Electrochromic compounds

• US 6,037,471 A
• Filed: 08/26/1998
• Issued: 03/14/2000
• Est. Priority Date: 04/02/1997
• Status: Expired due to Term

• Current Assignee: Gentex Corporation
• Original Assignee: Gentex Corporation
• Inventors: French, Darla J., Guarr, Thomas F., Byker, Harlan J., Theiste, David A., Baumann, Kelvin L., Srinivasa, Ramanujan, Lin, Rongguang
• Primary Examiner(s): Morris, Patricia L.
• Application Number:
  US09/140,310
• Time in Patent Office: 566 Days
• Field of Search: 546/257
• US Class Current: 546/257
• CPC Class Codes: C07D 213/22 containing two or more pyridine rings directly linked together, e.g. bipyridyl
• CPC Class Codes: C07D 241/36 condensed with carbocyclic rings or ring systems
• CPC Class Codes: C07D 241/46 Phenazines
• 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

Abstract

An improved electrochromic device, the device incorporating an electrochromic medium that comprises at least three electroactive materials having absorption spectra that add together such that the color of the electrochromic medium can be pre-selected by individually choosing the concentrations of the at least three electroactive materials. The electrochromic medium generally maintains the pre-selected perceived color throughout its normal range of voltages when used in an electrochromic device. The at least three electroactive materials include at least one electrochemically reducible material (cathodic material), at least one electrochemically oxidizable material (anodic material) and at least one additional electroactive material which may be either an anodic or cathodic material. Thus, there are always three electroactive materials present in the medium, with at least two either being anodic or cathodic materials. The pre-selected color may be chosen from a wide variety of colors and may be, for example, red, orange, yellow, green, blue, purple. For electrochromic mirrors for motor vehicles, a presently preferred color is gray.

Claims

1. A salt of the compound having the formula:

##STR3## where if R₁ is phenyl substituted with methoxy or a trimethyl substituted phenyl, R_1'"'"' is alkyl having 1 to 9 carbons, and R₂, R_2'"'"', R₆ and R_6'"'"' are hydrogen; and

if R₁ and R_1'"'"' are m-xylyl and R₂, R_2'"'"', R₆, and R_6'"'"' are hydrogen;

if R₁ is phenyl, R_1'"'"' is an alkyl substituted aryl having 18 carbons, and R₂, R_2'"'"', R₆, and R_6'"'"' are hydrogen;

if R₁ and R_1'"'"' are methyl, R₂ is aralkyl having 8 or 9 carbons or alkyl having 6 carbons, and R_2'"'"', R₆, and R_6'"'"' are the same or different and are selected from the group selected from hydrogen and alkyl and aralkyl having from 1 to 9 carbons.

2. A salt of claim 1, where the anion is selected from the group of tetrafluoroborate, hexafluorophosphate, perchlorate and a halide.

3. A salt of claim 1, where R₁ and R_1'"'"' are m-xylyl attached at the 2 or 5 position and R₂, R_2'"'"', R₆, and R_6'"'"' are hydrogen.

4. A salt of claim 1, where R₁ is phenyl, R_1'"'"' is an alkyl substituted phenyl having 18 carbons, and R₂, R_2'"'"', R₆, and R_6'"'"' are hydrogen.

5. A salt of claim 1, where R₁ and R_1'"'"' are methyl, R₂ is selected from the group of phenylpropyl, phenylethyl and n-hexyl, and R_2'"'"', R₆, and R_6'"'"', are the same or different and are selected from the group of hydrogen, alkyl having 1-6 carbons, phenylpropyl and phenylethyl.

6. The salt of claim 1, where the salt is selected from the group of 1,1'"'"'-bis(2,6-dimethylphenyl)-4,4'"'"'-dipyridinium;

1,1'"'"'-bis(3,5-dimethylphenyl)-4,4'"'"'-dipyridinium;

1-phenyl-1'"'"'-(4-dodecylphenyl)-4,4'"'"'-dipyridinium;

1-(3,5-dimethoxyphenyl)-1'"'"'-methyl-4,4'"'"'-dipyridinium;

1-(4 -methoxyphenyl)-1'"'"'-methyl-4,4'"'"'-dipyridinium;

1-methyl-1'"'"'-(2,4,6-trimethylphenyl)-4,4'"'"'-dipyridinium;

1,1'"'"'-dimethyl-2-(3-phenyl(n-propyl))-4,4'"'"'-dipyridinium;

1,1'"'"'-dimethyl-2-(2-phenylethyl)-4,4'"'"'-dipyridinium;

1,1'"'"'-dimethyl-2,2'"'"'-bis(3-phenyl(n-propyl))4,4'"'"'-dipyridinium;

1,1'"'"'-dimethyl-2,2'"'"'-bis(2-phenylethyl)-4,4'"'"'-dipyridinium;

1,1'"'"',2,2'"'"',6-pentamethyl-6'"'"'-(3-phenyl(n-propyl))-4,4'"'"'-dipyridinium;

1,1'"'"',2,2'"'"',6-pentamethyl-6'"'"'-2-phenylethyl4,4'"'"'-dipyridinium;

1,1'"'"',2,2'"'"'-tetramethyl-6,6'"'"'-bis(2-phenylethyl)- 4,4'"'"'-dipyridinium;

1,1'"'"',2-trimethyl-2'"'"', 6,6'"'"'-tris(2-phenylethyl)-4,4'"'"'-dipyridinium; and

1,1'"'"',2,2'"'"',6-pentamethyl-6'"'"'-hexyl4,4'"'"'-dipyridinium.