A Dewetting-Induced Assembly Strategy for Precisely Patterning

Subscriber access provided by UNIV LAVAL

Article

A Dewetting Induced Assembly Strategy for Precisely Patterning Organic Single Crystals in OFETs Xiao-Nan Kan, Chengyi Xiao, Xinmeng Li, Bin Su, Yuchen Wu, Wei Jiang, Zhaohui Wang, and Lei Jiang ACS Appl. Mater. Interfaces, Just Accepted Manuscript • DOI: 10.1021/acsami.6b04163 • Publication Date (Web): 05 Jul 2016 Downloaded from http://pubs.acs.org on July 11, 2016

Just Accepted “Just Accepted” manuscripts have been peer-reviewed and accepted for publication. They are posted online prior to technical editing, formatting for publication and author proofing. The American Chemical Society provides “Just Accepted” as a free service to the research community to expedite the dissemination of scientific material as soon as possible after acceptance. “Just Accepted” manuscripts appear in full in PDF format accompanied by an HTML abstract. “Just Accepted” manuscripts have been fully peer reviewed, but should not be considered the official version of record. They are accessible to all readers and citable by the Digital Object Identifier (DOI®). “Just Accepted” is an optional service offered to authors. Therefore, the “Just Accepted” Web site may not include all articles that will be published in the journal. After a manuscript is technically edited and formatted, it will be removed from the “Just Accepted” Web site and published as an ASAP article. Note that technical editing may introduce minor changes to the manuscript text and/or graphics which could affect content, and all legal disclaimers and ethical guidelines that apply to the journal pertain. ACS cannot be held responsible for errors or consequences arising from the use of information contained in these “Just Accepted” manuscripts.

ACS Applied Materials & Interfaces is published by the American Chemical Society. 1155 Sixteenth Street N.W., Washington, DC 20036 Published by American Chemical Society. Copyright © American Chemical Society. However, no copyright claim is made to original U.S. Government works, or works produced by employees of any Commonwealth realm Crown government in the course of their duties.

Page 1 of 25

1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 18 19 20 21 22 23 24 25 26 27 28 29 30 31 32 33 34 35 36 37 38 39 40 41 42 43 44 45 46 47 48 49 50 51 52 53 54 55 56 57 58 59 60

ACS Applied Materials & Interfaces

A Dewetting Induced Assembly Strategy for Precisely Patterning Organic Single Crystals in OFETs Xiaonan Kan †, Chengyi Xiao†, Xinmeng Li†, Bin Su§, Yuchen Wu†, Wei Jiang*†, Zhaohui Wang*†, Lei Jiang‡ †Beijing National Laboratory for Molecular Sciences (BNLMS),Key Laboratory of Organic Solids and Laboratory of New Materials Institute of Chemistry, Chinese Academy of Sciences (ICCAS), Beijing, 100190 (P. R. China) E-mail: [email protected]; [email protected] ‡Laboratory of Bio-inspired Smart Interface Science, Technical Institute of Physics and Chemistry, Chinese Academy of Sciences, Beijing, 100190 (P. R. China) §Department of Chemical Engineering, Monash University, Clayton, Victoria 3800, Australia

KEYWORDS: Liquid bridge, Single crystal, Assembly, Micropillars, Field-effect transistors

ACS Paragon Plus Environment

1


1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 18 19 20 21 22 23 24 25 26 27 28 29 30 31 32 33 34 35 36 37 38 39 40 41 42 43 44 45 46 47 48 49 50 51 52 53 54 55 56 57 58 59 60

Page 2 of 25

ABSTRACT: Simple ways to pattern single crystals are critical to fully realize their applications in electronics. However, traditional vapor or solution methods are deficient in terms of crystals with random spatial and quality distributions. Here, we report a dewetting induced assembly strategy in obtaining large scale and highly oriented organic crystal arrays. And we demonstrate organic field-effect transistors (OFETs) fabricated from patterned n-alkyl substituted tetrachloroperylene diimides (R-4ClPDIs) single crystals can reach a maximum mobility of 0.65 cm2 V-1 s-1 for C8-4ClPDI in ambient conditions. This technique constitutes a facile method for fabricating OFETs with high performances in large-scale electronics applications.


2

Page 3 of 25

1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 18 19 20 21 22 23 24 25 26 27 28 29 30 31 32 33 34 35 36 37 38 39 40 41 42 43 44 45 46 47 48 49 50 51 52 53 54 55 56 57 58 59 60


1. Introduction Semiconductive small molecular micro/nano crystals are of vital importance in electronic fields, especially in organic field effect transistors (OFETs).1-5 These structures have advantages over inorganic counterparts due to their unique properties such as flexibility, tenability of molecular structure and easy compatibility with solution based methods.1, 6-7 Among these, single crystal devices are more ideal8-9 to exploit the intrinsic charge transport properties compared with polycrystalline films, because they possess lower density of defects and fewer grain boundaries. However, single crystal devices obtained from conventional cultivation methods generally have problems in nonhomogenous structures and random distribution, which hindered their wide applications.10 Therefore, patterning single crystals is efficient in the following points: 1) better control the structure and distribution of the singe crystals; 2) conductive pathways between adjacent devices can be restrained by applying this strategy; 3) realize their practical applications in electronics.11 Various patterning techniques have been developed. Physical vapor transport (PVT),12 combining with microcontact printing13 or predepositing techniques

14

is effective. Solution

based techniques are ideally suitable for low cost fabrication, including transfer printing,15 antisolvent crystallization,7 solution shearing,1 combination of selective surface patterning,16 direct printing17 and so on. Although these approaches underscore the rapid process, open issues in exploiting practical application stimulated the development of patterning approaches. Recently, a new use of “dewetting induced assembly” strategy was demonstrated for assembling graphene,18

small

molecules,19

polymers,20

nanoparticles,21

biomarcromolecules22 and

microspheres.23 By employing pillar-structured surfaces and confined assembling induced by dewetting of one-dimensional liquid-bridges on the interface, this technology provides great


3


1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 18 19 20 21 22 23 24 25 26 27 28 29 30 31 32 33 34 35 36 37 38 39 40 41 42 43 44 45 46 47 48 49 50 51 52 53 54 55 56 57 58 59 60

Page 4 of 25

potential in patterning single crystal OFETs due to the easy fabrication, low cost and solution processibility. Perylene diimide (PDI) derivatives have gained extensive attention owing to their unique properties recently24-27 and applications in opto/electronic fields.28-31 High performance, n-type field-effect transistors based on air-stable perylene diimide (PDI) derivatives have been presented in our previous research.32 Here we demonstrate patterned OFETs fabricated from single crystal series of n-alkyl substituted tetrachloroperylene diimides (R-4ClPDIs) with highest mobility reaching 0.65 cm2 V-1 s-1 that could be operated in ambient environment. By using regular micropillars, patterned single crystals of R-4ClPDIs can grow into desirable position, demonstrating an innovative process which can be operated at room temperature for OFETs. In addition, the uniform structures of crystal arrays are perfect for researches of relevant charge transport properties. 2. Experimental Section Device fabrication: Strip structure silicon pillar template was prepared according to previous study.18 And the pillar-structured template was changed from spindle to groove in this experiment. The parameters were as follows: The width was 2-5 µm, the distance between neibouring pillar was 2 µm and the height was 15 µm. Three kinds of molecules, C4-4ClPDI, C8-4ClPDI, C12-4ClPDI was synthesized and purified according to literature.33-34 Then, all the samples were dissolved in trichloromethane (Sigma-Aldrich Co., Ltd) to make solution. Top-contact devices of the patterned micro/nanocrystal arrays were fabricated directly on Si/SiO2 (300 nm) substrates which were treated by octadecyltrichlorosilane (OTS) and by employing gold stripes as source and drain (S-D) electrodes which were “stamped” onto the substrates. The OFET devices were fabricated along


4

Page 5 of 25

1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 18 19 20 21 22 23 24 25 26 27 28 29 30 31 32 33 34 35 36 37 38 39 40 41 42 43 44 45 46 47 48 49 50 51 52 53 54 55 56 57 58 59 60


the longitudinal direction of the single crystals and were all measured under ambient conditions. A Keithley 4200 SCS semiconductor parameter analyzer was used to measure the characteristics of the devices at room temperature under ambient environment. The mobilities were calculated from the saturation region with the following equation:2

(

I DS = W

C µ (V 2L ) i

G

2

− VT ) ,

(1)

Characterization: An optical microscope (Vision Engineering Co., UK), coupled to a CCD camera, was used to obtain the microscope images of the crystal arrays of all the molecules. A Nanoscope IIIa instrument (Digital Instruments) was applied to the Atomic force microscopy (AFM) measurements. X-ray diffraction (XRD) measurements was carried out on a D/max2500 with a CuKα source (κ = 1.541 Å). The detailed structure of the organic single crystals was taken on JEOL TEM-2100 (Accelerating voltage: 200 KV). CPOM images were taken using a crosspolarized optical microscope (LeicaDM 4000M) A dataphysics OCA20 contact-angle system was employed to measure the static contact angles in the air. When measuring samples, the CA was recorded at least five different positions to acquire the average value. Calculation: To gain further insight into the influnence of the solvents, Gromacs 4.0.535 software was applied to perform simulations of molecular dynamics35 under constant pressure and temperature condition. Two kinds of solvents, trichloromethane and toluene, were chosen in molecular dynamic simulations. The force field used was Gromos-54a7 and was further manipulated using Automated Topology Builder36 including the charge distribution refinement. The temperature and pressure of the system was 298K and 1atm realized by using the NoseHoover thermostat37 and Parrinello-Rahman barostat.38 In this system, long-range electrostatic interactions were processed by particle-mesh Ewald method.39 And for Lennard-Jones interactions, the cut-off radius was 1.2 nm. In every direction, the periodic boundary conditions


5


1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 18 19 20 21 22 23 24 25 26 27 28 29 30 31 32 33 34 35 36 37 38 39 40 41 42 43 44 45 46 47 48 49 50 51 52 53 54 55 56 57 58 59 60

Page 6 of 25

were the same. The structure of molecules were shown in VDW style and solvents were shown in line style in VMD40 software. 3. Results and discussion 3.1. Characterization of the as-prepared patterned microstrips A scheme of the assembly process is presented in Figure 1. The synthetic route for octyl substituted tetrachloroperylene diimide, C8-4ClPDI, was similar with previous study.26, 41-44 And trichloromethane (≥99%, Sigma-Aldrich) was chosen as excellent solvent for the molecules. The first step was adding solution onto the silicon template. A sandwich system was thus formed after placing the desired substrate onto the solution layer. Due to the lyophilic property of the silicon pillars to the solvents (see Supporting Information Figure S1), gradually, the solution can infiltrate into the spaces between silicon pillars. On the basis of previous studies, the anisotropic shrink of Triple-phase Contact Line (TCL) happens upon a structure-free substrate controlled by the Gibbs free energy minimization.45-46 In this system, the liquid layer ruptured owing to the combined effects of geometric influence and lyophilic property, in which the micropillars can serve as the "pinning" points to control this process. In the process of solvent evaporation, the liquid layer ruptured and the micro-sized silicon pillar arrays can serve as wetting supports to control this process, micrometer-scaled liquid bridges can be thus yielded in a continuous way. Organic molecules will assemble in the shrinking confined spaces provided by these liquid bridges and finally the patterned structures were formed under control.


6

Page 7 of 25

1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 18 19 20 21 22 23 24 25 26 27 28 29 30 31 32 33 34 35 36 37 38 39 40 41 42 43 44 45 46 47 48 49 50 51 52 53 54 55 56 57 58 59 60


Figure 1. Sandwich method for fabricating of large scale C8-4ClPDI crystal microstripes. (a) Schematic diagram of the process. Step 1: The sample solution is first dropped onto the stripe structure silicon pillar template. Step 2: A flat substrate is put on the top, forming a sandwich system. Step 3: Subsequent solvent evaporation and formation of patterned crystals induced by liquid bridges. Step 4: The template is then taken away. (b) Microscope image of the obtained C8-4ClPDI crystal microstripes. (c) XRD data of the patterned single crystals. (d) CPOM images of obtained patterned C8-4ClPDI crystals.

Microscope image of the obtained organic crystal arrays is presented in Figure 1b, with an area of about 50 × 50 µm2. The crystal quality was assessed by a number of analytical techniques. Results from atomic force microscope (AFM) images show, the width of the microstrips is about 2.0 µm with a height of 68 nm (see Supporting Information Figure S5). As can be seen from the AFM results, the obtained C8-4ClPDI stripe was intact crystal with smooth and uniform texture. In addition, as shown in X-ray diffraction (XRD) results (Figure 1c), the molecules packed along well defined (100) lattice plane, indicating the long-range ordering, and the


7


1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 18 19 20 21 22 23 24 25 26 27 28 29 30 31 32 33 34 35 36 37 38 39 40 41 42 43 44 45 46 47 48 49 50 51 52 53 54 55 56 57 58 59 60

Page 8 of 25

calculated d-spacing is 20.5 Å, comparable to the value of single crystals obtained from physical vapor transport (PVT) method.27 Moreover, the cross polarized optical microscope (CPOM) is an effective tool for determination of crystal orientation.47 As can be seen from CPOM images in Figure 1d, well aligned crystal structure was demonstrated. In the left, the patterned crystals extinguishes polarized light, but when the substrate is rotated ≈ 45° a maxima in intensity occurred. The change in crystal intensities indicated the well aligned nature of the patterned crystals.48 In addition, The TEM image of one single microstripe of C8-4ClPDI crystal arrays reveals that the patterned microstripes exhibit a very neat morphology and bright and welldefined diffraction spots were shown at different positions of the single microstripe in the corresponding selected area electron diffraction (SAED) patterns (see Supporting Information Figure S2).27 These results give further support to the conclusion that the crystals prepared from our method exhibit high quality single crystalline nature. 3.2. Field effect transistors based on the patterned arrays OFETs employing bottom-gate top-contact device configuration were fabricated by “stamping” gold stripes on the microstripes. and OTS-treated SiO2 (300 nm) dielectric layers (Figure 2a). Typical output (Figure 2b) and transfer curves (Figure 2c) were measured in atmosphere. For these devices, a maximum mobility of 0.65 cm2 V-1 s-1 can be reached in the saturation regime of VG = 40 V with Ion/off ≈ 105, a threshold voltage of 16 V, when the channel width was 1.80 µm, and the channel length was 17.8 µm. The average mobility was 0.30-1.00 cm2 V-1 s-1 tested from 29 devices. For comparison, C8-4ClPDI thin film transistors have shown poor performances, the magnitude of the mobility was 10-5 cm2 V-1 s-1 due to the poor crystallinity of the films,49 which has the same magnitude as our measured film results. Moreover, traditional drop-cast method and physical vapor transport method27 can be used to


8

Page 9 of 25

1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 18 19 20 21 22 23 24 25 26 27 28 29 30 31 32 33 34 35 36 37 38 39 40 41 42 43 44 45 46 47 48 49 50 51 52 53 54 55 56 57 58 59 60


prepare single crystals, the electron mobilities can reach 0.30 cm2 V-1 s-1 (see Supporting Information Figure S3) and 0.80 cm2 V-1 s-1, respectively. For devices fabricated from C8F4ClPDI crystals, realized by physical vapor transport method, the electron mobility can reach 1.43 cm2 V-1 s-1.27 Besides, C12-4CldiPBI single crystals can be obtained from solution-based methods. The thus fabricated OFETs can realize a high electron mobility of 4.65 cm2 V-1 s-1.26 In addition, single-crystal FETs based on PDIF-CN2 fabricated by physical vapor transport method can reach mobilities range between ∼3 and 0.8 cm2 V-1 s-1 in ambient conditions.24 But these conventional methods were time-consuming and the crystals distributed on the substrate randomly. The results from our studies show that by using the sandwich system, we can obtain patterned OFETs with uniform mobility in a facile way.


9


1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 18 19 20 21 22 23 24 25 26 27 28 29 30 31 32 33 34 35 36 37 38 39 40 41 42 43 44 45 46 47 48 49 50 51 52 53 54 55 56 57 58 59 60

Page 10 of 25

Figure 2. Representative electrical characteristics for C8-4ClPDI patterned crystal based transistors. (a) Structural diagram of the devices. (b) Output and (c) transfer curves. (d) The device mobility and voltage (VT) remains relatively the same with increment of channel length.

3.3. Investigation of the influence factors on the performance of the OFETs 3.3.1. Concentration and channel length Sample concentration typically have important influence on the morphology of the crystal arrays, thus may affect the performance of the devices. In this experiment, thickness of the microstrips changed from 47 nm to 80 nm as the sample concentration increased from 0.5, 0.8, 1.0, 1.5 to 2.0 mg/mL (see Supporting Information Figure S4). The mobility was 0.27, 0.44, 0.65, 0.11, 0.07 cm2 V-1 s-1, correspondingly. We attributed this phenomenon to both mobility induced from layers at the bottom and the current flow in the top layers. When the thickness of the samples was below 68 nm, impurities at the interface may have greater influence on the crystals, thus the mobilities were low. As the samples become thicker, in the top layers, the current were forced to flow due to the finite interlayer resistance, which were out of control of the backgate. Consequently, for samples thicker than 68 nm, the mobilities will decline.50 As for the impact of channel length, the voltage and mobility increased slightly as the channel length changed from several micrometers to about twenty micrometers. And the value remained relatively the same when further increased the channel length, Figure 2d. This can be ascribed to the homogeneity of the crystals fabricated from our method, demonstrating the effectiveness of this liquid-bridge induced strategy in OFETs.


10

Page 11 of 25

1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 18 19 20 21 22 23 24 25 26 27 28 29 30 31 32 33 34 35 36 37 38 39 40 41 42 43 44 45 46 47 48 49 50 51 52 53 54 55 56 57 58 59 60


Figure 3. Further insight into the device performance by varying side chain length and solution concentration. (a) Chemical structure of R-4ClPDIs with different substituents. R1 = butyl (abbreviated C4), R2 = octyl (abbreviated C8), R3 = dodecyl (abbreviated C12). (b-d) Microphotograph of C4, C8, C12-4ClPDI crystal arrays. (e-g) corresponding transfer characteristics of OFETs based on C4, C8, C12-4ClPDI crystals arrays. (h) Three dimensional diagram of influence of sample concentration on both the crystal thickness and thus fabricated transistors.

3.3.2. Side chain substituents The impact of side chain substituents was also investigated here. Butyl and dodecyl substituted derivatives, C4-4ClPDI and C12-4ClPDI were synthesized. Under same experimental conditions, large scale patterned crystals can also be fabricated (about 50 × 50 µm2), shown in Figure 3b and 3d. Results from AFM show that C4-4ClPDI and C12-4ClPDI just formed layered micro/nano crystals (see Supporting Information Figure S5). The maximum mobility of devices based on C4-4ClPDI and C12-4ClPDI crystal arrays was 0.24 cm2 V-1 s-1 and 0.05 cm2 V-1 s-1, respectively. For comparison, the maximum mobility of thin film C4-4ClPDI and


11


1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 18 19 20 21 22 23 24 25 26 27 28 29 30 31 32 33 34 35 36 37 38 39 40 41 42 43 44 45 46 47 48 49 50 51 52 53 54 55 56 57 58 59 60

Page 12 of 25

C12-4ClPDI was 1.3 × 10-3 cm2 V-1 s-1 and 5 × 10-3 cm2 V-1 s-1 (see Supporting Information Figure S6), both after annealing at 200 ºC (Td) for 90 min in vacuum, indicating that much better device performances and easier process could be achieved based on our method. The crystal structures will become more ordered when the length of the alkyl chains was increased, thus the device mobilities will be enhanced.51 However, when the length of the side alkyl chains was further increased, the decrease in crystallinity prevented the effective packing of PDI molecules in the solvent (see Supporting Information Figure S5). That is why C8-4ClPDI based FETs have shown the best performances. In addition, all devices based on patterned stripes of three kinds of R-4ClPDIs exhibit long term stability during 100 days (see Supporting Information Figure S8).


12

Page 13 of 25

1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 18 19 20 21 22 23 24 25 26 27 28 29 30 31 32 33 34 35 36 37 38 39 40 41 42 43 44 45 46 47 48 49 50 51 52 53 54 55 56 57 58 59 60


Table 1. Field effect characteristics of devices based on C4,C8,C12-4ClPDI crystal arrays and comparison with their thin film transistors Semiconductor

Td(ºC)

µmax (cm2•V-1•s-1)

T(min)

*

*

200

90

*

*

110

90

*

*

200

90

C4-4ClPDI

C8-4ClPDI

C12-4ClPDI

Crystal arrays Thin Film Crystal arrays Thin Film Crystal arrays Thin Film

Vth(V)

Ion/Ioff

0.24

12

105

0.0013

44

105

0.65

16

105

0.00005

96

102

0.05

16

104

0.005

14

105

3.3.3 Solvents Solvents typically played vital role in the performance of FETs. We changed solvents from trichloromethane to toluene to investigate the influence. As can be seen, crystals prepared from toluene solution had a less clear boundary than those obtained from trichloromethane with thickness reaching 52 nm and a maximum mobility of 0.22 cm2 V-1 s-1. Appropriate solvent condition will be beneficial for well "balanced” assembly process when forming crystals. We assumed that in toluene, due to the strong intermolecular interaction between the solvent and the molecule, the balance of the system was broken. We checked the proposal in a molecular dynamics test. As shown in Figure 4d, the PDI molecules tended to assembly in twisted structure in toluene, while those in trichloromethane forming a long range ordered structure (Figure 4e), which would be beneficial for the charge transport, thus leading to an enhancement of mobility.


13


1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 18 19 20 21 22 23 24 25 26 27 28 29 30 31 32 33 34 35 36 37 38 39 40 41 42 43 44 45 46 47 48 49 50 51 52 53 54 55 56 57 58 59 60

Page 14 of 25

Figure 4. Impact of solvents on crystal forming and device performance. (a) Molecular structures of two solvents used in our experiment, trichloromethane (left) and toluene (right). (b,c) Transfer characteristics of devices based on patterned crystals from trichloromethane (b) and toluene (c). (d,e) Molecular dynamics test results. The results indicated that the PDI molecules tended to assembly in long range ordered structure in trichloromethane (d), while those in toluene forming a twisted structure (e).

4. Conclusion In conclusion, a facile dewetting induced assembly strategy has been employed for precisely patterning organic single crystals for OFETs. Large scale crystal arrays based on R4ClPDIs can be fabricated with highly controlled orientation and alignments. The as-prepared


14

Page 15 of 25

1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 18 19 20 21 22 23 24 25 26 27 28 29 30 31 32 33 34 35 36 37 38 39 40 41 42 43 44 45 46 47 48 49 50 51 52 53 54 55 56 57 58 59 60


field effect transistors have shown much superior performances due to the high crystallinity and uniform mobility. Further improvement on sample concentration and processing solvents produced the maximum electron mobility reaching 0.65 cm2 V-1 s-1 for C8-4ClPDI in the air. We anticipate our work to bring new alternatives for low-cost techniques for fabricating patterned OFFTs with high performances and many other electronic devices under mild conditions.


15


1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 18 19 20 21 22 23 24 25 26 27 28 29 30 31 32 33 34 35 36 37 38 39 40 41 42 43 44 45 46 47 48 49 50 51 52 53 54 55 56 57 58 59 60

Page 16 of 25

ASSOCIATED CONTENT Supporting Information. Additional Figure S1-S8 is available free of charge via the Internet on the ACS publications website at http://pubs.acs.org. Figures of transmission electron microscope (TEM) and selected area electron diffraction (SAED) of the crystals prepared through our method. Brief introduction of single crystals fabricated from the conventional drop-casting method. Crystal morphologies and OFETs performances from various solution concentrations and different device performances based on three molecules. Table of detailed information of the length to width ratio of the TFT and the strength of the bias voltage of devices. Scheme of the measurement process. Atomic force microscope (AFM) images of crystals based on three molecules. Typical transfer curves of thin film transistors. Hysteresis curves and long term stability measurements of devices based on three molecules (PDF). AUTHOR INFORMATION Corresponding Author *Wei Jiang, Email: [email protected] *Zhaohui Wang, Email: [email protected] Author Contributions The manuscript was written through contributions of all authors. All authors have given approval to the final version of the manuscript. X. Kan and C. Xiao contributed equally to this work.


16

Page 17 of 25

1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 18 19 20 21 22 23 24 25 26 27 28 29 30 31 32 33 34 35 36 37 38 39 40 41 42 43 44 45 46 47 48 49 50 51 52 53 54 55 56 57 58 59 60


Notes The authors declare no competing financial interest. ACKNOWLEDGMENT The authors thank the National Research Fund for Fundamental Key Projects (2013CB933503), the National Natural Science Foundation (21225209, 21421061), and the Key Research Program of the Chinese Academy of Sciences (KJZD-EW-M01, KJZD-EW-M03, XDB12010000) and the 111 project (B14009) for financial support.


17


1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 18 19 20 21 22 23 24 25 26 27 28 29 30 31 32 33 34 35 36 37 38 39 40 41 42 43 44 45 46 47 48 49 50 51 52 53 54 55 56 57 58 59 60

Page 18 of 25

REFERENCES (1) Giri, G.; Verploegen, E.; Mannsfeld, S. C. B.; Atahan-Evrenk, S.; Kim, D. H.; Lee, S. Y.; Becerril, H. A.; Aspuru-Guzik, A.; Toney, M. F.; Bao, Z. N. Tuning Charge Transport in Solution-Sheared Organic Semiconductors using Lattice Strain. Nature 2011, 480, 504-508. (2) Gundlach, D. J.; Royer, J. E.; Park, S. K.; Subramanian, S.; Jurchescu, O. D.; Hamadani, B. H.; Moad, A. J.; Kline, R. J.; Teague, L. C.; Kirillov, O.; Richter, C. A.; Kushmerick, J. G.; Richter, L. J.; Parkin, S. R.; Jackson, T. N.; Anthony, J. E. Contact-Induced Crystallinity for High-performance Soluble Acene-Based Transistors and Circuits. Nat. Mater. 2008, 7, 216-221. (3) Lezama, I. G.; Nakano, M.; Minder, N. A.; Chen, Z. H.; Di Girolamo, F. V.; Facchetti, A.; Morpurgo, A. F. Single-crystal Organic Charge-Transfer Interfaces Probed Using SchottkyGated Heterostructures. Nat. Mater. 2012, 11, 788-794. (4) Najafov, H.; Lee, B.; Zhou, Q.; Feldman, L. C.; Podzorov, V. Observation of Long-range Exciton Diffusion in Highly Ordered Organic Semiconductors. Nat. Mater. 2010, 9, 938-943. (5) Sundar, V. C.; Zaumseil, J.; Podzorov, V.; Menard, E.; Willett, R. L.; Someya, T.; Gershenson, M. E.; Rogers, J. A. Elastomeric Transistor Stamps: Reversible Probing of Charge Transport in Organic Crystals. Science 2004, 303, 1644-1646. (6) Zhang, X.; Jie, J.; Deng, W.; Shang, Q.; Wang, J.; Wang, H.; Chen, X.; Zhang, X. Alignment and Patterning of Ordered Small-Molecule Organic Semiconductor Micro-/Nanocrystals for Device Applications. Adv. Mater. 2016, 6, 2475–2503. (7) Minemawari, H.; Yamada, T.; Matsui, H.; Tsutsumi, J.; Haas, S.; Chiba, R.; Kumai, R.; Hasegawa, T. Inkjet Printing of Single-Crystal Films. Nature 2011, 475, 364-367.


18

Page 19 of 25

1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 18 19 20 21 22 23 24 25 26 27 28 29 30 31 32 33 34 35 36 37 38 39 40 41 42 43 44 45 46 47 48 49 50 51 52 53 54 55 56 57 58 59 60


(8) De Boer, R. W. I.; Gershenson, M. E.; Morpurgo, A. F.; Podzorov, V. Organic Single-Crystal Field-Effect Transistors. Phys. Status Solidi A 2004, 201, 1302-1331. (9) Reese, C.; Bao, Z. N. Organic Single-Crystal Field-Effect Transistors. Mater. Today 2007, 10, 20-27. (10) Tang, Q.; Jiang, L.; Tong, Y.; Li, H.; Liu, Y.; Wang, Z.; Hu, W.; Liu, Y.; Zhu, D. Micrometer- and Nanometer-Sized Organic Single-Crystalline Transistors. Adv. Mater. 2008, 20, 2947-2951. (11) Chang, J.-F.; Sirringhaus, H. Patterning of Solution-Processed Semiconducting Polymers in High-Mobility Thin-Film Transistors by Physical Delamination. Adv. Mater. 2009, 21, 25302535. (12) Kloc, C.; Simpkins, P. G.; Siegrist, T.; Laudise, R. A. Physical Vapor Growth of Centimeter-Sized Crystals of Alpha-Hexathiophene. J. Cryst. Growth 1997, 182, 416-427. (13) Briseno, A. L.; Mannsfeld, S. C.; Ling, M. M.; Liu, S.; Tseng, R. J.; Reese, C.; Roberts, M. E.; Yang, Y.; Wudl, F.; Bao, Z. N. Patterning Organic Single-Crystal Transistor Arrays. Nature 2006, 444, 913-917. (14) Tang, Q.; Li, H.; Song, Y.; Xu, W.; Hu, W.; Jiang, L.; Liu, Y.; Wang, X.; Zhu, D. In Situ Patterning of Organic Single-Crystalline Nanoribbons on a SiO2 Surface for the Fabrication of Various Architectures and High-Quality Transistors. Adv. Mater. 2006, 18, 3010-3014. (15) Lee, K.; Kim, J.; Shin, K.; Kim, Y. S. Micropatterned Crystalline Organic Semiconductors via Direct Pattern Transfer Printing with PDMS Stamp. J. Mater. Chem. 2012, 22, 22763-22768. (16) Li, Y.; Liu, C.; Kumatani, A.; Darmawan, P.; Minari, T.; Tsukagoshi, K. Large Plate-Like Organic Crystals from Direct Spin-Coating for Solution-Processed Field-Effect Transistor Arrays with High Uniformity. Org. Electron. 2012, 13, 264-272.


19


1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 18 19 20 21 22 23 24 25 26 27 28 29 30 31 32 33 34 35 36 37 38 39 40 41 42 43 44 45 46 47 48 49 50 51 52 53 54 55 56 57 58 59 60

Page 20 of 25

(17) Kim, Y. H.; Yoo, B.; Anthony, J. E.; Park, S. K. Controlled Deposition of a HighPerformance Small-Molecule Organic Single-Crystal Transistor Array by Direct Ink-Jet Printing. Adv. Mater. 2012, 24, 497-502. (18) Kan, X. N.; Su, B.; Jiang, L. Precisely Patterning Graphene Sheets through a Liquid-Bridge Induced Strategy. Small 2014, 10, 2570-2577. (19) Su, B.; Wang, S.; Wu, Y.; Chen, X.; Song, Y.; Jiang, L. Small Molecular Nanowire Arrays Assisted by Superhydrophobic Pillar-Structured Surfaces with High Adhesion. Adv. Mater. 2012, 24, 2780-2785. (20) Su, B.; Wang, S.; Ma, J.; Wu, Y.; Chen, X.; Song, Y.; Jiang, L. Elaborate Positioning of Nanowire Arrays Contributed by Highly Adhesive Superhydrophobic Pillar-Structured Substrates. Adv. Mater. 2012, 24, 559-564. (21) Su, B.; Zhang, C.; Chen, S.; Zhang, X.; Chen, L.; Wu, Y.; Nie, Y.; Kan, X.; Song, Y.; Jiang, L. A General Strategy for Assembling Nanoparticles in One Dimension. Adv. Mater. 2014, 26, 2501-2507. (22) Guan, J.; Lee, L. J. Generating Highly Ordered DNA Nanostrand Arrays. Proc. Natl. Acad. Sci. U. S. A. 2005, 102, 18321-18325. (23) Wu, Y.; Chen, X.; Su, B.; Song, Y.; Jiang, L. Elaborately Aligning Bead-Shaped Nanowire Arrays Generated by a Superhydrophobic Micropillar Guiding Strategy. Adv. Funct. Mater. 2012, 22, 4569-4576. (24) Molinari, A. S.; Alves, H.; Chen, Z.; Facchetti, A.; Morpurgo, A. F. High Electron Mobility in Vacuum and Ambient for PDIF-CN2 Single-Crystal Transistors. J. Am. Chem. Soc. 2009, 131, 2462-2466.


20

Page 21 of 25

1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 18 19 20 21 22 23 24 25 26 27 28 29 30 31 32 33 34 35 36 37 38 39 40 41 42 43 44 45 46 47 48 49 50 51 52 53 54 55 56 57 58 59 60


(25) Minder, N. A.; Ono, S.; Chen, Z. H.; Facchetti, A.; Morpurgo, A. F. Band-Like Electron Transport in Organic Transistors and Implication of the Molecular Structure for Performance Optimization. Adv. Mater. 2012, 24, 503-508. (26) Lv, A.; Puniredd, S. R.; Zhang, J.; Li, Z.; Zhu, H.; Jiang, W.; Dong, H.; He, Y.; Jiang, L.; Li, Y.; Pisula, W.; Meng, Q.; Hu, W.; Wang, Z. Air Sable, Organic Single Crystal Transistors of an n-Type Diperylene Bisimide. Adv. Mater. 2012, 24, 2626-2630. (27) Liu, C.; Xiao, C.; Li, Y.; Hu, W.; Li, Z.; Wang, Z. High Performance, Air Stable n-Type Single Crystal Transistors Cased on Core-Tetrachlorinated Perylene Diimides. Chem. Commun. 2014, 50, 12462-12464. (28) Würthner, F.; Saha-Moller, C. R.; Fimmel, B.; Ogi, S.; Leowanawat, P.; Schmidt, D. Perylene Bisimide Dye Assemblies as Archetype Functional Supramolecular Materials. Chem. Rev. 2016, 116, 962-1052. (29) Spenst, P.; Würthner, F. A Perylene Bisimide Cyclophane as a "Turn-On" and "Turn-Off" Fluorescence Probe. Angew. Chem. Int. Ed. 2015, 54, 10165-10168. (30) Gorl, D.; Zhang, X.; Stepanenko, V.; Würthner, F. Supramolecular Block Copolymers by Kinetically Controlled Co-Self-Assembly of Planar and Core-Twisted Perylene Bisimides. Nat. Commun. 2015, 6, 7009. (31) Chen, Z.; Debije, M. G.; Debaerdemaeker, T.; Osswald, P.; Würthner, F. TetrachloroSubstituted Perylene Bisimide Dyes as Promising n-Type Organic Semiconductors:Studies on Structural, Electrochemical and Charge Transport Properties. Chemphyschem 2004, 5, 137-140. (32) Jiang, W.; Li, Y.; Wang, Z. Tailor-Made Rylene Arrays for High Performance n-Channel Semiconductors. Acc. Chem. Res. 2014, 47, 3135-3147.


21


1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 18 19 20 21 22 23 24 25 26 27 28 29 30 31 32 33 34 35 36 37 38 39 40 41 42 43 44 45 46 47 48 49 50 51 52 53 54 55 56 57 58 59 60

Page 22 of 25

(33) Würthner, F.; Sautter, A.; Schilling, J. Synthesis of Diazadibenzoperylenes and Characterization of Their Structural, Optical, Redox, and Coordination Properties. J. Org. Chem. 2002, 67, 3037-3044. (34) Qian, H.; Liu, C.; Wang, Z.; Zhu, D. S-heterocyclic Annelated Perylene Bisimide: Synthesis and Co-Crystal with Pyrene. Chem. Commun. 2006, 44, 4587-4589. (35) Di Motta, S.; Siracusa, M.; Negri, F. Structural and Thermal Effects on the Charge Transport of Core-Twisted Chlorinated Perylene Bisimide Semiconductors. J. Phys. Chem. C 2011, 115, 20754-20764. (36) Schmid, N.; Eichenberger, A. P.; Choutko, A.; Riniker, S.; Winger, M.; Mark, A. E.; van Gunsteren, W. F. Definition and testing of the GROMOS force-field versions 54A7 and 54B7. Eur. Biophys. J. 2011, 40, 843-856. (37) Nose, S. A Unified Formulation of the Constant Temperature Molecular-Dynamics Methods. J. Chem. Phys. 1984, 81, 511-519. (38) Parrinello, M. Polymorphic transitions in single crystals: A New Molecular Dynamics method. J. Appl. Phys. 1981, 52, 7182-7185. (39) Essmann, U.; Perera, L.; Berkowitz, M. L.; Darden, T.; Lee, H.; Pedersen, L. G. A Smooth Particle Mesh Ewald Method. J. Chem. Phys. 1995, 103, 8577-8593. (40) Humphrey, W.; Dalke, A.; Schulten, K. VMD: Visual Molecular Dynamics. J. Mol. Graphics Modell. 1996, 14, 33-38. (41) Jiang, W.; Li, Y.; Yue, W.; Zhen, Y. G.; Qu, J. Q.; Wang, Z. H. One-Pot Facile Synthesis of Pyridyl Annelated Perylene Bisimides. Org. Lett. 2010, 12, 228-231. (42) Yue, W.; Lv, A.; Gao, J.; Jiang, W.; Hao, L.; Li, C.; Li, Y.; Polander, L. E.; Barlow, S.; Hu, W.; Di Motta, S.; Negri, F.; Marder, S. R.; Wang, Z. Hybrid Rylene Arrays via Combination of


22

Page 23 of 25

1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 18 19 20 21 22 23 24 25 26 27 28 29 30 31 32 33 34 35 36 37 38 39 40 41 42 43 44 45 46 47 48 49 50 51 52 53 54 55 56 57 58 59 60


Stille Coupling and C-H Transformation as High-Performance Electron Transport Materials. J. Am. Chem. Soc. 2012, 134, 5770-5773. (43) Zhen, Y. G.; Qian, H. L.; Xiang, J. F.; Qu, J. Q.; Wang, Z. H. Highly Regiospecific Synthetic Approach to Monobay-Functionalized Perylene Bisimide and Di(perylene bisimide). Org. Lett. 2009, 11, 3084-3087. (44) Pschirer, N. G.; Kohl, C.; Nolde, F.; Qu, J.; Müllen, K. Pentarylene- and Hexarylenebis(dicarboximide)s: Near-Infrared-Absorbing Polyaromatic Dyes. Angew. Chem. Int. Ed. 2006, 45, 1401-1404. (45) Anantharaju, N.; Panchagnula, M.; Neti, S. Evaporating Drops on Patterned Surfaces: Transition from Pinned to Moving Triple Line. J. Colloid Interface Sci. 2009, 337, 176-182. (46) Pittoni, P. G.; Chang, C. C.; Yu, T. S.; Lin, S. Y. Evaporation of Water Drops on Polymer Surfaces: Pinning, Depinning and Dynamics of the Triple Line. Colloids Surf., A 2013, 432, 8998. (47) Liu, C. Y.; Tang, H. J.; Allen, J. B. Effect of Orientation of Porphyrin Single-Crystal Slices on Optoelectronic Properties. J. Phys. Chem. 1996, 100, 3587-3591. (48) Giri, G.; Park, S.; Vosgueritchian, M.; Shulaker, M. M.; Bao, Z. N. High-mobility, Aligned Crystalline Domains of TIPS-pentacene with Metastable Polymorphs through Lateral Confinement of Crystal Growth. Adv. Mater. 2014, 26, 487-493. (49) Jones, B. A.; Facchetti, A.; Wasielewski, M. R.; Marks, T. J. Tuning Orbital Energetics in Arylene Diimide Semiconductors. Materials Design for Ambient Stability of n-Type Charge Transport. J. Am. Chem. Soc. 2007, 129, 15259-15278. (50) Li, L.; Yu, Y.; Ye, G. J.; Ge, Q.; Ou, X.; Wu, H.; Feng, D.; Chen, X. H.; Zhang, Y. Black Phosphorus Field-Effect Transistors. Nat. Nanotechnol. 2014, 9, 372-377.


23


1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 18 19 20 21 22 23 24 25 26 27 28 29 30 31 32 33 34 35 36 37 38 39 40 41 42 43 44 45 46 47 48 49 50 51 52 53 54 55 56 57 58 59 60

Page 24 of 25

(51) Oh, J. H.; Suraru, S. L.; Lee, W. Y.; Konemann, M.; Hoffken, H. W.; Roger, C.; Schmidt, R.; Chung, Y.; Chen, W. C.; Würthner, F.; Bao, Z. N. High-Performance Air-Stable n-Type Organic Transistors Based on Core-Chlorinated Naphthalene Tetracarboxylic Diimides. Adv. Funct. Mater. 2010, 20, 2148-2156.


24

Page 25 of 25

1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 18 19 20 21 22 23 24 25 26 27 28 29 30 31 32 33 34 35 36 37 38 39 40 41 42 43 44 45 46 47 48 49 50 51 52 53 54 55 56 57 58 59 60


Table of Contents Graphic


25

A Dewetting-Induced Assembly Strategy for Precisely Patterning

Recommend Documents