Prediction of charge mobility in organic semiconductors with consideration of the grain-size effect

A new computational model to predict the hole mobility of poly-crystalline organic semiconductors in thin film was developed (refer to Phys. Chem. Chem. Phys., 2016, DOI: 10.1039/C6CP02993K). Site energy differences and transfer integrals in crystalline morphologies of organic molecules were obtained from quantum chemical calculation, in which the periodic boundary condition was efficiently applied to capture the interactions with the surrounding molecules in the crystalline organic layer. Then the parameters were employed in kinetic Monte Carlo (kMC) simulations to estimate the carrier mobility. Carrier transport in multiple directions has been considered in the kMC simulation to mimic polycrystalline characteristic in thin-film condition. Furthermore, the calculated mobility was corrected with a calibration equation based on the microscopic images of thin films to take the effect of grain boundary into account. As a result, good agreement was observed between the predicted and measured hole mobility values for 21 molecular species: the coefficient of determination (R2) was estimated to be 0.83 and the mean absolute error was 1.32 cm2 V−1 s−1. This numerical approach can be applied to any molecules for which crystal structures are available and will provide a rapid and precise way of predicting the device performance.

[1]  Gilles Horowitz,et al.  Temperature and gate voltage dependence of hole mobility in polycrystalline oligothiophene thin film transistors , 2000 .

[2]  Claire S. Adjiman,et al.  Towards crystal structure prediction of complex organic compounds – a report on the fifth blind test , 2011, Acta crystallographica. Section B, Structural science.

[3]  H. Bässler,et al.  How do disorder, reorganization, and localization influence the hole mobility in conjugated copolymers? , 2013, Journal of the American Chemical Society.

[4]  Rudolph A. Marcus,et al.  Electron transfer reactions in chemistry. Theory and experiment , 1993 .

[5]  J. Nelson,et al.  Simulating charge transport in tris(8-hydroxyquinoline) aluminium (Alq(3)). , 2008, Physical chemistry chemical physics : PCCP.

[6]  M. Oh-e,et al.  Estimation of charge carrier mobility in amorphous organic materials using percolation corrected random-walk model , 2016 .

[7]  K N Houk,et al.  Theoretical study of the molecular ordering, paracrystallinity, and charge mobilities of oligomers in different crystalline phases. , 2015, Journal of the American Chemical Society.

[8]  Tatsuo Hasegawa,et al.  Organic field-effect transistors using single crystals , 2009, Science and technology of advanced materials.

[9]  Denis Andrienko,et al.  Challenges for in silico design of organic semiconductors , 2012 .

[10]  Fang Wang,et al.  A highly pi-stacked organic semiconductor for field-effect transistors based on linearly condensed pentathienoacene. , 2005, Journal of the American Chemical Society.

[11]  B. Batlogg,et al.  Modeling of the temperature dependence of the field-effect mobility in thin film devices of conjugated oligomers , 1999 .

[12]  D. Gillespie.  A General Method for Numerically Simulating the Stochastic Time Evolution of Coupled Chemical Reactions , 1976 .

[13]  Sang Yoon Lee,et al.  Dibenzothiopheno[6,5-b:6',5'-f]thieno[3,2-b]thiophene (DBTTT): high-performance small-molecule organic semiconductor for field-effect transistors. , 2015, Journal of the American Chemical Society.

[14]  A. Morpurgo,et al.  Tunable Fröhlich polarons in organic single-crystal transistors , 2006, Nature materials.

[15]  Hiroki Mori,et al.  Alkylated Dinaphtho[2,3‐b:2′,3′‐f]Thieno[3,2‐b]Thiophenes (Cn‐DNTTs): Organic Semiconductors for High‐Performance Thin‐Film Transistors , 2011, Advanced materials.

[16]  J. Fréchet,et al.  Organic semiconducting oligomers for use in thin film transistors. , 2007, Chemical reviews.

[17]  K. Müllen,et al.  Benzo[1,2-b:4,5-b']bis[b]benzothiophene as solution processible organic semiconductor for field-effect transistors. , 2008, Chemical communications.

[18]  P. Johari,et al.  Rationally designed donor-acceptor scheme based molecules for applications in opto-electronic devices. , 2016, Physical chemistry chemical physics : PCCP.

[19]  Kazuo Takimiya,et al.  Highly soluble [1]benzothieno[3,2-b]benzothiophene (BTBT) derivatives for high-performance, solution-processed organic field-effect transistors. , 2007, Journal of the American Chemical Society.

[20]  Qiang Shi,et al.  Theoretical study on charge carrier mobilities of tetrathiafulvalene derivatives. , 2011, Physical chemistry chemical physics : PCCP.

[21]  V. May,et al.  Charge and Energy Transfer Dynamics in Molecular Systems: MAY:CHARGE TRANSFER 3ED O-BK , 2011 .

[22]  Daoben Zhu,et al.  High-Performance, Stable Organic Field-Effect Transistors Based on trans-1,2-(Dithieno[2,3-b:3′,2′-d]thiophene)ethene , 2009 .

[23]  Karl Leo,et al.  Molecular-scale simulation of electroluminescence in a multilayer white organic light-emitting diode. , 2013, Nature materials.

[24]  David Beljonne,et al.  Charge-transfer and energy-transfer processes in pi-conjugated oligomers and polymers: a molecular picture. , 2004, Chemical reviews.

[25]  Daoben Zhu,et al.  Semiconducting π-conjugated systems in field-effect transistors: a material odyssey of organic electronics. , 2012, Chemical reviews.

[26]  Hao‐Li Zhang,et al.  High performance n-type and ambipolar small organic semiconductors for organic thin film transistors. , 2014, Physical chemistry chemical physics : PCCP.

[27]  William A. Goddard,et al.  Predictions of Hole Mobilities in Oligoacene Organic Semiconductors from Quantum Mechanical Calculations , 2004 .

[28]  H. Sirringhaus,et al.  Organic electronics-new physical chemistry insight. , 2012, Physical chemistry chemical physics : PCCP.

[29]  Zhenan Bao,et al.  Integrated materials design of organic semiconductors for field-effect transistors. , 2013, Journal of the American Chemical Society.

[30]  Takashi Nemoto,et al.  Temperature and electric-field dependence of the mobility of a single-grain pentacene field-effect transistor , 2006 .

[31]  K. Takimiya,et al.  Unique three-dimensional (3D) molecular array in dimethyl-DNTT crystals: a new approach to 3D organic semiconductors , 2010 .

[32]  Yi Zhao,et al.  Charge transfer in organic molecules for solar cells: theoretical perspective. , 2012, Chemical Society reviews.

[33]  Jean-Luc Brédas,et al.  Charge transport in organic semiconductors. , 2007, Chemical reviews.

[34]  A. Heeger,et al.  High mobility emissive organic semiconductor , 2015, Nature Communications.

[35]  Shubin Liu,et al.  Synthesis, crystal structures, and electronic properties of nonlinear fused thienoacene semiconductors. , 2011, Organic letters.

[36]  J. Nelson,et al.  Modeling charge transport in organic photovoltaic materials. , 2009, Accounts of chemical research.

[37]  K. Takimiya,et al.  FET characteristics of dinaphthothienothiophene (DNTT) on Si/SiO2 substrates with various surface-modifications , 2007 .

[38]  C. Frisbie,et al.  Temperature and gate voltage dependent transport across a single organic semiconductor grain boundary , 2001 .

[39]  Pascal Friederich,et al.  Ab Initio Treatment of Disorder Effects in Amorphous Organic Materials: Toward Parameter Free Materials Simulation. , 2014, Journal of chemical theory and computation.

[40]  I. Osaka,et al.  Largely π-extended thienoacenes with internal thieno[3,2-b]thiophene substructures: synthesis, characterization, and organic field-effect transistor applications. , 2012, Organic letters.

[41]  Chih-Hsien Yuan,et al.  The synthesis, crystal structure and charge-transport properties of hexacene. , 2012, Nature chemistry.

[42]  Yan Li,et al.  Heteroarenes as high performance organic semiconductors. , 2013, Chemical Society reviews.

[43]  Fabio Biscarini,et al.  Molecular reorganization in organic field-effect transistors and its effect on two-dimensional charge transport pathways. , 2013, ACS nano.

[44]  O. Grassmann,et al.  Combined crystal structure prediction and high-pressure crystallization in rational pharmaceutical polymorph screening , 2015, Nature Communications.

[45]  H. Koinuma,et al.  High-performance organic field-effect transistors based on pi-extended tetrathiafulvalene derivatives. , 2005, Journal of the American Chemical Society.

[46]  Alán Aspuru-Guzik,et al.  From computational discovery to experimental characterization of a high hole mobility organic crystal , 2011, Nature communications.

[47]  A. Seidel-Morgenstern,et al.  Are the Crystal Structures of Enantiopure and Racemic Mandelic Acids Determined by Kinetics or Thermodynamics? , 2015, Journal of the American Chemical Society.

[48]  Itaru Osaka,et al.  General synthesis of dinaphtho[2,3-b:2',3'-f]thieno[3,2-b]thiophene (DNTT) derivatives. , 2011, Organic letters.

[49]  Luisa Torsi,et al.  Organic thin-film transistors as plastic analytical sensors. , 2005, Analytical chemistry.

[50]  D. Gillespie.  Exact Stochastic Simulation of Coupled Chemical Reactions , 1977 .

[51]  BTQBT (bis-(1,2,5-thiadiazolo)-p-quinobis(1,3-dithiole)) thin films; A promising candidate for high mobility organic transistors , 2002 .

[52]  I. Osaka,et al.  Consecutive thiophene-annulation approach to π-extended thienoacene-based organic semiconductors with [1]benzothieno[3,2-b][1]benzothiophene (BTBT) substructure. , 2013, Journal of the American Chemical Society.

[53]  B. Batlogg,et al.  Trapping in organic field-effect transistors , 2001 .

[54]  Yong‐Young Noh,et al.  Development of high-performance printed organic field-effect transistors and integrated circuits. , 2015, Physical chemistry chemical physics : PCCP.

[55]  Sui‐Dong Wang,et al.  Understanding contact behavior in organic thin film transistors , 2010 .