Near infrared-absorbing electrochromic compounds and devices comprising same
First Claim
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1. An electrochromic medium comprising at least one solution-phase anodic compound, where an oxidized form of said anodic compound has a ESOMO−
- EHDOMO of less than 3.6 eV, a redox potential greater than about 90 mV, and an absorption band having a λ
max greater than approximately 750 nm, excluding therefrom the compounds of the formula;
wherein R51 and R54 are the same or different and are each selected from hydrogen and dialkylamino, wherein the alkyl groups are the same or different and are each of 1 to 6 carbon atoms, R52 is oxygen, sulfur or NR55, wherein R55 is the same as or different from R53 and both R55 and R53 are selected from hydrogen, alkyl of 1 to 10 carbon atoms, phenyl optionally substituted at any one position with chloride, bromide, iodide, cyano, or alkyl of 1 to 4 carbon atoms, or benzyl, optionally substituted at any one position of the phenyl group with chloride, bromide, iodide, cyano, or alkyl of 1 to 4 carbon atoms.
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Abstract
Electrochromic compounds capable of reversibly attenuating the transmittance of the near infrared portion of the electromagnetic spectrum are provided. These compounds exhibit an energy difference between the singly occupied molecular orbital (SOMO) energy and the highest doubly occupied molecular orbital (HDOMO) energy (ESOMO−EHDOMO) of less than about 3.6 eV. In addition, these compounds have a transition moment of the configuration made up of the HDOMO and SOMO that is “long axis polarized”.
241 Citations
39 Claims
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1. An electrochromic medium comprising at least one solution-phase anodic compound, where an oxidized form of said anodic compound has a ESOMO−
- EHDOMO of less than 3.6 eV, a redox potential greater than about 90 mV, and an absorption band having a λ
max greater than approximately 750 nm, excluding therefrom the compounds of the formula;
wherein R51 and R54 are the same or different and are each selected from hydrogen and dialkylamino, wherein the alkyl groups are the same or different and are each of 1 to 6 carbon atoms, R52 is oxygen, sulfur or NR55, wherein R55 is the same as or different from R53 and both R55 and R53 are selected from hydrogen, alkyl of 1 to 10 carbon atoms, phenyl optionally substituted at any one position with chloride, bromide, iodide, cyano, or alkyl of 1 to 4 carbon atoms, or benzyl, optionally substituted at any one position of the phenyl group with chloride, bromide, iodide, cyano, or alkyl of 1 to 4 carbon atoms. - View Dependent Claims (2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12)
- EHDOMO of less than 3.6 eV, a redox potential greater than about 90 mV, and an absorption band having a λ
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13. An electrochromic medium comprising at least one solution-phase anodic compound, where an oxidized form of said anodic compound has an ESOMO−
- EHDOMO of less than 3.6 eV, and an absorption band having a λ
max greater than approximately 750 nm, excluding therefrom the compounds of the formula;
wherein R76 is oxygen or sulfur, R80 is hydrogen or dialkylamino, wherein the alkyl groups are the same or different and are each of 1 to 6 carbon atoms, and R77 and R78 are the same or different and are each selected from hydrogen, alkyl of 1 to 6 carbon atoms, phenyl optionally substituted at any one position with an alkyl group of 1 to 6 carbon atoms, and benzyl, optionally substituted at any one position of the phenyl group with an alkyl group of 1 to 6 carbon atoms, and excluding therefrom the compounds of the formula;
wherein R51 and R54 are the same or different and are each selected from hydrogen and dialkylamino, wherein the alkyl groups are the same or different and are each of 1 to 6 carbon atoms;
R52 is oxygen, sulfur or NR55, wherein R55 is the same as or different from R53 and both R55 and R53 are selected from hydrogen, alkyl of 1 to 10 carbon atoms, phenyl optionally substituted at any one position with chloride, bromide, iodide, cyano, or alkyl of 1 to 4 carbon atoms, or benzyl, optionally substituted at any one position of the phenyl group with chloride, bromide, iodide, cyano, or alkyl of 1 to 4 carbon atoms.- View Dependent Claims (14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24)
- EHDOMO of less than 3.6 eV, and an absorption band having a λ
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25. An electrochromic medium comprising a crosslinked polymer matrix and at least one anodic compound, where an oxidized form of said anodic compound has a redox potential greater than about 90 mV, and an absorption band having a λ
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max greater than approximately 750 nm, excluding therefrom the compounds of the formula;
wherein R51 and R54 are the same or different and are each selected from hydrogen and dialkylamino, wherein the alkyl groups are the same or different and are each of 1 to 6 carbon atoms;
R52 is oxygen, sulfur or NR55, wherein R55 is the same as or different from R53 and both R55 and R53 are selected from hydrogen, alkyl of 1 to 10 carbon atoms, phenyl optionally substituted at any one position with chloride, bromide, iodide, cyano, or alkyl of 1 to 4 carbon atoms, or benzyl, optionally substituted at any one position of the phenyl group with chloride, bromide, iodide, cyano, or alkyl of 1 to 4 carbon atoms.- View Dependent Claims (26, 27, 28, 29, 30, 31, 32, 33, 34, 35)
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max greater than approximately 750 nm, excluding therefrom the compounds of the formula;
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36. An electrochromic window comprising an electrochromic medium, said electrochromic medium comprising a crosslinked polymer matrix and an anodic compound, wherein said window is capable of absorbing in the NIR portion of the electromagnetic spectrum, and said anodic compound has a redox potential greater than about 90 mV, and an absorption band having a λ
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max greater than approximately 750 nm, excluding therefrom the compounds of the formula;
wherein R51 and R54 are the same or different and are each selected from hydrogen and dialkylamino, wherein the alkyl groups are the same or different and are each of 1 to 6 carbon atoms;
R52 is oxygen, sulfur or NR55, wherein R55 is the same as or different from R53 and both R55 and R53 are selected from hydrogen, alkyl of 1 to 10 carbon atoms, phenyl optionally substituted at any one position with chloride, bromide, iodide, cyano, or alkyl of 1 to 4 carbon atoms, or benzyl, optionally substituted at any one position of the phenyl group with chloride, bromide, iodide, cyano, or alkyl of 1 to 4 carbon atoms.- View Dependent Claims (37, 38, 39)
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max greater than approximately 750 nm, excluding therefrom the compounds of the formula;
Specification