Organic semiconductors based on [1]benzothieno[3,2- B ][1]benzothiophene substructure

Accounts of Chemical Research

Volumn 47, Issue 5, 2014, Pages 1493-1502

  Takimiya, Kazuo ^a,b   Osaka, Itaru ^a   Mori, Takamichi ^a,b   Nakano, Masahiro ^a  

^a RIKEN Center for Emergent Matter Science   (Japan)

^b HIROSHIMA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 84901257317     PISSN: 00014842     EISSN: 15204898     Source Type: Journal    
DOI: 10.1021/ar400282g     Document Type: Article

References (54)

1. The Special Issue on Organic Electronics. Chem. Mater. 2004, 16, 4381-4382.
2. Bredas, J.-L.; Marder, S. R.; Reichmanis, E. Preface to the Chemistry of Materials Special Issue on π-Functional Materials Chem. Mater. 2011, 23, 309-309
3. Bao, Z.; Locklin, J., Eds. Organic Field-Effect Transistors; CRC Press: Boca Raton, FL, 2007.
4. Horowitz, G.; Peng, X.-Z.; Fichou, D.; Garnier, F. Role of the semiconductor/insulator interface in the characteristics of π-conjugated- oligomer-based thin-film transistors Synth. Met. 1992, 51, 419-424
5. Kelley, T. W.; Boardman, L. D.; Dunbar, T. D.; Muyres, D. V.; Pellerite, M. J.; Smith, T. P. High-Performance OTFTs Using Surface-Modified Alumina Dielectrics J. Phys. Chem. B 2003, 107, 5877-5881
6. Organic Electronics, Manufacturing and Applications; Klauk, H., Ed.; Wiley-VCH: Weinheim, 2006.
7. Anthony, J. E. Functionalized Acenes and Heteroacenes for Organic Electronics Chem. Rev. 2006, 106, 5028-5048
8. Anthony, J. E. The Larger Acenes: Versatile Organic Semiconductors Angew. Chem., Int. Ed. 2008, 47, 452-483
9. Murphy, A. R.; Fréchet, J. M. J. Organic Semiconducting Oligomers for Use in Thin Film Transistors Chem. Rev. 2007, 107, 1066-1096
10. 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
11. Meng, H.; Bao, Z.; Lovinger, A. J.; Wang, B.-C.; Mujsce, A. M. High Field-Effect Mobility Oligofluorene Derivatives with High Environmental Stability J. Am. Chem. Soc. 2001, 123, 9214-9215
12. Brédas, J.-L.; Beljonne, D.; Coropceanu, V.; Cornil, J. Charge-Transfer and Energy-Transfer Processes in π-Conjugated Oligomers and Polymers: A Molecular Picture Chem. Rev. 2004, 104, 4971-5004
13. Katz, H. E.; Torsi, L.; Dodabalapur, A. Synthesis, Material Properties, and Transistor Performance of Highly Pure Thiophene Oligomers Chem. Mater. 1995, 7, 2235-2237
14. Horowitz, G.; Garnier, F.; Yassar, A.; Hajlaoui, R.; Kouki, F. Field-effect transistor made with a sexithiophene single crystal Adv. Mater. 1996, 8, 52-54
15. Laquindanum, J. G.; Katz, H. E.; Lovinger, A. J.; Dodabalapur, A. Benzodithiophene Rings as Semiconductor Building Blocks Adv. Mater. 1997, 9, 36-39
16. Li, X.-C.; Sirringhaus, H.; Garnier, F.; Holmes, A. B.; Moratti, S. C.; Feeder, N.; Clegg, W.; Teat, S. J.; Friend, R. H. A Highly π-Stacked Organic Semiconductor for Thin Film Transistors Based on Fused Thiophenes J. Am. Chem. Soc. 1998, 120, 2206-2207
17. Horton, A. W. The Mechanism of The Reactions of Hydrocarbons with Sulfur 1 J. Org. Chem. 1949, 14, 761-770
18. Košata, B.; Kozmík, V.; Svoboda, J. Reactivity of [1]Benzothieno[3,2- b ][1]benzothiophene-Electrophilic and Metallation Reactions Collect. Czech. Chem. Commun. 2002, 67, 645-664
19. Saito, M.; Osaka, I.; Miyazaki, E.; Takimiya, K.; Kuwabara, H.; Ikeda, M. One-step synthesis of [1]benzothieno[3,2- b ][1]benzothiophene from o -chlorobenzaldehyde Tetrahedron Lett. 2011, 52, 285-288
20. Sashida, H.; Yasuike, S. A simple one-pot synthesis of [1]benzotelluro[3,2- b ][1]benzotellurophenes and its selenium and sulfur analogues from 2,2′-dibromodiphenylacetylene J. Heterocycl. Chem. 1998, 35, 725-726
21. Zherdeva, S. Y.; Barudi, A.; Zheltov, A. Y.; Stepanov, B. I. Synthesis and transformations of benzo[3,2- b ]benzothiophenes Zh. Org. Khim. 1980, 16, 430-438
22. Kaszynski, P.; Dougherty, D. A. Synthesis and properties of diethyl 5,10-dihetera-5,10-dihydroindeno[2,1- a ]indene-2,7-dicarboxylates J. Org. Chem. 1993, 58, 5209-5220
23. Ruzié, C.; Karpinska, J.; Kennedy, A. R.; Geerts, Y. H. Synthesis of 1,6-, 2,7-, 3,8-, and 4,9-Isomers of Didodecyl[1]benzothieno[3,2- b ][1]benzothiophenes J. Org. Chem. 2013, 78, 7741-7748
24. -1 J. Am. Chem. Soc. 2006, 128, 12604-12605
25. Ebata, H.; Izawa, T.; Miyazaki, E.; Takimiya, K.; Ikeda, M.; Kuwabara, H.; Yui, T. Highly Soluble [1]Benzothieno[3,2- b ]benzothiophene (BTBT) Derivatives for High-Performance, Solution-Processed Organic Field-Effect Transistors J. Am. Chem. Soc. 2007, 129, 15732-15733
26. Izawa, T.; Miyazaki, E.; Takimiya, K. Molecular Ordering of High-Performance Soluble Molecular Semiconductors and Re-evaluation of Their Field-Effect Transistor Characteristics Adv. Mater. 2008, 20, 3388-3392
27. Iino, H.; Kobori, T.; Hanna, J.-i. Improved thermal stability in organic FET fabricated with a soluble BTBT derivative J. Non-Cryst. Solids 2012, 358, 2516-2519
28. Amin, A. Y.; Khassanov, A.; Reuter, K.; Meyer-Friedrichsen, T.; Halik, M. Low-Voltage Organic Field Effect Transistors with a 2-Tridecyl[1]benzothieno[3, 2- b ][1]benzothiophene Semiconductor Layer J. Am. Chem. Soc. 2012, 134, 16548-16550
29. Yamamoto, T.; Takimiya, K. Facile Synthesis of Highly π-Extended Heteroarenes, Dinaphtho[2,3- b:2′,3′- f ]chalcogenopheno[3,2- b ]chalcogenophenes, and Their Application to Field-Effect Transistors J. Am. Chem. Soc. 2007, 129, 2224-2225
30. Kuribara, K.; Wang, H.; Uchiyama, N.; Fukuda, K.; Yokota, T.; Zschieschang, U.; Jaye, C.; Fischer, D.; Klauk, H.; Yamamoto, T.; Takimiya, K.; Ikeda, M.; Kuwabara, H.; Sekitani, T.; Loo, Y.-L.; Someya, T. Organic transistors with high thermal stability for medical applications Nat. Commun. 2012, 3, 723
31. Kaltenbrunner, M.; Sekitani, T.; Reeder, J.; Yokota, T.; Kuribara, K.; Tokuhara, T.; Drack, M.; Schwodiauer, R.; Graz, I.; Bauer-Gogonea, S.; Bauer, S.; Someya, T. An ultra-lightweight design for imperceptible plastic electronics Nature 2013, 499, 458-463
32. n-DNTTs): Organic Semiconductors for High-Performance Thin-Film Transistors Adv. Mater. 2011, 23, 1222-1225
33. Niimi, K.; Kang, M. J.; Miyazaki, E.; Osaka, I.; Takimiya, K. General Synthesis of Dinaphtho[2,3- b:2′,3′- f ]thieno[3,2- b ]thiophene (DNTT) Derivatives Org. Lett. 2011, 13, 3430-3433
34. Niimi, K.; Shinamura, S.; Osaka, I.; Miyazaki, E.; Takimiya, K. Dianthra[2,3- b:2′,3′- f ]thieno[3,2- b ]thiophene (DATT): Synthesis, Characterization, and FET Characteristics of New π-Extended Heteroarene with Eight Fused Aromatic Rings J. Am. Chem. Soc. 2011, 133, 8732-8739
35. Yamamoto, T.; Nishimura, T.; Mori, T.; Miyazaki, E.; Osaka, I.; Takimiya, K. Largely π-Extended Thienoacenes with Internal Thieno[3,2- b ]thiophene Substructures: Synthesis, Characterization, and Organic Field-Effect Transistor Applications Org. Lett. 2012, 14, 4914-4917
36. Mori, T.; Nishimura, T.; Yamamoto, T.; Doi, I.; Miyazaki, E.; Osaka, I.; Takimiya, K. Consecutive Thiophene-Annulation Approach to π-Extended Thienoacene-Based Organic Semiconductors with [1]Benzothieno[3,2- b ][1]benzothiophene (BTBT) Substructure J. Am. Chem. Soc. 2013, 135, 13900-13913
37. Inokuchi, H.; Saito, G.; Wu, P.; Seki, K.; Tang, T. B.; Mori, T.; Imaeda, K.; Enoki, T.; Higuchi, Y.; Inaka, K.; Yasuoka, N. A Novel Type of Organic Semiconductors. Molecular Fastener Chem. Lett. 1986, 15, 1263-1266
38. Nan, G.; Li, Z. Crystal structure versus charge transport in organic single crystals of [1]benzothieno[3,2- b ][1]benzothiophene derivatives from a multiscale theoretical study J. Mater. Chem. C 2014, 2, 1447-1456
39. Takimiya, K.; Yamamoto, T.; Ebata, H.; Izawa, T. Design strategy for air-stable organic semiconductors applicable to high-performance field-effect transistors Sci. Technol. Adv. Mater. 2007, 8, 273-276
40. Endo, T.; Nagase, T.; Kobayashi, T.; Takimiya, K.; Ikeda, M.; Naito, H. Solution-Processed Dioctylbenzothienobenzothiophene-Based Top-Gate Organic Transistors with High Mobility, Low Threshold Voltage, and High Electrical Stability Appl. Phys. Express 2010, 3, 121601
41. Kano, M.; Minari, T.; Tsukagoshi, K. All-Solution-Processed Selective Assembly of Flexible Organic Field-Effect Transistor Arrays Appl. Phys. Express 2010, 3, 051601
42. Liu, C.; Minari, T.; Lu, X.; Kumatani, A.; Takimiya, K.; Tsukagoshi, K. Solution-Processable Organic Single Crystals with Bandlike Transport in Field-Effect Transistors Adv. Mater. 2011, 23, 523-526
43. Uemura, T.; Hirose, Y.; Uno, M.; Takimiya, K.; Takeya, J. Very High Mobility in Solution-Processed Organic Thin-Film Transistors of Highly Ordered [1]Benzothieno[3,2- b ]benzothiophene Derivatives Appl. Phys. Express 2009, 2, 111501
44. Minemawari, H.; Yamada, T.; Matsui, H.; Tsutsumi, J. y.; Haas, S.; Chiba, R.; Kumai, R.; Hasegawa, T. Inkjet printing of single-crystal films Nature 2011, 475, 364-367
45. Haas, S.; Takahashi, Y.; Takimiya, K.; Hasegawa, T. High-performance dinaphtho-thieno-thiophene single crystal field-effect transistors Appl. Phys. Lett. 2009, 95, 022111
46. Uno, M.; Hirose, Y.; Uemura, T.; Takimiya, K.; Nakazawa, Y.; Takeya, J. High-power and high-speed organic three-dimensional transistors with submicrometer channels Appl. Phys. Lett. 2010, 97, 013301
47. McCarthy, M. A.; Liu, B.; Donoghue, E. P.; Kravchenko, I.; Kim, D. Y.; So, F.; Rinzler, A. G. Low-Voltage, Low-Power, Organic Light-Emitting Transistors for Active Matrix Displays Science 2011, 332, 570-573
48. Zschieschang, U.; Ante, F.; Yamamoto, T.; Takimiya, K.; Kuwabara, H.; Ikeda, M.; Sekitani, T.; Someya, T.; Kern, K.; Klauk, H. Flexible Low-Voltage Organic Transistors and Circuits Based on a High-Mobility Organic Semiconductor with Good Air Stability Adv. Mater. 2010, 22, 982-985
49. Ante, F.; Kälblein, D.; Zschieschang, U.; Canzler, T. W.; Werner, A.; Takimiya, K.; Ikeda, M.; Sekitani, T.; Someya, T.; Klauk, H. Contact Doping and Ultrathin Gate Dielectrics for Nanoscale Organic Thin-Film Transistors Small 2011, 1186-1191
50. Kang, M. J.; Miyazaki, E.; Osaka, I.; Takimiya, K.; Nakao, A. Diphenyl Derivatives of Dinaphtho[2,3- b:2′,3′- f ]thieno[3,2- b ]thiophene: Organic Semiconductors for Thermally Stable Thin-Film Transistors ACS Appl. Mater. Interfaces 2013, 5, 2331-2336
51. Yokota, T.; Kuribara, K.; Tokuhara, T.; Zschieschang, U.; Klauk, H.; Takimiya, K.; Sadamitsu, Y.; Hamada, M.; Sekitani, T.; Someya, T. Flexible Low-Voltage Organic Transistors with High Thermal Stability at 250°C Adv. Mater. 2013, 25, 3639-3644
52. Valiyev, F.; Hu, W.-S.; Chen, H.-Y.; Kuo, M.-Y.; Chao, I.; Tao, Y.-T. Synthesis and Characterization of Anthra[2,3- b ]thiophene and Tetraceno[2,3- b ]thiophenes for Organic Field-Effect Transistor Applications Chem. Mater. 2007, 19, 3018-3026
53. -1 Fabricated Using Bis(benzothieno)naphthalene Polycrystalline Films Jpn. J. Appl. Phys. 2013, 52, 05DC11
54. Okamoto, T.; Mitsui, C.; Yamagishi, M.; Nakahara, K.; Soeda, J.; Hirose, Y.; Miwa, K.; Sato, H.; Yamano, A.; Matsushita, T.; Uemura, T.; Takeya, J. V-Shaped Organic Semiconductors With Solution Processability, High Mobility, and High Thermal Durability Adv. Mater. 2013, 25, 6392-6397