Electrochromic device

• US 20030206326A1
• Filed: 06/02/2003
• Published: 11/06/2003
• Est. Priority Date: 05/15/2000
• Status: Active Grant

• Current Assignee: Bayer AG
• Original Assignee: Bayer AG
• Inventors: Neigl, Ralf, Berneth, Horst, Shelepin, Igor, Gavrilov, Vladimir
• Granted Patent: US 7,106,489 B2
• Time in Patent Office: Days
• US Class Current: 359/265
• 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 electrochromic device comprising a pair of glass or plastic plates or plastic films of which at least one plate or film, preferably both plates or films, are provided on in each case one side with an electrically conductive coating, of which at least one plate or film and its conductive coating are transparent, of which the other may be mirrored, and of which in the case of at least one of the two plates or films the electrically conductive layer can be divided into separate, individually contacted area segments, where the plates or films are joined together via a sealing ring on the sides of their conductive coating, and the volume formed by the two plates or films and the sealing ring is filled with an electrochromic medium which comprises at least one reducible electrochromic substance OX₂ and at least one oxidizable electrochromic substance RED₁, characterized in that one OX₂ corresponds to the formula

in which

R²⁰¹ and R²⁰², independently of one another, are alkyl, cycloalkyl, alkenyl, aralkyl, aryl, —[C(PQ)]⁻ or a bivalent bridge B,

Z²⁰¹ is a bivalent radical of the formulae CR²¹⁰R²¹¹, O, C═O or o-phenylene,

R²¹⁰ and R²¹¹, independently of one another, are hydrogen, methyl or ethyl, or

CR²¹⁰R²¹¹ is C₃- to C₇-cycloalkane-1,1-diyl,

the rings C, D, E and F, independently of one another, may be substituted by up to 4 alkyl and/or alkoxy radicals, or the rings C and D or the rings E and F, respectively, may be linked via a —(CH₂)₄— or —CH═CH—CH═CH— bridge,

P and Q, independently of one another, are —CN or —COO-alkyl, and

X— is an anion,

has improved properties and comprises electrochromic compounds which are readily obtainable synthetically.

Claims

1. Electrochromic device comprising a pair of glass or plastic plates or plastic films of which at least one plate or film, preferably both plates or films, are provided on in each case one side with an electrically conductive coating, of which at least one plate or film and its conductive coating are transparent, of which the other may be mirrored, and of which in the case of at least one of the two plates or films the electrically conductive layer can be divided into separate, individually contacted area segments, where the plates or films are joined together via a sealing ring on the sides of their conductive coating, and the volume formed by the two plates or films and the sealing ring is filled with an electrochromic medium which comprises at least one reducible electrochromic substance OX₂ and at least one oxidizable electrochromic substance RED₁, characterized in that one OX₂ corresponds to the formula

2. Electrochromic device according to claim 1,

wherein

R²⁰¹ and R²⁰², independently of one another, are C₁- to C₁₈-alkyl, C₃- to C₈-cycloalkyl, C₂- to C₁₈-alkenyl, C₇- to C₁₀-aralkyl, C₆- to C₁₀-aryl or —

[C(CN)₂]⁻

, —

[C(CN)COO—

C₁- to —

C₄-alkyl]⁻

or —

[C(COO—

C₁- to —

C₄-alkyl)₂]⁻

,

Z²⁰¹ is CH₂, C═

O or o-phenylene,

the rings C, D, E and F, independently of one another, may be substituted by up to 4 methyl radicals, or the rings C and D or the rings E and F, respectively, may be linked via a —

(CH₂)₄—

or —

CH═

CH—

CH═

CH—

bridge, and

X⁻

is an anion.

3. Electrochromic device according to claim 1,

wherein

at least one of R²⁰¹ and R²⁰² is a bivalent bridge B and, if applicable, the other is C₁- to C₁₈-alkyl, C₃- to C₈-cycloalkyl, C₂- to C₁₈-alkenyl, C₇- to C₁₀-arylalkyl, C₆- to C₁₀-aryl or —

[C(CN)₂]⁻

, —

[C(CN)COO—

C₁- to —

C₄-alkyl]⁻

or —

[C(COO—

C₁- to —

C₄-alkyl)₂]⁻

,

Z²⁰¹ is CH₂, C═

O or o-phenylene,

the rings C, D, E and F, independently of one another, may be substituted by up to 4 methyl radicals, or the rings C and D or the rings E and F, respectively, may be linked via a —

(CH₂)₄—

or —

CH═

CH—

CH═

CH—

bridge, and

X⁻

is an anion,

where another electrochromic substance of the formula (CC) or another electrochromic substance OX₂ or RED₁ may be attached via the bridge B.

4. Electrochromic device according to claim 2,

wherein

R²⁰¹ and R²⁰², independently of one another, are methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, benzyl, phenethyl, phenylpropyl, phenyl-butyl or phenyl,

Z²⁰¹ is CH₂, C═

O or o-phenylene,

the rings C and D or the rings E and F, respectively, may be linked via a —

CH═

CH—

CH═

CH—

bridge, and

X⁻

is an anion.

5. Electrochromic device according to claim 3, characterized in that the formula (CC) is part of one of the formulae

6. Electrochromic device of the formula (CCIII) according to claim 5,

in which

l, u and t are 1.

7. Electrochromic device according to one or more of claims 1 to 6, characterized in that it comprises

a) an electrochromic substance OX₂ of the formulae (CC) or (CCI) and additionally an electrochromic substance OX₂ of the formula (I) and an electrochromic substance RED₁ of the formula (XXVI) or an electrochromic substance OX₂—

B-RED₁, which comprises, as OX₂, a radical of the formula (I) and, as RED₁, a radical of the formula (XXVI), and optionally an electrochromic substance RED₁ of the formula (XXVI), or

b) an electrochromic substance of the formula (CCIII) and additionally an electrochromic substance OX₂ of the formula (I) and optionally an electrochromic substance RED₁ of the formula (XXVI) or an electrochromic substance OX₂—

B-RED₁, which comprises, as OX₂, a radical of the formula (I) and, as RED₁, a radical of the formula (XXVI), and optionally an electrochromic substance RED₁ of the formula (XXVI).

8. Electrochromic substance of one of the formulae (CC) to (CCIV),

in which the radicals are as defined in claims 1 to 6,

with the proviso that, in formula (CC),

R²⁰¹ and R²⁰² may not both be methyl, ethyl or benzyl when Z²⁰¹ is CH₂, and

R²⁰¹ and R²⁰² may not both be benzyl when Z²⁰¹ is o-phenylene, and

with the proviso that, in formula (CCI),

Z²⁰¹ is o-phenylene,

R²⁰¹ and R²⁰² together are a direct bond,

k is 1 and

B is o-phenylene or —

(CH₂)₃—

.

9. Electrochromic medium comprising at least one electrochromic substance of the formulae (CC) to (CCIV),

in which the radicals are as defined in claims 1 to 6.

10. Use of the electrochromic device according to one or more of claims 1 to 6 as a window or separating screen or sight protection screen or glazing or roof glazing or light filter or mirror or display device.