CuâThienoquinone Charge-Transfer Complex: Synthesis

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Organic Electronic Devices

Cu-Thienoquinone Charge-Transfer Complex: Synthesis, Characterization and Application in Organic Transistors Deliang Wang, Xiaolan Qiao, Jingwei Tao, Ye Zou, Hongzhuo Wu, Daoben Zhu, and Hongxiang Li ACS Appl. Mater. Interfaces, Just Accepted Manuscript • DOI: 10.1021/acsami.8b08360 • Publication Date (Web): 18 Jul 2018 Downloaded from http://pubs.acs.org on July 20, 2018

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ACS Applied Materials & Interfaces

Cu-Thienoquinone Charge-Transfer Complex: Synthesis, Characterization and Application in Organic Transistors Deliang Wang,†,§ Xiaolan Qiao,*, † Jingwei Tao,† Ye Zou,‡ Hongzhuo Wu, †,§ Daoben Zhu ‡ and Hongxiang Li*, † †

Key Laboratory of Synthetic and Self-Assembly Chemistry for Organic Functional Materials,

Center for Excellence in Molecular Synthesis, Shanghai Institute of Organic Chemistry, CAS, Shanghai, 200032, China ‡

Beijing National Laboratory for Molecular Sciences, CAS Key Laboratory of Organic Solids,

Institute of Chemistry, CAS, Beijing, 100190, China §

University of Chinese Academy of Sciences, Beijing, 100049, China

KEYWORDS: Charge transfer complex, organic transistor, copper electrode, doping layer, ntype organic transistor, organic electronics

ABSTRACT: A facile and unusual reaction between thienoquinone compound QDTBDT2C and copper is reported. The formation of Cu-QDTBDT2C complex is proved by absorption spectra, IR spectra, Raman spectra and XPS data. This complex can serve as doping layer at the interface of Cu / QDTBDT2C and greatly improve the performance of organic transistors in

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which copper electrode is source / drain electrodes and QDTBDT2C is active layer. The transistors display an electron mobility of 0.95 cm2V-1s-1, to our knowledge, the highest electron mobility reported for copper electrode-based n-type transistors and nearly two times higher than the Au electrode based devices. These results demonstrate the potential applications of CuQDTBDT2C complex in organic electronics, and the unique properties of QDTBDT2C (spontaneously reacting with copper) provide a new insight into the design of n-type organic semiconductors for copper electrode based organic transistors.

INTRODUCTION

Organic charge-transfer (CT) complexes have been widely studied due to their unique properties, such as electrical conductivity, 1-4 ferromagnetism, 5-8 and nonlinear optical property. 9-12

Electron-donating (D) and electron-accepting (A) molecules are the two components of CT

complex. The organic compounds with low LUMO energy level can act as electron-accepting molecules, and the electron-donating component can be metals or organic molecules with high HOMO energy levels. Among these CT complexes, M-TCNQs (M=Cu, Ag), which are prepared through the reaction between tetracyanoquinodimethane (TCNQ) and metals, are one of the most famous and benchmark ones. M-TCNQs have found applications in switch and data storage.13-18 Besides that, M-TCNQs can serve as electrode doping materials to improve the electrode / organic layer contact in organic transistors.19,20 M-TCNQs decrease the hole injection barrier by increasing the work function of metal electrodes, and hence improve the performance of p-type organic transistors. Copper, which has suitable work function (4.6 ~ 4.8 eV) and offers excellent electrical conductance, is an alternative electrode material for organic transistors with low cost.21,22


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However, copper facilely forms CuOx at the interface of organic semiconductor and copper electrode which lowers the transistor performance, and thus copper electrode based organic transistors are rarely reported. The application of Cu-TCNQ complex as electrode doping materials strongly improves the feasibility of copper electrodes in organic transistors.

23,24

Unfortunately, the reported Cu / Cu-TCNQ based organic transistors are usually p-type ones and display lower or comparable performance when compared with their Au electrode counterparts. Thienoquinones have similar chemical structures as TCNQ and are promising n-type organic semiconductors.25-29 Unlike TCNQ, it is believed that thienoquinones cannot react with copper and form charge transfer salts due to their higher lying LUMO energy levels (usually > -4.4 eV, higher than the Fermi level of copper). Herein, we reported an unusual and facile reaction between thienoquinone QDTBDT2C (LUMO energy level: -4.39 eV, the CV curve of QDTBDT2C was shown in Figure S1) and copper (Scheme 1a-b). The formation of CuQDTBDT2C complex was confirmed by colour change, absorption spectra, Raman spectra, IR spectra and XPS results. This complex can be synthesized spontaneously and serve as doping layer at metal / semiconductor interface in thin film transistors in which the active layer was QDTBDT2C and the source / drain electrodes were copper electrodes. The transistors displayed a high electron mobility up to 0.95 cm2V-1s-1. To our knowledge, it is the highest performance reported for copper electrode-based n-type organic transistors and nearly two times higher than the Au electrode-based transistors.30 The unique properties of QDTBDT2C (spontaneously reacting with copper) provide a new insight into the design of n-type organic semiconductors for copper electrode based organic transistors.


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Scheme 1. (a) Chemical structure of QDTBDT2C; (b) reaction between copper and QDTBDT2C; (c) colour of copper film and Cu-QDTBDT2C film. RESULTS AND DISCUSSION Scheme 1c illustrates the colour changes of a copper film (vacuum deposited on a SiO2 substrate) before and after dipping into a QDTBDT2C solution. The copper film was firstly dipped into a chloroform solution of QDTBDT2C for 3 hours, and then washed with chloroform for several times to remove the unreacted QDTBDT2C. The distinct colour change indicated a reaction occurred between copper and QDTBDT2C. Besides copper films, copper powder also reacted with QDTBDT2C, which was proved by the gradual colour fading of the solution. The formed Cu-QDTBDT2C has poor solubility in organic solvents, and thus it is impossible to purify Cu-QDTBDT2C from the unreacted copper, hence the attempt to obtain its elementary analysis data failed. The UV-vis absorption spectra of Cu-QDTBDT2C, QDTBDT2C and copper thin films are shown in Figure 1a. It is clearly seen, after reacting with copper, the typical absorption of QDTBDT2C at 680 nm disappeared, and a strong peak in the IR region


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(1270 nm) was observed, further proving the reaction between copper and QDTBDT2C. This IR region absorption was ascribed to the charge - transfer absorption of CuQDTBDT2C.

Figure 1. (a) UV-vis absorption spectra of Cu-QDTBDT2C, QDTBDT2C, and copper thin films; (b) IR spectra of Cu-QDTBDT2C and QDTBDT2C in solid state (c) Raman spectra of Cu-QDTBDT2C and QDTBDT2C in solid state. Infrared spectroscope (IR) and Raman spectroscope are useful tools for characterizing quninone–type charge transfer complexes.27,28 Cu-QDTBDT2C and QDTBDT2C exhibited distinct IR and Raman spectra in solid state (Figure 1b and 1c).

Cu-

QDTBDT2C showed two strong and broad ν (CN) absorptions at 2191 cm-1 and 2141 cm-1 in IR spectrum (Figure 1b), whereas QDTBDT2C exhibited a strong and sharp stretch at 2208 cm-1 with a shoulder at 2193 cm-1. The blue-shifted ν (CN) in wave


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number of Cu-QDTBDT2C proved its charge transfer character.31,32 In Raman spectra, QDTBDT2C showed intense peaks in the range of 1500-1100 cm-1 together with a ν (CN) band at 2209 cm-1. For Cu-QDTBDT2C, the ν (CN) Raman band was unidentified which was similar as that of Cu-TCNQ.33 At the same time, the peaks of QDTBDT2C at 1500-1100 cm-1 were blue-shifted in wave number when compared with those of CuQDTBDT2C, which was ascribed to the recovery of the aromatic character of the quinone backbone.34

Figure 2. (a) XPS and (b) UPS of copper dipped in a chloroform solution of QDTBDT2C with varied time. X-ray photoelectron spectroscopy (XPS) and ultraviolet photoelectron spectroscopy (UPS) were used to measure the oxidation state of copper in Cu-QDTBDT2C complex and the work function of Cu-QDTBDT2C film respectively. XPS data (Figure 2a) revealed the characteristic binding energies for Cu(I) 2p1/2 and 2p3/2, with no evidence for shoulders or higher binding energy satellites that could be attributed to Cu(II). The


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formation of Cu(I) was further confirmed by Cu LMM auger spectra. It is clearly seen that the proportion of 916.63 eV peak (refer to the oxidation state of Cu, Cu (I)) intensity was obviously increased with the increase of dipping time (from 0 h to 3 h), while the Cu(0) proportion (918.4 eV) decreased and finally disappeared when the dipping time was 6 hours, indicating the film surface was fully covered with Cu-QDTBDT2C. Please note, the 916.63 eV peak for pure copper film was ascribed to the small amount of surface native oxidized Cu (Cu2O). UPS results showed the surface work function of the film gradually increased with the coverage of Cu-QDTBDT2C, e.g., 4.61 eV for the freshly deposited copper film and 4.85 eV for the fully covered Cu-QDTBDT2C film (Figure 2b). The formation of Cu-QDTBDT2C should be responsible for the increased surface work function of film.

Figure 3. (a-f) AFM height images of copper dipped into a chloroform solution of QDTBDT2C with varied time.


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AFM images of Cu-QDTBDT2C films prepared by dipping fresh deposited copper films into 1.0 mg / mL QDTBDT2C chloroform solution with varied time are shown in Figure 3a-f. As the dipping time increased, the RMS values of Cu-QDTBDT2C films significantly increased corresponding to the enlarged grain size. The growth of grain size is attributed to the dissolution and re-precipitation of Cu-QDTBDT2C on the film surface. Unlike Cu-TCNQ, the thickness of Cu-QDTBDT2C films was usually in the range of several to twenty nanometers because of the poor solubility of Cu-QDTBDT2C. Please note, when a 10 nm copper film was dipped into QDTBDT2C solution for 24 hours, unreacted copper film was also observed. The ultrathin feature of Cu-QDTBDT2C film suggested its potential applications as electrode doping layer in organic transistors.

Figure 4. Transfer curve (a) and output curve (b) of the copper electrode-based transistors after storage in N2-filled glovebox for 68 hours. To explore the application of Cu-QDTBDT2C complex as electrode doping layer, bottom-gate / top-contact (BGTC) configuration organic transistors were fabricated by using QDTBDT2C as semiconductor layers and copper as source-drain electrodes. The


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newly fabricated device showed an electron mobility of 0.64 cm2V-1s-1. Interestingly, the device displayed an electron mobility of 0.95 cm2V-1s-1 after being stored in a N2-filled glovebox for 68 hours. This value is approximately 2 times of the optimal Au electrodebased devices (0.57 cm2V-1s-1, Figure S2) in which same device structure was adopted and QDTBDT2C films were deposited under the same conditions.30 To our knowledge, it is the highest performance reported for copper electrode-based n-type organic transistors. The representative transfer and output curves of the transistors are shown in Figure 4. The time dependence of the transistor characteristics of Cu electrode-based devices was shown in Table S1. We believe, the performance improvement of transistor after 68 hours is due to the formation of Cu-QDTBDT2C doping layer (the reaction rate of QDTBDT2C films with copper is much slower than that of QDTBDT2C solution with copper). The formation of Cu-QDTBDT2C doping layer was proved by absorption spectra. When QDTBDT2C was spin-coated on a copper film (deposited on quartz substrate), the typical absorptions of Cu-QDTBDT2C were observed after the substrate was stored in N2-filled glovebox for 24 hours, and the intensity of these absorptions gradually increased with the time. Due to the much slowly reaction rate of QDTBDT2C films with copper electrode, the formed Cu-QDTBDT2C layer is ultrathin. The effect of the formation of ultrathin Cu-QDTBDT2C layer on the crystalline ordering of QDTBDT2C films near metal-semiconductor interface can be negligible in the device because (i) the unreacted QDTBDT2C can not be rearranged at ambient condition, and (ii) the RMS value of pristine QDTBDT2C films is about 3.0 nm (Figure S3). Compared with that of the Au-based device, the higher mobility of the copper electrode-based device cannot be only attributed to the more matched LUMO energy


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level of QDTBDT-2C (-4.39 eV) and the work function of copper electrodes (~4.6 eV). Please note, with the electrode being covered by Cu-QDTBDT2C complex, its work function increased (from 4.61 eV to 4.85 eV), and the energy barrier between the electrode work function and the LUMO energy level of QDTBDT2C enlarged, which is disadvantageous for electron injection. We believe that the ultrathin Cu-QDTBDT2C doping layer shrinks the thickness of space-charge layer formed at the Cu / QDTBDT2C interface, and the electrons can be easily injected from copper electrode to QDTBDT2C by tunnelling instead of thermionic emission.35,36 With this mechanism, the electron injection will not be limited by the injection barrier between the electrode work function and the LUMO energy level of QDTBDT2C, and quasi-Ohmic contact between electrode / organic semiconductor will be formed. As shown in Figure 4b, the output curve at VDS < VGS exhibits linear current-voltage relationship, indicating the formation of Ohmic contact at Cu / QDTBDT2C interface. Currently, the thorough investigation of electron injection mechanism is under the way. CONCLUSION In conclusion, an unusual reaction between thienoquinone compound QDTBDT2C and copper was reported. The formation of Cu-QDTBDT2C complex was confirmed by absorption spectra, IR spectra, Raman spectra and XPS data. This complex can be spontaneously formed at the interface of Cu / QDTBDT2C and greatly improve the performance of organic transistors in which copper served as source / drain electrodes and QDTBDT2C served as active layer. The transistors displayed an electron mobility of 0.95 cm2V-1s-1, nearly two times higher than the Au electron-based devices. To our knowledge, this is the highest electron mobility reported for copper electrode-based n-type transistors. All these results demonstrate the potential applications


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of Cu - thienoquinone complex in organic electronics and provide a new insight into the design of high performance n-type organic semiconductors for copper electrode based organic transistors. EXPERIMENTAL SECTION QDTBDT2C was prepared according to previously published procedures. 30 Preparation of Cu-QDTBDT2C film: The copper film (vacuum deposited on a SiO2 substrate with a thickness of 50 nm) was firstly dipped into a chloroform solution (1 mg / mL) of QDTBDT2C for 3 hours, and then washed with chloroform for several times to remove the unreacted QDTBDT2C. Preparation of samples for UV-vis absorption spectra Measurement: Copper was deposited on a quartz slice with a thickness of 10 nm, and then the slice was immersed into a chloroform solution (1 mg / mL) of QDTBDT2C for 12 hours. After that, the slice was washed with chloroform for several times. Finally, the absorption spectrum was obtained on a U-3900 UV-vis spectrophotometer. Device Fabrication and Characterization: Bottom-gate / top-contact (BGTC) transistors were fabricated. Si / SiO2 (300 nm SiO2 with a dielectric capacitance C = 10 nF / cm2) was used as substrate. Cleaning of Si wafers and modification with n-octadecyltrichlorosilane (OTS) were performed according to the reported procedure.

30

Subsequently, the QDTBDT2C films was

spin-coated from chloroform solution (5 mg / mL) on OTS-modified SiO2 surface at 5000 rpm for 30 s under ambient conditions. Finally, 50 nm copper source and drain electrodes were deposited by vacuum evaporation through a shadow mask. The characteristics of the transistors were conducted by using a Keithley 4200 semiconductor parameter analyzer under ambient conditions. The mobilities (µ) were calculated from the data in the saturated regime according to


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the equation ISD = (µWCi/2L)(VG−VT)2, where ISD is the drain current in the saturated regime, W (273 µm) and L (31 µm) are the semiconductor channel width and length, respectively, Ci is the capacitance per unit area of the gate dielectric layer, and VG and VT are the gate and threshold voltages, respectively. The XPS and UPS experiments were performed using an Axis Ultra DLD (Kratos, UK) ultrahigh vacuum photoelectron spectroscopy with a monochromatic Al Kα X-ray (1486.6 eV) and a He-discharge lamp (21.22 eV) as the excitation sources at base pressure better than 5×10-9 Torr.

ASSOCIATED CONTENT Supporting Information The CV curve and absorption spectra of QDTBDT2C in solution. Transfer and output characteristics of QDTBDT2C devices based on Au electrodes. AFM image, 1D-GIXD and 2DGIXD pattern of QDTBDT2C films. This material is available free of charge via the Internet at http://pubs.acs.org AUTHOR INFORMATION Corresponding Author * E-mail: [email protected]; [email protected] Notes The authors declare no competing financial interest. ACKNOWLEDGMENT


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This work was supported by the National Natural Science Foundation of China (Grant Nos.21672252, 21472116 and 21790362), the “Strategic Priority Research Program” of the Chinese Academy of Sciences (XDB12010100), Shanghai Rising-Star Program (18QA1405000) and Youth Innovation Promotion Association of Chinese Academy of Sciences (2018290).


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CuâThienoquinone Charge-Transfer Complex: Synthesis

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CuâThienoquinone Charge-Transfer Complex: Synthesis