Functionalized benzothieno[3,2 b]thiophenes (BTT s) for high performance organic thin-film transistors (OTFTs)

Jangdae Youn, Peng Yi Huang, Shiming Zhang, Chiao Wei Liu, Sureshraju Vegiraju, Kumaresan Prabakaran, Charlotte Stern, Choongik Kim, Ming Chou Chen, Antonio Facchetti, Tobin J Marks

Research output: Contribution to journalArticle

11 Citations (Scopus)

Abstract

New benzothieno[3,2-b]thiophene (BTT) derivatives, end-functionalized with biphenyl (Bp-BTT), naphthalenyl (Np-BTT), and benzothieno[3,2-b]thiophenyl (BBTT; dimer of BTT) moieties, were synthesized and characterized for bottom-gate/top-contact organic thin-film transistors (OTFTs). All three materials exhibit good environmental stability as assessed by thermogravimetric analysis, and no decomposition after extended light exposure, due to their wide band gaps and low-lying HOMOs. The single crystal structures of Bp-BTT and BBTT reveal flat molecular geometries, close π-π stacking, and short sulfur-to-sulfur distances, suggesting an ideal arrangement for charge transport. X-ray diffraction (XRD) measurements verify that the bulk crystal structures are preserved in the polycrystalline thin films. As a consequence, Bp-BTT and BBTT exhibit good OTFT performance, with μ = 0.34 cm2 V-1 s-1 (max) and Ion/Ioff = (3.3 ± 1.6) × 108 for Bp-BTT, and μ = 0.12 cm2 V-1 s-1 (max) and Ion/Ioff = (2.4 ± 0.9) × 107 for BBTT; whereas Np-BTT gives lower device performance with μ = 0.055 cm2 V-1 s-1 (max) and Ion/Ioff = (6.7 ± 3.4) × 10 8. In addition, octadecyltrichlorosilane (OTS) self-assembled monolayer (SAM) treatment of the SiO2 gate dielectric is found to be effective in enhancing the OTFT performance for all three BTT derivatives, by improving the interfacial semiconductor film morphology and in-plane crystallinity.

Original languageEnglish
Pages (from-to)7599-7607
Number of pages9
JournalJournal of Materials Chemistry C
Volume2
Issue number36
DOIs
Publication statusPublished - Sep 28 2014

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Thiophene
Thin film transistors
Ions
Sulfur
Crystal structure
Derivatives
Gate dielectrics
Self assembled monolayers
Dimers
Thermogravimetric analysis
Charge transfer
Energy gap
Single crystals
Semiconductor materials
Decomposition
X ray diffraction
Thin films
Geometry
benzothieno(3,2-b)thiophene

ASJC Scopus subject areas

  • Chemistry(all)
  • Materials Chemistry

Cite this

Functionalized benzothieno[3,2 b]thiophenes (BTT s) for high performance organic thin-film transistors (OTFTs). / Youn, Jangdae; Huang, Peng Yi; Zhang, Shiming; Liu, Chiao Wei; Vegiraju, Sureshraju; Prabakaran, Kumaresan; Stern, Charlotte; Kim, Choongik; Chen, Ming Chou; Facchetti, Antonio; Marks, Tobin J.

In: Journal of Materials Chemistry C, Vol. 2, No. 36, 28.09.2014, p. 7599-7607.

Research output: Contribution to journalArticle

Youn, J, Huang, PY, Zhang, S, Liu, CW, Vegiraju, S, Prabakaran, K, Stern, C, Kim, C, Chen, MC, Facchetti, A & Marks, TJ 2014, 'Functionalized benzothieno[3,2 b]thiophenes (BTT s) for high performance organic thin-film transistors (OTFTs)', Journal of Materials Chemistry C, vol. 2, no. 36, pp. 7599-7607. https://doi.org/10.1039/c4tc01115e
Youn, Jangdae ; Huang, Peng Yi ; Zhang, Shiming ; Liu, Chiao Wei ; Vegiraju, Sureshraju ; Prabakaran, Kumaresan ; Stern, Charlotte ; Kim, Choongik ; Chen, Ming Chou ; Facchetti, Antonio ; Marks, Tobin J. / Functionalized benzothieno[3,2 b]thiophenes (BTT s) for high performance organic thin-film transistors (OTFTs). In: Journal of Materials Chemistry C. 2014 ; Vol. 2, No. 36. pp. 7599-7607.
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AU - Huang, Peng Yi

AU - Zhang, Shiming

AU - Liu, Chiao Wei

AU - Vegiraju, Sureshraju

AU - Prabakaran, Kumaresan

AU - Stern, Charlotte

AU - Kim, Choongik

AU - Chen, Ming Chou

AU - Facchetti, Antonio

AU - Marks, Tobin J

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