Organic Electronics 14 (2013) 2596–2601

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Organic Electronics
journal homepage: www.elsevier.com/locate/orgel

Highly efficient phosphorescent organic light-emitting diodes

using a homoleptic iridium(III) complex as a sky-blue dopant
Jinyong Zhuang a,b, Wanfei Li b,d, Wenming Su b, Yuan Liu c, Qi Shen a,⇑, Liangsheng Liao c,⇑,
Ming Zhou b,d,⇑
a
Key Laboratory of Organic Synthesis of Jiangsu Province, Department of Chemistry and Chemical Engineering, Dushu Lake Campus, Soochow University, Suzhou,
Jiangsu 215123, PR China
b
Suzhou Institute of Nano-Tech and Nano-Bionics, Chinese Academy of Sciences, 398 Ruoshui Road, Suzhou Industrial Park, Suzhou, Jiangsu 215123, PR China
c
Jiangsu Key Laboratory for Carbon-Based Functional Materials & Devices, Institute of Functional Nano & Soft Materials (FUNSOM), Soochow University, Suzhou,
Jiangsu 215123, PR China
d
SunaTech Inc., Suzhou Industrial Park, Suzhou, Jiangsu 215123, PR China

a r t i c l e i n f o a b s t r a c t

Article history: Homoleptic triscyclometalated iridium(III) complex Ir(dbi)3 was used as a dopant for sky
Received 17 April 2013 blue phosphorescent organic light-emitting diodes (PHOLEDs). Its photophysical, thermal,
Received in revised form 22 June 2013 electrochemical properties as well as the device performances were investigated. Ir(dbi)3
Accepted 29 June 2013
exhibited high quantum yield of 0.52 in solution at room temperature. A maximum current
Available online 12 July 2013
efficiency and external quantum efficiency (EQE) of 61.5 cd A1 and 23.1% were obtained,
which are the highest ever reported for blue homoleptic iridium complexes. High efficien-
Keywords:
cies of 53.5 cd A1 and 20.1% EQE were achieved even at the luminance of 1000 cd m2.
Phosphorescent OLED
Homoleptic
Ó 2013 Elsevier B.V. All rights reserved.
Iridium(III) complex
Sky-blue
Highly efficient

1. Introduction ical sector as well, to which cyclometalated iridium (III)

Since the pioneering work of Tang and VanSlyke [1], the
organic light-emitting diodes (OLEDs) have gained indus-
trial acceptance and been successfully used for display
and lighting. To further advance the technological develop-
ment, exploiting novel phosphorescent material systems
remains a lasting endeavor after Baldo reported the high
efficiency energy transfer from both singlet and triplet
states [2]. Phosphorescent organic light-emitting diodes
(PHOLEDs) have become a research field and a technolog-
⇑ Corresponding authors. Address: Suzhou Institute of Nano-Tech and
Nano-Bionics, Chinese Academy of Sciences, 398 Ruoshui Road, Suzhou
Industrial Park, Suzhou, Jiangsu 215123, PR China. Tel.: +86 512
62872558; fax: +86 512 62872181 (M. Zhou), tel.: +86 512 65880306;
fax: +86 512 65880305 (Q. Shen), tel.: +86 512 65880945 (L. Liao).
E-mail addresses: qshen@suda.edu.cn (Q. Shen), lsliao@suda.edu.cn
(L. Liao), ming.zhou@sunatech.com (M. Zhou).
emitters have made predominant contribution [3–10].
Compared with the large number of red and green emitters
so far discovered and developed, the choices of blue
emitting systems have been almost solely based on
bis[(4,6-difluorophenyl)-pyridinate-N,C20 ]picolinate (FIrpic)
[11–15], although a few categories [16–25] of other mate-
rials have also been investigated. For more than ten years,
the blue emission systems have been a bottle neck for the
further development of PHOLED technology and its rapid
industrialization. As a benchmark material in research,
not only the emission of FIrpic is greenish blue, but also
the short lifetime does not match the red and green sys-
tems, leading to the unbalanced performance decay in
RGB-based devices. The short lifetime of FIrpic has been re-
cently associated with its ancillary ligand, picolinate,
which presumably decomposes in devices following an
acid-induced degradation [26] similar to that of acetylace-
tonate complexes [27].

1566-1199/$ - see front matter Ó 2013 Elsevier B.V. All rights reserved.
http://dx.doi.org/10.1016/j.orgel.2013.06.029
 J. Zhuang et al. / Organic Electronics 14 (2013) 2596–2601
Theoretically, homoleptic triscyclometalated iridium(III)
complexes have higher chemical stability [6] and longer
lifetime [28] than their heteroleptic biscyclometalated
counterparts with a labile or vulnerable ancillary ligand,
such as picolinate in FIrpic. Unfortunately, triscyclometa-
lating C^N ligand useful for blue emitters is very limited
and the blue emission systems incorporating triscyclo-
metalated iridium(III) dopants with high efficiencies are
rare (see Table S3 in Supplementary data). It was suggested
that while maintaining excellent color, an improved device
stability could be achieved from a series of homoleptic
iridium(III) complexes with three phenyl-imidazole-
derived C^N cyclometalating ligands. However, except
the structures of a number of biscyclomataled heteroleptic
iridium(III) complexes (with two phenyl-imidazole-
derived ligands and an ancillary ligand) [29–31], there is
little detailed materials properties and device performance
regarding tris(phenyl-imidazole) homoleptic iridium(III)
complexes available to the research community. In this
work, we report the properties of one of such triscyclo-
metalated iridium(III) dopants, fac-tris[1-(2,4-dii-
sopropyldibenzo[b,d]furan-3-yl)-2-phenyl-1H-imidazole]
iridium(III) (Ir(dbi)3 in Scheme 1) and our evaluation of the
OLED device performance.
2. Experimental
2.1. General information
1-(1,3-diisopropyldibenzo[b,d]furan-2-yl)-2-phenyl-
1H-imidazole (dbi) and tris(acetylacetonate)iridium (III)
(Ir(acac)3) were received from SunaTech Inc.. HAT-CN and
TmPyPB were received from Luminescence Technology
Corp. All reactants and solvents, unless otherwise stated,
were purchased from commercial sources and used as re-
ceived. Dichloromethane used in photophysical experi-
ments were of spectroscopic grade. 1H NMR and 13C NMR
spectra were measured on a 400 MHz Varian NMR spec-
trometer in CDCl3 with tetramethylsilane as an internal
standard. Mass spectra were measured on a Varian ProStar
LC240 (America). UV–vis absorption and PL spectra were
recorded on a Perkin–Elemer Lambda 750 and a HITACHI
F460 fluorescence spectrophotometer, respectively. The
quantum efficiency measurements were carried out at
room temperature in degassed acetonitrile solutions. Phos-
phorescence spectra were measured with an Edinburgh
Instruments FLS920 spectrometer. Thermogravimetric
analysis (TGA) was undertaken with a SII-EXSTAR 6000
TG/DTA 6200 thermobalance (SII Nano Technology Inc.,
Tokyo, Japan) under a nitrogen atmosphere by heating
the samples from 25 to 700 °C at a heating rate of
Scheme 1. Synthesis of the homoleptic blue emitter Ir(dbi)3.
2597
10 °C min1. Differential scanning calorimetry (DSC) was
performed on a SII Exstar 6000 (DSC 6220) instrument.
The samples were heated at a heating rate of 10 °C min1
from 25 to 400 °C under argon. Elemental analysis was car-
ried out using a EA1110 instrument (Carlo Erba Instru-
ments, Italy) Cyclic voltammetry (CV) was carried out in
a three-electrode electrochemical configuration with a
platinum working electrode, a platinum auxiliary electrode
and an Ag wire pseudo-reference electrode. The potential
was referred to the internal standard ferrocene/ferroce-
nium (Fc/Fc+) redox couple. The electrochemical cell was
loaded with nitrogen-purged DMF and tetrabutylammo-
nium hexafluorophosphate (TBAPF6) supporting electrolyte
in a nitrogen-filled glove box (oxygen and water con-
tents < 0.1 ppm) at room temperature. A PARSTAT 2263-2
Advanced Electrochemical System with PowerSUITE soft-
ware was used for electrochemical measurement and con-
trol. High performance liquid chromatography (HPLC) was
carried out using HPLC from Agilent Instrument.
2.2. Device fabrication and measurement
OLED devices were fabricated by sequentially
depositing organic layers and metal cathode layer using
thermal evaporation in one run under high vacuum
(4.5  104 Pa) onto an indium tin oxide (ITO) glass sub-
strate. Prior to use, the substrate was degreased with sol-
vents and cleaned in a UV–ozone chamber for 15 min
before it was loaded into the evaporation system. The ac-
tive device area was 3  3 mm2. The thickness of the
deposited layer and the evaporation speed of the individ-
ual materials were monitored with quartz crystal micro-
balance monitors. Electrical testing and optical
measurements were performed using devices encapsu-
lated in air with a glass lid. The EL spectra were measured
with a Spectra Scan PR655. The current–voltage (I–V) and
luminance–voltage (L–V) relations were characterized with
a computer controlled Keithley 2400 Sourcemeter.
3. Results and discussions
Fig. 1 shows the UV–vis absorption and photolumines-
cence (PL) features of both Ir(dbi)3 and FIrpic. As many other
cyclometalated iridium(III) complexes, Ir(dbi)3 exhibits a
metal-to-ligand charge-transfer (MLCT) absorption band
from 320 to 450 nm. The absorption of Ir(dbi)3 is much
stronger than FIrpic, which could be attributed to the strong
MLCT cause by the imidazole ligand [8]. Under an excitation
at 357 nm, Ir(dbi)3 emits light with a maximum at 475 nm
and a shoulder at 504 nm. The emission maximum is slightly
(3 nm) red-shifted compared with the PL maximum of
FIrpic. The solution quantum efficiency (Up) measured in
acetonitrile is 0.52, referred to fac-tris[2-phenylpyridina-
to]iridium(III) (Ir(ppy)3, 0.40 [32]).
Ir(dbi)3 was further characterized by the thermal analy-
sis and the cyclic voltammetry (see Supplementary data).
The thermal and electrochemical data were summarized
in Table 1. The decomposition temperature (Td: defined
as the temperature at that 5% weight loss occurs) of Ir(dbi)3
is 429 °C, compared with 344 °C [33] for FIrpic. The high Td
2598 J. Zhuang et al. / Organic Electronics 14 (2013) 2596–2601

Fig. 1. The UV–vis absorption (---) and PL spectra (—) of Ir(dbi)3 in comparison with FIrpic (both 1  105 M in acetonitrile) at room temperature. Excitation
wavelength: 357 nm. Inset: phosphorescence spectra of Ir(dbi)3 film at 77 K.

Table 1
Summary of properties of Ir(dbi)3 and FIrpic.

e@k (nm) (M1 cm1)a kem (nm)a,b Eg (eV)c HOMO (eV)d LUMO (eV)e ET (eV) Upf Tdg/Tdm (°C)
Ir(dbi)3 175025@225 103827@254, 95157@285, 16499@349 475 2.74 4.95 2.21 2.58 0.52 429/330
FIrpic 42513@253 4943@374 472 2.93 5.53 2.60 2.62h 0.63 344i
a 5
Measured in degassed CH3CN at 1  10 M.
b
Excitation at 357 nm.
c
Calculated from the absorption edge.
d
Calculated from the CV test relative to Fc/Fc+.
e
Calculated from the Eg and HOMO level.
f
Quantum efficiencies were measured in CH3CN, relative to Ir(ppy)3 = 0.40.
g
Corresponding to 5% weight loss.
h
Reported in Ref. [37].
i
Reported in Ref. [33].

Fig. 2. Device structure and chemical structures of the materials used in OLEDs.
 J. Zhuang et al. / Organic Electronics 14 (2013) 2596–2601 2599

Fig. 3. Luminance–current density of the devices with Ir(dbi)3 and FIrpic as dopants. Inset: current/power efficiencies–current density characteristics
(solid: current efficiency and open: power efficiency).

Fig. 4. EQE–current density characteristics of the devices with Ir(dbi)3 and FIrpic as dopants. Inset: EL spectra of the Ir(dbi)3-and FIrpic-based device.

could be attributed to its homoleptic structure as sup-

ported also by other triscyclometalated iridium(III) com-
plexes [6]. The melting temperature (Tm) was found to be
330 °C measured by DSC. As for the electrochemical prop-
erty, Ir(dbi)3 shows a reversible redox wave at 0.15 V vs.
Fc/Fc+, which is much lower than that of FIrpic (0.95 V).
While such a low redox potential is rare, comparable and
even lower values have been previously observed
from other homoleptic iridium(III) complex, such as mer-
tris(2-(p-tolyl)pyridinato,N,C20 )iridium(III) (mer-Ir(tpy)3,
0.18 V) [5], mer-tris(1-phenylpyrazolato,N,C20 )iridium(III)
(mer-Ir(ppz)3, 0.28 V) [5], tris(carbene) tris(phenyl-
methyl-benzimidazolyl) iridium(III) (mer-Ir(pmb)3, 0.0 eV,
calculated from HOMO level) [34] and bis(carbene)
complexes (Ir(mpmi)2(dmpypz), H2mpmiI = 1-(4-tolyl)-3-
methyl-imidazolium iodide, Hdmpypz = 3,5-dimethyl-2- Fig. 5. Luminance–time characteristics for devices under a constant
(1H-pyrazol-5-yl)pyridine, 0.30 eV) [35]. current with an initial luminance of 1000 cd m2.
 2600 J. Zhuang et al. / Organic Electronics 14 (2013) 2596–2601

Table 2
EL data of devices based on Ir(dbi)3 and FIrpic in comparison with some other blue emitters reported in literature.

Dopant CE PE EQE Voltage CE PE EQE CIE (x, y) Luminance Lifetime

Maximum @1000 cd m2 @1 mA cm2
Ir(dbi)3 61.5 43.7 23.1 5.6 53.5 30.1 20.1 0.19, 0.44 564 5.8
FIrpic 30.5 20.7 13.5 7.4 29.4 12.5 12.6 0.16, 0.36 314 0.1
Ir(dbfmi)3 [38] 28.6 35.9 18.6 4.3 9.4 6.3 6.2 0.15, 0.19a – –
FK306 [47] 29 30 17 4.2 21.5 16.1 12.7 0.16, 0.25a – –

CE: cd A1, PE: lm W1, EQE: %, voltage: V, luminance: cd m2, and lifetime: hours.
a
According to the reference.

Using Ir(dbi)3 as the dopant and mCP (N,N0 -dicarbazol- encapsulation condition, the big difference between the
elyl-3,5-benzene) as the host material, we have fabricated two devices does indicate a much higher stability of
devices with the architecture (see schematic design in Ir(dbi)3-based device relative to FIrpic-based device. With
Fig. 2) of ITO/HAT-CN (10 nm)/TAPC (45 nm)/mCP: Ir(dbi)3, a theoretically more stable homoleptic structure and a pro-
10 wt% (20 nm)/TmPyPB (40 nm)/Liq (2 nm)/Al (120 nm), ven higher thermal stability for Ir(dbi)3, the longer lifetime
where HAT-CN (1,4,5,8,9,11-hexaazatriphenylene hexacar- of Ir(dbi)3-based device is not a surprise. If we optimize the
bonitrile), TAPC (1,1-bis[(di-4-tolylamino)phenyl]cyclo- OLED structure and replace the hole transport material
hexane), TmPyPB (1,3,5-tri(m-pyrid-3-yl-phenyl)benzene) TAPC, the host material mCP and the electron transport
and Liq (8-hydroxyquinolinlato-lithium) are hole injection, material TmPyPB by other novel materials, the operational
hole transport, electron transport and electron injection lifetime of the device would be further increased. Table 2 is
materials, respectively. a summary of the overall performance comparison be-
The electroluminescence (EL) performance of the blue tween Ir(dbi)3-based device and FIrpic-based device.
emitter Ir(dbi)3 was compared with FIrpic using the same
device structure (Fig. 2). The luminance–current density
4. Conclusions
characteristics and EQE–current density characteristics
are shown in Figs. 3 and 4. As shown in Fig. 3, the lumi-
In summary, we have demonstrated a phosphorescent
nance of Ir(dbi)3-based device at the same current density
OLED device structure with a homoleptic cyclometalated
is much higher than that of FIrpic-based device. The lumi-
iridium(II) complex Ir(dbi)3 as a greenish blue dopant.
nance of Ir(dbi)3-based device at 0.2 and 1 mA cm2 is 123
Photophysical, electrochemical and thermal characteriza-
and 564 cd m2, respectively, which are much higher than
tion of the dopant material was performed. Compared with
the FIrpic-based device at the same condition (61 and
FIrpic, Ir(dbi)3 exhibited a much higher thermal stability
314 cd m2). The maximum current efficiency
and the OLED device doped with it also showed a much
(61.5 cd A1) and power efficiency (43.7 lm W1) were
longer lifetime in our preliminary assessment. Although
achieved from Ir(dbi)3-based device, which are two times
the CIE chromaticity coordinates indicate a little more
as high as those of FIrpic-based device (30.5 cd A1,
greenish for Ir(dbi)3-based devices than FIrpic-based
20.7 lm W1) under the same fabrication and testing con-
devices, the demonstrated current and power efficiencies
dition. A maximum external quantum efficiency (EQE) of
(maxima 61.5 cd A1 and 43.7 lm W1; and 53.5 cd A1
23.1% was achieved from the Ir(dbi)3-based device, com-
and 30.1 lm W1 at 1000 cd m2) are about twice as those
pared with 13.5% of the FIrpic-based device. Even at the
of the FIrpic-based devices and among the best in sky-blue
luminance of 1000 cd m2, 53.5 cd A1 and 20.1% were ob-
emitting OLED devices. The excellent properties of Ir(dbi)3
tained from the Ir(dbi)3-based device. To the best of our
warrant further studies of the dopant material and its ana-
knowledge, such an performance is the best so far achieved
logues. Novel device structures incorporating Ir(dbi)3 could
from homoleptic iridium(III) sky blue phosphorescent
open another avenue to developing blue emitting PHOLED
emitters [20,36–39] and is one of the best in all blue PHOL-
and white OLED systems.
EDs reported in literature [22,24,39–47].
As for the device stability, the lifetimes of the devices
Acknowledgements
incorporated with Ir(dbi)3 were much longer than that of
FIrpic-based devices under the same experimental condi-
The authors thank the National Natural Science Founda-
tions. The preliminary lifetime evaluation was performed
tion of China under the Projects (Nos. 20902066,
with the devices that were encapsulated with a glass lid
21072218, 11004218 and 21161160446) and the Hun-
in atmosphere. The lifetime (T50 in hour) is defined as the
dred-Talent Program of the Chinese Academy of Sciences
time when the luminance of an OLED device is reduced
for financial support.
to the half of its initial value during the test at a constant
current. In our experiments, an initial luminance was cho-
sen as 1000 cd m2. As demonstrated in luminance–time Appendix A. Supplementary material
profile in Fig. 5, the luminance of Ir(dbi)3-based device de-
cayed much slower than FIrpic-based device, the T50 being Supplementary data associated with this article can be
5.8 and 0.1 h., respectively, under our experimental condi- found, in the online version, at http://dx.doi.org/10.1016/
tion. Although the lifetimes were assessed under a simple j.orgel.2013.06.029.
 J. Zhuang et al. / Organic Electronics 14 (2013) 2596–2601 2601

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