High performance full color OLEDs based on a class of molecules with dual carrier transport channels and small singlet-triplet splitting

Article abstract of DOI:10.1039/c5cc03492b

Two deep blue emitting materials PPI-PPITPA and PPI-PPIPCz with dual carrier transport properties and small singlet-triplet splitting features are designed and synthesized. PPI-PPITPA and PPI-PPIPCz were used not only as non-doped emitting layers to fabri

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High Performance Full Color OLEDs based on a
Class of Molecules with Dual Carrier Transport
Channels and Small Singlet-Triplet Splitting
Chenglong Li, Shipan Wang, Weiping Chen, Jinbei Wei, Guochun Yang,
Kaiqi Ye, Yu Liu,* and Yue Wang*
Cite this: DOI: 10.1039/x0xx00000x
Received 00th January 2015,
Accepted 00th January 2015
DOI: 10.1039/x0xx00000x
www.rsc.org/
Two deep blue emitting materials PPI-PPITPA and PPI-PPIPCz
with dual carrier transport property and small singlet-triplet splitting
feature are designed and synthesized. PPI-PPITPA and PPI-
PPIPCz not only were used as non-doped emitting layer to fabricate
highly efficient deep blue OLEDs, but also as hosts to construct high
performance green, yellow and red phosphorescent OLEDs.
Organic light-emitting devices (OLEDs) are of current interest
from both scientific and practical points of view due to their
applications in the next generation full-color flat-panel displays and
solid-state lighting sources.[1] Generally, fine quality full-color
displays or white color lighting sources are constructed by rational
combination of high performance deep blue (B), green (G), yellow
(Y) and red (R) emitters together with different host materials.[2]
Figure 1. Molecular strucutres of PPI-PPITPA and PPI-PPIPCz
.
performance non-doped blue electroluminescent materials are
usually not suitable hosts for phosphorescent OLEDs (PhOLEDs)
due to their low ET and poor carrier transport property.[3] On the
other hand, the efficient hosts for G, Y and R phosphors often
displayed low efficiency when they were used as emitters in blue
color OLEDs.[4] So far, it is still a challenge to achieve highly
efficient full color OLEDs based on a deep blue emitting material.
To gain the multi-functional organic materials, which can be used
not only as emitters to fabricate highly efficient deep blue OLEDs,
but also as hosts to construct highly efficient G, Y and R OLEDs,
we proposed the molecular design and synthesis strategy as
following: (i) the molecules are supposed to have hole transport
moiety (donor) and electron transport moiety (acceptor) with high
photoluminescent (PL) quantum yield (ΦPL) in solid state; (ii) the
electron transport moieties and the hole transport moieties should be
able to separately assemble together to form electron and hole
transport channels, respectively, in solid state; (iii) to obtain deep
blue emission, the donor-acceptor (D-A) molecule should have
relatively weak charge transfer property since strong D-A structure
Therefore, achieving high performance R, Y,
G and B
electroluminescence (EL) based on simple material system with an
aim to minimize the manufacture cost of materials and simplify the
fabrication process is an important issue for OLED applications. In
principle, a deep blue emitting material with balanced carrier
transport characteristic and relatively high triplet energy (ET) may be
employed as an efficient host for G, Y and R phosphorescent
emitters, simultaneously. The high ET enables G, Y and R phosphors
to harvest the triplet energy of blue emitter. However, the high
State Key Laboratory of Supramolecular Structure and Materials, College of
Chemistry, Jilin University, Changchun 130012, P. R. China. E-mails:
yuliu@jlu.edu.cn (Y. Liu); yuewang@jlu.edu.cn (Y. Wang); Fax: +86-431-
85193421; Tel: +86-431-85168484 .
†
Electronic Supplementary Information (ESI) available: Synthetic
procedures and characterization data; DFT calculation result of PPI-
PPIPCz, CV curves, TGA, DSC, Energy level diagram and CCDC
1058058; See DOI: 10.1039/c000000x/
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can induce red shifted emission; (iv) the singlet-triplet splitting revealing that this molecule should have good electron and hole
(△EST) should be quite small to ensure the triplet excited state energy transport abilities. Both of the two compounds exhibit excellent
is high enough to excite G phosphorescent dopant. In this thermal stability as evidenced by their high decomposition
communication, we report two organic molecules (PPI-PPITPA and temperatures (corresponding to 5% weight loss) of 568 C for PPI-
PPI-PPIPCz) composed of two phenyl-phenanthroimidazol (PPI) PPITPA and 524 C for PPI-PPIPCz (Figure S5). The glass-
and one triphenylamine (TPA) or phenyl-carbazole (PCz) groups transition temperatures (Tg) are as high as 187 C for PPI-PPITPA
(Figure 1). Using PPI-PPITPA and PPI-PPIPCz as non-doped and 193 C for PPI-PPIPCz (Figure S6). The distinguished thermal
deep blue emitters and hosts for G, Y and R phosphorescent dopants, properties of the two compounds are favourable to form uniform thin
highly efficient full color OLEDs are fabricated.
films upon thermal evaporation, which are advantageous for
PPI-PPITPA and PPI-PPIPCz are synthesized through a simple application in OLEDs.
procedure (Scheme S1) and fully characterized by NMR, mass
The photophysical properties of PPI-PPITPA and PPI-PPIPCz
spectra, and element analyses (see Supporting Information). The were analyzed by UV-vis and PL measurements (Figure 3 and
PPI-PPITPA molecule displays a V-type geometry feature (Figure Table S1). In dilute CH2Cl2 solution, the two compounds exhibit
S1) as demonstrated by single-crystal X-ray analysis. The intense violet to deep blue emission with high ΦPL of 0.90 for PPI-
theoretically calculated molecular orbital distribution of PPI- PPITPA and 0.73 for PPI-PPIPCz. And the emission maximum of
PPITPA is shown in Figures 2a and 2b. The HOMO orbital is PPI-PPIPCz (402 nm) is much blue-shifted with respect to that of
totally localized at PPITPA group, while the LUMO orbital PPI-PPITPA (446 nm) in solution, which should be ascribed to the
distributes on the PPI group and imidazole ring of PPITPA. The one more benzene ring in PPI-PPITPA, inducing an elongated
molecular orbital distribution of PPI-PPIPCz is similar to PPI- conjugation. Interestingly, in the thin film state, PPI-PPIPCz shows
PPITPA (Figure S2). Obviously, the HOMO and LUMO of PPI- similar emission band with PPI-PPITPA, peaking at around 450 nm.
PPITPA and PPI-PPIPCz display adequate separation feature, The ΦPL of the thin films were measured to be 0.53 for PPI-PPITPA
which benefits the hole- and electron-transport (bipolar property) and 0.89 for PPI-PPIPCz. Such high fluorescence efficiencies are
and reduction of the singlet-triplet splitting.[5] The molecular packing essential for high-efficiency deep blue OLEDs. Based on low-
(Figure 2c) of PPI-PPITPA reveals that the PPI and PPITPA temperature PL measurements, the triplet energy levels are estimated
moieties separately aggregate into stack columns indicating that the to be 2.40 eV for PPI-PPITPA and 2.48 eV for PPI-PPIPCz,
electron and hole transport channels are perfectly constructed, respectively, which are sufficiently high for the excitation of GYR
respectively. Though stacking model in the film is different from phosphorescent dopants. The △EST values of PPI-PPITPA and PPI-
that in single crystal, the current–voltage characteristics (Figure S3) PPIPCz were calculated to be 0.38 eV and 0.35 eV, respectively.
of single carrier devices also verify that both compounds have The small △EST are advantageous for efficient energy transfer from
bipolar transport ability. The PPI (LUMO) and PPITPA (HOMO) the triplet excited state of hosts to GYR phosphorescent emitters.
moieties individually undertake the electron and hole transport
Figure 3. Room-temperature UV-vis absorption spectra, PL spectra of PPI-PPITPA
and PPI-PPIPCz in CH Cl solution and in neat films, as well as their
2
2
phosphorescence spectra in thin film at 77 K.
We first examined the two compounds’ EL property as blue
emitters by fabricating non-doped OLEDs with a structure of
[ITO/NPB (40 nm)/TCTA (5 nm)/PPI-PPITPA or PPI-PPIPCz (30
nm)/TPBI (50 nm)/LiF (1 nm)/Al] (device B1 with emitting layer
(EML) composed of PPI-PPITPA and device B2 with EML
composed of PPI-PPIPCz). The energy-level diagram and
molecular structures of the used materials are shown in Figure S7.
In devices B1 and B2, we utilized NPB (4,4’-bis[N-(1-naphthyl)-N-
phenyl amino] biphenyl) as the hole-transporting layer (HTL),
TCTA (4,4’,4’’- tris(Ncarbazolyl)triphenylamine) as the exciton-
blocking layer, TPBI (1,3,5-tris(N-phenylbenzimidazol-2-yl)benzene)
as the electron-transporting layer (ETL) and hole-blocking layer. LiF
served as electron-injecting layer and Al served as cathode. The non-
Figure 2. Calculated spatial distributions of the HOMO (a) and LUMO (b) and
molecular packing (c) of PPI-PPITPA
.
functions. The calculated electron (te) and hole (th) transfer integrals
for PPI-PPITPA are 0.025 and 0.061 eV, respectively, suggesting
that PPI-PPITPA can act as a bipolar transport material. The PPI-
PPITPA shows clear reduction and oxidation waves (Figure S4),
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doped devices B1 and B2 exhibit deep-blue emission with CIE
To explore the potential applications of these two compounds as
coordinates of (0.15, 0.08) and (0.15, 0.07), respectively, both of host materials for G, Y and R phosphorescent dopants, we fabricated
which are very close to the NTSC (National Television Standards GYR PhOLEDs with configurations of [ITO/NPB (40 nm)/TCTA (5
Committee) blue standard (CIE: 0.14, 0.08) and remain almost nm)/EML (30 nm)/TPBI (50 nm)/LiF (1 nm)/Al (100 nm)] (EML:
unchanged over a wide range of driving voltage. As shown in Figure PPI-PPITPA:5 wt% Ir(ppy)3 for device G1, PPI-PPITPA:5 wt%
4 and Figure S8, the maximum external quantum efficiencies (EQEs) Ir(ppy)2(dipig) for device Y1, PPI-PPITPA:8 wt% Ir(MDQ)2(acac)
of Device B1 and B2 are 7.7% and 8.1%, respectively. Device B1 for device R1 and PPI-PPIPCz:5 wt% Ir(ppy)3 for device G2, PPI-
using PPI-PPITPA as emitter shows a low turn-on voltage of 3.2 V PPIPCz:5 wt% Ir(ppy)2(dipig) for device Y2, PPI-PPIPCz:8 wt%
and a maximum luminance of 13950 cd m-2 at 10.5 V. The Ir(MDQ)2(acac) for device R2). The green phosphorescent complex
maximum current (CE) and power (PE) efficiencies of this device Ir(ppy)3 is fac-tris(2-phenylpyridine) iridium(III), yellow complex
are 5.6 cd A-1 and 5.5 lm W−1, respectively. Device B2 shows a Ir(ppy)2(dipig)
similar performance. It turns on at 3.4 V and achieves a maximum diisopropyl- guanidinate iridium(III) and red complex
brightness of 13820 cd m-2 at 10.5 V. The maximum CE and PE can Ir(MDQ)2(acac)
is bis(2-methyldibenzo-[f,h]quinoxaline)
be up to 4.8 cd A-1 and 4.5 lm W-1. To the best of our knowledge, acetylacetonate iridium(III) (Figure S9).
is
bis(2-phenylpyridinato)-N,N’-diisopropyl-
these efficiencies are the highest values reported for non-doped blue
Figure 4 and Figure S8 present the current density–voltage–
OLEDs with CIEy below 0.10.[6] Moreover, the EQE of these two brightness (J–V–L) characteristics, device performances and EL
devices maintains 5.4% and 6.0% respectively at a high brightness of spectra of the devices. The EL spectra are identical to the PL spectra
1000 cd m-2, indicating relatively small efficiency roll-offs.
(Figure S10) of the doped thin films. Device G2 exhibits a low
turn-on voltage of 2.8 V. The maximum EQE of 17.8% and PE of
65.7 lm W-1 are among the best values for green phosphorescent
OLEDs with blue emitters as hosts.[9] However, device G1 shows a
much lower EL efficiency than device G2. The reason can be
attributed to the lower triplet energy level (ET = 2.40 eV) of PPI-
PPITPA, which may cause back energy transfer from the green
guest triplet states to the host, resulting in a loss in efficiency.
Yellow PhOLEDs with excellent performance were also achieved by
employing these two compounds as hosts. For instance, devices Y1
exhibits the maximum EQE of 19.1%, CE of 61.8 cd A-1, and PE of
65.5 lm W-1, and device Y2 shows the similar behavior with the
maximum EQE of 18.1%, CE of 56.5 cd A-1, and PE of 58.8 lm W-1.
Finally, deep red PhOLEDs were fabricated by using PPI-PPITPA
and PPI-PPIPCz as host. Device R2 exhibits the maximum
luminance of 24810 cd m-2 at 13.5 V and excellent EL efficiencies
(18.0%, 21.3 cd A-1, and 20.9 lm W-1), whereas device R1 exhibits
the maximum luminance of 18020 cd m-2 at 11.0 V and EL
Figure 4. (a) Current density–voltage–brightness (J–V–L) characteristics; (b)
Current efficiencies and power efficiencies versus current density curves; (c)
External quantum efficiency versus luminance characteristics; (d) EL spectra and efficiencies (16.8%, 19.8 cd A-1, and 21.5 lm W-1) (Figure 4 and
CIE1931 coordinates of devices B2, G2, Y2 and R2 based on PPI-PPIPCz.
Figure S8). The PE values of devices R1 and R2 are comparable to
recently reported highly efficient deep red PhOLEDs.[10] Above
experimental results demonstrates that PPI-PPITPA and PPI-
PPIPCz are universal host materials for GYR phosphorescent
emitters. The detail EL parameters of the RYGB OLEDs are
summarized in Table 1.
In conclusion, we have designed and synthesized two deep blue
emitting materials PPI-PPITPA and PPI-PPIPCz with dual carrier
transport property and small singlet-triplet splitting feature. The
single crystal study of PPI-PPITPA revealed that the PPI and
PPITPA moieties assemble into electron and hole transport channels,
respectively, in solid state. The strong deep blue emission and good
ambipolar carrier transport characteristics of PPITPA and PPI-
PPIPCz ensure that the OLEDs with the two compounds as non-
dopant EML display extremely high EQE of 7.7%, 8.1% with true
deep blue CIE (0.15, 0.08) and (0.15, 0.07). Furthermore, the small
singlet-triplet splitting and good carrier transport properties allow
PPITPA and PPI-PPIPCz as hosts to fabricate RYG
phosphorescent emitting layers for PhOLEDs. High performance G,
Y and R PhOLEDs with EQE of 17.8%, 18.1% and 18.0%,
The EQE of OLEDs can be expressed by the well-known equation
of EQE = ηout × ηrc × ηγ ×ΦPL,[7] where ηout is the light-out-coupling
efficiency (~20%), ηrc is the product of the charge recombination
efficiency that is ideally 100% if holes and electrons are fully
balanced and completely recombined to form excitons, ηγ is
efficiency of radiative exciton production (25% for conventional
fluorescent OLEDs), ΦPL is photoluminescence (PL) quantum yield
of the emitter molecules (0.53 for PPI-PPITPA and 0.89 for PPI-
PPIPCz). Thus, the maximum EQE values of PPI-PPITPA and
PPI-PPIPCz devices can be calculated as 2.7% and 4.5%,
respectively. Clearly, the obtained EQEs (7.7% for PPI-PPITPA,
8.1% for PPI-PPIPCz) overcome the theoretical EQE limit of 5%
for the conventional fluorescent OLEDs. Since no delayed
fluorescence was observed from transient PL (Figure S8), the high
EQEs did not seem to be in accordance with TADF.[8] At this stage
we cannot give precise explanation for this phenomena and detail
experiments should be performed to disclose the mechanism.
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respectively, have been successfully obtained based on the two compounds and phosphors. These results demonstrate an efficient
Table 1. Electroluminescent performances of the devices.a)
Device
B1
Dopant
Von/V
3.2
3.4
2.8
2.8
2.9
3.0
2.8
2.3
Lmax/cd m−2
13950
13820
7022
CEb)/cd A−1
PEb)/lm W−1
EQEb)/%
CIE (x,y)c)
0.15, 0.08
0.15, 0.07
0.32, 0.60
0.32, 0.61
0.46, 0.53
0.45, 0.54
0.64,0.36
0.64,0.36
no
5.6, 4.6, 3.9
5.5,3.2,2.0
7.7, 6.4, 5.4
B2
no
4.8, 4.1, 3.6
4.5, 2.8, 1.8
8.1, 6.8, 6.0
G1
Ir(ppy)3
26.6, 11.5, 3.7
60.6, 51.5, 41.6
61.8, 55.5, 50.7
56.5, 49.7, 46.6
19.8, 18.3, 16.3
21.3, 16.9, 14.8
29.9, 8.3, 1.5
65.7, 41.9, 24.2
65.5, 37.6, 24.7
58.8, 32.2, 23.7
21.5, 14.1, 10.1
20.9, 11.2, 6.7
7.9, 3.5, 1.0
G2
Ir(ppy)3
55020
68990
75350
18020
39138
17.8, 15.3, 12.4
19.1, 17.2, 15.8
18.1, 15.8, 15.1
16.8, 15.6, 13.8
18.0, 14.2, 12.4
Y1
Ir(ppy)2(dipig)
Ir(ppy)2(dipig)
Ir(MDQ)2(acac)
Ir(MDQ)2(acac)
Y2
R1
R2
a)
Abbreviation: Von: Turn-on voltage. Lmax: Maximum luminance. CE: The maximum current efficiency. PE: The maximum power efficiency. EQE: The maximum
external quantum efficiency. b) in the order of maximum, then values at 100 and 1000 cd m–2. c) Measure at 100 cd m−2.
strategy to achieve full color OLEDs by developing the deep blue
organic luminescent materials with ideal D-A molecular structure
and molecular packing in solid state as well as small singlet-triplet
splitting.
(b) K. Wang, S. P. Wang, J. B. Wei, S. Y. Chen, D. Liu, Y. Liu, Y.
Wang, J. Mater. Chem. C., 2014, , 6817.
2
C. L. Li and S. P. Wang contributed equally to this work. This
work was supported by Natural Science Foundation of China
(91333201 and 21221063), National Basic Research Program of
China (2015CB655000) and Program for Chang Jiang Scholars and
Innovative Research Team in University (No.IRT13018).
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