Novel electrochromic compositions based on diketopyrrolopyrroles
First Claim
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1. A composition containing(a) at least one 1,4-diketopyrrolo[3,4-c]pyrrole of the formula I, II, IIa, III or IV ##STR7## and (b) an auxiliary redox system which comprises sodium ferrocyanide, potassium ferrocyanide, calcium ferrocyanide, magnesium ferrocyanide, ammonium ferrocyanide or (NH3)2 Fe(SO4)2.6H2 O in combination with at least one conductive salt (c) from salts wherein the cation is selected from Li+, Na+, K+ and N+ (Cn H2n+1)4, where n is 1, 2, 3 or 4 and the anion is selected from Cl-, Br-, I-, CIO4-, BF4-, SCN-, CF3 SO3-, H2 PO2-, HPO32-, H2 PO4- and HCO3- ;
- where, in the formulae I, II and IIa, the groups R, independently of one another are --H, halogen, C1 -C4 alkyl, C1 -C4 alkoxy, C1 -C4 mercaptoalkyl, --CH, --CF3 or phenyl, R2 is --H or R1, and R3 is --H or a group of the formula --(CH2)p --R1, p is an integer from 1 to 6, and R1 is a group of the formula --CO2 L, --SO3 L, --PO3 L or --N+ (R10)(R11)(R12)X-- in which X is a halogen ion, (SO4)2-, (SO3 OCH3)- or (SO2 OC2 H5)- and L is --H, a group of the formula M+n /n or +NH(R10)(R11)(R12) where M is a monovalent, divalent or trivalent metal cation, n is the number 1, 2 or 3, and R10, R11 R12, independently of one another, are --H, C1 -C18 alkyl, C7 -C12 phenylalkyl, C5 -C6 cycloalkyl, or phenyl or naphthyl which is unsubstituted or substituted by halogen, C1 -C4 alkyl or C1 -C4 alkoxy, or R10 and R11, together with the nitrogen atom to which they are bonded , form a 5-6-membered heterocyclic radical which is pyrrolidino, morpholino or piperidino;
or R10, R11 and R12, together with the nitrogen atom to which they are bonded, form a 5-6-membered aromatic heterocyclic radical which is a quaternized pyrrolyl, pyridyl, picolyl, pyrazinyl, quinolyl or isoquinolyl group;
in the formula III, R4 and R5, independently of one another, are unsubstituted or halogen-, C1 -C4 alkyl- or C1 -C4 alkoxy-substituted naphthyl, phenyl or pyridyl, which in turn can be substituted by one or two halogen atoms, one or two C1 -C4 alkyl or C1 -C4 alkoxy groups, furthermore by C1 -C4 alkylmercapto, --CN, CF3, --CCl3, --CONH2, C2 -C5 alkoxycarbonyl or unsubstituted or halogen-, CH3 - or OCH3 -substituted phenyl, phenoxy, thiophenoxy or N-phenylcarbamoyl, and R6 and R.sub. 7, independently of one another, are C1 -C12 alkyl, C1 -C12 alkoxy, C1 -C12 alkylmercapto, C1 -C12 alkyl-C2 -C5 alkoxycarbonyl, C1 -C12 alkyl-C1 -C4 -N-alkylcarbamoyl or unsubstituted or halogen-, C1 -C4 alkyl-, C1 -C4 alkoxy-, C1 -C4 alkylmercapto-, CN- or CF3 -substituted phenyl, benzyl or benzoyl, and in the formula IV, R8 and R9, independently of one another, are C1 -C8 alkyl, C3 -C6 cycloalkyl, C7 -C12 phenylalkyl, which may be substituted in the phenyl radical by halogen, C1 -C4 alkyl, C1 -C4 alkoxy, C1 -C4 alkylmercapto, --CN, --CF3, --CH3, --CONH2 or phenyl, or R8 and R9 are furthermore unsubstituted or halogen-, C1 -C4 alkyl- or C1 -C4 alkoxy-substituted naphthyl or unsubstituted or halogen-, C1 -C4 alkyl-, C1 -C4 alkoxy-, C1 -C4 alkylmarcapto-, --CN, --CF3, --CCl3, --CONH2 or phenyl-substituted phenyl, or are pyridyl.
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Abstract
Compositions containing
(a) at least one 1,4-diketopyrrolo[3,4-c]pyrrole of the formula I, II, IIa, III or IV ##STR1## and (b) an auxiliary redox system from the ferrocyanide, ferrocene or ammonium iron(II) sulfate series in combination with at least one conductive salt (c), where, in the formula I,
R and R2 are, for example, --H and R1 is --SO3 Na,
in the formulae II and IIa, R and R3 are, for example, --H, R1 is --SO3 H and p is 3,
in the formula III, R4 and R5 are, for example, phenyl and R6 and R7 are, for example, methyl, and
in the formula IV R8 and R9 are, for example, phenyl,
are suitable as electrochromic materials in display systems.
32 Citations
6 Claims
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1. A composition containing
(a) at least one 1,4-diketopyrrolo[3,4-c]pyrrole of the formula I, II, IIa, III or IV ##STR7## and (b) an auxiliary redox system which comprises sodium ferrocyanide, potassium ferrocyanide, calcium ferrocyanide, magnesium ferrocyanide, ammonium ferrocyanide or (NH3)2 Fe(SO4)2.6H2 O in combination with at least one conductive salt (c) from salts wherein the cation is selected from Li+, Na+, K+ and N+ (Cn H2n+1)4, where n is 1, 2, 3 or 4 and the anion is selected from Cl-, Br-, I-, CIO4-, BF4-, SCN-, CF3 SO3-, H2 PO2-, HPO32-, H2 PO4- and HCO3- ; - where, in the formulae I, II and IIa, the groups R, independently of one another are --H, halogen, C1 -C4 alkyl, C1 -C4 alkoxy, C1 -C4 mercaptoalkyl, --CH, --CF3 or phenyl, R2 is --H or R1, and R3 is --H or a group of the formula --(CH2)p --R1, p is an integer from 1 to 6, and R1 is a group of the formula --CO2 L, --SO3 L, --PO3 L or --N+ (R10)(R11)(R12)X-- in which X is a halogen ion, (SO4)2-, (SO3 OCH3)- or (SO2 OC2 H5)- and L is --H, a group of the formula M+n /n or +NH(R10)(R11)(R12) where M is a monovalent, divalent or trivalent metal cation, n is the number 1, 2 or 3, and R10, R11 R12, independently of one another, are --H, C1 -C18 alkyl, C7 -C12 phenylalkyl, C5 -C6 cycloalkyl, or phenyl or naphthyl which is unsubstituted or substituted by halogen, C1 -C4 alkyl or C1 -C4 alkoxy, or R10 and R11, together with the nitrogen atom to which they are bonded , form a 5-6-membered heterocyclic radical which is pyrrolidino, morpholino or piperidino;
or R10, R11 and R12, together with the nitrogen atom to which they are bonded, form a 5-6-membered aromatic heterocyclic radical which is a quaternized pyrrolyl, pyridyl, picolyl, pyrazinyl, quinolyl or isoquinolyl group;
in the formula III, R4 and R5, independently of one another, are unsubstituted or halogen-, C1 -C4 alkyl- or C1 -C4 alkoxy-substituted naphthyl, phenyl or pyridyl, which in turn can be substituted by one or two halogen atoms, one or two C1 -C4 alkyl or C1 -C4 alkoxy groups, furthermore by C1 -C4 alkylmercapto, --CN, CF3, --CCl3, --CONH2, C2 -C5 alkoxycarbonyl or unsubstituted or halogen-, CH3 - or OCH3 -substituted phenyl, phenoxy, thiophenoxy or N-phenylcarbamoyl, and R6 and R.sub. 7, independently of one another, are C1 -C12 alkyl, C1 -C12 alkoxy, C1 -C12 alkylmercapto, C1 -C12 alkyl-C2 -C5 alkoxycarbonyl, C1 -C12 alkyl-C1 -C4 -N-alkylcarbamoyl or unsubstituted or halogen-, C1 -C4 alkyl-, C1 -C4 alkoxy-, C1 -C4 alkylmercapto-, CN- or CF3 -substituted phenyl, benzyl or benzoyl, and in the formula IV, R8 and R9, independently of one another, are C1 -C8 alkyl, C3 -C6 cycloalkyl, C7 -C12 phenylalkyl, which may be substituted in the phenyl radical by halogen, C1 -C4 alkyl, C1 -C4 alkoxy, C1 -C4 alkylmercapto, --CN, --CF3, --CH3, --CONH2 or phenyl, or R8 and R9 are furthermore unsubstituted or halogen-, C1 -C4 alkyl- or C1 -C4 alkoxy-substituted naphthyl or unsubstituted or halogen-, C1 -C4 alkyl-, C1 -C4 alkoxy-, C1 -C4 alkylmarcapto-, --CN, --CF3, --CCl3, --CONH2 or phenyl-substituted phenyl, or are pyridyl. - View Dependent Claims (2, 3, 4, 5, 6)
- where, in the formulae I, II and IIa, the groups R, independently of one another are --H, halogen, C1 -C4 alkyl, C1 -C4 alkoxy, C1 -C4 mercaptoalkyl, --CH, --CF3 or phenyl, R2 is --H or R1, and R3 is --H or a group of the formula --(CH2)p --R1, p is an integer from 1 to 6, and R1 is a group of the formula --CO2 L, --SO3 L, --PO3 L or --N+ (R10)(R11)(R12)X-- in which X is a halogen ion, (SO4)2-, (SO3 OCH3)- or (SO2 OC2 H5)- and L is --H, a group of the formula M+n /n or +NH(R10)(R11)(R12) where M is a monovalent, divalent or trivalent metal cation, n is the number 1, 2 or 3, and R10, R11 R12, independently of one another, are --H, C1 -C18 alkyl, C7 -C12 phenylalkyl, C5 -C6 cycloalkyl, or phenyl or naphthyl which is unsubstituted or substituted by halogen, C1 -C4 alkyl or C1 -C4 alkoxy, or R10 and R11, together with the nitrogen atom to which they are bonded , form a 5-6-membered heterocyclic radical which is pyrrolidino, morpholino or piperidino;
Specification
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Current AssigneeCiba-Geigy Corporation (Novartis Ag)
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Original AssigneeCiba-Geigy Corporation (Novartis Ag)
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InventorsMizuguchi, Jin, Rochat, Alain C.
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Primary Examiner(s)Springer, David B.
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Application NumberUS07/945,075Time in Patent Office560 DaysField of Search548/452, 503/202, 503/218, 106/21 A, 106/21 DUS Class Current106/31.64CPC Class CodesC09K 9/02 Organic tenebrescent materials
