Electrochromic solution containing hydrazone compound and device manufactured with same

• US 20030173552A1
• Filed: 03/12/2003
• Published: 09/18/2003
• Est. Priority Date: 09/04/2001
• Status: Abandoned Application

• Current Assignee: Fu-Shing Wang, Kuang-Mei Hsu
• Original Assignee: Fu-Shing Wang, Kuang-Mei Hsu
• Inventors: Hsu, Kuang-Mei, Wang, Fu-Shing
• Application Number:
  US10/387,025
• Publication Number:
  US 20030173552A1
• Time in Patent Office: Days
• US Class Current: 252/586
• 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 carbon 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 solution for use in an electrochromic unit for performing color change in response to a voltage applied to said electrochromic unit, comprising:

at least one anodic compound including a hydrazone compound represented by the formula below;

at least one cathodic compound; and

at least one solvent;

wherein said hydrazone compound is a member selected from a group consisting of Acetone 2,2-dimethylhydrazone, 2-pentanone 2-ethyl-2-methylhydrazone, 2-ethylbutanal 1-ethyl-1-propylhydrazone, 2-ethyl-2-nonanone 2-hexyl-2-propylhydrazone, (E)-3-nonen-2-one 2-butyl-2-propylhydrazone, 2-hexanone 2-[(E)-2-butenyl]-2-[(Z)-2-butenyl]hydrazone, 4-pentyn-2-one 2,2-dipropylhydrazone, 1-penten-3-one 3,3-dimethyihydrazone, 2-hexanone 2,2-diphenylhydrazone, 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)dimethylzirconiummethylketone 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 or a member selected from a group consisting of compounds represented by the following formulae, respectively;

2. The electrochromic solution according to claim 1 wherein said at least one cathodic compound includes a compound represented by the following formula:

3. The electrochromic solution according to claim 2 wherein said at least one cathodic compound includes a compound represented by the following formula:

4. The electrochromic solution according to claim 1 wherein said at least one solvent includes a solvent selected from a group consisting of acetonitrile, N,N-dimethylformamide, propylene carbonate, methyl ethyl carbonate, 3-hydroxypropionitrile, ethylene carbonate.

5. The electrochromic solution according to claim 1 wherein said at least one solvent includes a solvent selected from propylene carbonate, ethyl methyl carbonate.

6. The electrochromic solution according to claim 1 further comprising an electrolyte material.

7. The electrochromic solution according to claim 6 wherein said electrolyte material is a member selected from a group consisting of Nafion, poly(2-acrylamide-2-methyl propane sulfonic acid) (PAMAS), poly(vinylalcohol phosphoric acid) (PAVA), poly(ethylene) oxide (PEO), poly(ethylene)imine (PEI), tetra-n-butylammonium fluorborate, polymethylmethacrylate (PMMA).

8. The electrochromic solution according to claim 6 wherein said electrolyte material is a polymeric electrolyte.

9. The electrochromic solution according to claim 8 wherein said polymeric electrolyte is a member selected from a group consisting of polymethylmethacrylate (PMMA) and poly(ethylene) oxide (PEO).

10. An electrochromic solution for use in an electrochromic unit for performing color change in response to a voltage applied to said electrochromic unit, comprising:

at least one anodic compound including a hydrazone compound represented by the formula below;

where

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 carbon 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;

at least one cathodic compound including a compound represented by the following formula;

and

at least one solvent.

11. The electrochromic solution according to claim 10 wherein said hydrazone compound is a member selected from a group consisting of Acetone 2,2-dimethylhydrazone, 2-pentanone 2-ethyl-2-methylhydrazone, 2-ethylbutanal 1-ethyl-1-propylhydrazone, 2-ethyl-2-nonanone 2-hexyl-2-propylhydrazone, (E)-3-nonen-2-one 2-butyl-2-propylhydrazone, 2-hexanone 2-[(E)-2-butenyl]-2-[(Z)-2-butenyl]hydrazone, 4-pentyn-2-one 2,2-dipropylhydrazone, 1-penten-3-one 3,3-dimethyihydrazone, 2-hexanone 2,2-diphenylhydrazone, 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-l-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)dimethylzirconiummethylketone 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.

12. The electrochromic solution according to claim 10 wherein said hydrazone compound is a member selected from a group consisting of compounds represented by the following formulae, respectively:

13. The electrochromic solution according to claim 10 wherein said at least one solvent includes a solvent selected from a group consisting of acetonitrile, N,N-dimethylformamide, propylene carbonate, methyl ethyl carbonate, 3-hydroxypropionitrile, ethylene carbonate.

14. The electrochromic solution according to claim 10 further comprising an electrolyte material, which is a member selected from a group consisting of Nafion, poly(2-acrylamide-2-methyl propane sulfonic acid) (PAMAS), poly(vinylalcohol phosphoric acid) (PAVA), poly(ethylene) oxide (PEO), poly(ethylene)imine (PEI), tetra-n-butylammonium fluorborate, polymethylmethacrylate (PMMA).

15. An electrochromic solution for use in an electrochromic unit for performing color change in response to a voltage applied to said electrochromic unit, comprising:

at least one anodic compound including a hydrazone compound represented by the formula below;

at least one cathodic compound; and

at least one solvent;

wherein said hydrazone compound is a member selected from a group consisting of Acetone 2,2-dimethylhydrazone, 2-pentanone 2-ethyl-2-methylhydrazone, 2-ethylbutanal 1-ethyl-1-propylhydrazone, 2-ethyl-2-nonanone 2-hexyl-2-propylhydrazone, (E)-3-nonen-2-one 2-butyl-2-propylhydrazone, 2-hexanone 2-[(E)-2-butenyl]-2-[(Z)-2-butenyl]hydrazone, 4-pentyn-2-one 2,2-dipropylhydrazone, 1-penten-3-one 3,3-dimethyihydrazone, 2-hexanone 2,2-diphenylhydrazone, 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)dimethylzirconiummethylketone 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, or a member selected from a group consisting of compounds represented by the following formulae, respectively;

and

wherein said at least one cathodic compound includes a compound represented by the following formula;

where

R5 and R6 are individually selected from a group consisting of alkyl containing 1 to 10 carbon atoms and aryl containing 5 to 20 carbon atoms which is unsubstituted or optionally substituted with alkyl, alkoxy, cyano, Cl, Br, I and nitro; and

X₁⁻

and X₂⁻

are individually selected from a group consisting of Cl⁻

, Br⁻

, I⁻

, BF₄⁻

, PF₆⁻

, AsF₆⁻

, ClO₄⁻

and NO₃⁻

.

16. The electrochromic solution according to claim 15 wherein said at least one cathodic compound includes a compound represented by the following formula:

17. The electrochromic solution according to claim 15 wherein said at least one solvent includes a solvent selected from a group consisting of acetonitrile, N,N-dimethylformamide, propylene carbonate, methyl ethyl carbonate, 3-hydroxypropionitrile, ethylene carbonate.

18. The electrochromic solution according to claim 15 wherein said at least one solvent includes a solvent selected from propylene carbonate, ethyl methyl carbonate.

19. The electrochromic solution according to claim 15 further comprising an electrolyte material.

20. The electrochromic solution according to claim 19 wherein said electrolyte material is a member selected from a group consisting of Nafion, poly(2-acrylamide-2-methyl propane sulfonic acid) (PAMAS), poly(vinylalcohol phosphoric acid) (PAVA), poly(ethylene) oxide (PEO), poly(ethylene)imine (PEI), tetra-n-butylammonium fluorborate, polymethylmethacrylate (PMMA).