Liquid crystalline dialkyl-substituted thienylethenyl [1] benzothieno[3,2-b] benzothiophene derivatives for organic thin film transistors

Ki Hwa Jung; Kyung Hwan Kim; Dong Hoon Lee; Dae Sung Jung; Chan Eon Park; Dong Hoon Choi

doi:10.1016/j.orgel.2010.07.008

Liquid crystalline dialkyl-substituted thienylethenyl [1] benzothieno[3,2-b] benzothiophene derivatives for organic thin film transistors

Ki Hwa Jung, Kyung Hwan Kim, Dong Hoon Lee, Dae Sung Jung, Chan Eon Park, Dong Hoon Choi

Department of Chemistry

Research output: Contribution to journal › Article › peer-review

10 Citations (Scopus)

Abstract

New benzothieno[3,2-b]benzothiophene (BTBT)-based soluble semiconducting molecules have been synthesized through Horner-Emmons coupling reactions using 5-alkylthiophene-2-carbaldehyde and BTBT-diethylphosphonate. The only difference between the two molecules is the length of alkyl chains as a substituent. The molecules are intrinsically thermotropic liquid crystalline (LC) and exhibit good solubility in common organic solvents. The semiconducting properties of the two LC molecules were evaluated in organic thin film transistors (OTFTs). After annealing the samples at the temperature at which liquid crystallinity appears, the TFT device performance improved significantly. The two conjugated molecules 4 and 5 exhibited fairly high charge carrier mobilities of 0.020 cm ²/(Vs) (V_th = -14.5 V, I_ON/OFF = 1.42 × 10⁵) and 0.023 cm²/(Vs) (V_th = -2.0 V, I _ON/OFF = 1.20 × 10⁶), respectively.

Original language	English
Pages (from-to)	1584-1593
Number of pages	10
Journal	Organic Electronics
Volume	11
Issue number	9
DOIs	https://doi.org/10.1016/j.orgel.2010.07.008
Publication status	Published - 2010 Sept

Bibliographical note

Funding Information:
This research work was supported by 21st century Frontier Research Program ( F0004091-0000-00 ). Particularly, D.H. Choi acknowledges the financial support by the Seoul R&BD Program ( 10543; 2009-2010 ). X-ray experiments at PLS were supported by the Ministry of Science and Technology and Pohang Steel Company. This research was supported by Korea Science and Engineering, (KOSEF R0120070001128402008 ).

Keywords

Conjugated molecule
Liquid crystallinity
Mobility
Organic semiconductor
Thin film transistor

ASJC Scopus subject areas

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

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10.1016/j.orgel.2010.07.008

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title = "Liquid crystalline dialkyl-substituted thienylethenyl [1] benzothieno[3,2-b] benzothiophene derivatives for organic thin film transistors",

abstract = "New benzothieno[3,2-b]benzothiophene (BTBT)-based soluble semiconducting molecules have been synthesized through Horner-Emmons coupling reactions using 5-alkylthiophene-2-carbaldehyde and BTBT-diethylphosphonate. The only difference between the two molecules is the length of alkyl chains as a substituent. The molecules are intrinsically thermotropic liquid crystalline (LC) and exhibit good solubility in common organic solvents. The semiconducting properties of the two LC molecules were evaluated in organic thin film transistors (OTFTs). After annealing the samples at the temperature at which liquid crystallinity appears, the TFT device performance improved significantly. The two conjugated molecules 4 and 5 exhibited fairly high charge carrier mobilities of 0.020 cm 2/(Vs) (Vth = -14.5 V, ION/OFF = 1.42 × 105) and 0.023 cm2/(Vs) (Vth = -2.0 V, I ON/OFF = 1.20 × 106), respectively.",

keywords = "Conjugated molecule, Liquid crystallinity, Mobility, Organic semiconductor, Thin film transistor",

author = "Jung, {Ki Hwa} and Kim, {Kyung Hwan} and Lee, {Dong Hoon} and Jung, {Dae Sung} and Park, {Chan Eon} and Choi, {Dong Hoon}",

note = "Funding Information: This research work was supported by 21st century Frontier Research Program ( F0004091-0000-00 ). Particularly, D.H. Choi acknowledges the financial support by the Seoul R&BD Program ( 10543; 2009-2010 ). X-ray experiments at PLS were supported by the Ministry of Science and Technology and Pohang Steel Company. This research was supported by Korea Science and Engineering, (KOSEF R0120070001128402008 ).",

year = "2010",

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doi = "10.1016/j.orgel.2010.07.008",

language = "English",

volume = "11",

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journal = "Organic Electronics",

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T1 - Liquid crystalline dialkyl-substituted thienylethenyl [1] benzothieno[3,2-b] benzothiophene derivatives for organic thin film transistors

AU - Jung, Ki Hwa

AU - Kim, Kyung Hwan

AU - Lee, Dong Hoon

AU - Jung, Dae Sung

AU - Park, Chan Eon

AU - Choi, Dong Hoon

N1 - Funding Information: This research work was supported by 21st century Frontier Research Program ( F0004091-0000-00 ). Particularly, D.H. Choi acknowledges the financial support by the Seoul R&BD Program ( 10543; 2009-2010 ). X-ray experiments at PLS were supported by the Ministry of Science and Technology and Pohang Steel Company. This research was supported by Korea Science and Engineering, (KOSEF R0120070001128402008 ).

PY - 2010/9

Y1 - 2010/9

N2 - New benzothieno[3,2-b]benzothiophene (BTBT)-based soluble semiconducting molecules have been synthesized through Horner-Emmons coupling reactions using 5-alkylthiophene-2-carbaldehyde and BTBT-diethylphosphonate. The only difference between the two molecules is the length of alkyl chains as a substituent. The molecules are intrinsically thermotropic liquid crystalline (LC) and exhibit good solubility in common organic solvents. The semiconducting properties of the two LC molecules were evaluated in organic thin film transistors (OTFTs). After annealing the samples at the temperature at which liquid crystallinity appears, the TFT device performance improved significantly. The two conjugated molecules 4 and 5 exhibited fairly high charge carrier mobilities of 0.020 cm 2/(Vs) (Vth = -14.5 V, ION/OFF = 1.42 × 105) and 0.023 cm2/(Vs) (Vth = -2.0 V, I ON/OFF = 1.20 × 106), respectively.

AB - New benzothieno[3,2-b]benzothiophene (BTBT)-based soluble semiconducting molecules have been synthesized through Horner-Emmons coupling reactions using 5-alkylthiophene-2-carbaldehyde and BTBT-diethylphosphonate. The only difference between the two molecules is the length of alkyl chains as a substituent. The molecules are intrinsically thermotropic liquid crystalline (LC) and exhibit good solubility in common organic solvents. The semiconducting properties of the two LC molecules were evaluated in organic thin film transistors (OTFTs). After annealing the samples at the temperature at which liquid crystallinity appears, the TFT device performance improved significantly. The two conjugated molecules 4 and 5 exhibited fairly high charge carrier mobilities of 0.020 cm 2/(Vs) (Vth = -14.5 V, ION/OFF = 1.42 × 105) and 0.023 cm2/(Vs) (Vth = -2.0 V, I ON/OFF = 1.20 × 106), respectively.

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KW - Liquid crystallinity

KW - Mobility

KW - Organic semiconductor

KW - Thin film transistor

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Liquid crystalline dialkyl-substituted thienylethenyl [1] benzothieno[3,2-b] benzothiophene derivatives for organic thin film transistors

Abstract

Bibliographical note

Keywords

ASJC Scopus subject areas

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