5′-(Anthracene-9,10-diyl)bis(ethyne-2,1-diyl)bis(2-hexylthiophene) derivatives bearing 5-ethynyl-5′-hexyl-2,2′-bithiophene and 2-ethynyl-5-hexylthieno[3,2-b]thiophene: Thin film transistors and photovoltaic applications

Soyoung Jo, Jicheol Shin, Suk Young Bae, Kyung Hwan Kim, Tae Wan Lee, Sunkyung Son, Kyungkon Kim, Dong Hoon Choi

Research output: Contribution to journalArticle

6 Citations (Scopus)

Abstract

Novel 5,5′-(anthracene-9,10-diyl)bis(ethyne-2,1-diyl)bis(2- hexylthiophene)-based conjugated molecules have been synthesized via the Sonogashira coupling reaction. Newly synthesized anthracene-based molecules exhibit good solubility in common organic solvents and good self-film-forming properties. The semiconducting properties of the two molecules were evaluated in organic thin film transistors (OTFTs). The two π-conjugated molecules 4 and 7 exhibit fairly high charge carrier mobilities - as high as 0.010-0.022 cm 2 V-1 s-1 (Ion/Ioff > 103) - without any annealing process. The high charge carrier mobilities of the as-spun films are attributed to the fact that the molecules demonstrated pronounced J-aggregation behavior, resulting in easy crystallization and dense coverage of the surface of a dielectric layer. In addition, two molecules were employed to fabricate organic photovoltaic (OPV) cells with methanofullerene [6,6]-phenyl C61-butyric acid methyl ester (PC 61BM) without thermal annealing. As a result, the photovoltaic cell containing 7 had the best preliminary results with an open-circuit voltage of 0.92 V, a short-circuit current density of 1.82 mA/cm2, and a fill factor of 0.32, offering an overall power conversion efficiency (PCE) of 0.54%.

Original languageEnglish
Pages (from-to)833-843
Number of pages11
JournalSynthetic Metals
Volume161
Issue number9-10
DOIs
Publication statusPublished - 2011 May 1

Fingerprint

Bearings (structural)
Thiophenes
Acetylene
Anthracene
Thiophene
Thin film transistors
anthracene
thiophenes
transistors
Derivatives
Molecules
thin films
molecules
Photovoltaic cells
photovoltaic cells
Carrier mobility
carrier mobility
Charge carriers
charge carriers
Annealing

Keywords

  • Anthracene
  • Bulk heterojunction
  • Conjugated molecules
  • Mobility
  • Organic thin film transistor
  • Photovoltaic cell
  • Semiconductor

ASJC Scopus subject areas

  • Mechanical Engineering
  • Mechanics of Materials
  • Materials Chemistry
  • Metals and Alloys
  • Electronic, Optical and Magnetic Materials
  • Condensed Matter Physics

Cite this

5′-(Anthracene-9,10-diyl)bis(ethyne-2,1-diyl)bis(2-hexylthiophene) derivatives bearing 5-ethynyl-5′-hexyl-2,2′-bithiophene and 2-ethynyl-5-hexylthieno[3,2-b]thiophene : Thin film transistors and photovoltaic applications. / Jo, Soyoung; Shin, Jicheol; Bae, Suk Young; Kim, Kyung Hwan; Lee, Tae Wan; Son, Sunkyung; Kim, Kyungkon; Choi, Dong Hoon.

In: Synthetic Metals, Vol. 161, No. 9-10, 01.05.2011, p. 833-843.

Research output: Contribution to journalArticle

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T1 - 5′-(Anthracene-9,10-diyl)bis(ethyne-2,1-diyl)bis(2-hexylthiophene) derivatives bearing 5-ethynyl-5′-hexyl-2,2′-bithiophene and 2-ethynyl-5-hexylthieno[3,2-b]thiophene

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AU - Jo, Soyoung

AU - Shin, Jicheol

AU - Bae, Suk Young

AU - Kim, Kyung Hwan

AU - Lee, Tae Wan

AU - Son, Sunkyung

AU - Kim, Kyungkon

AU - Choi, Dong Hoon

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N2 - Novel 5,5′-(anthracene-9,10-diyl)bis(ethyne-2,1-diyl)bis(2- hexylthiophene)-based conjugated molecules have been synthesized via the Sonogashira coupling reaction. Newly synthesized anthracene-based molecules exhibit good solubility in common organic solvents and good self-film-forming properties. The semiconducting properties of the two molecules were evaluated in organic thin film transistors (OTFTs). The two π-conjugated molecules 4 and 7 exhibit fairly high charge carrier mobilities - as high as 0.010-0.022 cm 2 V-1 s-1 (Ion/Ioff > 103) - without any annealing process. The high charge carrier mobilities of the as-spun films are attributed to the fact that the molecules demonstrated pronounced J-aggregation behavior, resulting in easy crystallization and dense coverage of the surface of a dielectric layer. In addition, two molecules were employed to fabricate organic photovoltaic (OPV) cells with methanofullerene [6,6]-phenyl C61-butyric acid methyl ester (PC 61BM) without thermal annealing. As a result, the photovoltaic cell containing 7 had the best preliminary results with an open-circuit voltage of 0.92 V, a short-circuit current density of 1.82 mA/cm2, and a fill factor of 0.32, offering an overall power conversion efficiency (PCE) of 0.54%.

AB - Novel 5,5′-(anthracene-9,10-diyl)bis(ethyne-2,1-diyl)bis(2- hexylthiophene)-based conjugated molecules have been synthesized via the Sonogashira coupling reaction. Newly synthesized anthracene-based molecules exhibit good solubility in common organic solvents and good self-film-forming properties. The semiconducting properties of the two molecules were evaluated in organic thin film transistors (OTFTs). The two π-conjugated molecules 4 and 7 exhibit fairly high charge carrier mobilities - as high as 0.010-0.022 cm 2 V-1 s-1 (Ion/Ioff > 103) - without any annealing process. The high charge carrier mobilities of the as-spun films are attributed to the fact that the molecules demonstrated pronounced J-aggregation behavior, resulting in easy crystallization and dense coverage of the surface of a dielectric layer. In addition, two molecules were employed to fabricate organic photovoltaic (OPV) cells with methanofullerene [6,6]-phenyl C61-butyric acid methyl ester (PC 61BM) without thermal annealing. As a result, the photovoltaic cell containing 7 had the best preliminary results with an open-circuit voltage of 0.92 V, a short-circuit current density of 1.82 mA/cm2, and a fill factor of 0.32, offering an overall power conversion efficiency (PCE) of 0.54%.

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