Thieno[3,2‑b]thiophene-Substituted Benzo[1,2‑b:4,5‑b′]dithiophene as a Promising Building Block for Low Bandgap Semiconducting Polymers for High-Performance Single and Tandem Organic Photovoltaic Cells
We designed and synthetized a new poly{4,8-bis((2-ethylhexyl)thieno[3,2-b]thiophene)-benzo[1,2-b:4,5-b′]dithiophene-alt-2-ethylhexyl-4,6-dibromo-3-fluorothieno[3,4-b]thiophene-2-carboxylate} (PTTBDT-FTT) comprising bis(2-ethylhexylthieno[3,2-b]thiophenylbenzo[1,2-b:4,5-b′]dithiophene (TTBD...
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Published in | Chemistry of materials Vol. 26; no. 2; pp. 1234 - 1242 |
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Main Authors | , , , , , |
Format | Journal Article |
Language | English |
Published |
American Chemical Society
28.01.2014
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Online Access | Get full text |
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Abstract | We designed and synthetized a new poly{4,8-bis((2-ethylhexyl)thieno[3,2-b]thiophene)-benzo[1,2-b:4,5-b′]dithiophene-alt-2-ethylhexyl-4,6-dibromo-3-fluorothieno[3,4-b]thiophene-2-carboxylate} (PTTBDT-FTT) comprising bis(2-ethylhexylthieno[3,2-b]thiophenylbenzo[1,2-b:4,5-b′]dithiophene (TTBDT) and 2-ethylhexyl 3-fluorothieno[3,4-b]thiophene-2-carboxylate (FTT). The optical bandgap of PTTBDT-FTT was 1.55 eV. The energy levels of the highest occupied and lowest unoccupied molecular orbitals of PTTBDT-FTT were −5.31 and −3.73 eV, respectively. Two-dimensional grazing-incidence X-ray scattering measurements showed that the film’s PTTBDT-FTT chains are predominantly arranged with a face-on orientation with respect to the substrate, with strong π–π stacking. An organic thin-film transistor fabricated using PTTBDT-FTT as the active semiconductor showed high hole mobility of 2.1 × 10–2 cm2/(V·s). Single-junction bulk heterojunction photovoltaic cells with the configuration ITO/PEDOT:PSS/PTTBDT-FTT:PC71BM/Ca/Al were fabricated, which showed a maximum power conversion efficiency (PCE) of 7.44%. Inverted photovoltaic cells with the structure ITO/PEIE/PTTBDT-FTT:PC71BM/MoO3/Ag were also fabricated, with a maximum PCE of 7.71%. A tandem photovoltaic device comprising the inverted PTTBDT-FTT:PC71BM cell and a P3HT:ICBA-based cell as the top and bottom cell components, respectively, showed a maximum PCE of 8.66%. This work demonstrated that the newly developed PTTBDT-FTT polymer was very promising for applications in both single and tandem solar cells. Furthermore, this work highlighted the fact that an extended π-system in the electron-donor moiety in low bandgap polymers is crucial for improving polymer solar cells. |
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AbstractList | We designed and synthetized a new poly{4,8-bis((2-ethylhexyl)thieno[3,2-b]thiophene)-benzo[1,2-b:4,5-b′]dithiophene-alt-2-ethylhexyl-4,6-dibromo-3-fluorothieno[3,4-b]thiophene-2-carboxylate} (PTTBDT-FTT) comprising bis(2-ethylhexylthieno[3,2-b]thiophenylbenzo[1,2-b:4,5-b′]dithiophene (TTBDT) and 2-ethylhexyl 3-fluorothieno[3,4-b]thiophene-2-carboxylate (FTT). The optical bandgap of PTTBDT-FTT was 1.55 eV. The energy levels of the highest occupied and lowest unoccupied molecular orbitals of PTTBDT-FTT were −5.31 and −3.73 eV, respectively. Two-dimensional grazing-incidence X-ray scattering measurements showed that the film’s PTTBDT-FTT chains are predominantly arranged with a face-on orientation with respect to the substrate, with strong π–π stacking. An organic thin-film transistor fabricated using PTTBDT-FTT as the active semiconductor showed high hole mobility of 2.1 × 10–2 cm2/(V·s). Single-junction bulk heterojunction photovoltaic cells with the configuration ITO/PEDOT:PSS/PTTBDT-FTT:PC71BM/Ca/Al were fabricated, which showed a maximum power conversion efficiency (PCE) of 7.44%. Inverted photovoltaic cells with the structure ITO/PEIE/PTTBDT-FTT:PC71BM/MoO3/Ag were also fabricated, with a maximum PCE of 7.71%. A tandem photovoltaic device comprising the inverted PTTBDT-FTT:PC71BM cell and a P3HT:ICBA-based cell as the top and bottom cell components, respectively, showed a maximum PCE of 8.66%. This work demonstrated that the newly developed PTTBDT-FTT polymer was very promising for applications in both single and tandem solar cells. Furthermore, this work highlighted the fact that an extended π-system in the electron-donor moiety in low bandgap polymers is crucial for improving polymer solar cells. |
Author | Kim, BongSoo Shin, Won Suk Hwang, Do-Hoon Song, Chang Eun Kim, Ji-Hoon Kang, In-Nam |
AuthorAffiliation | Department of Chemistry Korea Research Institute of Chemical Technology Department of Chemistry and Chemistry Institute for Functional Materials Korea Institute of Science and Technology (KIST) Energy Materials Research Center KAIST Pusan National University Department of Materials Science and Engineering The Catholic University of Korea Photoelectronic Hybrids Research Center |
AuthorAffiliation_xml | – name: Korea Institute of Science and Technology (KIST) – name: The Catholic University of Korea – name: Department of Chemistry – name: KAIST – name: Photoelectronic Hybrids Research Center – name: Pusan National University – name: Korea Research Institute of Chemical Technology – name: Department of Chemistry and Chemistry Institute for Functional Materials – name: Department of Materials Science and Engineering – name: Energy Materials Research Center |
Author_xml | – sequence: 1 givenname: Ji-Hoon surname: Kim fullname: Kim, Ji-Hoon – sequence: 2 givenname: Chang Eun surname: Song fullname: Song, Chang Eun – sequence: 3 givenname: BongSoo surname: Kim fullname: Kim, BongSoo – sequence: 4 givenname: In-Nam surname: Kang fullname: Kang, In-Nam – sequence: 5 givenname: Won Suk surname: Shin fullname: Shin, Won Suk – sequence: 6 givenname: Do-Hoon surname: Hwang fullname: Hwang, Do-Hoon email: dohoonhwang@pusan.ac.kr |
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Title | Thieno[3,2‑b]thiophene-Substituted Benzo[1,2‑b:4,5‑b′]dithiophene as a Promising Building Block for Low Bandgap Semiconducting Polymers for High-Performance Single and Tandem Organic Photovoltaic Cells |
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