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US 8,618,317 B2Granted
Organic electroluminescence device
AssigneeMerck Patent GmbH
InventorsPhilipp Stoessel, Dominik Joosten, Esther Breuning, Hartmut Yersin, Uwe Monkowius
Life of this patent
Estimating the term…
Abstract
The present invention relates to organic electroluminescence devices containing metal complexes having the formula (1) and metal complexes for use in organic electroluminescence devices.
Claims17
Organic electroluminescent device comprising at least one compound of the formula (1):
- where the following applies to the symbols and indices used:
- M1, M2 are on each occurrence, identically or differently, a metal selected from the group consisting of Pt, Pd, Ni, Ir, Rh, Mo, W, Re, Ru or Os;
- X is on each occurrence, identically or differently, P, As, Sb or Bi;
- Y is on each occurrence, identically or differently, C(R9)2, Si(R9)2, B(R9), N(R9), P(R9), O, S, Se, C(═O), C(═S), C(═NR9) or C(═C(R9)2);
- L1 is on each occurrence, identically or differently, a monodentate ligand or a bidentate ligand which coordinates to one of the metal atoms M1 or M2;
- L1 here may also be linked to one of the groups R1 to R8;
- L2 is on each occurrence, identically or differently, a bidentate ligand which simultaneously coordinates to both metal atoms M1 and M2;
- R1 to R8 are on each occurrence, identically or differently, F, Cl, Br, I, N(R10)2, CN, Si(R10)3, C(═O)R10, P(R10)2, a straight-chain alkyl, alkoxy or thioalkoxy group having 1 to 40 C atoms or a straight-chain alkenyl or alkynyl group having 2 to 40 C atoms or a branched or cyclic alkyl, alkenyl, alkynyl, alkoxy or thioalkoxy group having 3 to 40 C atoms, each of which may be substituted by one or more radicals R10, where one or more non-adjacent CH2 groups which are not bonded directly to X may be replaced by R10C═CR10, C≡C, Si(R10)2, Ge(R10)2, Sn(R10)2, C═O, C═S, C═Se, C═NR10, P(═O)(R10), SO, SO2, NR10, O, S or CONR10 and where one or more H atoms may be replaced by D, F, Cl, Br, I, CN or NO2, or an aromatic or heteroaromatic ring system having 5 to 60 aromatic ring atoms, each of which may be substituted by one or more radicals R10, or an aralkyl or heteroaralkyl group having 5 to 40 aromatic ring atoms, each of which may be substituted by one or more radicals R10, or an aryloxy or heteroaryloxy group having 5 to 40 aromatic ring atoms, which may be substituted by one or more radicals R10, or a diarylamino group, diheteroarylamino group or arylheteroarylamino group having 10 to 40 aromatic ring atoms, which may be substituted by one or more radicals R10;
- R1 and R2, R3 and R4, R5 and R6 and/or R7 and R8 here may also form a mono- or polycyclic, aliphatic, aromatic and/or benzo-fused ring system with one another;
- in addition, one or more radicals R1 to R8 may be linked to one or more ligands L1 or L2 and thus form a polydentate ligand;
- R9 is on each occurrence, identically or differently, H, D, F, Cl, Br, I, N(R10)2, CN, NO2, Si(R10)3, B(OR10)2, C(═O)R10, P(═O)(R10)2, S(═O)R10, S(═O)2R10, OSO2R10, a straight-chain alkyl, alkoxy or thioalkoxy group having 1 to 40 C atoms or a straight-chain alkenyl or alkynyl group having 2 to 40 C atoms or a branched or cyclic alkyl, alkenyl, alkynyl, alkoxy or thioalkoxy group having 3 to 40 C atoms, each of which may be substituted by one or more radicals R10, where one or more non-adjacent CH2 groups may be replaced by R10C═CR10, C≡C, Si(R10)2, Ge(R10)2, Sn(R10)2, C═O, C═S, C═Se, C═NR10, P(═O)(R10), SO, SO2, NR10, O, S or CONR10 and where one or more H atoms may be replaced by D, F, Cl, Br, I, CN or NO2, or an aromatic or heteroaromatic ring system having 5 to 60 aromatic ring atoms, each of which may be substituted by one or more radicals R10, or an aralkyl or heteroaralkyl group having 5 to 40 aromatic ring atoms, each of which may be substituted by one or more radicals R10, or an aryloxy or heteroaryloxy group having 5 to 40 aromatic ring atoms, which may be substituted by one or more radicals R10, or a diarylamino group, diheteroarylamino group or arylheteroarylamino group having 10 to 40 aromatic ring atoms, which may be substituted by one or more radicals R10;
- two radicals R9 here which are bonded to the same C or Si atom may also form a mono- or polycyclic, aliphatic, aromatic and/or benzo-fused ring system with one another;
- R10 is on each occurrence, identically or differently, H, D, F, Cl, Br, I, N(R11)2, CN, NO2, Si(R11)3, B(OR11)2, C(═O)R11, P(═O)(R11)2, S(═O)R11, S(═O)2R11, OSO2R11, a straight-chain alkyl, alkoxy or thioalkoxy group having 1 to 20 C atoms or a straight-chain alkenyl or alkynyl group having 2 to 20 C atoms or a branched or cyclic alkyl, alkenyl, alkynyl, alkoxy or thioalkoxy group having 3 to 20 C atoms, each of which may be substituted by one or more radicals R11, where one or more non-adjacent CH2 groups may be replaced by R11C═CR11, C≡C, Si(R11)2, Ge(R11)2, Sn(R11)2, C═O, C═S, C═Se, C═NR11, P(═O)(R11), SO, SO2, NR11, O, S or CONR11 and where one or more H atoms may be replaced by D, F, Cl, Br, I, CN or NO2, or an aromatic or heteroaromatic ring system having 5 to 60 aromatic ring atoms, each of which may be substituted by one or more radicals R11, or an aryloxy or heteroaryloxy group having 5 to 40 aromatic ring atoms, which may be substituted by one or more radicals R11, or a diarylamino group, diheteroarylamino group or arylheteroarylamino group having 10 to 40 aromatic ring atoms, which may be substituted by one or more radicals R11;
- two or more adjacent radicals R11 here may form a mono- or polycyclic, aliphatic or aromatic ring system with one another;
- R11 is on each occurrence, identically or differently, H, D, F or an aliphatic, aromatic and/or heteroaromatic hydrocarbon radical having 1 to 20 C atoms, in which, in addition, one or more H atoms may be replaced by F;
- two or more substituents R11 here may also form a mono- or polycyclic, aliphatic or aromatic ring system with one another;
- m, n are on each occurrence, identically or differently, 0, 1, 2 or 3;
- p is 0, 1, 2 or 3;
- with the proviso that the indices m, n and p are selected so that the coordination number on each of the metals M1 and M2 is four or five.
16 more elements
Dependencies are inferred from the claim text.