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 language | English |
|---|---|
| Pages (from-to) | 2147-2154 |
| Number of pages | 8 |
| Journal | Chemistry of Materials |
| Volume | 26 |
| Issue number | 6 |
| DOIs | |
| Publication status | Published - 2014 Mar 25 |
| Externally published | Yes |
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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 journal › Article
}
TY - JOUR
T1 - Benzotriazole-containing planar conjugated polymers with noncovalent conformational locks for thermally stable and efficient polymer field-effect transistors
AU - Yum, Seungjib
AU - An, Tae Kyu
AU - Wang, Xiaowei
AU - Lee, Wonho
AU - Uddin, Mohammad Afsar
AU - Kim, Yu Jin
AU - Nguyen, Thanh Luan
AU - Xu, Shuhao
AU - Hwang, Sungu
AU - Park, Chan Eon
AU - Woo, Han Young
PY - 2014/3/25
Y1 - 2014/3/25
N2 - 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.
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.
UR - http://www.scopus.com/inward/record.url?scp=84896967926&partnerID=8YFLogxK
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U2 - 10.1021/cm4042346
DO - 10.1021/cm4042346
M3 - Article
AN - SCOPUS:84896967926
VL - 26
SP - 2147
EP - 2154
JO - Chemistry of Materials
JF - Chemistry of Materials
SN - 0897-4756
IS - 6
ER -