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www.rsc.org/materials Volume 22 | Number 35 | 21 September 2012 | Pages 1806518672

Journal of Materials Chemistry

Research highlight from Prof. O-Pil Kwons group at As featured in:
the Department of Molecular Science and Technology,
Ajou University, Korea.

Title: Polyaniline films doped with ladder-type sulfonated

polyphenylsilsesquioxane and unusual dependence of their
electrical conductivity on temperature

Conducting polyaniline films doped with linear ladder-type

sulfonated polyphenylsilsesquioxane (S-PPSQ) exhibited
high-temperature stable electrical conductivity and unusual
negative temperature coefficient of resistance behavior.
See E.-Y. Hong et al.,
J. Mater. Chem., 2012, 22, 18151.
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Polyaniline films doped with ladder-type sulfonated polyphenylsilsesquioxane

and unusual dependence of their electrical conductivity on temperature
Eun-Young Hong,a Suck-Hyun Lee,a Dong-Ki Lee,b Seung-Seok Choi,b Kyung-Youl Baek,b
Seung-Sang Hwangb and O-Pil Kwon*a
Received 6th April 2012, Accepted 21st June 2012
DOI: 10.1039/c2jm32158k

We report on conducting polyaniline (PANI) films doped with a thermally stable polymer dopant,
linear ladder-type sulfonated polyphenylsilsesquioxane (S-PPSQ). The PANI/S-PPSQ films exhibited
high-temperature stable electrical conductivity. With a heat treatment at 120
C, the electrical
conductivity of conventional PANI films doped with the molecular dopant camphorsulfuric acid (CSA)
rapidly decreased to half of its initial value, while that of PANI/S-PPSQ films were relatively
unaffected. Moreover, PANI/S-PPSQ films with high electrical conductivity exhibited unusual negative
temperature coefficient of resistance (TCR) values above room temperature, in contrast to
conventional PANI/CSA films that exhibited positive TCR values. By using a solution blend of PANI/
S-PPSQ and PANI/CSA with negative and positive TCR values, respectively, we successfully
demonstrated control of TCR behavior. Therefore, PANI/S-PPSQ materials are very promising for
organic electronic applications.

Introduction Here, we report on highly stable conducting polyaniline

Nowadays, organic electronic devices require low-cost, flexible
integrated electronic components such as embedded resistors and
capacitors, electrodes, and thermistors.14 Because of the benefits
of easy processability and low-cost printing technologies such as
screen, micro-contact, and ink-jet printing techniques,5 solution-
processable organic conducting polymers are becoming more
important for various electronic applications.68 Since most
conducting polymers exhibit low solubility, many studies have
focused mainly on enhancing the processability and electrical
conductivity.917 However, temperature-dependent characteris-
tics, which are important in the development of fabrication
processes and for increasing the lifetime of devices, have seldom
been investigated. During the fabrication processes of electronic
devices, electronic components are exposed to high-temperature
processes such as the soft- and hard-baking of photoresists as
well as soldering.18 Moreover, mobile electronic devices are
frequently operated under harsh conditions such as high
temperatures or strong sunlight. Therefore, high temperature-
stable electrical conductivity (or resistance) of conducting poly-
mers is a challenging topic for improving the fabrication process
and increasing the lifetime of devices.
a
Department of Molecular Science and Technology, Ajou University,
Suwon 443-749, Korea. E-mail: opilkwon@ajou.ac.kr
b
Polymer Hybrids Center, Korea Institute of Science and Technology, 39-1
Hawolgok-dong, Seongbuk-gu, Seoul 136-791, Korea
Electronic supplementary information (ESI) available: Details of
synthesis of S-PPSQ and physical properties. See DOI:
10.1039/c2jm32158k
(PANI) films doped with a thermally stable polymer dopant, a
linear ladder-type sulfonated polyphenylsilsesquioxane
(S-PPSQ, see Fig. 1). Compared to PANI films doped with the
conventional molecular dopant camphorsulfuric acid (CSA),
those doped with S-PPSQ demonstrated enhanced stability of
electrical conductivity with a heat treatment at high tempera-
tures. Moreover, PANI/S-PPSQ films exhibited unusual negative
temperature coefficient of resistance (TCR) values, in contrast to
PANI/CSA films that have positive TCR values. Control of their
TCR behavior was demonstrated by obtaining solution blends of
PANI/S-PPSQ and PANI/CSA with negative and positive TCR
values, respectively.
Results and discussion
Linear ladder-type polymeric dopant
In order to develop conducting polymers having high tempera-
ture-stable electrical conductivity, PANI was selected as the
starting material owing to its high electrical conductivity and
good processability,1214 with a linear ladder-type polymeric
dopant. The emeraldine base (EB) form of PANI was synthesized
according to the literature, using the self-stabilized dispersion
polymerization (SSDP) method in a heterogeneous biphasic
solvent consisting of water and chloroform, at a temperature
of 25
C.12,13 The synthesized PANI showed an inherent
viscosity of hinh 3.0 in sulfuric acid and a molecular weight of
Mn 38 600 g mol1, and Mw 181 900 g mol1 in N-methyl-
pyrrolidone solvent in gel permeation chromatography. The

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Fig. 1 (a) Synthetic route of ladder-type sulfonated poly-
phenylsilsesquioxane (S-PPSQ). (b) Schematic illustration of conducting
PANI emeraldine salt (ES) forms doped with polymeric dopant S-PPSQ
(left) and molecular dopant CSA (right).
PANI emeraldine salt (ES) films, prepared from EB-form PANI
doped with the conventional molecular dopant camphorsulfuric
acid (CSA) in m-cresol solvent1013 (molar ratio of aniline unit to
CSA 2 : 1), exhibited a high electrical conductivity of s
411  54 S cm1, as determined by the four-line method.12
For the polymeric dopant, a linear ladder-type S-PPSQ (see
Fig. 1) was used. Polyphenylsilsesquioxane (PPSQ)19,20 was
synthesized by a polycondensation reaction with trimethox-
yphenylsilane (see ESI). The PPSQ polymers, based on strong
SiO bonds, exhibited high thermal stability, with a weight loss
temperature of about 580
C determined by thermogravimetric
analysis (TGA). S-PPSQ was prepared by sulfonation of the
PPSQ polymer with a molecular weight of Mn 4700 g mol1
and Mw 10 000 g mol1. The concentration of the sulfonyl
group was 1.7 mol kg1 of S-PPSQ and the degree of sulfonation
was 72.5  2.5 mol% of the phenyl group. The synthesized
S-PPSQ was dissolved in m-cresol with about 1.0 wt%. The
synthesized PANI (EB) and S-PPSQ polymeric dopant exhibited
high thermal stability; in TGA measurements, no weight loss was
observed up to 400
C (see Fig. S1 in the ESI). The water
content in both PANI (EB) and S-PPSQ is less than 2.5%.
As the doping ratio has a strong influence on both the electrical
conductivity and the physical properties of conducting polymers,
PANI/S-PPSQ films with different doping ratios were prepared
(the molar ratio of aniline unit in PANI to sulfonation group in
S-PPSQ 2 : 1, 2 : 1.5, and 2 : 2). To induce a secondary doping
18152 | J. Mater. Chem., 2012, 22, 1815118155
effect,10,11 m-cresol was used as the solvent, similar to the use of
the conventional molecular dopant CSA. In the four-line method,
PANI/S-PPSQ films with different doping ratios exhibited similar
electrical conductivities in the range s 17  5 S cm1. The
electrical conductivity of PANI/S-PPSQ films is lower than that
of PANI/CSA films. Comparing PANI/S-PPSQ and PANI/CSA
in this work, lower electrical conductivity of PANI films doped
with polymeric dopant compared to PANI films doped with
molecular dopant is often observed.21,22 As shown in Fig. S2 in
the ESI, the X-ray diffraction (XRD) pattern of the PANI/CSA
film exhibits higher crystallinity than the PANI/S-PPSQ film. We
noticed that the lower electrical conductivity of PANI/S-PPSQ
compared to PANI/CSA results from lower pp interchain
stacking of phenyl ring in polyaniline due to low mobility and
high steric hindrance of polymer dopant S-PPSQ.1214
However, the electrical conductivity of PANI/S-PPSQ films
(17  5 S cm1) is significantly higher than the range for previ-
ously reported PANI films doped with polymeric dopants (from
108 to 3 S cm1).21,22 In the UV-Vis-NIR absorption spectra
shown in Fig. 2, the PANI/S-PPSQ film with dark green color
shows typical characteristics of highly conducting materials: a
steadily increasing free-carrier tail in the NIR region and the
absence of an absorption peak at 780 nm corresponding to a
random coil conformation of PANI chains with the isolated
polaron band.10,11,17 We noticed that in the PANI/S-PPSQ films,
the PANI chains possess an extended conformation, as seen in
highly conductive PANI/CSA films. The linear conformation of
the ladder-type S-PPSQ polymeric dopant may help to form this
extended conformation of the PANI chains, resulting in this high
electrical conductivity compared to the previously reported
PANI films doped with polymeric dopants.
Among the PANI/S-PPSQ samples with different doping
ratios, the PANI/S-PPSQ films with the 2 : 1 molar ratio of an
aniline unit in PANI to the sulfonation group in S-PPSQ
exhibited better film quality. Therefore, the physical properties of
these films were investigated in more detail. Hereafter, PANI/
PPSQ and PANI/CSA denote samples with a 2 : 1 molar ratio of
the aniline unit in PANI to the sulfonation group in the dopant.
High temperature stable electrical conductivity
In many studies, thermal stabilities of conducting polymers have
been evaluated using differential scanning calorimetry (DSC) and
Fig. 2 UV-Vis-NIR absorption spectra of PANI EB films from NMP
solution, PANI/CSA and PANI/S-PPSQ films prepared from m-cresol
solution.
This journal is The Royal Society of Chemistry 2012
 thermogravimetric analysis (TGA). These thermal analysis
methods are limited to detecting small changes in the chemical
structure, which could be accompanied by large changes in the
electrical conductivity. Herein, to investigate the stability of
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electrical conductivity, we directly measured the change in
the electrical conductivity after heat treatment. The electrical
conductivity of PANI/S-PPSQ films was measured using the four-
line method at room temperature, after heat treatment at constant
temperatures of 120
C and 150
C, which are similar to or above
temperatures that are typical for fabrication processes and elec-
tronic device operating conditions. For comparison, PANI/CSA
films based on the molecular dopant were also investigated.
Fig. 3 shows the change in the electrical conductivity as a
function of heat treatment time. After heat treatment at both
temperatures, 120
C and 150
C, the electrical conductivity of
conventional PANI/CSA films immediately decreased. In PANI/
CSA films, the relative conductivity s/s0, where s and s0 are
electrical conductivities after and before heat treatment, respec-
tively, was 50% after 1 h at 120
C and 43% after 1 h at 150
C. In
contrast, PANI/S-PPSQ films doped with a ladder-type polymer
dopant exhibited higher stability of the electrical conductivity. As
shown in Fig. 3a, no change in the electrical conductivity of these
films was observed after heat treatment at 120
C after 10 h. Even
after heat treatment at 120
C for 3 days, the PANI/S-PPSQ films
retained their initial level of electrical conductivity (see Fig. S3 in
the ESI). In the heat treatment experiment carried out at 150
C,
shown in Fig. 3b, the electrical conductivity of PANI/S-PPSQ
films decreased only at the beginning of the heat treatment and
even after 35 h, retained a high s/s0 value of 60%, while in the
Fig. 3 Change of relative electrical conductivity as a function of time at
an aging temperature of (a) 120
C and (b) 150
C.
This journal is The Royal Society of Chemistry 2012
PANI/CSA films, the electrical conductivity continuously
decreased and reached a s/s0 value of 10% after 35 h.
To investigate the reason for the enhanced stability of the
electrical conductivity of PANI/S-PPSQ films compared to
PANI/CSA films, the thermal stability of both PANI films was
determined by TGA measurements. In addition, infrared (IR)
absorption, differential scanning calorimetry (DSC) measure-
ments and X-ray diffraction (XRD) pattern measurements of
both PANI films before and after an isothermal heat treatment at
150
C for 10 h were also performed. According to the TGA
measurements recorded with a scan rate of 10
C min1 (see
Fig. S1 in the ESI), both PANI/S-PPSQ and PANI/CSA films
are thermally stable up to 150
C. Fig. 4 shows the time depen-
dence of weight loss with isothermal heat treatment at a
temperature of 150
C. In both types of films, no change in the
weight was observed after 10 h. The initial slight weight loss of a
few percent may correspond to the evaporation of residual
solvent and absorbed humidity.23 In the DSC measurements of
PANI/S-PPSQ and PANI/CSA films before and after heat
treatment at 150
C for 10 h, no significant difference between
DSC curves before and after heat treatments in either of the
PANI films was observed at temperatures below 150
C (see
Fig. S3 in the ESI). On the other hand, at temperatures above
150
C in both PANI films, an endothermic broad peak in the
range of 150230
C, which may be related to solid-to-solid
phase transition with change of pp interchain stacking of
phenyl rings by chemical reactions,24 disappeared after heat
treatment at 150
C. X-ray diffraction (XRD) patterns of PANI
films before and after heat treatment at 150
C for 10 h are shown
in Fig. S2 in the ESI. In both PANI films, the crystallinity
decreases after heat treatment and the variation in the PANI/
CSA film is larger than the PANI/S-PPSQ film. Therefore,
according to the results from TGA and DSC curves and XRD
patterns before and after heat treatment, the change in the
electrical conductivity due to heat treatment in both types of
films may not be the result of a large-scale thermal behavior (i.e.,
thermal decomposition), but may instead result from small
changes in the chemical structure.
In order to investigate changes in the chemical structure due to
the heat treatment, we measured the IR absorption spectra of the
PANI films before and after heat treatment at 150
C for 10 h, as
shown in Fig. 5. In contrast to the PANI/PPSQ samples, PANI/
CSA samples after heat treatment exhibited new absorption
Fig. 4 TGA curves of PANI/CSA and PANI/S-PPSQ films prepared in
m-cresol with isothermal heat treatment at a temperature of 150
C.
J. Mater. Chem., 2012, 22, 1815118155 | 18153
 peaks at 1384 and 1374 cm1, which may correspond to phena-
zine-like structures resulting from thermal-induced side-reactions
of the PANI chains.25 Compared to the molecular dopant CSA,
the ladder-type linear polymeric dopant S-PPSQ may possibly
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reduce the likelihood of conformational change (or mobility) of
PANI chains and inhibit thermal-induced side reactions.
Temperature coefficient of resistance
Each electronic component is required to have optimal temper-
ature-dependent resistance (or electrical conductivity).2629 The
Fig. 5 IR spectra: (a) PANI EB and S-PPSQ, (b) PANI/CSA, and (c)
PANI/PPSQ before and after heat treatment at 150
C for 10 h.
18154 | J. Mater. Chem., 2012, 22, 1815118155
temperature coefficient of resistance (TCR) is the relative change
in resistance as a function of temperature. For organic elec-
trodes, zero or negative TCR behaviors are preferred (i.e.,
constant or decreasing resistance when temperature increases).
For embedded resistors, it is preferable that there should be no
effect of temperature on the electrical conductivity (i.e., zero
TCR). Thermistors require sensitive changes in the resistance
with temperature (i.e., large TCR). Therefore, the control of
TCR behavior of conducting materials is an extremely important
issue in relation to organic electronic devices.
To investigate TCR behavior, the resistance of PANI samples,
prepared by casting on a patterned gold electrode on printed
circuit boards, was measured at various temperatures. The
relative resistance R/R0 values, where R0 and R are the resis-
tances at 25
C and the measurement temperature, respectively,
are shown in Fig. 6. All PANI samples with the initial resistance
R0 in the range of 110 U at 25
C are used. Whereas PANI/CSA
films exhibited positive TCR behavior, PANI/S-PPSQ films
exhibited negative TCR behavior. In general, conducting poly-
mers having high electrical conductivity (>10 S cm1) exhibit
positive TCR behavior above a temperature of 210 K and
negative TCR behavior below 210 K.13,27,28 A temperature above
210 K is the temperature of operation of electronic devices.
Above 210 K, negative TCR behavior has been reported for
conducting polymers only with low electrical conductivity
(<1 S cm1), which is similar in range to the semiconducting
level.29 To the best of our knowledge, the negative TCR behavior
of PANI/S-PPSQ films above room temperature is thus observed
for the first time in organic conducting polymers with such high
electrical conductivity (s > 10 S cm1).
Since PANI/CSA and PANI/S-PPSQ films have been shown to
exhibit positive and negative TCR behaviors above room
temperature respectively, control of TCR behaviors by blending
PANI/CSA and PANI/S-PPSQ solutions in m-cresol was inves-
tigated. The assessed blending ratios of PANI/CSA to PANI/
S-PPSQ were 0.98 : 0.02 and 0.1 : 0.9. Although only a small
amount of one of the solutions having opposite TCR behavior
was added in each case, the TCR values of the resulting blends
changed dramatically, as shown in Fig. 6. Compared to non-
blended PANI/CSA films with an R/R0 of 1.74 at 150
C, the
blend with 0.98 : 0.02 ratio showed a lower TCR value with an
Fig. 6 Temperature coefficient of resistance of PANI/CSA film, PANI-
S-PPSQ film, and their blended samples.
This journal is The Royal Society of Chemistry 2012
 R/R0 of 1.33. Moreover, the blend with 0.1 : 0.9 ratio showed a
TCR value with an R/R0 of 0.57 at 150
C, which was higher than
that of the non-blended PANI/S-PPSQ films that had an R/R0 of
0.15. Therefore, it is clear that by changing the blending ratio, the
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TCR behavior of the blended samples can be finely controlled.
Conclusion
We reported on conducting polyaniline (PANI) films doped with
thermally stable polymer dopant, linear ladder-type sulfonated
polyphenylsilsesquioxane (S-PPSQ). The PANI/S-PPSQ films
exhibited high-temperature stable electrical conductivity. With
heat treatment at 120
C, the electrical conductivity of conven-
tional PANI films doped with the molecular dopant camphor
sulfuric acid (CSA) rapidly decreased to half of the initial values,
while that of PANI/S-PPSQ films were relatively unaffected.
Moreover, PANI/S-PPSQ films exhibited unusual negative
temperature coefficient of resistance (TCR) values, in contrast to
PANI/CSA films that have positive values. It was also shown
that by using a solution blend of PANI/S-PPSQ and PANI/CSA
with negative and positive TCR values, respectively, we
successfully demonstrated the control of TCR behavior. There-
fore, PANI/S-PPSQ materials are very promising for organic
electronic applications.
Acknowledgements
This work has been supported by a grant from the Fundamental
R&D Program for Core Technology of Materials funded by the
Ministry of Commerce, Industry and Energy, Republic of Korea,
the Priority Research Centers Program (2011-0017494) through
the NRF of Korea funded by the Ministry of Education, Science
and Technology, and the Ajou university research fund (S-2011-
G0001-00083).
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