Electrochromic solution containing hydrazone compound and device manufactured with same

Abstract

An electrochromic solution includes a hydrazone compound as an anodic compound is disclosed. The hydrazone compound has a general formula (I) wherein R 1 , R 2 , R 3 and R 4 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.

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:  
       
         
           
           
               
               
           
         
       
       wherein 
 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  
 X 1   −  and X 2   −  are individually selected from a group consisting of Cl − , Br − , I − , BF 4   − , PF 6   − , AsF 6   − , ClO 4   −  and NO 3   − .  
 
     
     
         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    R 1 , R 2 , R 3  and R 4  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    X 1   −  and X 2   −  are individually selected from a group consisting of Cl − , Br − , I − , BF 4   − , PF 6   − , AsF 6   − , ClO 4   −  and NO 3   − .    
     
     
         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).