Polymer-Plastics Technology and Engineering

ISSN: 0360-2559 (Print) 1525-6111 (Online) Journal homepage: http://www.tandfonline.com/loi/lpte20

Poly(3,4ethylenedioxythiophene):Poly(styrenesulfonic
Acid) (PEDOT:PSS) Conductivity Enhancement
through Addition of Imidazolium-Ionic Liquid
Derivatives
Fariborz Atabaki, Mohamad Hasan Yousefi, Amir Abdolmaleki & Mohsen
Kalvandi
To cite this article: Fariborz Atabaki, Mohamad Hasan Yousefi, Amir Abdolmaleki & Mohsen
Kalvandi (2015) Poly(3,4-ethylenedioxythiophene):Poly(styrenesulfonic Acid) (PEDOT:PSS)
Conductivity Enhancement through Addition of Imidazolium-Ionic Liquid Derivatives, PolymerPlastics Technology and Engineering, 54:10, 1009-1016, DOI: 10.1080/03602559.2014.979500
To link to this article: http://dx.doi.org/10.1080/03602559.2014.979500

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Date: 17 January 2017, At: 07:20

Polymer-Plastics Technology and Engineering, 54: 10091016, 2015

Copyright # Taylor & Francis Group, LLC
ISSN: 0360-2559 print/1525-6111 online
DOI: 10.1080/03602559.2014.979500

Poly(3,4-ethylenedioxythiophene):Poly(styrenesulfonic
Acid) (PEDOT:PSS) Conductivity Enhancement through
Addition of Imidazolium-Ionic Liquid Derivatives
Fariborz Atabaki1, Mohamad Hasan Yousefi2, Amir Abdolmaleki3, and
Mohsen Kalvandi1
1

Department of Chemistry, Malek Ashtar University of Technology, Isfahan, Islamic Republic of Iran
Department of Physics, Malek Ashtar University of Technology, Isfahan, Islamic Republic of Iran
3
Department of Chemistry, Isfahan University of Technology, Isfahan, Islamic Republic of Iran
2

GRAPHICAL ABSTRACT

Here, insignificant conductivity enhancement of PEDOT:PSS through adding different

amounts of 2-methylimidazolium ionic liquids into PEDOT:PSS aqueous solutions is
reported. Maximum conductivity was reached through 2-methylimidazolium hydrogen
sulfate (5 wt.%) addition. It seems that observed conductivity enhancement mainly results
from the impact of ionic liquids on the electrical properties and conformational change of
PEDOT chains, and through weakening of the electrostatic interactions between PEDOT
and PSS. Also, better conductivity was achieved through weak interactions between
PEDOT and the PSS chain, which changes the PEDOT conformation and further
delocalizes the polarons, as well as changes the electron transport properties.
Keywords

Conductivity enhancement; Electrical properties; Ionic liquids; Optical properties;

PEDOT:PSS

INTRODUCTION
During the second half of the 1980s, scientists at the Bayer
AG research laboratories developed a new polythiophene
derivative, poly(3,4-ethylenedioxythiophene) (PEDOT) derived
from ethylenedioxythiophene (EDOT). Initially, synthesized
polymer (as a water-insoluble polymer) shows a very stable
conductivity opposite to many other conjugated highly conductive polymers. The advantages of this polymer are optical
Address correspondence to Fariborz Atabaki, Department of
Chemistry, Malek Ashtar University of Technology, 1957975783
Isfahan, Islamic Republic of Iran. E-mail: atabaki@mut-es.ac.ir
Color versions of one or more of the figures in this article can be
found online at www.tandfonline.com/lpte.

transparency in its conducting state, high stability and moderate

band gap and low redox potential. However, its huge disadvantage is poor solubility. This polymer in combination with poly
(styrene sulfonic acid) can be used as a water-soluble polyelectrolyte complex (PEC) called poly(3,4-ethylenedioxythiophene):poly(styrenesulfonic acid)[15].
Poly(styrenesulfonic acid) (PSS) has two main functions.
First, it is a resource for charge balancing; second, hydrophilic
PSS keeps hydrophobic PEDOT segments dispersed in a water
solution. The PEDOT chains attached to the PSS chains through
Coulombic interaction and were stabilized by excess PSS.
Figure 1 shows the schematic core and shell structure of
a PEDOT: PSS film which is made of grains which diameters

1009

1010

F. ATABAKI ET AL.

FIG. 1. The morphology of PEDOT: PSS and its chemistry structure.

are about 50 nm. The conductive PEDOT is rich in the core,

while the insulating PSS is rich in the shell of a grain. The
shell is almost 510 nm thick.
This insulator shell hindered the charge transmit across the
grains, and it is known as one of the factors that may lead to
low conductivity (<1 S cm
1), which is seen on PEDOT:PSS
film. Moreover, the PEDOT and PSS chains are connected by
Coulombic interaction, and there is a stress in the polymer
chains due to the discord between the PEDOT and PSS chains,
so the PEDOT chains acquire a coiled structure. Accordingly, it
ends up as the localization of the positive charges. This is one
more reason to account for the low conductivity of PEDOT:
PSS. Therefore, approaches that lower the amount of PSS
in the PEDOT:PSS film and/or reduce the stress in PEDOT:
PSS can improve the conductivity of PEDOT:PSS[6,7].
Using some additives to overcome these disadvantages has
been the most important goal for lots of researchers group.
It is highly possible to significantly enhance the conductivity
of PEDOT:PSS by adding certain chemicals. Table 1 shows
a range of chemicals and their effects on the conductivity of
PEDOT:PSS films. These include many organic solvents,
sugars, polyols and different salts[822].
Not long ago, treatment of PEDOT:PSS films with amphiphilic fluoro compounds or geminal diols showed significant
enhancement in polymer conductivity, which can be compared
to that of ITO[9,10]. There was substantial effort in developing
the conductivity of PEDOT:PSS, and several approaches have
been described to particularly develop the conductivity of
PEDOT:PSS. Early efforts concentrated on the change of the
solvent for PEDOT:PSS. Pettersson et al. monitored conductivity enhancement while adding solid sorbitol into the
PEDOT:PSS aqueous solution, but just after that, the film was
baked at a high temperature.[32] They claimed that the additive
probably acted as a plasticizer to help reorient the PEDOT chains
at high temperature[8,13,18]. Kim et al.[11] observed the conductivity enhancement by adding dimethylsulfoxide (DMSO),
N,N-dimethylformamide (DMF), or tetrahydrofuran (THF).

They suggested that the remaining solvent brings about

a screening impact between the positively charged PEDOT
chains and negatively charged PSS chains, and therefore
decreasing the Coulombic interaction between them[11].
Jonsson et al.[23] studied the impact of sorbitol and 1-methyl2-pyrrolidinone (NMP). They proposed that the conductivity
is increased because the insulating PSS chains are washed away
from the surface region of the PEDOT:PSS film during film
formation, while they leave a high-conductivity thin layer with
a high amount of PEDOT chains on the surface[8,15]. Crispin
et al. realized that the conductivity enhancement is not equivalent to additive concentration and molecular weight[13,14,20,21].
According to the polar solvent, decreasing the Coulombic
interaction between PEDOT and PSS
chains, the screening
influence is so crucial for the conductivity enhancement.
Although, the PEDOT:PSS solution usually is more stable before
adding organic solvents. Thus, researchers have focused on
the methods to treat PEDOT:PSS films with these polar organic
compounds. These methods are immersing PEDOT:PSS film
in polar solvents or spin-coating polar solvents on the pristine
PEDOT:PSS film. The conductivity enhancement is due to
increased interchain interaction and the conformational change
of the PEDOT chains. Besides the polar organic compounds,
the introduction of ionic liquids[2326] or anionic surfactants into
the PEDOT:PSS aqueous solution or treating the PEDOT:PSS
with dichloroacetic acid (DCA)[27] can particularly enhance
the conductivity of PEDOT:PSS. So, there is still room for
further development of the conductivity of the PEDOT:PSS
film[6].
In this study, acidic ionic liquids were used as a secondary
dopant to enhance the conductivity by reducing the Coulombic
interaction and impact between the positively charged PEDOT
chains and negatively charged PSS chains.
EXPERIMENTAL PROCEDURE
Materials and Reagents
The liquid solutions of PEDOT:PSS applied have different
concentrations, adherence and conductivity. Two external
and an internal synthesized sample selected as well as their
characteristics are described here.
Polymer 1: PEDOT:PSS aqueous solution (cleviosTM PH
1000) was purchased from Hraeuse. The concentration
of PEDOT:PSS was 1.3 wt.% and the weight ratio of
PSS to PEDOT was 2.5.
Polymer 2: PEDOT:PSS aqueous solution (Ossila 4083)
was purchased from H.C. Starck. The concentration of
PEDOT:PSS was 1.5 wt.% and the weight ratio of PSS
to PEDOT was 6.
Polymer 3: PEDOT:PSS aqueous solution was synthesized
in our research laboratory at Malek-e-Ashtar University
of Technology in Isfahan. The concentration of PEDOT:
PSS was 1.6 wt.% and the weight ratio of PSS to
PEDOT was 6[29].

1011

(PEDOT:PSS) CONDUCTIVITY ENHANCEMENT

TABLE 1
Additives and their effect on the conductivity of PEDOT:PSS
Conductivity Enhancement Factor
(Maximum of different values)

Substance
Monovalent alcohols

None

Polyols

500
45
100
1000

Alcohols with a second

polar group

100

Hydroxylated ethers
Ethers
Amines
Amides

Sulfoxides
Ketones
Nitriles
Nitromethane
Salts

50
5
17
5
None
40
100
100
800
None
None
None
700

Conductivity Enhancement Agent

Acidic ionic liquids, that are used as secondary dopant
for PEDOT:PSS are synthesized in our laboratory based on
previously reported procedure[4,2830]. This acidic ionic liquids

Example

References

Methanol
Ethanol
Heptanol
Ethylene glycol
Sorbitol
Meso-Erythritol
Geminal diols or amphiphilic
fluoro compound
2-Nitroethanol
Methoxyphenol
Diethylene glycol
Polyethylene glycol
Tetrahydrofurane
Pyridine
N,N-Dimethylformamide
N,N-Dimethylacetamide
N-Methylpyrolidone
Dimethylsulfoxide
Cyclohexanone
Acetonitrile
Nitromethane
Copper(II) chloride

[8]

[8,19]
[13,18]
[8]
[9,10]
[8]
[8]
[13,20]
[14]
1[1]
[8]
[11]
[8]
[8,15]
[8,11,16,17, 22]
[8]
[8,12]
[8,12]
[21]

that are used as conductivity enhancement agent of the polymer

PEDOT:PSS is including ionic liquids: 2-methylimidazolium
chloride, 2-methylimidazolium bromide, 2-methylimidazolium
hydrogen sulfate that each were prepared with the same molar

TABLE 2
Resistance of PEDOT:PSS films before and after treatments with ionic liquids
Sample
A
B
C
D
E
F
G
H
I
J
K
L
M
N

Specifications of PEDOT:PSS

Polymer to water ratio

Resistance

Polymer 1 (Heraeus clevios PH 1000)

A sample doped with 5 wt.% of 2-methylimidazolium chloride
A sample doped with 5 wt.% of 2-methylimidazolium bromide
A sample doped with 5 wt.% of 2-methylimidazolium hydrogen sulfate
Polymer 2 (Ossila 4083)
E sample doped with 5 wt.% of 2-methylimidazolium chloride
E sample doped with 5 wt.% of 2-methylimidazolium bromide
E sample doped with 5 wt.% of 2-methylimidazolium hydrogen sulfate
Polymer 3 (synthesized in our research laboratory)
I sample doped with 5 wt.% of 2-methylimidazolium chloride
I sample doped with 5 wt.% of 2-methylimidazolium bromide
I sample doped with 5 wt.% of 2-methylimidazolium hydrogen sulfate
E sample doped with 30 wt.% of 2-methylimidazolium hydrogen sulfate
A sample doped with 30 wt.% of 2-methylimidazolium chloride

1:25
1:25
1:25
1:25
1:25
1:25
1:25
1:25
5:25
5:25
5:25
5:25
1:25
1:25

26 KX
39 X
28 X
450 X
over of 20 MX
12 KX
4.52KX
10 KX
over of 20 MX
82 KX
366 KX
7.5 X
21 X
52 X

1012

F. ATABAKI ET AL.

SCH. 1. Reaction for 2-methylimidazolde with H2SO4.

FIG. 2. Copper board designed to measure the resistance of the polymer

layer.

ratio of 2-methylimidazol to HCl, HBr and H2SO4[30]. Other

chemicals used in this study obtained from Fluka Chemical
Co. (Switzerland) and Merck Chemical Co. (Germany).
PEDOT:PSS aqueous solutions were prepared based on
Table 2. For the control experiment, samples; A, E and I were
performed with no-ionic liquids. Samples; B, C, D, F, G, H, J,
K, L, M and N with different amounts of ionic liquids as doped
samples were irradiated at ultrasonic bath for 30 min.

FIG. 4. UV absorption spectra of PEDOT:PSS films before and after

treatments with ionic liquids.

RESULTS AND DISCUSSION

Increase the Conductivity of Aqueous Solution PEDOT:
PSS by Ionic Liquids
The conductivity of PEDOT:PSS was increased significantly
by treating with polar additives like, EG and other polyols, yet
when using the single-agent alcohol, the conductivity change
is little. It seems that the high polarity of acidic ionic liquids
and the ability to form hydrogen bonds have good performance

in increasing the conductivity. It seems, that the ionic liquids

with high dielectric constants that have ability to form hydrogen
bonding can be considered as a special secondary dopant to
significantly increase the conductivity of PEDOT:PSS. We
suggest that the ionic liquid that has OH groups linked to an atom
can be considered as a special polyol and can significantly
increase the conductivity of 2-methylimidazol with H2SO4
converted to 2-methylimidazolium hydrogen sulfate (Scheme 1).
A new method designed by Yousefi et al. at Malek-e-Ashtar
University of Technology[31] was used to measure the

FIG. 3. UV absorption spectra of ionic liquids. 2-methylimidazolium chloride (1), 2-methylimidazolium bromide (2) and 2-methylimidazolium hydrogen
sulfate (3).

FIG. 5. Transmittance spectra of PEDOT:PSS before and after treatments

with ionic liquids (185300 nm).

(PEDOT:PSS) CONDUCTIVITY ENHANCEMENT

FIG. 6. Transmittance spectra of PEDOT:PSS before and after treatments

with ionic liquids (300700 nm).

resistance of samples by the drop coating method. This new

method has some advantage such as measuring uniform resistance without polymer layer damaging (Fig. 2).
Same condition and standard used to collect the samples
conductivity based on mentioned method (Table 2).
Optical and Electrical Properties of PEDOT:PSS before
and after the Ionic Liquids Treatment
Mechanism of conductivity increasing through ionic liquids
addition has been studied based on different techniques. UV
absorption spectra of ionic liquids and aqueous solutions
of different samples of PEDOT:PSS doped and nondoped

1013

are shown in Fig. 3 and Fig. 4. Significant band shifting and

changing in bands intensity observed after increasing of acidic
ionic liquids.
Absorption peak shift indicates that by increasing the ionic
liquids the absorption of the UV zone was shifted to the visible
zone and higher nanometer, which confirms better resonance
and higher conductivity. Appearance of a new peak
at 260 nm in internal samples confirms better efficiency of
secondary dopant to increase conductivity. So, shifting from
the UV area toward visible region and higher nanometer is
good news in order to achieve greater efficiency and absorption especially for solar cells and OLED applications. On the
other hand, peak shift from UV toward the visible region
and higher nanometer values make them a good candidate
for use in solar cells and OLED.
The intensity of the absorption band has changed after
secondary doping with acidic ionic liquids, which showed
significant improvement in the conductivity of PEDOT:PSS.
The transmittance spectra confirm absorption by UV-Vis
system (Fig. 5). In all parts with minimum absorption, the
transmittance is nearly 100%.
Although ionic liquids significantly increase the conductivity
of PEDOT:PSS solutions, it does not affect polymers transparency in visible region. Figure 6 presents the transmittance
spectra of PEDOT:PSS with different 2-methylimidazolium
salts.
Photoluminescence spectroscopy for emission and sending
wavelengths is used by LS55 system (Fig. 7). Two PL peaks
with wavelengths between 300 and 450 nm are the 2p bands
of the sulfur atoms in PSS, whereas the two PL peaks (between
550 and 800 nm) are the 2p bands of the sulfur atoms in

SCH. 2. Transformation of the PEDOT chain from the benzoid to the quinoid structure. The dot and plus represents the unpaired electron and positive charge on the PEDOT chain, respectively.

FIG. 7. S 2p PL spectra of untreated and ionic liquids-treated PEDOT:PSS.

SCH. 3. Schematic structures of PEDOT:PSS before and after 2-methylimidazolium hydrogen sulfate treatment.

1014

F. ATABAKI ET AL.

PEDOT. The S2p PL intensity ratio of PEDOT to PSS increases

after ionic liquid treatment. This approach probability shows
more efficient conjugation, which means better resonance and
higher conductivity.
These results suggest that the mechanism for the conductivity enhancement of PEDOT:PSS by ionic liquids can give
rise to the phase segregation of PSSH chains from PEDOT:
PSS and the conformational change of the PEDOT chains.
Acidic ionic liquids also can change the composition and
structure of PEDOT:PSS. The ionic liquid-induced phase
segregation of the PSS chains can be ascribed to the shielding
of the Coulombic attraction between PEDOT and PSS.
Some of these PSS chains can be removed from the polymer
solutions by rinsing with water. Washing away some PSS
chains from the PEDOT:PSS surface can reduce the less
conductive shell leading to the conductivity enhancement.

The benzoid structure of PEDOT (Scheme 2) may be the

preferred structure for a coil conformation, while the quinoid
structure may be the preferred structure for a linear or
expanded-coil structure. Therefore, it seems that both coil
and linear or expanded-coil conformations exist in a PEDOT:
PSS film, but after adding ionic liquids (which decrease
Coulombic interaction) the coil conformation turns into
a linear or expanded-coil conformation, which enhanced
the conductivity. This conformational change increases the
free volume and increases the chain interaction to help the
conductivity based on a hopping mechanism.
The results indicate that acidic ionic liquids can lead
to conformational changes in the PEDOT chains in the
PEDOT:PSS film. The 2-methylimidazolium hydrogen sulfate
(C4H8N2O4S) has favorable interactions with both PEDOT
and PSS chains (Scheme 3). Because of these interactions,

FIG. 8. AFM images of PEDOT:PSS films (a) untreated and treated with (b) 2-methylimidazolium chloride, and (c) 2-methylimidazolium hydrogen sulfate.
The unit for the AFM images is mm.

(PEDOT:PSS) CONDUCTIVITY ENHANCEMENT

PEDOT chains separated from PSS chains using C4H8N2O4S.

This led to a reduction in Coulombic between the PEDOT and
PSS. Thus, phase separation occurs between the hydrophobic
PEDOT and hydrophilic PSS chains.
The polar structure of acidic ionic liquid can be one reason
for higher conductivity. Acidic ionic liquids have the potential
to stay between PEDOT and PSS, increasing the space
between two species, and prevent twisting of the chain around
itself. In addition it helps the electron transportation in a direct
way, due to ionic liquid action, so electron transportation from
one chain to another chain is easily done. Therefore the action
of hopping will be improved. Therefore ionic liquids transform
the wrapped chains to linear mode, to create a lower pathway
for electron transfer, and also pull over the core/shell structure
to increase conductivity through the hopping process.
AFM
AFM studies show a significant change in surface
morphology PEDOT:PSS film (Fig. 8). Conductivity increases
are associated with a screening effect between the positively
charged PEDOT chains and negatively charged PSS chains,
thus reducing the Coulombic interaction between them. Ionic
liquids also washed away the insulating PSS chain from the
surface. The film doped with 2-methylimidazolium hydrogen
sulfate gives a tangible and flatter film, which shows better
PSS washing from the PEDOT:PSS surfaces.
CONCLUSIONS
In this work, we demonstrate an efficient method to modify
and increase conductivity of PEDOT:PSS by adding ionic
liquids as secondary dopant. As a result, treatment of PEDOT:
PSS film with ionic liquids significantly enhance the conductivity. Addition of ionic liquids induced screening effect
between the positively charged PEDOT chain and negatively
charged PSS chains thus reduce the Coulombic interaction
between them. Ionic liquids also enhanced conductivity because
the insulating PSS chain are washed away from the surface and
leave a higher conductive layer with a high amount of PEDOT
chain on surface. The treatment was not effective on PEDOT:
PSS films in the visible spectrum and created a PEDOT:PSS solution that has high transparency and low resistance.
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