Synthesis and characterization of heterocyclic conjugated polymers containing planar benzo[c]cinnoline and tetraazapyrene structures for organic field-effect transistor application

Shih Wei Lee, Shih Hsuan Chien, Jyh Chien Chen*, Shih Hao Wang, Lee Yih Wang, Bo Han Lai, Chien-Lung Wang

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

1 Scopus citations

Abstract

Heterocyclic conjugated polymers BZCTVT and TAPTVT containing benzo[c]cinnoline (BZC) and tetraazapyrene (TAP), respectively, were prepared by using Stille coupling polymerization in microwave reactor. BZC and TAP act as acceptors and thiophene-vinylene-thiophene (TVT) acts as donors. Alkylated thiophene is the linker between acceptor and donor. This is the first time that tetraazapyrene was incorporated into conjugated polymers. The films of BZCTVT and TAPTVT showed maximum absorption wavelength at 522 and 534 nm, respectively. From cyclic voltammertry measurement, TAPTVT and BZCTVT exhibited low LUMO (−3.61 and −3.47 eV) and HOMO (−5.64 and −5.63 eV) energy levels. Even though BZC and TAP were planar structures, BZCTVT and TAPTVT showed large dihedral angles between alkylated thiophene and TVT (10.8–22.6°), and between alkylated thiophene and BZC and TAP (22.2–30.3°) based on their simulated energy-minimized geometry. The bottom-gate, top-contact OFETs based on TAPTVT and BZCTVT exhibited only p-channel behavior with hole mobility of 4.63 × 10−4 and 1.04 × 10−4 cm2 V−1 s−1 and current on/off ratios greater than 104 after thermal annealing. Grazing incidence X-ray diffraction (GIXRD) patterns suggested that thin films of TAPTVT and BZCTVT preferred edge-on orientation.

Original languageEnglish
Pages (from-to)136-147
Number of pages12
JournalOrganic Electronics
Volume66
DOIs
StatePublished - 1 Mar 2019

Keywords

  • Benzo[c]cinnoline
  • Heterocycli conjugated
  • OFET
  • Polymers
  • TVT
  • Traazapyrene

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