Benzotriazole-containing planar conjugated polymers with noncovalent conformational locks for thermally stable and efficient polymer field-effect transistors

Seungjib Yum, Tae Kyu An, Xiaowei Wang, Wonho Lee, Mohammad Afsar Uddin, Yu Jin Kim, Thanh Luan Nguyen, Shuhao Xu, Sungu Hwang, Chan Eon Park, Han Young Woo

Research output: Contribution to journalArticle

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Abstract

We report a series of benzotriazole-based semicrystalline π-conjugated polymers with noncovalent conformational locks for applications in polymer field-effect transistors. The benzotriazole moiety is a versatile electron-deficient building block that offers two chemically functionalizable sites, 2(N) and 5, 6(C) positions, allowing easy modulation of the solution processability and electronic structures of the resulting polymers. Fluorine or alkoxy substituents were introduced to the benzotriazole unit to enhance the molecular ordering through intra- and intermolecular F···S, F···H-C, C-F···πF, or S···O attractive interactions. The fluorinated polymer (PTBTz-F) showed remarkably enhanced hole mobility (μh = 1.9 cm2/(V·s), on/off ratio = 8 × 107) upon thermal annealing at 305 °C, compared to the unsubstituted one (PTBTz) (μh = 7.0 × 10-3 cm2/(V·s), on/off ratio = 3 × 106). Alkoxy unit substitution (PTBTz-OR) also improved the carrier mobility up to 0.019 cm2/(V·s) with an on/off ratio of 4 × 105. Fluorine or alkoxy substitution induced tight interchain ordering with edge-on orientation, as confirmed by X-ray diffraction measurements. In particular, fluorinated PTBTz-F showed high thermal stability (Td 453 °C) and the remarkable device characteristics with deep frontier orbital levels.

Original languageEnglish
Pages (from-to)2147-2154
Number of pages8
JournalChemistry of Materials
Volume26
Issue number6
DOIs
Publication statusPublished - 2014 Mar 25
Externally publishedYes

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Conjugated polymers
Field effect transistors
Polymers
Fluorine
Fluorocarbon Polymers
Substitution reactions
Hole mobility
Carrier mobility
Electronic structure
Thermodynamic stability
Modulation
Annealing
X ray diffraction
Electrons
benzotriazole
alkoxyl radical

ASJC Scopus subject areas

  • Chemistry(all)
  • Chemical Engineering(all)
  • Materials Chemistry

Cite this

Benzotriazole-containing planar conjugated polymers with noncovalent conformational locks for thermally stable and efficient polymer field-effect transistors. / Yum, Seungjib; An, Tae Kyu; Wang, Xiaowei; Lee, Wonho; Uddin, Mohammad Afsar; Kim, Yu Jin; Nguyen, Thanh Luan; Xu, Shuhao; Hwang, Sungu; Park, Chan Eon; Woo, Han Young.

In: Chemistry of Materials, Vol. 26, No. 6, 25.03.2014, p. 2147-2154.

Research output: Contribution to journalArticle

Yum, Seungjib ; An, Tae Kyu ; Wang, Xiaowei ; Lee, Wonho ; Uddin, Mohammad Afsar ; Kim, Yu Jin ; Nguyen, Thanh Luan ; Xu, Shuhao ; Hwang, Sungu ; Park, Chan Eon ; Woo, Han Young. / Benzotriazole-containing planar conjugated polymers with noncovalent conformational locks for thermally stable and efficient polymer field-effect transistors. In: Chemistry of Materials. 2014 ; Vol. 26, No. 6. pp. 2147-2154.
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AU - Lee, Wonho

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AU - Kim, Yu Jin

AU - Nguyen, Thanh Luan

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AB - We report a series of benzotriazole-based semicrystalline π-conjugated polymers with noncovalent conformational locks for applications in polymer field-effect transistors. The benzotriazole moiety is a versatile electron-deficient building block that offers two chemically functionalizable sites, 2(N) and 5, 6(C) positions, allowing easy modulation of the solution processability and electronic structures of the resulting polymers. Fluorine or alkoxy substituents were introduced to the benzotriazole unit to enhance the molecular ordering through intra- and intermolecular F···S, F···H-C, C-F···πF, or S···O attractive interactions. The fluorinated polymer (PTBTz-F) showed remarkably enhanced hole mobility (μh = 1.9 cm2/(V·s), on/off ratio = 8 × 107) upon thermal annealing at 305 °C, compared to the unsubstituted one (PTBTz) (μh = 7.0 × 10-3 cm2/(V·s), on/off ratio = 3 × 106). Alkoxy unit substitution (PTBTz-OR) also improved the carrier mobility up to 0.019 cm2/(V·s) with an on/off ratio of 4 × 105. Fluorine or alkoxy substitution induced tight interchain ordering with edge-on orientation, as confirmed by X-ray diffraction measurements. In particular, fluorinated PTBTz-F showed high thermal stability (Td 453 °C) and the remarkable device characteristics with deep frontier orbital levels.

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