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Use Of Transition Metal Carbene Complexes In Organic Light-Emitting Diodes (Oleds)

  • US 20080018221A1
  • Filed: 11/23/2005
  • Published: 01/24/2008
  • Est. Priority Date: 11/25/2004
  • Status: Abandoned Application
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1. An uncharged transition metal-carbene complex of the general formula I which is suitable for use in organic light-emitting diodes, where the variables are each defined as follows:

  • M is a metal atom selected from the group consisting of Co, Rh, Ir, Nb, Pd, Pt, Fe, Ru, Os, Cr, Mo, W, Mn, Re, Cu, Ag and Au in any oxidation state possible for the particular metal atom;

    L is a mono- or dianionic ligand which may be mono- or bidentate;

    K is an uncharged mono- or bidentate ligand selected from the group consisting of phosphines;

    phosphonates and derivatives thereof;

    arsenates and derivatives thereof;

    phosphites;

    CO;

    pyridines;

    nitriles, monoolefins and conjugated dienes which form a π

    -complex with M;

    n is the number of carbene ligands, where n is at least 1 and the carbene ligands in the complex of formula I, when n>

    1, may be the same or different;

    m is the number of ligands L, where m may be 0 or ≧

    1 and the ligands L, when m>

    1, may be the same or different;

    q is the number of ligands K, where q may be 0 or ≧

    1 and the ligands K, when q>

    1, may be the same or different, where the sum of n+m+q depends upon the oxidation state and coordination number of the metal atom m and upon the denticity and the charge of the ligands, with the condition that n is at least 1;

    Do is a donor atom selected from the group consisting of N, O and S;

    r is 1 when Do is N and O when Do is O or S;

    Y1, Y2 are each independently hydrogen, alkyl, aryl, heteroaryl or alkenyl;

    or Y1 and Y2, together with the carbon atoms to which they are bonded, form a six-membered aromatic ring which may comprise one or two nitrogen atoms, and is optionally fused to a further ring which is optionally fused and optionally comprises heteroatoms;

    Y3 is hydrogen or alkyl;

    or Y3 and Y2, together with the donor atom Do and the carbon atom to which Y2 is bonded, form a five- or six-membered ring which, apart from the donor atom Do, may also comprise a further heteroatom selected from the group consisting of N, O and S;

    A is a bridge having three or four atoms, of which one or two atoms may be heteroatoms and the remaining atoms are carbon atoms, so that the group  

    forms a five- or six-membered heteroaromatic ring or benzene ring, each of which is optionally substituted by substituents selected from the group consisting of alkyl, alkyloxy, alkylthio, aryl, aryloxy, arylthio, halogen, CN, CHO, alkylcarbonyl, arylcarbonyl, carboxyl, alkyloxycarbonyl, aryloxycarbonyl, hydroxysulfonyl, alkyloxysulfonyl, aryloxysulfonyl, NO2 and NO, and optionally fused with a further ring which is optionally fused and optionally comprises heteroatoms, where Y1, together with a group selected from chemical single bond, C(Y4)2, C(O), O, S, S(O), SO2 and NY5, may optionally form a two-membered bridge B to that carbon atom or heteroatom of the bridge A which is in the α

    -position to the carbon atom which is bonded to the nitrogen atom of the carbene unit of the carbene ligand; and

    Y4, Y5 are each independently hydrogen, alkyl, aryl or heteroaryl, and the two Y4 groups in the C(Y4)2 bridge may be varied independently of one another.

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