SFX as a low-cost ‘Spiro’ hole-transport material for efficient perovskite solar cells

Maciejczyk, Michał; Ivaturi, Aruna; Robertson, Neil

doi:10.1039/c6ta00110f

Cited by 113 publications

(99 citation statements)

References 35 publications

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“…[50,51,62,63] The UV/Vis absorption spectra of all HTMs as methylene chloride solutions are presented in Figure 2a,a nd the optical parameters of the HTMs are listed in Ta ble1.T he Yih-series HTMs exhibited two main absorption peaks within 300-382 nm. Ad etailed cost calculation is presented in Scheme S1 andT able S2.…”

Section: Resultsmentioning

confidence: 99%

“…[1] PSCs have since achieved rapid increase in PCE from 3.8 %t oo ver 20 %, [2][3][4][5][6] owing to the perovskite active layer,w hich exhibits severalb enefits like broad absorptivity, long electron-hole diffusion length, [7] efficient charge-transport capability, [8][9][10] and low charge-recombination rate. [44,45] Considerable efforts have also been devoted to investigating suitable HTMs by replacing the spiro-based core with novel spiro-based HTMs like spiro-acridine-fluorene, [46,47] spiro-bi[thieno [3,4-b] [1,4]dioxepine], [48] dispiro-oxepine, [49] spiro[fluorene-9,9'-xanthene], [6,[50][51][52][53] and spiro-phenylpyrazole-fluorine. [2,3,5] As Spiro-OMeTAD exhibits al ow recombination rate and efficient hole-transport mobility,t he overall devicep erformance is improved when the materiali si ncluded.…”

Section: Introductionmentioning

confidence: 99%

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Facilely Synthesized spiro[fluorene‐9,9′‐phenanthren‐10′‐one] in Donor–Acceptor–Donor Hole‐Transporting Materials for Perovskite Solar Cells

Chen

Huang

et al. 2018

ChemSusChem

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We have demonstrated two novel donor-acceptor-donor (D-A-D) hole-transport material (HTM) with spiro[fluorene-9,9'-phenanthren-10'-one] as the core structure, which can be synthesized through a low-cost process in high yield. Compared to the incorporation of the conventional HTM of commonly used 2,2',7,7'-tetrakis[N,N-di(4-methoxyphenyl)amino]-9,9'-spirobifluorene (Spiro-OMeTAD), the synthesis process is greatly simplified for the presented D-A-D materials, including a minimum number of purification processes. This results in an increased production yield (>55 %) and suppressed production cost (<30 $ g ), in addition to high power conversion efficiency (PCE) in perovskite solar cells (PSCs). The PCE of a PSC using our D-A-D HTM reaches 16.06 %, similar to that of Spiro-OMeTAD (16.08 %), which is attributed to comparable hole mobility and charge-transfer efficiency. D-A-D HTMs also provide better moisture resistivity to prolong the lifetime of PSCs under ambient conditions relative to their Spiro-OMeTAD counterparts. The proposed new type of D-A-D HTM has shown promising performance as an alternative HTM for PSCs and can be synthesized with high production throughput.

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Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Facilely Synthesized spiro[fluorene‐9,9′‐phenanthren‐10′‐one] in Donor–Acceptor–Donor Hole‐Transporting Materials for Perovskite Solar Cells

Chen

Huang

et al. 2018

ChemSusChem

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“…As can be seen in Figure S2 (Supporting Information), their electron density distribution of HOMOs are all located at the heteroaromatic sections bearing xanthene, thioxanthene, acridine, and even the functional diphenylamine substituents, whereas the LUMOs (lowest unoccupied molecular orbitals) are mainly located at phenylpyrazole. [43]. [45,46] In addition, the variation of the calculated HOMO levels is in good agreement with the experimental results as follows: PPyra-ACD Measured in THF with a concentration of 10 −5 m; b) Energy gap calculated from the absorption onset; c) The oxidative onset potential (vs FcH/FcH + ) measured by cyclic voltammetry in CH 2 Cl 2 ; d) HOMO = −(E ox + 5.1) eV; e) LUMO = HOMO + E g,opt ; f) Reported in ref.…”

Section: Resultsmentioning

confidence: 99%

Spiro‐Phenylpyrazole‐9,9′‐Thioxanthene Analogues as Hole‐Transporting Materials for Efficient Planar Perovskite Solar Cells

Wang

Zhu

Chueh

et al. 2017

Advanced Energy Materials

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energy. Since the first report by Miyasaka and co-workers in 2009, [1] the perovskites (e.g., CH 3 NH 3 PbI 3 ) have been widely studied due to their good light absorption capability from visible to near-infrared, long charge diffusion lengths, and high carrier mobilities as well as solutionprocessabilities. [2][3][4][5][6][7][8][9][10] Benefited from careful modification of perovskite, delicate design of device configuration, and in-depth understanding of interfacial interactions, the power conversion efficiencies (PCEs) of PVSCs have been skyrocketed from initial 3.8% to above 20% to date. [11][12][13][14][15][16][17][18][19] Nowadays, as a necessary component in the most studied conventional n-i-p junction PVSCs, the hole-transporting materials (HTMs) play an even more critical role in efficiently extracting holes separated from perovskite layer and simultaneously transmitting to anode in order to avoid loss in open-circuit voltage (V oc ) and decrease in charge recombination. [20][21][22][23] Currently, most of the highly efficient PVSCs utilize 2,2′,7,7′-tetrakis(N,N-di-p-methoxyphenylamine)-9,9′-spirobifluorene (Spiro-OMeTAD) as the HTM owing to its matched energy level with the valence band edge of the perovskite, and high compatibility with lithium bis(trifluoromethanesulfonyl)imide (LiTFSI) dopant. Nevertheless, the low synthetic yield and high cost for Spiro-OMeTAD will inevitably obviate the large-scale production and practical commercialization of PVSCs. As a result, efforts have been executed in developing cheaper, more stable, and efficient organic HTMs to replace Spiro-OMeTAD. When focusing on their intrinsic properties, these small molecular HTMs can be divided into three categories: (i) donor-acceptor type structures to form intramolecular charge transfer character, which usually show decent PCEs in dopant-free devices; [24][25][26][27] (ii) 2D (quasi) planar molecular structures to enhance intermolecular π-π interactions, which lead to excellent hole-transporting properties; [28,29] (iii) arylamines derivatives with different central building blocks such as pyrene, [30] 1,1,2,2-tetraphenylethene, [31] bifluorenylidene, [32] 4,4-N,N′-dicarbazole-1,1′-biphenyl, [33] quinolizino acridine, [34] thiophene, and derivatives, etc., [35][36][37][38] and di(4-methoxyphenyl)amine as the peripheral functional groups to endow adequate hole-transporting properties via radical cation species. [39] It is worth noting that the efficient HTMs in the state-of-the-art PVSCs usually contain spiro-arranged Perovskite solar cells have emerged as a promising technique for low-cost, light weight, and highly efficient photovoltaics. However, they still largely rely on 2,2′,7,7′-tetrakis(N,N-di-p-methoxyphenylamine)-9,9′-spirobifluorene (Spiro-OMeTAD) to serve as hole-transporting materials (HTMs). Here, a series of HTMs with small molecular weight is designed, which are constructed on a spiro core involving phenylpyrazole and a second heteroaromatics, i.e., xanthene (O atom), thioxanthene (S atom), and acridine (N atom)....

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“…Especially, the synthesis of the Spiro core in 2,2′,7,7′-tetrakis(N,N-di-p-methoxyphenylamine)-9,9′-spirobifluorene (Spiro-OMeTAD) requires several steps with a poor overall yield (15 to 30% depending on the synthesis route) [203] and is therefore often replaced by synthetically more accessible cores. Simple moieties such as phenyl, [206] biphenyl, [207] carbazole, [207,208] triphenylamine, [209] or triptycene [210] can be used to reduce the cost, and spiro-based alternatives such as spiro[fluorene-9,9′-xanthene], [211,212] spiro[cyclopenta [2,1- [213] Li et al introduced heteroatoms in the core by using the simple 3,4-ethylenedioxythiophene (EDOT) moiety. Additionally, they were able to perform their reaction in one pot to further reduce the cost.…”

Section: Long-term Viability: Stability and Sustainabilitymentioning

confidence: 99%

Capturing the Sun: A Review of the Challenges and Perspectives of Perovskite Solar Cells

Petrus

Schlipf

Cheng

et al. 2017

Advanced Energy Materials

312

201

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following statement: These materials can be processed from solution and yet exhibit optoelectronic materials properties described in classic solid-state physics textbooks. This unprecedented combination has led to photovoltaic devices that can be processed at room temperature and achieve performance levels similar to industry giant polycrystalline silicon, from a starting point of 3.8% in 2009. [1][2][3][4] The first light-emitting electrochemical cells [5] and diodes [6][7][8] have also been introduced recently, leading to tunable light emission spectra and internal quantum efficiencies exceeding 15%.The road towards these achievements has been marked by a constant improvement of perovskite deposition techniques fueled by our increasing understanding of the crystallization processes. The choice of deposition technique, either from solution or vapor, and the composition and order in which precursor species are applied has a great influence on the crystallization kinetics. Here, one can distinguish one-step methods where the perovskite is formed from a precursor mixture dissolved in a common solution, and two-step methods where the inorganic compound is deposited first and transformed to the perovskite phase later by addition of the organic constituents. [9][10][11] Furthermore, many parameters during processing can have an effect on the crystallization mechanism and consequently on film morphology, such as the choice of solvents, concentrations and processing additives that are often not incorporated into the final product. [11][12][13] We discuss this aspect in Section 2, where we focus our attention on the most commonly employed solution-based techniques. Additionally, as for any new technology trying to displace an incumbent technology, higher efficiencies, lower costs, reproducibility, stability, and sustainability are paramount. In particular, reproducibility has been a major challenge in perovskite solar cells from the beginning: small variations in morphology, like crystal size, film roughness, and pinholes can have detrimental effects on photovoltaic performance. [14] On the other hand, current-voltage measurements often showed a hysteresis that is rarely seen in other photovoltaic technologies. [15] These topics are highlighted in Sections 3 and 4. Finally, in Section 5 we discuss the framework for market introduction, such as cost reduction by choosing low-cost charge transport layers, or how the lifetime of perovskite absorbers can be extended by the choice of materials composition.Hybrid metal halide perovskites have become one of the hottest topics in optoelectronic materials research in recent years. Not only have they surpassed everyone's expectations and achieved similar performance as tried and true polycrystalline silicon photovoltaic devices, but they are also finding applications in a variety of different fields, including lighting. The main advantages of hybrid metal halide perovskites are simple processability, compatible with large-scale solution processing such as roll-to-roll printing, a...

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SFX as a low-cost ‘Spiro’ hole-transport material for efficient perovskite solar cells

Abstract: Four spiro[fluorene-9,9′-xanthene] (SFX) derivatives, SFX-TAD, SFX-TCz, SFX-TPTZ and SFX-MeOTAD have been synthesized for use as hole-transport materials and fully characterized by 1H/13C NMR spectroscopy, mass spectrometry, XRD and DSC.

Cited by 113 publications

References 35 publications

Facilely Synthesized spiro[fluorene‐9,9′‐phenanthren‐10′‐one] in Donor–Acceptor–Donor Hole‐Transporting Materials for Perovskite Solar Cells

Facilely Synthesized spiro[fluorene‐9,9′‐phenanthren‐10′‐one] in Donor–Acceptor–Donor Hole‐Transporting Materials for Perovskite Solar Cells

Spiro‐Phenylpyrazole‐9,9′‐Thioxanthene Analogues as Hole‐Transporting Materials for Efficient Planar Perovskite Solar Cells

Capturing the Sun: A Review of the Challenges and Perspectives of Perovskite Solar Cells

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