Novel electrochromic materials and devices
First Claim
1. An electrochromic material comprising a substituted-1,1-dioxo-thiopyran of the general structure I:
- wherein;
X is carbon, nitrogen, oxygen, or sulfur;
n is 0, 1 or 2;
R3 is independently an electron withdrawing group or a substituted or unsubstituted alky or aryl group;
R1 and R5 each independently represent a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group; and
R2 and R4 each independently represent hydrogen, or an electron withdrawing group, or a substituted or unsubstituted alkyl group.
9 Assignments
0 Petitions
Accused Products
Abstract
The present invention relates to an electrochromic material, and a device utilizing the electrochromic material, comprising a substituted-1,1-dioxo-thiopyran of the general structure I:
-
Citations
137 Claims
-
1. An electrochromic material comprising a substituted-1,1-dioxo-thiopyran of the general structure I:
-
wherein;
X is carbon, nitrogen, oxygen, or sulfur;
n is 0, 1 or 2;
R3 is independently an electron withdrawing group or a substituted or unsubstituted alky or aryl group;
R1 and R5 each independently represent a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group; and
R2 and R4 each independently represent hydrogen, or an electron withdrawing group, or a substituted or unsubstituted alkyl group. - View Dependent Claims (2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29, 30, 31, 32, 33, 34, 35, 36)
-
-
15. The electrochromic material of claim 9 wherein said electrochromic material is represented by the following structure:
-
16. The electrochromic material of claim 9 wherein said electrochromic material is represented by the following structure:
-
17. The electrochromic material of claim 9 that incorporate that incorporate functional groups that facilitate the irreversible chemisorption nanocrystalline metal oxide electrodes.
-
18. The electrochromic material of claim 9 wherein R1 thru R5 together or separately comprise carboxylate, salicylate, or phosphonate groups that facilitate irreversible chemisorption towards metal oxide electrodes.
-
19. The electrochromic material of claim 9 wherein the electrochromic material is represented by the following structure:
-
20. The electrochromic material of claim 9 wherein the electrochromic material is represented by the following structure:
-
21. The electrochromic material of claim 9 wherein the electrochromic material is represented by the following structure:
-
22. The electrochromic material of claim 9 wherein said electrochromic material is represented by the formula:
-
23. The electrochromic material of claim 9 wherein said electrochromic material is represented by the formula:
-
24. The electrochromic material of claim 9 wherein said electrochromic material is represented by the formula:
-
25. The electrochromic material of claim 1 wherein X represents nitrogen and n is 1.
-
26. The electrochromic material of claim 25 wherein said electrochromic material is at least one member selected from the group consisting of:
-
27. The electrochromic material of claim 1 wherein X is oxygen or sulfur, and the value of n is 0.
-
28. The electrochromic material of claim 1 wherein said electrochromic material has an electrochemical reduction potential of from −
- 1.0 to +0.2 Volts vs SCE.
-
29. The electrochromic material of claim 1 wherein said electrochromic material has an electrochemical reduction potential of from −
- 0.8 to −
0.1 Volts vs SCE.
- 0.8 to −
-
30. The electrochromic material of claim 1 wherein said electrochromic material has an electrochemical reduction potential of from −
- 0.6 to −
0.2 Volts vs SCE.
- 0.6 to −
-
31. The electrochromic material of claim 1 wherein said electrochromic material comprises electrochromic sulfone structures that have groups for linking to nanocrystalline TiO2 or SnO2.
-
32. The electrochromic material of claim 1 wherein said electrochromic material is capable of color change upon reduction.
-
33. The electrochromic material of claim 32 wherein said color change upon reduction is reversible.
-
34. The electrochromic material of claim 1 wherein said electrochromic material is stable in the reduced and unreduced states.
-
35. The electrochromic material of claim 1 wherein said electrochromic material is colorless and upon reduction is colored.
-
36. The electrochromic material of claim 1 which upon reduction exhibits optical absorption between 390 and 750 nm with an extinction coefficient between 5000 M−
- 1 cm−
1 and 25,000 M−
1 cm−
1.
- 1 cm−
-
37. An electrochromic device comprising a substrate, at least two electrodes, an electrolyte positioned between said electrodes, an electron donor, and an electrochromic material comprising a substituted-1,1-dioxo-thiopyran of the general structure I:
-
wherein;
X is carbon, nitrogen, oxygen, or sulfur;
n is 0, 1 or 2;
R3 is independently an electron withdrawing group or a substituted or unsubstituted alky or aryl group;
R1 and R5 each independently represent a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group; and
R2 and R4 each independently represent hydrogen, or an electron withdrawing group, or a substituted or unsubstituted alkyl group. - View Dependent Claims (38, 39, 40, 41, 42, 43, 44, 45, 46, 47, 48, 49, 50, 51, 52, 53, 54, 55, 56, 57, 58, 59, 60, 61, 62, 63, 64, 65, 66, 67, 68, 69, 70, 71, 72, 73, 74, 75, 76, 77, 78, 79, 80, 81, 82, 83, 84, 85, 86, 87, 88, 89, 90, 91, 92, 93, 94, 95, 96, 97, 98, 99, 100, 101, 102, 103, 104, 105, 106, 107, 108, 109, 110, 111, 112, 113, 114, 115, 116, 117, 118, 119, 120, 121, 122, 123, 124, 125, 126, 127, 128, 129, 130, 131, 132, 133, 134, 135, 136, 137)
-
-
87. The electrochromic material of claim 81 wherein said electrochromic material is represented by the following structure:
-
88. The electrochromic material of claim 81 wherein said electrochromic material is represented by the following structure:
-
89. The electrochromic material of claim 81 that incorporate that incorporate functional groups that facilitate the irreversible chemisorption nanocrystalline metal oxide electrodes.
-
90. The electrochromic material of claim 81 wherein R 1 thru R5 together or separately comprise carboxylate, salicylate, or phosphonate groups that facilitate irreversible chemisorption towards metal oxide electrodes.
-
91. The electrochromic material of claim 81 wherein the electrochromic material is represented by the following structure:
-
92. The electrochromic material of claim 81 wherein the electrochromic material is represented by the following structure:
-
93. The electrochromic material of claim 81 wherein the electrochromic material is represented by the following structure:
-
94. The electrochromic material of claim 81 wherein said electrochromic material is represented by the formula:
-
95. The electrochromic material of claim 81 wherein said electrochromic material is represented by the formula
-
96. The electrochromic material of claim 81 wherein said electrochromic material is represented by the formula
-
97. The electrochromic material of claim 37 wherein X represents nitrogen and n is 1.
-
98. The electrochromic material of claim 97 wherein said electrochromic material is at least one member selected from the group consisting of:
-
99. The electrochromic material of claim 37 wherein X is oxygen or sulfur, and the value of n is 0.
-
100. The electrochromic material of claim 37 wherein said electrochromic material has an electrochemical reduction potential of from −
- 1.0 to +0.2 Volts vs SCE.
-
101. The electrochromic material of claim 37 wherein said electrochromic material has an electrochemical reduction potential of from −
- 0.8 to −
0.1 Volts vs SCE.
- 0.8 to −
-
102. The electrochromic material of claim 37 wherein said electrochromic material has an electrochemical reduction potential of from −
- 0.6 to −
0.2 Volts vs SCE.
- 0.6 to −
-
103. The electrochromic material of claim 37 wherein said electrochromic material comprises electrochromic sulfone structures that have groups for linking to nanocrystalline TiO2 or SnO2.
-
104. The electrochromic material of claim 37 wherein said electrochromic material is capable of color change upon reduction.
-
105. The electrochromic material of claim 104 wherein said color change upon reduction is reversible.
-
106. The electrochromic material of claim 37 wherein said electrochromic material is stable in the reduced and unreduced states.
-
107. The electrochromic material of claim 37 wherein said electrochromic material is colorless and upon reduction is colored.
-
108. The electrochromic material of claim 37 which upon reduction exhibits optical absorption between 390 and 750 nm with an extinction coefficient between 5000 M−
- 1 cm−
1 and 25,000 M−
1 cm−
1.
- 1 cm−
-
109. The electrochromic device of claim 37 wherein said at least two electrodes comprise a first and second electrode, wherein said first electrode is disposed on said substrate, wherein said substrate is transparent, and where at least one of said first and second electrodes is transparent.
-
110. The electrochromic device of claim 109 wherein said first electrode is a cathode.
-
111. The electrochromic device of claim 109 wherein said first electrode is transparent.
-
112. The electrochromic device of claim 111 wherein said first electrode comprises ITO.
-
113. The electrochromic device of claim 111 wherein said first electrode comprises fluorine doped tin oxide (FTO), indium tin oxide (ITO), doped zinc oxide.
-
114. The electrochromic device of claim 113 wherein said first electrode further comprises other metal oxides of indium, titanium, cadmium, gallium-indium, niobium, tin, cerium oxide, zirconium, hafnium and tantalum.
-
115. The electrochromic device of claim 113 wherein said first electrode further comprises other metal oxides of indium, titanium, or tin.
-
116. The electrochromic device of claim 109 wherein said first electrode is reflective.
-
117. The electrochromic device of claim 109 wherein said second electrode comprises an anode.
-
118. The electrochromic device of claim 109 wherein said second electrode is transparent.
-
119. The electrochromic device of claim 118 wherein said second electrode comprises ITO.
-
120. The electrochromic device of claim 118 wherein said second electrode comprises fluorine doped tin oxide (FTO), indium tin oxide (ITO), doped zinc oxide.
-
121. The electrochromic device of claim 120 wherein said second electrode further comprises other metal oxides of indium, titanium, cadmium, gallium-indium, niobium, tin, cerium oxide, zirconium, hafnium and tantalum.
-
122. The electrochromic device of claim 120 wherein said second electrode further comprises metal oxides of indium, titanium, or tin.
-
123. The electrochromic device of claim 109 wherein said second electrode is reflective.
-
124. The electrochromic device of claim 37 wherein said electrochromic material is located in an electrochromic layer.
-
125. The electrochromic device of claim 124 wherein said electrochromic material is electrochromic layer is in the form of a solution, gel, or solid layer.
-
126. The electrochromic device of claim 124 wherein said electrochromic layer is a polymer or polymer composite.
-
127. The electrochromic device of claim 124 wherein said electrochromic layer is an insoluble film on said first electrode or said second electrode.
-
128. The electrochromic device of claim 124 wherein said electrochromic layer is chemically bonded to said first electrode or said second electrode.
-
129. The electrochromic device of claim 124 wherein said electrochromic layer is chemisorbed to said first electrode or said second electrode.
-
130. The electrochromic device of claim 109 further comprising at least one reflective nanoporous-nanocrystalline semiconducting film that is intermediate to said first electrode or said second electrode.
-
131. The electrochromic device of claim 130 wherein said electrochromophore is chemisorbed to said at least one of said nanoporous-nanocrystalline semiconducting films.
-
132. The electrochromic device of claim 130 wherein said nanocrystalline semiconducting film is a metal oxide.
-
133. The electrochromic device of claim 132 wherein said metal oxide is any suitable metal selected from the group consisting of titanium, zirconium, hafnium, chromium, molybdenum, tungsten, vanadium, niobium, tantalum, silver, zinc, strontium, iron (Fe 2+ or Fe 3+), nickel or a mixed metal oxide thereof.
-
134. The electrochromic device of claim 132 wherein said metal oxide is any suitable metal selected from titanium, molybdenum, or tungsten.
-
135. The electrochromic device of claim 130 wherein said nanocrystalline semiconducting film is TiO2, WO3, MoO3, ZnO, SnO2 and SnO2 doped with Sb.
-
136. The electrochromic device of claim 130 wherein said nanocrystalline semiconducting film is TiO2, SnO2 and SnO2 doped with Sb.
-
137. The electrochromic device of claim 130 wherein said at least one nanocrystalline semiconducting film is independently deposited on said first electrode and said second electrode.
Specification