High crystalline dithienosilole-cored small molecule semiconductor for ambipolar transistor and nonvolatile memory

ACS Applied Materials and Interfaces

Volumn 6, Issue 9, 2014, Pages 6589-6597

  Kang, Woonggi ^a   Jung, Minwoo ^b,c   Cha, Wonsuk ^d   Jang, Sukjae ^a   Yoon, Youngwoon ^b   Kim, Hyunjung ^d   Son, Hae Jung ^b   Lee, Doh Kwon ^b   Kim, Bongsoo ^b   Cho, Jeong Ho ^a  

^a Sungkyunkwan University   (South Korea)

^b Korea Institute of Science and Technology   (South Korea)

^c Korea University   (South Korea)

^d Sogang University   (South Korea)

Author keywords

ambipolar field effect transistor; charge trapping; crystallinity; donor Acceptor type small molecules; hole mobility; nonvolatile memory

Indexed keywords

ATOMIC FORCE MICROSCOPY; CHARGE TRAPPING; ELECTRON MOBILITY; FIELD EFFECT TRANSISTORS; GOLD; HOLE MOBILITY; NONVOLATILE STORAGE; SILICON OXIDES; THIOPHENE; X RAY DIFFRACTION;

CRYSTALLINITIES; ELECTRICAL RELIABILITY; GRAZING INCIDENCE X-RAY DIFFRACTION; NON-VOLATILE MEMORY; NON-VOLATILE MEMORY APPLICATION; NONVOLATILE MEMORY DEVICES; ON/OFF-CURRENT RATIOS; SMALL MOLECULES;

MOLECULES;

EID: 84900869244     PISSN: 19448244     EISSN: 19448252     Source Type: Journal    
DOI: 10.1021/am500080p     Document Type: Conference Paper

References (44)

1. Chua, L.-L.; Zaumseil, J.; Chang, J.-F.; Ou, E. C.-W.; Ho, P. K.-H.; Sirringhaus, H.; Friend, R. H. General Observation of N-Type Field-Effect Behaviour in Organic Semiconductors Nature 2005, 434, 194-199
2. Yan, H.; Chen, Z.; Zheng, Y.; Newman, C.; Quinn, J. R.; Dötz, F.; Kastler, M.; Facchetti, A. A High-Mobility Electron-Transporting Polymer for Printed Transistors Nature 2009, 457, 679-686
3. Zaumseil, J.; Sirringhaus, H. Electron and Ambipolar Transport in Organic Field-Effect Transistors Chem. Rev. 2007, 107, 1296-1323
4. Zhang, W.; Smith, J.; Watkins, S. E.; Gysel, R.; McGehee, M.; Salleo, A.; Kirkpatrick, J.; Ashraf, S.; Anthopoulos, T.; Heeney, M. Indacenodithiophene Semiconducting Polymers for High-Performance, Air-Stable Transistors J. Am. Chem. Soc. 2010, 132, 11437-11439
5. de Gans, B. J.; Duineveld, P. C.; Schubert, U. S. Inkjet Printing of Polymers: State of the Art and Future Developments Adv. Mater. 2004, 16, 203-213
6. Sirringhaus, H.; Tessler, N.; Friend, R. H. Integrated Optoelectronic Devices Based on Conjugated Polymers Science 1998, 280, 1741-1744
7. McCulloch, I.; Heeney, M.; Bailey, C.; Genevicius, K.; MacDonald, I.; Shkunov, M.; Sparrowe, D.; Tierney, S.; Wagner, R.; Zhang, W. Liquid-Crystalline Semiconducting Polymers with High Charge-Carrier Mobility Nat. Mater. 2006, 5, 328-333
8. Dimitrakopoulos, C. D.; Malenfant, P. R. Organic Thin Film Transistors for Large Area Electronics Adv. Mater. 2002, 14, 99-117
9. Beaujuge, P. M.; Pisula, W.; Tsao, H. N.; Ellinger, S.; Müllen, K.; Reynolds, J. R. Tailoring Structure-Property Relationships in Dithienosilole-Benzothiadiazole Donor-Acceptor Copolymers J. Am. Chem. Soc. 2009, 131, 7514-7515
10. Cho, J. H.; Lee, J.; Xia, Y.; Kim, B.; He, Y.; Renn, M. J.; Lodge, T. P.; Frisbie, C. D. Printable Ion-Gel Gate Dielectrics for Low-Voltage Polymer Thin-Film Transistors on Plastic Nat. Mater. 2008, 7, 900-906
11. Usta, H.; Facchetti, A.; Marks, T. J. N-Channel Semiconductor Materials Design for Organic Complementary Circuits Acc. Chem. Res. 2011, 44, 501-510
12. Bronstein, H.; Chen, Z.; Ashraf, R. S.; Zhang, W.; Du, J.; Durrant, J. R.; Shakya Tuladhar, P.; Song, K.; Watkins, S. E.; Geerts, Y. Thieno[3, 2-b]thiophene- Diketopyrrolopyrrole-Containing Polymers for High-Performance Organic Field-Effect Transistors and Organic Photovoltaic Devices J. Am. Chem. Soc. 2011, 133, 3272-3275
13. Crouch, D. J.; Skabara, P. J.; Lohr, J. E.; McDouall, J. J.; Heeney, M.; McCulloch, I.; Sparrowe, D.; Shkunov, M.; Coles, S. J.; Horton, P. N. Thiophene and Selenophene Copolymers Incorporating Fluorinated Phenylene Units in the Main Chain: Synthesis, Characterization, and Application in Organic Field-Effect Transistors Chem. Mater. 2005, 17, 6567-6578
14. Lei, T.; Cao, Y.; Zhou, X.; Peng, Y.; Bian, J.; Pei, J. Systematic Investigation of Isoindigo-Based Polymeric Field-Effect Transistors: Design Strategy and Impact of Polymer Symmetry and Backbone Curvature Chem. Mater. 2012, 24, 1762-1770
15. Mei, J.; Kim, D. H.; Ayzner, A. L.; Toney, M. F.; Bao, Z. Siloxane-Terminated Solubilizing Side Chains: Bringing Conjugated Polymer Backbones Closer and Boosting Hole Mobilities in Thin-Film Transistors J. Am. Chem. Soc. 2011, 133, 20130-20133
16. Bijleveld, J. C.; Zoombelt, A. P.; Mathijssen, S. G.; Wienk, M. M.; Turbiez, M.; de Leeuw, D. M.; Janssen, R. A. Poly (Diketopyrrolopyrrole- Terthiophene) for Ambipolar Logic and Photovoltaics J. Am. Chem. Soc. 2009, 131, 16616-16617
17. Lee, J. S.; Son, S. K.; Song, S.; Kim, H.; Lee, D. R.; Kim, K.; Ko, M. J.; Choi, D. H.; Kim, B.; Cho, J. H. Importance of Solubilizing Group and Backbone Planarity in Low Band Gap Polymers for High Performance Ambipolar Field-Effect Transistors Chem. Mater. 2012, 24, 1316-1323
18. Tsao, H. N.; Cho, D. M.; Park, I.; Hansen, M. R.; Mavrinskiy, A.; Yoon, D. Y.; Graf, R.; Pisula, W.; Spiess, H. W.; Müllen, K. Ultrahigh Mobility in Polymer Field-Effect Transistors by Design J. Am. Chem. Soc. 2011, 133, 2605-2612
19. Guo, X.; Kim, F. S.; Seger, M. J.; Jenekhe, S. A.; Watson, M. D. Naphthalene Diimide-Based Polymer Semiconductors: Synthesis, Structure-Property Correlations, and N-Channel and Ambipolar Field-Effect Transistors Chem. Mater. 2012, 24, 1434-1442
20. Lee, H.-S.; Lee, J. S.; Cho, S.; Kim, H.; Kwak, K.-W.; Yoon, Y.; Son, S. K.; Kim, H.; Ko, M. J.; Lee, D.-K. Crystallinity-Controlled Naphthalene-Alt- Diketopyrrolopyrrole Copolymers for High-Performance Ambipolar Field Effect Transistors J. Phys. Chem. C 2012, 116, 26204-26213
21. Lee, J.; Han, A.-R.; Kim, J.; Kim, Y.; Oh, J. H.; Yang, C. Solution-Processable Ambipolar Diketopyrrolopyrrole-Selenophene Polymer with Unprecedentedly High Hole and Electron Mobilities J. Am. Chem. Soc. 2012, 134, 20713-20721
22. Sonar, P.; Singh, S. P.; Li, Y.; Soh, M. S.; Dodabalapur, A. A Low-Bandgap Diketopyrrolopyrrole-Benzothiadiazole-Based Copolymer for High-Mobility Ambipolar Organic Thin-Film Transistors Adv. Mater. 2010, 22, 5409-5413
23. Zhou, E.; Yamakawa, S.; Tajima, K.; Yang, C.; Hashimoto, K. Synthesis and Photovoltaic Properties of Diketopyrrolopyrrole-Based Donor- Acceptor Copolymers Chem. Mater. 2009, 21, 4055-4061
24. Sirringhaus, H.; Kawase, T.; Friend, R.; Shimoda, T.; Inbasekaran, M.; Wu, W.; Woo, E. High-Resolution Inkjet Printing of All-Polymer Transistor Circuits Science 2000, 290, 2123-2126
25. Braga, D.; Erickson, N. C.; Renn, M. J.; Holmes, R. J.; Frisbie, C. D. High-Transconductance Organic Thin-Film Electrochemical Transistors for Driving Low-Voltage Red-Green-Blue Active Matrix Organic Light-Emitting Devices Adv. Funct. Mater. 2012, 22, 1623-1631
26. Facchetti, A. Π-Conjugated Polymers for Organic Electronics and Photovoltaic Cell Applications Chem. Mater. 2010, 23, 733-758
27. Crone, B.; Dodabalapur, A.; Lin, Y.-Y.; Filas, R.; Bao, Z.; LaDuca, A.; Sarpeshkar, R.; Katz, H.; Li, W. Large-Scale Complementary Integrated Circuits Based on Organic Transistors Nature 2000, 403, 521-523
28. Meijer, E.; De Leeuw, D.; Setayesh, S.; Van Veenendaal, E.; Huisman, B.-H.; Blom, P.; Hummelen, J.; Scherf, U.; Klapwijk, T. Solution-Processed Ambipolar Organic Field-Effect Transistors and Inverters Nat. Mater. 2003, 2, 678-682
29. -1 Adv. Mater. 2010, 22, 3598-3602
30. Kim, F. S.; Guo, X.; Watson, M. D.; Jenekhe, S. A. High-Mobility Ambipolar Transistors and High-Gain Inverters from a Donor-Acceptor Copolymer Semiconductor Adv. Mater. 2010, 22, 478-482
31. Dodabalapur, A.; Katz, H.; Torsi, L.; Haddon, R. Organic Heterostructure Field-Effect Transistors Science 1995, 269, 1560-1562
32. Beaujuge, P. M.; Fréchet, J. M. Molecular Design and Ordering Effects in Π-Functional Materials for Transistor and Solar Cell Applications J. Am. Chem. Soc. 2011, 133, 20009-20029
33. Li, Y. Molecular Design of Photovoltaic Materials for Polymer Solar Cells: Toward Suitable Electronic Energy Levels and Broad Absorption Acc. Chem. Res. 2012, 45, 723-733
34. Coughlin, J. E.; Henson, Z. B.; Welch, G. C.; Bazan, G. C. Design and Synthesis of Molecular Donors for Solution-Processed High-Efficiency Organic Solar Cells Acc. Chem. Res. 2013, 47, 257-270
35. Mei, J.; Diao, Y.; Appleton, A. L.; Fang, L.; Bao, Z. Integrated Materials Design of Organic Semiconductors for Field-Effect Transistors J. Am. Chem. Soc. 2013, 135, 6724-6746
36. Arias, A. C.; MacKenzie, J. D.; McCulloch, I.; Rivnay, J.; Salleo, A. Materials and Applications for Large Area Electronics: Solution-Based Approaches Chem. Rev. 2010, 110, 3-24
37. Zhang, Y.; Kim, C.; Lin, J.; Nguyen, T.-Q. Solution-Processed Ambipolar Field-Effect Transistor Based on Diketopyrrolopyrrole Functionalized with Benzothiadiazole Adv. Funct. Mater. 2012, 22, 97-105
38. Chen, H.-Y.; Hou, J.; Hayden, A. E.; Yang, H.; Houk, K. N.; Yang, Y. Silicon Atom Substitution Enhances Interchain Packing in a Thiophene-Based Polymer System Adv. Mater. 2010, 22, 371-375
39. Welch, G. C.; Bakus, R. C.; Teat, S. J.; Bazan, G. C. Impact of Regiochemistry and Isoelectronic Bridgehead Substitution on the Molecular Shape and Bulk Organization of Narrow Bandgap Chromophores J. Am. Chem. Soc. 2013, 135, 2298-2305
40. Grisorio, R.; Allegretta, G.; Suranna, G. P.; Mastrorilli, P.; Loiudice, A.; Rizzo, A.; Mazzeo, M.; Gigli, G. Monodispersed Vs. Polydispersed Systems for Bulk Heterojunction Solar Cells: The Case of Dithienopyrrole/Anthracene Based Materials J. Mater. Chem. 2012, 22, 19752-19760
41. Loser, S.; Bruns, C. J.; Miyauchi, H.; Ortiz, R. P.; Facchetti, A.; Stupp, S. I.; Marks, T. J. A Naphthodithiophene-Diketopyrrolopyrrole Donor Molecule for Efficient Solution-Processed Solar Cells J. Am. Chem. Soc. 2011, 133, 8142-8145
42. Walker, B.; Liu, J.; Kim, C.; Welch, G. C.; Park, J. K.; Lin, J.; Zalar, P.; Proctor, C. M.; Seo, J. H.; Bazan, G. C.; Nguyen, T.-Q. Optimization of Energy Levels by Molecular Design: Evaluation of Bis-Diketopyrrolopyrrole Molecular Donor Materials for Bulk Heterojunction Solar Cells Energy Environ. Sci. 2013, 6, 952-962
43. Sonar, P.; Williams, E. L.; Singh, S. P.; Manzhos, S.; Dodabalapur, A. A Benzothiadiazole End Capped Donor-Acceptor Based Small Molecule for Organic Electronics Phys. Chem. Chem. Phys. 2013, 15, 17064-17069
44. Tantiwiwat, M.; Tamayo, A.; Luu, N.; Dang, X.-D.; Nguyen, T.-Q. Oligothiophene Derivatives Functionalized with a Diketopyrrolopyrrolo Core for Solution-Processed Field Effect Transistors: Effect of Alkyl Substituents and Thermal Annealing J. Phys. Chem. C 2008, 112, 17402-17407