, 359/272, 359/273, 359/274, 359/275, 564/250, 564/251
• US Class Current: 359/265
• CPC Class Codes: C07C 251/86 having doubly-bound carbon atoms of hydrazone groups bound to carbon atoms of six-membered aromatic rings
• CPC Class Codes: C07D 209/86 with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the ring system
• CPC Class Codes: C07F 17/02 of metals of Groups 8, 9 or 10 of the Periodic System
• CPC Class Codes: C09K 9/02 Organic tenebrescent materials

Abstract

An electrochromic solution includes a hydrazone compound as an anodic compound is disclosed. The hydrazone compound has a general formula (I)

wherein R₁, R₂, R₃, and R₄ are individually selected from a group consisting of hydrogen, alkyl containing 5 to 20 carbon atoms, alkenyl containing 2 to 20 carbon atoms, alkynyl containing 2 to 20 carbon atoms, and aryl containing 5 to 20 atoms which are unsubstituted or optionally substituted with one or more ester, ether, aryl, amine, thioester, alkyl, alkoxy, alkene, alkyne, CN, F, Cl, Br, I and/or organometallcene functional group.

Claims

1. An electrochromic device for use in a mirror for performing color change of the mirror in response to a voltage applied thereto, comprising:

a first transparent substrate;

a second transparent substrate positioned substantially parallel to said first transparent substrate, and spaced apart from said first transparent substrate by a predetermined clearance to form a space therebetween;

an electrochromic composition including a hydrazone compound, disposed in said space between said first and second transparent substrates;

a seal disposed between said first and second transparent substrates for retaining said electrochromic composition in said space; and

a pair of transparent electrodes provided on opposite surfaces of said first and second transparent substrates facing said space for providing said voltage for said electrochromic composition to perform color change

wherein said hydrazone compound is a member selected from a group consisting of 4-diphenylamino-benzaldehyde-N,N-diphenylhydrazone, 9-ethyl-carbazole-3-aldehyde-N,N-methylphenyhydrazone, Ferrocenemethylketone-N,N-diphenylhydrazone, Benzophenone-N,N-diphenylhydrozone, Acetone 2,2-dimethylhydrazone, 2-pentanone 2-ethyl-2-methyihydrazone, 2-ethylbutanal 1-ethyl-1-propylhydrazone, 2-ethyl-2-nonanone 2-hexyl-2-propylhydrazone, (E)-3-nonen-2-one 2-butyl-2-propyihydrazone, 2-hexanone 2-[(E)-2-butenyl]-2-[(Z)-2-butenyl]hydrazone, 4-pentyn-2-one 2,2-dipropyihydrazone, 1-penten-3-one 3,3-dimethyihydrazone, 2-hexanone 2,2-diphenyihydrazone, 3-heptanone 3-methyl-3-phenylhydrazone, 1-ethoxy-2-butanone 2-methyl-2-phenylhydrazone, 1-phenylacetone 2-(3-methoxyphenyl)-2-phenylhydrazone, 2-phenacetaldehyde 1-methyl-1-phenylhydrazone, methyl 3-[(Z)-2-methyl-2-phenylhydrazone]-butanethioate, 1-(3-chlorophenyl)-3-methoxy-1-propanone 1-methyl-1-(3-methylphenyl)hydrazone, Ferrocenephenylketone 2-[(E)-2-butenyl]-2-[(Z)-2-butenyl] hydrazone, Bis(cyclopentadienyl)Cobaltmethylketone 2,2-diphenylhydrazone, Bis(cyclopentadienyl) dimethyizirconiummethylketone 2,2-diphenyihydrazone, 1-phenyl-1-ethanone 1,1-di(2-methoxyethyl)hydrazone, 1-[3-(dimethylamino)phenyl]-1-ethanone 1,1-diethylhydrazone, 2-[(Z)-2,2-diethylhydrazono]propyl cyanide, 2-[(E)-2-ethyl-2-phenylhydrazono]-3-methoxypropyl cyanide, (Z)-1-chloro-1-penten-3-one 3-methyl-3-phenylhydrazone, and 2-propynal 1-[4-(dimethylamino)phenyl]-1-methylhydrazone.

2. The electrochromic device according to claim 1 wherein said first and second transparent substrates are made of glass.

3. The electrochromic device according to claim 1 wherein said seal is formed of epoxy.

4. The electrochromic device according to claim 1 wherein said transparent electrodes are made of indium tin oxide (ITO).

5. The electrochromic device according to claim 1 wherein said electrochromic composition further includes a compound selected from a group consisting of 1,1′

-bis(2-nitrophenyl)-4,4′

-dipyridinium bis(tetrafluoroborate), 1,1′

-bis(2-methoxyphenyl)-4,4′

-dipyridinium bis(tetrafluoroborate), and 1,1′

-bis(2-methylpheny)-4,4′

-dipyridinium bis(tetrafluoroborate).

6. The electrochromic device according to claim 1 wherein said electrochromic composition further includes a solvent selected from a group consisting of propylene carbonate, and ethyl methyl carbonate.

7. The electrochromic device according to claim 1 wherein said electrochromic composition further includes a polymeric electrolyte selected from a group consisting of polymethylmethacrylate (PMMA) and poly(ethylene) oxide (PEO).