DOI QR코드

DOI QR Code

Chain Length Effect of Dialkoxynaphthalene End-Capped Divinylbenzene for OTFT

  • Kim, Ran (Department of Chemistry and RINS, Gyeongsang National University) ;
  • Yun, Hui-Jun (School of Materials Science and Engineering and ERI, Gyeongsang National University) ;
  • Yi, Mi-Hye (Advanced Materials Division, Korea Research Institute of Chemical Technology) ;
  • Shin, Sung-Chul (Department of Chemistry and RINS, Gyeongsang National University) ;
  • Kwon, Soon-Ki (School of Materials Science and Engineering and ERI, Gyeongsang National University) ;
  • Kim, Yun-Hi (Department of Chemistry and RINS, Gyeongsang National University)
  • Received : 2011.10.11
  • Accepted : 2011.11.28
  • Published : 2012.02.20

Abstract

The new organic semiconductors which are composed of divinylbenzene core unit and alkoxynaphthalene on both sides, 1,4-bis-2-(6-octyloxy)naphthalen-2-ylvinylbenzene (BONVB), 1,4-bis-2-(6-decyloxy)naphthalen-2-ylvinylbenzene (BDNVB) and 1,4-bis-2-(6-dodecyloxy)naphthalen-2-ylvinylbenzene (BDDNVB) were synthesized by Wittig reaction. The structures of obtained BONVB, BDNVB and BDDNVB were confirmed by FT-IR and mass spectroscopy. UV-absorption of thin film showed H-aggregates and J-aggregates due to closely packed structure between adjacent molecules. The characterization of vacuum-evaporated films by Xray diffraction (XRD) and atomic force microscopy (AFM) showed that the chain length of alkoxy group affects the crystallinity and morphology. BONVB with octyloxy group showed the mobility of $0.011cm^2/V{\cdot}s$, on/off ratio of $1.31{\times}10^5$, and a subthreshold slope of 0.93 V.

Keywords

References

  1. Horowitz, G. J. Mater. Res. 2004, 19, 1946. https://doi.org/10.1557/JMR.2004.0266
  2. Kelley, T. W.; Baude, P. F.; Gerlach, C.; Ender, D. E.; Muyres, D.; Haase, M. A.; Vogel, D. E.; Theiss, S. D. Chem. Mater. 2004, 16, 4413. https://doi.org/10.1021/cm049614j
  3. Dimitrakopoulos, C. D.; Malenfant, P. R. L. Adv. Mater. 2002, 14, 99. https://doi.org/10.1002/1521-4095(20020116)14:2<99::AID-ADMA99>3.0.CO;2-9
  4. Bao, Z. Adv. Mater. 2000, 12, 227. https://doi.org/10.1002/(SICI)1521-4095(200002)12:3<227::AID-ADMA227>3.0.CO;2-U
  5. Baude, P. F.; Ender, D. A.; Haase, M. A.; Kelley, T. W.; Muyres, D. V.; Theiss, S. D. Appl. Phys. Lett. 2003, 83, 3964.
  6. Blanchet, G. B.; Loo, Y.; Rogers, J. A.; Gao, F.; Fincher, C. R. Appl. Phys. Lett. 2003, 82, 463. https://doi.org/10.1063/1.1533110
  7. Gelinck, G. H.; Huitema, H. E. A.; Van Veenendaal, E.; Cantatore, E.; Schrijnemakers, L.; Van Der Putten, J. B. P. H.; Geuns, T. C. T.; Beenhakkers, M.; Giesbers, J. B.; Huisman, B.; Meijer, E. J.; Benito, E. M.; Touwslager, F. J.; Marsman, A. W.; van Rens, B. J. E.; de Leeuw, D. M. Nat. Mater. 2004, 3, 106. https://doi.org/10.1038/nmat1061
  8. Qiu, Y.; Hu, Y.; Dong, G.; Wang, L.; Xie, J.; Ma, Y. Appl. Phys. Lett. 2003, 83, 1644. https://doi.org/10.1063/1.1604193
  9. Pannemann, C.; Diekmann, T.; Hilleringmann, U. J. Mater. Res. 2004, 19, 1999. https://doi.org/10.1557/JMR.2004.0267
  10. Kim, Y. H.; Jung, H. C.; Kim, S. H.; Yang, K.; Kwon, S. K. Adv. Funct. Mater. 2005, 15, 1799. https://doi.org/10.1002/adfm.200500051
  11. Jang, J. W.; Park, H.; Shin, M. K.; Kang, H. H.; Oh, D. H.; Jung, S. O.; Kwon, S. K.; Kim, Y. H. Dyes and Pigments 2010, 88, 44.
  12. Park, H.; Oh, D. H.; Park, J. W.; Kim, J. H.; Kim, S. C.; Kim, Y. H.; Kwon,S. K. Bull. Korean. Chem. Soc. 2010, 31, 1951. https://doi.org/10.5012/bkcs.2010.31.7.1951
  13. Kim, S. O.; Jung, H. C.; Lee, M. J.; Jun, C.; Kim, Y. H.; Kwon, S. K. J. Polym. Sci. Part A : Polym. Chem. 2009, 47, 5908. https://doi.org/10.1002/pola.23636
  14. So, K. H.; Park, H. T.; Shin, S. C.; Lee, S. G.; Lee, D. H.; Lee, K. H.; Oh, H. Y.; Kwon, S. K.; Kim, Y. H. Bull. Korean. Chem. Soc. 2009, 30, 1611. https://doi.org/10.5012/bkcs.2009.30.7.1611
  15. Park, J. W.; Park, S. J.; Kim, Y. H.; Shin, D. C.; You, H.; Kwon, S. K. Polymer. 2009, 50, 102. https://doi.org/10.1016/j.polymer.2008.10.056
  16. Kim, J. S.; Heo, J.; Kang, P.; Kim, J. H.; Jung, S. O.; Kwon, S. K.; Kim, U. K.; Kim, Y. H. Macromol. Res. 2009, 17, 91. https://doi.org/10.1007/BF03218660
  17. Jang, S. H.; Tai, T. B.; Park, J. H.; Jeong, H. J.; Chun, E. J.; Kim, Y. H.; Lee, S. G.; Singh, O. M.; Yoon, Y. J.; Kwon, S. K. Macromol. Res. 2010, 18, 185. https://doi.org/10.1007/s13233-009-0167-z
  18. Meng, H.; Sun, F.; Goldfinger, M. B.; Jaycox, G. D.; Li, Z.; Marshall, W. J.; Blackman, G. S. J. Am. Chem. Soc. 2005, 127, 2406. https://doi.org/10.1021/ja043189d
  19. Merlo, J. A.; Newman, C. R.; Gerlach, C. P.; Kelley, T. W.; Muyres, D. V.; Fritz, S. E.; Toney, M. F.; Frisbie, C. D. J. Am. Chem. Soc. 2005, 127, 3997. https://doi.org/10.1021/ja044078h
  20. Meng, H.; Bao, Z.; Lovinger, A. J.; Wang, B.-C.; Mujsce, A. M. J. Am. Chem. Soc. 2001, 123, 9214. https://doi.org/10.1021/ja016525o
  21. Videlot-Ackermann, C.; Ackermann, J.; Brisset, H.; Kawamura, K.; Yoshimoto, N.; Yoshimoto, X. P.; El Kassmi, A.; Fages, F. J. Am. Chem. Soc. 2005, 127, 16346. https://doi.org/10.1021/ja054358c
  22. Kim, H. S.; Kim, Y. H.; Kim, T. H.; Noh, Y. Y.; Pyo, S.; Yi, M. H.; Kim, D. Y.; Kwon, S. K. Chem. Mater. 2007, 19, 3561. https://doi.org/10.1021/cm070053g
  23. Zhao, Q.; Kim, T. H.; Park, J. W.; Kim, S. O.; Jung, S. O.; Kim, J. W.; Ahn, T.; Kim, Y. H.; Yi, M. H.; Kwon, S. K. Adv. Mater. 2008, 20, 4868. https://doi.org/10.1002/adma.200800061
  24. Park, S. J.; Kim, S. O.; Jung, S. O.; Yi, M. H.; Kim, Y. H.; Kwon, S. K. J. Electron. Mater. 2009, 38, 2000. https://doi.org/10.1007/s11664-009-0830-3
  25. Lee, M. J.; Kang, M. S.; Shin, M. K.; Park, J. W.; Chung, D. S.; Park, C. E.; Kwon, S. K.; Kim, Y. H. J. Polym. Sci. Part A: Polym. Chem. 2010, 48, 3942. https://doi.org/10.1002/pola.24174
  26. Li, Y.; Kim, T. H.; Zhao, Q.; Kim, E. K.; Han, S. H.; Kim, Y. H.; Jang, J.; Kwon, S. K. J. Polym. Sci. Part A : Polym. Chem. 2008, 46, 5115. https://doi.org/10.1002/pola.22839
  27. Chung, D. S.; Park, J. W.; Kim, S. O.; Heo, K.; Park, C. E.; Ree, M.; Kim, Y. H.; Kwon, S. K. Chem. Mater. 2009, 21, 5499. https://doi.org/10.1021/cm9025057
  28. Videlot-Ackermann, C.; Ackermann, J.; Kawamura, K.; Yoshimoto, N.; Brisset, H.; Raynal, P.; El Kassmi, A.; Fages, F. Org. Electron. 2006, 7, 465. https://doi.org/10.1016/j.orgel.2006.06.005
  29. Jones, B. A.; Ahrens, M. J.; Yoon, M.-H.; Facchetti, A.; Marks, T. J.; Wasielewski, M. R. Angew. Chem. Int. Ed. 2004, 43, 6363. https://doi.org/10.1002/anie.200461324
  30. Sun, Y.; Ma, Y.; Liu, Y.; Lin, Y.; Wang, Z.; Wang, Y.; Di, C.; Xiao, K.; Chen, X.; Qiu, W.; Zhang, B.; Yu, G.; Hu, W.; Zhu, D. Adv. Funct. Mater. 2006, 16, 426. https://doi.org/10.1002/adfm.200500547
  31. Tian, H. K.; Deng, Y. F.; Pan, F.; Huang, L. Z.; Yan, D. H.; Geng, Y. H.; Wang, F. S. J. Mater. Chem. 2010, 20, 7998. https://doi.org/10.1039/c0jm01173h
  32. Jung, B. J.; Lee, K.; Sun, J.; Andreon, A. G.; Katz, H. E. Adv. Funct. Mater. 2010, 20, 2930. https://doi.org/10.1002/adfm.201000655
  33. Kim, C.; Huang, P. Y.; Jhuang, J. W.; Chen, M. C.; Ho, J. C.; Yan, J. Y.; Chen, L. H.; Lee, C. H.; Facchetti, A.; Marks, T. J. Org. Electron. 2010, 11, 1363. https://doi.org/10.1016/j.orgel.2010.04.029
  34. Youn, J.; Chen, M. C.; Liang, Y.; Huang, H.; Ortiz, R. P.; Kim, C.; Stern, C.; Hu, T. S.; Chen, L. H.; Yan, J. Y.; Facchetti, A.; Marks, T. J. Chem. Mater. 2010, 22, 5031. https://doi.org/10.1021/cm101435s
  35. Ahmed, M. O.; Wang, C.; Keg, P.; Pisula, W.; Lam, Y. M.; Ong, B. S.; Ng, S. C.; Chen, Z. K.; Mhaisalkar, S. G. J. Mater. Chem. 2009, 19, 3449. https://doi.org/10.1039/b900979e
  36. Sun, H.; Sun, F.; Goldfinger, M. B.; Jaycox, G. D.; Li, Z.; Marshall, W. J.; Blackman, G. S. J. Am. Chem. Soc. 2005, 127, 2406. https://doi.org/10.1021/ja043189d
  37. Merlo, J. A.; Newman, C. R.; Gerlach, C. P.; Kelley, T. W.; Muyres, D. V.; Fritz, S. E.; Toney, M. F.; Frisbie, C. D. J. Am. Chem. Soc. 2005, 127, 3997. https://doi.org/10.1021/ja044078h
  38. Meng, H.; Bao, Z.; Lovinger, A. J.; Wang, B.-C.; Mujsce, A. M. J. Am. Chem. Soc. 2001, 123, 9214. https://doi.org/10.1021/ja016525o
  39. Videlot-Ackermann, C.; Ackermann, J.; Brisset, H.; Kawamura, K.; Yoshimoto, N.; Yoshimoto, X. P.; El Kassmi, A.; Fages, F. J. Am. Chem. Soc. 2005, 127, 16346. https://doi.org/10.1021/ja054358c
  40. Heeney, M.; Bailey, C.; Genevicius, K.; Shkunov, M.; Sparrowe, D.; Tierney, S.; McCulloch, I. J. Am. Chem. Soc. 2005, 127, 1078. https://doi.org/10.1021/ja043112p
  41. Drolet, N.; Morin, J. F.; Leclerc, N.; Wakin, S.; Tao, Y.; Lecelerc, M. Adv. Funct. Mater. 2005, 15, 1671. https://doi.org/10.1002/adfm.200500168
  42. Janietz, S.; Bradley, D. D. C.; Grell, M.; Giebeler, C.; Inbasekaran, M.; Woo, E. P. Appl. Phys. Lett. 1998, 73, 2453. https://doi.org/10.1063/1.122479
  43. Kim, Y. H.; Lee, D. H.; Park, S. J.; Chen, J.; Yi, M. H.; Kwon, S. K. Journal of Information Display. 2009, 10, 125. https://doi.org/10.1080/15980316.2009.9652095

Cited by

  1. A First Synthesis and Physical Properties of Asymmetric Anthracenes-Thiophenes Bridged with Ethylene vol.33, pp.11, 2012, https://doi.org/10.5012/bkcs.2012.33.11.3810