Abstract
Lately, non-fullerene acceptors (NFAs) have received increasing attention for use in polymer-based bulk-heterojunction (BHJ) organic solar cells (OSCs), as improved photovoltaic performance compared to classical polymer–fullerene blends could be demonstrated. In this study, polymer solar cells based on a statistically substituted anthracene-containing poly(p-phenylene ethynylene)-alt-poly(p-phenylene vinylene)s (PPE–PPVs) copolymer (AnE-PVstat) as donor in combination with a number of different electron accepting materials were investigated. Strong photoluminescence quenching of the polymer donor indicates intimate intermixing of both materials. However, the photovoltaic performances were found to be poor compared to blends that use fullerene as acceptor. Time-delayed collection field (TDCF) measurements demonstrate: charge generation is field-independent, but bimolecular recombination processes limit the fill factor and thus the efficiency of devices.
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References
Albrecht S et al (2012) On the field dependence of free charge carrier generation and recombination in blends of PCPDTBT/PC70BM: influence of solvent additives. J Phys Chem Lett 3:640–645. https://doi.org/10.1021/jz3000849
Allemand P et al (1991) Two different fullerenes have the same cyclic voltammetry. J Am Chem Soc 113:1050–1051
Bicciocchi E, Haeussler M, Rizzardo E, Scully AD, Ghiggino KP (2015) Donor-acceptor rod-coil block copolymers comprising Poly[2,7-(9,9-dihexylfluorene)-alt-bithiophene] and fullerene as compatibilizers for organic photovoltaic devices. J Polymer Scie Part A Polymer Chem 53:888–903. https://doi.org/10.1002/pola.27514
Cann J, Dayneko S, Sun JP, Hendsbee AD, Hill IG, Welch GC (2017a) N-Annulated perylene diimide dimers: acetylene linkers as a strategy for controlling structural conformation and the impact on physical, electronic, optical and photovoltaic properties. J Mater Chem C 5:2074–2083. https://doi.org/10.1039/c6tc05107c
Cann JR, Cabanetos C, Welch GC (2017b) Spectroscopic engineering toward near-infrared absorption of materials containing perylene diimide. ChemPlusChem 82:1359–1364. https://doi.org/10.1002/cplu.201700502
Cao WR, Xue JG (2014) Recent progress in organic photovoltaics: device architecture and optical design. Energy Environ Sci 7:2123–2144. https://doi.org/10.1039/c4ee00260a
Dayneko SV, Hendsbee AD, Welch GC (2017) Fullerene-free polymer solar cells processed from non-halogenated solvents in air with PCE of 4.8%. Chem Commun 53:1164–1167. https://doi.org/10.1039/c6cc08939a
Eftaiha AF, Sun JP, Hill IG, Welch GC (2014) Recent advances of non-fullerene, small molecular acceptors for solution processed bulk heterojunction solar cells. J Mater Chem A 2:1201–1213. https://doi.org/10.1039/c3ta14236a
Egbe DAM et al (2010) Improvement in carrier mobility and photovoltaic performance through random distribution of segments of linear and branched side chains. J Mater Chem 20:9726–9734. https://doi.org/10.1039/C0JM01482F
Günes S, Neugebauer H, Sariciftci NS (2007) Conjugated polymer-based organic solar cells. Chem Rev 107:1324–1338
Holdren JP (1991) Population and the energy problem. Popul Environ 12:231–255. https://doi.org/10.1007/bf01357916
Howard IA, Etzold F, Laquai F, Kemerink M (2014) Nonequilibrium charge dynamics in organic solar cells. Adv Energy Mater 4:9. https://doi.org/10.1002/aenm.201301743
Hummelen JC, Knight BW, LePeq F, Wudl F, Yao J, Wilkins CL (1995) Preparation and characterization of fulleroid and methanofullerene derivatives. J Org Chem 60:532–538
IEA (2015) World Energy Outlook. International Energy Agency 9 rue de la Fédération 75739 Paris Cedex 15, France
Kastner C, Muhsin B, Wild A, Egbe DAM, Rathgeber S, Hoppe H (2013) Improved phase separation in polymer solar cells by solvent blending. J Polymer Sci Part B Polymer Phys 51:868–874. https://doi.org/10.1002/polb.23286
Kastner C, Egbe DAM, Hoppe H (2015) Polymer aggregation control in polymer-fullerene bulk heterojunctions adapted from solution. J Mater Chem A 3:395–403. https://doi.org/10.1039/c4ta04736b
Kivrak A, Calis H, Topal Y, Kivrak H, Kus M (2017a) Synthesis of thiophenyl-substituted unsymmetrical anthracene derivatives and investigation of their electrochemical and electrooptical properties. Sol Energy Mater Sol Cells 161:31–37. https://doi.org/10.1016/j.solmat.2016.11.006
Kivrak A, Er OF, Kivrak H, Topal Y, Kus M, Camlisoy Y (2017b) Synthesis and solar-cell applications of novel furanyl-substituted anthracene derivatives. Opt Mater 73:206–212. https://doi.org/10.1016/j.optmat.2017.08.014
Kniepert J, Schubert M, Blakesley JC, Neher D (2011) Photogeneration and Recombination in P3HT/PCBM solar cells probed by time-delayed collection field experiments. J Phys Chem Lett 2:700–705. https://doi.org/10.1021/jz200155b
Kniepert J, Lange I, van der Kaap NJ, Koster LJA, Neher D (2014) A Conclusive view on charge generation, recombination, and extraction in as-prepared and annealed P3HT:PCBM blends: combined experimental and simulation work. Adv Energy Mater 4 https://doi.org/10.1002/aenm.201301401
Kozma E, Catellani M (2013) Perylene diimides based materials for organic solar cells. Dyes Pigm 98:160–179. https://doi.org/10.1016/j.dyepig.2013.01.020
Krebs FC, Nielsen TD, Fyenbo J, Wadstrøm M, Pedersen MS (2010) Manufacture, integration and demonstration of polymer solar cells in a lamp for the “Lighting Africa” initiative. Energy Environ Sci 3:512–525
Liang N, Jiang W, Hou J, Wang Z (2017) New developments in non-fullerene small molecule acceptors for polymer solar cells. Mater Chem Front 1:1291–1303. https://doi.org/10.1039/C6QM00247A
Lin Y, Wang J, Zhang Z-G, Bai H, Li Y, Zhu D, Zhan X (2015) An electron acceptor challenging fullerenes for efficient polymer solar cells. Adv Mater 27:1170–1174. https://doi.org/10.1002/adma.201404317
Liu ZT, Wu Y, Zhang Q, Gao X (2016) Non-fullerene small molecule acceptors based on perylene diimides. J Mater Chem A 4:17604–17622. https://doi.org/10.1039/c6ta06978a
McAfee SM, Topple JM, Hill IG, Welch GC (2015) Key components to the recent performance increases of solution processed non-fullerene small molecule acceptors. J Mater Chem A 3:16393–16408. https://doi.org/10.1039/c5ta04310g
McAfee SM, Dayneko SV, Josse P, Blanchard P, Cabanetos C, Welch GC (2017) Simply Complex: the efficient synthesis of an intricate molecular acceptor for high-performance air-processed and air-tested fullerene-free organic solar cells. Chem Mater 29:1309–1314. https://doi.org/10.1021/acs.chemmater.6b04862
Mulligan CJ, Wilson M, Bryant G, Vaughan B, Zhou X, Belcher WJ, Dastoor PC (2014) A projection of commercial-scale organic photovoltaic module costs. Sol Energy Mater Sol Cells 120:9–17
Namazian M, Lin CY, Coote ML (2010) Benchmark calculations of absolute reduction potential of ferricinium/ferrocene couple in nonaqueous solutions. J Chem Theory Comput 6:2721–2725. https://doi.org/10.1021/ct1003252
Nielsen CB, Holliday S, Chen H-Y, Cryer SJ, McCulloch I (2015) Non-fullerene electron acceptors for use in organic solar cells. Acc Chem Res 48:2803–2812. https://doi.org/10.1021/acs.accounts.5b00199
Ren G, Ahmed E, Jenekhe SA (2011) Non-fullerene acceptor-based bulk heterojunction polymer solar cells: engineering the nanomorphology via processing additives. Adv Energy Mater 1:946–953. https://doi.org/10.1002/aenm.201100285
Singh TB et al (2005) High-mobility n-channel organic field-effect transistors based on epitaxially grown C 60 films. Org Electron 6:105–110
Sonar P, Lim JPF, Chan KL (2011) Organic non-fullerene acceptors for organic photovoltaics Energy. Environ Sci 4:1558–1574
Thompson BC, Fréchet JM (2008) Polymer–fullerene composite solar cells. Angew Chem Int Ed 47:58–77
Wadsworth A et al (2017) Highly efficient and reproducible nonfullerene solar cells from hydrocarbon solvents. ACS Energy Lett 2:1494–1500. https://doi.org/10.1021/acsenergylett.7b00390
Wienk MM, Kroon JM, Verhees WJ, Knol J, Hummelen JC, van Hal PA, Janssen RA (2003) Efficient methano [70] fullerene/MDMO-PPV bulk heterojunction photovoltaic cells. Angew Chem 115:3493–3497
Zhao W, Li S, Yao H, Zhang S, Zhang Y, Yang B, Hou J (2017) Molecular optimization enables over 13% efficiency in organic solar cells. J Am Chem Soc 139:7148–7151
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SA, VON, and HH are grateful for financial support via DFG in the frame of “PhotoGenOrder”.
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Alam, S., Meitzner, R., Nwadiaru, O.V. et al. Organic solar cells based on anthracene-containing PPE–PPVs and non-fullerene acceptors. Chem. Pap. 72, 1769–1778 (2018). https://doi.org/10.1007/s11696-018-0466-y
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DOI: https://doi.org/10.1007/s11696-018-0466-y