1-Phenyl-3-(1-phenyl-1-(pyridin-2-yl)ethyl)isoquinoline
(H
2
MeL) has been prepared by Pd(
N
-XantPhos)-catalyzed
“
deprotonative cross-coupling processes
”
to synthesize new phosphorescent red iridium(III) emitters (601–732
nm), including the carbonyl derivative Ir(κ
4
-
cis
-
C
,
C
′-
cis
-
N
,
N
′-MeL)Cl(CO)
and the acetylacetonate compound Ir(κ
4
-
cis
-
C
,
C
′-
cis
-
N
,
N
′-MeL)(acac). The tetradentate
6e-donor ligand (6tt′) of these complexes is formed by two
different bidentate units, namely, an orthometalated 2-phenylisoquinoline
and an orthometalated 2-benzylpyridine. The link between the bidentate
units reduces the number of possible stereoisomers of the structures
[6tt′ + 3b] (3b = bidentate 3e-donor ligand), with respect
to a [3b + 3b′ + 3b″] emitter containing three free
bidentate units, and it permits a noticeable stereocontrol. Thus,
the isomers
fac
-Ir(κ
4
-
cis
-
C
,
C
′-
cis
-
N
,
N
′-MeL){κ
2
-
C
,
N
-(C
6
H
4
-py)},
mer
-Ir(κ
4
-
cis
-
C
,
C
′-
cis
-
N
,
N
′-MeL){κ
2
-
C
,
N
-(C
6
H
3
R-py)}, and
mer
-Ir(κ
4
-
trans
-
C
,
C
′-
cis
-
N
,
N
′-MeL){κ
2
-
C
,
N
-(C
6
HR-py)} (R =
H, Me) have also been selectively obtained. The new emitters display
short lifetimes (0.7–4.6 μs) and quantum yields in a
doped poly(methyl methacrylate) film at 5 wt % and 2-methyltetrahydrofuran
at room temperature between 0.08 and 0.58. The acetylacetonate complex
Ir(κ
4
-
cis
-
C
,
C
′-
cis
-
N
,
N
′-MeL)(acac) has been used as a dopant for a red
PhOLED device with an electroluminescence λ
max
of
672 nm and an external quantum efficiency of 3.4% at 10 mA/cm
2
.