Electron-rich anthracene semiconductors containing triarylamine for solution-processed small-molecule organic solar cells

ChemSusChem. 2012 Oct;5(10):2045-52. doi: 10.1002/cssc.201200242. Epub 2012 Aug 7.

Abstract

New electron-rich anthracene derivatives containing triarylamine hole stabilizers, 2,6-bis[5,5'-bis(N,N'-diphenylaniline)-2,2'-bithiophen-5-yl]-9,10-bis-[(triisopropylsilyl)ethynyl]anthracene (TIPSAntBT-TPA) and 2,6-bis(5,5'-bis{4-[bis(9,9-dimethyl-9H-fluoren-2-yl)amino]phenyl}-2,2'-bithiophen-5-yl)-9,10-bis-[(triisopropylsilyl)ethynyl]anthracene (TIPSAntBT-bisDMFA), linked with π-conjugated bithiophene bridges, were synthesized and their photovoltaic characteristics were investigated in solution-processed small-molecule organic solar cells (SMOSCs). These new materials exhibited superior intramolecular charge transfer from triarylamine to anthracene, leading to a more electron-rich anthracene core that facilitated electron transfer into phenyl-C(61)-butyric acid methyl ester. Compared with TIPSAntBT and triarylamine, these materials show a threefold improvement in hole-transporting properties and better photovoltaic performance in solution-processed SMOSCs, with the best power conversion efficiency being 2.96 % at a high open-circuit voltage of 0.85 V.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Amines / chemistry*
  • Anthracenes / chemistry*
  • Electric Power Supplies*
  • Electron Transport
  • Electrons*
  • Models, Molecular
  • Molecular Conformation
  • Semiconductors*
  • Solar Energy*
  • Solutions

Substances

  • Amines
  • Anthracenes
  • Solutions
  • anthracene