Design rules for the preparation of low-cost hole transporting materials for perovskite solar cells with moisture barrier properties

Petrus, Michiel L.; Music, Arif; Closs, Anna C.; Bijleveld, Johan; Sirtl, Maximilian T.; Hu, Yinghong; Dingemans, Theo J.; Bein, Thomas; Docampo, Pablo

doi:10.1039/c7ta06452g

Cited by 57 publications

(52 citation statements)

References 74 publications

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“…The superior stability of devices comprising EDOT‐Amide‐TPA is expected to originate from the high quality HTM layer that functions as a moisture barrier. This moisture barrier property was recently described for azomethine‐based small molecules . We additionally show that employing EDOT‐Amide‐TPA as the HTM leads to improved stability compared to devices comprising Spiro‐OMeTAD (Figure S26e, Supporting Information) under the presence of humidity, heat and air.…”

Section: Device Characterizationsupporting

confidence: 80%

“…More importantly, no expensive metal catalysts are required when using this chemistry, the synthesis can be done at ambient conditions and since water is the only side‐product, product purification is very straightforward . Azomethine‐, enamine‐, and hydrazone‐based organic molecules have been reported as HTMs, although none of these materials have been able to outperform state‐of‐the‐art materials …”

Section: Introductionmentioning

confidence: 99%

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New Generation Hole Transporting Materials for Perovskite Solar Cells: Amide‐Based Small‐Molecules with Nonconjugated Backbones

Petrus

Schutt

Sirtl

et al. 2018

Advanced Energy Materials

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with outstanding optoelectronic properties. [1] In 2009, these materials were introduced in solar cells and have since established a striking increase in performance, reaching over 22% in stateof-the-art devices. [2] Here, the perovskite absorber is sandwiched between two selective charge extraction layers, that transport the charges to the electrodes. [3] Although efficient inorganic hole transporting materials (HTMs) have been reported, [4] the most well-known HTMs are the organic materials 2,2′,7,7′-tetrakis-(N,N-di-4-methoxyphenylamino)-9,9′spirobifluorene (Spiro-OMeTAD) and polytriarylamine (PTAA). Alternatives that compete in performance have been published, [5][6][7] however, just like Spiro-OMeTAD and PTAA, most of these materials are synthesized in multistep synthetic procedures, involving (transition) metal catalyzed cross-coupling reactions, stringent reaction conditions and extensive product purification. This results in a relative high material cost, consequently leading to a significant contribution to the total device cost. [5,8,9] Additionally, the tedious synthesis hampers large State-of-the-art perovskite-based solar cells employ expensive, organic hole transporting materials (HTMs) such as Spiro-OMeTAD that, in turn, limits the commercialization of this promising technology. Herein an HTM (EDOT-Amide-TPA) is reported in which a functional amide-based backbone is introduced, which allows this material to be synthesized in a simple condensation reaction with an estimated cost of <$5 g −1 . When employed in perovskite solar cells, EDOT-Amide-TPA demonstrates stabilized power conversion efficiencies up to 20.0% and reproducibly outperforms Spiro-OMeTAD in direct comparisons. Time resolved microwave conductivity measurements indicate that the observed improvement originates from a faster hole injection rate from the perovskite to EDOT-Amide-TPA. Additionally, the devices exhibit an improved lifetime, which is assigned to the coordination of the amide bond to the Li-additive, offering a novel strategy to hamper the migration of additives. It is shown that, despite the lack of a conjugated backbone, the amide-based HTM can outperform state-of-the-art HTMs at a fraction of the cost, thereby providing a novel set of design strategies to develop new, low-cost HTMs.

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Section: Device Characterizationsupporting

confidence: 80%

Section: Introductionmentioning

confidence: 99%

New Generation Hole Transporting Materials for Perovskite Solar Cells: Amide‐Based Small‐Molecules with Nonconjugated Backbones

Petrus

Schutt

Sirtl

et al. 2018

Advanced Energy Materials

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“…Its shallow HOMO level, compared with the perovskite (À5.4 eV), provides driving force to extract holes from the perovskite layer;t he high LUMO level effectively blocks electrons from the perovskite layer to the HTM. [34] The perovskite layer is well distin-guisheda nd its thickness is about 550 nm. The chemical structure of m-MTDATA is shown in Figure 1d.…”

Section: Introductionmentioning

confidence: 99%

Efficient and Stable Inverted Planar Perovskite Solar Cells Using a Triphenylamine Hole‐Transporting Material

Chen

et al. 2018

ChemSusChem

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Inverted perovskite solar cells (PSCs) with a p-i-n structure have attracted great attention. Normally, inorganic p-type metal oxides or polymers are used as the hole-transport material (HTM), a vital component in the inverted PSCs. However, this type of HTM often requires high processing temperatures and/or high costs. On the other hand, a commonly used organic HTM, poly(3,4-ethylenedioxythiophene polystyrene sulfonate (PEDOT:PSS), is sensitive to humidity and thus affects the stability of the PSCs. Herein, we employ a small molecule, 4,4',4''-tris(N-3-methylphenyl-N-phenylamino) triphenylamine (m-MTDATA) to replace PEDOT:PSS as a new HTM for inverted PSCs. Compared to a PEDOT:PSS-based device, m-MTDATA-based PSCs exhibit enhanced performance. The highest power conversion efficiency (PCE) was notably improved from 13.44 % (PEDOT:PSS) to 18.12 % (m-MTDATA), suggesting that m-MTDATA could be an efficient HTM to achieve high performance inverted PSCs. Furthermore, the m-MTDATA-based device demonstrated improved stability (retaining 90 % PCE) under ambient conditions over 1000 h compared with the PEDOT:PSS-based devices (retaining 40 % PCE).

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“…[5][6][7] Moreover, the HTM helps to reduce the degradation of the device by protecting the sensitive perovskite from the diffusion of the metal electrode into the perovskite layer as well as from air and moisture. 6,8,9 The structure and properties of the HTM are crucial to achieve efficient and stable solar cells. 10,11 Hence, a wide number of alternative HTMs structures has been investigated in PSCs including inorganic materials, [12][13][14] small organic molecules [15][16][17] and polymers.…”

Section: Introductionmentioning

confidence: 99%

Star-shaped triarylamine-based hole-transport materials in perovskite solar cells

Pineda

Zems

Troughton

et al. 2020

Sustainable Energy Fuels

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Design rules for the preparation of low-cost hole transporting materials for perovskite solar cells with moisture barrier properties

Abstract: A series of azomethine-based HTMs is synthesized using simple condensation chemistry. Their photovoltaic performance and moisture barrier properties are presented.

Cited by 57 publications

References 74 publications

New Generation Hole Transporting Materials for Perovskite Solar Cells: Amide‐Based Small‐Molecules with Nonconjugated Backbones

New Generation Hole Transporting Materials for Perovskite Solar Cells: Amide‐Based Small‐Molecules with Nonconjugated Backbones

Efficient and Stable Inverted Planar Perovskite Solar Cells Using a Triphenylamine Hole‐Transporting Material

Star-shaped triarylamine-based hole-transport materials in perovskite solar cells

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