Dinuclear metal complexes comprising carbene ligands and the use thereof in OLEDs
The present invention relates to dinuclear metal-carbene complexes comprising a central atom selected from platinum and palladium, where both metal atoms are cyclometalated to the same aromatic group, to OLEDs (Organic Light-Emitting Diodes) which comprise such complexes, to a device selected from the group consisting of illuminating elements, stationary visual display units and mobile visual display units comprising such an OLED, to the use of such a metal-carbene complex in OLEDs, for example as emitter, matrix material, charge transport material and/or charge or exciton blocker.
1. A metal-carbene complex of formula
or
wherein
M is Pd or Pt,
m is an integer selected from 0 or 1,
R 1 and R 1 ′ are each independently a linear or branched alkyl radical optionally interrupted by a heteroatom, optionally bearing a functional group and having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl radical optionally interrupted by a heteroatom, optionally bearing a functional group and having 3 to 20 carbon atoms, substituted or unsubstituted aryl radical, optionally bearing a functional group and having 6 to 30 carbon atoms, or substituted or unsubstituted heteroaryl radical optionally interrupted by a heteroatom, optionally bearing a functional group and having a total of 5 to 18 carbon atoms and/or heteroatoms;
R 2 , R 2 ′, R 3 and R 3 ′ are each independently hydrogen, a linear or branched alkyl radical optionally interrupted by a heteroatom, optionally bearing a functional group and having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl radical optionally interrupted by a heteroatom, optionally bearing a functional group and having 3 to 20 carbon atoms, substituted or unsubstituted aryl radical optionally interrupted by a heteroatom, optionally bearing a functional group and having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl radical optionally interrupted by a heteroatom, optionally bearing a functional group and having a total of 5 to 18 carbon atoms and/or heteroatoms, or a group with donor or acceptor action, or
R 1 and R 2 and/or R 1 ′ and R 2 ′ together with the atoms to which they are bonded form an optionally substituted, saturated or unsaturated or aromatic ring optionally interrupted by a further heteroatom and having a total of 5 to 18 carbon atoms and/or heteroatoms, and may optionally be fused to a further optionally substituted saturated or unsaturated or aromatic ring optionally interrupted by a further heteroatom and having a total of 5 to 18 carbon atoms and/or heteroatoms;
K is a neutral monodentate ligand, and
L is a monoanionic ligand, which can be mono- or bidentate.
2. The metal-carbene complex according to claim 1 , wherein
m is 0; and
L is a monoanionic bidentate ligand.
3. The metal-carbene complex according to claim 2 , wherein
L is selected from the group consisting of picolinato, salicylato, 8-hydroxyquinolato, and ligands of formula (A)
wherein
R 4 and R 4 ′ are in each case independently a linear or branched alkyl radical having 1 to 6 carbons atoms optionally bearing a functional group; substituted or unsubstituted cycloalkyl radical having 3 to 20 carbon atoms, substituted or unsubstituted aryl radical having 6 to 20 carbon atoms; or substituted or unsubstituted heteroaryl radical having a total of 5 to 18 carbon atoms and/or heteroatoms, and
R 5 is hydrogen, a linear or branched alkyl radical having 1 to 6 carbon atoms, or a substituted or unsubstituted aryl radical having 6 to 20 carbon atoms.
4. An organic electronic device comprising a metal-carbene complex according to claim 1 .
5. An apparatus selected from the group consisting of stationary visual display units, mobile visual display units; illumination units, keyboards, items of clothing, furniture, and wallpaper, the apparatus comprising the organic electronic device according to claim 4 .
6. The organic electronic device according to claim 4 , wherein the organic electronic component is selected from the group consisting of organic light-emitting diodes (OLEDs), organic photovoltaic cells (OPVs), organic field-effect transistors (OFETs) and light-emitting electrochemical cells (LEECs).
7. The organic electronic component according to claim 6 , wherein the organic electronic component is an OLED comprising a light-emitting layer comprising the metal-carbene complex.
8. A light-emitting layer comprising a metal-carbene complex according to claim 1 .
9. The light-emitting layer according to claim 8 , comprising the metal-carbene complex and a host material.
10. The metal-carbene complex according to claim 1 , wherein the complex is suitable for electrophotographic photoreceptors, photoelectric converters, organic solar cells (organic photovoltaics), switching elements, organic light emitting field effect transistors (OLEFETs), image sensors, dye lasers and organic light emitting devices.
11. The metal-carbene complex according to claim 10 , wherein the metal-carbene complex is configured in organic light emitting devices as charge transport material, charge blocker material, or matrix material.
12. A metal-carbene complex of formula
or
wherein
R 1 and R 1 ′ are each independently a linear or branched alkyl radical having 1 to 6 carbon atoms, substituted or unsubstituted cycloalkyl radical having 3 to 20 carbon atoms, substituted or unsubstituted aryl radical having 6 to 30 carbon atoms, or substituted or unsubstituted heteroaryl radical having a total of 5 to 18 carbon atoms and/or heteroatoms,
R 2 , R 2 ′, R 3 and R 3 ′ are each independently hydrogen, a linear or branched alkyl radical having 1 to 6 carbon atoms, substituted or unsubstituted cycloalkyl radical having 3 to 20 carbon atoms, substituted or unsubstituted aryl radical having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl radical having a total of 5 to 18 carbon atoms and/or heteroatoms, or a group with donor or acceptor action selected from halogen radicals; or
R 1 and R 2 and/or R 1 ′ and R 2 ′ form, together with the atoms to which they are bonded, an optionally substituted unsaturated, saturated or aromatic ring which is optionally interrupted by a further heteroatom, has a total of 5 to 18 carbon atoms and/or heteroatoms and may optionally be fused to a further optionally substituted saturated or unsaturated or aromatic ring optionally interrupted by a further heteroatom and having a total of 5 to 18 carbon atoms and/or heteroatoms, and
R 4 and R 4 ′ are in each case independently a linear or branched alkyl radical having 1 to 6 carbons atoms; substituted or unsubstituted aryl radical having 6 to 20 carbon atoms; or substituted or unsubstituted heteroaryl radical having a total of 5 to 18 carbon atoms and/or heteroatoms.
13. The metal-carbene complex according to claim 12 , wherein
R 1 is a linear or branched alkyl radical having 1 to 6 carbon atoms, substituted or unsubstituted cycloalkyl radical having 3 to 12 carbon atoms, or substituted or unsubstituted aryl radical having 6 to 15 carbon atoms,
R 2 and R 3 are each independently hydrogen, a linear or branched alkyl radical having 1 to 6 carbon atoms, substituted or unsubstituted aryl radical having 6 to 18 carbon atoms, or a group with donor or acceptor action selected from halogen radicals; or
R 1 and R 2 form, together with the atoms to which they are bonded, an optionally substituted unsaturated, saturated or aromatic ring which is optionally interrupted by a further heteroatom, has a total of 5 to 18 carbon atoms and/or heteroatoms, and
R 4 and R 4 ′ are in each case independently a linear or branched alkyl radical having 1 to 6 carbons atoms; or a substituted or unsubstituted aryl radical having 6 to 15 carbon atoms.
14. A process for preparing the metal-carbene complex according to claim 1 , comprising contacting a compound comprising M with a compound of formula
or
wherein
R 1 , R 1′ , R 2 , R 2′ , R 3′ and R 3 are each as defined according to claim 1 for the compounds of formula (I) or (II), and
X is F, Cl, Br, I, PF 6 , or BF 4 .