Hostname: page-component-848d4c4894-ttngx Total loading time: 0 Render date: 2024-05-12T02:55:10.848Z Has data issue: false hasContentIssue false

Naphthodithiophene-Diketopyrrolopyrrole Small Molecule Donors for Efficient Solution-Processed Solar Cells

Published online by Cambridge University Press:  02 March 2012

Stephen Loser
Affiliation:
Department of Chemistry, Northwestern University, 2145 North Sheridan Road, Evanston, Illinois 60208 USA The Argonne-Northwestern Solar Energy Research (ANSER) Center, Northwestern University, Evanston, Illinois 60208 USA
Carson J. Bruns
Affiliation:
Department of Chemistry, Northwestern University, 2145 North Sheridan Road, Evanston, Illinois 60208 USA
Hiroyuki Miyauchi
Affiliation:
Department of Chemistry, Northwestern University, 2145 North Sheridan Road, Evanston, Illinois 60208 USA
Rocío Ponce Ortiz
Affiliation:
Department of Chemistry, Northwestern University, 2145 North Sheridan Road, Evanston, Illinois 60208 USA
Antonio Facchetti
Affiliation:
Department of Chemistry, Northwestern University, 2145 North Sheridan Road, Evanston, Illinois 60208 USA The Argonne-Northwestern Solar Energy Research (ANSER) Center, Northwestern University, Evanston, Illinois 60208 USA Polyera Corporation, 8045 Lamon Avenue, Skokie, Illinois 60077 USA
Samuel I. Stupp
Affiliation:
Department of Chemistry, Northwestern University, 2145 North Sheridan Road, Evanston, Illinois 60208 USA The Argonne-Northwestern Solar Energy Research (ANSER) Center, Northwestern University, Evanston, Illinois 60208 USA Department of Materials Science and Engineering, Northwestern University, Evanston, Illinois 60208 USA Department of Medicine and the Institute for BioNanotechnology in Medicine, Northwestern University, Chicago, Illinois 60611 USA
Tobin J. Marks
Affiliation:
Department of Chemistry, Northwestern University, 2145 North Sheridan Road, Evanston, Illinois 60208 USA The Argonne-Northwestern Solar Energy Research (ANSER) Center, Northwestern University, Evanston, Illinois 60208 USA
Get access

Abstract

We report the synthesis, characterization, and implementation of various naphtho[2,3- b:6,7-b’]dithiophene (NDT)-based donor molecules for organic photovoltaics (OPVs) When NDT(TDPP)2 (TDPP = thiophene-capped diketopyrrolopyrrole) contains all branched 2- ethylhexyl chains and is combined with the electron acceptor PC61BM, a power conversion efficiency (PCE) of 4.06±0.6% is achieved. This respectable PCE is attributed to the broad, high oscillator strength visible absorption, the ordered molecular packing, and a high hole mobility of 0.04 cm2·V-1·s-1. We find utilizing linear C-12 side chains on either the TDPP or NDT framework dramatically increases the d-spacing, which directly correlates with inferior OPV device performance. This leads to the conclusion that the selection of an appropriate side chain plays a key role in determining OPV device performance of a small molecule donor.

Type
Research Article
Copyright
Copyright © Materials Research Society 2012

Access options

Get access to the full version of this content by using one of the access options below. (Log in options will check for institutional or personal access. Content may require purchase if you do not have access.)

References

REFERENCES

(1) (a) Facchetti, A. Chem. Mater. 2011, 23, 733758. (b) Mayer, A. C.; Scully, S. R.; Hardin, B. E.; Rowell, M. W.; McGehee, M. D., Mater. Today 2007, 10, 28–33. (c) Günes, S.; Neugebauer, H.; Sariciftci, N. S., Chem. Rev. 2007, 107, 1324–1338. (d) Coakley, K. M.; McGehee, M. D., Chem. Mater. 2004, 16, 4533–4542. (e) Spanggaard, H.; Krebs, F. C., Sol. Energy Mater. Sol. Cells 2004, 83, 125–146. (f) Brabec, C. J.; Sariciftci, N. S.; Hummelen, J. C., Adv. Funct. Mater. 2001, 11, 15–26.Google Scholar
(2) (a) Chu, T.-Y.; Lu, J.; Beaupré, S.; Zhang, Y.; Pouliot, J.-R.; Wakim, S.; Zhou, J.; Leclerc, M.; Li, Z.; Ding, J.; Tao, Y., J. Am. Chem. Soc. 2011, 133, 42504253. (b) Price, S. C.; Stuart, A. C.; Yang, L.; Zhou, H.; You, W., J. Am. Chem. Soc. 2011, 133, 4625–4631. (c) Zhou, H.; Yang, L.; Stuart, A. C.; Price, S. C.; Liu, S.; You, W., Angew. Chem. Int. Ed. 2011, 50, 2995–2998. (d) Liang, Y.; Xu, Z.; Xia, J.; Tsai, S.-T.; Wu, Y.; Li, G.; Ray, C.; Yu, L., Adv. Mater. 2010, 22, E135–E138. (e) Chen, H.-Y.; Hou, J.; Zhang, S.; Liang, Y.; Yang, G.; Yang, Y.; Yu, L.; Wu, Y.; Li, G., Nature Photon. 2009, 3, 649–653.Google Scholar
(3) (a) Dennler, G.; Scharber, M. C.; Brabec, C. J., Adv. Mater. 2009, 21, 13231338. (b) Scharber, M. C.; Muehlbacher, D.; Koppe, M.; Denk, P.; Waldauf, C.; Heeger, A. J.; Brabec, C. J., Adv. Mater. 2006, 18, 789–794.Google Scholar
(4) (a) Hains, A. W.; Liu, J.; Martinson, A. B. F.; Irwin, M. D.; Marks, T. J., Adv. Funct. Mater. 2010, 20, 595606. (b) Park, S. H.; Roy, A.; Beaupre, S.; Cho, S.; Coates, N.; Moon, J. S.; Moses, D.; Leclerc, M.; Lee, K.; Heeger, A. J., Nature Photon. 2009, 3, 297–302. (c) Irwin, M. D.; Buchholz, D. B.; Hains, A. W.; Chang, R. P. H.; Marks, T. J., Proc. Natl. Acad. Sci. U. S. A. 2008, 105, 2783–2787.Google Scholar
(5) (a) Boudreault, P.-L. T.; Najari, A.; Leclerc, M., Chem. Mater. 2011, 23, 456469. (b) Zhou, H.; Yang, L.; Price, S. C.; Knight, K. J.; You, W., Angew. Chem., Int. Ed. 2010, 49, 7992– 7995. (c) Piliego, C.; Holcombe, T. W.; Douglas, J. D.; Woo, C. H.; Beaujuge, P. M.; Fréchet, J. M. J., J. Am. Chem. Soc. 2010, 132, 7595–7597. (d) Chen, J.; Cao, Y., Acc. Chem. Res. 2009, 42, 1709–1718. (e) Liang, Y.; Feng, D.; Wu, Y.; Tsai, S.-T.; Li, G.; Ray, C.; Yu, L., J. Am. Chem. Soc. 2009, 131, 7792–7799. (f) Hou, J.; Chen, H.-Y.; Zhang, S.; Chen, R. I.; Yang, Y.; Wu, Y.; Li, G., J. Am. Chem. Soc. 2009, 131, 15586–15587.Google Scholar
(6) (a) Walker, B.; Kim, C.; Nguyen, T.-Q., Chem. Mater. 2011, 23, 470482. (b) Roncali, J., Acc. Chem. Res. 2009, 42, 1719–1730. (c) Lloyd, M. T.; Anthony, J. E.; Malliaras, G. G., Mater. Today 2007, 10, 34–41.Google Scholar
(7) (a) Shang, H.; Fan, H.; Liu, Y.; Hu, W.; Li, Y.; Zhan, X., Adv. Mater. 2011, 23, 15541557. (b) Walker, B.; Tamayo, A. B.; Dang, X. D.; Zalar, P.; Seo, J. H.; Garcia, A.; Tantiwiwat, M.; Nguyen, T. Q., Adv. Funct. Mater. 2009, 19, 3063–3069.Google Scholar
(8) Wei, G.; Wang, S.; Sun, K.; Thompson, M. E.; Forrest, S. R., Adv. Energy Mater. 2011, 1, 184187.Google Scholar
(9) Yin, B.; Yang, L.; Liu, Y.; Chen, Y.; Qi, Q.; Zhang, F.; Yin, S. Appl. Phys. Lett. 2010, 97, 023303-1–;023303–3.Google Scholar
(10) Loser, S.; Bruns, C. J.; Miyauchi, H.; Ortiz, R. P.; Facchetti, A.; Stupp, S. I.; Marks, T. J. J. Am. Chem. Soc. 2011, 133, 81428145.Google Scholar
(11) (a) Yang, H.; Shin, T. J.; Yang, L.; Cho, K.; Ryu, C. Y.; Bao, Z., Adv. Funct. Mater. 2005, 15, 671676. (b) Sirringhaus, H.; Tessler, N.; Friend, R. H., Science 1998, 280, 1741–1744.Google Scholar