DINUCLEAR PLATINUM-CARBENE COMPLEXES AND THE USE THEREOF IN OLEDS

• US 20120199823A1
• Filed: 10/13/2010
• Published: 08/09/2012
• Est. Priority Date: 10/14/2009
• Status: Active Grant

• Current Assignee: UDC Ireland Limited (Universal Display Corporation)
• Original Assignee: BASF SE
• Inventors: Molt, Oliver, Lennartz, Christian, Wagenblast, Gerhard, Strassner, Thomas, Unger, Yvonne
• Granted Patent: US 9,108,998 B2
• Time in Patent Office: Days
• US Class Current: 257/40
• CPC Class Codes: C07F 15/0086 Platinum compounds
• CPC Class Codes: C09K 11/06 containing organic luminescent materials
• CPC Class Codes: C09K 2211/1044 containing two nitrogen atoms as heteroatoms
• CPC Class Codes: C09K 2211/1048 with oxygen
• CPC Class Codes: C09K 2211/1059 containing three nitrogen atoms as heteroatoms
• CPC Class Codes: C09K 2211/185 of the platinum group, i.e. Os, Ir, Pt, Ru, Rh or Pd
• CPC Class Codes: H05B 33/14 characterised by the chemical or physical composition or the arrangement of the electroluminescent material , or by the simultaneous addition of the electroluminescent material in or onto the light source
• CPC Class Codes: H10K 2101/10 Triplet emission
• CPC Class Codes: H10K 50/11 characterised by the electroluminescent [EL] layers
• CPC Class Codes: H10K 85/346 comprising platinum
• CPC Class Codes: H10K 85/361 Polynuclear complexes, i.e. complexes comprising two or more metal centers
• CPC Class Codes: Y02E 10/549 Organic PV cells
• CPC Class Codes: Y02P 70/50 Manufacturing or production processes characterised by the final manufactured product

Abstract

The present invention relates to dinuclear Pt-carbene complexes comprising carbene ligands and pyrazole bridges, to a process for preparing the dinuclear Pt-carbene complexes by contacting suitable Pt compounds with the corresponding ligands or ligand precursors and/or pyrazole or corresponding pyrazole derivatives, to organic electronic components comprising at least one such dinuclear Pt-carbene complex, to an OLED comprising at least one such dinuclear Pt-carbene complex, to a light-emitting layer comprising at least one such dinuclear Pt-carbene complex, to an OLED comprising such a light-emitting layer, to a device selected from the group consisting of stationary visual display units, mobile visual display units and illumination means, comprising such an OLED, and to the use of an inventive dinuclear Pt-carbene complex in OLEDs.

Claims

1. A dinuclear Pt-carbene complex of formula (Ia) or (Ib) or an isomer thereof:

2. The dinuclear Pt-carbene complex of claim 1,

wherein each R¹ and R³ is independently hydrogen or a linear or branched alkyl radical having from 1 to 4 carbon atoms,

R² is hydrogen,

each R⁴ is independently a linear or branched alkyl radical having from 1 to 4 carbon atoms;

a substituted or unsubstituted aryl radical having 6 carbon atoms;

or a substituted or unsubstituted heteroaryl radical having a total of 5 carbon atoms and heteroatoms,

each R⁵ and R⁶, if an adjacent A is N, is a free electron pair,

each R⁵ and R⁶, if an adjacent A is C, is independently hydrogen;

a linear or branched alkyl radical having from 1 to 4 carbon atoms;

a substituted or unsubstituted aryl radical having 6 carbon atoms;

or a substituted or unsubstituted heteroaryl radical having a total of 5 carbon atoms and heteroatoms,

R⁵ and R⁶ optionally form an aromatic ring optionally interrupted by a heteroatom, having a total of from 5 to 10 carbon atoms and heteroatoms, and

each R⁷, R⁸, R⁹, and R¹⁰ is independently hydrogen, with the proviso that R⁷ and R⁸ optionally instead form an optionally substituted unsaturated or aromatic ring, optionally interrupted by a heteroatom, having a total of from 5 to 12 carbon atoms and heteroatoms.

3. The dinuclear Pt-carbene complex of claim 1 of any of formulae (Ia), (Ib), (Ic), (Id), (Ie), and (If), or an isomer thereof:

4. A process for preparing the dinuclear Pt-carbene complex of claim 1, comprising:

contacting a Pt compound with a corresponding ligands ligand, a corresponding ligand precursor, a pyrazole corresponding pyrazole derivative, or a combination thereof.

5. An organic electronic component comprising the dinuclear Pt-carbene complex of claim 1.

6. The organic electronic component of claim 5,

wherein the organic electronic component is an organic light-emitting diode (OLED), an organic photovoltaic cell (OPV), an organic field-effect transistor (OFET), or a light-emitting electrochemical cell (LEEC).

7. A light-emitting layer comprising the dinuclear Pt-carbene complex of claim 1.

8. An organic light-emitting diode (OLED) comprising the light-emitting layer to of claim 7.

9. A device comprising the organic electronic component of claim 6,

wherein the organic electronic component is an OLED, and

the device is selected from the group consisting of a stationary visual display unit, a mobile visual display unit, and an illumination device.

12. An OLED, comprising:

an emitter, a matrix material, a charge transport material, or a charge blocker, comprising the dinuclear Pt-carbene complex of claim 1.

13. A device, comprising the OLED of claim 8,

wherein the device is selected from the group consisting of a stationary visual display unit, a mobile visual display unit, and an illumination device.

14. The dinuclear Pt-carbene complex of claim 1, wherein an R⁶ and an R⁷ form a phenyl ring.

15. The process of claim 4, comprising:

contacting the Pt compound with a corresponding ligand precursor of formula (III);

16. The process of claim 15, wherein X⁻

is chloride, bromide, iodide, BF₄⁻

, or PF₆⁻

.

17. The process of claim 16, wherein X⁻

is iodide.

18. The process of claim 17, wherein the corresponding ligand precursor is of formula (IIIa) or (IIIb):

19. The process of claim 4, comprising:

contacting the Pt compound with a pyrazole or corresponding pyrazole derivative of formula (IV1) or (IV2);

20. The process of claim 19, wherein the pyrazole or corresponding pyrazole derivative is any of compounds (IVa), (IVb), (IVc), (IVd), (IVe), and (IVf):

10-11. -11. (canceled)