2,1,3-Benzothiadiazole-5,6-dicarboxylic imide based low-bandgap polymers for solution processed photodiode application

Ye, Bin; Zhou, X. K.; Ye, Xichong; Zhang, Jie; Yang, Dezhi; Ma, Dongge; Wan, Xinhua

doi:10.1016/j.orgel.2015.07.051

Cited by 20 publications

(8 citation statements)

References 42 publications

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“…Recently much effort has been made in the development of polymer photodiodes with broad spectral response, mainly through the design and synthesis of new donor‐type polymers, acceptor, and interlayer materials and modification of device structures . In 2015, Zhang et al reported polymer photodiodes with low dark current using donor polymers with the 3,4‐ethylenedioxythiophene moiety as side chains .…”

Section: Introductionmentioning

confidence: 99%

Low‐Bandgap Polymers for High‐Performance Photodiodes with Maximal EQE near 1200 nm and Broad Spectral Response from 300 to 1700 nm

Han

Yang

et al. 2018

Advanced Optical Materials

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Polymer photodiodes with broad spectral response above 1500 nm can be used for imaging in the near‐infrared window of the atmosphere. Three low‐bandgap polymers based on 3,6‐dithiophen‐2‐yl‐2,5‐dihydropyrrolo[3,4‐c]pyrrole‐1,4‐dione (DPP), [1,2,5]thiadiazolo[3,4‐g]quinoxaline (TQ), benzobisthiadiazole (BBT), and dithienopyrrole (DTP) are designed and synthesized. No‐gain and gain polymer photodiodes with polymers:PC71BM as active layer materials and with aluminum doped ZnO nanoparticles:2,9‐bis(3‐(dimethylamino)propyl)anthra[2,1,9‐def:6,5,10‐d′e′f′]diisoquinoline‐1,3,8,10(2H,9H)‐tetraone (AZO:PDIN), MoO3, and 2,9‐dimethyl‐4,7‐diphenyl‐1,10‐phenanthroline (BCP) as interlayer materials are prepared. No‐gain photodiodes based on polymer P1 exhibit the external quantum efficiency (EQE) of 7.8% at 1200 nm, which is among the best values of polymer photodiodes known to date. Gain photodiodes based on P1 and P3 also exhibit a maximal EQE near 1200 nm. In addition, gain photodiodes based on P1 have a specific detectivity over 1013 Jones in 300–1360 nm and spectral response in the region of 300–1700 nm.

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Section: Introductionmentioning

confidence: 99%

Low‐Bandgap Polymers for High‐Performance Photodiodes with Maximal EQE near 1200 nm and Broad Spectral Response from 300 to 1700 nm

Han

Yang

et al. 2018

Advanced Optical Materials

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“…π-Conjugated molecules and polymers comprising electron-accepting (A) and electron-donating (D) units in the core or main chain are among the most performing semiconductor families spanning applications from electronic circuits and sensors based on organic thin-film transistors (OTFTs), − photovoltaic cells such as the bulk-heterojunction (BHJ-OSC) − and dye-sensitized (DSSC) devices, − photodetectors, − and thermoelectrics. − Among the electron accepting functionalities, benzo[ d ][2,1,3]thiadiazole (BT) and its halogenated derivatives, have realized several D–A polymers with remarkable performance (Figure ). − For instance, BT-based small-molecules and polymers have shown maximum OTFT hole mobilities of 0.20 and 1.92 cm 2 /(V s), , respectively, as well as BHS-OSCs and DSSCs with power conversion efficiencies as large as 11.7 and 7.1%, respectively. , Photodetectors with detectivity of ∼10 12 Jones , and thermoelectric devices with a Seebeck coefficient ( Z ) of 230 μV/K have also been demonstrated. , …”

Section: Introductionmentioning

confidence: 99%

“…41−53 For instance, BT-based small-molecules and polymers have shown maximum OTFT hole mobilities of 0.20 and 1.92 cm 2 /(V s), 41,51 respectively, as well as BHS-OSCs and DSSCs with power conversion efficiencies as large as 11.7 and 7.1%, respectively. 42,53 Photodetectors with detectivity of ∼10 12 Jones 54,55 and thermoelectric devices with a Seebeck coefficient (Z) of 230 μV/K have also been demonstrated. 56,57 The commercial availability of BT, synthetic access to the halogenated precursors, and facile bromination at the 4,7 BT positions have greatly facilitated the availability of this core.…”

Section: ■ Introductionmentioning

confidence: 99%

Benzo[d][1,2,3]thiadiazole (isoBT): Synthesis, Structural Analysis, and Implementation in Semiconducting Polymers

et al. 2016

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Benzo[d][2,1,3]thiadiazole (BT) is a markedly electron-deficient heterocycle widely employed in the realization of organic semiconductors for applications spanning transistors, solar cells, photodetectors, and thermoelectrics. In this contribution, we implement the corresponding isomer, benzo [d][1,2,3]thiadiazole (isoBT), along with new 6-fluoro-isoBT and 5,6-difluoro-isoBT units as synthons for constructing alternating copolymers with tetrathiophene (P1−P3). New isoBT-based small molecules as well as the corresponding BTquaterthiophene based polymers (P4−P6) are synthesized and characterized to probe architectural, electronic structural, and device performance differences between the two families. The results demonstrate that isoBT complements BT in enabling highperformance optoelectronic semiconductors with P3 exhibiting hole mobilities surpassing 0.7 cm 2 /(V s) in field-effect transistors and power conversion efficiencies of 9% in bulk-heterojunction solar cells.

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“…In this work, 2,1,3-benzothiadiazole-5,6-dicarboxylicimide (BTZI, Scheme ) is chosen as the strong electron-withdrawing unit and is synthesized by introducing a cyclic imide into the 5 and 6 positions of the benzothiadiazole (BTZ) moiety. The attachment of the imide group leads to BTZI with a stronger electron-withdrawing capability versus that of the well-known acceptor BTZ. ,− Furthermore, the solubility of BTZI-based polymers can be greatly increased compared to that of polymers based on BTZ units due to the incorporation of an alkyl solubilizing group on the imide moiety in the BTZI unit. In comparison to phthalimide, the incorporation of thiadiazole affords BTZI with improved physicochemical properties.…”

Section: Introductionmentioning

confidence: 99%

2,1,3-Benzothiadiazole-5,6-dicarboxylicimide-Based Polymer Semiconductors for Organic Thin-Film Transistors and Polymer Solar Cells

Ornelas

Tang

et al. 2017

ACS Appl. Mater. Interfaces

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A series of polymer semiconductors incorporating 2,1,3-benzothiadiazole-5,6-dicarboxylicimide (BTZI) as strong electron-withdrawing unit and an alkoxy-functionalized head-to-head linkage containing bithiophene or bithiazole as highly electron-rich co-unit are designed and synthesized. Because of the strong intramolecular charge transfer characteristics, all three polymers BTZI-TRTOR (P1), BTZI-BTOR (P2), and BTZI-BTzOR (P3) exhibit narrow bandgaps of 1.13, 1.05, and 0.92 eV, respectively, resulting in a very broad absorption ranging from 350 to 1400 nm. The highly electron-deficient 2,1,3-benzothiadiazole-5,6-dicarboxylicimide and alkoxy-functionalized bithiophene (or thiazole) lead to polymers with low-lying lowest unoccupied molecular orbitals (-3.96 to -4.28 eV) and high-lying highest occupied molecular orbitals (-5.01 to -5.20 eV). Hence, P1 and P3 show substantial and balanced ambipolar transport with electron mobilities/hole mobilities of up to 0.86/0.51 and 0.95/0.50 cm V s, respectively, and polymer P2 containing the strongest donor unit exhibited unipolar p-type performance with an average hole mobility of 0.40 cm V s in top-gate/bottom-contact thin-film transistors with gold as the source and drain electrodes. When incorporated into bulk heterojunction polymer solar cells, the narrow bandgap (1.13 eV) polymer P1 shows an encouraging power conversion efficiency of 4.15% with a relatively large open-circuit voltage of 0.69 V, which corresponds to a remarkably small energy loss of 0.44 eV. The power conversion efficiency of P1 is among the highest reported to date with such a small energy loss in polymer:fullerene solar cells.

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2,1,3-Benzothiadiazole-5,6-dicarboxylic imide based low-bandgap polymers for solution processed photodiode application

Cited by 20 publications

References 42 publications

Low‐Bandgap Polymers for High‐Performance Photodiodes with Maximal EQE near 1200 nm and Broad Spectral Response from 300 to 1700 nm

Low‐Bandgap Polymers for High‐Performance Photodiodes with Maximal EQE near 1200 nm and Broad Spectral Response from 300 to 1700 nm

Benzo[d][1,2,3]thiadiazole (isoBT): Synthesis, Structural Analysis, and Implementation in Semiconducting Polymers

2,1,3-Benzothiadiazole-5,6-dicarboxylicimide-Based Polymer Semiconductors for Organic Thin-Film Transistors and Polymer Solar Cells

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