Wide Band Gap Non‐Fullerene Small Molecular Acceptors Containing Spirobifluorene and Benzotriazole with Three Different End‐Capped Groups for P3HT‐Based Organic Solar Cells

Wen, Xiaoyu; Xiao, Bo; Tang, Ailing; Hu, Jie; Yang, Chunhe; Zhou, Erjun

doi:10.1002/cjoc.201700792

Cited by 15 publications

(10 citation statements)

References 49 publications

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“…With regard to a complementary absorption in the BHJ active layer, MBG SMAs can pair with a polymer donor with a wide band gap or a low band gap even with an MBG one. As a result, the MBG SMAs have been utilized in binary devices, − ternary devices, , as well as tandem architecture devices, indicating a versatility of this kind of acceptors. Here, we summarized the device performance results of PSCs based on the previously reported MBG SMAs as manifested in Figure and Table S1 in the Supporting Information. ,,− One can find that most of MBG SMAs just showed moderate performance with a PCE below 7% in a BHJ binary device.…”

Section: Introductionmentioning

confidence: 99%

Nonhalogenated-Solvent-Processed Efficient Polymer Solar Cells Enabled by Medium-Band-Gap A−π–D−π–A Small-Molecule Acceptors Based on a 6,12-Dihydro-diindolo[1,2-b:10,20-e]pyrazine Unit

Chen

Zeng

Weng

et al. 2019

ACS Appl. Mater. Interfaces

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In this contribution, a series of A−π−D−π−A small molecules (SMs), IPY-T-IC, IPY-T-ICCl, and IPY-T-ICF, containing the central donor unit (D) of 6,12-dihydrodiindolo[1,2-b:10,20-e]pyrazine (IPY), the π-conjugated bridge of thiophene, and the end-accepting group (A) of 3-(dic yanomethylidene)indol-1-one, 5,6-dichloro-3-(dicyanomethylidene)indol-1-one, or 5,6-difluoro-3-(dicyanomethylene)indol-1-one, were developed, characterized, and employed as the acceptor materials for polymer solar cells (PSCs). Influences of the different end-accepting groups on thermal properties, spectral absorption, energy levels, photovoltaic performance, and film morphology of these small-molecule acceptors (SMAs) were investigated in detail. These SMAs exhibit an excellent thermal stability and strong crystallization. The absorption spectra of these SMs mainly locate the wavelength between 400 and 700 nm, associated with the optical band gaps in the range of 1.75−1.90 eV. Compared with nonhalogenated IPY-T-IC, the halogenated SMAs IPY-T-ICCl and IPY-T-ICF present better absorption abilities, wider absorption region, and downshifted highest occupied molecular orbital (HOMO)/lowest unoccupied molecular orbital (LUMO) levels.With regard to the complementary spectral absorption and matched HOMO/LUMO levels, PTB7-Th as a low-band gap polymer was chosen to be an electron donor to pair with these SMAs for fabricating bulk-heterojuntion PSCs. Under optimized conditions, among these SMAs, the PTB7-Th:IPY-T-IC-based PSC processed from a halogenated solvent system (chlorobenzene + 1-chloronaphthalene) delivers the best power conversion efficiency (PCE) of 7.32%, mainly because of more complementary spectral absorption, upper-lying LUMO level, higher and balanced carrier mobility, more efficiently suppressed trap-assisted recombination, better charge collection property, and blend morphology. Encouragingly, an improved PCE of up to 7.68% is achieved when the IPY-T-IC-based solar cell was processed from a nonhalogenated solvent system (oxylene + 2-methylnaphthalene). In view of the large band gap of these IPY-based SMAs, the PCE of over 7.5% is notable and attractive for the related community. Our study argues that the IPY moiety is a potential electron-donating building moiety to develop medium-band-gap high-performance A−π−D−π−A SMAs for nonhalogenated-solvent-processed photovoltaic devices.

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Section: Introductionmentioning

confidence: 99%

Nonhalogenated-Solvent-Processed Efficient Polymer Solar Cells Enabled by Medium-Band-Gap A−π–D−π–A Small-Molecule Acceptors Based on a 6,12-Dihydro-diindolo[1,2-b:10,20-e]pyrazine Unit

Chen

Zeng

Weng

et al. 2019

ACS Appl. Mater. Interfaces

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“…Later on, they also fabricated PBDB-T:PTB7-Th:SFBRCN based ternary OSCs, showing an impressive PCE of 12.27% [102]. Based on this, Wen et al [103] prepared two BTA-bridged 3D acceptors, BTA21 and BTA23 (Scheme 6, Table 5), having wide optical bandgaps of 2.19 and 2.15 eV, respectively. Compared with BTA23, the resulting BTA21 based OSCs showed a better PCE of a) Measured by CV based on films.…”

Section: Scheme 6 Chemical Structures Of A-d-a-type 3d Rd-based Nfasmentioning

confidence: 99%

Rhodanine-based nonfullerene acceptors for organic solar cells

Liu¹,

Li²,

Zhao

2019

Sci. China Mater.

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Significant progress on the development of nonfullerene acceptors (NFAs) for organic solar cells (OSCs) has been made in the past several years, and the power conversion efficiency (PCE) exceeding 17% has been already realized based on a tandem non-fullerene device. To date, NFAs with a linearly fused acceptor-donor-acceptor (A-D-A) structure are of great interest, due to their attracting synthetic flexibility and high photovoltaic performance. Rhodanine is one of the most studied electron-withdrawing moieties to construct such AD A type NFAs, and the resulting single-junction OSCs have produced PCEs of~10%. More interestingly, those rhodanine-based NFAs have demonstrated a particularly excellent compatibility with well-known P3HT donor, enabling respectable PCEs over 7%. Thus in this review, we summarize the important advances on rhodanine-based NFAs with a main focus on discussing the molecular design strategies, providing a better understanding of the structure-property relationship for those rhodanine-based NFAs.

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“…进一步地, 将二氰甲烯基(dicyanomethylene)引入至末端 A 单元, 得到二氰基绕丹宁(2-(1,1-dicyanomethylene)rhodanine, RCN), 进而合成了 BTA3(图 19d) [129] . 在 BTA1、BTA3 的基础上, 周二军等 [130] 以螺二芴 (spirobifluorene, SF)为中心给体"D"单元, 设计合成了 BTA21、 BTA23 和 BTA27(图 19f), 探讨不同的末端 "A" 单元对光伏性能的影响. 研究结果表明, 末端单元对分子吸收谱带、能级以及共混薄膜形貌有显著的影响, 其中 BTA21 的光伏性能最为优异, 基于 P3HT/BTA21 (w/w, 1∶1, 0.8 vol% CN)器件的 V oc 为 1.02 V, J sc 为 5.5 mA/cm 2 , FF 为 59.0%, PCE 为 3.28%.…”

Section: Bta 系列受体材料unclassified

Research Advances on Benzotriazole-based Organic Photovoltaic Materials

Bai¹,

Xue²,

Wang³

et al. 2021

Acta Chimica Sinica

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Over the past two decades, organic solar cells (OSCs) have been developed rapidly with the power conversion efficiency rapidly rising from less than 5% to over 18%, which is mainly promoted by the development of various new donor and acceptor materials. As a typical electron-deficient penta-heterocycle, benzotriazoles (BTAs) derivates a variety of high-performance photovoltaic materials, including polymer donor, small-molecule donor materials, as well as non-fullerenes acceptor and polymer acceptor. Among them, the J series of polymer donors and Y series of non-fullerenes acceptors are typical examples, and thus are specially highlighted in this review. Meanwhile, molecular design strategies of those BTA-based photovoltaic materials have also been discussed. It shows that donor-acceptor (D-A) conjugated strategy is still the most efficient thus far, where A units is the BTA unit or its derivatives, and D units commonly used in BTA-based photovoltaic materials are benzodithiophene, benzodifuran, dithienosilole, indacenodithiophene, thiophene, etc. The D-A strategy is both applied for donor molecules (with the molecular structure of D-A, D-π-A-π, D-A-D-A-D, etc.), and for acceptor molecules (with the molecular structure of A-D-A, A-π-D-π-A, A-DAD-A, etc.). By adjusting their molecular structures and/or pairing of differential D and A units, various properties such as absorption band and energy levels of molecules, as well as the morphology and charge carrier mobilities in OSCs can be well controlled. Furthermore, through side-chain engineering, such as flexible side-chains (alkyl, alkoxy, alkylthiol, alkylsilyl, etc.), conjugated side-chains (substituted-thiophene or benzene, etc.), electron-withdrawing groups (F atoms, Cl atoms, dicyanomethylene, etc.), their photovoltaic properties can be further regulated. Here, this review focuses on the research progress on BTA-based photovoltaic materials and related molecular design strategies developed in recent years, and also presents perspective on its future development.

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Wide Band Gap Non‐Fullerene Small Molecular Acceptors Containing Spirobifluorene and Benzotriazole with Three Different End‐Capped Groups for P3HT‐Based Organic Solar Cells

Cited by 15 publications

References 49 publications

Nonhalogenated-Solvent-Processed Efficient Polymer Solar Cells Enabled by Medium-Band-Gap A−π–D−π–A Small-Molecule Acceptors Based on a 6,12-Dihydro-diindolo[1,2-b:10,20-e]pyrazine Unit

Nonhalogenated-Solvent-Processed Efficient Polymer Solar Cells Enabled by Medium-Band-Gap A−π–D−π–A Small-Molecule Acceptors Based on a 6,12-Dihydro-diindolo[1,2-b:10,20-e]pyrazine Unit

Rhodanine-based nonfullerene acceptors for organic solar cells

Research Advances on Benzotriazole-based Organic Photovoltaic Materials

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