Synthesis of organic semiconductor bearing B←N bridged thienylthiazole and diketopyrrolopyrrole for the applicaton of high open-circuit voltage organic photovoltaics

Ka Yeon Ryu; Dan Bi Sung; Suk Young Won; Ara Jo; Kyusang Ahn; Hyun Yeong Kim; Arulraj ArulKashmir; Kyungwon Kwak; Chongmok Lee; Won Suk Kim; Kyungkon Kim

doi:10.1016/j.dyepig.2017.11.060

Synthesis of organic semiconductor bearing B←N bridged thienylthiazole and diketopyrrolopyrrole for the applicaton of high open-circuit voltage organic photovoltaics

Ka Yeon Ryu, Dan Bi Sung, Suk Young Won, Ara Jo, Kyusang Ahn, Hyun Yeong Kim, Arulraj ArulKashmir, Kyungwon Kwak, Chongmok Lee, Won Suk Kim, Kyungkon Kim

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1 Citation (Scopus)

Abstract

New small molecular semiconductors with small band gap and low-lying highest occupied molecular orbital (E_HOMO), namely TBDPPOT, TBDPPEH, and TBDPPEHT4 were synthesized by incorporating the B←N bridged thienylthiazole and diketopyrrolopyrrole (DPP) derivatives. TBDPPOT and TBDPPEH were prepared, respectively, using two different DPPs having 1-octyl and 2-ethylhexyl moiety as the solubilizing group. In addition, the band gap of the TBDPPEH is further reduced by introducing planar thienothiophene unit, which was used for the preparation of TBDPPEHT4. These synthesized SMs are blended with fullerene derivative to construct a photo-active layer for organic photovoltaics. Among OPVs utilizing those SMs, the TBDPPEH exhibits highest power conversion efficiency of 3.21% with an exceptionally high V_OC of 0.92 V, which is ascribed to low-lying HOMO energy level of −5.62 eV. It is expected that the utilization of TBDPPEH as a photo-active layer for OPVs would enhance the oxidation stability of the OPVs.

Original language	English
Pages (from-to)	858-866
Number of pages	9
Journal	Dyes and Pigments
Volume	149
DOIs	https://doi.org/10.1016/j.dyepig.2017.11.060
Publication status	Published - 2018 Feb

Bibliographical note

Funding Information:
This research was supported by the Basic Science Research Program through the National Research Foundation of Korea ( 2015R1A1A1A05001334 , 2015M1A2A2057506 and 2016M1A2A2940914 ) and by Korea Institute of Energy Technology Evaluation and Planning (No. 20163030013900 ).

Publisher Copyright:
© 2017

ASJC Scopus subject areas

Chemical Engineering(all)
Process Chemistry and Technology

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10.1016/j.dyepig.2017.11.060

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Ryu, K. Y., Sung, D. B., Won, S. Y., Jo, A., Ahn, K., Kim, H. Y., ArulKashmir, A., Kwak, K., Lee, C., Kim, W. S., & Kim, K. (2018). Synthesis of organic semiconductor bearing B←N bridged thienylthiazole and diketopyrrolopyrrole for the applicaton of high open-circuit voltage organic photovoltaics. Dyes and Pigments, 149, 858-866. https://doi.org/10.1016/j.dyepig.2017.11.060

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title = "Synthesis of organic semiconductor bearing B←N bridged thienylthiazole and diketopyrrolopyrrole for the applicaton of high open-circuit voltage organic photovoltaics",

abstract = "New small molecular semiconductors with small band gap and low-lying highest occupied molecular orbital (EHOMO), namely TBDPPOT, TBDPPEH, and TBDPPEHT4 were synthesized by incorporating the B←N bridged thienylthiazole and diketopyrrolopyrrole (DPP) derivatives. TBDPPOT and TBDPPEH were prepared, respectively, using two different DPPs having 1-octyl and 2-ethylhexyl moiety as the solubilizing group. In addition, the band gap of the TBDPPEH is further reduced by introducing planar thienothiophene unit, which was used for the preparation of TBDPPEHT4. These synthesized SMs are blended with fullerene derivative to construct a photo-active layer for organic photovoltaics. Among OPVs utilizing those SMs, the TBDPPEH exhibits highest power conversion efficiency of 3.21% with an exceptionally high VOC of 0.92 V, which is ascribed to low-lying HOMO energy level of −5.62 eV. It is expected that the utilization of TBDPPEH as a photo-active layer for OPVs would enhance the oxidation stability of the OPVs.",

author = "Ryu, {Ka Yeon} and Sung, {Dan Bi} and Won, {Suk Young} and Ara Jo and Kyusang Ahn and Kim, {Hyun Yeong} and Arulraj ArulKashmir and Kyungwon Kwak and Chongmok Lee and Kim, {Won Suk} and Kyungkon Kim",

note = "Funding Information: This research was supported by the Basic Science Research Program through the National Research Foundation of Korea ( 2015R1A1A1A05001334 , 2015M1A2A2057506 and 2016M1A2A2940914 ) and by Korea Institute of Energy Technology Evaluation and Planning (No. 20163030013900 ). Publisher Copyright: {\textcopyright} 2017",

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doi = "10.1016/j.dyepig.2017.11.060",

language = "English",

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T1 - Synthesis of organic semiconductor bearing B←N bridged thienylthiazole and diketopyrrolopyrrole for the applicaton of high open-circuit voltage organic photovoltaics

AU - Ryu, Ka Yeon

AU - Sung, Dan Bi

AU - Won, Suk Young

AU - Jo, Ara

AU - Ahn, Kyusang

AU - Kim, Hyun Yeong

AU - ArulKashmir, Arulraj

AU - Kwak, Kyungwon

AU - Lee, Chongmok

AU - Kim, Won Suk

AU - Kim, Kyungkon

N1 - Funding Information: This research was supported by the Basic Science Research Program through the National Research Foundation of Korea ( 2015R1A1A1A05001334 , 2015M1A2A2057506 and 2016M1A2A2940914 ) and by Korea Institute of Energy Technology Evaluation and Planning (No. 20163030013900 ). Publisher Copyright: © 2017

PY - 2018/2

Y1 - 2018/2

N2 - New small molecular semiconductors with small band gap and low-lying highest occupied molecular orbital (EHOMO), namely TBDPPOT, TBDPPEH, and TBDPPEHT4 were synthesized by incorporating the B←N bridged thienylthiazole and diketopyrrolopyrrole (DPP) derivatives. TBDPPOT and TBDPPEH were prepared, respectively, using two different DPPs having 1-octyl and 2-ethylhexyl moiety as the solubilizing group. In addition, the band gap of the TBDPPEH is further reduced by introducing planar thienothiophene unit, which was used for the preparation of TBDPPEHT4. These synthesized SMs are blended with fullerene derivative to construct a photo-active layer for organic photovoltaics. Among OPVs utilizing those SMs, the TBDPPEH exhibits highest power conversion efficiency of 3.21% with an exceptionally high VOC of 0.92 V, which is ascribed to low-lying HOMO energy level of −5.62 eV. It is expected that the utilization of TBDPPEH as a photo-active layer for OPVs would enhance the oxidation stability of the OPVs.

AB - New small molecular semiconductors with small band gap and low-lying highest occupied molecular orbital (EHOMO), namely TBDPPOT, TBDPPEH, and TBDPPEHT4 were synthesized by incorporating the B←N bridged thienylthiazole and diketopyrrolopyrrole (DPP) derivatives. TBDPPOT and TBDPPEH were prepared, respectively, using two different DPPs having 1-octyl and 2-ethylhexyl moiety as the solubilizing group. In addition, the band gap of the TBDPPEH is further reduced by introducing planar thienothiophene unit, which was used for the preparation of TBDPPEHT4. These synthesized SMs are blended with fullerene derivative to construct a photo-active layer for organic photovoltaics. Among OPVs utilizing those SMs, the TBDPPEH exhibits highest power conversion efficiency of 3.21% with an exceptionally high VOC of 0.92 V, which is ascribed to low-lying HOMO energy level of −5.62 eV. It is expected that the utilization of TBDPPEH as a photo-active layer for OPVs would enhance the oxidation stability of the OPVs.

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DO - 10.1016/j.dyepig.2017.11.060

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AN - SCOPUS:85036621012

SN - 0143-7208

VL - 149

SP - 858

EP - 866

JO - Dyes and Pigments

JF - Dyes and Pigments

ER -

Synthesis of organic semiconductor bearing B←N bridged thienylthiazole and diketopyrrolopyrrole for the applicaton of high open-circuit voltage organic photovoltaics

Abstract

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