Organic dyes comprising a hydrazone moiety and their use in dye-sensitized solar cells

A compound represented by formula (I):

• wherein
• R100 and R200 are each independently hydrogen, C1-C10-alkyl which in case of C2-alkyl may be interrupted by one and in case of C3-C10-alkyl by one or two nonadjacent oxygen atoms, C5-C7-cycloalkyl, aryl, aryl-C1-C10-alkyl or aryloxy-C1-C10-alkyl,
• D is an m-valent donor moiety which comprises at least one carbon-carbon or carbon-heteroatom double bond and/or at least one unfused or fused carbo- or heterocyclic ring,
• A is an acceptor moiety which comprises at least one carbon-carbon or carbon-heteroatom double bond and/or at least one unfused or fused carbo- or heterocyclic ring,
• m is 1, 2 or 3,
• the donor moiety D and the acceptor moiety A are π-conjugated to one another,
• when m=1 the donor moiety D is selected from the group consisting of:
• R110, R120 and R130 independently hydrogen, halogen, hydroxyl, C1-C10-alkyl which in case of C2-alkyl may be interrupted by one and in case of C3-C10-alkyl by one or two nonadjacent oxygen atoms, C5-C7-cycloalkyl, C1-C10-alkoxy, C1-C10-alkylamino, di(C1-C10-alkyl)amino, C1-C10-alkylamino- or di(C1-C10-alkyl)aminosulfonylamino, C1-C10-alkylsulfonylamino, aryl, aryl-C1-C10-alkyl, aryloxy-C1-C10-alkyl or an —NHCOR170 or —NHCOOR170 radical,
• R140, R150 and R160 are each independently hydrogen, C1-C10-alkyl which in case of C2-alkyl may be interrupted by one and in case of C3-C10-alkyl by one or two nonadjacent oxygen atoms, C5-C7-cycloalkyl, aryl aryl-C1-C10-alkyl, aryloxy-C1-C10-alkyl or in case R140 and R160 or R150 and R160 are bonded to adjacent carbon atoms these pairs of groups may—together with the carbon atoms to which they are bonded—form a five- or six-membered ring in which one CH2 group may be replaced by an oxygen atom,
• R170 is aryl, aryl-C1-C10-alkyl, aryloxy-C1-C10-alkyl or C1-C10-alkyl which in case of C2-alkyl may be interrupted by one and in case of C3-C10-alkyl by one or two nonadjacent oxygen atoms and in case of two moities for m=2 may vary independently of each other,
• R210, R220, R230 and R240 are each independently aryl, aryl-C1-C10-alkyl, aryloxy-C1-C10-alkyl, C1-C10-alkyl which in case of C2-alkyl may be interrupted by one and in case of C3-C10-alkyl by one or two nonadjacent oxygen atoms, C5-C10-cycloalkyl, or R210 and R220 and/or R230 and R240 form, together with the nitrogen atom to which they are bonded, a five- or six-membered ring in which one CH2 group not adjacent to the nitrogen atom may be replaced by an oxygen atom, or in case NR210R220 and R110 are bonded to adjacent carbon atoms, R110 and R210 or R110 and R220—together with the nitrogen atom of the moiety NR210R220 and the carbon atom to which the moieties NR210R220 and R110 are bonded—form a five- or six-membered ring in which one CH2 group not adjacent to the nitrogen atom may be replaced by an oxygen atom and which five- or six-membered ring may be fused to another five- or six-membered saturated or unsaturated ring,
• R250 and R260 are each independently C1-C10-alkyl which in case of C2-alkyl may be interrupted by one and in case of C3-C10-alkyl by one or two nonadjacent oxygen atoms, C5-C7-cycloalkyl, aryl, aryl-C1-C10-alkyl or aryloxy-C1-C10-alkyl,
• Z is O or S,
• when m=2 the donor moiety D is selected from the group consisting of:
• wherein R170 is defined above and in case of two moieties may vary independently of each other,
• when m=3 the donor moiety D is selected from the group consisting of:
• wherein R170 is defined above,
• A is represented by formula (Ia):
• A* represents a moiety selected from the group consisting of:
• * indicates the position which the double bond of the group of formula (Ia) is bonded to,
• R310 and R320 are each independently hydrogen, C1-C10-alkyl which in case of C2-alkyl may be interrupted by one and in case of C3-C10-alkyl by one or two nonadjacent oxygen atoms, or C5-C7-cycloalkyl,
• R330 is hydrogen, C1-C10-alkyl which in case of C2-alkyl may be interrupted by one and in case of C3-C10-alkyl by one or two nonadjacent oxygen atoms, partly fluorinated C1-C10-alkyl, perfluorinated C1-C10-alkyl, C5-C7-cycloalkyl, aryl, aryl-C1-C10-alkyl or aryloxy-C1-C10-alkyl,
• R340 is hydrogen, NO2, CN, COR350, COOR350, SO2R350 or SO3R350,
• R350 is aryl, aryl-C1-C10-alkyl, aryloxy-C1-C10-alkyl or C1-C10-alkyl which in case of C2-alkyl may be interrupted by one and in case of C3-C10-alkyl by one or two nonadjacent oxygen atoms,
• R410 is hydrogen, C1-C10-alkyl which in case of C2-alkyl may be interrupted by one and in case of C3-C10-alkyl by one or two nonadjacent oxygen atoms and which may be mono- or polysubstituted by hydroxyl, mercapto, halogen, cyano, nitro, —COOM and/or —COOR420, C5-C7-cycloalkyl, aryl, aryl-C1-C10-alkyl, aryloxy-C1-C10-alkyl, or an —NHCOR420 or —N(COR420)2 radical where the two R420 in the latter may be the same or different,
• X is independently CH or N,
• Y is O, C(CN)2, C(CN)(COOM) or C(CN)(COOR420),
• M is alkali metal cation or [NR420]4+, and
• R420 is hydrogen, aryl, aryl-C1-C10-alkyl, aryloxy-C1-C10-alkyl or C1-C10-alkyl which in case of C2-alkyl may be interrupted by one and in case of C3-C10-alkyl by one or two nonadjacent oxygen atoms.