Design strategy for air-stable organic semiconductors applicable to high-performance field-effect transistors

Article English OPEN
Kazuo Takimiya et al (2007)
  • Publisher: Taylor & Francis Group
  • Journal: Science and Technology of Advanced Materials (issn: 1468-6996, eissn: 1878-5514)
  • Subject: Materials of engineering and construction. Mechanics of materials | TA401-492 | Biotechnology | TP248.13-248.65

Electronic structure of air-stable, high-performance organic field-effect transistor (OFET) material, 2,7-dipheneyl[1]benzothieno[3,2-b]benzothiophene (DPh-BTBT), was discussed based on the molecular orbital calculations. It was suggested that the stability is originated from relatively low-lying HOMO level, despite the fact that the molecule contains highly π-extended aromatic core ([1]benzothieno[3,2-b]benzothiophene, BTBT) with four fused aromatic rings like naphthacene. This is rationalized by the consideration that the BTBT core is not isoelectronic with naphthacene but with chrysene, a cata-condensed phene with four benzene rings. It is well known that the acene-type compound is unstable among its structural isomers with the same number of benzene rings. Therefore, polycyclic aromatic compounds possessing the phene-substructure will be good candidates for stable organic semiconductors. Considering synthetic easiness, we suggest that the BTBT-substructure is the molecular structure of choice for developing air-stable organic semiconductors.
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