Modular design of SPIRO-OMeTAD analogues as hole transport materials in solar cells

Murray, Angela K.; Frost, Jarvist M.; Hendon, Christopher H.; Molloy, Christopher D.; Carbery, David R.; Walsh, Aron

doi:10.1039/c5cc02129d

Cited by 64 publications

(47 citation statements)

References 31 publications

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“…9 Also, the lack of crystalline spiro-OMeTAD, in particular single crystals prepared in a controlled manner, prevents access to the intrinsic holetransport properties of spiro-OMeTAD, the understanding of which is important for improving performance [10][11][12] and/or developing alternative organic HTMs. [13][14][15] Very recently, significant experimental progress was made in preparing crystalline spiro-OMeTAD. Ganesan et al reported the first crystal structure of a spiro-OMeTAD complex in which, however, chlorobenzene solvent molecules are also embedded.…”

Section: Introductionmentioning

confidence: 99%

Characterization of intrinsic hole transport in single-crystal spiro-OMeTAD

Zhong

et al. 2017

npj Flex Electron

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Spiro-OMeTAD remains a prominent hole-transport material in perovskite and solid-state dye-sensitized solar cells. However, an understanding of its intrinsic hole-transport properties is still limited. Here, hole transport in spiro-OMeTAD is systematically characterized on the basis of the recently reported X-ray single-crystal data. An approach combining density functional theory calculations, tight-binding modeling, and kinetic Monte Carlo simulations are exploited to describe the key parameters governing hole transport and to investigate the transport mechanism and hole mobilities in the spiro-OMeTAD single crystal. The results provide insight into: (i) why an anisotropic hole-transport mechanism, with an upper range of intrinsic hole mobilities on the order of~10 −3 cm 2 /Vs, can be expected in the single crystal; and (ii) how detrimental factors, related to the presence of the spiro motif and of the 4,4′-dimethoxydiphenylamine substituents, limit the intrinsic hole mobilities of the system.

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Section: Introductionmentioning

confidence: 99%

Characterization of intrinsic hole transport in single-crystal spiro-OMeTAD

Zhong

et al. 2017

npj Flex Electron

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“…It is an excellent hole transport material since it meets the requirements for an ideal HSL material. However, the use of spiro‐OMeTAD may seriously hinder the commercialization of the PVSC technology because of the following shortfalls: 1) it has a high synthesis and purification cost; 2) it must be sufficiently thick, typically about 200 nm, in order to achieve high PCEs, which is much thicker than other HSLs and thus more material usage; and 3) it requires oxygen doping, which is incompatible with device encapsulation . Therefore, it is urgently necessary to design and demonstrate new spiro‐OMeTAD derivatives or alternatives that can overcome these shortfalls, while maintaining high PCEs, to further reduce the material cost barriers to PVSC commercialization.…”

Section: Introductionmentioning

confidence: 99%

A New Hole Transport Material for Efficient Perovskite Solar Cells With Reduced Device Cost

et al. 2017

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To realize commercialization of perovskie solar cell (PVSC) technology, it is essential to reduce the device costs while maintaining high power conversion efficiencies (PCEs). So far, the high cost of the most commonly used hole selective material, 2,2′,7,7′‐Tetrakis (N,N‐di‐p‐methoxyphenylamino)‐9,9′‐spirobifluorene (spiro‐OMeTAD), for high‐PCE PVSCs presents a significant obstacle for device cost reduction. In this work, the synthesis and characterization of a new spiro‐OMeTAD derivative hole selective material, 2,6,14‐tris(5′‐(N,N‐bis(4‐methoxyphenyl)aminophenol‐4‐yl)‐3,4‐ethylenedioxythiophen‐2‐yl)‐triptycene (TET) is reported. TET features a three‐dimensional structure consisting of a triptycene core and triarylamine arms linked by 3,4‐ethylenedioxythiophene, facilitating efficient hole transport. Planar PVSCs using TET hole selective layers (HSLs) achieved high fill factors of over 81% and steady‐state efficiencies of up to 18.6%, comparable with that (19.0%) of PVSC using spiro‐OMeTAD HSL. Importantly, the hereby reported efficient PVSCs can be produced with very thin TET HSLs (about 30 nm). Considering the lower laboratory synthesis and purification cost ($123 vs. $500 g−1) and thinner HSL (30 vs. 200 nm), the cost for TET on a unit area of one device is 25 times lower than that for high‐purity spiro‐OMeTAD. The device with TET HSL shows good stability under continuous illumination. Therefore, this work makes a significant step forward toward the commercialization of the emerging PVSC technology.

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“…Charge‐transporting materials featuring suitable energy levels and good electronic properties are also important to achieve high performance in PSCs . The dominant HTM 2,2′,7,7′‐tetrakis( N , N ‐di‐ p ‐methoxyphenylamine)9,9′‐spirobifluorene (spiro‐OMeTAD) has a complicated synthesis and requires costly purification steps, limiting its large‐scale industrial application . Hence, many other alternatives have been developed .…”

Section: Introductionmentioning

confidence: 99%

“…[7][8][9][10] The dominant HTM 2,2',7,7'-tetrakis(N,N-di-p-methoxyphenylamine)9,9'-spirobifluorene (spiro-OMeTAD) has ac omplicated synthesis and requires costly purifications teps, limiting its large-scale industriala pplication. [11] Hence, many other alternatives have been developed. [12][13][14][15][16] The packing mode and molecular ordering of organic semiconductor thin films are vital to the charge-transporting properties.…”

Section: Introductionmentioning

confidence: 99%

N‐Annulated Perylene‐Based Hole Transporters for Perovskite Solar Cells: The Significant Influence of Lateral Substituents

Zhu

Wang

et al. 2018

ChemSusChem

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Perylene derivatives are a family of well-known organic electron-transporting materials with excellent photochemical and thermal stabilities, and have been widely used in various optoelectronic devices. In this work, two diphenylamine functionalized N-annulated perylenes are reported as hole-transporting materials (HTMs) for perovskite solar cells. Through joint theoretical and experimental studies, the HTM employing a methoxyphenyl lateral substituent is found to feature a closer stacking distance and better aggregate connectivity in the solid film than its analogue with the bulky 2-hexyldecyl lateral substituent, contributing to a higher hole mobility and a remarkably enhanced device performance of perovskite solar cells. This work demonstrates the significant influence of lateral substituents of HTMs on the intermolecular packing and solid microstructure, giving a clear insight on the molecular design of high-performance organic semiconductors.

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Modular design of SPIRO-OMeTAD analogues as hole transport materials in solar cells

Cited by 64 publications

References 31 publications

Characterization of intrinsic hole transport in single-crystal spiro-OMeTAD

Characterization of intrinsic hole transport in single-crystal spiro-OMeTAD

A New Hole Transport Material for Efficient Perovskite Solar Cells With Reduced Device Cost

N‐Annulated Perylene‐Based Hole Transporters for Perovskite Solar Cells: The Significant Influence of Lateral Substituents

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