Synthesis and characterization of arylacetylene derivative as solution processable organic semiconductors for organic thin-film transistors

Article abstract of DOI:10.1166/jnn.2016.13154

New arylacetylene derivative (4,7-bis((4-(thiophen-2-yl)phenyl)ethynyl)benzo[c][1,2,5]thiadiazole; 5) functionalized with thiophene and benzothiadiazole was synthesized and characterized as organic semiconductors for organic thin-film transistors (OTFTs). Compound 5 exhibited p-channel characteristics with carrier mobility as high as 10^-4 cm²/Vs and a current on/off ratio >10⁵ for top-contact/bottom-gate OTFT devices.

Full text of DOI:10.1166/jnn.2016.13154

Article
Journal of
Nanoscience and Nanotechnology
Vol. 16, 10331–10336, 2016
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Copyright © 2016 American Scientific Publishers
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Synthesis and Characterization of Arylacetylene
Derivative as Solution Processable Organic
Semiconductors for Organic Thin-Film Transistors
Hyekyoung Kim1ꢀ†, M. Rajeshkumar Reddy2ꢀ†, Guhyun Kwon1, Donghee Choi1,
Choongik Kim1ꢀ∗, and SungYong Seo2ꢀ∗
1Department of Chemical and Biomolecular Engineering, Sogang University, Seoul 121-742, Korea
2Department of Chemistry, Pukyong National University, Busan 608-737, Korea
New arylacetylene derivative (4,7-bis((4-(thiophen-2-yl)phenyl)ethynyl)benzo[c][1,2,5]thiadiazole; 5)
functionalized with thiophene and benzothiadiazole was synthesized and characterized as organic
semiconductors for organic thin-film transistors (OTFTs). Compound 5 exhibited p-channel char-
acteristics with carrier mobility as high as 10−4 cm2/Vs and a current on/off ratio >105 for top-
contact/bottom-gate OTFT devices.
Keywords: Organic Thin-Film Transistors, Arylacetylene, Benzothiadiazole, Self-Assembled
Monolayer.
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1. INTRODUCTION
p-type carrier mobilities (≤0.1 cm2/Vs).12 Therefore, it
is desirable to explore new arylacetylene derivatives that
show high electrical performance.
Organic semiconductors based on pi-conjugated small
molecules and polymers are widely studied because of
their potential application as essential components for
organic thin-film transistors (OTFTs).1–4 Numerous chem-
ical cores, including pentacene,5 oligothiophene,6 and
(hetero)acenes,7 have been developed and employed in
OTFT applications. Despite recent achievements, it is
desirable to develop new organic semiconductors. To
this end, conjugated arylacetylenes are a promising class
of semiconductors suitable for OTFT applications. Ary-
lacetylenes have been less investigated as compared to
other molecular cores. Conjugated triple-bond-containing
systems have gained much interest as a promising class
of semiconductors. This is due to the availability of effi-
cient synthetic protocols for alkynylation reactions, and
favorable steric and conformational advantages for orbital
delocalization.8–11 Appropriate functionalization of these
cores with electron-donating or electron-withdrawing func-
tional groups has been known to modulate their physi-
cal and electronic properties. For example, Silvestri et al.
reported solution-processable arylacetylenes with good
To this end, we have synthesized a novel arylacety-
lene derivative based on a benzothiadiazole core end-
functionalized with thiophene moieties (Fig. 1). Thiophene
and phenyl groups exhibit electron-donating characteris-
tics, while benzothiadiazoles represent electron-accepting
moieties. Donor-acceptor-donor units with connecting
carbon–carbon triple bonds enhance molecular rigidity and
pi-polarization, possibly resulting in large pi-conjugation
with high film crystallinity.13 The thermal, optical, and
electrochemical properties of the new compound were
measured. The molecular structure and HOMO/LUMO
energy levels of the compound were determined via den-
sity functional theory (DFT) calculations. Furthermore,
the new compound was employed as a semiconductor
film, as prepared by a solution process [solution shearing
(SS)], in a top-contact/bottom-gate OTFT, and the result-
ing devices were characterized. Finally, the morphology
and microstructure of the deposited films were character-
ized by atomic force microscopy (AFM) and X-ray diffrac-
tion (XRD). Our results revealed that films of 5 were
active as p-channel organic semiconductors with a carrier
∗Authors to whom correspondence should be addressed.
†These two authors contributed equally to this work.
J. Nanosci. Nanotechnol. 2016, Vol. 16, No. 10
1533-4880/2016/16/10331/006
doi:10.1166/jnn.2016.13154 10331

Synthesis and Characterization of Arylacetylene Derivative as Solution Processable Organic Semiconductors for OTFTs
Kim et al.
to give ((4-bromophenyl)ethynyl)trimethylsilane(1) as a
white solid (192 mg, 71.5%).11 1H NMR (400 MHz,
CDCl3ꢃ: ꢁ 7.40 (d, 8.4 Hz, 2H), 7.30 (d, 8.4 Hz, 2H),
0.24 (s, 0.22 Hz, 9H).
S
S
N
N
S
5
2.2.2. Synthesis of Trimethyl((4-(thiophen-2-yl)
Figure 1. Chemical structure of 4,7-bis((4-(thiophen-2-yl)phenyl)
ethynyl)benzo[c][1,2,5]thiadiazole (5).
phenyl)ethynyl)silane(2)
A mixture of ((4-bromophenyl)ethynyl)trimethylsilane
(1, 300 mg, 1.18 mmol), 2-thiophenboronic acid (2a,
180 mg, 1.4 mmol), and Pd(PPh3ꢃ4 (68 mg, 0.059 mmol)
was dissolved in tetrahydrofuran (10 mL) and 2 M aq.
Na2CO3 (1.8 mL, 3.6 mmol) was added. The reaction mix-
ture was refluxed for 12 h under N2 atmosphere. The crude
mixture was diluted with ethyl acetate, and filtered, and
then the residue was washed with ethyl acetate. The com-
bined filtrates were washed with distilled H2O. Organic
layer separated, dried over anhydrous MgSO4 and evap-
orated in vacuo. Then the crude product was purified by
column chromatography on silica gel to give trimethyl((4-
(thiophen-2-yl)phenyl)ethynyl)silane(2) as a pale yellow
solid (183 mg, 60.4%).12 1H NMR (400 MHz, CDCl3ꢃ:
ꢁ 7.52 (d, 8.04 Hz, 2H), 7.44 (d, 8.44 Hz, 2H), 7.31
(d, 3.64 Hz, 1H), 7.28 (d, 4.76 Hz, 1H), 7.06 (t, 8.8 Hz,
1H), 0.23 (s, 9H).
mobility as high as 10−4 cm2 V−1 −1, and a current on/off
s
ratio >105.
2. EXPERIMENTAL DETAILS
2.1. General Methods
Air and/or moisture sensitive reactions were carried out
under an N2 atmosphere in oven-dried glassware and with
anhydrous solvents. All chemicals were purchased from
commercial sources unless otherwise noted and used with-
out further purification. Solvents were freshly distilled
or dried by passing through an alumina column. Thin
layer chromatography was carried out on glass plates
coated with silica gel SiO2 60 F254 from Merck; visu-
alization with a UV lamp (254 nm) or by staining with
a p-anisaldehyde or potassium permanganate solution.
Flash chromatography was performed with silica gel SiO2
60 (0.040–0.063 ꢀm, 230–400 mesh), technical solvents,
and a head pressure of 0.2–0.4 bar. Proton (1H) and
carbon (13C) nuclear magnetic resonance (NMR) spec-
troscopy was performed on a JEOL ECP-400 spectrom-
eter at 400 MHz (1H) and 100 MHz (13C) at 294 K.
Chemical shifts are reported in ppm relative to the resid-
ual non-deuterated solvent (CDCl3: ꢁH = 7ꢂ26 ppm, ꢁC =
77ꢂ16 ppm). All 13C NMR spectra are proton decoupled.
The resonance multiplicity is described as s (singlet),
d (doublet), t (triplet), q (quartet), p (pentet), dd (dou-
blet of doublet), dt (doublet of triplet), td (triplet of dou-
blet), m (multiplet), and br (broad). High-resolution mass
spectrometry (HRMS) was measured on a JEOL JMS-700
spectrometer. Mass peaks are reported in m/z units.
2.2.3. Synthesis of 2-(4-ethynylphenyl)thiophene(3)
Trimethyl((4-(thiophen-2-yl)phenyl)ethynyl)silane (2, 100 mg,
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0.39 mmol) and 2 M KOH (5 mL) in methanol were
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dissolved in 5 mL of tetrahydrofuran. The reaction mix-
ture was stirred at room temperature for 1 h under N2
atmosphere. After completion of the reaction (indicated
by TLC), H2O and ethyl acetate were added. The organic
layer was separated, dried over anhydrous MgSO4 and
evaporated in vacuo. Then the crude product was purified
by column chromatography on silica gel to give 2-(4-
ethynylphenyl)thiophene(3) as a yellow solid (68 mg,
94.7%).13 1H NMR (400 MHz, CDCl3): ꢁ 7.56–7.54
(m, 2H), 7.49–7.47 (m, 2H), 7.32–7.28 (m, 2H), 7.07 (q,
4.76, 5.12 Hz, 1H), 3.12 (s, 1H).
Copyright: American Scientific Publishers
2.2.4. Synthesis of 4,7-Diiodobenzo[c]
2.2. Synthesis
2.2.1. Synthesis of ((4-bromophenyl)ethynyl)
[1,2,5]Thiadiazole(4)
Benzo[c][1,2,5]thiadiazole (4a, 1.0 g, 7.34 mmol), I2
(4.12 g, 16.23 mmol), and Ag2SO4 (1.29 g, 7.34 mmol)
were dissolved in 10 mL of conc. H2SO4. Result-
ing mixture was stirred at 110 ꢀC for 14 h. After
cooling to room temperature, the reaction mixture was
poured into ice water and the precipitate was col-
lected by filtration. The precipitate was dissolved in
CH2Cl2 and washed with aq. NaHSO3 solution and bine.
The organic layer was separated, dried over anhydrous
MgSO4 and evaporated in vacuo. The crude product
was purified by recrystallization in ethanol to afford
4,7-diiodobenzo[c][1,2,5]thiadiazole(4) as a yellow crystal
(1.5 g, 52.6%).14 1H NMR (400 MHz, CDCl3ꢃ: ꢁ 8.16
(s, 2H).
trimethylsilane(1)
1-Bromo-4-iodobenzene (1a, 300 mg, 1.06 mmol),
Pd(PPh3ꢃ4 (61.2 mg, 0.053 mmol), and CuI (20 mg,
0.11 mmol) were dissolved in 10 mL of triethylamine
and trimethylsilyl acetylꢀene (1b, 176 mL, 1.27 mmol)
was added slowly at 0 C. Then, reaction mixture was
stirred under N2 atmosphere for 5 h and trimethylamine
was distilled off under vacuo. The residue obtained
was taken up in ethyl acetate and washed with dis-
tilled water and brine. The organic layer was next dried
over anhydrous MgSO4 and evaporated in vacuo to
give the crude product. Then the crude product was
purified by flash column chromatography on silica gel
10332
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Kim et al.
Synthesis and Characterization of Arylacetylene Derivative as Solution Processable Organic Semiconductors for OTFTs
2.2.5. Synthesis of 4,7-Bis((4-(thiophen-2-yl)phenyl)
ethynyl)benzo[c][1,2,5]thiadiazole(5)
2-(4-Ethynylphenyl)thiophene (3, 100 mg, 0.54 mmol),
speed (6 mm/min). The solutioꢀn-sheared substrates were
placed in a vacuum oven at 90 C for 3 hr to remove the
residual solvent. Film thicknesses were characterized by
profilometer (DEKTAK-XT, Brucker) with a thickness in
the 20–50 nm range. Gold source and drain electrodes
(40 nm) were thermally evaporated through a shadow
mask with various channel lengths length (L; 50 ꢀm) and
width (W; 1000 ꢀm).
4,7-diiodobenzo[c][1,2,5]thiadiazole
(4,
104
mg,
0.26 mmol), Pd(PPh3ꢃ4 (16 mg, 0.013 mmol), and CuI
(5.4 mg, 0.028 mmol) were dissolved in 10 mL of tri-
ethylaꢀmine/THF (1:1). The reaction mixture was heated
at 60 C for 24 h under N2 atmosphere. After completion
of the reaction (indicated by TLC), solvent was removed
by reducing pressure. The crude mixture was dissolved
in CH2Cl2 and washed with water and brine solution.
Then, organic layer was separated, dried over anhydrous
MgSO4 and evaporated in vacuo. Then the crude prod-
uct was purified by column chromatography on silica
gel to give compound 5 as a yellow solid (84.8 mg,
66%).11ꢄ15 1H NMR (400 MHz, CDCl3ꢃ: ꢁ 7.79 (s, 2H),
7.64 (q, 12.84, 12.12 Hz, 8H), 7.37 (d, 3.68 Hz, 2H),
7.31 (dd, 4.76, 5.12 Hz, 2H), 7.09 (q, 4.76 Hz 2H).
13C NMR (100 MHz, CDCl3): ꢁ 155.09, 144.22, 135.84,
135.72, 133.76, 133.26, 133.16, 128.98, 127.01, 126.54,
126.43, 124.65, 124.58, 122.03, 117.88, 98.24, 87.02,
125.9, 124.5, 124.4, 120.3, 120.1, 109.6. HRMS-EI(m/z):
[M + Na+] calcd. for C30H16N2S3Na+, 523.0368; found,
523.0376.
2.5. Characterization
Thermogravimetric analyses (TGA, TA Instrument Q50-
1555) were performed on sample in a platinum crucible;
the sample was heated from 40 to 700 ꢀC at a heating rate
ꢀ
of 20 C min−1, while the chamber was purged continu-
ously with N2 gas at a rate of 100 mL min−1. Differential
scanning calorimetry (DSC) analyses (TA instrument Q20-
ꢀ
2487) were performed at a scan rate of 20 C min−1 from
ꢀ
40 to 350 C. The UV-visible spectra of the compound in
chloroform were obtained using JASCO V-530 spectrome-
ter with quartz cuvette over the special range 200–800 nm.
Cyclic voltammetry (CV) experiments were performed
with a conventional three-electrode configuration (glassy
carbon working electrode, platinum-wire counter elec-
trode, and Ag/AgCl reference electrode) with support-
ing electrolyte of tetrabutylammonium tetrafluoroborate in
the specified dry solvent on AUT302N Electrochemical
Analyzer (Autolab). All electrochemical potentials were
referenced to an Fc /Fc internal standard. The current–
voltage characteristics of fabricated OTFT devices were
measured at room temperature under vacuum using a
Keithley 4200 SCS. Carrier mobilities (ꢀ) were calculated
in the saturation regime by the formula, ꢀsat = ꢆ2IDSLꢃ/
ꢇWCiꢆVG − VTꢃ2ꢈ, where IDS is the source-drain current,
L is the channel length, W is the channel width, Ci
is the areal capacitance of the gate dielectric (Ci =
11ꢂ4 nF cm−2), VG is the gate voltage, and VT is the thresh-
old voltage.
2.3. Theoretical Calculation
Density functional theory (DFT) calculations on the
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present semiconductor were performed using the B3LYP
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(Becke’s 3 parameters employing the Lee-Yang-Parr) func-
tional and the 6-31G(d) basis set as implemented in
Gaussian 03W program.
2.4. Device Fabrication
Top-contact/bottom-gate organic thin-film transistors
(OTFTs) were fabricated on a heavily n-doped (100)
silicon wafers (resistivity <0.005 ꢅ·cm) with a thermally
grown silicon dioxide (300 nm SiO2) as dielectric layer.
The Si/SiO2 substrate was washed in an ultrasonic bath
using acetone for 10 min, dried using a N2 gun and
cleaned by air plasma for 5 min (Harrick Plasma, 18 W).
The general recipes were employed for the treatment
of PS-brush layer9 and OTS self-assembled monolayer20
on the Si/SiO2 substrates. Hydroxyl end-functionalized
polystyrene (Mn = 10 kg/mol, Polymer Source) was
employed for the formation of PS-brush layer. Semicon-
ducting layers were formed via solution-shearing (SS)
method. For the SS process, a few drops of semiconductor
solution were cast onto a heated substrate (1×2 cm2), and
the substrate was covered with a dewetting OTS-modified
top substrate.21 For the optimization of film-forming
process, various solvents including toluene, chloroben-
zene, p-xylene, 1,2,4-trichlorobenzene with concentration
(1 mg/mL) were employed. Solvent evaporation was
controlled by a deposition temperature (60% of the sol-
vent boiling point in centigrade) and a solution shearing
The surface morphology and film microstructure of thin
films was characterized using an atomic force microscope
(AFM, NX10, Park Systems) and X-ray diffraction (XRD,
Miniflex, Rigaku), respectively.
3. RESULTS AND DISCUSSION
3.1. Synthesis
The synthetic pathway for the preparation of 5 is illus-
trated in Scheme 1. First 2-(4-ethynylphenyl)thiophene (3)
was prepared in three steps, namely: Sonogashira
coupling of 1-bromo-4-iodobenzene (1a) and TMS-
acetylene (1b) to afford ((4-bromophenyl)ethynyl)tri-
methylsilane (2);14 followed by Suzuki coupling of this
compound and thiopheneboronic acid (2a) to afford tri-
methyl((4-(thiophen-2-yl)phenyl)ethynyl)silane (2);15 after
which the TMS group was deprotected to afford
2-(4-ethynylphenyl)thiophene (3).16
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10333

Synthesis and Characterization of Arylacetylene Derivative as Solution Processable Organic Semiconductors for OTFTs
Kim et al.
OH
B
Pd(PPh3)4
Pd(PPh3)4
HO
+
+
Br
I
Br
TMS
TMS
S
2M Na2CO3
CuI, TEA
0 oC, 5 h
THF, Reflux, 12 h
1a
1b
1
2a
TMS
S
2
S
N
N
4a
2M KOH/MeOH
THF, rt, 2 h
Ag2SO4
reflux, 14h
H2SO4, I2
I
Pd(PPh3)4
+
I
S
S
N
S
S
CuI, THF/TEA
60 oC, 24h
N
N
N
S
3
4
5
Scheme 1. Synthesis of 5.
Next, 4,7-diiodobenzo[c][1,2,5]thiadiazole (4) was syn-
thesized by direct iodination of benzo[c][1,2,5]thia-
diazole (4a).17
3.3. Theoretical Calculation
The molecular structure and HOMO/LUMO energy dis-
tribution of the arylacetylene derivative were determined
by DFT (B3LYP) calculations with 6-31G(d) basis sets
(Fig. 3). In 5, with arylacetylene moieties on both ends,
the HOMO was dispersed over the whole molecule. On the
otherhand, theLUMOwaslocalizedonthebenzothiadiazole
moiety. These results demonstrate the electron-accepting
character of the benzothiadiazole. The theoretically calcu-
lated band gap energy was 2.56 eV. This value is similar to
that determined from the UV-vis spectrum.
Finally, 3 and 4 were coupled by Sonogashira reaction
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to afford 5.18
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3.2. Thermal, Optical, and Electrochemical Properties
The thermal properties of the new arylacetylene derivative
were characterized by thermogravimetric analysis (TGA)
and differential scanning calorimetry (DSC). A sharp
endotherm at 251 ꢀC and weight loss (∼5%) upon heating
ꢀ
above 237 C were observed (Table I), indicating thermal
stability of 5. The optical absorption spectra in chloro-
form solution display ꢉmax values at 249, 328, and 438 nm
(Fig. 2). Hence, the HOMO–LUMO energy gap calculated
from the onset of the experimental optical absorption was
determined as 2.54 eV.
3.4. Thin-Film Transistor Characterization
Top-contact/bottom-gate OTFTs were fabricated using thin
films of 5 as semiconducting layers, via a solution pro-
cess method (SS). PS brush-coated SiO2/Si substrates
were used as the dielectric and gate. For the SS process,
Cyclic voltammetry (CV) measurements of 5 were per-
ꢀ
formed in o-C6H4Cl2 at 25 C. The compound exhibits
an oxidation peak at around +1.50 V (using fer-
rocene/ferrocenium as an internal standard at +0.73 V).
Hence, the HOMO energy level, determined by the con-
version of the oxidation potential using ferrocene as the
standard, was −5.51 eV. The LUMO energy levels were
calculated from the HOMO (CV measurements) and the
bandgap (UV-vis measurements), as illustrated in Table I.
1.0
0.8
0.6
0.4
0.2
0.0
Table I. Physical and electrochemical properties of the compound 5.
peak
DSC Tm
(ꢀC)
TGA
(ꢀC; 5%)
UV-Vis
ꢉmax (nm)a
E
Egap HOMO LUMO
200
400
600
ox
(V)b (eV)a
(eV)b
(eV)c
Wavelength (nm)
251
237
249, 328, 438 1.50 2.54
−5.51
−2.97
Figure 2. Optical spectra of 5 in chloroform solution.
J. Nanosci. Nanotechnol. 16, 10331–10336, 2016
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Kim et al.
Synthesis and Characterization of Arylacetylene Derivative as Solution Processable Organic Semiconductors for OTFTs
Figure 3. Molecular orbital surfaces of the HOMO and LUMO energy
levels of 5 determined from DFT calculations.
various conditions for the formation of thin films were
optimized. These include the solvents (toluene, chloroben-
zene, p-xylene, 1,2,4-trichlorobenzene), concentration of
solution, temperature of substrate, and shearing speed.
Gold electrodes were deposited through a shadow mask to
define the source and drain. Table II summarizes the OTFT
data (charge carrier mobility, current on/off ratio, and
threshold voltage). Solution-sheared films of 5 exhibited
p-channel activity with a carrier mobility of up to 1ꢂ0 ×
10−4 cm2/Vs, and a current on/off ratio >105. Solution-
sheared films of 5 exhibited p-channel activity with a car-
rier mobility of up to 1ꢂ0 × 10−4 cm2/Vs, and a current
on/off ratio > 105, as shown in Figure 4.
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TFT device performance parametersCboapseydriognhtth:inAmfilmesricofan Scientific Publishers
Table II.
compound 5 (ꢀ: carrier mobility, Ion/Ioff : current on/off ratio, VT: thresh-
old voltage).
Figure 5. (a) AFM topographic image (10 × 10 ꢀm2) of a thin film
fabricated by SS of 5 (Inset: ꢊ–2ꢊ XRD scan of the corresponding thin
film). Scale bar = 2 ꢀm. (b) Microscopy image of a solution-sheared thin
film. The white arrow represents the shearing direction; scale bar = 8 ꢀm.
Surface
Surface
ꢀ
VT
Method treatment Solvent temperature (ꢀC) (cm2/Vs) Ion/Ioff (V)
3.5. Thin-Film Microstructure and Morphology
The film microstructure and surface morphology of the
new solution-processed semiconductor thin films were
characterized using wide-angle ꢊ–2ꢊ XRD and AFM to
evaluate device performance. Figure 5(a) illustrates the
AFM surface morphology and conventional ꢊ/2ꢊ XRD
scan of the organic semiconductor thin film based on 5.
The XRD scan (Inset of Fig. 5(a)) reveals that the solution-
sheared thin films did not exhibit any significant Bragg
reflections. This is an indication of poor film texture.
Furthermore, the AFM image demonstrates a relatively ori-
ented crystalline morphology with a surface roughness of
∼11.0 nm for a 10.0 ꢀm × 10ꢂ0 ꢀm scan area. Specifi-
cally, grains in these thin films displayed preferred growth
direction on a locale scale, forming microscale rods with
evident terraced islands.
SS
PS-brush Toluene
60
1ꢂ0×10−4 4ꢂ7×105 −11
10–6
VDS = –100 V
10–8
0
–2
10–10
VG
=
0 V
VG = –20 V
V
V
V
G = –40 V
G = –60 V
G = –80 V
–4
–6
10–12
VG = –100 V
–100 –80–60 –40 –20
VDS (V)
0
10–14
–100
–50
0
VG (V)
4. CONCLUSION
New arylacetylene derivative with benzothiadiazole core
end-functionalized with phenylthiophene was synthesized
and characterized. Thin-film transistors fabricated from the
Figure 4. Representative transfer curve of the OTFT device based on
thin films of 5. (Inset: representative output curve of the corresponding
OTFT device).
J. Nanosci. Nanotechnol. 16, 10331–10336, 2016
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Synthesis and Characterization of Arylacetylene Derivative as Solution Processable Organic Semiconductors for OTFTs
Kim et al.
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mobility as high as 1ꢂ0 ×10−4 cm2/Vs.
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Acknowledgment: This study was supported by a
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Received: 28 November 2015. Accepted: 23 March 2016.
Delivered by Ingenta to: Adelaide Theological Library
IP: 141.101.201.88 On: Mon, 29 Aug 2016 21:03:22
Copyright: American Scientific Publishers
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J. Nanosci. Nanotechnol. 16, 10331–10336, 2016