Добавил:
Sekretar
kiopkiopkiop18@yandex.ru
t.me/Prokururor I Вовсе не секретарь, но почту проверяю
Опубликованный материал нарушает ваши авторские права? Сообщите нам.
Вуз:
Предмет:
Файл:Ординатура / Хирургия / Библиотека им академика М.И. Перельмана / Книга_5710_Библиотеки_им_академика_М_И_Перельмана
.pdf
1,2,4 and 1,3,4-Oxadiazole Scaffolds in Designing Organic Light-Emitting Diodes 33
F
3
C CF
3
MeO
OMe
NN
N
N
O
Me
O
N
N
Me
NN
N
N
O
O
N
N
NN
N
N
O
O
N
N
NN
N
N
O
O
N
N
82 83
84
85
Structures 82–85
N
N
N
N
N
N
N
N
O
O
O
N
N
N
88
87
86
N
N
O
N
N
89
Structures 86–89
between oxadiazole and carbazole owing to effective HOMO-LUMO separation.
OLED devices prepared from compound 82 exhibited maximum external quantum
efficiency (EQE ) as 11.8% with deep-blue emission having color coordinate (CIE)
max
at (0.17, 0.17). However, the device obtained using compound 84 displayed higher
EQE (12.3%) with sky-blue emission having CIE coordinates at (0.17, 0.25).
max
Tan et al. developed hybrid compounds 86–89 by tuning electronic structures
around aromatic nuclei using carbazole and oxadiazole units in three synthetic steps
(Tan et al. 2019). Sequential introduction of nitrogen (N) heteroatom in the aromatic
structure of the compounds 86–88 resulted in reduced energy gaps and bathochromic
shifting of emission bands. All these compounds displayed high photoluminescent
quantum yields. The fabricated nanodoped deep blue OLED device (made by the
best candidate) prepared by the authors exhibited 4.0% maximum external quantum
efficiency and 4,406 cd/m
2
as maximum brightness.
Difluoroboron (BF
2
)-attached compounds exhibit better electron withdrawing
response and strong luminescence efficiency. Zhou et al. prepared hybrid compounds
90–91 in 2–3 synthetic steps where both phenolic derivative (and its BF
2
-analog)
and 9,9-dimethylacridine were attached with the help of an oxadiazole moiety
(Zhou et al. 2019). Compounds 90–91 exhibited sky-blue emission (maxima in the
range of 470490 nm) (Figure 4) both in solution as well as film state, indicating
good TADF (thermally activated delayed fluorescence) properties. The developed
https://t.me/med1917
34 Oxadiazole in Material and Medicinal Chemistry
OH
N
N
O
N
O
N
N
O
N
B
F
F
90
91
Structures 90–91
Figure 4. (a) Plot showing EQE vs. current density of OLED devices originating from 90 and 91 (a, c).
E/XPLQDQFHFXUUHQWGHQVLW\YROWDJH/í-í9FXUYHRI2/('GHYLFHVEG5HSURGXFHGKHUHZLWKWKH
permission of the American Chemical Society (Zhou et al. 2019).
TADF characteristics are ascribed to the existence of keto form in the triplet state
of 90–91. In order to incorporate suitable host material, the authors could tune the
external quantum efficiency of the designed OLED materials. In the presence of
9-(4-tert-butylphenyl)-3,6-bis(triphenylsilyl)-9H-carbazole as a host material,
the synthesized oxadiazole compounds 90–91 displayed 2.98 and 13.8%
maximum external quantum efficiency (EQE), respectively. Interestingly,
the EQE parameter for 90–91 increased to 12.1 and 20.1% (Figure 4) in the
presence of 10-(4-((4-(9H-carbazol-9-yl)phenyl)sulfonyl)phenyl)-9,9-dimethyl-
9,10-dihydroacridine as a host material.
In 2019, researchers at the Georgia Institute of Technology (Zhang et al.) studied
host-free OLEDs utilizing oxadiazole-based compound 92 with diagonally connected
four carbazole moieties (Zhang et al. 2019). The OLED device prepared from this
yellow-green-emitting compound 92 exhibited significant light-emitting properties
such as 79 lmW
–1
as power efficiency, 10 cdm
–2
as luminance, 73 cdA
–1
as current
efficiency, and 21% of maximum external quantum efficiency. Compound 92 could
be utilized as a TADF emitter in organic electronics.
Irradiation of light upon a charge transfer complex at its charge transfer band
produces exciplex (also known as excited charge transfer complex) (Guo et al.
2021). Exciplex emissive materials show promising optical properties owing to
100% exciton harvesting, highly advantageous bipolar nature, and preferred dipole
https://t.me/med1917
1,2,4 and 1,3,4-Oxadiazole Scaffolds in Designing Organic Light-Emitting Diodes 35
t
Bu
94.
R
=
n-propyl
O
N
N
N
N
O
O O
93
O
N
N
N
N
O
R
R
R
R
N
N
N
N
N
N
NN
O
t
Bu
O
92
95.
R
=
n-hexyl
Structures 92–95
Figure 5. (a) Plot showing voltage vs. current density and luminance, (b) luminance vs. EQE, and
(c) luminance vs. power efficiency of OLED devices. Reproduced here with the permission of the
American Chemical Society (Saghaei et al. 2021).
alignment (Wang et al. 2019). Oxadiazole derivatives are interesting electron
transport materials that could be solution-processed to yield highly efficient exciplex
emissive films. In order to utilize exciplex blends in OLED applications, Saghaei
et al. tailored three oxadiazole-based compounds 93–95 with better solubility
and compared their performance with commercially available electron transport
material OXD-7 (Saghaei et al. 2021). Films prepared from these synthesized
oxadiazole compounds exhibited greater electron mobilities in comparison to
OXD-7. Additionally, these synthesized compounds formed a homogeneous (soluble)
solution in the presence of hole-transporting material 4,4’,4’’-tris[phenyl(m-tolyl)
amino]-triphenylamine (m-MTDATA). Blending m-MTDATA with compound 93
displayed 5.3 ± 0.3% as maximum external quantum efficiency (Figure 5) and a
high value of photoluminescence quantum yield (21 ± 3%) among three synthesized
compounds.
https://t.me/med1917
36 Oxadiazole in Material and Medicinal Chemistry
4. Metal Complex-Based Oxadiazole Systems
In an effort to understand the relevance of iridium complexes toward the effectiveness
of electroluminescent devices, Tang et al. developed complexes 96 and 97 utilizing
3-(5-(4-(pyridin-2-yl)phenyl)-1,3,4-oxadiazol-2-yl)-9-hexyl-9H-carbazole and its
iridium complex (Tang et al. 2011). Complexes 96 and 97 exhibited 188°C and
201°C as high glass-transition temperatures, respectively. Polymer LEDs fabricated
from complexes 96 and 97 exhibited very high luminance efficiency of 11.1 and
16.4 cdA
–1
, respectively (Figure 6).
Oxadiazole-type counter-anions play a significant role in performance
enhancement in OLED devices. Taking advantage of the cationic nature of iridium
complexes and combining it with oxadiazole-type counter-anions can facilitate energy
transfer in the fabricated films. Meng et al. synthesized cationic iridium complexes
98–100 with different counter-anions in 4–5 synthetic steps from commercially
available precursors such as Sodium 3-sulfobenzoate and the respective analog
(Meng et al. 2020). The authors obtained a 1.4 times improvement in efficiency in
N
N
N
N
N
Ir
+
O
N
N
R
X
R
=
H,
X
=
SO
3
-
;
complex
98
R
=
t
Bu,
X
=
SO
3
-
;
complex
99
R
=
t
Bu,
X
=
BF
3
-
;
complex
100
N
O
N
N
N
O
O
Ir
2
96
N
O
N
N
N
Ir
3
97
Structures 96–100
Figure 6. (Left) Plot showing luminance and current density (inset) vs. voltage; (right) plot with current
efficiency vs. current density. The graph shows 4 wt % doping concentrations. Reprinted with permission
from Elsevier (Tang et al. 2011).
https://t.me/med1917
N
n
CF
3
n
CF
3
N
O
O
NN
CF
3
NN
O
CF
3
101
102
O(CH
2
)
11
CH
3
O O
O(CH
2
CH
2
O)
3
NN NN
n
H
3
C(H
2
C)
11
O
103
Structures 101–103
C
12
H
25
O
O
C
12
H
25
O
OC
12
H
25
N
N
O
m
n
104
;
when
m
=1,
n=
0
C
12
H
25
O
O
N
N
O
S
n
106
105
;
when
m=
0.5,
n=
0.5
Structures 104–106
1,2,4 and 1,3,4-Oxadiazole Scaffolds in Designing Organic Light-Emitting Diodes 37
the fabricated solution-processed OLED device prepared from complexes 98–100
–
compared to the referenced complex with PF
6
counter anion. Blue-green emitting
device prepared from iridium complex with oxadiazole-SO
3
–
counter-anion displayed
a very high value of EQE (15.2%) and peak current efficiency (37.6 cdA
–1
) among
max
available cationic iridium complexes.
5. Polymer-Based Oxadiazole Systems
In 1995, Pei et al. reported synthesizing a set of polymers 101–103 consisting
of 1,3,4-oxadiazole units with different conjugation lengths and solubility (Pei
and Yang 1995). The non-fluorescent polymer 101 exhibited the largest ʌ–ʌ*
bandgap. Interestingly, attachment of extra oxadiazole unit (in case of polymer
102) strengthened its electron transport nature. Alternatively, polymers with longer
conjugation lengths, such as 103, exhibited intense blue fluorescence response. The
fabricated blue LED device utilizing polymer 103 as the electron injection layer,
polyaniline as the hole injection layer (and calcium as a cathode) exhibited 0.1%
EQE and 4.5 V voltage. In this way, longer conjugating materials could potentially
increase blue fluorescence behavior.
Bao et al. designed and synthesized hybrid polymers 104–106 by attaching
oxadiazole units adjacent to the conjugated hole-transporting scaffold such as
poly(phenylene vinylene) or poly(phenylene thiophene) (Bao et al. 1998). Polymers
104 and 105 displayed two distinct absorption bands, one at 330 nm from the
oxadiazole scaffold and the second at 460 nm. Excitation of 104–106 polymeric thin
films at 442 nm exhibited one emission peak at 580 nm in the case of 104–105 and
https://t.me/med1917
38 Oxadiazole in Material and Medicinal Chemistry
Structures 107–110
NN
O
N
N
OC
8
H
17
n
108
N
N
O
N
N
OC
8
H
17
n
109
N
N
O
N
N
OC
8
H
17
n
110
O
NN
O
N
O
O
6
107
n
at 590 nm in the case of 106. Due to hole-transporting, electron-transporting, and
light-emitting characteristics in a single species, the designed polymers 104–106 are
well suited for fabricating single-layer LED devices.
Polymeric liquid crystals exhibit significant applications in nonlinear optical
devices, light-emitting materials, and optoelectronics with interesting phase
structures and transitions (Chai et al. 2007; Concellón et al. 2018). Kawamoto
et al. developed a polymer liquid crystal utilizing 107, where an oxadiazole scaffold
acted as an electron-transporting moiety and the corresponding amine group as a
hole-transporting group (Kawamoto et al. 2003). A maximum brightness of around
13 cd/m
2
was noticed with blue emission when polymer 107 was incorporated into
the OLED device. In order to tune the triplet energy, Zhang et al. tailored copolymers
108–110 using a carbazole-oxadiazole hybrid system through Suzuki cross-
coupling reactions (Zhang et al. 2008). Copolymers were obtained through 3,6-,
3,6-alt-2,7-, and 2,7-linkage at the carbazole moiety. These copolymers displayed good
thermal stability and glass-transition temperatures of 211°C, 194°C, and 208°C for
108–110, respectively. Fluorescence quantum efficiencies enhanced remarkably
with blue emissions, and the triplet energies were obtained as 2.52, 2.42, and 2.32 eV,
respectively, for copolymers 108–110. The fabricated polymeric OLEDs utilizing
copolymers 108–110 as host materials and bis(2,4-diphenylquinolinato-N,C
2’
)
iridium(acetylacetonate) as guest material exhibited 3.1 to 4.3 V as turn-on voltage.
Sun et al. utilized fluorene-oxadiazole copolymer 111 to develop white
light-emitting electrochemical cells (Sun et al. 2010). Copolymer 111 is composed
of 25 mol % 5,5’-diphenyl-2,2’-bi-1,3,4-oxadiazole and 75 mol % fluorene.
https://t.me/med1917
NNN
N
N
O
C
8
H
17
NN
N
NN
O
C
8
H
17
OO
O
OO
O
OO
OO
nn
C
8
H
17
m
C
8
H
17
111
Structure 111
N
N
O
O
N
N
N
N
O
O
N
N
O
114
O
N
N
112
113
N
O
N
N
Ir
N
N
115
Structures 112–115
n
O
O
O
N
N
1,2,4 and 1,3,4-Oxadiazole Scaffolds in Designing Organic Light-Emitting Diodes 39
Attachment of 2-(2-(2-Methoxyethoxy)ethoxy)ethyl group at the C9 position
of fluorene facilitated ionic conductivity. About 4.6 V turn-on voltage and
29.4 mA/cm
2
maximum luminance were obtained from the light-emitting
electrochemical cell using copolymer 111. White emission was also observed with
CIE coordinates (0.24, 0.31).
Zhang et al. developed various polymeric systems 112–115, such as
polymethacrylates, polystyrenes, and polynorbornenes via phenylene-linked
oxadiazole-carbazole hybrid scaffolds (Zhang et al. 2011). These synthesized
polymers displayed good thermal stability and 118–209°C at moderate to high
glass-transition temperatures. These polymers could be useful for preparing green
and blue-green phosphorescent materials. The fabricated OLED device utilizing
polymer 115 displayed 10.0% EQE , 34.1 cdA
–1
as current efficiency, and 6.0 V
max
turn-on voltage.
https://t.me/med1917
40 Oxadiazole in Material and Medicinal Chemistry
6. Conclusions
Organic and polymeric electronics have achieved tremendous advancement in
the last two decades. For example, the quality of electronic and optical devices
has significantly increased. Electroluminescent devices made up of oxadiazole
moieties exhibit high quantum efficiencies and are suitable for fabricating organic
light-emitting diodes. These devices find extensive applications in illumination
and display. Well-known electron transporter 1,3,4-oxadiazole, connected to
two triphenylamine groups as a hole transporter (as in the case of compound 33),
displayed highly emissive OLED characteristics due to discontinuity in conjugation.
Water/alcohol-soluble oxadiazole derivatives have been instrumental in fabricating
solution-processable devices. Challenges include devising high quantum efficient
materials with increased current density. A lower rate of quantum efficiency (with a
rise in current density) is associated with loss of charge balance, exciton generation
in the hole transport layer, exciton segregation in the presence of an electric field, etc.
(Dumur and Goubard 2014). Developing new materials with differing combinations
of electron transporter and hole transporter might increase quantum efficiency.
References
$KQ-&:DQJ &3HDUVRQ0%U\FHDQG03HWW\ 2UJDQLFOLJKWHPLWWLQJGLRGHV EDVHGRQD
blend of poly [2-(2-ethylhexyloxy)-5-methoxy-1, 4-phenylenevinylene] and an electron transporting
material. Appl. Phys. Lett. 85(7): 1283–1285.
Bao, Z., Z. Peng, M. E. Galvin and E. A. Chandross. 1998. Novel oxadiazole side chain conjugated
polymers as single-layer light-emitting diodes with improved quantum efficiencies. Chem. Mater.
10(5): 1201–1204.
Chai, C.-P., X.-Q. Zhu, P. Wang, M.-Q. Ren, X.-F. Chen, Y.-D. Xu et al. 2007. Synthesis and phase
structures of mesogen-jacketed liquid crystalline polymers containing 1, 3, 4-oxadiazole based side
chains. Macromol. 40(26): 9361–9370.
Chan, L.-H., R.-H. Lee, C.-F. Hsieh, H.-C. Yeh and C.-T. Chen. 2002. Optimization of high-performance
EOXHRUJDQLFOLJKWHPLWWLQJ GLRGHV FRQWDLQLQJ WHWUDSKHQ\OVLODQH PROHFXODU JODVVPDWHULDOV-$P
Chem. Soc. 124(22): 6469–6479.
&KDQJ <7 -. &KDQJ <7 /HH 36 :DQJ -/ :X && +VX HW DO +LJKHIILFLHQF\
small-molecule-based organic light emitting devices with solution processes and oxadiazole-based
electron transport materials. ACS Appl. Mater. Interfaces 5(21): 10614–10622.
&KHQ +) /& &KL :< +XQJ :- &KHQ 7< +ZX <+ &KHQ HW DO &DUED]ROH DQG
benzimidazole/oxadiazole hybrids as bipolar host materials for sky blue, green, and red PhOLEDs.
Org. Electron. 13(11): 2671–2681.
Cheng, S.-H., S.-H. Chou, W.-Y. Hung, H.-W. You, Y.-M. Chen, A. Chaskar et al. 2013. Fine-tuning the
balance between carbazole and oxadiazole units in bipolar hosts to realize highly efficient green
PhOLEDs. Org. Electron. 14(4): 1086–1093.
Chidirala, S., H. Ulla, A. Valaboju, M. R. Kiran, M. E. Mohanty, M. Satyanarayan et al. 2016.
Pyrene–oxadiazoles for organic light-emitting diodes: triplet to singlet energy transfer and role of
KROHLQMHFWLRQKROHEORFNLQJPDWHULDOV-2UJ&KHP±
&RQFHOOyQ$6+HUQiQGH]$LQVD-%DUEHUi35RPHUR- /6HUUDQRDQG00DUFRV 3URWRQ
conductive ionic liquid crystalline poly (ethyleneimine) polymers functionalized with oxadiazole.
RSC Adv. 8(66): 37700–37706.
Dumur, F. and F. Goubard. 2014. Triphenylamines and 1, 3, 4-oxadiazoles: a versatile combination for
FRQWUROOLQJWKHFKDUJHEDODQFHLQRUJDQLFHOHFWURQLFV1HZ-&KHP±
Fukushima, T. 2018. Pi conjugated system bricolage (figuration) toward functional organic molecular
systems. Mater. Chem. Front. 2(9): 1594–1594.
https://t.me/med1917
1,2,4 and 1,3,4-Oxadiazole Scaffolds in Designing Organic Light-Emitting Diodes 41
Gong, S., Q. Fu, W. Zeng, C. Zhong, C. Yang, D. Ma et al. 2012. Solution-processed double-silicon-
bridged oxadiazole/arylamine hosts for high-efficiency blue electrophosphorescence. Chem. Mater.
24(16): 3120–3127.
*RQJ6&=KRQJ 4)X'0D-4LQDQG&<DQJ([WHQVLRQRIPROHFXODUVWUXFWXUHWRZDUG
VROXWLRQSURFHVVDEOHKRVWVIRUHIILFLHQWEOXHSKRVSKRUHVFHQWRUJDQLFOLJKWHPLWWLQJGLRGHV-3K\V
Chem. C 117(1): 549–555.
*XR - < =KHQ + 'RQJ DQG : +X 5HFHQW SURJUHVV RQ RUJDQLF H[FLSOH[ PDWHULDOV ZLWK
GLIIHUHQW GRQRUDFFHSWRU FRQWDFWLQJ PRGHV IRU OXPLQHVFHQW DSSOLFDWLRQV - 0DWHU &KHP &
9(47): 16843–16858.
+DQ :6 +- 6RQ .5 :HH .7 0LQ 6 .ZRQ ,+ 6XK HW DO 6LOLFRQEDVHG
blue phosphorescence host materials: structure and photophysical property relationship on
methyl/phenylsilanes adorned with 4-(N-carbazolyl) phenyl groups and optimization of
WKHLU HOHFWUROXPLQHVFHQFH E\ SHULSKHUDO 1FDUED]RO\O SKHQ\O QXPEHUV - 3K\V &KHP &
113(45): 19686–19693.
Hughes, G. and M. R. Bryce. 2005. Electron-transporting materials for organic electroluminescent and
HOHFWURSKRVSKRUHVFHQWGHYLFHV-0DWHU&KHP&±
Kawamoto, M., H. Mochizuki, A. Shishido, O. Tsutsumi, T. Ikeda, B. Lee et al. 2003. Side-chain polymer
liquid crystals containing oxadiazole and amine moieties with carrier-transporting abilities for
VLQJOHOD\HUOLJKWHPLWWLQJGLRGHV-3K\V&KHP%±
/HH$5-/HH-/HHDQG:6+DQ6LOLFRQEDVHGFDUED]ROHDQGR[DGLD]ROHK\EULGDVDELSRODU
host material for phosphorescent organic light-emitting diodes. Org. Electron. 38: 222–229.
/HH'5 &: /HHDQG-< /HH+LJKWULSOHW HQHUJ\KRVWPDWHULDOV IRUEOXHSKRVSKRUHVFHQW
RUJDQLFOLJKWHPLWWLQJGLRGHVGHULYHGIURPFDUED]ROHPRGLILHGRUWKRSKHQ\OHQH-0DWHU&KHP&
2(35): 7256–7263.
/HH-.6KL]X+7DQDND+1RPXUD7<DVXGDDQG&$GDFKL2[DGLD]ROHDQGWULD]ROHEDVHG
highly-efficient thermally activated delayed fluorescence emitters for organic light-emitting diodes.
-0DWHU&KHP&±
/HXQJ 0N && <DQJ -+ /HH ++ 7VDL &) /LQ &< +XDQJ HW DO 7KH XQXVXDO
electrochemical and photophysical behavior of 2, 2 ‘-bis (1, 3, 4-oxadiazol-2-yl) biphenyls, effective
electron transport hosts for phosphorescent organic light emitting diodes. Org. Lett. 9(2): 235–238.
/HXQJ0N:+<DQJ&1&KXDQJ-+/HH&)/LQ0.:HLHWDO2[DGLD]ROH
containing silanes as novel hosts for blue phosphorescent organic light emitting diodes. Org. Lett.
14(19): 4986–4989.
/L4/6&XL&=KRQJ=4-LDQJDQG/6/LDR$V\PPHWULFGHVLJQRIELSRODUKRVWPDWHULDOV
with novel 1, 2, 4-oxadiazole unit in blue phosphorescent device. Org. Lett. 16(6): 1622–1625.
/L4/6&XL&=KRQJ;'<XDQ6&'RQJ=4-LDQJHWDO6\QWKHVLVRIQHZELSRODUKRVW
materials based on 1, 2, 4-oxadiazole for blue phosphorescent OLEDs. Dyes Pigms. 101: 142–149.
Li, Z., W. Li, C. Keum, E. Archer, B. Zhao, A. M. Slawin et al. 2019. 1, 3, 4-Oxadiazole-based deep blue
WKHUPDOO\DFWLYDWHGGHOD\HGIOXRUHVFHQFHHPLWWHUVIRURUJDQLFOLJKWHPLWWLQJGLRGHV-3K\V&KHP
C 123(40): 24772–24785.
/LRX*6 6++VLDR:&&KHQDQG+-<HQ $QHZ FODVVRIKLJK7JDQGRUJDQRVROXEOH
DURPDWLF SRO\ DPLQHí R[DGLD]ROH V FRQWDLQLQJ GRQRU DQG DFFHSWRU PRLHWLHV IRU
blue-light-emitting materials. Macromol. 39(18): 6036–6045.
Meng, X., P. Wang, R. Bai and L. He. 2020. Blue-green-emitting cationic iridium complexes with
oxadiazole-type counter-anions and their use for highly efficient solution-processed organic
OLJKWHPLWWLQJGLRGHV-0DWHU&KHP&±
Oyston, S., C. Wang, G. Hughes, A. S. Batsanov, I. F. Perepichka, M. R. Bryce et al. 2005. New 2,
5-diaryl-1, 3, 4-oxadiazole–fluorene hybrids as electron transporting materials for blended-layer
RUJDQLFOLJKWHPLWWLQJGLRGHV-0DWHU&KHP±
Paun, A., N. Hadade, C. Paraschivescu and M. Matache. 2016. 1, 3, 4-Oxadiazoles as luminescent
PDWHULDOV IRU RUJDQLF OLJKW HPLWWLQJ GLRGHV YLD FURVVFRXSOLQJ UHDFWLRQV - 0DWHU &KHP &
4(37): 8596–8610.
Pei, Q. and Y. Yang. 1995. 1, 3, 4-Oxadiazole-containing polymers as electron-injection and blue
electroluminescent materials in polymer light-emitting diodes. Chem. Mater. 7(8): 1568–1575.
https://t.me/med1917
42 Oxadiazole in Material and Medicinal Chemistry
5HGG\0$$7KRPDV.6ULQLYDV9-5DR.%KDQXSUDNDVK%6ULGKDUHWDO6\QWKHVLVDQG
characterization of 9, 10-bis (2-phenyl-1, 3, 4-oxadiazole) derivatives of anthracene: Efficient n-type
HPLWWHUIRURUJDQLFOLJKWHPLWWLQJGLRGHV-0DWHU&KHP±
6DJKDHL-7/HLWQHU9710DL&6.5DQDVLQJKH3/%XUQ,5*HQWOHHWDO(PLVVLYH
material optimization for solution-processed Exciplex OLEDs. ACS Appl. Electron. Mater.
3(11): 4757–4767.
6KLK&+35DMDPDOOL&$:X0-&KLX/.&KXDQG&+&KHQJ$KLJKWULSOHWHQHUJ\
high thermal stability oxadiazole derivative as the electron transporter for highly efficient red, green
DQGEOXHSKRVSKRUHVFHQW2/('V-0DWHU&KHP&±
Song, L., Y. Hu, Z. Liu, Y. Lv, X. Guo and X. Liu. 2017. Harvesting triplet excitons with exciplex
thermally activated delayed fluorescence emitters toward high performance heterostructured organic
light-emitting field effect transistors. ACS Appl. Mater. Interfaces 9(3): 2711–2719.
6XQ 0 & =KRQJ ) /L < &DR DQG 4 3HL $ IOXRUHQHíR[DGLD]ROH FRSRO\PHU IRU ZKLWH
light-emitting electrochemical cells. Macromol. 43(4): 1714–1718.
Tamoto, N., C. Adachi and K. Nagai. 1997. Electroluminescence of 1, 3, 4-oxadiazole and
triphenylamine-containing molecules as an emitter in organic multilayer light emitting diodes.
Chem. Mater. 9(5): 1077–1085.
7DQ<%5XL-/L==KDR=/LX=%LDQHWDO%OXHWKHUPDOO\DFWLYDWHGGHOD\HGIOXRUHVFHQFH
emitters based on a constructing strategy with diversed donors and oxadiazole acceptor and their
efficient electroluminescent devices. Opt. Mater. 94: 103–112.
Tan, Y., Z. Wang, C. Wei, Z. Liu, Z. Bian and C. Huang. 2019. Nondoped deep-blue fluorescent
organic electroluminescent device with CIEy = 0.06 and low efficiency roll-off based on
carbazole/oxadiazole derivatives. Org. Electron. 69: 77–84.
Tang, C. W. and S. A. VanSlyke. 1987. Organic electroluminescent diodes. Appl. Phys. Lett.
51(12): 913–915.
Tang, H., Y. Li, C. Wei, B. Chen, W. Yang, H. Wu et al. 2011. Novel yellow phosphorescent iridium
complexes containing a carbazole–oxadiazole unit used in polymeric light-emitting diodes. Dyes
Pigms. 91(3): 413–421.
7DR</$R4:DQJ&=KRQJ&<DQJ -4LQHW DO0RUSKRORJLFDOVWDEOHVSLURELIOXRUHQH
oxadiazole hybrids as bipolar host materials for efficient green and red electrophosphorescence.
&KHP$VLDQ-±
7DR<4:DQJ/$R&=KRQJ-4LQ&<DQJHWDO0ROHFXODUGHVLJQRIKRVWPDWHULDOVEDVHG
on triphenylamine/oxadiazole hybrids for excellent deep-red phosphorescent organic light-emitting
GLRGHV-0DWHU&KHP±
7DR<4:DQJ<6KDQJ&<DQJ/$R-4LQHWDO0XOWLIXQFWLRQDOELSRODUWULSKHQ\ODPLQH
oxadiazole derivatives: highly efficient blue fluorescence, red phosphorescence host and two-color
based white OLEDs. Chem. Commun. (1): 77–79.
7DR< 4:DQJ &<DQJ - 4LQ DQG'0D 0DQDJLQJ FKDUJHEDODQFHDQGWULSOHWH[FLWRQV WR
achieve high-power-efficiency phosphorescent organic light-emitting diodes. ACS Appl. Mater.
Interfaces 2(10): 2813–2818.
Tao, Y., Q. Wang, C. Yang, Q. Wang, Z. Zhang, T. Zou et al. 2008. A simple carbazole/oxadiazole hybrid
molecule: an excellent bipolar host for green and red phosphorescent OLEDs. Angew. Chem., Int.
Ed. 47(42): 8104–8107.
7DR<4:DQJ&<DQJ&=KRQJ-4LQDQG'0D0XOWLIXQFWLRQDOWULSKHQ\ODPLQHR[DGLD]ROH
K\EULGDVKRVWDQGH[FLWRQဨEORFNLQJPDWHULDOKLJKHIILFLHQF\JUHHQSKRVSKRUHVFHQW2/('VXVLQJ
easily available and common materials. Adv. Funct. Mater. 20(17): 2923–2929.
7XQJ</3&:X&6/LX<&KL-.<X<++XHWDO+LJKO\HIILFLHQWUHGSKRVSKRUHVFHQW
osmium (II) complexes for OLED applications. Organometallics 23(15): 3745–3748.
9HQNDWDNULVKQDQ331DWDUDMDQ-10RRUWK\=/LQDQG7-&KRZ7ZLVWHGELPHVLW\OHQHEDVHG
oxadiazoles as novel host materials for phosphorescent OLEDs. Tetrahedron 68(36): 7502–7508.
:DQJ&*<-XQJ<+XD&3HDUVRQ05%U\FH0&3HWW\HWDO$QHIILFLHQWS\ULGLQHDQG
oxadiazole-containing hole-blocking material for organic light-emitting diodes: synthesis, crystal
structure, and device performance. Chem. Mater. 13(4): 1167–1173.
Wang, Q., Q.-S. Tian, Y.-L. Zhang, X. Tang and L.-S. Liao. 2019. High-efficiency organic light-emitting
GLRGHVZLWKH[FLSOH[KRVWV-0DWHU&KHP&±
https://t.me/med1917
Соседние файлы в папке Библиотека им академика М.И. Перельмана