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Polymerizable Supramolecular Approach to Highly Conductive PEDOT:PSS Patterns Taegeun Kim, Suryong Ha, Hyosung Choi, Kyungchan Uh, Umesha Kundapur, Sumin Park, Chan Woo Lee, Sang-hwa Lee, Jaeyong Kim, and Jong-Man Kim ACS Appl. Mater. Interfaces, Just Accepted Manuscript • Publication Date (Web): 19 May 2017 Downloaded from http://pubs.acs.org on May 21, 2017

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ACS Applied Materials & Interfaces

Polymerizable

Supramolecular

Approach

to

Highly Conductive PEDOT:PSS Patterns Tae Geun Kim,† Su Ryong Ha,‡ Hyosung Choi,*,‡ Kyungchan Uh,† Umesha Kundapur,§ Sumin Park,† Chan Woo Lee,*,§ Sang-hwa Lee,∥ Jaeyong Kim,∥,§ and Jong-Man Kim*,†, § †

Department of Chemical Engineering, Hanyang University, Seoul 04763, Korea

‡

Department of Chemistry and Research Institute for Convergence of Basic Sciences, Hanyang University, Seoul 04763, Korea § ∥

Institute of Nano Science and Technology, Hanyang University, Seoul 04763, Korea Department of Physics, Hanyang University, Seoul 04763, Korea

ABSTRACT Owing to its high conductivity, solution processability, mechanical flexibility and transparency, poly(3,4-ethylenedioxythiophene):poly(styrenesulfonate) (PEDOT:PSS) has been extensively explored for use in functional devices including solar cells, sensors, light emitting diodes and supercapacitors. The ability to fabricate patterned PEDOT:PSS on a solid substrate is of significant importance in order to develop practical applications of this conducting polymer. Herein we describe a new approach to obtain PEDOT:PSS patterns that is based on a polymerizable supramolecular concept. Specifically, we found that UV irradiation of a photopolymerizable diacetylene containing PEDOT:PSS film followed by development in deionized water and subsequent treatment with sulfuric acid (glass and silicon wafer) or formic acid (PET) produces micron-sized PEDOT:PSS patterns on solid substrates. The newly designed photolithographic method, which can be employed to generate highly conductive (>1000 S/cm) PEDOT:PSS patterns, has many advantages including the use of aqueous process conditions, a reduced number of process steps and no requirement for plasma etching procedures. KEYWORDS: PEDOT:PSS, polydiacetylene, conducting polymer, pattern, photolithography A ACS Paragon Plus Environment


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INTRODUCTION Conducting polymers have been extensively employed as key materials in a variety of functional devices including sensors, organic light emitting diodes, solar cells, and actuators. Among

the

numerous

conducting

polymers

explored,

poly(3,4-

ethylenedioxythiophene):poly(styrenesulfonate) (PEDOT:PSS) has received special attention owing to its solution processability, mechanical flexibility and transparency.1-7 In addition, this polymer displays high conductivity (>4000 S/cm) following treatment with concentrated sulfuric acid.8

The combination of these optical, electrical and mechanical properties makes

PEDOT:PSS a unique and attractive substance for organic based functional devices. For practical application, it must be possible to fabricate readily patterned images of PEDOT:PSS on solid substrates. For this purpose, several techniques have been developed including inkjet printing,9-10 pulsed UV lasing,11 mold transfer,12 photolithographic methods,13-14 dilution filtration,15-17 transfer printing/lamination.18-19 Among these approaches, photolithography is the most popular and practical method for generating of PEDOT:PSS patterns. In the typical photolithographic process, a photoresist material is coated over a PEDOT:PSS film. Photomasked UV irradiation followed by removal of the unprotected PEDOT:PSS layer by using an etching process (typically by oxygen-plasma etching) then yields a patterned photoresist. Finally, removal of the residual photoresist layer affords PEDOT:PSS patterns. Although this approach enables generation of PEDOT:PSS patterns with sub-micron sized resolution, it requires an orthogonal photoresist material, development in a special organic solvent (e.g. hydrofluoroether) and a plasma etching step. More recently, a protocol for photolithographic patterning of PEDOT:PSS that utilizes silk protein as a resist material was devised.20 The silk-matrix-based approach enables the generation of conducting polymer macro patterns using an aqueous process. The fact that the resist material is derived

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from a silk protein makes it difficult to utilize this process in a general manner in typical laboratories. To overcome limitations associated with the photolithographic methods described to date, we have designed a new approach that is based on a polymerizable supramolecular concept. The new method, which produces highly conductive (>1000 S/cm) PEDOT:PSS patterns, involves a reduced number of process steps, does not require a plasma etching procedures and is all aqueous processable.

EXPERIMENTAL SECTION Materials. The PEDOT:PSS aqueous solution (Clevios PH1000) was purchased from Heraeus Clevios with a solid concentration 1.0–1.3 wt% and used as received. 10,12Pentacosdiynoic acid (PCDA) was purchased from GFS chemicals. 2-Aminoethylsulfate was purchased from Sigma-Aldrich (Korea).

Instruments. Optical microscopic images were collected with an Olympus BX 51W/DP70. Raman spectra were obtained using the wide illumination (WAI) scheme (PhAT system, Kaiser Optical Inc., Ann Arbor, MI, USA). XRD data were collected using a D8 Discover (Bruker,

Germany).

Spectrophotometer

UV/VIS/NIR

(Lambda

1050,

spectra

were

PerkinElmer).

obtained The

using

a

UV/Vis/NIR

direct-current

conductivity

measurements of the films were performed using the four-line-probe method with a Keithley 237 Source-Measure Unit.

Synthesis of Sodium 2-pentacosa-10,12-diynamidoethyl sulfate (PCDSA). To a mixture of 10,12-pentacosadiynoic acid (1.0 g, 2.67 mmol) and 2-aminoethyl hydrogen sulfate (0.31 g, 2.22 mmol) in anhydrous N,N-dimethylformamide (20 mL) was added triethylamine (0.67 g, C ACS Paragon Plus Environment


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6.66 mmol) under a nitrogen atmosphere. 1-Propanephosphonic anhydride solution 50% w/w in EtOAc (2.12 mL, 3.33 mmol) was then added dropwise at 0 °C. The resulting homogeneous solution was stirred at room temperature for 18 h. After concentration in vacuo, the residue was diluted with water (50 mL), acidified by adding 3N hydrochloric acid and washed with dichloromethane (3 x 50 mL). The aqueous layer was separated and basified with 10% sodium bicarbonate. The precipitate formed by standing in a freezer overnight was collected by filtration, washed with water and dried under suction. The crude material was triturated with acetonitrile (20 mL), filtered and dried in vacuo to afford the title compound (0.9 g, 79%) as white solid. IR: (cm-1) vmax 723, 781, 955, 1024, 1079, 1221, 1460, 1557, 1641, 2918, 2952, 3295. 1H NMR: (300 MHz, DMSO-d6): δ 7.85 (t, 1H) 3.69 (t, J=5.7 Hz, 2H), 3.19 (q, J=5.7 Hz, 2H), 2.26 (t, J=6.9 Hz, 4H), 2.04 (t, J=7.2 Hz, 2H), 1.46-1.23 (m, 32H), 0.85 (t, J=5.7 Hz, 3H). 13C NMR: (75 MHz, DMSO-d6): δ 172.14, 77.96, 65.35, 65.31, 64.38, 35.30, 31.30, 29.00, 28.94, 28.86, 28.70, 28.38, 28.23, 28.16, 27.74, 27.68, 25.20, 22.10, 18.27, 13.96.

Fabrication of PEDOT:PSS Patterns. A PEDOT:PSS solution containing 5 wt% PCDSA was spin-coated on a glass substrate to make a thin polymer film (thickness: ca. 100 nm). Photomasked UV irradiation (254 nm, 28.3 mW/cm2, 10 min) was followed by incubation of the glass substrate in deionized water for 1 min at ambient temperature. The water treated glass substrate was then exposed to a concentrated H2SO4 solution (18 M) for 10 min, washed with water and dried to give conductive PEDOT:PSS patterns. A similar procedure was used for patterning on a silicon wafer. Since the PET substrate is labile to strong sulfuric acid, aqueous formic acid solution (99.0 %) was used in the final step of the process to afford a PEDOT:PSS patterned flexible PET film.

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Device fabrication and characterization. The ITO-coated and PCDSA-PEDOT:PSS film-coated glass substrates were used for fabrication of control and ITO-free devices, respectively. For control device, after UV-ozone treatment for 10 min, a solution of poly(3,4ethylenedioxythiophene):polystyrene sulfonate (PEDOT:PSS, Clevios VP Al 4083) was spincoated onto ITO substrate at 4000 rpm for 40 s and then baked at 140 oC for 10 min. For ITO-free device, PEDOT:PSS layer was deposited on PCDSA-PEDOT:PSS electrode using same spin-coating condition without UV-ozone treatment. The same procedures was used to deposite the active layer and aluminum (Al) cathode for both devices. The substrates were transferred into a glove box and the active layer was spin-coated on the PEDOT:PSS layer from the solution of PTB7-Th:PC71BM = 1:1.5 (w/w) dissolved in mixed solvent of chlorobenzene (CB) and diphenylether (DPE) (CB:DPE=97:3 vol.%). Subsequently, an Al electrode (thickness of 100 nm) was deposited on top of the active layer under vacuum (1500 S/cm) and formic acid was also found to efficiently induce conductivity (992 S/cm). The other reagent resulted in formation of the following order of conductivity: nitric acid (612 S/cm), methane sulfonic acid (424 S/cm), ethylene glycol (372 S/cm) and phosphoric acid (200 S/cm).

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Figure 2. UV-vis absorption spectra (a), near IR spectra (b) Raman spectra (c) and wide angle XRD patterns (d) of PEDOT:PSS films on glass substrates derived from 5 wt% PCDSA-PEDOT:PSS before UV irradiation (black line), after 254 nm UV irradiation (28.3 mW/cm2) for 10 min (red line) and after treatment with 18M aqueous H2SO4 (blue line). (e) Conductivity of patterned PEDOT:PSS films as a function of weight ratio of the embedded diacetylene PCDSA. (f) Solvent dependent conductivity of patterned PEDOT:PSS films (5 wt% PCDSA).

The next phase of the investigation focused on the creation of patterned PEDOT:PSS images on a flexible and transparent substrate. One advantage of using polymeric rather than conventional inorganic conducting materials is their relative ease with which flexible conducting patterns are created.

In order to test the feasibility of producing flexible and

transparent conducting patterns, 5 wt% PCDSA-PEDOT:PSS was spin-coated on an oxygen

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plasma treated transparent PET film (thickness: ca. 100 nm). Sequential photomasked UV irradiation (254 nm, 28.3 mW/cm2, 10 min), water development (deionized water, 1 min), and formic acid treatment (99%, 10 min) of the composite film afforded patterned flexible PEDOT:PSS images (Figure 3a). Because the PET substrate is reactive with concentrated sulfuric acid, formic acid, which does not damage the polymer substrate, was used as the final dopant solvent. The patterned conducting PET film produced in this manner had a conductivity of >900 S/cm. The highly conductive nature of the PEDOT:PSS patterns on the PET film was demonstrated by employing them in a circuit used to turn on a LED light (Figure 3b, see also supporting Movie S1).

Figure 3. (a) A flexible PEDOT:PSS patterned PET film. The conducting polymer pattern was fabricated using 5 wt% PCDSA-PEDOT:PSS by sequential UV irradiation (28.3 mW/cm2, 10 min), development in deionized water followed by treatment with formic acid. Formic acid was employed since concentrated sulfuric acid resulted in the damage of the PET film. (b) Turning on of a LED using a PEDOT patterned PET film (working voltage: 3V, frequency: 1.0 Hz).

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To confirm the usefulness of the PCDSA-PEDOT:PSS transparent conducting polymer, it was utilized in place of an ITO anode to fabricate a polymer solar cell. The simple device had the following configuration: (PCDSA-PEDOT:PSS) anode / PEDOT:PSS / active layer / Al cathode. The PEDOT:PSS between anode and the active layer is used as hole transport layer for efficient hole transport/collection efficiency (Figure S3 and Table S1). The active layer consisted of poly[4,8-bis(5-(2-ethylhexyl)thiophen-2-yl)benzo[1,2-b;4,5-b']dithiophene-2,6diyl-alt-(4-(2-ethylhexyl)-3-fluorothieno[3,4-b]thiophene-)-2-carboxylate-2-6-diyl)] (PTB7Th) and [6,6]-phenyl-C71-butyric acid methyl ester

(PC71BM), where PTB7-Th is one of the

highest performing photovoltaic polymers used for polymer solar cells. For comparison purposes, we also prepared a control device using an ITO substrate. In Figure 4a and 4b are shown the current density-voltage (J-V) characteristics and external quantum efficiency (EQE) curves of the ITO and PCDSA-PEDOT:PSS anode based devices. The control device with an ITO anode had a power conversion efficiency (PCE) of 7.04% with short-circuit current density (JSC) of 14.09 mA cm-2, open-circuit voltage (VOC) of 0.80 V, and fill factor (FF) of 0.62. Importantly, the PCDSA-PEDOT:PSS based device exhibits a performance that is comparable to that of the ITO based device. Specifically, the device constructed using a PCDSA-PEDOT:PSS anode had a JSC of 15.23 mA cm-2, VOC of 0.76 V, and FF of 0.58, giving rise to a PCE of 6.70%. The slightly lower PCE of the device with PCDSAPEDOT:PSS resulted from the lower conductivity of PCDSA-PEDOT:PSS compared to that of ITO (~10,000 S/cm).41-42 We compared our result with previous works on organic and perovskite solar cells based on PEDPT:PSS electrode (Table S2). The difference between the EQE curves for two devices is attributed to a difference between the transmittances of ITO and PCDSA-PEDOT:PSS electrode in the UV to near IR wavelength region (Figure S4). Calculated JSC values from EQE curves of both devices were in a good agreement with those derived from J-V measurements. N ACS Paragon Plus Environment

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Figure 4. J-V characteristics (a) and EQE curves (b) of polymer solar cells based on an ITO and a PCDSA-PEDOT:PSS anode.

CONCLUSIONS In summary, the above study resulted in the development of a straightforward method for fabricating PEDOT:PSS patterns on solid substrates. By employing a photopolymerizable O ACS Paragon Plus Environment


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hydrophilic diacetylene as a dissolution inhibitor, we were able to create micronsized conducting polymer patterns on glass, a silicon wafer and a flexible PET film. We also demonstrated that the PEDOT:PSS film serves as alternative to ITO as a transparent electrode for polymer solar cells. In contrast to the difficult and/or tedious procedures needed in current patterning technologies, the polymerizable supramolecular approach described above is simple and efficient. Consequently, the process we have developed should open new avenues for the fabrication of PEDOT:PSS patterns.

SUPPORTING INFORMATION The Supporting Information is available free of charge on the ACS Publications website at DOI: . Contact angles, proton NMR of PCDSA and Transmittance spectra, supporting Movie. AUTHOR INFORMATION Corresponding Author *E-mail: [email protected] (J.-M. Kim), [email protected] (C. W. Lee), [email protected] (H. Choi)

ACKNOWLEDGMENT This study was supported financially by Samsung Research Funding Center of Samsung Electronics under Project Number SRFC-MA1501-06 and by the National Research Foundation of Korea (2014R1A2A1A01005862, 2015R1C1A1A02036599).

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Films 2013, 531, 385-390. (42) Ko, S.-J.; Choi, H.; Lee, W.; Kim, T.; Lee, B. R.; Jung, J.-W.; Jeong, J.-R.; Song, M. H.; Lee, J. C.; Woo, H. Y.; Kim, J. Y. Highly Efficient Plasmonic Organic Optoelectronic Devices Based on a Conducting Polymer Electrode Incorporated with Silver Nanoparticles. Energy Environ. Sci. 2013, 6, 1949-1955. (43) Zhang, W.; Zhao, B.; He, Z.; Zhao, X.; Wang, H.; Yang, S.; Wu, H.; Cao, Y. HighEfficiency

ITO-Free

Polymer

Solar

Cells

Using

Highly

Conductive

PEDOT:PSS/Surfactant Bilayer Transparent Anodes. Energy Environ. Sci. 2013, 6, 1956-1964.

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