Functionalized dithieno[2,3-b

3′,2′-d]thiophenes (DTTs) for organic thin-film transistors

Choongik Kim, Ming Chou Chen, Yen Ju Chiang, Yue Jhih Guo, Jangdae Youn, Hui Huang, You Jhih Liang, Yu Jou Lin, Yu Wen Huang, Tarng Shiang Hu, Gene Hsiang Lee, Antonio Facchetti, Tobin J Marks

Research output: Contribution to journalArticle

56 Citations (Scopus)

Abstract

A series of dithieno[2,3-b:3′,2′-d]thiophene (DTT; 1) derivatives were synthesized and characterized. Facile, one-pot [2 + 1] and [1 + 1 + 1] synthetic methods of DTT were developed, which enabled the efficient realization of a new DTT-based semiconductor series for organic thin-film transistors (OTFTs). These DTTs are end-functionalized with perfluorophenyl (FP-), perfluorobenzoyl (FB-), benzoyl (B-), 2-naphthylcarbonyl (Np-), 2-benzothiazolyl (BS-), 2-thienylcarbonyl (T-), and 2-(5-hexyl)thienylcarbonyl (HT-) groups. The molecular structures of DFP-DTT (3), DFB-DTT (4), FBB-DTT (5), DB-DTT (6), and DNp-TT (7) were determined via single-crystal X-ray diffraction. Our studies reveal that the majority of these carbonyl-containing derivatives exhibit p-channel transport with hole mobilities of up to 0.01 cm2/Vs for DB-DTT and DBS-DTT, while perfluorobenzoyl and perfluorophenyl-substituted compounds exhibit n-channel transport with mobilities up to 0.002 cm2/Vs for DFB-DTT, 0.03 cm2/Vs for FBB-DTT, and 0.07 cm2/Vs for DFP-DTT, rendering the latter the DTT derivative currently having the highest electron mobility in OTFT devices. Within this family, the carrier mobility values are strongly dependent upon the semiconductor growth temperature and the dielectric surface treatment.

Original languageEnglish
Pages (from-to)801-813
Number of pages13
JournalOrganic Electronics: physics, materials, applications
Volume11
Issue number5
DOIs
Publication statusPublished - May 2010

Fingerprint

Thiophenes
Thiophene
Thin film transistors
thiophenes
Isoflurophate
transistors
direct broadcast satellites
Derivatives
hole mobility
Semiconductor growth
thin films
carrier mobility
surface treatment
electron mobility
Hole mobility
molecular structure
Electron mobility
Carrier mobility
Growth temperature
Molecular structure

Keywords

  • Fused thiophene
  • Organic semiconductor
  • Organic thin-film transistor

ASJC Scopus subject areas

  • Biomaterials
  • Electronic, Optical and Magnetic Materials
  • Materials Chemistry
  • Electrical and Electronic Engineering
  • Chemistry(all)
  • Condensed Matter Physics

Cite this

Functionalized dithieno[2,3-b : 3′,2′-d]thiophenes (DTTs) for organic thin-film transistors. / Kim, Choongik; Chen, Ming Chou; Chiang, Yen Ju; Guo, Yue Jhih; Youn, Jangdae; Huang, Hui; Liang, You Jhih; Lin, Yu Jou; Huang, Yu Wen; Hu, Tarng Shiang; Lee, Gene Hsiang; Facchetti, Antonio; Marks, Tobin J.

In: Organic Electronics: physics, materials, applications, Vol. 11, No. 5, 05.2010, p. 801-813.

Research output: Contribution to journalArticle

Kim, C, Chen, MC, Chiang, YJ, Guo, YJ, Youn, J, Huang, H, Liang, YJ, Lin, YJ, Huang, YW, Hu, TS, Lee, GH, Facchetti, A & Marks, TJ 2010, 'Functionalized dithieno[2,3-b: 3′,2′-d]thiophenes (DTTs) for organic thin-film transistors', Organic Electronics: physics, materials, applications, vol. 11, no. 5, pp. 801-813. https://doi.org/10.1016/j.orgel.2010.01.022
Kim, Choongik ; Chen, Ming Chou ; Chiang, Yen Ju ; Guo, Yue Jhih ; Youn, Jangdae ; Huang, Hui ; Liang, You Jhih ; Lin, Yu Jou ; Huang, Yu Wen ; Hu, Tarng Shiang ; Lee, Gene Hsiang ; Facchetti, Antonio ; Marks, Tobin J. / Functionalized dithieno[2,3-b : 3′,2′-d]thiophenes (DTTs) for organic thin-film transistors. In: Organic Electronics: physics, materials, applications. 2010 ; Vol. 11, No. 5. pp. 801-813.
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