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High-Performance Field-Effect Transistor Based on Novel Conjugated PO-Fluoro-P-Alkoxyphenyl-Substituted Polymers by Graphdiyne Doping Weiwei Cui, Mingjia Zhang, Ning Wang, Jianjiang He, Jiaojiao Yu, Yun-Ze Long, Shi-Ying Yan, and Changshui Huang J. Phys. Chem. C, Just Accepted Manuscript • DOI: 10.1021/acs.jpcc.7b07364 • Publication Date (Web): 09 Oct 2017 Downloaded from http://pubs.acs.org on October 9, 2017

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The Journal of Physical Chemistry

High-Performance Field-Effect Transistor Based on Novel Conjugated P-O-Fluoro-P-AlkoxyphenylSubstituted Polymers by Graphdiyne Doping Weiwei Cui,a Mingjia Zhang,b,* Ning Wang,b Jianjiang He,b Jiaojiao Yu,b Yunze Long,a,* Shiying Yan,a,* and Changshui Huangb,* a

Department of Physics, Qingdao University, Qingdao 266071, P.R. China

b

Qingdao Institute of Bioenergy and Bioprocess Technology, Chinese Academy of Sciences,

Qingdao 266101, P.R. China

Abstract: The novel two-dimensional graphitic material, graphdiyne (GDY), has attracted great interest due to its superior stability and natural semiconductor characteristic. We realize the obvious improvement of carrier transport characteristics of P-o-FBDTP-C8DTBTff (PFC) organic polymer semiconductor via adding GDY. The result of the field effect transistor measurement suggests that doping GDY can dramatically improve the on/off ratio and threshold voltage of organic semiconductor. Especially the mobility of GDY/PFC film is two orders of magnitude higher than pristine PFC, demonstrating the important role of GDY dopant. Besides, the carrier diffusion length of GDY/PFC film is also enhanced, suggesting the great potential applications of GDY-modified polymer with donor-acceptor units in organic photoelectric device. 1. Introduction

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Semiconducting conjugated polymers have been widely used in many fields such as polymer solar cell,1,2 organic field-effect transistor,3,4 photoelectric device5 and so on, owing to their cheap fabrication cost,6 flexibility7 and easy manipulation8 by solution process. Among different materials, conjugated polymer with alternating donor-acceptor (D-A) with BDT unit draws much attention due to the adjustment of energy gap2 and mobility by changing the chemical structure. Especially in recent years, a novel donor-acceptor polymer with fluorinated BDT unit, has been synthesized to fabricate bulk heterojunction polymer solar cell and achieved a high power conversion efficiency of 9%,9 indicating a promising application prospect in organic photovoltaic conversion or semiconductor optoelectronic devices. However, the mobility of this polymer is only 1.5×10-4 cm2·V-1·s-1 determined by Takayuki Nagano,10 which is relatively low and accelerates the carrier recombination process, restricting its application in photoelectric devices. During the past decade, carbon materials such as carbon nanotube or graphene with very high mobility have been widely combined with conjugated polymer as an additive to improve the carrier transport properties of composite thin-film, since these carbon materials can provide good connection between the crystalline regions and the semiconductor film.11,12 Particularly, the mobility and the on/off ratio of organic field-effect transistors (OFET) can be significantly improved by incorporating two-dimensional graphene or graphene oxide flakes. As for the BDT unit functionalized polymer semiconductors, it would also be of importance to enhance the carrier transport properties by doping with carbon materials. Recently, a novel two-dimensional carbon material, GDY,13 has attracted much attention due to the unique network containing sp- and sp2-hybridized carbon atoms as well as with high mobility characteristics. Similar with graphene flakes, GDY flakes have been also successfully applied in the property modification of organic charge transport layer such as P3HT,14 PEDOT15


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and PCBM16 in perovskite solar cells. The enhancement of photoelectric conversion efficiency can be attributed to the improvement of interfacial morphology and interface matching. For example, GDY can provide better percolation paths, improve the electron transport efficiency17 and accelerate the hole extraction,18 GDY may also help to passivate the grain-boundary of the perovskite and then reduce the trap states of the surface to eliminate the recombination.19 Considering the advantages of GDY such as its special networks with delocalized π-systems and unique conductivity advantage,

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GDY can also be adopted as a novel additive in BDT unit

functionalized polymer semiconductors to modify the OFET output performance as well as carrier transport properties, which may provide us a simple and efficient method to explore composite organic photovoltaic material with high performance. In this study, we present an efficient way to improve the mobility of organic field effect transistor by doping GDY into the PFC, and find that GDY can better improve the carrier transport characteristics of PFC. The mobility of OFET devices is significantly raised to 0.69 cm2·V-1·s-1 from 0.002 cm2·V-1·s-1 with doping GDY, and meanwhile the on/off ratio increases by about three orders of magnitude, which can be attributed to the improved interfacial level matching. More importantly, the carrier diffusion length of GDY-doped PFC can achieve twenty times longer than that for the raw material, which may contribute to the application of PFC in high-efficient photovoltaic conversion devices. These results may not only provide a deep insight into carrier transport property modification in organic polymer semiconductor but also promote the related photoelectric device design by doping with 2D carbon material. 2. Experiment 2.1.

Fabrication

and

characterization

of

GDY

doping

P-o-FBDTP-C8DTBTff.

Chlorobenzene, sodium hydroxide, hydrochloric acid, and N, N dimethyl formamide (DMF)


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were purchased from Sigma-Aldrich and used as received without further purification. PFC powder was obtained through the synthetic route in ref.2020 and GDY powder was obtained through the synthetic route in ref.21.21 Here it should be noted that the raw GDY powder must be cleaned twice by ultrapure water and N, N dimethyl formamide (DMF) in turn, and then the GDY are heated and stirred for 3h in 3M hydrochloric acid and 3M sodium hydroxide to remove the residual copper and silicon respectively. At last, the GDY are cleaned by deionized water and ethyl alcohol until the supernatant is colorless. To fabricate the composite, 5 mg PFC and 0.5 mg GDY powders were dissolved in 500 ul chlorobenzene. This solution was under ultrasonic treatment for 6h and then the mixture was stirred for 4h to realize complete recombination. UVvis measurement was performed using the Hitachi U-4100 spectrometer. The morphology was measured by AFM and SEM. 2.2. FET device fabrication and measurement. PFC and GDY/PFC solutions were spin-coated on silicon wafer covered with 300 nm-thick SiO2 layer at 3000 rpm and then annealed at 100 oC for 10 min. The thickness of film was about 7-8 µm as shown in Figure S1. Subsequently topcontact bottom-gate OFET device was completed by evaporating about 50-100 nm silver source/drain electrodes in vacuum degree below 10-5 for 15 min. The channel length and width were 10 µm and 5 µm respectively. Electrical measurements were performed on back-gated field effect transistors at room temperature in air using a Keithley 4200 Semiconductor Characterization System and Signatonc Probe Station. 2.3. Impedance Spectroscopy. The electrochemical impedance spectra (EIS) was measured by a Zahner electrochemical workstation (Zahner IM6) with different DC bias from 0 to 0.8 V. The frequency of applied ac voltage perturbation was in the range from 7 MHz to 100 MHz with amplitude of 25 mV. Z-View software was utilize to analyze impedance data.


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3. Results and Discussion

Figure 1. The chemical structure of (a) GDY and (b) PFC. (c) C 1s binding energy profiles of GDY. (d) SEM and (e) TEM images of GDY. (f) The optical photograph of the PFC and the GDY/PFC composite precursor solution. Figure 1a shows the chemical structure of GDY containing sp- and sp2-hybridized carbon atoms, which is used as a dopant in this work. Figure 1b is the chemical structure of o-fluoro-palkoxyphenyl-substituted polymers, which has been used to construct donor-acceptor conjugated copolymers with electron-deficient unit 5,6-difluoro-4,7-di(4-(2-ethylhexyl)-2-thienyl)-2,1,3benzothiadiazole (C8DTBTff), named P-o-FBDTP-C8DTBTff (PFC).20 Figure 1c displays the high resolution C 1s XPS spectrum of GDY, which can be fitted and divided into four bonds including C-C (sp2), C≡C (sp), C-O and C=O,22 confirming the coexistence of sp- and sp2hybridized carbon. The morphology of GDY powder characterized by SEM is shown in Figure 1d, which displays a uniform aggregation of particles for the raw GDY powders. Meanwhile, the transmission electron microscope (TEM) image is also obtained to demonstrate the uniform and


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continuous microstructure with stacked layers, which is shown in Figure 1e. The optical photographs of raw GDY solution and GDY/PFC mixed solution are also displayed in Figure 1f.

Figure 2. SEM images of (a) PFC film and (b) composite GDY/PFC film respectively. AFM images of (c) PFC film and (d) composite GDY/PFC film. Figure 2 shows SEM and AFM images of the surface topography of the raw PFC film and the hybrid GDY/PFC composite film. From Figure 2a and 2b, we can see the appearance of GDY in hybrid film after intensive mixing, which is randomly distributed with even micrometersized clusters of GDY. To obtain the influence of GDY doping on polymer film morphology, the detailed AFM surface is measured as shown in Figure 2c and 2d. The average roughness of composite film is nearly unchangeable though some GDY aggregates with average size about 500 nm are observed among the whole thin polymer film. Namely the morphology of GDY/PFC


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further confirms that the hybrid composite can also well cover on the substrate by doping 10% GDY powder. Next, Raman spectra are also used to characterize the interactions between PFC and GDY, which is shown in Figure 3. The raw GDY powder yields a Raman spectra containing three prominent peaks 1382.2cm-1, 1569.5cm-1 and 2189.8 cm-1,where the peak of 1382.2cm-1 is ascribed to the breathing vibration of sp2 carbon domain in aromatic, the peak of 1569.5cm-1 is attributed to the first-order scattering of the E2g mode observed for in-phase stretching vibration of sp2 carbon domains in aromatic rings, and the peak 2189.8 cm-1 can be attributed to the vibration of conjugated diine links.13 PFC powder yields a Raman spectrum containing two intensive peaks 1373 cm-1 and 1550 cm-1 ,where D band (1373 cm-1) is a disordered band associated with structural defect and G band (1550 cm-1) is assigned to the C=C skeletal stretching vibration.13 Compared with the pure PFC and GDY films, the D band of the composite GDY/PFC film displays a slight shift to high frequency. Meanwhile, an obvious peak at 2195.1 cm-1 corresponding to the sp-hybridized carbon is also observed, demonstrating a good structural matching between PFC and GDY. To give a further insight into the influence of GDY doping on spectral absorption of PFC, GDY film, PFC film, and GDY/PFC composite film were measured by the ultraviolet−visible (UV-vis) absorbance spectra, which is shown in Figure 4a. By contrast, in the range of 400-800 cm-1, GDY film does not show any feature absorption in the wavelength range. As for the PFC film and the GDY/PFC hybrid film, it can be seen that both the films show the similar absorption band with slight discrepancy, And the slope of PFC is higher than GDY/PFC around 700 nm, suggesting that the energy gap of GDY/PFC is smaller and this doping strategy could efficiently modify the energy gap of the carbonous organic polymers. In other words, doping GDY can


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improve energy level of pure PFC to realize better interfacial energy level matching, which could be favorable for the enhancement of carrier mobility and on/off ratio due to easier carrier transport between organic layer and Ag electrode.

Figure 3. Raman spectrums of GDY, PFC and GDY/PFC composite. In order to obtain the difference in the band gaps, we transformed the absorbance spectrum to the Kubelka−Munk spectrum, as shown in Figure 4b and 4c. The band gap Eg of the pure PFC film and GDY/PFC film are gained as 1.801 eV and 1.777 eV, respectively. Considering that the GDY was confirmed as a semiconductor with a band gap less than 1 eV,23, 24 thus the decreased Eg value of GDY/PFC film can be ascribed to the influence of narrow band gap as well as the accompanying energy level matching between PFC and GDY. To further evaluate the molecule energy levels of the PFC and GDY/PFC, cyclic voltammetry (CV) were used to measured their HOMO and LUMO. It is also found that the energy level of GDY/PFC is smaller than PFC,


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which is shown in Figure S2. The photon-generated carrier transport process under visible light irradiation is sketched in Figure 4d.

Figure 4. (a) UV−vis absorption spectra of GDY, PFC and GDY/PFC film. The Kubelka−Munk spectrum for (b) PFC and (c) GDY/PFC composite film respectively. (d) The GDY/PFC composite and its response visible light excitation. To investigate the role of GDY dopant in carrier transport characteristics of PFC, we measured the mobility of the polymer film by fabricating thin-film field effect transistor (FET) devices, as shown in Figure 5a-c. The typical transfer ISD-VG curves at VSD=1 V for PFC and GDY/PFC films are shown in Figure 5a. The threshold voltage absolute value of GDY/PFC film is about 0.5 V, which is much lower than that of the pure PFC (2.75 V), suggesting that


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GDY/PFC film based device can normally operate under low voltage. Besides, it is obvious that the output characteristic of PFC film is significantly improved by GDY doping. Especially the

Figure 5. (a) The transfer ISD-VG curves for PFC and GDY/PFC films. Transfer output FET characteristics obtained at zero bias and different VSD for (b) PFC and (c) GDY/PFC films. (d) The source-drain voltage dependent mobility of PFC and GDY/PFC films. (e) Structure of organic semiconductor/graphdiyne hybrid FET.


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on/off ratio of GDY/PFC film is much higher than that of pure PFC film, which means the device more stable, stronger anti-interference and larger load driving ability. The mobility can be calculated based on the equation of µ = 1

L ∂I D ,25 which is 0.69 cm2·V-1·s-1 and 0.002 cm2·VWCiVSD ∂VG

·s-1 for the composite film and the raw film respectively. It can be seen that the mobility is

increased by more than two orders of magnitude, indicating more superior carrier transport characteristics. Figure 5b and 5c present the output characteristics of the raw device and the composite device with different source-drain voltage. The voltage dependent mobility values can be calculated in Figure 5d and it seems that the mobility of GDY/PFC film is steadier compared with that of pure PFC film, demonstrating the application potential of organic polymer fieldeffect transistor modified by GDY doping. Here, the reasons of increased mobility can be attributed to three aspects, which are sketched in Figure 5e in detail. Firstly, the randomly distributed GDY flakes can be regarded as “fast lanes” for charge transport within the conduction channel26 since the calculated hole/electron mobility of GDY is comparable with graphene, which reduces the conducting channel length effectively and thus improve the output sourcedrain current. Secondly, for the interactive band diagram of Ag/GDY/PFC/Ag, application of the voltage bias may result in carrier movement from PFC matrix to GDY via intramolecular charge transfer interactions, which result in enhanced conductivity of the composite.27 Besides, it has been also reported that the acetylene linkages within the donor components of polymer are more electron-withdrawing than vinylene or ethane linkages,28 thus the introduction of acetylene linkages in our composite by doping with GDY also contributes to the change of carrier mobility. Meanwhile, the FET was measured in different electrode locations, sizes and concentrations, as shown in Figure S3 and S4. The result indicated that the different measuring locations and sizes didn’t change the slope of transfer curve obviously, as shown in Figure S3. Besides, the


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concentration dependent mobility shown in Figure S4 indicates that the carrier transport properties are closely related with the doping content and the ratio of 10% adopted in our manuscript is more beneficial to increase the device performance. Furthermore, we also employed electronic impedance spectroscopy (EIS) from 7 MHz to 100 MHz to obtain the carrier relaxation characteristics. Figure 6 presents the Nyquist plots at zero bias voltage for the pure PFC and GDY/PFC films, respectively. Carrier lifetime can be obtained from the angle frequency of characteristic peak fp and calculated as τ=1/2πfp,29, 30 which is 4.94 and 7.25 us for the pure PFC and GDY/PFC films, respectively. Combined with the 1/2

mobility value, we can further obtain the carrier diffusion length LD by LD = (kBT µτ r e) , where kB, T, and τr are Boltzmann constant, temperature, and carrier lifetime respectively.31, 32 The calculated LD for pure PFC and GDY/PFC film are 0.16 and 3.6 µm respectively, indicating that GDY/PFC composite can efficiently improve carrier transport properties and suppress the

Figure 6. Nyquist plots for the PFC film and GDY/PFC hybrid film at zero bias. potential recombination process. All the carrier transport characteristics for the pure PFC and GDY/PFC are summarized in Table 1, and we can see that the improvement of carrier diffusion mainly comes from the change of mobility, revealing the important role of charge transfer in


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carrier transport for this kind of polymer with D-A systems. These results not only help us further understand the regulatory mechanism in GDY/PFC hybrid film with post-processing technology but also promote the potential application of GDY-modified PFC in electron device or photoelectric device. Table 1. Carrier transport properties of PFC and GDY: PFC composite. Device

Eg (eV)

VT (V)

µ (cm2/V·s)

τ (µs)

LD (µm)

PFC

1.801

2.75

0.002

4.94

0.16

GDY/PFC

1.777

0.50

0.69

7.25

3.60

4. Conclusion In conclusion, we investigated the carrier transport properties of hybrid GDY/PFC film and found that the mobility could be dramatically increased to above two orders of magnitude as compared with the pure PFC film. Meanwhile, the threshold voltage and on/off radio of GDY/PFC film are also significantly improved compared with the pure PFC polymer film by GDY doping. The enhanced carrier transport properties can be attributed to the interfacial energy level matching and improved charge migration channel. We conclude that the introduction of GDY into organic polymer semiconductor will become a simple and effective strategy for improving OFET device performances as well as expanding the potential applications of PFC. Associated Content Supporting Information The following files are available free of charge. Author information Corresponding Author *E-mail: [email protected];


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*E-mail: [email protected]; *E-mail: [email protected]; *E-mail:[email protected]; Notes The authors declare no competing financial interest. Acknowledge This study was supported by the National Natural Science Foundation of China (21790050, 21790051, 21771187, 51673103 and 51373082), the Hundred Talents Program and Frontier Science Research Project (QYZDB-SSW-JSC052) of the Chinese Academy of Sciences, and the Natural Science Foundation of Shandong Province (China) for Distinguished Young Scholars (JQ201610). the Taishan Scholars Program of Shandong Province, China (ts20120528), the Key Research and Development Plan of Shandong Province, China (2016GGX102011). References (1). You, J. B.; Dou, L. T.; Yoshimura, K.; Kato, T.; Ohya, K.; Moriarty, T.; Emery, K.; Chen, C. C.; Gao, J.; Li, G.; et al. Polymer Tandem Solar Cell with 10.6% Power Conversion Efficiency. Nat. Commun. 2013, 4, 1446. (2). Liang, Y. R.; Xu, Z.; Xia, J. B.; Tsai, S. T.; Wu, Y.; Li, G.; Ray, C.; Yu, L. P. For the Bright Future-Bulk Heterojunction Polymer Solar Cells with Power Conversion Efficiency of 7.4%. Adv. Mater. 2010, 22, E135-138. (3). Wang, C.; Dong, H. L.; Hu, W. P.; Liu, Y. Q.; Zhu, D. B. Semiconducting π-Conjugated Systems in Field-Effect Transistors: A Material Odyssey of Organic Electronics. Chem. Rev. 2012, 112, 2208-2267.


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