Small-Molecule Azomethines-based Donor Materials for Bulk Heterojunction Solar Cells

Theo Dingemans^a, Ugo Lafont^a, Ricardo Bouwer^a, Michiel Petrus^a^,^b, Richard Friend^c, Aditya Sadhanala^c, Frederik Morgenstern^c, Neil Greenham^c, Stavros Anthanasopoulos^c

^aFaculty of Aerospace Engineering, Delft University of Technology, Kluyverweg 1, Delft, 2629 HS, Netherlands

^bDutch Polymer Institute (DPI), ), P.O. Box 902, 5600 AX Eindhoven, Netherlands

^cOptoelectronics Group, Cavendish Laboratory, University of Cambridge, UK., J.J. Thomson Avenue, Cambridge, United Kingdom

International Conference on Hybrid and Organic Photovoltaics
Proceedings of International Conference on Hybrid and Organic Photovoltaics 2015 (HOPV15)

Roma, Italy, 2015 May 11th - 13th

Organizer: Filippo De Angelis

Poster, Michiel Petrus, 153
Publication date: 5th February 2015

Most of the conjugated materials used in organic electronics are synthesized using time-consuming Suzuki-, Wittig-, or Stille-type coupling reactions. These chemistries, however, require expensive transition metal catalysts, stringent reaction conditions and time-consuming product purification steps. In order to offer a more economic route towards organic photovoltaic materials we are exploring azomethines (–CH=N–) as the conjugated linker unit. Azomethines (also known as Schiff bases) offer significant advantages as they can be prepared using Schiff base condensation chemistry under near ambient reaction conditions. Expensive catalysts are not required and water is the only by-product, making the purification very straightforward. We demonstrated that small-molecule azomethines are promising candidates as electron donating materials for organic photovoltaic devices.¹ Azomethine-based small-molecule bulk heterojunction devices showed efficiencies up to 2.2% when MoO_x was used as hole transporting material.To understand the device performance and limitations of small-molecule azomethine-based OPVs, the spectroscopic properties and device characteristics of TPA-TBT-TPA (Figure 1) was studied using a range of spectroscopic and electro-optical techniques.² Furthermore, the versatility and simplicity of the chemistry was illustrated by preparing a photovoltaic device directly from the reaction mixture without any form of workup.
Figure 1: Reaction scheme and molecular structure of the azomethine-based small-molecule TPA-TBT-TPA.
1. Petrus, M.L.; Bouwer, R.K.M.; Lafont, U.; Athanasopoulos, S.; Greenham N.C.; Dingemans, T.J. "Small-Molecule Azomethines: Organic Photovoltaics via Schiff Base Condensation Chemistry” J. Mater. Chem. A, 2014, 2, 9474–9477 2. Petrus, M.L.; Morgenstern, F.S.F.; Sadhanala, A.; Friend, R.H.; Greenham N.C.; Dingemans, T.J. “Device Performance of Small-Molecule Azomethine-based Bulk Heterojunction Solar Cells” Submitted for publication

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