Bay-linked perylene bisimides as promising non-fullerene acceptors for organic solar cells

Ji, Wei; Ye, Long; Li, Xiangguang; Xiao, Chengyi; Tan, Fang; Zhao, Wenchao; Hou, Jianhui; Wang, Zhaohui

doi:10.1039/c3cc47204c

Cited by 293 publications

(261 citation statements)

References 34 publications

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“…The geometric constraints of stacking essentially limit their coupling to two neighbors, with the result that none of the N C values for PDI derivatives rise much above ∼2 for any appreciable value of the coupling threshold. This also correlates with the counterintuitive result that the best fullerene replacements in organic solar cells have been PDI units designed to disrupt stacking via covalent dimerization (41)(42)(43). In addition to promoting miscibility with the donor, these nonplanar structures likely emulate the superior percolative properties of spherical fullerenes.…”

Section: Network Robustnessmentioning

confidence: 87%

Mesoscale molecular network formation in amorphous organic materials

Savoie

Kohlstedt

Jackson

et al. 2014

Proc. Natl. Acad. Sci. U.S.A.

104

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High-performance solution-processed organic semiconductors maintain macroscopic functionality even in the presence of microscopic disorder. Here we show that the functional robustness of certain organic materials arises from the ability of molecules to create connected mesoscopic electrical networks, even in the absence of periodic order. The hierarchical network structures of two families of important organic photovoltaic acceptors, functionalized fullerenes and perylene diimides, are analyzed using a newly developed graph methodology. The results establish a connection between network robustness and molecular topology, and also demonstrate that solubilizing moieties play a large role in disrupting the molecular networks responsible for charge transport. A clear link is established between the success of mono and bis functionalized fullerene acceptors in organic photovoltaics and their ability to construct mesoscopically connected electrical networks over length scales of 10 nm.soft materials | disordered properties | charge generation T he discovery that organic semiconductors can complement, or even replace, more expensive/less processable inorganic semiconductors in many applications has spurred intense research for several decades (1). This led to the realization of devices where organics act as one, or all, of the components in transistor, battery, light-emitting diode, photovoltaic, and artificial photosynthetic technologies (2). All of these applications rely on the efficient mesoscopic (10-1,000 nm length scale) transport of charge or energy through space, whereas the fundamental design unit for these systems is the single molecule (∼1 nm length scale). The successful function of these devices thus lies in the ability to bridge these length scales through the construction of efficient electrical molecular networks in the condensed phase. In this context, the challenge for materials scientists is to develop molecular descriptors that are predictive for macroscopic observables, such as charge mobility (3), exciton diffusion (4), or charge generation (5).To close this understanding gap, it will be necessary to develop methodologies that go beyond the traditional formulation of quantum chemistry, which begins with accurate single-molecule properties and extrapolates outward, to frameworks that establish the hierarchical importance of the many possible intermolecular interactions in structurally disordered materials (6-9). In this work, we show how network theory can be combined with quantum chemistry to describe the mesoscopic percolative behavior of technologically relevant organic electron acceptors. The network framework enables the connectivity of the quantum transport states in these materials to be described on the 10-1,000 nm length scale as a function of molecular identity and structural disorder. By evaluating how the transport networks transform with structural disorder and molecular identity, we elucidate the connection between network robustness and molecular topology.Nature offers a template fo...

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Section: Network Robustnessmentioning

confidence: 87%

Mesoscale molecular network formation in amorphous organic materials

Savoie

Kohlstedt

Jackson

et al. 2014

Proc. Natl. Acad. Sci. U.S.A.

104

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“…As a result, the V oc of such IC 60 BA-based device reached 0.84 V compared to 0.58 V of PC 60 BM-based device, and the PCE increased from 3.88 to 6.48 % [16]. Later on, a better optimized device of P3HT/ IC 60 BA reported in 2012 reached a PCE of 7.5 % by applying a special electrontransporting layer [17].…”

Section: Fullerene-based Materialsmentioning

confidence: 67%

“…It is also noteworthy that IC 60 BA shows a slightly stronger absorption in the visible range compared to PC 60 BM but much weaker than C 70 derivatives. In order to combine both the advantages of higher LUMO level and stronger visible light absorption, IC 70 BA was synthesized and tested for solar cell applications [21] Indeed, in a P3HT/IC 70 BA BHJ solar cell, the PCE saw a slight increase to 5.64 % compared to 3.55 % of PC 60 BA under similar device architecture ( , and the singlet annihilation rate constant reached 0.5 × 10 −9 cm 3 s −1…”

Section: Fullerene-based Materialsmentioning

confidence: 94%

“…Three years later, the first BHJ polymer solar cell was reported [1]. It utilized a fullerene derivative PC 60 BM as the acceptor/electron transporting material to generate separated charges and to transport the electrons, affording a PCE of 2.9 %. After almost two decades of development and improvement, interestingly, fullerene derivatives still predominate as the active acceptor materials in contemporary benchmark organic solar cells, including those demonstrated PCE higher than 9 %.…”

Section: Fullerene-based Materialsmentioning

confidence: 99%

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n-Type Electron-Accepting Materials for Organic Solar Cells (OSC)

Zhou

Lee

Fang

2014

Organic and Hybrid Solar Cells

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“…10−13 Some high-performance NFAs have been recently developed for OPV applications, and the BHJ organic solar cells fabricated with these molecules show high PCEs exceeding 11%. 14 The most common structural template involves small molecules containing electron-deficient units, viz., perylene diamides, 2,15−20 diketopyrrolopyrrole, 7,21,22 benzothiadiazole, rhodanine, 23−26 and dicyanovinyl. 27−29 Although a significant advancement in this field occurred only in the last few years, the first ever bilayer OSC invented by Tang in 1986 was made from an NFA, named 3,4,9,10-perylenetetracarboxylic bisbenzimidazole (PTCBI), and small-molecule donor copper phthalocyanine (CuPc) yielding a PCE of 1%.…”

Section: Introductionmentioning

confidence: 99%

High-Performance Non-Fullerene Acceptor Derived from Diathiafulvalene Wings for Solution-Processed Organic Photovoltaics

et al. 2016

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A solution-processable small-molecule nonfullerene electron acceptor BAF-2HDT (7,7′-(9,9-didecyl-9H-fluorene-2,7-diyl)bis(4-((4,5-bis(hexylthio)-1,3-dithiol-2 ylidene)methyl)benzo[c][1,2,5]-thiadiazole) bearing hexadiathiafulvalene (HDT) wings as end groups has been synthesized for bulk heterojunction organic photovoltaics. The molecule shows broad absorption in the 300−600 nm range with a molar extinction coefficient (ε) of 9.32 × 10 4 M −1 ·cm −1 exceeding to that of [6,6]-phenyl-C 71 -butyric acid methyl ester of 2.8 × 10 4 M −1 ·cm −1 at 461 nm. The HOMO and LUMO energy levels of the molecule are found to be −5.69 and −3.58 eV, respectively which is compatible with low band gap high-performance polymers such as poly[(5,6-difluoro-2,1,3-benzothiadiazol-4,7-diyl)-alt-(3,3‴-di(2-octyldodecyl)-2,2′;5′,2″;5″,2‴-quaterthiophen-5,5‴-diyl)] (PffBT4T-2OD). Photoluminescence-quenching measurements confirm that the molecule BAF-2HDT has excellent electron-accepting capability. The organic solar cells made from BAF-2HDT blending with conjugated polymer donor PffBT4T-2OD exhibit a power conversion efficiency of 7.13% with high V oc of 0.77 V, J sc of 14.64 mA·cm −2 , and FF of 0.64. The design and development of such nonfullerene acceptors with high ε may be key to further development of high-performance and costeffective solution-processed organic solar cells.

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Bay-linked perylene bisimides as promising non-fullerene acceptors for organic solar cells

Cited by 293 publications

References 34 publications

Mesoscale molecular network formation in amorphous organic materials

Mesoscale molecular network formation in amorphous organic materials

n-Type Electron-Accepting Materials for Organic Solar Cells (OSC)

High-Performance Non-Fullerene Acceptor Derived from Diathiafulvalene Wings for Solution-Processed Organic Photovoltaics

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