Polymer-Assisted Single Crystal Engineering of Organic

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Organic Electronic Devices

Polymer-Assisted Single Crystal Engineering of Organic Semiconductor to Alter Its Electron Transport Haixiao Xu, Yecheng Zhou, Jing Zhang, Jianqun Jin, Guangfeng Liu, Yongxin Li, Rakesh Ganguly, Li Huang, Wei Xu, Daoben Zhu, Wei Huang, and Qichun Zhang ACS Appl. Mater. Interfaces, Just Accepted Manuscript • Publication Date (Web): 26 Mar 2018 Downloaded from http://pubs.acs.org on March 26, 2018

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ACS Applied Materials & Interfaces

Polymer-Assisted Single Crystal Engineering of Organic Semiconductor to Alter Its Electron Transport Haixiao Xu,†,▽ Yecheng Zhou,‖,▽ Jing Zhang,*,† Jianqun Jin,† Guangfeng Liu,‡ Yongxin Li,§ Rakesh Ganguly,§ Li Huang,‖ Wei Xu,*,⊥ Daoben Zhu,*,⊥Wei Huang*,†,Δ and Qichun Zhang *,‡,§ †

Key Laboratory for Organic Electronics and Information Displays & Jiangsu Key Laboratory for Biosensors, Institute of Advanced Materials (IAM), Jiangsu National Synergetic Innovation Center for Advanced Materials, Nanjing University of Posts & Telecommunications, 9 Wenyuan Road, Nanjing 210023, China ‖

Department of Physics, Southern University of Science and Technology, Shenzhen 518055, China

‡

School of Materials Science and Engineering, Nanyang Technological University Singapore, Singapore 639798, Singapore §

Division of Chemistry and Biological Chemistry, School of Physical and Mathematical Sciences, Nanyang Technological University, 639798, Singapore, Singapore ⊥

Beijing National Laboratory for Molecular Sciences, Key Laboratory of Organic Solids, Institute of Chemistry, Chinese Academy of Sciences, Beijing 100190, China Δ

Shaanxi Institute of Flexible Electronics (SIFE), Northwestern Polytechnical University (NPU), 127 West Youyi Road, Xi'an 710072, Shaanxi, China ABSTRACT: A new crystal phase of naphthalenediimide derivative (α-DPNDI) has been prepared via a facial polymerassisted method. The stacking pattern of DPNDI can be tailored from the known one-dimensional (1D) ribbon (β phase) to a novel two-dimensional (2D) plate (α phase) through the assistant of polymers. We believe that the presence of polymers during crystal growth is likely to reduce direct π-π interactions and favor side-to-side C-H-π contacts. Furthermore, β phase architecture shows higher electron mobility than α phase in the single-crystal-based OFET. Theoretical calculations not only confirm that β-DPNDI has a better performance in electron transport than α phase, but also indicate that α phase crystal displays a 2D transport while β phase possesses a 1D transport. Our results clearly suggest that polymerassisted crystal engineering should be a promising approach to alter the electronic properties of organic semiconductors. KEYWORDS: organic semiconductors, polymer assistant, phase transfer, n-type, two-dimensional

structures, in which defect-free and dense molecular ■ INTRODUCTION packing can enable high charge-carrier mobility.13,14 The development of novel highly-ordered crystalline Especially by changing the polarities/types of solvents 15 forms of organic functional materials, especially facial or using different concentrations of materials,16 different approach to new crystal phases,1-4 has drawn crystal polymorphism can be occasionally realized. substantial attentions in the field of material science and Recently, external-force methods have been employed to technology for many years.5-7 Such an approach is tune the molecule stacking. For example, solution particularly true for organic semiconductors including shearing can decrease π–π stacking distance of 6,13small molecules and polymers.8,9 Various fascinating bis(triisopropylsilylethynyl)pentacene molecular pair organic π-conjugated materials with different stacking from 3.33Å to 3.08Å via introducing lattice strain, and the geometries have been realized through adjusting mobility can be increased to as high as 4.6 cm2 V-1 s-1.17 10,11 substitutions as well as the control of growth Thus, in order to further increase the performance of conditions.12 Although subtle changes on molecular single component in solid-state devices, developing novel structure can lead to significant changes in crystal methods to change its crystal polymorph and packing modes, which can tune its physical properties, lattice constant is necessary. tedious synthesis efforts are required. Thus, changing the It is well-known that intermolecular interaction is one of stacking modes of one molecule in solid state without any the main nonbonding forces that affect the self-assembly additional synthetic modification is highly desirable. In and self-organization of organic molecules, which is a fact, many technologies have been developed as efficient key energy for the construction of single crystals and methods for the assembly of highly-ordered crystalline ACS Paragon Plus Environment

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crystalline nanostructures (nanocrystal or thin films).18 Normally, organic conjugated molecules can interact with neighboring ones and stack together into regular shapes,19,20 while sometimes the solvent molecules can insert into the framework to stabilize the resulting structure through side interactions.21 Recently, supramolecular donor-acceptor complexes constructed by the intermolecular interactions of both distinct and identic molecules exhibit unique superior charge transport property,22 metallicity,23 photoconductivity,24 ferroelectricity,25 or emission.26 Besides, polymer-matrixmediated molecular self-assembly approach can enhance the crystalline structural orders of polymer semiconductors and promote their charge transport mobility.27 Coupled crystallization of poly(3-hexyl thiophene) (P3HT) and perylene tetracarboxydiimide (PDI), tailored by the variation of P3HT/PDI ratio, solvent quality, and the PDI alkyl substituents, can generate donor/acceptor “shish-kebabs” with tunable nanostructures.28 Aligned films of nanocrystalline “shish-kebabs” of P3HT could be used to fabricate complementary logic gates.29 Combining the usage of ultrasound and soluble additive (polymer), P3HT was preferentially adsorbed on lateral crystal faces, yielding narrow width distributions.30 Thus, we believe that polymer-assisted single crystal engineering would help to alter charge transport property. Herein, we report that diphenyl-naphthalenediimide compound (DPNDI, scheme 1) can be induced to a new two-dimensional crystal polymorph (α phase) through the assisstant of one polymer (P3HT). Its electron transport characteristic has been compared with the known onedimensional stacking mode (β phase)31 without the polymer additive. We believe that our polymer-assistant strategy could provide researchers a novel route to construct new crystal polymorphs with varied electrical/optical properties. Scheme 1. Chemical structure of DPNDI.

Naphthalenediimide derivatives are typical π-conjugated aromatic planar semiconductors, which have been demonstrated to display n-type transport properties in solution-based thin films or microcrystals. Among these materials, the diphenyl-substituted one (DPNDI) is a moderate electron acceptor with good crystallinity and self-assembling ability. On the other hand, regioregular poly(3-hexylthiophene) (P3HT) is a well-studied organic electron acceptor as p-type semiconductor,32 especially in organic photovoltaic cells.33 Due to the long chains of polymers and good crystallinity of DPNDI, a region confinement or interaction is expected to form when these two molecules are mixed in the same solution. In this research, we demonstrated that DPNDI can form α and β phases from the solution with/out P3HT addition.

The as-prepared crystals have been employed as active elements in single-crystal-based organic field-effect transistors (OFETs) to understand how the structure affect the charge-transport characteristics. Such factors are futrther studied through theoretical calculations.

■ RESULTS AND DISCUSSION α- and β-DPNDI Crystals. P3HT and DPNDI (~1:1 ratio, total 2mg/ml) were mixed in capped glass bottles containing chlorobenzene (the solubility of P3HT is as high as several tens of miligrams per milliliter while DPNDI can reach one miligram per milliliter under heating treatment). After ultrasonicating the mixture for one hour at room temperature, the bottle was heated on a hot plate overnight to completely dissolve all compounds. Then, the as-resulted solution was naturally cooled to room temperature and highly-qualitied plate-like crystals (α phase, Figure 1a) were observed at the bottom of the bottle, while ribbon-like crystals (β phase crystal, Figure 1b) were formed through cooling pure DPNDI solution (1 mg ml-1) without adding any polymers.

Figure 1. Optical images of DPNDI. α phase crystals from polymer mixture solution (a) and β phase crystals from chlorobenzene (b). Both crystals, obtained through slow cooling of oversaturated solutions, were characterized by single-crystal X-ray diffraction. The crystallographic data of two crystal polymorphs were summarized in Table S1. The α crystal phase possesses an orthorhombic unit cell and belongs to Pbca space group with the unit cell parameters of a = 8.5676(6) Å, b = 7.0454(4) o Å, c = 30.713(2) Å, and α = β = γ = 90 . In α phase, the DPNDI molecules have a herringbone-stacking pattern with the dihedral angle of ~49.53°. In order to further minimize πorbital repulsion, all molecules adopt an edge-to-face arrangement to form a two-dimensional layer (plane ab). Clearly, such arrangement could further reduce the onedimensional face-to-face π-π interactions between adjacent molecules (Figure 2a). Along the π-π stacking direction, the slipping angle between adjacent molecules is about 25° (Figure S1), indicating a significant poor molecular overlapping and inefficient charge-transport ability. The β phase has a monoclinic unit (P21/n) with the unit cell parameters of a = 5.1563(2) Å, b = 7.4606(3) Å, c = 25.0305(11) Å, α = 90, β = o 31 90.1545(15), γ = 90 , consistent with the previous report. It was evident that β phase adopted π-π-type stacking between the neighboring molecular planes with the shortest distance of ~ 3.392 Å. Since good orbital overlapping between the neighboring molecules enables strong electronic coupling, good charge transport in this phase was expected along a axis (π-π interaction direction). The obvious difference in the

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ACS Applied Materials & Interfaces arrangement between these two crystals lies in the intermolecular interactions, and we believe that during crystallization, polymer chains can impede the self-assembly of host small molecules into 1D structure through the π-π interactions while polymer chains may favor the edge-to-face C-H-π close contacts, leading to a high dimensionality (2D architecture). Obviously, these differences in molecular packing structures play an important role on their charge transport 34,35 pathways and mobilities.

Figure 2. Crystal packing of DPNDI. α phase (a, herringbone stacking pattern) and β phase (b, π–π stacking pattern). Crystalline Microstructure. To better understand the influence of polymers on crystal growth, the crystalline nanostructures of DPNDI were conducted. Two different crystal-phase nanostructures can be easily obtained by simply drop-casting chlorobenzene solutions with different concentration. The dilute chlorobenzene solution (0.1-0.2 mg –1 mL ) of P3HT/DPNDI mixture is drop-casted onto the surface of bare SiO2/Si substrate to produce the 2D nanoplates (α phase, Figure 3a) with more than 100 nm in height and dozens of micrometers in length and width. On the other hand, the ribbon-like crystalline nanostructures (β phase) of DPNDI were prepared through drop-casting a DPNDI chlo–1 robenzene solution (~0.4 mg mL ) onto the surface of bare SiO2/Si wafer (Figure 3b), where micro-ribbons have dozens to hundreds of nanometers in height, several micrometers in width, and hundreds of micrometers in length. To further confirm the formation of both two types of nanostructures, we sequentially characterized the phase of the DPNDI-based nanostructures by using powder X-ray diffraction (XRD) analysis (Figure 3c and d). Both nanoplates and ribbons exhibited sharp Bragg reflections, which could be indexed into the corresponding crystal phases based on the as-obtained single-crystal data. It is worth noting that a weak peak at ~5.4° in pXRD pattern belongs to the polymer reflection. These results clearly suggest that polymer can endow small molecules with a new phase during the crystal growth in the polymer-containing parent solution. For the nanoplates (α phase), the XRD pattern showed the intense peaks at 5.8°, 11.6°, and 16.3°, which could be indexed as (002), (004), and (111), respectively. The strong peak at 5.8° corresponds to a d-spacing of 1.53 nm, was consistent with half of the c axis, suggesting that the crystals grew within the ab plane parallel to the substrate. In the case of nanoribbon morphology (β phase), the strong peak at 6.9° was indexed as

(00-2), indicating the crystal growth along the ab plane, parallel to the substrate. We found that the as-resulting blend microstructures of polymer/DPNDI after drop-casting the solution with different mixture ratios onto the surface had a significant morphology change. Even in these blends, with the polymer (90%) as the main part, a small sharp peak of 5.8° (α crystal) still could be observed (Figure S2). Increasing –1 the total concentration to 0.4-0.8 mg mL , 1D β phase nanoribbons coexisted on the substrate with 2D nanoplates (α phase, Figure S3), indicating that substantial DPNDI molecules prefer the stronger π-π stacking mode. As reported, crystallization additives (here polymer P3HT) might be strongly adsorbed onto the surface of the as-growing crystals and the curvature of the crystal gives rise to a larger surface area, resulting in the increased specific edge energy, interfa36 cial tension, and nucleation barrier. With the concentration of additives raised to a certain level, the 1D crystal growth would be halted (the inhibition of 1D orientation). If no polymer chains were encaged in the lattice architecture, the polymer additives were mainly adsorbed onto the crystal surface (superior and inferior sides), and small molecules were forced to grow along the lateral two-dimensional direc37 tions around the adsorbed polymer. Because the polymer in this research diffused faster to the outer surface of the crystal seeds comparing to the rate of crystal growth, we believe that the 2D growth under our condition didn’t receive too much disturbing. All these factors lead to the unreported new phase (α–DPNDI), as shown in Figure 3e. This result suggests that the usage of polymer could be a new strategy to generate new phases of organic conjugated small molecules.

Figure 3. (a and b) Optical micrographs and (c and d) XRD patterns of the microcrystals of self-assembled DPNDI with (a and c) α phase and (b and d) β phase. In (c) and (d), the peaks are indexed with lattice constant of the respective bulk crystal. (e) Illustration of the polymer assistant for new crystal phase growth.

Device Fabrication and Characterization. To investigate how different phases affect the charge transport property, we constructed the microcrystal-



based transistors with the bottom-gate top-contact geometry (Figure 4a). Figure 4b shows the illustrations of nanoplate(α-phase)-based and nanoribbon(β-phase)based transistors, with channel lengths of ~20 μm. All the characterizations were conducted in air. Unfortunately, we could hardly eliminate the polymer chains around the new quadrilateral crystal, and the as-made device showed the heterojunction characteristics, with the electron and hole field-effect mobilities calculated from the transfer curves to be 0.01 cm2 V−1 s−1 (μh) and 0.005 cm2 V−1 s−1 (μe), respectively (Figure 4c). The output characteristics of the heterojunction transistors based on P3HT/DPNDI nanosheets (α phase) are presented in Figure S5. This indicates the existence of polymer film in the active layer, which can cause p-n junction mobility in the OFETs. In contrast, the β phase nanoribbon device exhibited only electron transport mobility up to 0.03 cm2 V−1 s−1, which was higher than the electron transport property of α phase plate. The different results of the as-made DPNDIbased devices confirm the possibility of the packing alteration of organic semiconductors through the assistant of macromolecules/polymers.

efficient electronic coupling in other planes is found. As the maximum coupling is about four times higher, the charge transfer rate and the possibility along the direction of 11-15-19 should be sixteen times higher than other directions according to the Marcus formula. This means that the two-dimensional transport in β-crystals is more likely to be one-dimensional. Finally, we also calculated their mobility (α and β phase crystals) based on Marcus theory and kinetic Monte Carlo simulations,39 and the calculated electron mobility in β-DPNDI (2.59 cm2 V−1 s−1) was higher than that of α–DPNDI (1.16 cm2 V−1 s−1), as we supposed.

Figure 5. Illustration of the charge-transport pathways for electrons in α phase and β phase crystals. a) ab plane and b) bc plane of α phase crystal; c) ab plane and d) bc plane of β phase crystal. The center molecule is 15.

Figure 4. (a) Schematic diagram of a typical device structure. (b) Optical image of the device with the microcrystals of selfassembled DPNDI α phase and β phase, and their transfer characteristics of the device. (c) α Phase nanoplate hybrid (Vds = ± 60 V). (d) β Phase nanoribbon (Vds = 30V).

To further understand how the molecular packings affect their electronic properties,38 we also inspected the electronic coupling and electron mobility theoretically. The electronic couplings were calculated under the level of B3LYP/ 6-311G**, which was implemented in Gaussian 09. The corresponding electronic couplings are shown in Table S2. Figures 5a-d showed the charge-transport pathways for electrons in ab and bc planes of α and β phase crystals. One can find that the electronic coupling along the molecule chain of 11-15-19 is about two times higher than that in other directions in ab plane. Dimers in the other plane exhibit very small couplings (less than 1 meV). Hence, the charge transfer in α-phase crystals should be two-dimensional. It was also shown that the maximum coupling in β-phase crystals was along the molecule chain of 11-15-19, which is about three to four times higher than that in other directions in ab plane. No

■ CONCLUSIONS In conclusion, we reported a novel, fast and efficient method (polymer-assistant growth) to prepare a new DPNDI crystal phase. Particularly, we found that the polymer chains can reduce direct π-π interactions and promote side-to-side molecular interactions, resulting in both 2D packing mode and novel transport pathway. Through device fabrication, we successfully characterized the charge-transport properties of both phases in the nanocrystals, and found that nanoribbon structures (β phase) possessed higher mobility. Theoretical calculation revealed that one-dimensional transport existed in the 1D aligning mode structure while two-dimensional electron transport in α phase due to the formation of 2D herringbone stack crystals. The polymer-assistant crystal growth method could be developed as a novel efficient way to obtain new crystal architectures and provide new applications in organic semiconductor devices. ■ EXPERIMENTAL SECTION Materials. Regioregular poly(3-hexylthiophene) was bought from Luminescence Technology Corp. with details of Mw > 45,000 (GPC), electronic grade and > 93% head-


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ACS Applied Materials & Interfaces to-tail regioregular. Chlorobenzene (HPLC) was purchased from Sigma-Aldrich. DPNDI was purchased from Solarmer Materials Company and used as received. The solvents were used without further purification. Preparation of α and β phase crystals. The DPNDI crystals were prepared using slow cooling of saturated solutions from high temperature method. Two types of chlorobenzene solutions of DPNDI or DPNDI/P3HT were heated at high temperature for complete dissolution. Then, the resulted oversaturated solutions were naturely cooled down under ambient conditions. Quantities of ribbon-shape or plate-shape crystals were observed on the bottom of the bottle after one or two days. Growth of the micro-crystals and device fabrication. The SiO2/Si substrate was heavily-doped n-type Si wafer with a 500 nm thick SiO2 layer and a capacitance of 7.5 nF·cm-2. Bare substrates were successively cleaned with pure water, piranha solution (H2SO4:H2O2 = 2:1), pure water, and pure isopropanol. Micro/nanostructure single crystals of the DPNDI were conducted by using the dropcasting method. A chlorobenzene solution containing DPNDI or DPNDI/P3HT hybrid (0.1~0.2 mg ml-1, mass ratio 1:1) was poured over the substrates and the solvent evaporated at room temperature. Drain and source Au electrodes (~40 nm thick) were deposited on the crystal by thermal evaporation with a copper grid as the shadow mask. Measurements. X-ray diffraction (XRD) was measured on D/max2500 with CuKa source (κ = 1.541 Å). I–V characteristics of the OFETs were recorded with a Keithley 4200 SCS and a Micromanipulator 6150 probe station in a clean and shielded box at room temperature. X-ray crystallographic data were collected with a Bruker Smart-1000-CCD diffractometer, using graphitemonochromated Mo Kα radiation (λ = 0.71073 Å). The data were collected at 100 K and the structure was resolved by the direct method and refined by the fullmatrix least-squares method on F2. Theoretical calculation details. All the calculations were performed with G09 at level of B3LYP/6-311G**. Charge transfer rate was calculated by Marcus theory:

■ ASSOCIATED CONTENT Supporting Information. The Supporting Information is available free of charge on the

ACS Publications website at http://pubs.acs.org. Experimental methods and instruments, The slipping angle, Optical micrographs and XRD patterns of the nanostructures, Output characteristics, Crystallographic data and Electronic coupling data Crystallographic data of α–DPNDI (CIF)

■ AUTHOR INFORMATION Corresponding Author * [email protected]

* [email protected] * [email protected] * [email protected] * [email protected]

Author Contributions ▽

These authors contributed equally.

Notes The authors declare no competing financial interest.

■ ACKNOWLEDGMENT Q. Z. acknowledges the financial support from AcRF Tier 1 (RG 111/17, TRG2/17, RG8/16 and RG114/16). J. Z. acknowledges the financial support from the National Natural Science Foundation of China (21602113 and 61774087).

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Polymer-Assisted Single Crystal Engineering of Organic

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