Back to results
US 6,806,989 B2Granted
Electrochromic device and novel electrochromic compounds
AssigneeBayer Aktiengesellschaft
InventorHorst Berneth
Life of this patent
Estimating the term…
Abstract
Asymmetrical compounds composed of two different heterocyclic and/or carbocyclic rings linked via a conjugated chain containing an uneven number of chain atoms are useful electrochromic compounds and can be used for producing electrochromic devices.
Claims16
An electrochromic device comprising:
- (a) a pair of glass plates or a pair of plastic plates or a pair of plastic films, wherein (A) both plates or both films are transparent and at least one plate has a side with a transparent electrically conductive coating that is optionally divisible into separate, individually contacted area segments or (B) (i) one plate or one film is transparent, (ii) the other plate or film is mirrored and (iii) at least one plate or at least one film has a transparent, electrically conductive coating that is optionally divisible into separate, individually contacted area segments and,
- (b) a sealing ring for joining together the plates or the films on the sides having an conductive coating, wherein the two plates or films and the sealing ring form a volume, and
- (c) an electrochromic medium for filling the volume, wherein the electrochromic medium includes at least one oxidizable electrochromic substance RED1 and at least one reducible electrochromic substance OX2, wherein the substance RED1 is an electrochromic compound of the formula (CC):
- wherein
- A is an aromatic or a quasi-aromatic, heterocyclic 5- or 6-membered ring in which X201 is located in the 2- or 4-position relative to the point of attachment,
- B is an aromatic or a quasi-aromatic, carbocyclic or heterocyclic 5- or 6-membered ring in which Y201 is located in the 2- or 4-position relative to the point of attachment,
- X201 is NR201, O or S,
- Y201 is NR202R203, OR204 or SR205,
- Z201 to Z203, independently of one another, are carbon or nitrogen,
- R201 to R205, independently of one another, are alkyl, alkenyl, cycloalkyl, aralkyl or aryl, and
- R202 to R205 may additionally be hydrogen,
- is an integer from 0 to 3, and
- Z201 to Z203 may form a bridge with one another or with the rings A and/or B,
- and/or the substance OX2 used is an electrochromic compound of the formula (CCl)
- wherein
- C is an aromatic or a quasi-aromatic, heterocyclic 5- or 6-membered ring in which X202 is located in the 2- or 4-position relative to the point of attachment,
- D is an aromatic or a quasi-aromatic, carbocyclic or heterocyclic 5- or 6-membered ring in which Y202 is located in the 2- or 4-position relative to the point of attachment, or
- is ═C(CN)2, ═C(CN)COOalkyl or ═C(COOalkyl)2,
- X202 is N+R206, O+ or S+,
- Y202 is NR207, O, S, N—CN or C(CN)2,
- Z204 to Z206, independently of one another, are carbon or nitrogen,
- R206 and R207, independently of one another, are alkyl, alkenyl, cycloalkyl, aralkyl or aryl,
- j is an integer from 0 to 3, and
- Z204 to Z206 may form a bridge with one another or with the rings C and/or D,
- wherein the rings A, B, C and D may carry further substituents.
22 more elements
An electrochromic compound of the formula (CC):
- A is an aromatic or a quasi-aromatic, heterocyclic 5- or 6-membered ring in which X201 is located in the 2- or 4-position relative to the point of attachment,
- B is an aromatic or a quasi-aromatic, carbocyclic or \ heterocyclic 5- or 6-membered ring in which Y201 is located in the 2- or 4-position relative to the point of attachment,
- X201 is NR201, O or S,
- Y201 is NR202R203, OR204 or SR205,
- Z201 to Z203, independently of one another, are carbon or nitrogen,
- R201 to R205, independently of one another, are alkyl, alkenyl, cycloalkyl, aralkyl or aryl, and
- R202 to R205 may additionally be hydrogen,
- i is an integer from 0 to 3, and
- Z201 to Z203 may form a bridge with one another or with the rings A and/or B,
- wherein
- A is not be a benzthiazoline radical when Z201—(Z202═Z203)i is N—N═CH or N and B is an N,N-disubstituted aniline radical,
- A is not be a dithiazoline radical when Z201—(Z202═Z203)i is N and B is an N,N-disubstituted aniline radical,
- Z201—(Z202═Z203)i is not be CH—N═N,
- or of the formula (CCl)
- wherein
- C is an aromatic or a quasi-aromatic, heterocyclic 5- or 6-membered ring in which X202 is located in the 2- or 4-position relative to the point of attachment,
- D is an aromatic or a quasi-aromatic, carbocyclic or heterocyclic 5- or 6-membered ring in which Y202 is located in the 2- or 4-position relative to the point of attachment, or
- is ═C(CN)2, ═C(CN)COOalkyl or ═C(COOalkyl)2,
- X202 is N+R206, O+ or S+,
- Y202 is NR207, O, S, N—CN or C(CN)2,
- Z204 to Z206, independently of one another, are carbon or nitrogen,
- R206 and R207, independently of one another, are alkyl, alkenyl, cycloalkyl, aralkyl or aryl,
- j is an integer from 0 to 3, and
- Z204 to Z206 may form a bridge with one another or with the rings C and/or D,
- wherein
- C is not be a pyridinium radical when Z4═(Z5—Z6)j is CH and D is an indane-1,3-dion-2-ylidene radical.
23 more elements
An electrochromic compound of the formula (L)
- Y—[—(—B—Z—)a—(—B—Y—)b—]c—B—Z (L),
- wherein
- Y and Z, independently of one another, are an OX2 or RED1 radical with the proviso that at least one Y is OX2 and at least one Z is RED1 or Y and Z are OX2,
- wherein
- OX2 is the radical of a reversibly electrochemically reducible redox system, and
- RED1 is the radical of a reversibly electrochemically oxidizable redox system,
- B is a bridging unit,
- c is an integer from 0 to 1000, and
- a and b, independently of one another, are integers from 0 to 100, wherein at least one OX2 corresponds to a radical of the formula (CCl) and/or at least one RED1 corresponds to a radical of the formula (CC).
6 more elements
An electrochromic medium comprising at least one electrochromic substance of the formulae (CC), (CCl) or (L), wherein formula (CC) is
- wherein
- A is an aromatic or a quasi-aromatic, heterocyclic 5- or 6-membered ring in which X201 is located in the 2- or 4-position relative to the point of attachment,
- B is an aromatic or a quasi-aromatic, carbocyclic or heterocyclic 5- or 6-membered ring in which Y201 is located in the 2- or 4-position relative to the point of attachment,
- X201 is NR201, O or S,
- Y201 is NR202R203, OR204 or SR205,
- Z201 to Z203, independently of one another, are carbon or nitrogen,
- R201 to R205, independently of one another, are alkyl, alkenyl, cycloalkyl, aralkyl or aryl, and
- R202 to R205 may additionally be hydrogen,
- i is an integer from 0 to 3, and
- Z201 to Z203 may form a bridge with one another or with the rings A and/or B,
- and/or the substance OX2 used is an electrochromic compound of wherein the formula (CCl) is:
- wherein
- C is an aromatic or a quasi-aromatic, heterocyclic 5- or 6-membered ring in which X202 is located in the 2- or 4-position relative to the point of attachment,
- D is an aromatic or a quasi-aromatic, carbocyclic or heterocyclic 5- or 6-membered ring in which Y202 is located in the 2- or 4-position relative to the point of attachment, or
- is ═C(CN)2, ═C(CN)COOalkyl or ═C(COOalkyl)2,
- X202 is N+R206, O+ or S+,
- Y202 is NR207, O, S, N—CN or C(CN)2,
- Z204 to Z206, independently of one another, are carbon or nitrogen,
- R206 and R207, independently of one another, are alkyl, alkenyl, cycloalkyl, aralkyl or aryl,
- j is an integer from 0 to 3, and
- Z204 to Z206 can form a bridge with one another or with the rings C and/or D,
- wherein
- C is not a pyridinium radical when Z4═(Z5—Z6)j is CH and D is an indane-1,3-dion-2-ylidene radical, and
- wherein formula (L) is
- Y—[—(—B—Z—)a—(—B—Y—)b—]c—B—Z (L),
- wherein Y and Z, independently of one another, are an OX2 or RED1 radical with the proviso that at least one Y is OX2 and at least one Z is RED1 or Y and Z are OX2,
- wherein OX2 is the radical of a reversibly electrochemically reducible redox system, and
- RED1 is the radical of a reversibly electrochemically oxidizable redox system,
- B is a bridging unit,
- c is an integer from 0 to 1000, and a and b, independently of one another, are integers from 0 to 100,
- wherein at least one OX2 corresponds to a radical of the formula (CCl) and/or at least one RED1 corresponds to a radical of the formula (CC).
28 more elements
Dependencies are inferred from the claim text.