Optimizing the π-Bridge of Non-fullerene Acceptors to Suppress Dark Current in NIR Organic Photodetectors

doi:10.1007/s40242-024-4103-8

高等学校化学研究 ›› 2024, Vol. 40 ›› Issue (4): 712-721.doi: 10.1007/s40242-024-4103-8

Optimizing the π-Bridge of Non-fullerene Acceptors to Suppress Dark Current in NIR Organic Photodetectors

SHAO Lin¹, HUANG Yijun¹, HONG Ling¹, XU Zishuo¹, YANG Xiye^1,2, LIU Chunchen¹, HUANG Fei¹, CAO Yong¹

1. State Key Laboratory of Luminescent Materials and Devices, Institute of Polymer Optoelectronic Materials and Devices, School of Materials Science and Engineering, South China University of Technology, Guangzhou 510640, P. R. China;
2. Lumidar Technology Co., Ltd., Guangzhou 510530, P. R. China

收稿日期:2024-04-22 出版日期:2024-08-01 发布日期:2024-07-24
通讯作者: LIU Chunchen,mscliu@scut.edu.cn;YANG Xiye,xyyang@lumidartech.com;HUANG Fei,msfhuang@scut.edu.cn E-mail:mscliu@scut.edu.cn;xyyang@lumidartech.com;msfhuang@scut.edu.cn
基金资助:
This work was supported by the National Natural Science Foundation of China (Nos. U21A6002, 51933003, 52203355), the Basic and Applied Basic Research Foundation of Guangdong Province, China (Nos. 2019B030302007, 2023A1515012293) and the Guangzhou Science and Technology Plan Project, China (No. 2023A04J0970).

Optimizing the π-Bridge of Non-fullerene Acceptors to Suppress Dark Current in NIR Organic Photodetectors

SHAO Lin¹, HUANG Yijun¹, HONG Ling¹, XU Zishuo¹, YANG Xiye^1,2, LIU Chunchen¹, HUANG Fei¹, CAO Yong¹

1. State Key Laboratory of Luminescent Materials and Devices, Institute of Polymer Optoelectronic Materials and Devices, School of Materials Science and Engineering, South China University of Technology, Guangzhou 510640, P. R. China;
2. Lumidar Technology Co., Ltd., Guangzhou 510530, P. R. China

Received:2024-04-22 Online:2024-08-01 Published:2024-07-24
Contact: LIU Chunchen,mscliu@scut.edu.cn;YANG Xiye,xyyang@lumidartech.com;HUANG Fei,msfhuang@scut.edu.cn E-mail:mscliu@scut.edu.cn;xyyang@lumidartech.com;msfhuang@scut.edu.cn
Supported by:
This work was supported by the National Natural Science Foundation of China (Nos. U21A6002, 51933003, 52203355), the Basic and Applied Basic Research Foundation of Guangdong Province, China (Nos. 2019B030302007, 2023A1515012293) and the Guangzhou Science and Technology Plan Project, China (No. 2023A04J0970).

摘要/Abstract

摘要： Recently, the rapid development of non-fullerene acceptors (NFAs) has laid the foundation for performance improvements in near-infrared (NIR) organic photodetectors (OPDs). However, reducing the bandgap of NFAs to achieve strong absorption in the shorter-wave region usually leads to increased dark current density (J_d) and decreased responsivity (R), severely limiting the detectivity (D^*) of NIR-OPDs. To date, it remains challenging to manipulate the J_d of NIR-OPDs through rational structure engineering of NFAs. Herein, three NIR-NFAs, namely bis(2-decyltetradecyl)4,4′-(2′,7′-di- tert-butylspiro[cyclopenta[2,1-b:3,4-b′]dithiophene-4,9′-fluorene]- 2,6-diyl)bis(6-(((Z)-1-(dicyanomethylene)-5,6-difluoro-3-oxo-1,3- dihydro-2H-inden-2-ylidene)methyl)thieno[3,4-b]thiophene-2- carboxylate) (TSIC-4F), bis(2-decyltetradecyl)6,6′-(2′,7′-di-tert- butylspiro[cyclopenta[2,1-b:3,4-b′]dithiophene-4,9′-fluorene]-2,6- diyl)bis(4-(((Z)-1-(dicyanomethylene)-5,6-difluoro-3-oxo-1,3-dihydro- 2H-inden-2-ylidene)methyl)thieno[3,4-b]thiophene-2-carboxylate) (STIC-4F), and 2,2′-((2Z,2′Z)-(((2′,7′-di-tert-butylspiro[cyclopenta [2,1-b:3,4-b′]dithiophene-4,9′-fluorene]-2,6-diyl)bis(2,3-bis(5-(2- butyloctyl)thiophen-2-yl)thieno[3,4-b]pyrazine-7,5-diyl))bis(metha- neylylidene))bis(5,6-difluoro-3-oxo-2,3-dihydro-1H-indene-2,1- diylidene))dimalononitrile (TPIC-4F), were designed using the thieno[3,4-b]thiophene (TT) and thieno[3,4-b]pyrazine (TPy) derivatives as the π-bridge. Owing to the intramolecular S-S and S-N interactions, STIC-4F and TPIC-4F exhibited smaller backbone distortions than TSIC-4F. A significantly red-shifted absorption with a peak at 1015 nm was observed in TPIC-4F film, larger than that (ca. 960 nm) for TSIC-4F and STIC-4F films. Moreover, OPDs operating in a photovoltaic mode were successfully fabricated, and TPIC-4F-based OPDs achieved the lowest J_d of 3.18×10^‒8 A/cm² at ‒0.1 V. Impressively, although TPIC-4F-based OPDs exhibited the lowest R, higher shot-noise-limited specific detectivity (D_sh^*) in 1000—1200 nm could be achieved due to its lowest J_d. This study underscored the effectiveness of optimizing the π-bridge structure of NFAs to suppress J_d, ultimately attaining higher D_sh^* in the NIR region.

关键词: π-Bridge, Near-infrared, Non-fullerene acceptor, Dark current, Organic photodetector

Abstract: Recently, the rapid development of non-fullerene acceptors (NFAs) has laid the foundation for performance improvements in near-infrared (NIR) organic photodetectors (OPDs). However, reducing the bandgap of NFAs to achieve strong absorption in the shorter-wave region usually leads to increased dark current density (J_d) and decreased responsivity (R), severely limiting the detectivity (D^*) of NIR-OPDs. To date, it remains challenging to manipulate the J_d of NIR-OPDs through rational structure engineering of NFAs. Herein, three NIR-NFAs, namely bis(2-decyltetradecyl)4,4′-(2′,7′-di- tert-butylspiro[cyclopenta[2,1-b:3,4-b′]dithiophene-4,9′-fluorene]- 2,6-diyl)bis(6-(((Z)-1-(dicyanomethylene)-5,6-difluoro-3-oxo-1,3- dihydro-2H-inden-2-ylidene)methyl)thieno[3,4-b]thiophene-2- carboxylate) (TSIC-4F), bis(2-decyltetradecyl)6,6′-(2′,7′-di-tert- butylspiro[cyclopenta[2,1-b:3,4-b′]dithiophene-4,9′-fluorene]-2,6- diyl)bis(4-(((Z)-1-(dicyanomethylene)-5,6-difluoro-3-oxo-1,3-dihydro- 2H-inden-2-ylidene)methyl)thieno[3,4-b]thiophene-2-carboxylate) (STIC-4F), and 2,2′-((2Z,2′Z)-(((2′,7′-di-tert-butylspiro[cyclopenta [2,1-b:3,4-b′]dithiophene-4,9′-fluorene]-2,6-diyl)bis(2,3-bis(5-(2- butyloctyl)thiophen-2-yl)thieno[3,4-b]pyrazine-7,5-diyl))bis(metha- neylylidene))bis(5,6-difluoro-3-oxo-2,3-dihydro-1H-indene-2,1- diylidene))dimalononitrile (TPIC-4F), were designed using the thieno[3,4-b]thiophene (TT) and thieno[3,4-b]pyrazine (TPy) derivatives as the π-bridge. Owing to the intramolecular S-S and S-N interactions, STIC-4F and TPIC-4F exhibited smaller backbone distortions than TSIC-4F. A significantly red-shifted absorption with a peak at 1015 nm was observed in TPIC-4F film, larger than that (ca. 960 nm) for TSIC-4F and STIC-4F films. Moreover, OPDs operating in a photovoltaic mode were successfully fabricated, and TPIC-4F-based OPDs achieved the lowest J_d of 3.18×10^‒8 A/cm² at ‒0.1 V. Impressively, although TPIC-4F-based OPDs exhibited the lowest R, higher shot-noise-limited specific detectivity (D_sh^*) in 1000—1200 nm could be achieved due to its lowest J_d. This study underscored the effectiveness of optimizing the π-bridge structure of NFAs to suppress J_d, ultimately attaining higher D_sh^* in the NIR region.

Key words: π-Bridge, Near-infrared, Non-fullerene acceptor, Dark current, Organic photodetector

SHAO Lin, HUANG Yijun, HONG Ling, XU Zishuo, YANG Xiye, LIU Chunchen, HUANG Fei, CAO Yong. Optimizing the π-Bridge of Non-fullerene Acceptors to Suppress Dark Current in NIR Organic Photodetectors[J]. 高等学校化学研究, 2024, 40(4): 712-721.

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Optimizing the π-Bridge of Non-fullerene Acceptors to Suppress Dark Current in NIR Organic Photodetectors

Optimizing the π-Bridge of Non-fullerene Acceptors to Suppress Dark Current in NIR Organic Photodetectors

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