Metal complexes comprising azabenzimidazole carbene ligands and the use thereof in OLEDs

Patent metadata

Field	Value
Publication number	US-9315724-B2
Application number	US-201213494563-A
Country	US
Kind code	B2
Filing date	Jun 12, 2012
Priority date	Jun 14, 2011
Publication date	Apr 19, 2016
Grant date	Apr 19, 2016

Abstract

The present invention relates to metal-carbene complexes comprising a central atom selected from iridium and platinum, and specific azabenzimidazolocarbene ligands, to OLEDs (Organic Light Emitting Diode, OLED) 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.

First claim

The invention claimed is:

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

wherein:
M is Ir;
n is an integer selected from 1, 2 and 3, where the ligand(s):

are each bidentate ligands;

Y is NR 1 ;
R 1 is ethyl, isopropyl, tert-butyl, neopentyl, CF 3 , a substituted or unsubstituted cycloalkyl radical having 5 to 20 carbon atoms, or a substituted or unsubstituted aryl radical having 6 to 30 carbon atoms;
R 2 , R 3 , R 4 are each independently hydrogen, 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, group with donor or acceptor action selected from halogen radicals; CF 3 , CN and SiMe 3 , or
R 2 and R 3 or R 3 and R 4 form, together with the carbon atoms to which they are bonded, an optionally substituted unsaturated, saturated or aromatic ring which is optionally interrupted by at least one further heteroatom, has a total of 5 to 18 carbon atoms and/or heteroatoms and may optionally be fused to at least one further optionally substituted saturated or unsaturated or aromatic ring optionally interrupted by at least one further heteroatom and having a total of 5 to 18 carbon atoms and/or heteroatoms;
A 1 is CR 6 ;
A 2 is CR 7 ;
A 3 is CR 8 ;
A 4 is CR 9 ;
R 6 , R 7 , R 8 , R 9 are each independently hydrogen, a linear or branched alkyl radical optionally bearing at least one functional group, optionally interrupted by at least one heteroatom and having 1 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, group with donor or acceptor action selected from halogen radicals, CF 3 , CN and SiMe 3 , or
R 6 and R 7 , R 7 and R 8 , or R 8 and R 9 form, together with the carbon atoms to which they are bonded, a saturated, unsaturated or aromatic, optionally substituted ring which is optionally interrupted by at least one heteroatom, has a total of 5 to 18 carbon atoms and/or heteroatoms and may optionally be fused to at least one further optionally substituted saturated or unsaturated or aromatic ring optionally interrupted by at least one further heteroatom and having a total of 5 to 18 carbon atoms and/or heteroatoms;
p is 1;
K is an uncharged mono- or bidentate ligand;
L is a carbene ligand of formula (II):

a ligand of the formula (B):

picolinato,
salicylato,
8-hydroxyquinolato, or
a heterocyclic noncarbene ligand of formula (III):

A 9 is CR 12 or N;
A 10 is CR 13 or N;
R 11 is a 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 cycloalkyl radical optionally interrupted by at least one heteroatom, optionally bearing at least one functional group and having 3 to 20 carbon atoms, substituted or unsubstituted heterocycloalkyl radical optionally interrupted by at least one heteroatom, optionally bearing at least one functional group and having 3 to 20 carbon atoms and/or heteroatoms, 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;
R 12 , R 13 are each independently hydrogen, a 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 cycloalkyl radical optionally interrupted by at least one heteroatom, optionally bearing at least one functional group and having 3 to 20 carbon atoms, substituted or unsubstituted heterocycloalkyl radical optionally interrupted by at least one heteroatom, optionally bearing at least one functional group and having 3 to 20 carbon atoms and/or heteroatoms, 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, group with donor or acceptor action;
A 5 is CR 14 or N;
A 6 is CR 15 or N;
A 7 is CR 16 or N;
A 8 is CR 17 or N;
R 14 , R 15 , R 16 , R 17 are each independently hydrogen, a 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 cycloalkyl radical optionally interrupted by at least one heteroatom, optionally bearing at least one functional group and having 3 to 20 carbon atoms, substituted or unsubstituted heterocycloalkyl radical optionally interrupted by at least one heteroatom, optionally bearing at least one functional group and having 3 to 20 carbon atoms and/or heteroatoms, 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, group with donor or acceptor action, or
R 14 and R 15 , R 15 and R 16 or R 16 and R 17 form, together with the carbon atoms to which they are bonded, an unsaturated or aromatic, optionally substituted ring optionally interrupted by at least one heteroatom and having a total of 5 to 18 carbon atoms and/or heteroatoms, and/or
R 12 and R 13 form, together with A 9 and A 10 to which they are bonded, an unsaturated or aromatic, optionally substituted ring optionally interrupted by exactly one heteroatom or two adjacent heteroatoms and having a total of 5 to 18 ring atoms, and/or
if A 9 is CR 12 , R 12 and R 17 together form a saturated or unsaturated, linear or branched bridge optionally comprising heteroatoms, aromatic units, heteroaromatic units and/or functional groups and having a total of 1 to 30 carbon atoms and/or heteroatoms, to which is optionally fused a substituted or unsubstituted, five- to eight-membered ring comprising carbon atoms and/or heteroatoms;
q is 0 or 1;
R 51 is 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; substituted or unsubstituted heteroaryl radical having a total of 5 to 18 carbon atoms and/or heteroatoms;
R 52 is hydrogen, a linear or branched alkyl radical having 1 to 6 carbon atoms, substitut

Assignees

• Metz Stefan
• Fuchs Evelyn
• Dormann Korinna
• Molt Oliver
• Lennartz Christian
• Wagenblast Gerhard
• Geβner Thomas
• Schildknecht Christian
• Watanabe Soichi
• Basf Se

Inventors

• Metz Stefan
• Fuchs Evelyn
• Dormann Korinna
• Molt Oliver
• Lennartz Christian
• Wagenblast Gerhard
• Geβner Thomas
• Schildknecht Christian
• Watanabe Soichi

Classifications

• H01L51/0085

  Electricity · mapped topic

• C09K2211/1007

  Non-condensed systems · CPC title

• C09K2211/185

  of the platinum group, i.e. Os, Ir, Pt, Ru, Rh or Pd · CPC title

• C09K2211/1059

  containing three nitrogen atoms as heteroatoms · CPC title

• C09K2211/1029

  containing one nitrogen atom as the heteroatom · CPC title