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Synthetic Aspects of Organic Semiconductors

Published online by Cambridge University Press:  31 January 2011

John E. Anthony ,
Martin Heeney  and
Beng S. Ong
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Abstract

This article discusses the importance of the choice of synthetic methodology in the purity, and therefore performance, of both small-molecule and polymeric organic semiconductors. We discuss common methodologies used in the preparation of organic semiconductors, paying particular attention to the impurities and by-products that can arise during these synthetic approaches and how they can have an impact on semiconductor performance.

Type
Research Article
Information
MRS Bulletin , Volume 33 , Issue 7: Commercialization of Organic Electronics , July 2008 , pp. 698 - 705
Copyright
Copyright © Materials Research Society 2008

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References

1.Facchetti, A., Mater. Today 10, 28 (2007).CrossRefGoogle Scholar
2.Würthner, F., Schmidt, R., Chem. Phys. Chem. 7, 793 (2006).Google Scholar
3.Witte, G., Wöll, C., J. Mater. Res. 19, 1889 (2004).Google Scholar
4.Kelley, T.W., Baude, P.F., Gerlach, C., Ender, D.E., Muyres, D., Haase, D., Vogel, D.E., Theiss, S.D., Chem. Mater. 16, 4413 (2004).CrossRefGoogle Scholar
5.Katz, H.E., Chem. Mater. 16, 4748 (2004).CrossRefGoogle Scholar
6.Bendikov, M., Wudl, F., Perepichka, D.F., Chem. Rev. 104, 4891 (2004).Google Scholar
7.Anthony, J.E., Chem. Rev. 106, 5028 (2006).CrossRefGoogle Scholar
8.Park, Y.D., Lim, J.A., Lee, H.S., Cho, K., Mater. Today 10, 46 (2007).Google Scholar
9.Reese, C., Roberts, M., Ling, M.-M., Bao, Z., Mater. Today 7, 20 (2004).Google Scholar
10.Murphy, A.R., Fréchet, J.M.J., Chem. Rev. 107, 1066 (2007).Google Scholar
11.Reese, C., Bao, Z., J. Mater. Chem. 16, 329 (2006).Google Scholar
12.de Boer, R.W.I., Gershenson, M.E., Morpurgo, A.F., Podzorov, V., Phys. Status Solidi A 201, 1302 (2004).Google Scholar
13.Anthony, J.E., Angew. Chem., Int. Ed. 47, 452 (2008).Google Scholar
14.Kawase, T., Shimoda, T., Newsome, C., Sirringhaus, H., Friend, R.H., Thin Solid Films 438–439, 279 (2003).Google Scholar
15.Probst, K.H., Karl, N., Phys. Status Solidi A 27, 499 (1975).CrossRefGoogle Scholar
16.Garnier, F., Peng, X., Horowitz, G., Fichou, D., Mol. Eng. 1, 131 (1991).Google Scholar
17.Rep, D.B.A., Morpurgo, A.F., Sloof, W.G., Klapwijk, T.M., J. Appl. Phys. 93, 2082 (2003).Google Scholar
18.Pflaum, J., Niemax, J., Tripathi, A.K., Chem. Phys. 325, 152 (2006), and references therein.Google Scholar
19.Kotha, S., Lahiri, K., Kashinath, D., Tetrahedron 58, 9633 (2002).CrossRefGoogle Scholar
20.Donat-Bouillud, A., Lévesque, I., Tao, Y., D'Iorio, M., Beaupre, S., Blondin, P., Ranger, M., Bouchard, J., Leclerc, M., Chem. Mater. 12, 1931 (2000).CrossRefGoogle Scholar
21.Yamamoto, T., Hayashi, Y., Yamamoto, A., Bull. Chem. Soc. Jpn. 51, 2091 (1978).Google Scholar
22.Rehahn, M., Schlüter, A.-D., Wegner, G., Feast, W. J., Polymer 30, 1054 (1989).Google Scholar
23.Lére-Porte, J.-P., Moreau, J.J.E., Torreilles, C., Eur. J. Org. Chem. 1249 (2001).3.0.CO;2-F>CrossRefGoogle Scholar
24.Dhanabalan, A., van Dongen, J.L.J., van Duren, J.K.J., Janssen, H.M., van Hal, P.A., Janssen, R.A.J., Macromolecules 34, 2495 (2001).Google Scholar
25.Farina, V., Krishnamurthy, V., Scott, W.J., Org. React. 50, 1 (1998).Google Scholar
26.King, A.O., Okukado, N., Negishi, E.-I., J. Chem. Soc., Chem. Commun. 683 (1977).Google Scholar
27.Wang, F., Wilson, M.S., Rauh, R.D., Schottland, P., Reynolds, J.R., Macromolecules 32, 4272 (1999).CrossRefGoogle Scholar
28.Facchetti, A., Mushrush, M., Katz, H.E., Marks, T.J., Adv. Mater. 15, 33 (2003).Google Scholar
29.Facchetti, A., Yoon, M.-H., Stern, C.L., Hutchison, G.R., Ratner, M.A., Marks, T.J., J. Am. Chem. Soc. 126, 13480 (2004).Google Scholar
30.Locklin, J., Li, D., Mannsfeld, S.C.B., Borkent, E.-J., Meng, H., Advincula, R., Bao, Z., Chem. Mater. 17, 3366 (2005).Google Scholar
31.Krebs, F.C., Nyberg, R.B., Jorgensen, M., Chem. Mater. 16, 1313 (2004).Google Scholar
32.Nielsen, K.T., Bechgaard, K., Krebs, F.C., Macromoecules 38, 658 (2005).Google Scholar
33.Katz, H.E., Dodabalapur, A., Torsi, L., Elder, D., Chem. Mater. 7, 2238 (1995).CrossRefGoogle Scholar
34.Katz, H.E., Laqiundanum, J.G., Lovinger, A.J., Chem. Mater. 10, 633 (1998).CrossRefGoogle Scholar
35.Reid, W., Anthofer, F., Angew. Chem. 60, 604 (1954).Google Scholar
36.De la Cruz, P., Martin, N., Miguel, F., Seoane, C., Albert, A., Cano, H., Gonzalez, A., Pingarron, J.M., J. Org. Chem. 57, 6192 (1992).CrossRefGoogle Scholar
37.Cava, M.P., Napier, D.R., J. Am. Chem. Soc. 79, 1701 (1957).CrossRefGoogle Scholar
38.Bendikov, M., Wudl, F., Perepichka, F., Chem. Rev. 104, 4891 (2004) and references therein.Google Scholar
39.Miller, G.P., Mack, J., Briggs, J., Proc. Electrochem. Soc. 11, 202 (2001).Google Scholar
40.Tang, M.L., Okamoto, T., Bao, Z., J. Am. Chem. Soc. 128, 16002 (2006).Google Scholar
41.Wilds, A.L., Org. React. 2, 178 (1944).Google Scholar
42.Goodings, E.P., Mitchard, D.A., Owen, G., J. Chem. Soc., Perkin Trans. 1 11, 1310 (1972).Google Scholar
43.Roberson, L.B., Kowalik, J., Tolbert, L.M., Kloc, C., Zeis, R., Chi, X., Fleming, R., Wilkins, C., J. Am. Chem. Soc. 127, 3069 (2005).Google Scholar
44.Reddy, A.R., Bendikov, M., Chem. Commun. 1179 (2006).CrossRefGoogle Scholar
45.Jurchescu, O.D., Baas, J., Palstra, T.T.M., Appl. Phys. Lett. 84, 3061 (2004).Google Scholar
46.Jurchescu, O.D., Popinciuc, M., van Wees, B.J., Palstra, T.T.M., Adv. Mater. 19, 688 (2007).Google Scholar
47.Zeis, R., Besnard, C., Siegrist, T., Schlockermann, C., Chi, X., Kloc, C., Chem. Mater. 18, 244 (2006).Google Scholar
48.Yamamoto, T., Takimiya, K., J. Am. Chem. Soc. 129, 2224 (2007).CrossRefGoogle Scholar
49.Takimiya, K., Kunugi, Y., Konda, Y., Ebata, H., Toyoshima, Y., Otsubo, T., J. Am. Chem. Soc. 128, 3044 (2006).CrossRefGoogle Scholar
50.Ebata, H., Izawa, T., Miyazaki, E., Takimiya, K., Ikeda, M., Kuwabara, H., Yui, T., J. Am. Chem. Soc. 129, 15732 (2007).Google Scholar
51.Ebata, H., Miyazaki, E., Yamamoto, T., Takimiya, K., Org. Lett. 9, 4499 (2007).Google Scholar
52.Landis, C.A., Payne, M.M., Eaton, D.L., Anthony, J.E., J. Am. Chem. Soc. 126, 1338 (2004).Google Scholar
53.Allen, C.F.H., Bell, A., J. Am. Chem. Soc. 64, 1253 (1942).CrossRefGoogle Scholar
54.Vets, N., Smet, M., Dehaen, W., Synth. Lett. 217 (2005).Google Scholar
55.Wolak, M.A., Jang, B.-B., Palilis, L.C., Kafafi, Z., J. Phys. Chem. B 108, 5492 (2004).Google Scholar
56.Miao, Q., Chi, X., Xiao, S., Zeis, R., Lefenfeld, M., Siegrist, T., Steigerwald, M.L., Nuckolls, C.J., J. Am. Chem. Soc. 128, 1340 (2006).Google Scholar
57.Maulding, D.R., Roberts, B.G., J. Org. Chem. 34, 1734 (1969).Google Scholar
58.Miller, G.P., Mack, J., Briggs, J., Proc. Electrochem. Soc. 11, 2001 (2001).Google Scholar
59.Anthony, J.E., Brooks, J.S., Eaton, D.L., Parkin, S.R., J. Am. Chem. Soc. 123, 9482 (2001).Google Scholar
60.Schmidt, R., Göttling, S., Leusser, D., Stalke, D., Krause, A.-M., Würthner, F., J. Mater. Chem. 16, 3708 (2006).Google Scholar
61.Park, S.K., Jackson, T.N., Anthony, J.E., Mourey, D.A., Appl. Phys. Lett. 91, 063514 (2007).Google Scholar
62.Kim, D.H., Lee, D.Y., Lee, H.S., Lee, W.H., Kim, Y.H., Han, J.I., Cho, K., Adv. Mater. 19, 678 (2007).Google Scholar
63.Chen, J., Subramanian, S., Parkin, S.R., Siegler, M., Gallup, K., Haughn, C., Martin, D.C., Anthony, J.E., J. Mater. Chem. 18, 1961 (2008).Google Scholar
64.Sirringhaus, H., Friend, R.H., Wang, C., Leuninger, J., Mullen, K., J. Mater. Chem. 9, 2095 (1999).Google Scholar
65.Laquindanum, J.G., Katz, H.E., Lovinger, A.J., J. Am. Chem. Soc. 120, 664 (1998).Google Scholar
66.Payne, M.M., Parkin, S.R., Anthony, J.E., Kuo, C.C., Jackson, T.N., J. Am. Chem. Soc. 127, 4986 (2005).Google Scholar
67.Subramanian, S., Park, S.K., Parkin, S.R., Podzorov, V., Jackson, T.N., Anthony, J.E., J. Am. Chem. Soc. 130, 2706 (2008).CrossRefGoogle Scholar
68.Würthner, F., Stepanenko, V., Chen, Z., Saha-Möller, C.R., Kocher, N., Stalke, D., J. Org. Chem. 69 7933 (2004).Google Scholar
69.Jones, B.A., Facchetti, A., Wasielewski, M.R., Marks, T.J., J. Am. Chem. Soc. 129, 15259 (2007).Google Scholar
70.Jones, B.A., Ahrens, M.J., Yoon, M.-H., Facchetti, A., Marks, T.J., Wasielewski, M.R., Angew. Chem., Int. Ed. 43, 6363 (2004).CrossRefGoogle Scholar
71.Kline, J.R., McGehee, M.D., Kadnikova, E.N., Liu, J., Frechet, J.M.J., Adv. Mater. 15, 1519 (2003).Google Scholar
72.Kline, R.J., McGehee, M.D., Kadnikova, E.N., Liu, J., Frechet, J.M.J., Toney, M.F., Macromolecules 38, 3312 (2005).Google Scholar
73.Zen, A., Pflaum, J., Hirschmann, S., Zhuang, W., Jaiser, F., Asawapirom, U., Rabe, J.P., Scherf, U., Neher, D., Adv. Funct. Mater. 14, 757 (2004).Google Scholar
74.Pokrop, R., Verilhac, J.-M., Gasior, A., Wielgus, I., Zagorska, M., Travers, J.-P., Pron, A., J. Mater. Chem. 16, 3099 (2006).Google Scholar
75.Verilhac, J.-M., Pokrop, R., LeBlevennec, G., Kulszewicz-Bajer, I., Buga, K., Zagorska, M., Sadki, S., Pron, A., J. Phys. Chem. B 110, 13305 (2006).Google Scholar
76.Chang, J.-F., Clark, J., Zhao, N., Sirringhaus, H., Breiby, D.W., Andreasen, J.W., Nielsen, M.M., Giles, M., Heeney, M., McCulloch, I., Phys. Rev. B 74, 115318/1 (2006).CrossRefGoogle Scholar
77.Brinkmann, M., Rannou, P., Adv. Funct. Mater. 17, 101 (2007).CrossRefGoogle Scholar
78.Olsen, B.D., Jang, S.Y., Luning, J.M., Segalman, R.A., Macromolecules 39, 4469 (2006).CrossRefGoogle Scholar
79.Urien, M., Wantz, G., Cloutet, E., Hirsch, L., Tardy, P., Vignau, L., Cramail, H., Parniex, J.P., Org. Electron. 8, 727 (2007).Google Scholar
80.Sonar, P., Grimsdale, A.C., Heeney, M., Shkunov, M., McCulloch, I., Mullen, K., Synth. Met. 157, 872 (2007).CrossRefGoogle Scholar
81.Garrett, C.E., Prasad, K., Adv. Synth. Catal. 346, 889 (2004).Google Scholar
82.Kulkarni, A.P., Kong, X., Jenekhe, S.A., J. Phys. Chem. B 108, 8689 (2004).Google Scholar
83.Chi, C., Im, C., Enkelmann, V., Ziegler, A., Lieser, G., Wegner, G., Chem. Eur. J. 11, 6833 (2005).Google Scholar
84.List, E.J.W., Guentner, R., Scandiucci de Freitas, P., Scherf, U., Adv. Mater. 14, 374 (2002).Google Scholar
85.McCullough, R., Adv. Mater. 10, 93 (1998).Google Scholar
86.Pron, A., Rannou, P., Prog. Polym. Sci. 27, 135 (2002).CrossRefGoogle Scholar
87.Chan, H.S.O., Ng, S.C., Prog. Polym. Sci. 23, 1167 (1998).Google Scholar
88.Waltman, R.J., Bargon, J., Diaz, A.F., J. Phys. Chem. 87, 1459 (1983).Google Scholar
89.Barbarella, G., Zambianchi, M., Di Toro, R., Colonna, M. Jr, Iarossi, D., Goldoni, F., Bongini, A., J. Org. Chem. 61, 8285 (1996).Google Scholar
90.Wei, Y., Chan, C.-C., Tian, J., Jang, G.W., Hsueh, K.F., Chem. Mater. 3, 888 (1991).Google Scholar
91.Roncali, J., Chem. Rev. 92, 711 (1992).Google Scholar
92.Engelmann, G., Jugelt, W., Kossmehl, G., Welzel, H.-P., Tschuncky, P., Heinze, J., Macromolecules 29, 3370 (1996).Google Scholar
93.Lere-Porte, J.-P., Moreau, J.J.E., Sauvajol, J.-L., J. Organomet. Chem 521, 11 (1996).Google Scholar
94.Leclerc, M., Diaz, F.M., Wegner, G., Makromol. Chem. 190, 3105 (1989).Google Scholar
95.Amou, S., Haba, O., Shirato, K., Hayakaw, T., Ueda, M., Takeuchi, K., Asai, M., J. Polym. Sci. A: Polym. Chem. 37, 1943 (1999).Google Scholar
96.Andreani, F., Salatelli, E., Lanzi, M., Bertinelli, F., Fichera, A.M., Gazzano, M., Polymer 41, 3147 (2000).Google Scholar
97.Ng, S.-C.; Ong, T.-T., Chan, H.S.O., J. Mater. Chem. 8, 2663 (1998).Google Scholar
98.Ong, B.S., Wu, Y., Jiang, L., Murti, K., Synth. Met. 142, 49 (2004).Google Scholar
99.Ong, B.S., Wu, Y., Liu, P., Gardner, S., J. Am. Chem. Soc. 126, 3378 (2004).Google Scholar
100.Abdou, M.S.A., Orfino, F.P., Son, Y., Holdcroft, S., J. Am. Chem. Soc. 119, 4518 (1997).CrossRefGoogle Scholar
101.Abdou, M.S.A., Lu, X., Xie, Z.W., Orfino, F., Deen, M.J., Holdcroft, S., Chem. Mater. 7, 631 (1995).Google Scholar
102.Gurunathan, K., Murugan, A.V., Marimuthu, R., Mulik, U.P., Amalnerkar, D.P., Mater. Chem. Phys. 61, 173 (1999).Google Scholar
103.Yamamoto, T., Morita, A., Miyazaki, Y., Maruyama, T., Wakayama, H., Zhou, Z., Nakamura, Y., Kanbara, T., Sasaki, S., Kubota, K., Macromolecules 25, 1214 (1992).Google Scholar
104.Kokubo, H., Sato, T., Yamamoto, T., Macromolecules 3959 (2006).Google Scholar
105.Yamamoto, T., J. Organomet. Chem. 653, 195 (2002).CrossRefGoogle Scholar
106.McCullough, R.D., Lowe, R.D., Chem. Commun. 70 (1992).Google Scholar
107.Loewe, R.S., Khersonsky, S.M., McCullough, R.D., Adv. Mater. 11, 250 (1999).Google Scholar
108.Bolognesi, A., Porzio, W., Bajo, G., Zannoni, G., Fannig, L., Acta Polym. 50, 151 (1999).Google Scholar
109.Chen, T.-A., Rieke, R.D., J. Am. Chem. Soc. 114, 10087 (1992).Google Scholar
110.Chen, T.-A., Wu, X., Rieke, R.D., J. Am. Chem. Soc. 117, 233 (1995).Google Scholar
111.Liversedge, I. A., Higgins, S.J., Giles, M., Heeney, M., McCulloch, I., Tetrahedron Lett. 47, 5143 (2006).Google Scholar
112.Jayakannan, M., van Dongen, J.L.J., Janssen, R.A.J., Macromolecules 34, 5386 (2001).Google Scholar
113.Loewe, R.S., Ewbank, P.C., Liu, J., Zhai, L., McCullough, R.D., Macromolecules 34, 4324 (2001).Google Scholar
114.Schluter, A.D., J. Polym. Sci. A: Polym. Chem. 39, 153383 (2001).Google Scholar
115.Bao, Z., Chan, W.K., Yu, L., J. Am. Chem. Soc. 117, 12426 (1995).Google Scholar
116.Loewe, R.S., Ewbank, P.C., Liu, J., Zhai, L., McCullough, R.D., Macromolecules 34, 4324 (2001).Google Scholar
117.Tierney, S., Heeney, M., McCulloch, I., Synth. Met. 148, 195 (2005).Google Scholar
118.Goodson, F.E., Wallow, T.I., Novak, B.M., Macromolecules 31, 2047 (1998).Google Scholar
119.Miyakoshi, R., Yokoyama, A., Yokozawa, T., J. Am. Chem. Soc. 127, 17542 (2005).Google Scholar
120.Yokoyama, A., Miyakshi, R., Yokozawa, T., Macromolecules (2004).Google Scholar
121.Sheina, E.E., Liu, J., Iovu, M.C., Laird, D.W., McCullough, R.D., Macromolecules 37, 3526 (2004).Google Scholar
122.Yokoyama, A., Suzuki, H., Kubota, Y., Ohuchi, K., Higashimura, H., Yokozawa, T., J. Am. Chem. Soc. 129, 7236 (2007).Google Scholar
123.Radano, C.P., Scherman, O.A., Stingelin-Stutzmann, N., Mueller, C., Breiby, D.W., Smith, P., Janssen, R.A.J., Meijer, E.W., J. Am. Chem. Soc. 127, 12502 (2005).Google Scholar
124.Jinsong Liu, E.S., Kowalewski, T., McCullough, R.D., Angew. Chem. 114, 339 (2002).Google Scholar
125.Muller, C., Goffri, S., Breiby, D.W., Andreasen, J.W., Chanzy, H.D., Janssen, R.A.J., Nielsen, M.M., Radano, C.P., Sirringhaus, H., Smith, P., Stingelin-Stutzmann, N., Adv. Funct. Mater. 17, 2674 (2007).Google Scholar