Electrochromic polymeric solid films, manufacturing electrochromic devices using such solid films, and processes for making such solid films and devices

• US 20050079326A1
• Filed: 10/01/2004
• Published: 04/14/2005
• Est. Priority Date: 03/26/1997
• Status: Active Grant

• Current Assignee: Donnelly Corporation (Magna International Incorporated)
• Original Assignee: Donnelly Corporation (Magna International Incorporated)
• Inventors: Agrawal, Anoop, Dornan, Craig Allen, Allemand, Pierr-Marc, Varaprasad, Desaraju V., Lynam, Niall R., Zhao, Mingtao
• Granted Patent: US 7,202,987 B2
• Time in Patent Office: Days
• US Class Current: 428/193
• CPC Class Codes: B32B 17/06 comprising glass as the main or only constituent of a layer, next to another layer of a specific material
• CPC Class Codes: B32B 17/10036 comprising two outer glass sheets
• CPC Class Codes: B32B 17/10697 being cross-linked
• CPC Class Codes: B60Q 1/2665 on rear-view mirrors lighting devices for vehicle interior on or for rear-view mirrors B60Q3/258
• CPC Class Codes: B60Q 2900/40 Several lamps activated in sequence, e.g. sweep effect, progressive activation
• CPC Class Codes: B60R 1/088 using a cell of electrically changeable optical characteristic, e.g. liquid-crystal or electrochromic mirrors
• CPC Class Codes: B60R 1/1207 with lamps; with turn indicators
• CPC Class Codes: C09K 2211/1007 Non-condensed systems
• CPC Class Codes: C09K 2211/1011 Condensed systems
• CPC Class Codes: C09K 2211/1014 bridged by heteroatoms, e.g. N, P, Si or B
• CPC Class Codes: C09K 2211/1029 containing one nitrogen atom as the heteroatom
• CPC Class Codes: C09K 2211/1033 with oxygen
• CPC Class Codes: C09K 2211/1037 with sulfur
• CPC Class Codes: C09K 9/02 Organic tenebrescent materials
• CPC Class Codes: G02F 1/1503 caused by oxidation-reduction reactions in organic liquid solutions, e.g. viologen solutions
• CPC Class Codes: G02F 1/1516 comprising organic material
• CPC Class Codes: G02F 1/15165 Polymers
• CPC Class Codes: G02F 1/155 Electrodes
• CPC Class Codes: G02F 2001/1502 complementary cell
• CPC Class Codes: G02F 2001/15145 the electrochromic layer comprises a mixture of anodic and cathodic compounds
• CPC Class Codes: G02F 2001/1518 : Ferrocene compounds
• CPC Class Codes: G02F 2201/58 : Arrangements comprising a monitoring photodetector
• CPC Class Codes: G02F 2202/022 : polymeric
• CPC Class Codes: Y10T 428/24785 : including layer embodying mechanically interengaged strands, strand portions or strand-like strips [e.g., weave, knit, etc.]
• CPC Class Codes: Y10T 428/26 : Web or sheet containing structurally defined element or component, the element or component having a specified physical dimension
• CPC Class Codes: Y10T 428/31551 : Of polyamidoester [polyurethane, polyisocyanate, polycarbamate, etc.]
• CPC Class Codes: Y10T 428/31649 : Ester, halide or nitrile of addition polymer
• CPC Class Codes: Y10T 428/31678 : Of metal
• CPC Class Codes: Y10T 428/31935 : Ester, halide or nitrile of addition polymer
• CPC Class Codes: Y10T 83/0419 : By distorting within elastic limit

Abstract

An electrochromic mirror device suitable for use in a vehicle comprises a first transparent substrate having a transparent conductive layer on a surface thereof and a second substrate having a conductive layer on a surface thereof. The conductive layer of the first substrate opposes the second conductive layer of the second substrate in a spaced-apart relationship thereby forming an interpane distance between the substrates. A boundary seal is interposed between the first and second substrates spacing apart the substrates and forming a cavity wherein the interpane distance is at least about 10 microns. An electrochromic cross-linked polymeric solid film is disposed within the cavity. The electrochromic cross-linked solid polymeric film is formed from an electrochromic monomer composition that includes at least one cathodic electrochromic compound. The second conductive layer comprises a metallic reflective layer.

Claims

1-22. -22. (canceled)

23. An electrochromic mirror device suitable for use in a vehicle comprising:

a first transparent substrate having a transparent conductive layer on a surface thereof;

a second substrate having a conductive layer on a surface thereof, said conductive layer of said first substrate opposing said second conductive layer of said second substrate in a spaced-apart relationship thereby forming an interpane distance between said substrates;

a boundary seal interposed between said first and second substrates spacing apart said substrates and forming a cavity wherein said interpane distance is at least about 10 microns;

an electrochromic cross-linked polymeric solid film within said cavity, said electrochromic cross-linked solid polymeric film formed from an electrochromic monomer composition, said electrochromic monomer composition including at least one cathodic electrochromic compound; and

wherein said second conductive layer comprises a metallic reflective layer.

24. The electrochromic device according to claim 23, wherein said monomer composition includes at least one of (A) a monofunctional monomer and a cross-linking agent and (B) a polyfunctional monomer capable of cross-linking.

25. The electrochromic device according to claim 24, wherein said monomer composition includes (i) at least one anodic electrochromic compound and (ii) a plasticizer.

26. The electrochromic device according to claim 23, wherein the conductive layer of said first transparent substrate comprises a material selected from the group consisting of indium tin oxide, tin oxide, antimony-doped tin oxide, fluorine-doped tin oxide, antimony-doped zinc oxide and aluminum-doped zinc oxide.

27. The electrochromic device according to claim 23, wherein said metallic reflective layer comprises a material selected from the group consisting of aluminum, palladium, platinum, titanium, gold, chromium, silver and steel.

29. The electrochromic device according to claim 23, wherein said metallic reflective layer comprises a material selected from the group consisting of palladium, chromium and silver.

30. The electrochromic device according to claim 23, wherein said interpane distance is from about 10 microns to about 1000 microns.

31. The electrochromic device according to claim 30, wherein said interpane distance is from about 20 microns to about 200 microns.

32. The electrochromic device according to claim 31, wherein said interpane distance is from about 37 microns to about 74 microns.

33. The electrochromic device according to claim 23, wherein said boundary seal comprises a polymeric material.

34. The electrochromic device according to claim 33, wherein said polymeric material comprises at least one of an epoxy resin, a plasticized polyvinyl butyral, an ionomer resin, a polyamide material, a nitrile containing polymer and a butyl rubber.

35. The electrochromic device according to claim 33, wherein said boundary seal comprises spacers.

36. The electrochromic device according to claim 33, wherein said electrochromic monomer composition includes a monomer component selected from the group consisting of a urethane, a heterocyclic and an acrylate.

37. The electrochromic device according to claim 33, wherein said electrochromic monomer composition further comprises a component selected from the group consisting of a photoinitiator, a photosensitizer, an ultraviolet stabilizing agent, a coloring agent, a spacer, an anti-oxidizing agent, a flame retarding agent, a heat stabilizing agent, a compatibilizing agent, a humectant, a lubricating agent, an adhesion promoting agent, and a coupling agent.

38. The electrochromic device according to claim 33, wherein said electrochromic monomer composition comprises a cross-linking agent.

39. The electrochromic device according to claim 38, wherein said cross-linking agent is selected from the group consisting of a polyfunctional hydroxy compound, a polyfunctional primary or secondary amino compound, a polyfunctional mercapto compound and combinations thereof.

40. The electrochromic device according to claim 39, wherein said cross-linking agent comprises a polyfunctional hydroxy compound.

41. The electrochromic device according to claim 40, wherein said polyfunctional hydroxy compound comprises a polyol.

42. The electrochromic device according to claim 41, wherein said polyol comprises a glycol or a glycerol.

43. The electrochromic device according to claim 38, wherein said cross-linking agent is selected from the group consisting of pentaerythritol, 2-ethyl-2-(hydroxymethyl)-1,3-propanediol, caprolactone triols, and combinations thereof.

44. The electrochromic device according to claim 23, wherein said monomer composition comprises a monomer component which polymerizes by addition polymerization or ring opening polymerization selected from the group consisting of a monofunctional monomer, a difunctional monomer, a trifunctional monomer, a polyfunctional monomer or mixtures thereof.

45. The electrochromic device according to claim 44, wherein said monomer component is selected from the group of monomers consisting of 2-hydroxyethyl acrylate, 2-hydroxyethyl methacrylate, methylene glycol monoacrylate, diethylene glycol monomethacrylate, 2-hydroxypropyl acrylate, 2-hydroxypropyl methacrylate, 3-hydroxypropyl acrylate, 3-hydroxypropyl methacrylate, dipropylene glycol monomethacrylate, 2,3-dihydroxypropyl methacrylate, methyl acrylate, ethyl acrylate, n-propyl acrylate, i-propyl acrylate, n-butyl acrylate, s-butyl acrylate, n-pentyl acrylate, 2-ethylhexyl acrylate, methyl methacrylate, ethyl methacrylate, n-propyl methacrylate, i-propyl methacrylate, n-butyl methacrylate, s-butyl methacrylate, n-pentyl methacrylate, s-pentyl methacrylate, methoxyethyl acrylate, methoxyethyl methacrylate, triethylene glycol monoacrylate, glycerol monoacrylate, glycerol monomethacrylate, benzyl acrylate, caprolactone acrylate, cyclohexyl acrylate, cyclohexyl methacrylate, 2-ethoxyethyl acrylate, 2-ethoxyethyl methacrylate, 2-(2-ethoxyethoxy)-ethylacrylate, glycidyl methacrylate, n-hexyl acrylate, n-hexyl methacrylate, isobornyl acrylate, isobornyl methacrylate, i-decyl acrylate, i-decyl methacrylate, i-octyl acrylate, lauryl acrylate, lauryl methacrylate, 2-methoxyethyl acrylate, n-octyl acrylate, 2-phenoxyethyl acrylate, 2-phenoxyethyl methacrylate, stearyl acrylate, stearyl methacrylate, tetrahydrofurfuryl acrylate, tetrahydrofurfuryl methacrylate, tridecyl methacrylate, 1,4-butanediol diacrylate, 1,4-butanediol dimethacrylate, 1,3-butylene glycol diacrylate, 1,3-butylene glycol dimethacrylate, diethylene glycol diacrylate, diethylene glycol dimethacrylate, ethylene glycol diacrylate, ethoxylated bisphenol A dimethacrylate, ethylene glycol dimethacrylate, 1,6-hexanediol diacrylate, 1,6-hexanediol dimethacrylate, neopentyl glycol diacrylate, neopentyl glycol dimethacrylate, polyethylene glycol diacrylate, polyethylene glycol dimethacrylate, tetraethylene glycol diacrylate, tetraethylene glycol dimethacrylate, triethylene glycol diacrylate, triethylene glycol dimethacrylate, tripropylene glycol diacrylate, dipentaerythritol pentaacrylate, ethoxylated pentaerythritol triacrylate, pentaerythritol tetraacrylate, trimethylolpropane triacrylate, pentaerythritol triacrylate, trimethylolpropane trimethacrylate, tris(2-hydroxyethyl)-isocyanurate triacrylate, tris(2-hydroxyethyl)-isocyanurate trimethacrylate, polyethylene glycol monoacrylate, polyethylene glycol monomethacrylate, polypropylene glycol monoacrylate, polypropylene glycol monomethacrylate, hydroxyethyl cellulose acrylate, hydroxyethyl cellulose methacrylate, methoxy poly(ethyleneoxy) ethylacrylate, methoxy poly(ethyleneoxy) ethylmethacrylate, ethylene glycol diacrylate, ethylene glycol dimethacrylate, 1,2-butylene dimethacrylate, 1,3-butylene dimethacrylate, 1,4-butylene dimethacrylate, propylene glycol diacrylate, propylene glycol dimethacrylate, dipropylene glycol diacrylate, divinyl benzene, divinyl toluene, diallyl tartrate, allyl maleate, divinyl tartrate, triallyl melamine, glycerine trimethacrylate, diallyl maleate, divinyl ether, diallyl monomethylene glycol citrate, ethylene glycol vinyl allyl citrate, allyl vinyl maleate, diallyl itaconate, ethylene glycol diester of itaconic acid, polyester of maleic anhydride with triethylene glycol, polyallyl glucoses, polyallyl sucroses, glucose dimethacrylate, pentaerythritol tetraacrylate, sorbitol dimethacrylate, diallyl aconitate, divinyl citrasonate, diallyl fumarate, allyl methacrylate, 1,3-bis-(4-benzoyl-3-hydroxyphenoxy)-2-propylacrylate, 2-hydroxy-4-acryloxyethoxybenzophenone, 4-methacryloxy-2-hydroxybenzophenone, cyclohexene oxide, cyclopentene oxide, glycidyl i-propyl ether, glycidyl acrylate, furfuryl glycidyl ether, styrene oxide, ethyl-3-phenyl glycidate, 1,4-butanediol glycidyl ether, 2,3-epoxypropyl-4-(2,3-epoxypropoxy) benzoate, 4,4′

-bis-(2,3-epoxypropoxy)biphenyl and combinations thereof.

46. The electrochromic device according to claim 24, wherein said plasticizer is selected from the group consisting of acetonitrile, benzylacetone, 3-hydroxypropionitrile, methoxypropionitrile, 3-ethoxypropionitrile, propylene carbonate, ethylene carbonate, glycerine carbonate, 2-acetylbutyrolactone, cyanoethyl sucrose, 7-butyrolactone, 2-methylglutaronitrile, N,N′

-dimethylformamide, 3-methylsulfolane, methylethyl ketone, cyclopentanone, cyclohexanone, 4-hydroxy-4-methyl-2-pentanone, acetophenone, glutaronitrile, 3,3′

-oxydipropionitrile, 2-methoxyethyl ether, triethylene glycol dimethyl ether and combinations thereof.

47. The electrochromic device according to claim 23, wherein said cathodic electrochromic compound comprises a viologen or an anthraquinone.

48. The electrochromic device according to claim 44, wherein said cathodic electrochromic compound comprises a viologen.

49. The electrochromic device according to claim 24, wherein said anodic electrochromic compound is selected from the group consisting of a phenothiazine, a phenazine, and a metallocene.

50. The electrochromic device according to claim 49, wherein said anodic electrochromic compound is selected from the group consisting of 2-methyl-phenothiazine-3-one having been previously contacted with a redox agent, 5,10-dihydro-5,10-dimethylphenazine, and a ferrocene.

51. The electrochromic device according to claim 23, wherein said electrochromic cross-linked polymeric solid film comprises a cross-linked urethane, a cross-linked epoxy, a cross-linked acrylate, a cross-linked vinyl or a combination thereof.

52. The electrochromic device according to claim 23, wherein said electrochromic device comprises an interior automotive mirror device.

53. The electrochromic device according to claim 23, wherein said electrochromic device comprises an exterior automotive mirror device.

54. The electrochromic device according to claim 23, wherein said electrochromic cross-linked polymeric solid film is formed within said cavity.

55. The electrochromic device according to claim 54, wherein said electrochromic cross-linked polymeric solid film is formed within said cavity by introducing said electrochromic monomer composition into said cavity and by a polymerization of components of said electrochromic monomer composition in said cavity.

56. The electrochromic device according to claim 55, wherein said electrochromic monomer composition is introduced into said cavity by vacuum backfilling.

57. An electrochromic mirror device suitable for use in a vehicle comprising:

a first transparent substrate having a transparent conductive layer on a surface thereof;

a second substrate having a conductive layer on a surface thereof, said conductive layer of said first substrate opposing said second conductive layer of said second substrate in a spaced-apart relationship thereby forming an interpane distance between said substrates;

a boundary seal interposed between said first and second substrates spacing apart said substrates and forming a cavity wherein said interpane distance is at least about 10 microns;

an electrochromic cross-linked polymeric solid film within said cavity, said electrochromic cross-linked solid polymeric film formed from an electrochromic monomer composition, said electrochromic monomer composition including at least one cathodic electrochromic compound; and

wherein said electrochromic cross-linked polymeric solid film is formed within said cavity by a polymerization of components of said electrochromic monomer composition after introduction by vacuum backfilling of said electrochromic monomer composition into said cavity.

58. The electrochromic device according to claim 57, wherein said monomer composition includes at least one of (A) a monofunctional monomer and a cross-linking agent and (B) a polyfunctional monomer capable of cross-linking.

59. The electrochromic device according to claim 58, wherein said monomer composition includes (i) at least one anodic electrochromic compound and (ii) a plasticizer.

60. The electrochromic device according to claim 57, wherein the conductive layer of said first transparent substrate comprises a material selected from the group consisting of indium tin oxide, tin oxide, antimony-doped tin oxide, fluorine-doped tin oxide, antimony-doped zinc oxide and aluminum-doped zinc oxide.

61. The electrochromic device according to claim 57, wherein said second conductive layer comprises a metallic reflective layer.

62. The electrochromic device according to claim 61, wherein said metallic reflective layer comprises a material selected from the group consisting of aluminum, palladium, platinum, titanium, gold, chromium, silver and steel.

63. The electrochromic device according to claim 61, wherein said metallic reflective layer comprises a material selected from the group consisting of palladium, chromium and silver.

64. The electrochromic device according to claim 57, wherein said interpane distance is from about 10 microns to about 1000 microns.

65. The electrochromic device according to claim 64, wherein said interpane distance is from about 20 microns to about 200 microns.

66. The electrochromic device according to claim 65, wherein said interpane distance is from about 37 microns to about 74 microns.

67. The electrochromic device according to claims 57, wherein said boundary seal comprises a polymeric material.

68. The electrochromic device according to claims 67, wherein said polymeric material comprises at least one of an epoxy resin, a plasticized polyvinyl butyral, an ionomer resin, a polyamide material, a nitrile containing polymer and a butyl rubber.

69. The electrochromic device according to claims 67, wherein said boundary seal comprises spacers.

70. The electrochromic device according to claim 57, wherein said electrochromic monomer composition includes a monomer component selected from the group consisting of a urethane, a heterocyclic and an acrylate.

71. The electrochromic device according to claim 57, wherein said electrochromic monomer composition further comprises a component selected from the group consisting of a photoinitiator, a photosensitizer, an ultraviolet stabilizing agent, a coloring agent, a spacer, an anti-oxidizing agent, a flame retarding agent, a heat stabilizing agent, a compatibilizing agent, a humectant, a lubricating agent, an adhesion promoting agent, and a coupling agent.

72. The electrochromic device according to claim 57, wherein said electrochromic monomer composition comprises a cross-linking agent.

73. The electrochromic device according to claim 72, wherein said cross-linking agent is selected from the group consisting of a polyfunctional hydroxy compound, a polyfunctional primary or secondary amino compound, a polyfunctional mercapto compound and combinations thereof.

74. The electrochromic device according to claim 73, wherein said cross-linking agent comprises a polyfunctional hydroxy compound.

75. The electrochromic device according to claim 74, wherein said polyfunctional hydroxy compound comprises a polyol.

76. The electrochromic device according to claim 75, wherein said polyol comprises a glycol or a glycerol.

77. The electrochromic device according to claim 72, wherein said cross-linking agent is selected from the group consisting of pentaerythritol, 2-ethyl-2-(hydroxymethyl)-1,3-propanediol, caprolactone triols, and combinations thereof.

78. The electrochromic device according to claim 57, wherein said monomer composition comprises a monomer component which polymerizes by addition polymerization or ring opening polymerization selected from the group consisting of a monofunctional monomer, a difunctional monomer, a trifunctional monomer, a polyfunctional monomer or mixtures thereof.

79. The electrochromic device according to claim 78, wherein said monomer component is selected from the group of monomers consisting of 2-hydroxyethyl acrylate, 2-hydroxyethyl methacrylate, methylene glycol monoacrylate, diethylene glycol monomethacrylate, 2-hydroxypropyl acrylate, 2-hydroxypropyl methacrylate, 3-hydroxypropyl acrylate, 3-hydroxypropyl methacrylate, dipropylene glycol monomethacrylate, 2,3-dihydroxypropyl methacrylate, methyl acrylate, ethyl acrylate, n-propyl acrylate, i-propyl acrylate, n-butyl acrylate, s-butyl acrylate, n-pentyl acrylate, 2-ethylhexyl acrylate, methyl methacrylate, ethyl methacrylate, n-propyl methacrylate, i-propyl methacrylate, n-butyl methacrylate, s-butyl methacrylate, n-pentyl methacrylate, s-pentyl methacrylate, methoxyethyl acrylate, methoxyethyl methacrylate, triethylene glycol monoacrylate, glycerol monoacrylate, glycerol monomethacrylate, benzyl acrylate, caprolactone acrylate, cyclohexyl acrylate, cyclohexyl methacrylate, 2-ethoxyethyl acrylate, 2-ethoxyethyl methacrylate, 2-(2-ethoxyethoxy)-ethylacrylate, glycidyl methacrylate, n-hexyl acrylate, n-hexyl methacrylate, isobornyl acrylate, isobornyl methacrylate, i-decyl acrylate, i-decyl methacrylate, i-octyl acrylate, lauryl acrylate, lauryl methacrylate, 2-methoxyethyl acrylate, n-octyl acrylate, 2-phenoxyethyl acrylate, 2-phenoxyethyl methacrylate, stearyl acrylate, stearyl methacrylate, tetrahydrofurfuryl acrylate, tetrahydrofurfuryl methacrylate, tridecyl methacrylate, 1,4-butanediol diacrylate, 1,4-butanediol dimethacrylate, 1,3-butylene glycol diacrylate, 1,3-butylene glycol dimethacrylate, diethylene glycol diacrylate, diethylene glycol dimethacrylate, ethylene glycol diacrylate, ethoxylated bisphenol A dimethacrylate, ethylene glycol dimethacrylate, 1,6-hexanediol diacrylate, 1,6-hexanediol dimethacrylate, neopentyl glycol diacrylate, neopentyl glycol dimethacrylate, polyethylene glycol diacrylate, polyethylene glycol dimethacrylate, tetraethylene glycol diacrylate, tetraethylene glycol dimethacrylate, triethylene glycol diacrylate, triethylene glycol dimethacrylate, tripropylene glycol diacrylate, dipentaerythritol pentaacrylate, ethoxylated pentaerythritol triacrylate, pentaerythritol tetraacrylate, trimethylolpropane triacrylate, pentaerythritol triacrylate, trimethylolpropane trimethacrylate, tris(2-hydroxyethyl)-isocyanurate triacrylate, tris(2-hydroxyethyl)-isocyanurate trimethacrylate, polyethylene glycol monoacrylate, polyethylene glycol monomethacrylate, polypropylene glycol monoacrylate, polypropylene glycol monomethacrylate, hydroxyethyl cellulose acrylate, hydroxyethyl cellulose methacrylate, methoxy poly(ethyleneoxy) ethylacrylate, methoxy poly(ethyleneoxy) ethylmethacrylate, ethylene glycol diacrylate, ethylene glycol dimethacrylate, 1,2-butylene dimethacrylate, 1,3-butylene dimethacrylate, 1,4-butylene dimethacrylate, propylene glycol diacrylate, propylene glycol dimethacrylate, dipropylene glycol diacrylate, divinyl benzene, divinyl toluene, diallyl tartrate, allyl maleate, divinyl tartrate, triallyl melamine, glycerine trimethacrylate, diallyl maleate, divinyl ether, diallyl monomethylene glycol citrate, ethylene glycol vinyl allyl citrate, allyl vinyl maleate, diallyl itaconate, ethylene glycol diester of itaconic acid, polyester of maleic anhydride with triethylene glycol, polyallyl glucoses, polyallyl sucroses, glucose dimethacrylate, pentaerythritol tetraacrylate, sorbitol dimethacrylate, diallyl aconitate, divinyl citrasonate, diallyl fumarate, allyl methacrylate, 1,3-bis-(4-benzoyl-3-hydroxyphenoxy)-2-propylacrylate, 2-hydroxy-4-acryloxyethoxybenzophenone, 4-methacryloxy-2-hydroxybenzophenone, cyclohexene oxide, cyclopentene oxide, glycidyl i-propyl ether, glycidyl acrylate, furfuryl glycidyl ether, styrene oxide, ethyl-3-phenyl glycidate, 1,4-butanediol glycidyl ether, 2,3-epoxypropyl-4-(2,3-epoxypropoxy) benzoate, 4,4′

-bis-(2,3-epoxypropoxy)biphenyl and combinations thereof.

80. The electrochromic device according to claim 58, wherein said plasticizer is selected from the group consisting of acetonitrile, benzylacetone, 3-hydroxypropionitrile, methoxypropionitrile, 3-ethoxypropionitrile, propylene carbonate, ethylene carbonate, glycerine carbonate, 2-acetylbutyrolactone, cyanoethyl sucrose, 7-butyrolactone, 2-methylglutaronitrile, N,N′

-dimethylformamide, 3-methylsulfolane, methylethyl ketone, cyclopentanone, cyclohexanone, 4-hydroxy-4-methyl-2-pentanone, acetophenone, glutaronitrile, 3,3′

-oxydipropionitrile, 2-methoxyethyl ether, triethylene glycol dimethyl ether and combinations thereof.

81. The electrochromic device according to claim 57, wherein said cathodic electrochromic compound comprises a viologen or an anthraquinone.

82. The electrochromic device according to claim 78, wherein said cathodic electrochromic compound comprises a viologen.

83. The electrochromic device according to claim 58, wherein said anodic electrochromic compound is selected from the group consisting of a phenothiazine, a phenazine, and a metallocene.

84. The electrochromic device according to claim 83, wherein said anodic electrochromic compound is selected from the group consisting of 2-methyl-phenothiazine-3-one having been previously contacted with a redox agent, 5,10-dihydro-5,10-dimethylphenazine, and a ferrocene.

85. The electrochromic device according to claim 57, wherein said electrochromic cross-linked polymeric solid film comprises a cross-linked urethane, a cross-linked epoxy, a cross-linked acrylate, a cross-linked vinyl or a combination thereof.

86. The electrochromic device according to claim 57, wherein said electrochromic device comprises an interior automotive mirror device.

87. The electrochromic device according to claim 57, wherein said electrochromic device comprises an exterior automotive mirror device.

88. An electrochromic mirror device suitable for use in a vehicle comprising:

a first transparent substrate having a transparent conductive layer on a surface thereof;

a second substrate having a conductive layer on a surface thereof, said conductive layer of said first substrate opposing said second conductive layer of said second substrate in a spaced-apart relationship thereby forming an interpane distance between said substrates;

a boundary seal interposed between said first and second substrates spacing apart said substrates and forming a cavity;

an electrochromic cross-linked polymeric solid film within said cavity, said electrochromic cross-linked solid polymeric film formed from an electrochromic monomer composition, said electrochromic monomer composition including at least one cathodic electrochromic compound; and

wherein said electrochromic cross-linked polymeric solid film is formed within said cavity by a polymerization of components of said electrochromic monomer composition after introduction of said electrochromic monomer composition into said cavity; and

wherein said interpane distance is from about 20 microns to about 200 microns.

89. The electrochromic device according to claim 88, wherein said monomer composition includes at least one of (A) a monofunctional monomer and a cross-linking agent and (B) a polyfunctional monomer capable of cross-linking.

90. The electrochromic device according to claim 89, wherein said monomer composition includes (i) at least one anodic electrochromic compound and (ii) a plasticizer.

91. The electrochromic device according to claim 88, wherein the conductive layer of said first transparent substrate comprises a material selected from the group consisting of indium tin oxide, tin oxide, antimony-doped tin oxide, fluorine-doped tin oxide, antimony-doped zinc oxide and aluminum-doped zinc oxide.

92. The electrochromic device according to claim 88, wherein said second conductive layer comprises a metallic reflective layer.

93. The electrochromic device according to claim 92, wherein said metallic reflective layer comprises a material selected from the group consisting of aluminum, palladium, platinum, titanium, gold, chromium, silver and steel.

94. The electrochromic device according to claim 92, wherein said metallic reflective layer comprises a material selected from the group consisting of palladium, chromium and silver.

95. The electrochromic device according to claim 88, wherein said introduction of said electrochromic monomer composition into said cavity is by vacuum backfilling.

96. The electrochromic device according to claim 88, wherein said second conductive layer comprises a metallic reflective layer and wherein said introduction of said electrochromic monomer composition into said cavity is by vacuum backfilling.

97. The electrochromic device according to claim 96, wherein said interpane distance is from about 37 microns to about 74 microns.

98. The electrochromic device according to claims 88, wherein said boundary seal comprises a polymeric material.

99. The electrochromic device according to claims 98, wherein said polymeric material comprises at least one of an epoxy resin, a plasticized polyvinyl butyral, an ionomer resin, a polyamide material, a nitrile containing polymer and a butyl rubber.

100. The electrochromic device according to claims 98, wherein said boundary seal comprises spacers.

101. The electrochromic device according to claim 88, wherein said electrochromic monomer composition includes a monomer component selected from the group consisting of a urethane, a heterocyclic and an acrylate.

102. The electrochromic device according to claim 88, wherein said electrochromic monomer composition further comprises a component selected from the group consisting of a photoinitiator, a photosensitizer, an ultraviolet stabilizing agent, a coloring agent, a spacer, an anti-oxidizing agent, a flame retarding agent, a heat stabilizing agent, a compatibilizing agent, a humectant, a lubricating agent, a adhesion promoting agent, and a coupling agent.

103. The electrochromic device according to claim 88, wherein said electrochromic monomer composition comprises a cross-linking agent.

104. The electrochromic device according to claim 103, wherein said cross-linking agent is selected from the group consisting of a polyfunctional hydroxy compound, a polyfunctional primary or secondary amino compound, a polyfunctional mercapto compound and combinations thereof.

105. The electrochromic device according to claim 104, wherein said cross-linking agent comprises a polyfunctional hydroxy compound.

106. The electrochromic device according to claim 105, wherein said polyfunctional hydroxy compound comprises a polyol.

107. The electrochromic device according to claim 106, wherein said polyol comprises a glycol or a glycerol.

108. The electrochromic device according to claim 103, wherein said cross-linking agent is selected from the group consisting of pentaerythritol, 2-ethyl-2-(hydroxymethyl)-1,3-propanediol, caprolactone triols, and combinations thereof.

109. The electrochromic device according to claim 88, wherein said monomer composition comprises a monomer component which polymerizes by addition polymerization or ring opening polymerization selected from the group consisting of a monofunctional monomer, a difunctional monomer, a trifunctional monomer, a polyfunctional monomer or mixtures thereof.

110. The electrochromic device according to claim 109, wherein said monomer component is selected from the group of monomers consisting of 2-hydroxyethyl acrylate, 2-hydroxyethyl methacrylate, methylene glycol monoacrylate, diethylene glycol monomethacrylate, 2-hydroxypropyl acrylate, 2-hydroxypropyl methacrylate, 3-hydroxypropyl acrylate, 3-hydroxypropyl methacrylate, dipropylene glycol monomethacrylate, 2,3-dihydroxypropyl methacrylate, methyl acrylate, ethyl acrylate, n-propyl acrylate, i-propyl acrylate, n-butyl acrylate, s-butyl acrylate, n-pentyl acrylate, 2-ethylhexyl acrylate, methyl methacrylate, ethyl methacrylate, n-propyl methacrylate, i-propyl methacrylate, n-butyl methacrylate, s-butyl methacrylate, n-pentyl methacrylate, s-pentyl methacrylate, methoxyethyl acrylate, methoxyethyl methacrylate, triethylene glycol monoacrylate, glycerol monoacrylate, glycerol monomethacrylate, benzyl acrylate, caprolactone acrylate, cyclohexyl acrylate, cyclohexyl methacrylate, 2-ethoxyethyl acrylate, 2-ethoxyethyl methacrylate, 2-(2-ethoxyethoxy)-ethylacrylate, glycidyl methacrylate, n-hexyl acrylate, n-hexyl methacrylate, isobornyl acrylate, isobornyl methacrylate, i-decyl acrylate, i-decyl methacrylate, i-octyl acrylate, lauryl acrylate, lauryl methacrylate, 2-methoxyethyl acrylate, n-octyl acrylate, 2-phenoxyethyl acrylate, 2-phenoxyethyl methacrylate, stearyl acrylate, stearyl methacrylate, tetrahydrofurfuryl acrylate, tetrahydrofurfuryl methacrylate, tridecyl methacrylate, 1,4 -butanediol diacrylate, 1,4-butanediol dimethacrylate, 1,3-butylene glycol diacrylate, 1,3-butylene glycol dimethacrylate, diethylene glycol diacrylate, diethylene glycol dimethacrylate, ethylene glycol diacrylate, ethoxylated bisphenol A dimethacrylate, ethylene glycol dimethacrylate, 1,6-hexanediol diacrylate, 1,6-hexanediol dimethacrylate, neopentyl glycol diacrylate, neopentyl glycol dimethacrylate, polyethylene glycol diacrylate, polyethylene glycol dimethacrylate, tetraethylene glycol diacrylate, tetraethylene glycol dimethacrylate, triethylene glycol diacrylate, triethylene glycol dimethacrylate, tripropylene glycol diacrylate, dipentaerythritol pentaacrylate, ethoxylated pentaerythritol triacrylate, pentaerythritol tetraacrylate, trimethylolpropane triacrylate, pentaerythritol triacrylate, trimethylolpropane trimethacrylate, tris(2-hydroxyethyl)-isocyanurate triacrylate, tris(2-hydroxyethyl)-isocyanurate trimethacrylate, polyethylene glycol monoacrylate, polyethylene glycol monomethacrylate, polypropylene glycol monoacrylate, polypropylene glycol monomethacrylate, hydroxyethyl cellulose acrylate, hydroxyethyl cellulose methacrylate, methoxy poly(ethyleneoxy) ethylacrylate, methoxy poly(ethyleneoxy) ethylmethacrylate, ethylene glycol diacrylate, ethylene glycol dimethacrylate, 1,2-butylene dimethacrylate, 1,3-butylene dimethacrylate, 1,4-butylene dimethacrylate, propylene glycol diacrylate, propylene glycol dimethacrylate, dipropylene glycol diacrylate, divinyl benzene, divinyl toluene, diallyl tartrate, allyl maleate, divinyl tartrate, triallyl melamine, glycerine trimethacrylate, diallyl maleate, divinyl ether, diallyl monomethylene glycol citrate, ethylene glycol vinyl allyl citrate, allyl vinyl maleate, diallyl itaconate, ethylene glycol diester of itaconic acid, polyester of maleic anhydride with triethylene glycol, polyallyl glucoses, polyallyl sucroses, glucose dimethacrylate, pentaerythritol tetraacrylate, sorbitol dimethacrylate, diallyl aconitate, divinyl citrasonate, diallyl fumarate, allyl methacrylate, 1,3-bis-(4-benzoyl-3-hydroxyphenoxy)-2-propylacrylate, 2-hydroxy-4-acryloxyethoxybenzophenone, 4 -methacryloxy-2-hydroxybenzophenone, cyclohexene oxide, cyclopentene oxide, glycidyl i-propyl ether, glycidyl acrylate, furfuryl glycidyl ether, styrene oxide, ethyl-3-phenyl glycidate, 1,4-butanediol glycidyl ether, 2,3-epoxypropyl-4-(2,3-epoxypropoxy) benzoate, 4,4′

-bis-(2,3-epoxypropoxy)biphenyl and combinations thereof.

111. The electrochromic device according to claim 89, wherein said plasticizer is selected from the group consisting of acetonitrile, benzylacetone, 3-hydroxypropionitrile, methoxypropionitrile, 3-ethoxypropionitrile, propylene carbonate, ethylene carbonate, glycerine carbonate, 2-acetylbutyrolactone, cyanoethyl sucrose, 7-butyrolactone, 2-methylglutaronitrile, N,N′

-dimethylformamide, 3-methylsulfolane, methylethyl ketone, cyclopentanone, cyclohexanone, 4-hydroxy-4-methyl-2-pentanone, acetophenone, glutaronitrile, 3,3′

-oxydipropionitrile, 2-methoxyethyl ether, triethylene glycol dimethyl ether and combinations thereof.

112. The electrochromic device according to claim 88, wherein said cathodic electrochromic compound comprises a viologen or an anthraquinone.

113. The electrochromic device according to claim 109, wherein said cathodic electrochromic compound comprises a viologen.

114. The electrochromic device according to claim 89, wherein said anodic electrochromic compound is selected from the group consisting of a phenothiazine, a phenazine, and a metallocene.

115. The electrochromic device according to claim 114, wherein said anodic electrochromic compound is selected from the group consisting of 2-methyl-phenothiazine-3-one having been previously contacted with a redox agent, 5,10-dihydro-5, 10-dimethylphenazine, and a ferrocene.

116. The electrochromic device according to claim 88, wherein said electrochromic cross-linked polymeric solid film comprises a cross-linked urethane, a cross-linked epoxy, a cross-linked acrylate, a cross-linked vinyl or a combination thereof.

117. The electrochromic device according to claim 88, wherein said electrochromic device comprises an interior automotive mirror device.

118. The electrochromic device according to claim 88, wherein said electrochromic device comprises an exterior automotive mirror device.