US 11,605,790 B2 · Monosubstituted diazabenzimidazole carbene metal complexes for use in organic light emitting diodes

Abstract

An organic electronic device, preferably an organic light-emitting diode (OLED), comprising at least one metal-carbene complex comprising one, two or three specific bidentate diazabenzimidazole carbene ligands; a light-emitting layer comprising said metal-carbene complex as emitter material, preferably in combination with at least one host material; the use of said metal-carbene complex in an OLED; an apparatus selected from the group consisting of stationary visual display units, mobile visual display units, illumination units, units in items of clothing, units in handbags, units in accessories, units in furniture and units in wallpaper comprising said organic electronic device, preferably said OLED, or said light-emitting layer; the metal-carbene complex comprising one, two or three specific bidentate diazabenzimidazole carbene ligands mentioned above and a process for the preparation of said metal-carbene complex.

An organic electronic device comprising at least one metal-carbene complex, wherein the metal is Ir or Pt, comprising one, two or three bidentate ligands of formula (I) and/or (I′)

wherein
R1 has the following meaning:
wherein:
m is 1;
˜ is the bonding site to the ligand of formula (I) or (I′);
and
the group R1 has one of the following definitions:
R6
R7
R8
13
iso-butyl
methyl
hydrogen
14
tert-butyl
methyl
hydrogen
18
iso-butyl
ethyl
hydrogen
19
tert-butyl
ethyl
hydrogen
20
iso-propyl
n-propyl
hydrogen
22
iso-butyl
n-propyl
hydrogen
23
tert-butyl
n-propyl
hydrogen
27
iso-propyl
methyl
methyl
29
iso-butyl
methyl
methyl
30
tert-butyl
methyl
methyl
33
iso-propyl
ethyl
ethyl
35
iso-butyl
ethyl
ethyl
36
tert-butyl
ethyl
ethyl
39
iso-propyl
ethyl
propyl
41
iso-butyl
ethyl
propyl
42
tert-butyl
ethyl
propyl
52
Tolyl
hydrogen
hydrogen
53
Xylyl
hydrogen
hydrogen
54
pyridyl
hydrogen
hydrogen
55
methylpyridyl
hydrogen
hydrogen
56
pyrimidyl
hydrogen
hydrogen
57
pyrazinyl
hydrogen
hydrogen
58
carbazolyl
hydrogen
hydrogen
59
dibenzofuranyl
hydrogen
hydrogen
60
dimethylfluorenyl
hydrogen
hydrogen
61
methylindonyl
hydrogen
hydrogen
62
—CH2-tolyl
hydrogen
hydrogen
63
—CH2-xylyl
hydrogen
hydrogen
64
—CH2-pyridyl
hydrogen
hydrogen
65
—CH2-pyrazinyl
hydrogen
hydrogen
66
—CH2-methylpyridinyl
hydrogen
hydrogen
67
—CH2-dibenzofuranyl
hydrogen
hydrogen
71
—CMe2-iso-butyl
hydrogen
hydrogen
72
cyclopentyl
hydrogen
hydrogen
73
cyclohexyl
hydrogen
hydrogen
74
adamantyl
hydrogen
hydrogen
75
—CH2-adamantyl
hydrogen
hydrogen
78
SiMe3
hydrogen
hydrogen
79
SiPh3
hydrogen
hydrogen
80
phenyl
methyl
methyl
81
tolyl
methyl
methyl
82
xylyl
methyl
methyl
83
pyridyl
methyl
methyl
84
methylpyridyl
methyl
methyl
85
pyrimidyl
methyl
methyl
86
pyrazinyl
methyl
methyl
87
carbazolyl
methyl
methyl
88
dibenzofuranyl
methyl
methyl
89
dimethylfluorenyl
methyl
methyl
90
methylindonyl
methyl
methyl
91
—CH2-tolyl
methyl
methyl
92
—CH2-xylyl
methyl
methyl
93
—CH2-pyridyl
methyl
methyl
94
—CH2-pyrazinyl
methyl
methyl
95
—CH2-methylpyridinyl
methyl
methyl
96
—CH2-dibenzofuranyl
methyl
methyl
100
—CMe2-iso-butyl
methyl
methyl
101
cyclopentyl
methyl
methyl
102
cyclohexyl
methyl
methyl
103
CF3
methyl
methyl
104
CF2CF3
methyl
methyl
105
SiMe3
methyl
methyl
106
SiPh3
methyl
methyl
A1 is CR2 or N;
A2 is CR3 or N;
A3 is CR4 or N;
A4 is CR5 or N;
A1′ is CR2′ or N;
A2′ is CR3′ or N;
A3′ is CR4′ or N;
A4′ is CR5′ or N;
R2, R3, R4, R5, R2′, R3′, R4′ and R5′
are each independently hydrogen;
deuterium;
a linear or branched, substituted or unsubstituted alkyl radical having 1 to 20 carbon atoms, optionally interrupted by at least one heteroatom, selected from O, S and N;
a substituted or unsubstituted cycloalkyl radical having a total of from 3 to 30 carbon atom;
a substituted or unsubstituted heterocyclo alkyl radical, interrupted by at least one heteroatom selected from O, S and N and having a total of from 3 to 30 carbon atoms and/or heteroatoms;
a substituted or unsubstituted aryl radical, having a total of from 6 to 30 carbon atoms;
a substituted or unsubstituted heteroaryl radical, having a total of from 5 to 30 carbon atoms and/or heteroatoms, selected from O, S and N;
or a group with donor or acceptor action;
or
R2 and R3, R3 and R4 or R4 and R5 or R2′ and R3′, R3′ and R4′ or R4′ and R5′ may form, independently of each other, together with the carbon atoms to which they are bonded, a saturated or unsaturated or aromatic, optionally substituted ring, which is optionally interrupted by at least one heteroatom, selected from O, S and N, has a total of from 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 heteroatom, selected from O, S and N, and having a total of from 5 to 18 carbon atoms and/or heteroatoms;
and
˜ in Formula (I) and Formula (I′) is the bonding site to the metal.

280 more elements

Monosubstituted diazabenzimidazole carbene metal complexes for use in organic light emitting diodes

Life of this patent

Monosubstituted diazabenzimidazole carbene metal complexes for use in organic light emitting diodes

Life of this patent

Abstract

Claims16