Heteroannulated acceptors based on benzothiadiazole

Timothy C. Parker, Dinesh G. Patel*, Karttikay Moudgil, Stephen Barlow, Chad Risko, Jean-Luc Bredas, John R. Reynolds, Seth R. Marder

*Corresponding author for this work

Research output: Contribution to journalReview articlepeer-review

84 Scopus citations

Abstract

Increasing the acceptor strength of the widely used acceptor benzothiadiazole (BT) by extending the heterocyclic core is a promising strategy for developing new and stronger acceptors for materials in organic electronics and photonics. In recent years, such heteroannulated BT acceptors have been incorporated into a wide variety of materials that have been used in organic electronic and photonic devices. This review critically assesses the properties of these materials. Although heteroannulation to form acceptors, such as benzo[1,2-c:4,5-c′]bis[1,2,5]thiadiazole (BBT), does result in materials with significantly higher electron affinity (EA) relative to BT, in many cases the extended BT systems also exhibit lower ionization energy (IE) than BT. Both the significantly higher EA and lower IE limit the efficacy of these materials in applications such as bulk heterojunction organic photovoltaics (BHJ-OPV) based on C60. Although the relatively high EA may enable some applications such as air stable organic field effect transistors (OFET), more widespread use of heteroannulated BT acceptors will likely require the ability to moderate or retain the high EA while increasing IE.

Original languageEnglish (US)
Pages (from-to)22-36
Number of pages15
JournalMaterials Horizons
Volume2
Issue number1
DOIs
StatePublished - Jan 1 2015

ASJC Scopus subject areas

  • Materials Science(all)
  • Mechanics of Materials
  • Process Chemistry and Technology
  • Electrical and Electronic Engineering

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