A-D-A Type Semiconducting Small Molecules with Bis(alkylsulfanyl)methylene Substituents and Control of Charge Polarity for Organic Field-Effect Transistors

Sung Joon Cho, Min Je Kim, Ziang Wu, Jae Hoon Son, Sang Young Jeong, Sungjoo Lee, Jeong Ho Cho, Han Young Woo

Research output: Contribution to journalArticlepeer-review

Abstract

In this study, we synthesize four different kinds of bis(alkylsulfanyl)methylene-substituted 4,9-dihydro-s-indaceno[1,2-b:5,6-b′]dithiophene (IDT)-based acceptor-donor-acceptor (A-D-A) type small molecules (IDSIC, IDSIC-4F, IDSIC-4Cl, and IDSTIC) by incorporating electron-withdrawing halogen atoms or electron-releasing thiophene spacers. Herein, enhanced structural planarity and crystalline intermolecular packing are induced by the sp2-hybridized C=C double bond side chains and sulfur-sulfur chalcogen interactions. The fine control of intramolecular charge transfer modulates the electrochemical characteristics and the resulting carrier polarity in organic field-effect transistors (OFETs). Well-balanced ambipolar, n-dominant, and p-dominant charge transport properties are successfully demonstrated in OFETs by modulating the electron-donating or withdrawing strength based on the A-D-A structural motif, resulting in hole/electron mobilities of 0.599/0.553, 0.003/0.019, 0.092/0.897, and 0.683/0.103 cm2/V·s for IDSIC, IDSIC-4F, IDSIC-4Cl, and IDSTIC respectively, after thermal annealing at 200 °C. Thermal annealing of the as-cast films improves the intermolecular packing in an edge-on fashion, which is investigated in detail by grazing incidence X-ray scattering. Finally, complementary logic circuits, i.e., NOT, NAND, and NOR, are fabricated by assembling p-dominant IDSTIC and n-dominant IDSIC-4Cl OFETs. Therefore, a simple and efficient molecular design strategy for fine tuning the charge polarity and charge transport properties of OFET devices is presented.

Original languageEnglish
Pages (from-to)41842-41851
Number of pages10
JournalACS Applied Materials and Interfaces
Volume12
Issue number37
DOIs
Publication statusPublished - 2020 Sep 16

Keywords

  • A-D-A structure
  • OFET
  • ambipolar transistor
  • charge polarity
  • organic field-effect transistor

ASJC Scopus subject areas

  • Materials Science(all)

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