A Thieno[3,4-<i>b</i>]thiophene-Based Non-fullerene Electron Acceptor for High-Performance Bulk-Heterojunction Organic Solar Cells

Liu, Feng; Zhou, Zichun; Zhang, Cheng; Vergote, Thomas; Fan, Haijun; Zhu, Xiaozhang

doi:10.1021/jacs.6b08523

Cited by 287 publications

(185 citation statements)

References 47 publications

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“…Starting from 4-hexyl-4H-dithieno[3,2-b:2′,3′-d]pyrrole (1), the key intermediate compound 4 (INP) was constructed via a three-step procedure, i.e., stannylation, Stille coupling, and Friedel-Crafts intramolecular cyclization. [54] The detailed synthetic procedures and characterization including 1 H NMR, 13 C NMR, 19 Table 1). [54] The detailed synthetic procedures and characterization including 1 H NMR, 13 C NMR, 19 Table 1).…”

Section: Organic Solar Cellsmentioning

confidence: 99%

Dithieno[3,2‐b:2′,3′‐d]pyrrol Fused Nonfullerene Acceptors Enabling Over 13% Efficiency for Organic Solar Cells

et al. 2018

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A new electron-rich central building block, 5,5,12,12-tetrakis(4-hexylphenyl)-indacenobis-(dithieno[3,2-b:2',3'-d]pyrrol) (INP), and two derivative nonfullerene acceptors (INPIC and INPIC-4F) are designed and synthesized. The two molecules reveal broad (600-900 nm) and strong absorption due to the satisfactory electron-donating ability of INP. Compared with its counterpart INPIC, fluorinated nonfullerene acceptor INPIC-4F exhibits a stronger near-infrared absorption with a narrower optical bandgap of 1.39 eV, an improved crystallinity with higher electron mobility, and down-shifted highest occupied molecular orbital and lowest unoccupied molecular orbital energy levels. Organic solar cells (OSCs) based on INPIC-4F exhibit a high power conversion efficiency (PCE) of 13.13% and a relatively low energy loss of 0.54 eV, which is among the highest efficiencies reported for binary OSCs in the literature. The results demonstrate the great potential of the new INP as an electron-donating building block for constructing high-performance nonfullerene acceptors for OSCs.

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Section: Organic Solar Cellsmentioning

confidence: 99%

Dithieno[3,2‐b:2′,3′‐d]pyrrol Fused Nonfullerene Acceptors Enabling Over 13% Efficiency for Organic Solar Cells

et al. 2018

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“…Recently, the power conversion efficiency (PCE) of “polymer:nonfullerene” solar cells with nonfullerene‐type electron acceptors has reached ≈11–13% by introducing polymer donors with bithienylbenzodithiophene (BDTT)‐based units and nonfullerene acceptors with indacenodithienothiophene (IT)‐based derivatives 15, 16, 17, 18, 19. However, less attention has been paid to applying such interfacial layers for polymer:nonfullerene solar cells, particularly for the inverted‐type device structures that benefit from the use of stable top electrodes with high work functions including, e.g., silver (see Table S1 in the Supporting Information) 20, 21, 22, 23, 24, 25, 26, 27, 28, 29, 30…”

Section: Introductionmentioning

confidence: 99%

High‐Efficiency Polymer:Nonfullerene Solar Cells with Quaterthiophene‐Containing Polyimide Interlayers

et al. 2018

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Interfacial layers (interlayers) are one of the emerging approaches in organic solar cells with bulk heterojunction (BHJ) layers because the solar cell efficiency can be additionally improved by their presence. However, less attention is paid to the use of interlayers for polymer:nonfullerene solar cells, which have strong advantages over polymer:fullerene solar cells. In addition, most polymers used for the interlayers possess a low glass transition temperature (T g). Here, it is demonstrated that two types of quarterthiophene‐containing polyimides (PIs) with high T g (>198 °C), which are synthesized using pyromellitic dianhydride (PMDA) and cyclobutane‐1,2,3,4‐tetracarboxylic dianhydride (CTCDA), can act as an interfacial layer in the polymer:nonfullerene solar cells with the BHJ layers of poly[(2,6‐(4,8‐bis(5‐(2‐ethylhexyl)thiophen‐2‐yl)‐benzo[1,2‐b:4,5‐b′]dithiophene))‐alt‐(5,5‐(1′,3′‐di‐2‐thienyl‐5′,7′‐bis(2‐ethylhexyl)benzo[1′,2′‐c:4′,5′‐c′]dithiophene‐4,8‐dione))] (PBDB‐T) and 3,9‐bis(2‐methylene(3‐(1,1‐dicyanomethylene)‐indanone))‐5,5,11,11‐tetrakis(4‐hexylphenyl)‐dithieno[2,3‐d:2′,3′‐d′]‐s‐indaceno[1,2‐b:5,6‐b′]dithiophene) (ITIC), or (3‐(1,1‐dicyanomethylene)‐1‐methyl‐indanone)‐5,5,11,11‐tetrakis(4‐hexylphenyl)‐dithieno[2,3‐d:2′,3′‐d′]‐s‐indaceno[1,2‐b:5,6‐b′]‐dithiophene) (IT‐M). Interestingly, the efficiency and stability of devices are improved by the PMDA‐based PI interlayers with a stretched chain structure but degraded by the CTCDA‐based PI interlayers with a bended chain structure.

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“…[100][101][102] The PCEs of more than 12% have been realized for OSCs with small-area devices [34,[102][103][104][105][106][107] and PCEs from 8% to 10% have also been obtained in large-area devices. [102,103,[110][111][112][113][114][115][116][117] But, the preparation of photoactive materials only is not enough to achieve such a remarkable progress. [102,103,[110][111][112][113][114][115][116][117] But, the preparation of photoactive materials only is not enough to achieve such a remarkable progress.…”

Section: Zwitterion Materials For Organic Solar Cellsmentioning

confidence: 99%

Zwitterions for Organic/Perovskite Solar Cells, Light‐Emitting Devices, and Lithium Ion Batteries: Recent Progress and Perspectives

Islam

Pervaiz

et al. 2019

Advanced Energy Materials

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are covalently bonded and their unique characteristics enable them to demonstrate special performance in applications and distinguish them from other conventional organic salts. [12][13][14] Recently, a significant attention has been paid to the use of zwitterions owing to their solubility in polar solvents for solution processing, [15][16][17] and dipole formation for the transfer of carriers [18][19][20] and ions. [21][22][23] Zwitterions have emerged as alternatives to the widely used building blocks such as conventional ionic groups, for developing new functional materials. The presence of both negative and positive ions in the same molecule enables zwitterions to develop interfacial dipole. The ability of zwitterions to develop interfacial dipole provides a new pathway to utilize them as interfacial layer in optoelectronic devices, including organic solar cells (OSCs), perovskite solar cells (PVSCs), and organic light-emitting devices (OLEDs), as well as electrolyte additives for energy devices such as lithium ion batteries (LIBs).It is well known that the ability to transport the charge carriers between the electrodes and organic layers is very crucial to obtain highly efficient electronic devices. [24] A mismatch between the energy levels of organic layers and inorganic electrodes leads to the generation of an energy barrier that hampers the extraction or injection of charge carriers. [25] To get rid of this obstacle, an interlayer between the electrodes and organic layers is applied to facilitate the transfer of charges in organic devices. In OLEDs, interlayers are used to enhance charge injection and reduce the height of Schottky barrier. While in the case of OSCs and PVSCs, apart from the enhancement in charge injection, they also play an important role to increase the built-in electric field across the active layer, ensuring efficient extraction of photogenerated charge carriers. [26][27][28][29][30] Therefore, the design and development of effective interlayer materials for interfacial modification are crucial for high-performance electronic devices. Recently, some significant advances have been demonstrated by applying an interfacial layer between the electrodes and organic layers, resulting in power conversion efficiencies (PCEs) to exceed 14% for single-junction OSCs by choosing appropriate photoactive layer. [31,32] Among different interlayer materials used so far, zwitterionic materials have been proved Zwitterions, a class of materials that contain covalently bonded cations and anions, have been extensively studied in the past decades owing to their special features, such as excellent solubility in polar solvents, for solution processing and dipole formation for the transfer of carriers and ions. Recently, zwitterions have been developed as electrode modifiers for organic solar cells (OSCs), perovskite solar cells (PVSCs), and organic light-emitting devices (OLEDs), as well as electrolyte additives for lithium ion batteries (LIBs).With the rapid advances of zwitterionic materials, high-performan...

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A Thieno[3,4-b]thiophene-Based Non-fullerene Electron Acceptor for High-Performance Bulk-Heterojunction Organic Solar Cells

Cited by 287 publications

References 47 publications

Dithieno[3,2‐b:2′,3′‐d]pyrrol Fused Nonfullerene Acceptors Enabling Over 13% Efficiency for Organic Solar Cells

Dithieno[3,2‐b:2′,3′‐d]pyrrol Fused Nonfullerene Acceptors Enabling Over 13% Efficiency for Organic Solar Cells

High‐Efficiency Polymer:Nonfullerene Solar Cells with Quaterthiophene‐Containing Polyimide Interlayers

Zwitterions for Organic/Perovskite Solar Cells, Light‐Emitting Devices, and Lithium Ion Batteries: Recent Progress and Perspectives

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