Electrochromic device

• US 6,519,072 B2
• Filed: 08/16/2001
• Issued: 02/11/2003
• Est. Priority Date: 02/18/1999
• Status: Expired due to Fees

• Current Assignee: Nippon Mitsubishi Oil Corporation (ENEOS Holdings, Inc.)
• Original Assignee: Nippon Mitsubishi Oil Corporation (ENEOS Holdings, Inc.)
• Inventors: Kobayashi, Masaaki, Minami, Masaki, Kubo, Takaya, Nishikitani, Yoshinori, Imafuku, Hiroshi, Iaki, Keizo
• Primary Examiner(s): Mai, Huy
• Assistant Examiner(s): TRA, TUYEN Q
• Application Number:
  US09/931,356
• Publication Number:
  US 20020015214A1
• Time in Patent Office: 544 Days
• Field of Search: 359/265, 359/273, 359/267, 359/275, 359/266, 359/268, 359/269, 359/270, 359/271, 359/272, 359/274, 252/583, 252/600, 204/290.07, 544/347, 546/257
• US Class Current: 359/272
• CPC Class Codes: C09K 2211/1029 containing one nitrogen atom as the heteroatom
• CPC Class Codes: C09K 2211/187 of the iron group metals, i.e. Fe, Co or Ni
• 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 2001/1502 complementary cell
• CPC Class Codes: G02F 2001/15145 the electrochromic layer comprises a mixture of anodic and cathodic compounds

Abstract

An electrochromic element comprises an ion conduction layer between two conducting substrates, at least one of which is transparent. The ion conduction layer contains an organic compound, which has both a structure exhibiting a cathodic electorchromic characteristic and a structure exhibiting an anodic electrochromic characteristic.

Claims

1. An electrochromic device having an ion conductive layer disposed between two electrically conductive substrates, at least one of which is transparent, wherein said ion conductive layer contains an organic compound having a structure exhibiting a cathodic electrochromic characteristic and a structure exhibiting an anodic electrochromic characteristic, and wherein the organic compound is a metallocene-bipyridine derivative represented by one of formulae (4) to (7):

wherein A⁻

and B⁻

are each independently a pair-anion selected from the group consisting of a halogen anion, ClO₄⁻

, BF₄⁻

, PF₆⁻

, AsF₆⁻

, SbF₆⁻

, CHCOO⁻

, and CH₃(C₆H₄)SO₃⁻

;

R¹ and R² are each independently a hydrocarbon group selected from the group consisting of an alkyl, alkenyl and aryl group having 1 to 10 carbon atoms, in the case where R¹ or R² is an aryl group, the aryl group forms a condensed ring together with a cyclopentadienyl ring, m is an integer of 0≦

m≦

4, n is an integer of 0≦

n≦

4;

Me represents Cr, Co, Fe, Mg, Ni, Os, Ru, V, X—

HF—

Y, X—

Mo—

Y, X—

Nb—

Y, X—

Ti—

Y, X—

V—

Y or X—

Zr—

Y wherein X and Y are each independently selected from the group consisting of hydrogen, halogen, and an alkyl group having 1 to 12 carbon atoms;

R³ and R⁴ are each independently a hydrocarbon residue having 1 to 20 carbon atoms;

R⁵ is a hydrocarbon group selected from the group consisting of an alkyl, cycloalkyl, alkenyl, aryl, or aralkyl group having 1 to 20 carbon atoms, a heterocyclic group having 4 to 20 carbon atoms, and a substituted hydrocarbon or heterocyclic group obtained by substituting part of the hydrocarbon group or heterocyclic group with a substituent group.

2. The electrochromic device according to claim 1, wherein the organic compound is a ferrocene-bipyridine derivative represented by the formula

wherein R⁶ and R⁷ are each independently an alkylene group having 1 to 20 carbon atoms.

3. The electrochromic device according to claim 1 wherein the organic compound is a ferrocene-bipyridine derivative represented by the formula

wherein R⁸ is an alkylene group having 1 to 20 carbon atoms and R⁹ is selected from the group consisting of an alkyl or alkenyl group having 1 to 10 carbon atoms, an aryl group having 6 to 18 carbon atoms, a substituted aryl group obtained by substituting part of the aryl group with an alkyl or alkoxy group having 1 to 6 carbon atoms or an aryl group having 6 to 8 carbon atoms, and an aralkyl group.

4. The electrochromic device according to claim 1 wherein said organic compound is a ferrocene-bipyridine derivative represented by the formula

wherein R¹⁰ is an alkylene group having 1 to 20 carbon atoms and Ar¹ is a nitrogen-containing heterocyclic group selected from the group consisting of pyridine, pyrimidine and isoquinolyl groups and a group obtained by substituting part of the nitrogen-containing heterocyclic group with an alkyl and/or alkoxy group having 1 to 5 carbon atoms.

5. An electrochromic device having an ion conductive layer disposed between two electrically conductive substrates, at least one of which is transparent, wherein said ion conductive layer contains an organic compound having a structure exhibiting a cathodic electrochromic characteristic and a structure exhibiting an anodic electrochromic characteristic, and wherein the organic compound is a ferrocene-bipyridine derivative represented by the formula

wherein R¹¹ is an alkylene group having 1 to 20 carbon atoms, R¹² is selected from the group consisting of alkyl, alkenyl, aryl, and aralkyl groups having 1 to 20 carbon atoms, Ar² is a divalent aromatic hydrocarbon group having 6 to 20 carbon atoms, and wherein A⁻

and B⁻

are each independently a pair-anion selected from the group consisting of a halogen anion, ClO₄⁻

, BF₄⁻

, PF₆⁻

, AsF₆⁻

, SbF₆⁻

, CHCOO⁻

, and CH₃(C₆H₄).

6. The electrochromic device according to claim 5 wherein said Ar² in formula (11) is an arylene or alkylarylene group.