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Oxoammonium cation of 2,2,6,6-tetramethylpiperidin-1-oxyl: a very efficient dopant for hole-transporting triaryl amines in a perovskite solar cell

Published online by Cambridge University Press:  29 January 2018

H. Maruo
Affiliation:
Department of Applied Chemistry, Waseda University, Tokyo 169-8555, Japan
S. Tanaka
Affiliation:
Department of Applied Chemistry, Waseda University, Tokyo 169-8555, Japan
M. Takamura
Affiliation:
Department of Applied Chemistry, Waseda University, Tokyo 169-8555, Japan
K. Oyaizu
Affiliation:
Department of Applied Chemistry, Waseda University, Tokyo 169-8555, Japan
H. Segawa
Affiliation:
Research Center for Advanced Science and Technology, The University of Tokyo, Tokyo 153-8904, Japan
H. Nishide*
Affiliation:
Department of Applied Chemistry, Waseda University, Tokyo 169-8555, Japan
*
Address all correspondence to H. Nishide at nishide@waseda.jp
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Abstract

Oxoammonium cation of 2,2,6,6-tetramethylpiperidin-1-oxyl (TEMPO) was used as an oxidizing dopant of triaryl amines to efficiently and almost quantitatively generate radical cations of the amines or a hole carrier. The doped-triaryl amines yielded an amorphous and homogeneous layer without any residual oxidant or neutral TEMPO molecule through its sublimination or warming the layer. The TEMPO cation-doped spiro-OMeTAD [tetrakis(dimethoxyphenylamine)spirobifluorene] produced a high hole mobility of 2 × 10−4 cm2/Vs. The perovskite solar cell fabricated with the TEMPO cation-doped or residual dopant-free spiro-OMeTAD as the hole-transporting layer displayed a photo-conversion efficiency of 20.1% with durability.

Type
Research Letters
Copyright
Copyright © Materials Research Society 2018 

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References

1. Oyaizu, K. and Nishide, H.: Biology and materials. In Encyclopedia of Radicals in Chemistry, edited by Chatgilialoglu, C. and Studer, A. (John Wiley & Sons, New York, 2012), pp. 2163–2170.Google Scholar
2. Isogai, A., Saito, T., and Fukuzumi, H.: TEMPO-oxidized cellulose nanofibers. Nanoscale 3, 71 (2011).Google Scholar
3. Iwabuchi, Y.: Discovery and exploitation of AZADO: the highly active catalyst for alcohol oxidation. Chem. Pharm. Bull. 61, 1197 (2013).Google Scholar
4. Hawker, C.J., Bosman, A.W., and Harth, E.: New polymer synthesis by nitroxide mediated living radical polymerizations. Chem. Rev. 101, 3661 (2001).Google Scholar
5. Otsuka, H.: Reorganization of polymer structures based on dynamic covalent chemistry: polymer reactions by dynamic covalent exchanges of alkoxyamine units. Polymer 45, 879 (2013).Google Scholar
6. Nishide, H. and Suga, T.: Magnetic polymer. In Encyclopedia of Polymer Science and Technology, 4th ed., edited by Matyjaszewski, K. (John Wiley & Sons, New York, 2012). doi: 10.1002/0471440264.pst433.pub2.Google Scholar
7. Seber, G., Freitas, R.S., Mague, J.T., Filho, A.P., Gratens, X., Bindilatti, V., Oliveira, N.F., Yoshioka, N., and Lahti, P.M.: Magnetic tuning of all-organic binary alloys between two stable radicals. J. Am. Chem. Soc. 134, 3825 (2012).Google Scholar
8. Nishide, H. and Oyaizu, K.: Toward flexible batteries. Science 319, 737 (2008).Google Scholar
9. Kato, F., Kikuchi, A., Okuyama, T., Oyaizu, K., and Nishide, H.: Nitroxide radicals as highly reactive redox mediators in dye-sensitized solar cells. Angew. Chem. Int. Ed. 51, 10177 (2012).Google Scholar
10. Suzuka, M., Hayashi, N., Sekiguchi, T., Sumioka, K., Takata, M., Hayo, N., Ikeda, H., Oyaizu, K., and Nishide, H.: A quasi-solid state DSSC with 10.1% efficiency through molecular design of the charge-separation and -transport. Sci. Rep. 6, 28022 (2016).Google Scholar
11. Suga, T., Pu, Y., Oyaizu, K., and Nishide, H.: Electron-transfer kinetics of nitroxide radicals as an electrode-active material. Bull. Chem. Soc. Jpn. 77, 2203 (2004).Google Scholar
12. Yonekuta, Y., Oyaizu, K., and Nishide, H.: Structural implication of oxoammonium cations for reversible organic one-electron redox reaction to nitroxide radicals. Chem. Lett. 36, 866 (2007).Google Scholar
13. Cheng, Y., Yang, S., and Hsu, C.: Synthesis of conjugated polymers for organic solar cell applications. Chem. Rev. 109, 5868 (2009).Google Scholar
14. Koch, N.: Organic electronic devices and their functional interfaces. ChemPhysChem. 8, 1438 (2007).Google Scholar
15. Ong, C., Bayley, P.M., Jensen, O.W., and Jensen, B.W.: Toward a trace-free oxidant—insight into unexpected high yields of vapor phase polymerized polyterthiophene. Polymer J. 45, 395 (2013).Google Scholar
16. Kojima, A., Teshima, K., Shirai, Y., and Miyasaka, T.: Organometal halide perovskites as visible-light sensitizers for photovoltaic cells. J. Am. Chem. Soc. 131, 6050 (2009).Google Scholar
17. Burschka, J., Pellet, N., Moon, S., Baker, R.H., Gao, P., Nazeeruddin, M.K., and Grätzel, M.: Sequential deposition as a route to high-performance perovskite-sensitized solar cells. Nature 499, 316 (2013).Google Scholar
18. Cojocaru, L., Uchida, S., Takumi, K., Jayaweera, O.V., Kaneko, S., Nakazaki, J., Kubo, T., and Segawa, H.: Determination of unique power conversion efficiency of solar cell showing hysteresis in the IV curve under various light intensities. Sci. Rep. 7, 11790 (2017).Google Scholar
19. Li, X., Bi, D., Yi, C., Dècoppet, J., Luo, J., Zakeeruddin, S.M., Hagfeldt, A., and Grätzel, M.: A vacuum flash-assisted solution process for high-efficiency large-area perovskite solar cells. Science 353, 58 (2016).Google Scholar
20. Saliba, M., Matsui, T., Domanski, K., Seo, J.Y., Ummadisingu, A., Zakeeruddin, S.M., Correa, J.P., Tres, W.R., Abate, A., Hagfeldt, A., and Grätzel, M.: Incorporation of rubidium cations into perovskite solar cells improves photovoltaic performance. Science 354, 206 (2016).Google Scholar
21. Bach, U., Lupo, D., Comte, P., Moser, J.E., Weissörtel, F., Salbeck, J., Spreitzer, H., and Grätzel, M.: Solid-state dye-sensitized mesoporous TiO2 solar cells with high photon-to-electron conversion efficiencies. Nature 395, 583 (1998).Google Scholar
22. Saragi, T., Spehr, T., Siebert, A., Lieker, T.F., and Salbeck, J.: Spiro compounds for organic optoelectronics. Chem. Rev. 107, 1011 (2007).Google Scholar
23. Anaraki, E.H., Kermanpur, A., Steier, L., Domanski, K., Matsui, T., Tress, W., Saliba, M., Abate, A., Grätzel, M., Hagfeldt, A., and Correa-Baena, J.P.: Cesium-containing triple cation perovskite solar cells: improved stability, reproducibility and high efficiency. Energy Environ. Sci. 9, 1989 (2016).Google Scholar
24. Burschka, J., Kessler, F., Nazeeruddin, M.K., and Grätzel, M.: Co(III) complexes as p-dopants in solid-state dye-sensitized solar cells. Chem. Mater. 25, 2986 (2013).Google Scholar
25. Hagfeldt, A., Boschloo, G., Sun, L., Kloo, L., and Pettersson, H.: Dye-sensitized solar cells. Chem. Rev. 110, 6595 (2010).Google Scholar
26. Hawash, Z., Ono, L.K., Raga, S.R., Lee, M.V., and Qi, Y.: Air-exposure induced dopant redistribution and energy level shifts in spin-coated spiro-MeOTAD films. Chem. Mater. 27, 562 (2015).Google Scholar
27. Ameen, S., Rub, M.A., Kosa, S.A., Alamry, K.A., Akhtar, M.S., Shin, H.S., Seo, H.K., Asiri, A.M., and Nazeeruddin, M.K.: Perovskite solar cells: influence of hole transporting materials on power conversion efficiency. ChemSusChem 9, 10 (2016).Google Scholar
28. Koh, T.M., Dharani, S., Li, H., Prabhakar, R.R., Mathews, N., Grimsdale, A.C., and Mhaisalkar, S.G.: Cobalt dopant with deep redox potential for organometal halide hybrid solar cells. ChemSusChem 7, 1909 (2014).Google Scholar
29. Bisquert, J.: Theory of the impedance of electron diffusion and recombination in a thin layer. J. Phys. Chem. B 106, 326 (2002).Google Scholar
30. Abate, A., Leijtens, T., Pathak, S., Teuscher, J., Avolio, R., Errico, M.E., Kirkpatrik, J., Ball, J.M., Docampo, P., Mcpherson, I., and Snaith, H.J.: Lithium salts as “redox active” p-type dopants for organic semiconductors and their impact in solid-state dye-sensitized solar cells. Phys. Chem. Chem. Phys. 15, 2572 (2013).Google Scholar
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