Synthesis of 3<i>H</i>‐Benzo[e]indoline and Its Application to Small‐Molecule Organic Solar Cells

Chen, Yao; Wu, Jianglin; Yang, Lin; Hu, Bin; Yang, Daobin; Lu, Zhiyun; Huang, Yan

doi:10.1002/chem.201800938

Cited by 17 publications

(2 citation statements)

References 36 publications

(35 reference statements)

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“…Earlier, theoretical simulations were used to understand the structure‐property relationships in OSCs to a certain extent, [ 32 ] and a few simple, highly crystalline molecules or molecular fragments were explored by single crystal analysis. [ 33–36 ] However, there is an urgent need to reveal the packing arrangements and intermolecular interactions of FREAs for OSCs, especially in high‐performance A‐DAD‐A‐type [ 20 ] and A‐D‐A‐type acceptors, [ 9 ] because this would help us understand the electronic processes in active layers and design new generation materials for the development of OSC devices. [ 37 ] In this review, we have summarized the chemical structures of FREAs including PDI‐type acceptors, [ 36,38 ] A‐D‐A‐type [ 37,39–53 ] and A‐DAD‐A‐type acceptors.…”

Section: Introductionmentioning

confidence: 99%

Crystal Engineering in Organic Photovoltaic Acceptors: A 3D Network Approach

Lai

2020

Advanced Energy Materials

102

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The power conversion efficiency of organic solar cell (OSC) devices has surpassed 18% rapidly. In order to further promote OSC development, it is necessary to understand the packing information at the atomic level to help develop acceptor systems with superior performance. The packing arrangements and intermolecular interactions of these acceptors in the solid state, observed by single crystal X‐ray crystallography, are often used to design materials with expected physicochemical properties. In this review, the chemical structures of acceptors revealed by single crystal X‐ray crystallography are summarized, and the relationship between structural design, packing arrangement, and device properties is discussed. In addition, the concept of “3D network packing” in acceptor systems is proposed, which offers better charge transfer properties in reported chlorinated, fluorinated, brominated, and trifluoromethylated systems, an understanding of 3D network transport also provides guidance in high‐performance materials design. Finally, some current issues related to single crystal studies in OSCs are discussed, with an emphasis on the significance of developing acceptors by understanding and adjusting the aggregation states and intermolecular interactions of materials by single crystal analysis.

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Section: Introductionmentioning

confidence: 99%

Crystal Engineering in Organic Photovoltaic Acceptors: A 3D Network Approach

Lai

2020

Advanced Energy Materials

102

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“…Owing to their intense optical absorption in the visible–NIR region, good photochemical stability, and, most importantly, facile synthetic access, squaraine dyes (SQ) have drawn much attention for OSCs applications (Figure ). ,− To the best of our knowledge, most of the squaraine families are synthesized without tedious synthetic routes and/or highly toxic reagents. ,− For example, in 2008, we first introduced a simple route to squaraine dyes having broad optical absorption in the 550–850 nm range and incorporated them, with PC 61 BM as the electron acceptor, in OSC devices . This was the first introduction of squaraine dyes as a donor for solution processed OSCs and achieved a PCE of 1.24%.…”

Section: Introductionmentioning

confidence: 99%

Performance, Morphology, and Charge Recombination Correlations in Ternary Squaraine Solar Cells

Chen

Yang

et al. 2018

Chem. Mater.

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Ternary bulk-heterojunction organic solar cells (BHJ-OSCs) are demonstrated by combining two squaraine donors (USQ3OH and IDPSQ) having complementary optical absorption and PC71BM as the acceptor. While the corresponding binary cells exhibit maximum power conversion efficiencies (PCEs) of 4.65% (IDPSQ binary) and 6.85% (USQ3OH binary), the ternary cells of weight composition IDPSQ:USQ3OH:PC71BM = 0.15:1.0:3.0 (15%TB, TB = ternary blend) exhibit a PCE of 7.20%, which is the highest known value to date for a squaraine OSC. Single crystals of both squaraines and space-charge-limited current (SCLC) measurements explain the efficiency difference between the binary cells. SCLC measurements and transmission electron microscopy imaging of the ternary devices indicate that the charge mobility slightly increases and the BHJ domain size optimizes for the 15%TB device vs that based on the USQ3OH blend. Grazing incidence wide-angle X-ray scattering data reveal that enhanced π–π stacking and larger correlation lengths can be achieved after thermal annealing of the ternary blend film. Charge recombination measurements demonstrate that IDPSQ can be incorporated into the blend without increasing charge recombination. Finally, flexible OSCs on PET (polyethylene terephthalate) with a PCE of ∼4.5% were fabricated. This study demonstrates that readily accessible squaraine cores represent a viable choice for the design of new organic solar cell donor materials.

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