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Communications Chemie

International Edition: DOI: 10.1002/anie.201806323

OLEDs Hot Paper German Edition: DOI: 10.1002/ange.201806323

Peripheral Amplification of Multi-Resonance Induced Thermally

Activated Delayed Fluorescence for Highly Efficient OLEDs
Xiao Liang, Zhi-Ping Yan, Hua-Bo Han, Zheng-Guang Wu, You-Xuan Zheng,* Hong Meng,*
Jing-Lin Zuo,* and Wei Huang*
Abstract: Multi-resonance induced by boron and nitrogen symbolizes a huge leap for OLEDs[5] because it endows pure
atoms in opposite resonance positions endows a thermally organic compounds with the capability to maximize the
activated delayed fluorescence (MR-TADF) emitter with efficiency of exciton harvesting to 100 %.[6] Owing to the small
a strikingly small full width at half maximum of only 26 nm band gap between S1 and T1 (DEST) states of these materials,
and excellent photoluminescence quantum yield of up to the reverse transferring process from T1 to S1 is drastically
97.48 %. The introduction of a carbazole unit in the para accelerated, leading to 100 % of energy utilization during
position of the B-substituted phenyl-ring can significantly electroluminescence process.[4, 7] To minimize the DEST, the
boost up the resonance effect without compromising the color most common strategy is to introduce spatially separated
fidelity, subsequently enhancing the performances of the HOMO (highest occupied molecular orbital) and LUMO
corresponding pure blue TADF-OLED, with an outstanding (lowest unoccupied molecular orbital) dominated moieties[8]
external quantum efficiency (EQE) up to 32.1 % and low without compromising the oscillating strength (f) between S1
efficiency roll-off, making it one of the best TADF-OLEDs in and ground (S0) state.[6d, 8, 9] This strategy has been validated
the blue region to date. Furthermore, utilizing this material as many times towards realization of highly efficient TADF
host for a yellow phosphorescent emitter, the device also shows characteristics,[4, 5, 9, 10] and numerous OLEDs bearing this
a significantly reduced turn-on voltage of 3.2 V and an EQEmax concept have been fabricated with decent performances.[11]
of 22.2 %. However, such strategy often comes with broader Stokes shift
because of the natural relaxation caused by spatial separation,
Organic light-emitting diodes (OLEDs) have been system- which directly impacts the color purity and device perform-
atically studied for decades since Tang and VanSlyke[1] ance.[3, 10c, 12]
reported the first-generation OLED based on a fluorescence In 2016, Hatakeyama et.al. reported two TADF emitters
emitter, and significantly improved in the second generation (DABNA-1 and DNBNA-2, Scheme 1) bearing a novel
with phosphorescent emitters, based on coordinate com- concept of multi-resonance (MR-TADF).[13] The boron and
pounds incorporating heavy metals such as iridium(III) and nitrogen (B-N) atoms are aligned in a specific pattern to
platinum(II).[2] These compounds can achieve full utilization induce the resonance of the core rigid framework, therein
of both singlet (S1) and triplet (T1) excitons generated during exhibiting a unique HOMO and LUMO distribution. The
the electroluminescence process owing to the strong spin– multi-resonance effect not only increases the oscillating
orbit coupling effect brought by IrIII or PtII atoms.[2a] However, strength between S1 and S0, but also help generate an
the development of next-gen OLED is impeded by the impressively small full width at half maximum (FWHM) of
expensive phosphorescent materials and lack of efficient only 28 nm. Such high color purity is unprecedented within
deep-blue emitters.[3]
The recent breakthrough of thermally activated delayed
fluorescence (TADF), first reported by C. Adachi et.al.,[4]

[*] X. Liang, Z.-P. Yan, H.-B. Han, Dr. Z.-G. Wu, Prof. Y.-X. Zheng,
Prof. J.-L. Zuo
State Key Laboratory of Coordination Chemistry, Collaborative
Innovation Center of Advanced Microstructures, Jiangsu Key Labo-
ratory of Advanced Organic Materials, School of Chemistry and
Chemical Engineering, Nanjing University
Nanjing, 210023 (P. R. China)
E-mail: [email protected]
[email protected]
X. Liang, Prof. H. Meng, Prof. W. Huang
Institute of Advanced Materials (IAM), Nanjing Tech University
Nanjing, 211800 (P. R. China) Scheme 1. a) Chemical structures of reported DABNA-1, DNBNA-2,
E-mail: [email protected] and TBN-TPA. b) Synthetic procedures: i) CuI, 18-crown-6, K2CO3,
[email protected] DMPU, sealed tube, 190 8C, 24 h; ii) Pd(AMPHOS)2Cl2, t-BuOK, o-
Supporting information and the ORCID identification number(s) for xylene, reflux, 18 h; iii) 1. n-BuLi, t-BuPh, 0 8C, 30 min, then 90 8C, 2 h;
the author(s) of this article can be found under: 2. BBr3, @42 8C, 4 h, then RT, 10 h; 3. NEt(i-Pr)2, 0 8C, then 100 8C,
https://doi.org/10.1002/anie.201806323. 24 h.

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Communications Chemie

TADF species.[11a] However, despite their high external

quantum efficiency (EQEmax = 20.2 %) and decent color
purity, the devices fabricated with these emitters exhibit
poor stability with serious efficiency roll-off. Besides, the
design choice is quite limited due to restricted position of
these B-N units to generate the multi-resonance effect.
Regarding the synthetic procedure of the MR-TADF emitter,
the boron atom has to be introduced through substitution of
halogen atom with lithium salts before incorporation of boron Figure 1. a) 3D excitation–emission correlation spectrum of TBN-TPA.
units, making it even less favorable to promote in the b) UV/Vis spectrum, and photoluminescence at room temperature and
structural design of future emitters. 77 K in toluene.
Herein, we introduce a fairly simple way to amplify the
multi-resonance effect induced by the B-N-containing core
structure and improve the photoluminescence quantum yield
(PLQY) by introducing a peripheral electron-donating car-
bazole unit without ever losing the pure color fidelity.
Compared with the reported materials of DABNA, the
synthetic procedure of MR-TADF material TBN-TPA is
also simplified via a direct one-pot borylation method[14]-
(Scheme 1). TBN-TPA shows a pure blue emission with
a small FWHM of 26 nm and a high PLQY up to 97.48 % in
toluene. The OLED employing TBN-TPA emitter exhibits
a significantly high EQE up to 32.1 % with suppressed
efficiency roll-off, which is among the best TADF-OLED in
blue region to date.[15] Moreover, the utilization of TBN-TPA
as a host for a yellow phosphorescent device employing an
IrIII complex can significantly reduce the turn-on voltage with
an EQE exceeding 20 %.
As shown in Scheme 1, the MR-TADF emitter TBN-TPA
was synthesized from one-pot borylation of the intermediate
product 2.[13, 14] The para-position of carbazole can be
deprotonated by n-BuLi directly without introducing addi- Figure 2. a) HOMO@1, HOMO, LUMO, LUMO + 1 distributions of
tional halogen-atoms while still maintaining a decent yield of DABNA-1 and TBN-TPA using B3LYP, 6–31g. b) Isosurface of DABNA-
26.3 %. The direct borylation not only simplifies the synthetic 1 and TBN-TPA mapped with ESP.
process and augments the possibility of designing more MR-
TADF compounds, but also makes it much easier to scale up.
As can be seen from the 3D excitation-emission correla- enhanced oscillating strength between HOMO and LUMO of
tion spectrum (Figure 1 a), the maximum excitation wave- 0.3076, (Table 1; Supporting Information, Tables S2, S3).
length and maximum emission wavelength are located at Furthermore, the oscillating strength between HOMO and
460 nm and 470 nm, respectively, with a Stokes shift of only LUMO for TBN-TPA is also improved to 0.3324, ultimately
10 nm and an extremely narrow excitation window. The UV/ increasing the overall radiative efficiency and consequently
Vis spectrum exhibits three distinguished peaks at 451, 389, better PLQY. Through self-consistent field (SCF) density
and 306 nm (Figure 1 b, left), significantly different from the mapped with electron static potential (ESP) distribution
UV/Vis spectrum of the reported DABNA-1, which has calculation (Figure 2 b), the electron-negative region
relatively weak absorption components located at 437 nm and expanded from the core B-N-containing heterocycle to
around 340 nm. To understand such difference in the UV/Vis carbazole fragment, indicating of better electron injection
absorption, time-dependent density-functional-theory (TD- capability,[16] while the electron-positive region around N
DFT) using B3LYP(6–31g) method was performed, and the atoms could potentially help facilitate better charge carrier
HOMO/LUMO distributions and corresponding energy injection. These results are potentially beneficial for the
levels are depicted in Figure 2 a. Accordingly, the electron- device performances using TBN-TPA as emitter or host.
rich carbazole unit contributes to the major compositions of The photoluminescence spectrum of TBN-TPA is very
HOMO@1 and LUMO + 1 distributions, lowering the similar to that of DABNA-1, with slightly red-shifted
LUMO + 1 energy level, meanwhile increasing the maximum wavelength of 470 nm owing to addition of an
HOMO@1 energy level, eventually leading to a much more electron-rich carbazole unit and a slightly smaller FWHM of
pronounced participation of HOMO@1 in the subsequent 26 nm in toluene solution. The DEST of TBN-TPA is merely
UV/Vis absorption. The emulation of UV/Vis spectrum of 0.03 eV, much smaller than DABNA-1, which could help
TBN-TPA (Supporting Information, Figure S6) also reveals accelerate the reverse inter-system crossing (RISC), leading
that the HOMO@1 to LUMO absorption are responsible to to better radiative efficiency. Benefitting from the enhanced
the UV absorption at around 400 nm, with a much more multi-resonance effect and involvement of carbazole unit in

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Table 1: Calculated and experimental properties of TBN-TPA and DABNA-1 in solutions or doped fims.
Calculated Experimental
Compound f1[a] f2[b] l[abs][c] l[PL][d] FPL[e] HOMO[f ] LUMO[g] DEST[h] tF[i] tDF[j] Td[k] FWHM
[nm] [nm] [%] [eV] [eV] [eV] [ns] [ms] [oC] [nm]
TBN-TPA 0.3324 0.3076 451 389 306 470[d] 97.48 @5.19 @2.56 0.14 6.02 51.02 406 26
DABNA-1[l] 0.3012[m] 0.0338[m] 437 460[n] 88.00 @5.58 @2.91 0.20 8.80 93.70 – 30
[a,b] Calculated oscillating coefficient of HOMO to LUMO (f1) and HOMO@1 to LUMO (f2). [c] UV/Vis absorption wavelength. [d] Measured in
oxygen-free toluene solution (5 W 10@5 m). [e] Absolute photoluminescence quantum yield. [f] HOMO energy level calculated from cyclic voltammetry
diagram (Supporting Information, Figure S3). [g] HOMO energy level calculated from onset of UV/Vis absorption. [h] Energy gap between S1 and T1
calculated from fluorescence and phosphorescence at 77 K. [i] Lifetime calculated from fluorescence decay. [j] Lifetime calculated from delayed
fluorescence in deposited thin film of TBN-TPA in 2,6-DCzppy under nitrogen atmosphere. [k] Decomposition temperature (5 % weight loss;
Supporting Information, Figure S1). [l] Data collected from previous reports. [k,m] Calculated adopting the method B3LYP(6–31g). [n] Measured in
deposited film in mCBP.

the absorption profile, the absolute quantum yield deter- are illustrated in Figure 3, detailed device performances are
mined with an integer-sphere system in degassed toluene depicted in Figure 4 and Table 2 (Supporting Information,
solution is substantially higher than that of DABNA-1, almost Table S8). The electroluminescence (EL) spectrum of TBN-
to 100 % (97.48 %), which could also be anticipated from TPA, with a FWHM of only 27 nm and CIE coordinates of
enhanced oscillating strength and a faster RISC process. The (0.12, 0.19), is almost identical to the photoluminescence in
transient lifetime decay was then determined via fluorescence solution with FWHM of only 27 nm and CIE coordinates of
decay and delayed fluorescence in deposited film of TBN- (0.12, 0.19), which is remarkable in terms of color purity.
TPA in a widely used host 2,6-DCzppy ((2,6-bis(3-(9H-
carbazol-9-yl)phenyl)pyridine)) in OLED fabrication. Nota-
bly, both the prompt fluorescence (tF = 6.01 ns) and delayed
fluorescence (tDF = 51.02 ms) lifetimes are considerably
smaller than that of DABNA-1 (tF = 8.8 ns, tDF = 93.7 ms in
CH2Cl2), which could be rationalized by stronger oscillating
strength and a smaller DEST.
To evaluate the device performances of TBN-TPA as
emitter and demonstrate our design strategy, device (D1) with
the configuration of ITO/MoO3 (molybdenum trioxide,
2.5 nm)/TAPC (di-[4-(N,N-ditolyl-amino)-phenyl]cyclohex-
ane, 30 nm)/2,6-DCzppy : 4 wt % TBN-TPA (10 nm)/
TmPyPB (1,3,5-tri(m-pyrid-3-yl-phenyl)benzene, 30 nm)/LiF
(1 nm)/Al (100 nm) was fabricated. The device structure
energy diagram and structures of materials used in this device

Figure 4. a) Current efficiency (CE)–luminance curve. b) Power effi-

ciency (PE)-luminance curve. c) External quantum efficiency (EQE)-
Figure 3. a) Energy diagrams of device structure D1, D2 and b) struc- luminance curve. d) Electroluminescence spectrum. e) CIE coordinates
tures of materials used in the devices. of the EL spectrum.

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Communications Chemie

Table 2: Device performances of D1 and D2.

Device l[EL][a] [nm] FWHM[b] [nm] Turn-on Maximum h[CE][cd/A][e] EQE[%][f ] h[PE][lm/W][g]
voltage[c] [V]
Luminance[d] Max/@100/@1000 Max/@100/@1000 Max/@100/@1000
[cd/m2]
D1 474 27 3.5 16 593 40.2/34.4/17.4 32.1/27.4/13.9 30.0/23.5/8.8
D2 559 32 3.2 30 339 79.1/55.3/54.3 22.2/15.6/15.2 67.1/43.5/36.3
[a] Maximum electrolumincescence wavelength. [b] Full width at half maximum of electroluminescence. [c] Turn-on voltage when brightness is 1 cd/
m2. [d] Maximum luminance. [e] Current efficiencies at luminance of maximum, 100, 1000 cd/m2. [f ] External quantum efficiencies at luminance of
maximum, 100, 1000 cd/m2. [g] Power efficiencies at luminance of maximum, 100, 1000 cd/m2.

Owing to the good charge carrier injection of TBN-TPA, the

turn-on voltage for D1 is only 3.5 V, which is significantly
smaller than that of the DABNA-1 based device (> 4 V).
Furthermore, the maximum luminance of D1 reaches 16
593 cd m@2, which is much brighter than that of DABNA-
1 based device (< 1000 cd m@2). The maximum current
efficiency (CE) and power efficiency (PE) for D1 are
40.2 cd/A, 30.0 lm/W, respectively. Owing to the blue and
narrow emission profile of TBN-TPA, high maximum exter-
nal quantum efficiency (EQEmax) up to 32.1 % was obtained.
The current efficiency and power efficiency are all unambig-
uously better and the efficiency roll-off is also reduced
compared with previous report.[11] In detail, the DABNA-
1 based device showed the maximum EQE, CE, and PE being
equal to 20.2 %, 21.1 cd/A, and 15.1 lm/W, and equal to
13.4 %, 14.2 cd/A, and 7.9 lm/W, respectively, at the practical
brightness of 100 cd m@2. In our case, the much higher EQE,
CE, and PE of 27.4 %, 34.4 cd/A and 23.5 lm/W, respectively,
can still be obtained at 100 cd m@2.
To further investigate the possibility of this MR-TADF
material as a host of phosphorescent OLED (PhOLED), the Figure 5. Device performance of D2: a) CE-luminance curve; b) PE-
device (D2) with a configuration of ITO (50 nm)/HATCN luminance curve; c) EQE-luminance curve; d) EL spectrum; e) lumi-
(hexa-azaztriphenylene-hexacabonitrile, 5 nm)/TAPC nance–voltage and current-density–voltage curves.
(30 nm)/TBN-TPA: 16 wt % Ir(tfmphqz)2(tpip) (10 nm)/
TmPyPB (30 nm)/ LiF (1 nm)/Al (100 nm) was also fabri-
cated. The yellow phosphorescent emitter Ir(tfmphqz)2(tpip)
is taken from the previously reported work in our group.[17] with EQE up to 32.1 %, and maximum luminance of more
Derived from Figure 5 it is evident that OLED based on than 16 000 cd m@2, combined with a reduced efficiency roll-
TBN-TPA host also exhibits decent performances with off. Device based on this MR-TADF material as a host also
a significantly lower turn-on voltage (3.2 V) than the pre- exhibits low turn-on voltage and decent device efficacy. The
viously reported device with 2,6-DCzppy as host,[17] together significant improvement within MR-TADF species ascertains
with a maximum luminance of 30 339 cd m@2, which could be that the introduction of peripheral carbazole groups can
originating from better carrier injection ability of TBN-TPA. enhance the multi-resonance effect and boost the radiative
Moreover, the luminance of D2 reaches 100 cd m@2, decay efficiency. Our strategy provides a feasible pathway
1000 cd m@2, and 10 000 cd m@2 at operating voltages of towards design of more MR-TADF materials with ultra-pure
4.0 V, 4.7 V, and 6.4 V, respectively, potentially ascribed to emission profiles and corresponding OLEDs with superior
good charge injection properties. The maximum EQE of D2 is performances.
up to 22.2 % with a maximum CE of 79.1 cd/A and a maximum
PE of 67.1 lm/W. The CE reduces from 55.32 cd m@2 to
54.29 cd m@2 at 100 cd m@2 and 1 000 cd m@2, exhibiting a rel- Acknowledgements
atively small roll-off at high luminance intensity.
In conclusion, by introducing a pheripheral carbazole This work is supported by National Natural Science Founda-
group, an efficient MR-TADF material was synthesized tion of China (51773088, 21631006), the National Key R&D
through a simple direct borylation and then employed in Program of China (No. 2018YFA0306004), and the Natural
decent pure blue MR-TADF-OLED and a yellow PhOLED. National Science Foundation of China and Pakistan Science
The ultra-pure blue device exhibits superior performance Foundation Collaborative research project (5161101159).

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Communications Chemie

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