METAL COMPLEXES COMPRISING DIAZABENZIMIDAZOLOCARBENE LIGANDS AND THE USE THEREOF IN OLEDS

• US 20130032766A1
• Filed: 12/13/2010
• Published: 02/07/2013
• Est. Priority Date: 12/14/2009
• Status: Active Grant

• Current Assignee: UDC Ireland Limited
• Original Assignee: BASF SE
• Inventors: Molt, Oliver, Lennartz, Christian, Wagenblast, Gerhard, Fuchs, Evelyn, Langer, Nicolle, Schildknecht, Christian, Dormann, Korinna, Watanabe, Soichi, Schaefer, Thomas, Wolleb, Heinz, Figueira Duarte, Teresa Marina, Murer, Peter, Metz, Stefan
• Granted Patent: US 9,487,548 B2
• Time in Patent Office: Days
• US Class Current: 252/519.2
• CPC Class Codes: C07D 307/91 Dibenzofurans; Hydrogenated dibenzofurans
• CPC Class Codes: C07D 405/14 containing three or more hetero rings
• CPC Class Codes: C07F 15/0033 Iridium compounds
• CPC Class Codes: C07F 15/0086 Platinum compounds
• CPC Class Codes: C07F 7/0816 said ring comprising Si as a ring atom
• CPC Class Codes: C09K 11/025 non-luminescent particle coatings or suspension media
• CPC Class Codes: C09K 11/06 containing organic luminescent materials
• CPC Class Codes: C09K 2211/1007 Non-condensed systems
• CPC Class Codes: C09K 2211/1044 containing two nitrogen atoms as heteroatoms
• CPC Class Codes: C09K 2211/1059 containing three nitrogen atoms as heteroatoms
• CPC Class Codes: C09K 2211/1088 containing oxygen as the only heteroatom
• CPC Class Codes: C09K 2211/185 of the platinum group, i.e. Os, Ir, Pt, Ru, Rh or Pd
• CPC Class Codes: H10K 2101/10 Triplet emission
• CPC Class Codes: H10K 50/11 characterised by the electroluminescent [EL] layers
• CPC Class Codes: H10K 50/125 specially adapted for multicolour light emission, e.g. for emitting white light
• CPC Class Codes: H10K 50/14 Carrier transporting layers
• CPC Class Codes: H10K 50/155 comprising dopants
• CPC Class Codes: H10K 50/16 Electron transporting layers
• CPC Class Codes: H10K 50/165 comprising dopants
• CPC Class Codes: H10K 50/18 Carrier blocking layers
• CPC Class Codes: H10K 85/30 : Coordination compounds
• CPC Class Codes: H10K 85/342 : comprising iridium
• CPC Class Codes: H10K 85/346 : comprising platinum
• CPC Class Codes: H10K 85/40 : Organosilicon compounds, e.g. TIPS pentacene
• CPC Class Codes: H10K 85/653 : comprising only oxygen as heteroatom
• CPC Class Codes: H10K 85/654 : comprising only nitrogen as heteroatom H10K85/652 takes precedence
• CPC Class Codes: H10K 85/6572 : comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole
• CPC Class Codes: H10K 85/6574 : comprising only oxygen in the heteroaromatic polycondensed ring system, e.g. cumarine dyes
• CPC Class Codes: Y02E 10/549 : Organic PV cells

Abstract

The present invention relates to metal-carbene complexes comprising a central atom selected from iridium and platinum, and diazabenzimidazolocarbene ligands, to organic light diodes which comprise such complexes, to light-emitting layers comprising at least one such metal-carbene complex, to a device selected from the group comprising illuminating elements, stationary visual display units and mobile visual display units comprising such an OLED and 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.

Claims

1. A metal-carbene complex of the general formula (I):

2. The metal-carbene complex according to claim 1, wherein:

M is Ir,

n is 1, 2 or 3,

Y is NR¹,

A², A³, A⁴, A⁵ are each independently N or C, where 2 A=nitrogen atoms and at least one carbon atom is present between two nitrogen atoms in the ring,

R¹ is a linear or branched alkyl radical having 1 to 6 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,

R², R³, R⁴, R⁵ are each, if A², A³, A⁴ and/or A⁵ is N, a free electron pair, or, if A², A³, A⁴ and/or A⁵ is C, each independently hydrogen, linear or branched alkyl radical having 1 to 6 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

R³ and R⁴ together with A³ and A⁴ form an optionally substituted, unsaturated ring optionally interrupted by at least one further heteroatom and having a total of 5 to 18 carbon atoms and/or heteroatoms,

R⁶, R⁷, R⁸, R⁹ are each independently hydrogen, linear or branched alkyl radical optionally interrupted by at least one heteroatom, optionally bearing at least one functional group and having 1 to 20 carbon atoms, substituted or unsubstituted aryl radical optionally interrupted by at least one heteroatom, optionally bearing at least one functional group and having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl radical optionally interrupted by at least one heteroatom, optionally bearing at least one functional group and having a total of 5 to 18 carbon atoms and/or heteroatoms, with a base skeleton selected from the group consisting of pyridyl, pyrimidyl, pyrazyl, triazolyl, pyrrole, furan, thiophene, pyrazole, triazole, oxazole and thiazole,

L is a monoanionic bidentate ligand,

m is 0, and

o is 0, 1 or 2.

3. The metal-carbene complex according to claim 1, wherein:

M is Ir,

n is 2 or 3,

Y is NR¹,

A², A³, A⁴, A⁵ A² and A⁵ are each N and A³ and A⁴ are each C

or

A² and A⁴ are each N and A³ and A⁵ are each C

or

A³ and A⁵ are each N and A² and A⁴ are each C,

R¹ is a linear or branched alkyl radical having 1 to 6 carbon atoms, substituted or unsubstituted phenyl radical, substituted or unsubstituted heteroaryl radical having a total of 6 to 18 carbon atoms and/or heteroatoms,

R², R³, R⁴, R⁵ are each, if A², A³, A⁴ and/or A⁵ is N, a free electron pair or, if A², A³, A⁴ and/or A⁵ is C, each independently hydrogen, linear or branched alkyl radical having 1 to 6 carbon atoms, substituted or unsubstituted phenyl radical,

or

R³ and R⁴ together with A³ and A⁴ form an optionally substituted, monounsaturated ring having a total of 5 to 7 carbon atoms,

R⁶, R⁷, R⁸, R⁹ are each independently hydrogen, linear or branched alkyl radical having 1 to 20 carbon atoms, o,o′

-dialkylated aryl radical having 6 to 30 carbon atoms,

L is a monoanionic bidentate ligand,

m is 0,

o is 0 or 1.

4. The metal-carbene complex of claim 1, wherein, in the general formula (I), L is a carbene ligand of the general formula (II):

5. The metal-carbene complex of claim 1, wherein L in the general formula (I) is a heterocyclic noncarbene ligand of the general formula (III):

6. A process for preparing the metal-carbene of claim 1, the process comprising contacting at least one compound comprising M with at least one ligand or ligand precursor.

7. The process according to claim 6, comprising contacting the at least one compound with at least one ligand precursor, wherein the ligand precursor is a Ag-carbene complex.

8. The process according to claim 6, comprising contacting the at least one compound with at least one ligand precursor, wherein the ligand precursor is a compound of the general formula (IV):

9. An organic electronic component, comprising at least one metal-carbene complex of claim 1.

10. The organic electronic component according to claim 9, which is an organic light-emitting diode (OLED), organic photovoltaic cell (OPV), organic field-effect transistor (OFET) or light-emitting electrochemical cell (LEEC).

11. A light-emitting layer, comprising at least one metal-carbene complex according to claim 1.

12. An OLED, comprising a light-emitting layer according to claim 11.

13. An OLED., comprising at least one metal-carbene complex according to claim 1, and at least one compound of the formula (X):

14. The OLED according to claim 13, comprising at least one compound of the formula (XI) or (XI*):

15. The OLED according to claim 14, wherein R⁷⁰ and/or R⁷¹ and/or R⁷² in the compounds of the general formula (XI) or (XI*) are aromatic units of the general formulae (XIi) and/or (XIi*):

16. The OLED according to claim 13, comprising an emission layer comprising the at least one metal-carbene complex, and at least one matrix material.

17. The OLED according to claim 12, comprising an electron-transporting layer comprising at least two different materials, of which at least one material is electron-conducting.

18. The OLED according to claim 17, wherein the electron-transporting layer comprises at least one phenanthroline derivative and/or pyridine derivative.

19. The OLED according to claim 17, wherein the electron-transporting layer comprises at least one phenanthroline derivative and/or pyridine derivative and at least one alkali metal hydroxyquinolate complex.

20. The OLED according to claim 17, wherein the electron-transporting layer comprises at least one phenanthroline derivative and/or pyridine derivative and 8-hydroxyquinolatolithium.

21. A device, comprising at least one OLED according to claim 12, wherein the device is at least one selected from the group consisting of a stationary visual display unit, a mobile visual display unit and an illumination unit.

22. An OLED, comprising the metal-carbene complex according to claim 1.

23. The OLED according to claim 22, wherein the metal-carbene complex is at least one selected from the group consisting of an emitter, a matrix material, a charge transport material and a charge blocker.