Abstract
Solution-processed organic semiconductor devices are expected to provide flexible, large-area, light-weight, low-cost, and environment-friendly electronic products for next-generation devices. As small molecular crystals have intrinsically high electrical properties, this chapter focuses on the fabrication technique of single crystalline and polycrystalline organic electronic devices using solution processes. It starts with a description of the relationship between the crystal structure and electrical properties of organic semiconductors. Then, several techniques for preparing single-crystalline organic field effect transistors are discussed. Next, a precursor approach to preparing polycrystalline films is addressed. With this approach, well-soluble and stable precursor compounds are deposited on substrates and then quantitatively converted into target materials by applying external stimuli, such as heat or light. The recent progress of organic field effect transistors and organic photovoltaics with this approach is summarized.
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J.E. Anthony, Angew. Chem. Int. Ed. 47, 452 (2008)
K. Takimiya, S. Shinamura, I. Osaka, E. Miyazaki, Adv. Mater. 23, 4347 (2011)
J. Mei, Y. Diao, A.L. Appleton, L. Fang, Z. Bao, J. Am. Chem. Soc. 135, 6724 (2013)
V. Coropceanu, J. Cornil, D.A. da Silva Filho, Y. Olivier, R. Silbey, J.-L. Brédas, Chem. Rev. 107, 926 (2007)
C.W. Tang, Appl. Phys. Lett. 48, 183 (1986)
M. Hiramoto, H. Fujiwara, M. Yokoyama, Appl. Phys. Lett. 58, 1062 (1991)
G. Yu, J. Gao, J.C. Hummelen, F. Wudl, A.J. Heeger, Science 270, 1789 (1995)
J.-L. Brédas, D. Beljonne, V. Coropceanu, J. Cornil, Chem. Rev. 104, 4971 (2004)
V. Vohra, K. Kawashima, T. Kakara, T. Koganezawa, I. Osaka, K. Takimiya, H. Murata, Nat. Photonics 9, 403 (2015)
S. Blumstengel, S. Sadofev, C. Xu, J. Puls, F. Henneberger, Phys. Rev. Lett. 97, 237401 (2006)
J.E. Anthony, Chem. Rev. 106, 5028 (2006)
M. Watanabe, Y.J. Chang, S.-W. Liu, T.-H. Chao, K. Goto, M.M. Islam, C.-H. Yuan, Y.-T. Tao, T. Shinmyozu, T.J. Chow, Nat. Chem. 4, 574 (2012)
S.C. Capelli, A. Albinati, S.A. Mason, B.T.M. Willis, J. Phys. Chem. A 110, 11695 (2006)
C.P. Brock, J.D. Dunitz, Acta Cryst B46, 795 (1990)
D. Holmes, S. Kumaraswamy, A.J. Matzger, K.P.C. Vollhardt, Chem. Eur. J. 5, 3999 (1999)
V. Coropceanu, O. Kwon, B. Wex, B.R. Kaafarani, N.E. Gruhn, J.C. Durivage, D.C. Neckers, J.-L. Brédas, Chem. Eur. J. 12, 2073 (2006)
O.L. Griffith, J.E. Anthony, A.G. Jones, D.L. Lichtenberger, J. Am. Chem. Soc. 132, 580 (2010)
S.M. Ryno, C. Risko, J.-L. Brédas, J. Am. Chem. Soc. 136, 6421 (2014)
T. Hasegawa, J. Takeya, Sci. Technol. Adv. Mater. 10, 024314 (2009)
A.L. Briseno, S.C.B. Mannsfeld, M.M. Ling, S. Liu, R.J. Tseng, C. Reese, M.E. Roberts, Y. Yang, F. Wudl, Z. Bao, Nature 444, 913 (2006)
J.E. Anthony, J.S. Brooks, D.L. Eaton, S.R. Parkin, J. Am. Chem. Soc. 123, 9482 (2001)
C.D. Sheraw, T.N. Jackson, D.L. Eaton, J.E. Anthony, Adv. Mater. 15, 2009 (2003)
M.M. Payne, S.R. Parkin, J.E. Anthony, C.-C. Kuo, T.N. Jackson, J. Am. Chem. Soc. 127, 4986 (2005)
D.H. Kim, D.Y. Lee, H.S. Lee, W.H. Lee, Y.H. Kim, J.I. Han, K. Cho, Adv. Mater. 19, 678 (2007)
S.K. Park, T.N. Jackson, J.E. Anthony, D.A. Mourey, Appl. Phys. Lett. 91, 063514 (2007)
G. Giri, E. Verploegen, S.C.B. Mannsfeld, S. Atahan-Evrenk, D.H. Kim, S.Y. Lee, H.A. Becerril, A. Aspuru-Guzik, M.F. Toney, Z. Bao, Nature 480, 504 (2011)
Y. Diao, B.C.-K. Tee, G. Giri, J. Xu, D.H. Kim, H.A. Becerril, R.M. Stoltenberg, T.H. Lee, G. Xue, S.C.B. Mannsfeld, Z. Bao, Nat. Mater. 12, 665 (2013)
H. Ebata, T. Izawa, E. Miyazaki, K. Takimiya, M. Ikeda, H. Kuwabara, T. Yui, J. Am. Chem. Soc. 129, 15732 (2007)
T. Izawa, E. Miyazaki, K. Takimiya, Adv. Mater. 20, 3388 (2008)
T. Uemura, Y. Hirose, M. Uno, K. Takimiya, J. Takeya, Appl. Phys. Express 2, 111501 (2009)
J. Soeda, Y. Hirose, M. Yamagishi, A. Nakao, T. Uemura, K. Nakayama, M. Uno, Y. Nakazawa, K. Takimiya, J. Takeya, Adv. Mater. 23, 3309 (2011)
H. Minemawari, T. Yamada, H. Matsui, J. Tsutsumi, S. Haas, R. Chiba, R. Kumai, T. Hasegawa, Nature 475, 364 (2011)
C. Liu, T. Minari, X. Lu, A. Kumatani, K. Takimiya, K. Tsukagoshi, Adv. Mater. 23, 523 (2010)
T. Yamamoto, K. Takimiya, J. Am. Chem. Soc. 129, 2224 (2007)
M.J. Kang, I. Doi, H. Mori, E. Miyazaki, K. Takimiya, M. Ikeda, H. Kuwabara, Adv. Mater. 23, 1222 (2011)
T. Okamoto, C. Mitsui, M. Yamagishi, K. Nakahara, J. Soeda, Y. Hirose, K. Miwa, H. Sato, A. Yamano, T. Matsushita, T. Uemura, J. Takeya, Adv. Mater. 25, 6392 (2013)
C. Mitsui, T. Okamoto, M. Yamagishi, J. Tsurumi, K. Yoshimoto, K. Nakahara, J. Soeda, Y. Hirose, H. Sato, A. Yamano, T. Uemura, J. Takeya, Adv. Mater. 26, 4546 (2014)
S. Sakai, J. Soeda, R. Häusermann, H. Matsui, C. Mitsui, T. Okamoto, M. Ito, K. Hirose, T. Sekiguchi, T. Abe, M. Uno, J. Takeya, Org. Electron. 22, 1 (2015)
Y.S. Yang, T. Yasuda, H. Kakizoe, H. Mieno, H. Kino, Y. Tateyama, C. Adachi, Chem. Commun. 49, 6483 (2013)
H. Mieno, T. Yasuda, Y. Seok, C. Adachi, Chem. Lett. 43, 294 (2014)
J.H. Edwards, W.J. Feast, Polymer 21, 595 (1980)
J.S. Zambounis, Z. Hao, A. Iqbal, Nature 388, 131 (1997)
H. Yamada, T. Okujima, N. Ono, Chem. Commun. 2957 (2008)
M. Watanabe, K.-Y. Chen, Y.J. Chang, T.J. Chow, Acc. Chem. Res. 46, 1606 (2013)
M. Suzuki, T. Aotake, Y. Yamaguchi, N. Noguchi, H. Nakano, K.-I. Nakayama, H. Yamada, J. Photochem. Photobiol. C Photochem. Rev. 18, 50 (2014)
A.R. Brown, A. Pomp, D.M. De Leeuw, D.B.M. Klaassen, E.E. Havinga, P. Herwig, K. Müllen, J. Appl. Phys. 79, 2136 (1996)
P.T. Herwig, K. Müllen, Adv. Mater. 11, 480 (1999)
A. Afzali, C.D. Dimitrakopoulos, T.L. Breen, J. Am. Chem. Soc. 124, 8812 (2002)
A. Afzali, C.D. Dimitrakopoulos, T.O. Graham, Adv. Mater. 15, 2066 (2003)
A. Afzali, C.R. Kagan, G.P. Traub, Synth. Met. 155, 490 (2005)
G.S. Tulevski, Q. Miao, A. Afzali, T.O. Graham, C.R. Kagan, C. Nuckolls, J. Am. Chem. Soc. 128, 1788 (2006)
H. Uno, Y. Yamashita, M. Kikuchi, H. Watanabe, H. Yamada, T. Okujima, T. Ogawa, N. Ono, Tetrahedron Lett. 46, 1981 (2005)
H. Yamada, Y. Yamashita, M. Kikuchi, H. Watanabe, T. Okujima, H. Uno, T. Ogawa, K. Ohara, N. Ono, Chem. Eur. J. 11, 6212 (2005)
S. Katsuta, H. Yamada, T. Okujima, H. Uno, Tetrahedron Lett. 51, 1397 (2010)
S. Katsuta, H. Saeki, K. Tanaka, Y. Murai, D. Kuzuhara, M. Misaki, N. Aratani, S. Masuo, Y. Ueda, H. Yamada, J. Mater. Chem. C 2, 986 (2014)
R. Mondal, B.K. Shah, D.C. Neckers, J. Photochem. Photobiol. A Chem. 192, 36 (2007)
R. Mondal, R.M. Adhikari, B.K. Shah, D.C. Neckers, Org. Lett. 9, 2505 (2007)
R. Mondal, A.N. Okhrimenko, B.K. Shah, D.C. Neckers, J. Phys. Chem. B 112, 11 (2008)
R. Mondal, C. Tönshoff, D. Khon, D.C. Neckers, H.F. Bettinger, J. Am. Chem. Soc. 131, 14281 (2009)
C. Tönshoff, H.F. Bettinger, Angew. Chem. Int. Ed. 49, 4125 (2010)
C. Tönshoff, H.F. Bettinger, Chem. Eur. J. 18, 1789 (2012)
H.F. Bettinger, R. Mondal, M. Krasowska, D.C. Neckers, J. Org. Chem. 78, 1851 (2013)
H. Yamada, C. Ohashi, T. Aotake, S. Katsuta, Y. Honsho, H. Kawano, T. Okujima, H. Uno, N. Ono, S. Seki, K.-I. Nakayama, Chem. Commun. 48, 11136 (2012)
C. Ohashi, H. Yamada, K. Nakayama, Mol. Cryst. Liq. Cryst. 580, 103 (2013)
S. Masuo, K. Tanaka, M. Oe, H. Yamada, Phys. Chem. Chem. Phys. 16, 13483 (2014)
C. Quinton, M. Suzuki, Y. Kaneshige, Y. Tatenaka, C. Katagiri, Y. Yamaguchi, D. Kuzuhara, N. Aratani, K.-I. Nakayama, H. Yamada, J. Mater. Chem. C 3, 5995 (2015)
K.-I. Nakayama, C. Ohashi, Y. Oikawa, T. Motoyama, H. Yamada, J. Mater. Chem. C 1, 6244 (2013)
K.-Y. Chen, H.-H. Hsieh, C.-C. Wu, J.-J. Hwang, T.J. Chow, Chem. Commun., 1065 (2007)
R.A. Laudise, C. Kloc, P.G. Si, pkins, and T. Siegrist. J. Crysst. Growth 187, 449 (1998)
J. Soeda, T. Okamoto, A. Hamaguchi, Y. Ikeda, H. Sato, A. Yamano, J. Takeya, Org. Electron. 14, 1211 (2013)
M. Uno, Y. Tominari, M. Yamagishi, I. Doi, E. Miyazaki, K. Takimiya, J. Takeya, Appl. Phys. Lett. 94, 223308 (2009)
Y. Kimura, T. Nagase, T. Kobayashi, A. Hamaguchi, Y. Ikeda, T. Shiro, K. Takimiya, H. Naito, Adv. Mater. 27, 727 (2014)
A. Hamaguchi, T. Negishi, Y. Kimura, Y. Ikeda, K. Takimiya, S.Z. Bisri, Y. Iwasa, T. Shiro, Adv. Mater. 27, 6606 (2015)
W. Li, M. Yi, H. Ling, F. Guo, T. Wang, T. Yang, L. Xie, W. Huang, J. Phys. D: Appl. Phys. 49, 125104 (2016)
C.M.B. Carvalho, T.J. Brocksom, K.T. de Oliveira, Chem. Soc. Rev. 42, 3302 (2013)
S.-D. Jeong, B. Min, S.Y. Cho, C. Lee, B.K. Park, K.-S. An, J. Lim, J. Org. Chem. 77, 8329 (2012)
T. Okujima, Y. Hashimoto, G. Jin, H. Yamada, H. Uno, N. Ono, Tetrahedron 64, 2405 (2008)
S. Aramaki, Y. Sakai, N. Ono, Appl. Phys. Lett. 84, 2085 (2004)
S. Ito, T. Murashima, N. Ono, H. Uno, Chem. Commun., 1661 (1998)
S. Aramaki, J. Mizuguchi, Acta Cryst B59, o1556 (2003)
N. Noguchi, S. Junwei, H. Asatani, M. Matsuoka, Cryst. Growth Des. 10, 1848 (2010)
P.B. Shea, J. Kanicki, J. Appl. Phys. 111, 073709 (2012)
P.B. Shea, J. Kanicki, N. Ono, J. Appl. Phys. 98, 014503 (2005)
P.B. Shea, J. Kanicki, L.R. Pattison, P. Petroff, M. Kawano, H. Yamada, N. Ono, J. Appl. Phys. 100, 034502 (2006)
P.B. Shea, C. Chen, J. Kanicki, L.R. Pattison, P. Petroff, H. Yamada, N. Ono, Appl. Phys. Lett. 90, 233107 (2007)
P.B. Shea, L.R. Pattison, M. Kawano, C. Chen, J. Chen, P. Petroff, D.C. Martin, H. Yamada, N. Ono, J. Kanicki, Synth. Met. 157, 190 (2007)
H. Yamada, K. Kushibe, T. Okujima, H. Uno, N. Ono, Chem. Commun., 383 (2006)
H. Yamada, K. Kushibe, S. Mitsuogi, T. Okujima, H. Uno, N. Ono, Tetrahedron Lett. 49, 4731 (2008)
K. Takahashi, D. Kuzuhara, N. Aratani, H. Yamada, J. Photopolym. Sci. Tech. 26, 213 (2013)
K. Takahashi, N. Yamada, D. Kumagai, D. Kuzuhara, M. Suzuki, Y. Yamaguchi, N. Aratani, K. Nakayama, H. Yamada, J. Porphyrins Phthalocyanines 19, 465 (2015)
K. Takahashi, B. Shan, X. Xu, S. Yang, T. Koganezawa, D. Kuzuhara, N. Aratani, M. Suzuki, Q. Miao, H. Yamada, ACS Appl. Mater. Interfaces 9, 8211 (2017)
D. Liu, X. Xu, Y. Su, Z. He, J. Xu, Q. Miao, Angew. Chem. Int. Ed. 52, 6222 (2013)
D. Liu, Z. He, Y. Su, Y. Diao, S.C.B. Mannsfeld, Z. Bao, J. Xu, Q. Miao, Adv. Mater. 26, 7190 (2014)
A.R. Murphy, J.M.J. Fréchet, P. Chang, J. Lee, V. Subramanian, J. Am. Chem. Soc. 126, 1596 (2004)
A.R. Murphy, P.C. Chang, P. VanDyke, J. Liu, J.M.J. Fréchet, V. Subramanian, D.M. DeLongchamp, S. Sambasivan, D.A. Fischer, E.K. Lin, Chem. Mater. 17, 6033 (2005)
D.M. DeLongchamp, S. Sambasivan, D.A. Fischer, E.K. Lin, P. Chang, A.R. Murphy, J.M.J. Fréchet, V. Subramanian, Adv. Mater. 17, 2340 (2005)
T. Akiyama, A. Hirao, T. Okujima, H. Yamada, H. Uno, N. Ono, Heterocycles 74, 835 (2007)
A. Hirao, T. Akiyama, T. Okujima, H. Yamada, H. Uno, Y. Sakai, S. Aramaki, N. Ono, Chem. Commun., 4714 (2008)
M. Guide, J.D.A. Lin, C.M. Proctor, J. Chen, C. García-Cervera, T.-Q. Nguyen, J. Mater. Chem. A 2, 7890 (2014)
Y. Matsuo, A. Iwashita, Y. Abe, C.-Z. Li, K. Matsuo, M. Hashiguchi, E. Nakamura, J. Am. Chem. Soc. 130, 15429 (2008)
Y. Matsuo, Y. Sato, T. Niinomi, I. Soga, H. Tanaka, E. Nakamura, J. Am. Chem. Soc. 131, 16048 (2009)
Y. Tamura, H. Saeki, J. Hashizume, Y. Okazaki, D. Kuzuhara, M. Suzuki, N. Aratani, H. Yamada, Chem. Commun. 50, 10379 (2014)
H. Tamura, Y. Matsuo, Chem. Phys. Lett. 598, 81 (2014)
M. Guide, X.-D. Dang, T.-Q. Nguyen, Adv. Mater. 23, 2313 (2011)
Y. Zhen, H. Tanaka, K. Harano, S. Okada, Y. Matsuo, E. Nakamura, J. Am. Chem. Soc. 137, 2247 (2015)
M.D. Perez, C. Borek, S.R. Forrest, M.E. Thompson, J. Am. Chem. Soc. 131, 9281 (2009)
J.L. Segura, N. Martín, D.M. Guldi, Chem. Soc. Rev. 34, 31 (2005)
M. Wang, F. Wudl, J. Mater. Chem. 22, 24297 (2012)
H. Imahori, T. Umeyama, K. Kurotobi, Y. Takano, Chem. Commun. 48, 4032 (2012)
Y. Tamura, D. Kuzuhara, M. Suzuki, H. Hayashi, N. Aratani, H. Yamada, J. Mater. Chem. A 4, 15333 (2016)
K. Takahashi, D. Kumagai, N. Yamada, Y. Yamaguchi, T. Koganezawa, D. Kuzuhara, M. Suzuki, N. Aratani, S. Masuo, K.-I. Nakayama, and H. Yamada, Proceeding of International Conference on Hybrid and Organic Photovoltaics (HOPV2016) (2016)
T. Motoyama, T. Kiyota, H. Yamada, K.-I. Nakayama, Solar Energy Mater. Sol. Cells 114, 156 (2013)
H. Yamada, Y. Yamaguchi, R. Katoh, T. Motoyama, T. Aotake, D. Kuzuhara, M. Suzuki, T. Okujima, H. Uno, N. Aratani, K. Nakayama, Chem. Commun. 49, 11638 (2013)
Y. Yamaguchi, M. Suzuki, T. Motoyama, S. Sugii, C. Katagiri, K. Takahira, S. Ikeda, H. Yamada, K.-I. Nakayama, Sci. Rep. 4, 7151 (2014)
M. Suzuki, Y. Yamaguchi, K. Uchinaga, K. Takahira, C. Quinton, S. Yamamoto, N. Nagami, M. Furukawa, K. Nakayama, H. Yamada, Chem. Sci. 9, 6614 (2018). https://doi.org/10.1039/C8SC01799A
D. Kuzuhara, J. Mack, H. Yamada, T. Okujima, N. Ono, N. Kobayashi, Chem. Eur. J. 15, 10060 (2009)
H. Saeki, O. Kurimoto, M. Misaki, D. Kuzuhara, H. Yamada, Y. Ueda, Appl. Phys. Express 6, 035601 (2013)
H. Saeki, M. Misaki, D. Kuzuhara, H. Yamada, Y. Ueda, Jpn. J. Appl. Phys. 52, 111601 (2013)
Y. Kikukawa, T. Fukuda, A. Fuyuhiro, N. Ishikawa, N. Kobayashi, Chem. Commun. 47, 8518 (2011)
H. Wang, N. Su, L.-C. Wang, X. Wu, S. Bui, A. Nielsen, H.-T. Vo, Y. Luo, X.-J. Ma, Methods Mol. Biol. 1211, 139 (2014)
T.L. Chen, J.J.-A. Chen, L. Catane, B. Ma, Org. Electron. 12, 1126 (2011)
J.K. Lee, Y.-M. Wang, S. Cho, F. Wudl, A.J. Heeger, Org. Electron. 10, 1223 (2009)
T. Umeyama, S. Shibata, H. Imahori, RSC Adv. 6, 83758 (2016)
K. Kawajiri, T. Kawanoue, M. Yamato, K. Terai, M. Yamashita, M. Furukawa, N. Aratani, M. Suzuki, K. Nakayama, H. Yamada, ECS J. Solid State Sci. Technol. 6, M3068 (2017)
Acknowledgment
This work was supported by CREST, Japan Science and Technology Agency (JST), Grants-in-Aid for Scientific Research (Nos. 16H02286, 26105004, 26620167), and the Program for Promoting the Enhancement of Research Universities in NAIST sponsored by the Ministry of Education, Culture, Sports, Science and Technology (MEXT), Japan.
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Yamada, H. (2019). Nanostructure Control of Crystalline Organic Thin Films by Solution Processes. In: Kubozono, Y. (eds) Physics and Chemistry of Carbon-Based Materials. Springer, Singapore. https://doi.org/10.1007/978-981-13-3417-7_9
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