Metal complexes comprising diazabenzimidazolocarbene ligands and the use thereof in OLEDs

Patent metadata

Field	Value
Publication number	US-9487548-B2
Application number	US-201013516117-A
Country	US
Kind code	B2
Filing date	Dec 13, 2010
Priority date	Dec 14, 2009
Publication date	Nov 8, 2016
Grant date	Nov 8, 2016

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.

First claim

The invention claimed is:

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

wherein
M is Ir or Pt,
n is an integer 1, 2 or 3,
Y is NR 1 , O, S or C(R 10 ) 2 ,
A 2 and A 5 are each N,
A 3 and A 4 are each C,
R 1 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, 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 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 2 and R 5 are each an electron pair,
R 3 and R 4 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, 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 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,
R 6 , R 7 , R 8 , R 9 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, cycloalkyl radical optionally interrupted by at least one heteroatom, optionally bearing at least one functional group and having 3 to 20 carbon atoms, cycloheteroalkyl 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 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, group with donor or acceptor action, at least one selected from the group consisting of a halogen radical, a silyl radical, a siloxy radical, an alkoxy radical, an aryloxy radical, a carbonyl radical, an ester radical, CH 2 F, CHF 2 , CF 3 , CN, a thio group and SCN,
or
R 6 and R 7 , R 7 and R 8 or R 8 and R 9 , together with the carbon atoms to which they are bonded, form a saturated, 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,

R 10 is independently 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, 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 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,
K is an uncharged mono- or bidentate ligand,
L is a mono- or dianionic ligand,
m is 0, 1 or 2, where, when m is 2, the K ligands may be the same or different, and
o is 0, 1 or 2, where, when o is 2, the L ligands may be the same or different.

2. The metal-carbene complex according to claim 1 , wherein
M is Ir,
n is 1, 2 or 3,
Y is NR 1 ,
R 1 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,
R 6 , R 7 , R 8 , R 9 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
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 NR 1 ,
R 1 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,
R 6 , R 7 , R 8 , R 9 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):

wherein
A 6 , A 7 are each independently C 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, cycloalkyl radical optionally interrupted by at least one heteroatom, optionally bearing at least one functional group and having 3 to 20 carbon atoms, cycloheteroalkyl 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 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, when A is N, a free electron pair, or, when A is C, 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 carton atoms, cycloalkyl radical optionally interrupted by at least one heteroatom, optionally bearing at least one functional group and having 3 to 20 carbon atoms, cycloheteroalkyl radical optionally interrupted

Assignees

• Molt Oliver
• Lennartz Christian
• Wagenblast Gerhard
• Fuchs Evelyn
• Langer Nicolle
• Schildknecht Christian
• Dormann Korinna
• Watanabe Soichi
• Schaefer Thomas
• Wolleb Heinz
• Figueira Duarte Teresa Marina
• Metz Stefan
• Murer Peter
• Udc Ireland Ltd

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
• Metz Stefan
• Murer Peter

Classifications

• C07F7/0816

  said ring comprising Si as a ring atom · CPC title

• C09K2211/1007

  Non-condensed systems · CPC title

• C07F15/0033 Primary

  Iridium compounds · CPC title

• C09K11/06 Primary

  containing organic luminescent materials · CPC title

• C09K2211/1044

  containing two nitrogen atoms as heteroatoms · CPC title