Abstract
An extended study on a group of four soluble diphenyl-amino-stilbene based diphenyl-diketopyrrolo- pyrrole molecules has been carried out. Using the materials in thin-film transistors it was shown that the above-mentioned compounds can be successfully used as donors in organic photovoltaic devices. Influence of the molecular symmetry and solubilizing chain on the morphology and solar cell performance are described. It was shown that a shorter and non-branched ethyl acetate chain leads to higher charge carrier mobility, short circuit current, and better fill factor. After the basic optimization, a power conversion efficiency of about 1.5 % was reached. This, to the best of our knowledge, is the highest reported efficiency of thiophene-free small-molecule diketo-pyrrolopyrroles.
Similar content being viewed by others
References
Andersson, L. M., M¨uller, C., Badada, B. H., Zhang, F. L., W¨urfel, U., & Inganäs, O. (2011). Mobility and fill factor correlation in geminate recombination limited solar cells. Journal of Applied Physics, 110, 024509. DOI: 10.1063/1.3609079.
Chen, Y. S., Wan, X. J., & Long, G. K. (2013). High performance photovoltaic applications using solution-processed small molecules. Accounts of Chemical Research, 46, 2645–2655. DOI: 10.1021/ar400088c.
Chen, J. H., Xiao, M. J., Meng, F. Y., Duan, L. R., Tan, H., Wang, Y. F., Liu, Y., Yang, R. Q., & Zhu, W. G. (2015). Improving photovoltaic properties of linear small molecules with TPA–DPP segment by tuning frameworks. Synthetic Metals, 199, 400–407. DOI: 10.1016/j.synthmet.2014.12.005.
Cheng, P., Shi, Q. Q., Lin, Y. Z., Li, Y. F., & Zhan, X. W. (2013). Evolved structure of thiazolothiazole based small molecules towards enhanced efficiency in organic solar cells. Organic Electronics, 14, 599–606. DOI: 10.1016/j.orgel.2012. 11.026.
David, J., Weiter, W., Vala, M., Vyňuchal, J., & Kučerík, J. (2011). Stability and structural aspects of diketopyrrolopyrrole pigment and its N−alkyl derivatives. Dyes and Pigments, 89, 137–143. DOI: 10.1016/j.dyepig.2010.10.001.
Deng, D., Yang, Y., Zhang, J., He, C., Zhang, M. J., Zhang, Z. G., Zhang, Z. J., & Li, Y. F. (2011). Triphenylaminecontaining linear D-A-D molecules with benzothiadiazole as acceptor unit for bulk-heterojunction organic solar cells. Organic Electronics, 12, 614–622. DOI: 10.1016/j.orgel.2011.01. 013.
Dou, L. T., You, J. B., Hong, Z. R., Xu, Z., Li, G., Street, R. A., & Yang, Y. (2013). 25th anniversary article: A decade of organic/ polymeric photovoltaic research. Advanced Materials, 25, 6642–6671. DOI: 10.1002/adma.201302563.
Dutta, P., Park, H. N., Lee, W. H., Kang, I. N., & Lee, S. H. (2012a). A crystalline D-π-A organic small molecule with naphto[1,2-b:5,6-b²]dithiophene-core for solution processed organic solar cells. Organic Electronics, 13, 3183–3194. DOI: 10.1016/j.orgel.2012.09.019.
Dutta, P., Yang, W. S., Eom, S. H., & Lee, S. H. (2012b). Synthesis and characterization of triphenylamine flanked thiazole-based small molecules for high performance solution processed organic solar cells. Organic Electronics, 13, 273–282. DOI: 10.1016/j.orgel.2011.11.016.
Ebenhoch, B., Thomson, S. A. J., Genevičius, K., Juška, G., & Samuel, I. D. W. (2015). Charge carrier mobility of the organic photovoltaic materials PTB7 and PC71BM and its influence on device performance. Organic Electronics, 22, 62–68. DOI: 10.1016/j.orgel.2015.03.013.
Guerrero, A., Heidari, H., Ripolles, T. S., Kovalenko, A., Pfannm¨oller, M., Bals, S., Kauffmann, L. D., Bisquert, J., & Garcia-Belmonte, G. (2015a). Shelf life degradation of bulk heterojunction solar cells: Intrinsic evolution of charge transfer complex. Advanced Energy Materials, 5(7). DOI: 10.1002/aenm.201401997. (in press)
Guerrero, A., Pfannm¨oller, M., Kovalenko, A., Ripolles, T. S., Heidari, H., Bals, S., Kaufmann, L. D., Bisquert, J., & Garcia-Belmonte, G. (2015b). Nanoscale mapping by electron energy-loss spectroscopy reveals evolution of organic solar cell contact selectivity. Organic Electronics, 16, 227–233. DOI: 10.1016/j.orgel.2014.11.007.
Holcombe, T. W., Yum, J. H., Yoon, J. H., Gao, P., Marszalek, M., Di Censo, D., Rakstys, K., Nazeeruddin, M. K., & Grätzel, M. (2012). A structural study of DPP-based sensitizers for DSC applications. Chemical Communications, 48, 10724–10726. DOI: 10.1039/c2cc35125k.
Huang, J. H., Zhan, C. L., Zhang, X., Zhao, Y., Lu, Z. H., Jia, H., Jiang, B., Ye, J., Zhang, S. L., Tang, A. L., Liu, Y. Q., Pei, Q. B., & Yao, J. N. (2013). Solution-processed DPPbased small molecule that gives high photovoltaic efficiency with judicious device optimization. ACS Applied Materials & Interfaces, 5, 2033–2039. DOI: 10.1021/am302896u.
Feng, H. F., Fu, W. F., Li, L. J., Yu, Q. C., Lu, H., Wan, J. H., Shi, M. M., Chen, H. Z., Tan, Z. A., Li, Y. F. (2014). Triphenylamine modified bis-diketopyrrolopyrrole molecular donor materials with extended conjugation for bulk heterojunction solar cells. Organic Electronics, 15, 2575–2586. DOI: 10.1016/j.orgel.2014.07.020.
Frebort, Š., Vala, M., Luňák, S., Jr., Honová, J., Mikysek, T., Eliáš, Z., & Lyčka, A. (2014). Diphenylamine endcapped diketopyrrolopyrroles with phenylene–vinylene conjugation extension. Tetrahedron Letters, 55, 2829–2834. DOI: 10.1016/j.tetlet.2014.03.080.
Frisch, M. J., Trucks, G. W., Schlegel, H. B., Scuseria, G. E., Robb, M. A., Cheeseman, J. R., Scalmani, G., Barone, V., Mennucci, B., Petersson, G. A., Nakatsuji, H., Caricato, M., Li, X., Hratchian, H. P., Izmaylov, A. F., Bloino, J., Zheng, G., Sonnenberg, J. L., Hada, M., Ehara, M., Toyota, K., Fukuda, R., Hasegawa, J., Ishida, M., Nakajima, T., Honda, Y., Kitao, O., Nakai, H., Vreven, T., Montgomery, J. A., Jr., Peralta, J. E., Ogliaro, F., Bearpark, M., Heyd, J. J., Brothers, E., Kudin, K. N., Staroverov, V. N., Kobayashi, R., Normand, J., Raghavachari, K., Rendell, A., Burant, J. C., Iyengar, S. S., Tomasi, J., Cossi, M., Rega, N., Millam, J. M., Klene, M., Knox, J. E., Cross, J. B., Bakken, V., Adamo, C., Jaramillo, J., Gomperts, R., Stratmann, R. E., Yazyev, O., Austin, A. J., Cammi, R., Pomelli, C., Ochterski, J. W., Martin, R. L., Morokuma, K., Zakrzewski, V. G., Voth, G. A., Salvador, P., Dannenberg, J. J., Dapprich, S., Daniels, A. D., Farkas, ¨O., Foresman, J. B., Ortiz, J. V., Cioslowski, J., & Fox, D. J. (2009). Gaussian 09, Revision D.01 [computer software], Wallingford, CT, USA: Gaussian.
Isse, A. A., & Gennaro, A. (2010). Absolute potential of the standard hydrogen electrode and the problem of interconversion of potentials in different solvents. The Journal of Physical Chemistry B, 114, 7894–7899. DOI: 10.1021/jp100402x.
Jeong, B. S., Choi, H. B., Cho, N. R., Ko, H. M., Lim, W. C., Song, K. H., Lee, J. K., & Ko, J. J. (2011). Molecular engineering of diketopyrrolpyrrole-based photosensitizers for solution processed small molecule bulk heterojunction solar cells. Solar Energy Materials and Solar Cells, 95, 1731–1740. DOI: 10.1016/j.solmat.2011.01.041.
Kovalenko, A., Stoyanova, D., Pospisil, J., Zhivkov, I., Fekete, L., Karashanova, D., Kratochvílová, I., Vala, M., & Weiter, M. (2015). Morphology versus vertical phase segregation in solvent annealed small molecule bulk heterojunction organic solar cells. International Journal of Photoenergy, 2015, 238–981. DOI: 10.1155/2015/238981.
Kučerík, J., David, J., Weiter, M., Vala, M., Vyňuchal, J., Ouzzane, I., & Salyk, O. (2012). Stability and physical structure tests of piperidyl and morpholinyl derivatives of diphenyldiketo-pyrrolopyrroles (DPP). Journal of Thermal Analysis and Calorimetry, 108, 467–473. DOI: 10.1007/s10973-011-1896-8.
Lee, O. P., Yiu, A. T., Beaujuge, P. M., Woo, C. H., Holcombe, T. W., Millstone, J. E., Douglas, J. D., Chen, M. S., & Fréchet, J. M. J. (2011). Efficient small molecules bulk heterojunction solar cells with high fill factors via pyrenedirected molecular self-assembly. Advanced Materials, 23, 5359–5363. DOI: 10.1002/adma.201103177.
Lee, H. K. H., Li, Z., Constantinou, I., So, F., Tsang, S. W., & So, S. K. (2014). Batch-to-batch variation of polymeric photovoltaic materials: its origin and impacts on charge carrier transport and device performances. Advanced Energy Materials, 4(16). DOI: 10.1002/aenm.201400768. (in press)
Leliége, A., Blanchard, P., Rousseau, T., & Roncali, J. (2011). Triphenylamine/tetracyanobutadiene-based D-A-D π-conjugated systems as molecular donors for organic solar cells. Organic Letters, 13, 3098–3101. DOI: 10.1021/ol2010 02j.
Li, Z. F., Dong, Q. F., Xu, B., Li, H., Wen, S. P., Pei, J. N., Yao, S. Y., Lu, H. G., Li, P. F., & Tian, W. J. (2011). New amorphous small molecules—Synthesis, characterization and their application in bulk heterojunction solar cells. Solar Energy Materials and Solar Cells, 95, 2272–2280. DOI: 10.1016/j.solmat.2011.03.040.
Lin, Y. Z., Ma, L. C., Li, Y. F., Liu, Y. Q., Zhu, D. B., & Zhan, X. W. (2013). A solution-processable small molecule based on benzodithiophene and diketopyrrolopyrrole for high-performance organic solar cells. Advanced Energy Materials, 3, 1166–1170. DOI: 10.1002/aenm.201300181.
Liu, J. H., Walker, B., Tamayo, A., Zhang, Y., & Nguyen, T. Q. (2013). Effects of heteroatom substitutions on the crystal structure, film formation, and optoelectronic properties of diketopyrrolopyrrole-based materials. Advanced Functional Materials, 23, 47–56. DOI: 10.1002/adfm.201201599.
Loser, S., Bruns, C. J., Miyauchi, H., Ponce Ortiz, R., Facchetti, A., Stupp, S. I., & Marks, T. J. (2011). A naphthodithiophene-diketopyrrolopyrrole donor molecule for efficient solution-processed solar cells. Journal of the American Chemical Society, 133, 8142–8145. DOI: 10.1021/ja202 791n.
Luňák, S., Jr., Vyňuchal, J., Vala, M., Havel, L., & Hrdina, R. (2009). The synthesis, absorption and nufluorescence of polar diketo-pyrrolo-pyrroles. Dyes and Pigments, 82, 102–108. DOI: 10.1016/j.dyepig.2008.12.001.
Luňák, S., Jr., Vala, M., Vyňuchal, J., Ouzzane, I., Horáková, P., Možíšková, P., Eliáš, Z., & Weiter, M. (2011). Absorption and fluorescence of soluble polar diketo-pyrrolo-pyrroles. Dyes and Pigments, 91, 269–278. DOI: 10.1016/j.dyepig. 2011.05.004.
Peumans, P., Uchida, S., & Forrest, S. R. (2003). Efficient bulk heterojunction photovoltaic cells using small-molecularweight organic thin films. Nature, 425, 158–162. DOI: 10.1038/nature01949.
Proctor, C. M., Love, J. A., & Nguyen, T. Q. (2014). Mobility guidelines for high fill factor solution-processed small molecule solar cells. Advanced Materials, 26, 5957–5961. DOI: 10.1002/adma.201401725.
Qu, S. Y., & Tian, H. (2012). Diketopyrrolopyrrole (DPP)-based materials for organic photovoltaics. Chemical Communications, 48, 3039–3051. DOI: 10.1039/c2cc17886a.
Shang, H. X., Fan, H. J., Shi, Q. Q., Li, S., Li, Y. F., & Zhan, X. W. (2010). Solution processable D-A-D molecules based on triphenylamine for efficient organic solar cells. Solar Energy Materials and Solar Cells, 94, 457–464. DOI: 10.1016/j.solmat.2009.11.005.
Shi, Q. Q., Cheng, P., Li, Y. F., & Zhan, X. W. (2012). A solution processable D-A-D molecule based on thiazolothiazole for high performance organic solar cells. Advanced Energy Mateials, 2, 63–67. DOI: 10.1002/aenm.201100505.
Shin, W., Yasuda, T., Watanabe, G., Yang, Y. S., & Adachi, C. (2013). Self-organizing mesomorphic diketopyrrolopyrrole derivatives for efficient solution-processed organic solar cells. Chemistry of Materials, 25, 2549–2556. DOI: 10.1021/cm401244x.
Song, S. H., Ko, S. J., Shin, H. M., Jin, Y. E., Kim, I., Kim, J. Y., & Suh, H. S. (2013). Pyrrolo[3,2-b]pyrrole based small molecules as donor materials for OPVs. Solar Energy Materials and Solar Cells, 112, 120–126. DOI: 10.1016/j.solmat.2013.01.004.
Stassen, A. F., de Boer, R. W. I., Iosad, N. N., & Morpurgo, A. F. (2004). Influence of the gate dielectric on the mobility of rubrene single-crystal field-effect transistors. Applied Physics Letters, 85, 3899–3901. DOI: 10.1063/1.1812368.
Vala, M., Vyňuchal, J., Toman, P., Weiter, M., & Luňák, S., Jr. (2010). Novel, soluble diphenyl-diketo-pyrrolopyrroles: Experimental and theoretical study. Dyes and Pigments, 84, 176–182. DOI: 10.1016/j.dyepig.2009.07.014.
Vala, M., Krajčovič, J., Luňák, S., Jr., Ouzzane, I., Bouillon, J. P., & Weiter, M. (2014). HOMO and LUMO energy levels of N,N²-dinitrophenyl-substituted polar diketopyrrolopyrroles (DPPs). Dyes and Pigments, 106, 136–142. DOI: 10.1016/j.dyepig.2014.03.005.
Walker, B., Tamayo, A. B., Dang, X. D., Zalar, P., Seo, J. H., Garcia, A., Tantiwiwat, M., & Nguyen, T. Q. (2009). Nanoscale phase separation and high photovoltaic efficiency in solution-processed, small-molecule bulk heterojunction solar cells. Advanced Functional Materials, 19, 3063–3069. DOI: 10.1002/adfm.200900832.
Walker, B., Liu, J. H., Kim, C. K., Welch, G. C., Park, J. K., Lin, J., Zalar, P., Proctor, C. M., Seo, J. H., Bazan, G. C., & Nguyen, T. Q. (2013). Optimization of energy levels by molecular design: evaluation of bis-diketopyrrolopyrrole molecular donor materials for bulk heterojunction solar cells. Energy & Environmental Science, 6, 952–962. DOI: 10.1039/c3ee24351f.
Wang, L. H., Yin, L. X., Ji, C. Y., Zhang, Y., Gao, H., & Li, Y. Q. (2014). High open-circuit voltage of the solution-processed organic solar cells based on benzothiadiazole–triphenylamine small molecules incorporating π-linkage. Organic Electronics, 15, 1138–1148. DOI: 10.1016/j.orgel.2014.03.013.
Xue, L. L., He, J. T., Gu, X., Yang, Z. F., Xu, B., & Tian, W. J. (2009). Efficient bulk-heterojunction solar cells based on a symmetrical D-π-A-π-D organic dye molecule. The Journal of Physical Chemistry C, 113, 12911–12917. DOI: 10.1021/jp902976w.
Yum, J. H., Holcombe, T. W., Kim, Y. J., Yoon, J. H., Rakstys, K., Nazeeruddin, M. K., & Grätzel, M. (2012). Towards high-performance DPP-based sensitizer for DSC applications. Chemical Communications, 48, 10727–10729. DOI: 10.1039/c2cc35597c.
Zeng, S. H., Yin, L. X., Jiang, X. Y., Li, Y. Q., & Li, K. C. (2012). D–A–D low band gap molecule containing triphenylamine and benzoxadiazole/benzothiadiazole units: Syntheses and photophysical properties. Dyes and Pigments, 95 229–235. DOI: 10.1016/j.dyepig.2012.04.001.
Zhang, F. J., Zhuo, Z. L., Zhang, J., Wang, X., Xu, X. W., Wang, Z. X., Xin Y. S., Wang, J., Wang, J., Tang, W. H., Xu, Z., & Wang, Y. S. (2012). Influence of PC60BM or PC70BM as electron acceptor on the performance of polymer solar cells. Solar Energy Materials and Solar Cells, 97, 71–77. DOI: 10.1016/j.solmat.2011.09.006.
Zhang, Y. M., Tan, H., Xiao, M. J., Bao, X. C., Tao, Q., Wang, Y. F., Liu, Y., Yang, R. Q., & Zhu, W. G. (2014a). D–A–Ar-type small molecules with enlarged π-system of phenanthrene at terminal for high-performance solution processed organic solar cells. Organic Electronics, 15, 1173–1183. DOI: 10.1016/j.orgel.2014.03.011.
Zhang, J., He, C., Zhang, Z. G., Deng, D., Zhang, M., J., & Li, Y. F. (2014b). D-A-D structured organic molecules with diketopyrrolopyrrole acceptor unit for solution-processed organic solar cells. Philosophical Transactions of the Royal Society A, 372, 20130009. DOI: 10.1098/rsta.2013.0009.
Author information
Authors and Affiliations
Corresponding author
Electronic supplementary material
Rights and permissions
About this article
Cite this article
Honová, J., Luňák, S., Vala, M. et al. Thiophene-free diphenyl-amino-stilbene-diketo-pyrrolo-pyrrole derivatives as donors for organic bulk heterojunction solar cells. Chem. Pap. 70, 1416–1424 (2016). https://doi.org/10.1515/chempap-2016-0068
Received:
Revised:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1515/chempap-2016-0068