A thermally stable anthracene derivative for application in organic thin film transistors

Article abstract of DOI:10.1016/j.orgel.2017.01.005

A novel multifunctional anthracene derivative 2,6-bis(dibenzo[b,d]furan-3-yl)anthracene) (BDBFAnt), by coupling anthracene moiety with dibenzo[b,d]furan units attached to its peripheral position, has been designed and synthesized for application in OTFT devices. Introduction of dibenzo[b,d]furan units in OTFTs is the first example and is highly innovative due to their suitable carrier transport ability, excellent thermal stability, fine film-forming property, rigid planarity and outstanding fluorescence. The fabricated OTFTs demonstrate a decent hole mobility (3.0?cm²/V s) and favorable green solid fluorescence with excellent thermal stability (up to 220?°C), which expound on the great potential of our material in organic electronics.

Full text of DOI:10.1016/j.orgel.2017.01.005

Accepted Manuscript
A thermally stable anthracene derivative for application in organic thin film transistors
Yang Zhao, Lijia Yan, Imran Murtaza, Xiao Liang, Hong Meng, Wei Huang
PII:
S1566-1199(17)30005-8
10.1016/j.orgel.2017.01.005
ORGELE 3917
DOI:
Reference:
To appear in: Organic Electronics
Received Date: 19 October 2016
Revised Date: 26 November 2016
Accepted Date: 6 January 2017
Please cite this article as: Y. Zhao, L. Yan, I. Murtaza, X. Liang, H. Meng, W. Huang, A thermally stable
anthracene derivative for application in organic thin film transistors, Organic Electronics (2017), doi:
10.1016/j.orgel.2017.01.005.
This is a PDF file of an unedited manuscript that has been accepted for publication. As a service to
our customers we are providing this early version of the manuscript. The manuscript will undergo
copyediting, typesetting, and review of the resulting proof before it is published in its final form. Please
note that during the production process errors may be discovered which could affect the content, and all
legal disclaimers that apply to the journal pertain.

ACCEPTED MANUSCRIPT

ACCEPTED MANUSCRIPT
A Thermally Stable Anthracene Derivative for
Application in Organic Thin Film Transistors
Yang Zhao, Lijia Yan, Imran Murtaza, Xiao Liang, Hong Meng*, Wei Huang
Key Lab for Flexible Electronics & Institute of Advanced Materials, Jiangsu National
Synergistic Innovation Centre for Advanced Materials (SICAM), Nanjing Tech University, 30
South Puzhu Road, Nanjing 211816 (China).
AUTHOR INFORMATION
Corresponding Author
*
Hong Meng Email: iamhmeng@njtech.edu.cn Tel: +86 187 0137 5998

ACCEPTED MANUSCRIPT
ABSTRACT
A novel multifunctional anthracene derivative 2,6-bis(dibenzo[b,d]furan-3-yl)anthracene)
BDBFAnt), by coupling anthracene moiety with dibenzo[b,d]furan units attached to its
(
peripheral position, has been designed and synthesized for application in OTFT devices.
Introduction of dibenzo[b,d]furan units in OTFTs is the first example and is highly innovative
due to their suitable carrier transport ability, excellent thermal stability, fine film-forming
properties, rigid planarity and outstanding fluorescence. The fabricated OTFTs demonstrate a
2
decent hole mobility (3.0 cm /V·s) and favorable green solid fluorescence with excellent thermal
stability (up to 220 °C), which expound on the great potential of our material in organic
electronics.
KEYWORDS: BDBFAnt, Dibenzo[b,d]furan, Thermal stability, Strong solid fluorescence
1
. INTRUCTION
During the last couple of decades, organic semiconductors (OSCs), as the active layer in
organic thin film transistors (OTFTs), have attracted much attention due to their promising
applications in large area and mechanically flexible electronics such as electronic textiles, radio
frequency identification tags and transparent electronics.[1-3] Indeed, a remarkable enhancement
has been achieved in the performance, especially p-type OSCs,[4] because extensive efforts have
been devoted to the improvement of OTFTs for both academic and industrial applications.[5, 6]
However, practical application of OTFTs such as integration into consumable electronic
equipment requiring exposure to temperatures above 100 °C is still challenging because of their

ACCEPTED MANUSCRIPT
low mobility and air and thermal instability.[7] To our delight, many groups have been focusing
on developing the thermally stable OSCs such as polythiophene derivatives,[8]
benzothieno[3,2,b]benzothiophene (BTBT) derivatives,[9-12] linear acenes[13] and so on. Takao
[9, 12, 13] et al has made massive research on developing the thermally stable OSCs based on
BTBT derivatives. They developed a novel semiconductor dinaphtho[2,3-b:2’,3’-f] thieno [3,2,-
b]thiophene (DNTT)[9] and provided evidence of thermal stability by demonstrating a steady
2
mobility of 1.2 cm /V•s in their TFTs after annealing up to 100 °C. In the same year, they also
reported TFTs based on DNTT derivatives (DPh-DNTT)[12] exhibiting a mobility of 1.6
2
cm /V•s with slight decrease in the mobility upon heating the TFTs up to a temperature of 250
°
C. In addition, Tian et al[10] developed a BTBT derivative (2,2'-bi[1]benzo-thieno[3,2-
2
b][1]benzothiophene) which presented mobility up to 2.12 cm /V•s and demonstrated high
thermal stability as evident from the slight degradation after annealing at temperature up to 250
°
C. Impressively, thermally stable OSCs have achieved a great breakthrough and OTFTs based
2
on DPh-BBTNDT [11] displayed high mobility (up to 7 cm /V•s) and excellent thermal stability
(up to 300 °C). However, these OSCs have the disadvantages of complex synthesis procedure of
the sophisticated reactants, which limits their application in devices.
According to an extensive research to date, anthracene derivatives are regarded as one of the
most potential candidates for OTFTs and OLEDs due to their inherent advantages such as ease in
chemical modification, excellent air stability, high mobility and high fluorescence.[6, 14-19] In
addition, it is known that an effective method to obtain OSCs with lager π-conjugation and
excellent thermal stability is oligomerization of small acenes.[10] Taking this into consideration,
we intend to introduce thermally stable fused aromatic rings such as dibenzofuran (DBF),
dibenzothiophene (DBT) [20, 21] into the anthracene core. Thereto, DBF moiety is widely

ACCEPTED MANUSCRIPT
applied in organic semiconductors particularly phosphorescent organic light-emitting diodes
(PhOLEDs)[22] due to its suitable carrier transport ability, excellent thermal stability, fine film-
forming properties, rigid planarity and outstanding fluorescence.[23-26] However, to our
knowledge analogous research on the OTFT devices is not yet reported, hence we take the lead
to combine anthracene moiety with DBF units to design the OSC for OTFT devices and aim to
increase the thermal stability and fluorescence. In this context, BDBFAnt, a new kind of
anthracene derivative, has been designed and synthesized via simple and efficient Suzuki
reaction. BDBFAnt exhibits high thermal stability, outstanding fluorescence and fine mobility.
From this point of view, BDBFAnt is regarded as a potential candidate for multifunctional
electronic devices requiring high mobility and outstanding fluorescence, such as organic light
emitting transistors which are multifunctional devices combining the current switching
amplification of OFET and the light emission functionality of OLED [27, 28] and electrically
pumped organic lasers [29-31] that require organic semiconductors with high fluorescence to
generate optical excitation and high carrier mobilities to ensure fast transport of the injected
charges to the recombination zone promoting further charge injection. The fabricated devices are
still far away from practical application due to shortage of organic semiconductors with both
high mobility and strong fluorescent emission. It remains a challenge to obtain OSCs with both
high mobility and good fluorescent emission because of the contradictory structural requirements.
Achieving high mobility always demands strong π-interactions and planar structure, while
obtaining high emission typically requires suppressing π-interactions to avoid exciton
quenching.[32]
Here, we envisioned a planar molecular structure by specifically designing the dibenzofuran
anthracene compound with dibenzo[b,d] furan moiety artificially substituted at 3 position. The

ACCEPTED MANUSCRIPT
rational motives to design the molecules are: (i) to use the DBF units at 2-, 6- position of
anthracene core in order to extend the molecular π conjugation and tune the molecular packing,
(ii) to increase the fluorescence and the thermal stability of anthracene core.
Scheme 1 illustrates the synthetic route to our new organic semiconductor material. The final
yellow colored product was synthesized via Suzuki coupling and was purified three times by
gradient sublimation. The compound was characterized single crystal X-Ray analysis, elemental
analysis and high-resolution mass spectrometry (see more details in ESI)
Scheme 1 synthetic route to compound BDBFAnt
2
. RESTULT AND DISCUSSION
The detailed synthesis routes, characterization of BDBFAnt and the OTFT device fabrication
steps are described in the supporting information.
The thermal properties of BDBFAnt were investigated by thermogravimetric analysis (TGA) and
differential scanning calorimetry (DSC). As shown in Fig. S1 (A), the TGA curves illustrate the

ACCEPTED MANUSCRIPT
decomposition temperature (5% weight loss) of ~ 460 °C under both nitrogen and atmosphere
environment, which is an evidence of good thermal stability.[12] Fig. S1 (B) shows the DSC of
BDBFAnt, there is no peak in the DSC scan from 25 to 360 °C, whereas, sharp melting peaks at
~
390 °C can be seen which correspond to the phase transition (Fig. S1 (C)). These results
exhibit excellent thermal stability of our material.
Fig. 1 (A) UV-Vis (red) and PL spectra (blue) of BDBFAnt in thin films (B) Cyclic
Voltammetry of BDBFAnt in thin films.
The optical properties of the thermally evaporated thin films of BDBFAnt were studied using
UV-Visible absorption and photoluminescence (PL) spectra. As depicted in Fig. 1(A), the energy
band gap of 2.61 eV is evaluated from the absorption onset of 475 nm. The peak positions of UV
absorption from 400 to 500 nm are similar to anthracene. Whereas, the new peaks in the wave
length range of 300 to 380 nm is ascribed to the absorption of end-capping dibenzofuran units. In
PL spectra (Fig. 1 (A)), BDBFAnt thin films exhibit strong greenish fluorescence and the
florescent quantum efficiency (QE) of about 49 % (Fig. S2). As shown in Fig S3 the PL spectra
of BDBFAnt in the thin film shows red-shifted emission as compared to that of anthracene. It is
known that the anthracene exhibits blue fluorescence and the PLQY of anthracene in ethanol is

ACCEPTED MANUSCRIPT
around 27% [33], so the introduction of DBF groups significantly increase the intensity of
fluorescence. But, the PLQY of BDBFAnt is lower than previously reported 9,10-
bis(dibenzo[b,d]furan-4-yl)anthracene [34], due to its planar structure and strong π-interactions
which generate exciton quenching.[6, 35] The electrochemical properties of the thin films on
GCE in CH Cl /TBAPF solution were analyzed. As shown in Fig. 1 (B), the HOMO level is
2
2
6
calculated to be -5.78 eV, about 0.7 eV more negative than pentacene (-5.1 eV) , 0.4 eV more
negative than bi-BTBT and at the same level as anthracene (~5.79 eV),[15] providing the
evidence of higher oxidation stability. It has been proved that transistors based on materials with
HOMO level range from -4.5 to -5.0 eV are unstable when exposed to ambient atmosphere
because these materials are susceptible to oxidative doping.[36] The optical and electrochemical
properties of BDBFAnt are summarized in Table S1.
With the intention to gain insight into geometry and stabilization effects of DBF moiety, we
grew the single crystal via vapor deposition and, gratifyingly, the single crystal X-ray diffraction
results are demonstrated in Fig. 2 (CCDC 1506173). The results reveal that the molecular
packing of BDBFAnt is a typical herringbone structure, possessed by most of the high mobility
organic semiconductors. From the X-ray Crystallographic data, the BDBFAnt crystal belongs to
monoclinic I/ (2/c) space group with crystal parameters of a = 5.981 Å, b = 7.485 Å, c = 53.68 Å,
o
β = 91.71 . As shown in Fig. 2(D), C-H-π interactions (distance: 2.88 Å) are observed between
every single molecule and its adjacent molecules. However, the anthracene crystal belongs to
monoclinic P/ (2 /n) space group with lattice constants a = 8.553 Å, b = 6.021 Å, c = 22.333 Å, β
1
o
=
124.54 . Moreover, multi C-H-π interactions (distance: ~ 2.78 Å) are observed between every
anthracene molecule and its nearest molecules.[37] The BDBFAnt molecule displays a nearly
planar, symmetric molecular geometry, which leads to effective expansion of π-conjugation, also

ACCEPTED MANUSCRIPT
proved by an almost planar backbone structure of BDBFAnt with very low torsion angles of
6
.01° and 1.72°. Additional π-conjugation, coplanarity and strong intermolecular interactions
play the leading role in the carrier charge mobility of organic semiconductors.[38]
Fig. 2 (A) Molecular length and two torsion angles (B) packing structure projected along a-axis
(C) herringbone packing (D) short contacts in BDBFAnt
To study the charge transport properties, OTFT devices were fabricated with a top contact
geometry. The thin films (40 nm) were deposited on Si/SiO (200 nm) substrates modified by
2
OTS at different substrate temperatures via vacuum deposition and then gold was evaporated as
the source/drain electrodes. The performance of devices was measured by Angilent 1500B
parameter analyzer under ambient conditions. Representative transfer and output curves at
different substrate temperatures are demonstrated in Fig. 3 and the results are summarized in
Table 1. From the results it is clear that the substrate temperature has a significant influence on
the performance of BDBFAnt TFTs. The devices grown on OTS-treated substrate at 80 °C
2
5
exhibit the best field effect mobility of 3.0 cm /V s, current on/off ratio (Ion/Ioff) of about 8×10 ,
and the threshold voltage (V ) of nearly -37 V. We notice that the work function of gold was
T
noticeably higher than the HOMO level, creating a noteworthy contact resistance between the
semiconductor layer and the gold electrode, which restricts the device performance particularly
the linear regime[10] and result in a relatively large threshold. With the increased substrate
temperature, the performance of OTFTs enhances sharply under 80 °C. However, when the

ACCEPTED MANUSCRIPT
substrate temperature approaches 100 °C, the mobility of BDBDFAnt TFTs shows slight
degradation. As shown in Fig 3(E)-(H), the output curves of the transistors exhibit decrease in
current as the drain voltage, this behavior was ascribed to the existence of O and H O at the
2
2
interface of semiconductor-dielectric.[39]
Fig. 3 Typical transfer and output curves of OTFTs at (A) (E) T =25℃ , (B) (F) T =60℃ , (C)
sub
sub
(
G) T =80℃ , (D) (H) T =100℃
sub sub
Table 1 Performance parameters of BDBFAnt OTFTs
ꢀmax
ꢀ
Tsub
2
2
V (V)
th
I /I
on off
(cm /V·s)
(cm /V·s)
5
6
6
6
6
2
6
8
1
5 °C(R.T.) 0.89
0.59 ± 0.22 -35 to -45 10 -10
5
0 °C
0 °C
00 °C
1.63
3.01
2.04
1.21 ± 0.28 -35 to -45 10 -10
5
2.53 ± 0.36 -35 to -45 10 -10
5
1.57 ± 0.30 -35 to -45 10 -10

ACCEPTED MANUSCRIPT
Since morphology, crystallinity and preferred orientation are the crucial elements influencing
the charge carrier transport in OTFTs, the thin films of BDBFAnt deposited on OTS-modified
Si/SiO were characterized by atomic force microscope (AFM) and X-Ray diffraction (XRD). As
2
illustrated in Fig. 4 (A)-(D), the substrate temperatures have a significant effect on the surface
morphology, which are supposed to affect the corresponding charge transport properties of the
films. The step heights of the crystalline terraced structure in the AFM images can be clearly
seen which is in good agreement with the extended molecular layers, indicating that the thin
films of BDBFAnt are grown layer by layer. Likewise, the obtained d-space (2.63 nm) is nearly
consistent with the length of the BDBFAnt molecule (2.58 nm), well in agreement with the
results of AFM images. The results indicate that the molecules are almost perpendicular to the
SiO substrate and form a packed structure, which is actually a widespread characteristic of most
2
of the high mobility organic semiconductors. We can see the dendrite growth in the AFM images,
but with the increase in substrate temperature, the dendrites become less obvious and the films of
BDBFAnt present large grain sizes with well-defined terraces with the increase in substrate
temperature. However, when the Tsub=100 °C, we notice that some subtle cracks (Fig. S4 white
arrow) appear in the thin films, which may be the reason for the degradation of mobility.
Additionally, the grain boundaries become larger and deeper, which could be unfavorable for
charge transport.[40] As shown in Fig. 4 (F), majority of the main peaks in the thin films XRD
patterns can be identified as (0 0 h) planes which are in agreement with the single crystal X-Ray
diffraction. Similarly, as the substrate temperature increases, the peaks (0 0 4), (0 0 6) and (0 0 8)
become much more intense than the peak (0 0 2), indicating that the orientation of the molecules
is optimal, in favor of carrier transport. At the same time, we notice that the intensities of the
peaks such as (1 1 2) and (1 1 4) increase when the substrate temperature is raised, illustrating

ACCEPTED MANUSCRIPT
that there is another new orientation. Furthermore, it is easy to observe that the intensity of the
peaks at Tsub = 80 °C is the lowest among the peaks at other substrate temperatures. The best
performance of the devices at Tsub = 80 °C, indicates that the new orientation of the molecules is
not suitable for carrier transport. These changes may be the reason for the charge mobility value
exhibits the best at 80 °C and decreases when the substrate temperature goes either direction.[41]
Fig. 4 AFM images of the semiconductor films deposited on OTS-treated wafer substrate at (A)
R.T., (B) 60 °C, (C) 80 °C, (D) 100°C (E) step height of terrace at 80 °C (F) XRD of the thin
films deposited at R. T., 60 °C, 80 °C, 100°C
The thermal stability of BDBFAnt TFTs was investigated by annealing the devices (Tsub
0 °C) in a glove box at selected temperatures for 30 minutes. Then the devices were allowed to
cool to R.T. and measurements were performed. As shown in Fig. 5 (A), at annealing
=
8

ACCEPTED MANUSCRIPT
temperatures below 180 °C, no obvious degradation in mobilities is observed. Whereas, at
annealing temperature of 220 °C, the performance of OTFTs based on BDBFAnt is slightly
2
decreased (from 3.0 to 1.8 cm /V•s), which proves the excellent thermal stability of BDBFAnt-
based devices. The performance of BDBFAnt TFTs show dramatic decrease at the annealing
temperature up to 240 °C. Consequently, BDBFAnt is among one of the highest mobility
materials with excellent thermal stability for OTFTs based on anthracene derivatives.
In order to investigate the effect of annealing temperature on the polycrystalline thin films of
BDBFAnt, the thin films were studied using XRD, AFM, PL, UV-Vis respectively. As shown in
Fig. 5 (B), when the annealing temperature is below 180 °C, it can be clearly seen that the XRD
data exhibit almost the same peaks. Nevertheless, the intensity of peaks is drastically decreased
after the annealing treatment up to 220 °C, suggesting that the crystalline quality was not good.
The results reveal that the degradation of mobilities is attribute to poor ordering of the thin films.
Interestingly, we found that annealing at 180 °C did not cause any spectral change in the PL
spectra, however when the annealing temperature is increased to 220 °C, the intensity of ~610
nm is increased in Fig. 5 (C). Similarity the UV-Vis spectra (Fig. 5(D)) illustrate a corresponding
change. The appearance of such an additional emission band upon heating has been attributed to
spontaneous aggregation and excimer formation as the origin of low-energy emission [42-44],
which impeded the mobility of charge carriers. Likewise, as shown in Fig. S5, the terraces of
BDBFAnt films are almost the same at the annealing temperature below 220 °C. Whereas we
notice that BDBFAnt molecules are gradually aggregated into thicker grains resulting a
significant change in the morphology when the annealing treatment is above 220 °C. It is
evidenced by analyzing the height profiles of grains in Fig. S6. With the increase of annealing
temperature, all BDBFAnt molecules exhibit aggregation more quickly, leading to rather thicker

ACCEPTED MANUSCRIPT
grains.[45] These phenomena of aggregation into thicker grains could result in the degradation in
the performance of OFETs based on BDBFAnt.
Fig.5 (A) The effect on mobility of different annealing temperature (B) The effect on XRD of
different annealing temperature (C) The effect on PL of different annealing temperature (D) The
effect on UV of different annealing temperature
3
. CONCLUSION
In summary, by architecturally introducing the substituent at 3 position, we have designed and
synthesized a novel semiconductor material based on anthracene derivative for application in
OTFTs. To the best of our knowledge introduction of DBF moiety is the first ever example to
exhibit excellent thermal stability not only as a compound itself but also as thin films used in
OTFTs, which gives a particular research direction. Moreover, a decent hole mobility of up to
2
3
.0 cm /V•s is achieved for the thin film transistors with excellent thermal stability at
temperature up to 220 °C. Furthermore, the BDBFAnt demonstrates a green fluorescence when
exposed at the wavelength of 365 nm. Therefore, due to this property of high mobility and strong
fluorescence along with excellent thermal stability, BDBFAnt may be employed in
multifunctional device applications in future.

ACCEPTED MANUSCRIPT
ACKNOWLEDGMENT
This work was supported by the National Research Foundation for the Doctoral Program
20133221110004), NSFC (51373075), Shenzhen Key Laboratory of Shenzhen Science and
(
Technology Plan (ZDSYS20140509094114164), Provincial Science and technology project of
Guangdong Province (2015B090914002; 2014B090914003), National Basic Research Program
of China (973 Program, No. 2015CB856505; 2015CB932200), and Guangdong Talents Project,
Guangdong Academician Workstation (2013B090400016).
Appendix A. Supplementary data
Supplementary data associated with this article can be found at in the online version.
REFERENCES
[
1] H. Dong, X. Fu, J. Liu, Z. Wang, W. Hu, 25th anniversary article: key points for high-
mobility organic field-effect transistors, Adv. Mater., 25 (2013) 6158-6183.
2] R. Schmidt, S. Gottling, D. Leusser, D. Stalke, A.-M. Krause, F. Wurthner, Highly soluble
acenes as semiconductors for thin film transistors, J. Mater. Chem., 16 (2006) 3708-3714.
3] P. Wolfer, M.L. Santarelli, L. Vaccaro, L. Yu, T.D. Anthopoulos, P. Smith, N. Stingelin, A.
[
[
Marrocchi, Influence of molecular architecture and processing on properties of semiconducting
arylacetylene: Insulating poly(vinylidene fluoride) blends, Org. Electron., 12 (2011) 1886-1892.
[4] D. Zhang, L. Zhao, Y. Zhu, A. Li, C. He, H. Yu, Y. He, C. Yan, O. Goto, H. Meng, Effects of
p-(trifluoromethoxy)benzyl and p-(trifluoromethoxy)phenyl molecular architecture on the
performance of naphthalene tetracarboxylic diimide-based air-stable n-type semiconductors,
ACS Appl. Mater. Inter., 8 (2016) 18277-18283.
[5] Y. He, M. Sezen, D. Zhang, A. Li, L. Yan, H. Yu, C. He, O. Goto, Y.L. Loo, H. Meng, High
performance OTFTs fabricated using a calamitic liquid crystalline material of 2-(4-Dodecyl
phenyl)[1]benzothieno[3,2-b][1]benzothiophene, Adv. Electron. Mater., (2016) 1600179.
[6] A. Dadvand, W.-H. Sun, A.G. Moiseev, F. Bélanger-Gariépy, F. Rosei, H. Meng, D.F.
Perepichka, 1,5-, 2,6- and 9,10-distyrylanthracenes as luminescent organic semiconductors, J.
Mater. Chem. C., 1 (2013) 2817.
[7] A.K. Tripathi, M. Heinrich, T. Siegrist, J. Pflaum, Growth and electronic transport in 9,10-
diphenylanthracene single crystals-An organic semiconductor of high electron and hole mobility,
Adv. Mater., 19 (2007) 2097-2101.
[8] M.C. Hwang, J.W. Jang, T.K. An, C.E. Park, Y.H. Kim, S.K. Kwon, Synthesis and
characterization of new thermally stable poly(naphthodithiophene) derivatives and applications
for high-performance organic thin film transistors, Macromolecules, 45 (2012) 4520-4528.
[9] K. Kuribara, H. Wang, N. Uchiyama, K. Fukuda, T. Yokota, U. Zschieschang, C. Jaye, D.
Fischer, H. Klauk, T. Yamamoto, K. Takimiya, M. Ikeda, H. Kuwabara, T. Sekitani, Y.L. Loo,

ACCEPTED MANUSCRIPT
T. Someya, Organic transistors with high thermal stability for medical applications, Nat.
Commun., 3 (2012) 723.
[10] H. Yu, W. Li, H. Tian, H. Wang, D. Yan, J. Zhang, Y. Geng, F. Wang,
Benzothienobenzothiophene-based conjugated oligomers as semiconductors for stable organic
thin-film transistors, ACS Appl. Mater. Inter., 6 (2014) 5255-5262.
[11] M. Abe, T. Mori, I. Osaka, K. Sugimoto, K. Takimiya, Thermally, operationally, and
environmentally stable organic thin-film transistors based on bis[1]benzothieno[2,3-d:2',3'-
d']naphtho[2,3-b:6,7-b']dithiophene derivatives: effective synthesis, electronic structures, and
structure–property relationship, Chem. Mater., 27 (2015) 5049-5057.
[12] T. Yokota, K. Kuribara, T. Tokuhara, U. Zschieschang, H. Klauk, K. Takimiya, Y.
Sadamitsu, M. Hamada, T. Sekitani, T. Someya, Flexible low-voltage organic transistors with
high thermal stability at 250 degrees C, Adv. Mater., 25 (2013) 3639-3644.
[13] K. Fukuda, T. Yokota, K. Kuribara, T. Sekitani, U. Zschieschang, H. Klauk, T. Someya,
Thermal stability of organic thin-film transistors with self-assembled monolayer dielectrics,
Appl. Phys. Lett., 96 (2010) 053302.
[
14] L. Jiang, W. Hu, Z. Wei, W. Xu, H. Meng, High-performance organic single-crystal
transistors and digital inverters of an anthracene derivative, Adv. Mater., 21 (2009) 3649-3653.
15] J. Liu, H. Dong, Z. Wang, D. Ji, C. Cheng, H. Geng, H. Zhang, Y. Zhen, L. Jiang, H. Fu, Z.
Bo, W. Chen, Z. Shuai, W. Hu, Thin film field-effect transistors of 2,6-diphenyl anthracene
[
(DPA), Chem. Commun., 51 (2015) 11777-11779.
[16] X. Zhang, G. Zhao, Y. Zhen, Z. Tu, P. He, Y. Yi, H. Dong, W. Hu, The position effect of an
ethynyl spacer on the carrier mobility of anthracene derivatives, J. Mater. Chem. C., 3 (2015)
368-5371.
17] K. Ito, T. Suzuki, Y. Sakamoto, D. Kubota, Y. Inoue, F. Sato, S. Tokito, Oligo(2,6‐
5
[
anthrylene)s: Acene-oligomer approach for organic field-effect transistors, Angew. Chem. Int.
Edit., 115 (2003) 1191-1194.
[
18] H. Dong, C. Wang, W. Hu, High performance organic semiconductors for field-effect
transistors, Chem. Commun., 46 (2010) 5211-5222.
19] L. Yan, Y. Zhao, H. Yu, Z. Hu, Y. He, A. Li, O. Goto, C. Yan, T. Chen, R. Chen, Y.-L.
[
Loo, D.F. Perepichka, H. Meng, W. Huang, Influence of heteroatoms on the charge mobility of
anthracene derivatives, J. Mater. Chem. C., 4 (2016) 3517-3522.
[
20] L. Wang, Z.-Y. Wu, W.-Y. Wong, K.-W. Cheah, H. Huang, C.H. Chen, New blue host
materials based on anthracene-containing dibenzothiophene, Org. Electron., 12 (2011) 595-601.
21] C. Han, Z. Zhang, H. Xu, S. Yue, J. Li, P. Yan, Z. Deng, Y. Zhao, P. Yan, S. Liu, Short-axis
[
substitution approach selectively optimizes electrical properties of dibenzothiophene-based
phosphine oxide hosts, J. Am. Chem. Soc., 134 (2012) 19179-19188.
[22] C. Han, G. Xie, H. Xu, Z. Zhang, D. Yu, Y. Zhao, P. Yan, Z. Deng, Q. Li, S. Liu, Towards
highly efficient blue-phosphorescent organic light-emitting diodes with low operating voltage
and excellent efficiency stability, Chem-Eur. J., 17 (2011) 445-449.
[23] C.W. Lee, J.A. Seo, M.S. Gong, J.Y. Lee, The effect of the substitution position of
dibenzofuran on the photophysical and charge ‐ transport properties of host materials for
phosphorescent organic light‐emitting diodes, Chem-Eur. J., 19 (2013) 1194-1198.
[24] S.C. Dong, C.H. Gao, Z.H. Zhang, Z.Q. Jiang, S.T. Lee, L.S. Liao, New
dibenzofuran/spirobifluorene hybrids as thermally stable host materials for efficient
phosphorescent organic light-emitting diodes with low efficiency roll-off, Phys. Chem. Chem.
Phys., 14 (2012) 14224-14228.

ACCEPTED MANUSCRIPT
[25] L. Zhang, S.-C. Dong, C.-H. Gao, X.-B. Shi, Z.-K. Wang, L.-S. Liao, Origin of improved
stability in green phosphorescent organic light-emitting diodes based on
dibenzofuran/spirobifluorene hybrid host, Appl. Phys. A., 118 (2014) 381-387.
26] Y. Shi, K. Hou, Y. Wang, K. Wang, H. Ren, M. Pang, F. Chen, S. Zhang, Two
a
[
methoxyaniline-substituted dibenzofuran derivatives as hole-transport materials for perovskite
solar cells, J. Mater. Chem. A., 4 (2016) 5415-5422.
[27] R. Capelli, S. Toffanin, G. Generali, H. Usta, A. Facchetti, M. Muccini, Organic light-
emitting transistors with an efficiency that outperforms the equivalent light-emitting diodes, Nat.
Mater., 9 (2010) 496-503.
[
28] F. Dinelli, R. Capelli, M.A. Loi, M. Murgia, M. Muccini, A. Facchetti, T.J. Marks, High-
mobility ambipolar transport in organic light-emitting transistors, Adv. Mater., 18 (2006) 1416-
420.
29] H. Kim, N. Schulte, G. Zhou, K. Mullen, F. Laquai, A high gain and high charge carrier
1
[
mobility indenofluorene-phenanthrene copolymer for light amplification and organic lasing,
Adv. Mater., 23 (2011) 894-897.
[
30] A.J. Kuehne, M.C. Gather, Organic lasers: recent developments on materials, device
geometries, and fabrication techniques, Chem. Rev., (2016).
31] J. Liu, H. Zhang, H. Dong, L. Meng, L. Jiang, L. Jiang, Y. Wang, J. Yu, Y. Sun, W. Hu,
A.J. Heeger, High mobility emissive organic semiconductor, Nat. Commun., 6 (2015) 10032.
32] C. Zhang, P. Chen, W. Hu, Organic light-emitting transistors: materials, device
configurations, and operations, Small, 12 (2016) 1252-1294.
33] W.H. Melhuish, Quantum efficiencies of fluorescence of organic substances: effect of
[
[
[
1
solvent and concentration of the fluorescent solute , J. Phys. Chem., 65 (1961) 229-235.
34] H.W. Lee, S. Jeong, S.E. Lee, Y.K. Kim, S.S. Yoon, Blue emitting materials containing
[
dibenzo[b,d]furan and dibenzo[b,d]thiophene for organic light-emitting diodes, Jap. J. Appl.
Phys., 55 (2016) 06GK07.
[35] J. Lee, H. Jung, H. Shin, J. Kim, D. Yokoyama, H. Nishimura, A. Wakamiya, J. Park,
Excimer emission based on the control of molecular structure and intermolecular interactions, J.
Mater. Chem. C., 4 (2016) 2784-2792.
[36] I. McCulloch, C. Bailey, M. Giles, M. Heeney, I. Love, M. Shkunov, D. Sparrowe, S.
Tierney, Influence of molecular design on the field-effect transistor characteristics of
terthiophene polymers, Chem. Mater., 17 (2005) 1381-1385.
[
37] B. Marciniak, V. Pavlyuk, Crystal Structure of a Metastable Anthracene Modification,
Grown from the Vapor Phase, Mol. Cryst. Liq. Crys., 373 (2002) 237-250.
38] D. Käfer, L. Ruppel, G. Witte, C. Wöll, Role of molecular conformations in rubrene thin
film growth, Phys. Rev. Lett., 95 (2005) 166602.
39] D. Shukla, S.F. Nelson, D.C. Freeman, M. Rajeswaran, W.G. Ahearn, D.M. Meyer, J.T.
[
[
Carey, Thin-film morphology control in naphthalene-diimide-based semiconductors: high
mobility n-type semiconductor for organic thin-film transistors, Chem. Mater., 20 (2008) 7486-
7
491.
[40] Y. Qiao, Y. Guo, C. Yu, F. Zhang, W. Xu, Y. Liu, D. Zhu, Diketopyrrolopyrrole-containing
quinoidal small molecules for high-performance, air-stable, and solution-processable n-channel
organic field-effect transistors, J. Am. Chem. Soc., 134 (2012) 4084-4087.
[41] H. Meng, F. Sun, M.B. Goldfinger, F. Gao, D.J. Londono, W.J. Marshal, G.S. Blackman,
K.D. Dobbs, D.E. Keys, 2,6-Bis[2-(4-pentylphenyl)vinyl]anthracene:ꢁ A Stable and High Charge

ACCEPTED MANUSCRIPT
Mobility Organic Semiconductor with Densely Packed Crystal Structure, J. Am. Chem. Soc.,
1
28 (2006) 9304-9305.
[42] X. Gong, P.K. Iyer, D. Moses, G.C. Bazan, A.J. Heeger, S.S. Xiao, Stabilized blue emission
from polyfluorene-based light-emitting diodes: elimination of fluorenone defects, Adv. Funct.
Mater., 13 (2003) 325-330.
[43] J.L. Brédas, D. Beljonne, J. Cornil, J.P. Calbert, Z. Shuai, R. Silbey, Electronic structure of
π-conjugated oligomers and polymers: a quantum–chemical approach to transport properties,
Synthetic. Met., 125 (2001) 107-116.
[
44] W.L. Yu, J. Pei, W. Huang, A.J. Heeger, Spiro‐functionalized polyfluorene derivatives as
blue light-emitting materials, Adv. Mater., 12 (2000) 828-831.
45] G. Yoshikawa, J.T. Sadowski, A. Al-Mahboob, Y. Fujikawa, T. Sakurai, Y. Tsuruma, S.
[
Ikeda, K. Saiki, Spontaneous aggregation of pentacene molecules and its influence on field effect
mobility, Appl. Phys. Lett., 90 (2007) 251906.

ACCEPTED MANUSCRIPT
A novel anthracene derivative BDBFAnt has been designed and synthesized for
application in OTFT devices.
ꢀ
ꢀ
ꢀ
ꢀ
BDBFAnt exhibits excellent thermal stability not only as a compound itself but
also as thin films for OTFTs
The BDBFAnt demonstrates a decent hole mobility with excellent thermal
stability.
The BDBFAnt demonstrates outstanding solid green fluorescence
.