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(12) United States Patent (10) Patent No.: US 6,961,168 B2 Agrawal Et Al

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(12) United States Patent (10) Patent No.: US 6,961,168 B2 Agrawal Et Al USOO696 1168B2 (12) United States Patent (10) Patent No.: US 6,961,168 B2 Agrawal et al. (45) Date of Patent: Nov. 1, 2005 (54) DURABLE ELECTROOPTIC DEVICES 4.902,108 A 2/1990 Byker ........................ 350/357 COMPRISING IONIC LIQUIDS 5,099,356 A * 3/1992 Ohsawa et al. ............. 359/270 (75) Inventors: Anoop Agrawal, Tucson, AZ (US); (Continued) John P. Cronin, Tucson, AZ (US); Juan C. L. Tonazzi, Tucson, AZ (US); FOREIGN PATENT DOCUMENTS Benjamin P. Warner, Los Alamos, NM (US); T. Mark McCleskey, Los JP O83294.79 6/1998 ......... CO7C/57/145 JP O1933.63 12/2001 .......... HO1M/10/40 Alamos, NM (US); Anthony K. WO O127690 4/2001 Burrell, Los Alamos, NM (US) WO O163350 8/2001 ........... GO2F/1/153 (73) Assignee: The Regents of the University of California, Los Alamos, NM (US) OTHER PUBLICATIONS (*) Notice: Subject to any disclaimer, the term of this Charles M. Gordon, “New Developments in Catalysis. Using patent is extended or adjusted under 35 Ionic Liquids, Applied Catalysis A: General, Vol. 222, pp. U.S.C. 154(b) by 24 days. 101-117, 2001. (21) Appl. No.: 10/741,903 (Continued) (22) Filed: Dec. 19, 2003 (65) Prior Publication Data Primary Examiner-Georgia Epps ASSistant Examiner William Choi US 2004/0257633 A1 Dec. 23, 2004 (74) Attorney, Agent, or Firm Samuel L. Borkowsky Related U.S. Application Data (57) ABSTRACT (63) Continuation-in-part of application No. 10/600,807, filed on Electrolyte Solutions for electrochromic devices Such as rear Jun. 20, 2003, now Pat. No. 6.853,472. view mirrors and displays with low leakage currents are (60) Provisional application No. 60/390,611, filed on Jun. 21, prepared using inexpensive, low conductivity conductors. 2002, and provisional application No. 60/502,133, filed on Preferred electrolytes include bifunctional redox dyes and Sep. 11, 2003. molten salt solvents with enhanced stability toward ultra (51) Int. Cl. ........................... G02F1/153; G02F1/00; Violet radiation. The Solvents include lithium or quaternary GO2B 5/23 ammonium cations, and perfluorinated Sulfonylimide anions (52) U.S. Cl. ....................... 359/273; 359/270; 35.9/321; selected from trifluoromethylsulfonate (CFSO), bis 252/583; 252/586 (trifluoromethylsulfonyl)imide ((CFSO)N), bis (58) Field of Search ................................. 359/265-275, (perfluoroethylsulfonyl)imide ((CFCFSO)N) and tris 359/321, 322; 252/582,583, 586 (trifluoromethylsulfonyl)methide ((CFSO)C). Electroluminescent, electrochromic and photoelectrochro (56) References Cited mic devices with nanostructured electrodes include ionic liquids with bifunctional redox dyes. U.S. PATENT DOCUMENTS 4,671,619 A 6/1987 Kamimori et al. .......... 350/357 17 Claims, 12 Drawing Sheets US 6,961,168 B2 Page 2 U.S. PATENT DOCUMENTS D. Behar, P. Neta, and Carl Schultheisz, "Reaction Kinetics 5,140,455 A 8/1992 Varaprasad et al. ......... 359/275 in Ionic Liquids as Studied by Pulse Radiolysis: Redox 5,142,407 A 8/1992 Varaprasad et al. ......... 359/276 Reactions in the Solvents Methyltributylammonium Bis(tri 5,500,760 A 3/1996 Varaprasad et al. ......... 359/272 fluoromethylsulfonyl)imide and N-Butylpyridinium Tet 5,604,626 A 2/1997 Teowee et al. ............. 359/265 rafluoroborate,” J. Phys. Chem. A, vol. 106, pp. 3139–3147, 5,729,379 A 3/1998 Allemand et al. .......... 359/270 2002. 5,827.602 A 10/1998 Koch et al. ................. 429/194 Mark Niemeyer, “o-Donor Versus m-t-Arene Interactions 5,838,483 A 11/1998 Teowee et al. ............. 359/265 5,864,419 A 1/1999 Lynam ....................... 359/265 in Monomeric Europium(II) and Ytterbium(II) Thiolates 5.940,201 A 8/1999 Ash et al. ................... 359/267 An Experimental and Computational Study, Eur. J. Inorg. 5.998.617 A 12/1999 Srinivasa et al. ........... 544/347 Chem., pp. 1969–1981, 2001. 6,045,724 A 4/2000 Varaprasad et al. ......... 252/583 A. W. CZanderna, D. K. Benson, G. J. Jorgensen, J.-G. 6,067,184 A 5/2000 Bonhote et al. ............ 359/265 Zhang, C. E. Tracy, and S. K. DEB, “Durability Issues and 6,118,572 A 9/2000 Kostecki et al. ............ 359/265 Service Lifetime Prediction of Electrochromic Windows for 6,122,093 A 9/2000 Lynam ....................... 359/275 Buildings Applications,” Solar Energy Materials & Solar 6,141,137 A 10/2000 Byker et al. ................ 359/265 6,172,794 B1 1/2001 Burdis ........................ 359/269 Cells, vol. 56, pp. 419–436, 1999. 6,178,034 B1 1/2001 Allemand et al. .......... 359/265 Dave Thieste, Harlan J. Byker, Kelvin Baumann, and 6,188,505 B1 * 2/2001 Lomprey et al. ........... 359/265 Ramanujan Srinivasa, “Near Infrared-Absorbing Electro 6,241,916 B1 6/2001 Claussen et al. ............ 252/583 chromic Compounds and Devices Comprising the Same,” 6.245,262 B1 6/2001 Varaprasad et al. ........ 264/1.31 PCT Application WO99/45081, published Sep. 10, 1999. 6,246,505 B1 6/2001 Teowee et al. ............. 359/241 6,266,177 B1 7/2001 Allemand et al. .......... 359/265 Clemens Bechinger, Suzanne Ferrere, Arie Zaban, Julian 6.297,900 B1 10/2001 Tulloch et al............... 359/275 Sprague, and Brian A. Greeg, “Photoelectrochromic Win 6,310,714 B1 10/2001 Lomprey et al. ........... 359/265 dows and Displays,” Nature, vol. 383, pp. 608-610, Oct. 6,317,248 B1 11/2001 Agrawal et al. ............ 359/265 1996. 6,327,070 B1 12/2001 Heuer et al. ................ 359/269 6,344.918 B1 2/2002 Berneth et al. ............. 359/275 Gimtong Teowee, Todd Gudgel, Kevin McCarthy, Anoop 6,362.914 B2 3/2002 Baumann et al. ........... 359/265 Agrawal, Pierre Allemand, John Cronion, “User Control 6,365,301 B1 4/2002 Michot et al. .............. 429/307 lable Photochromic (UCPC) Devices.” Electrochimica Acta, 6,369,934 B1 4/2002 Bechinger et al. .......... 359/265 vol. 44, pp. 3017-3026, 1999. 6,372,159 B1 4/2002 Berneth et al. ............. 252/583 Zhifeng Ding, Bernadette M. Quinn, Santosh K. Haram, 6,420,036 B1 7/2002 Varaprasad et al. ......... 428/432 6,519,072 B2 2/2003 Nishikitani et al. ......... 359/272 Lindsay E. Pell, Brian A. Korgel, Allen J. Bard, “Electro 6,525,861 B1 2/2003 Roberts et al. ............. 359/265 chemistry and Electrogenerated Chemiluminescence from 6,605,239 B2 8/2003 Fitzmaurice et al. ........ 252/583 Silicon Nanocrystal Quantum Dots,” Science, vol. 296, pp. 6,816,298 B2 11/2004 Nishikitani et al. ......... 359/272 1293–1297, May 2002. 2002/0012155 A1 1/2002 Baumann et al. Sand Kwon Lee, Mark M. Richter, Lucjan Strekowsky, and 2003/003O883 A1 2/2003 Giri et al. Allen J. Bard, “Electrogenerated Chemiluminescence. 61. Near-IR Electrogenerated Chemiluminescence, Electro OTHER PUBLICATIONS chemistry, and Spectroscopic Properties of a Heptamethine Martyn J. Earle, Paul B. McCormac, and Kenneth R. Sed Cyanine Dye in MeCN,” Analytical Chemistry, vol. 69, pp. don, “Diels-Alder Reactions in Ionic Liquids,” Green 4126–4133, 1997. Chemistry, pp. 23–25, Feb. 1999. Zhifeng Ding, "Electrochemistry and Electrogenerated J. Sun, M. Forsyth, and D. R. Macfarlane, “Room-Tem perature Molten Salts Based on the Quaternary Ammonium Chemiluminescence from Silicon Nanocrystal Quantum Ion.” J. Phys. Chem. B. vol. 102, pp. 8858-8865, 1998. Dots,” Science, vol. 296, pp. 1293-1297, May 2002. Yu. F. Pugachev, I. V. Neverov, “An Electrochromic System Sang Kwon Lee, “Electrogenerated Chemiluminescence. Based on Methyl Viologen Influence of the Polymer, Base 61. Near-IR Electrogenerated Chemiluminescence, Electro Electrolyte, and Solvent Type on its Chief Characteristics.” chemistry, and Spectroscopic Properties of a Heptamethine Ulyanovsk Polytechnic Institute. Translated from Elek Cyanine Dye in MeCN,” Analytical Chemistry, vol. 69, pp. trokhimiya, vol. 22, No. 1, pp. 58-62, Jan. 1986. 4126–4133, 1997. “Ultraviolet Stabilizers,” Modern Plastics World Encyclo Alexander Michaelis, Horst Berneth, Dietrich Haarer, Ser pedia, pp. C-120-C-122, 2001. guei Kostromine, Ralph Neigl, and Ralph Schmidt, “Elec Mark J. Muldoon, Andrew J. McLean, Charles M. Gordon, trochromic Dye System for Smart Window Applications.” and Ian R. Dunkin, “Hydrogen Abstraction From Ionic Adv. Mater, vol. 13, No. 23, Dec. 3, 2001. Liquids by Benzophenone Triplet Excited States,” Chem. Commun., pp. 2364-2365, 2001. * cited by examiner U.S. Patent Nov. 1, 2005 Sheet 1 of 12 US 6,961,168 B2 U.S. Patent Nov. 1, 2005 Sheet 2 of 12 US 6,961,168 B2 s U.S. Patent Nov. 1, 2005 Sheet 3 of 12 US 6,961,168 B2 8 E:it, ifS. s: s l R.\le\, i.S. -s 8 it U.S. Patent Nov. 1, 2005 Sheet 4 of 12 US 6,961,168 B2 i s bu eq 0 sqW U.S. Patent Nov. 1, 2005 Sheet 5 of 12 US 6,961,168 B2 o 8 s 3. 3 O S 3 5 3 n d ar cy S 2 U.S. Patent Nov. 1, 2005 Sheet 6 of 12 US 6,961,168 B2 sss s s S C s O O s s co na e u S. (uu OSS) 6. U.S. Patent Nov. 1, 2005 Sheet 7 of 12 US 6,961,168 B2 t s s (9 l 8 3 U.S. Patent Nov. 1, 2005 Sheet 8 of 12 US 6,961,168 B2 VO f U.S. Patent Nov. 1, 2005 Sheet 9 of 12 US 6,961,168 B2 (O) Asoo’s Wu U.S. Patent Nov. 1, 2005 Sheet 10 of 12 US 6,961,168 B2 O O d O CO O d O N O C2 O to to S VNGN o V d O O Uta LO O d O r O O Lo Lo Lo N to co Lo Q. Lo - C LO v CY) CN w (o) ASOSA ul U.S. Patent Nov.
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