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Morphological Behavior of Printed Silver Electrodes with Protective Self-Assembled Monolayers for Electrochemical Migration Tomohito Sekine, Jun Sato, Yasunori Takeda, Daisuke Kumaki, and Shizuo Tokito ACS Appl. Mater. Interfaces, Just Accepted Manuscript • DOI: 10.1021/acsami.8b02996 • Publication Date (Web): 17 Apr 2018 Downloaded from http://pubs.acs.org on April 17, 2018

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ACS Applied Materials & Interfaces

Morphological Behavior of Printed Silver Electrodes with Protective Self-Assembled Monolayers for Electrochemical Migration Tomohito Sekine*, Jun Sato, Yasunori Takeda, Daisuke Kumaki, and Shizuo Tokito* Research Center for Organic Electronics (ROEL), Graduate School of Science and Engineering, Yamagata University, Yonezawa, Yamagata 992-8510, Japan KEYWORDS: printed electrode, self-assembled monolayer, electrochemical migration, organic electronics, surface functionalization

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ABSTRACT: We evaluated the electrochemical behaviors and reliability of printed silver (Ag) electrodes prepared from nanoparticle inks with the use of protective self-assembled monolayers (SAMs) under electronic bias conditions. The printed Ag electrodes were fabricated by inkjet printing on a hydrophobic substrate. The SAMs, which acted as barriers to moisture, were prepared by immersing the substrate in a pentafluorobenzenethiol (PFBT) solution under ambient temperature (25 °C). We investigated the electrochemical migration phenomenon using the water drop method, and the results showed that the formation of dendrites connecting the cathode and the anode, which can affect the electrochemical reliability of an electric device, was suppressed in the presence of the SAMs. The time before short circuit occurred was found to depend on the spacing between the electrodes, i.e., 130 s when the distance between the electrodes was 200 μm in the presence of a SAM. We demonstrated that Ag electrodes treated using the procedure described in this work suppress the occurrence of electrical short circuits caused by Ag dendrite formation, and thus, their electrochemical properties are substantially improved.

INTRODUCTION Organic electronics have a number of potential uses in wearable or large-area applications such as sensors,1,2 flexible displays,3,4 and photovoltaics.5,6 Their devices possess great potential for novel applications such as wearable and disposable healthcare applications. In particular, wearable physical sensors and bio-sensors must operate continuously and reliably, e.g., in 24-h healthcare monitors.7,8 In many cases, the wearable devices are used by attaching them to the human skin with adhesion patches to monitor health conditions. These devices will be fabricated using printing processes for low-cost and large-scale production in near future.


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In wearable devices attached to the human body in the form of an adhesive patch, electrochemical migration is an important issue because electrolysis reactions involving environmental moisture and sweat from the human body can occur in the printed electrodes.9-12 Electrochemical migration is the diffusion of metal ions such as Ag+ through an aqueous electrolyte between two electrodes under bias voltages, and it causes short-circuit failure of the electronic components because of the formation of a conductive dendrite between the anode and the cathode across a nonmetallic medium.13–16 The mechanism of electrochemical migration is described by the following two equations: Ag → Ag + + 𝑒 − H2 O + 𝑒 − →

(1)

1 H + OH − 2 2

(2)

Eq. (1) shows the chemical reaction for the elution of Ag at the anode, and eq. (2) represents the electrolysis of water at the cathode. The Ag+ ions generated at the anode move toward the cathode and react with the OHˉ ions generated at the cathode. 2Ag + + 2OH − ↔ 2AgOH ↔ Ag 2 O + H2 O

(3)

At the cathode, electrons reduce the Ag+ ions, and this reaction leads to the precipitation of metallic Ag and the consequent growth of dendrites. Ag + + 2OH − → Ag (↓)

(4)

Dendrite growth at the cathode occurs by the precipitation of metal ions that were dissolved at the anode, thus giving rise to tree-like formations.17,18 It is essential to analyze the cumulative electrochemical behavior in the presence of dendrites under various environmental conditions. Thus far, previous researches have been extensively studied the effects of thermally deposited or sputtered Ag electrodes on electrochemical migration. Simultaneously, countermeasures have been proposed for electrochemical migration of the thermally deposited or sputtered Ag electrode.


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For instance, the long-term stability of the thermally deposited or sputtered Ag electrode toward moisture is improved by developing encapsulation layers.19 Moreover, the increase in resistance between an anode and a cathode is reduced by forming alloys with silver and palladium pastes.20 However, in the near field of printed electronics, there are very few reports on fabrication processes related to electrochemical migration.21,22 In addition, no studies on the electrochemical barrier efficiency of self-assembled monolayers (SAMs) on printed electrodes have been reported so far. In this study, we show that the treatment of printed Ag electrodes with SAMs enhances their electrochemical durability and reliability by suppressing the electrochemical migration phenomena. We found that the time required to short-circuit the electrodes, a phenomenon caused by the dendrite growth, depends on the spacing between the electrodes. In the case of the most distantly spaced electrodes considered in this study (200 μm), short circuit occurred after 130 s. The electrochemical characterization results for the printed Ag electrodes confirmed the successful functionalization of the electrodes using SAMs.

METHODS Figure 1a shows a cross-sectional image of the electrodes fabricated on a substrate using the printing method. A photograph of the Ag electrodes with a patterned print on an hydrophobic insulating layer (Teflon, AF1600®, DuPont) is shown in Figure 1b. The Teflon layer was treated with weak oxygen plasma to improve wettability. Ag nanoparticles dispersed in tetradecane with a Ag concentration of 55 wt% (NPS-JL, Harima Chemicals, Inc.) were used for the printed electrodes. The Ag nanoparticle ink was patterned on the electrodes by inkjet printing (DMP-2831, Fujiﬁlm Dimatix Co.). The 10 pL cartridge and stage were kept at 40 and 50 °C, respectively, and


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the drop spacing was 60 µm. The patterned silver ink was then sintered at 150 °C for 1 h in air. The scanning speed of the 10 pL cartridge was approximately 60 mm s-1. SAM treatment of the printed electrodes was carried out by immersing the substrate in a 5 mM 2-propanol solution of pentafluorobenzenethiol (PFBT, Figure 1c) for 5 min at ambient temperature (25 °C). The PFBT concentration was optimized in our previous work.23,24 The substrate was then rinsed with pure 2propanol solution and blow-dried with nitrogen. The distances between the printed electrodes were set at 50, 100, and 200 μm. According to previous reports, the thiol groups of a SAM bonds well with silver.25,26 Moreover, a SAM can improve the surface morphology of the electrodes and modify the contact angle with solvents.27, 28 Thus, the SAM layer can prevent the contact between printed electrodes and moisture. In fact, similar to our research, previous researchers have reported the effects of barrier layers on electrodes against electrochemical migration.19 Figure S1 (Supporting Information) shows the coverage of PFBT on the printed electrode by SEM-EDS (JSM7600FA, JEOL). The measured coverage was approximaly 70 to 100 %. We assessed the degree of electrochemical migration in the printed electrodes using the water drop method.29,30 In this method, we dropped 0.2 ml of pure water filtered by ion exchange resin (resistance of the filtered pure water was approx. 10 MΩ cm) on the printed electrodes. The Ag dendrite growth is classified as an Ag-induced contamination on the cathode electrode in pure water. In order to quantify this effect, a current of 0.5 A was applied between the printed electrodes and the resistance was measured as a function of voltage. The electrical characteristics of the electrode were measured at ambient temperature (25 °C) using a multimeter (34460A, Keysight). In this work, the resistance between the electrodes measured 1 s after the application of the voltage bias was considered as the reference initial resistance. When the resistance became 0.2 times the initial


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value, a short circuit was assumed to have occurred between the electrodes because of dendrite growth. This method followed the JPCA-ET01-09 and ISO 9455-17 standards.

Figure 1. Fabricated Ag electrodes. (a) Cross-sectional schematic of the fabricated electrodes on a substrate prepared by the inkjet printing method. (b) Optical microscope image of printed Ag electrodes on an insulating layer. The scale bar is 50 μm. (c) Chemical structure of PFBT molecule.


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RESULTS AND DISCUSSION Figure 2a shows the scanning electron microscope (SEM) (JSM7600FA, JEOL) and the transmission electron microscope (TEM) (JEM2100F, JEOL) images of a printed Ag electrode after annealing at 150 °C and a thermally deposited Ag electrode. In the printed Ag electrode, the Ag particles converted into bulk Ag during annealing, which leads to a decrease in the resistivity of the electrode as the annealing temperature increases. The dependence of the resistivity on the annealing temperature is shown in Figure 2b. At annealing temperatures exceeding 120 °C, the measured resistivity was found to be lower than 50 µΩ cm. A minimum resistivity of 8.0 µΩ cm was obtained at a sintering temperature of 160 °C, which was approximately five times higher than the resistivity of bulk Ag (1.6 µΩ cm).31 These results indicated that the printed electrodes obtained from Ag nanoparticle inks are suitable for electrochemical migration tests because they are similar to electrodes obtained by thermal deposition. Figure 2c shows the cross-sectional profiles of the printed Ag electrodes. The shape of the electrodes remained unchanged at several annealing temperatures.


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Figure 2. Characteristics of the printed Ag electrodes. (a) Surface SEM images of a printed Ag electrode after annealing at 150 °C and of an Ag electrode obtained by thermal deposition (left). A 100 nm scale bar is indicated. Magnified TEM images of the printed and thermally deposited Ag electrodes (right). A scale bar of 5 nm is indicated. (b) Resistivity of the printed Ag electrode as a function of annealing temperature. (c) Cross-sectional profiles of printed Ag electrodes at annealing temperatures of 120–160 °C.

Figure 3 illustrates the electrochemical migration behavior of the printed electrodes, as determined using the water drop method. Figure 3a–c show the resistance changes of the printed electrodes as a function of the applied bias voltage time. Electrodes without SAMs (w/o SAM) were found to short-circuit after 5–20 s depending on the spacing between the electrodes, whereas


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the electrodes with a SAM coating (w/ SAM) exhibited marked improvements in electrochemical reliability. In the latter case, the short-circuit time was again found to depend on the separation between the electrodes, which is 130 s in the case of the largest electrode separation (200 μm) (Figure 3c), a value much higher than those of the untreated electrodes. Figure 3d shows the shortcircuit time as a function of the space length of the printed Ag electrodes. As expected, the SAMcoated Ag electrodes exhibited substantial improvement in their electrochemical reliability. These results showed that PFBT SAMs could effectively hinder the electrolysis of water in the presence of Ag.

Figure 3. Electrochemical migration behavior of the printed electrodes using the water drop method. Anode/cathode resistance change as a function of applied bias voltage time for electrodes w/o SAM and w/ SAM. The electrode separations are 50 μm (a), 100 μm (b), and 200 μm (c). (d) Anode/cathode short-circuit time as a function of electrode spacing.


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Figure 4 shows the Ag dendrite growth between the printed anode and the cathode. Figures 4a– c show the optical microscope images of the printed electrodes before applying a voltage bias. Figures 4d–f show the Ag dendrite growth of the printed Ag electrodes without a SAM coating. A voltage bias was applied continuously for 20 s. In this case, the Ag dendrites connected the electrodes, irrespective of the separation between the electrodes. The green dashed lines indicate the short-circuit point formed when a dendrite comes in contact with the anode. In this work, we found that the Ag dendrites formed polyhedral crystals because the applied voltage was close to the voltage required for the electrolysis of water (around 0.8 V).15 In contrast, in the case of SAMcoated electrodes, the dendrites did not come in contact with the electrodes (Figures 4g–i). Figure S2 (Supporting Information) shows Ag dendrimer growth and dissolution of the printed Ag w/ SAM electrodes when a voltage bias was applied for 150 s. From these results, it is cleared that the SAM coating can effectively control the electrochemical migration in printed Ag electrodes. Furthermore, in this case, the short-circuit time depended on the distance between the electrodes. The effects of printing conditions such the speed of inkjet deposition, electrode thickness, and annealing temperature on electrochemical migration are shown in Figures S3, S4, and S5 (Supporting Information). These results indicate that the above-mentioned printing conditions of the electrode did not affect electrochemical migration. Moreover, the thicker part around the printed electrode edge (ring of coffee stain32) also did not affect electrochemical migration (see Figure S6, Supporting Information). The results of our study will be of relevance for the development of new printed organic electronic devices with enhanced reliability and efficiency.


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Figure 4. Ag dendrite growth between anode and cathode. (a)–(c) Optical microscope images of printed Ag electrode before applying voltage bias. A scale bar of 100 µm is indicated. (d)– (f) Ag dendrimer growth and dissolution of printed Ag w/o SAM electrodes. A voltage bias was applied for 20 s. The scale bars are 10 μm (d), 20 μm (e), and 40 μm (f). Inset SEM images show surface morphological behavior near the cathode electrodes. The scale bars are 500 nm. (g)–(i) Ag dendrimer growth and dissolution of printed Ag w/ SAM electrodes. A voltage bias was applied for 20 s. The scale bars are 10 μm (g), 20 μm (h), 40 μm (i).


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To confirm the nature of the surface states after the PFBT treatment, we analyzed the SAMs by X-ray photoelectron spectroscopy (XPS) (Figures 5a–c). The results clearly show the presence of silver (Ag 3d), thiol (S 2p), and fluorine (F 1s) on the printed Ag electrode before and after SAM coating. Furthermore, we determined the water contact angles on the surface of the treated Ag electrodes using a contact angle goniometer, as shown in Figures 5d and 5e. The water contact angle of the SAM-treated Ag electrode (92.2 ± 3.8°) was found to be higher than that of the untreated Ag electrode (60.5 ± 2.3°), which was most likely a consequence of the hydrophobicity of the SAM. Additionally, Figure 5f shows the X-ray diffraction (XRD) patterns of the Ag electrode before and after SAM treatment, which reveal the presence of several lattice planes, including (111), (200), (220), and (311).33,34 This indicated that the crystalline structure at the Ag electrode is unaffected by the presence of the SAM and that the treatment with PFBT only modifies the nature of the electrode surface. The electrochemical behavior of the printed Ag electrodes confirmed that the functionalization of the treated electrodes was successfully achieved and that the SAM coating substantially improves the electrochemical reliability of the electrodes.


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Figure 5. Surface analysis of the printed Ag electrodes. (a-c) XPS spectra of Ag electrodes treated with PFBT and untreated Ag electrodes: (a) silver (Ag 3d), (b) thiol (S 2p), and (c) fluorine (F 1s). Water contact angle measurements on printed Ag electrodes w/ SAM (d) and w/o SAM (e). (f) XRD patterns showing (111), (200), (220), and (311) lattice planes of printed Ag electrodes with (w/ SAM) and without (w/o SAM) PFBT treatment.


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CONCLUSIONS In summary, we describe a strategy for improving the resistance of printed Ag electrodes toward electrochemical migration based on the creation of a protective SAM on the surface of the electrodes. The SAM coating was obtained by treating the printed electrodes with PFBT. The electrodes with SAM coating exhibited substantial improvements in their electrochemical reliability compared to the uncoated ones. Moreover, the short-circuit time was found to depend on the spacing between the electrodes. In the case of largest electrode distance (200 μm), the shortcircuit time was 130 s, which is considerably larger than the typical short-circuit times for uncoated Ag electrodes. The improved electrochemical properties of the SAM-coated Ag electrodes indicate that our procedure successfully achieves the functionalization of the electrode surface with PFBT. The results of our study will be of relevance for the development of new printed organic electronic devices with enhanced reliability and efficiency.


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ASSOCIATED CONTENT Supporting Information. The Supporting Information files are available free of charge on the ACS Publication website at DOI: XXX. Measurement for coverage of PFBT on the printed Ag electrode (Figure S1); Ag dendrimer growth and dissolution of the printed Ag w/ SAM electrodes (Figure S2); Effects of printing speed of inkjet deposition on electrochemical migration (Figure S3); Effects of thickness of the printed Ag electrode on electrochemical migration (Figure S4); Effects of annealing temperature of the printed Ag electrode on electrochemical migration (Figure S5); Developed points of the dendrimer against thickness direction of the printed electrode (Figure S6).

AUTHOR INFORMATION Corresponding Author *E-mail: [email protected], [email protected] ORCID Tomohito Sekine: 0000-0002-2821-1104 Author Contributions The manuscript was written through contributions of all the authors. All authors have given approval to the final version of the manuscript.


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Notes The authors declare no competing financial interest. ACKNOWLEDGMENT We gratefully acknowledge financial support from the Japan Science and Technology Agency (JST). We also thank Mr. C. Shepherd, Mr. S. Yoshida, Dr. R. Sugano, and Dr. H. Matsui of Yamagata University ROEL for their technical support and valuable feedback. The authors would like to thank Editage (www.editage.jp) for the English language review. ABBREVIATIONS SAM, self-assembled monolayer; PFBT, pentafluorobenzenethiol; XPS, X-ray photoelectron spectroscopy; XRD, X-ray diffraction; SEM, scanning electron microscope; SEM-EDS, scanning electron microscope-energy dispersive X-ray spectroscopy; TEM, transmission electron microscope.

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