A series of new functional
pyridine-appended pyrene derivatives,
viz., 2,6-diphenyl-4-(pyren-1-yl)pyridine (
Py-03
), 2,6-bis(4-methoxyphenyl)-4-(pyren-1-yl)pyridine
(
Py-MeO
), 4-(pyren-1-yl)-2,6-di-
p
-tolylpyridine
(
Py-Me
), and 2,6-bis(4-bromophenyl)-4-(pyren-1-yl)pyridine
(
Py-Br
) were designed, developed, and studied as the
hole-transporting materials (HTMs) for organic light-emitting diode
(OLED) application. The crystal structures of two molecules revealed
to have a large dihedral angle between the pyrene and pyridine units,
indicating poor π-electronic communication between them due
to ineffective orbital overlap across the pyrene–pyridine systems
as the two p-orbitals of pivotal atoms are twisted at 66.80°
and 68.75° angles to each other in
Py-03
and
Py-Me
, respectively. The influence of variedly functionalized
pyridine units on the electro-optical properties and device performance
of the present integrated system for OLED application was investigated.
All of the materials have suitable HOMO values (5.6 eV) for hole injection
by closely matching the HOMOs of indium tin oxide (ITO) and the light-emitting
layer. All of the synthesized molecules have suitable triplet energies,
glass transition temperatures, and melting temperatures, which are
highly desirable for good HTMs. The pyrene–pyridine-based devices
demonstrated stable performance with low-efficiency roll-off. The
device with
Py-Br
as HTM showed a maximum luminance of
17300 cd/m
2
with a maximum current efficiency of 22.4 cd/A
and an EQE of 9% at 3500 cd/m
2
with 7% roll-off from 1000
to 10 000 cd/m
2
. Also, the devices with
Py-Me
and
Py-03
showed performance roll-up while moving from
1000 to 10 000 cd/m
2
.