Diacetylene bridged triphenylamines as hole transport materials for solid state dye sensitized solar cells

Planells, Miquel; Abate, Antonio; Hollman, Derek J.; Stranks, Samuel D.; Bharti, Vishal; Gaur, Jitender; Mohanty, Dibyajyoti; Chand, Suresh; Snaith, Henry J.; Robertson, Neil

doi:10.1039/c3ta11417a

Cited by 112 publications

(115 citation statements)

References 54 publications

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“…All of the HTMs employ methoxy groups which are reported to have a high tendency to stabilize the radical cations and also increase the hole mobility and solubility. [ 15,20,21 ] The materials were characterized by 1 H/ 13 C NMR and high resolution mass spectrometry (HR-MS) (Supporting Information Figure S1-S8). Additionally, Spiro-OMeTAD is employed as a reference HTM in this study.…”

Section: Design and Synthesismentioning

confidence: 99%

“…In an effort to solve these problems, many new HTMs have been proposed to improve hole mobility and optimize HOMO levels, yet the measured device effi ciencies still remain lower than Spiro-OMeTAD. [11][12][13][14][15] Most recently, some studies have used thiophene-based monomers to fi ll the pores followed by electropolymerization. [ 16 ] However, this method requires special processing procedures that may be diffi cult to actualize in large-scale production processes.…”

Section: Introductionmentioning

confidence: 99%

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Integrated Design of Organic Hole Transport Materials for Efficient Solid‐State Dye‐Sensitized Solar Cells

Bai

Tian

Lin

et al. 2014

Advanced Energy Materials

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A series of triphenylamine‐based small molecule organic hole transport materials (HTMs) with low crystallinity and high hole mobility are systematically investigated in solid‐state dye‐sensitized solar cells (ssDSCs). By using the organic dye LEG4 as a photosensitizer, devices with X3 and X35 as the HTMs exhibit desirable power conversion efficiencies (PCEs) of 5.8% and 5.5%, respectively. These values are slightly higher than the PCE of 5.4% obtained by using the state‐of‐the‐art HTM Spiro‐OMeTAD. Meanwhile, transient photovoltage decay measurement is used to gain insight into the complex influences of the HTMs on the performance of devices. The results demonstrate that smaller HTMs induce faster electron recombination in the devices and suggest that the size of a HTM plays a crucial role in device performance, which is reported for the first time.

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Section: Design and Synthesismentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Integrated Design of Organic Hole Transport Materials for Efficient Solid‐State Dye‐Sensitized Solar Cells

Bai

Tian

Lin

et al. 2014

Advanced Energy Materials

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“…Diacetylide-triphenylamine (DATPA) derivatives were first tried as HTM in ssDSSC with the organic D102 dye [29], where they showed encouraging efficiency of 1.16% against 2.96% for the cell with the Spiro-OMeTAD. In the field of perovskites solar cells, two kinds of DATPA derivatives have been associated with significant performance so far: the Me 2 N-DATPA and the MeO-DATPA, where Me 2 N and MeO are N(CH 3 ) 2 and OCH 3 groups, respectively [30].…”

Section: Tri-phenylamine Derivativesmentioning

confidence: 99%

π-Conjugated Materials as the Hole-Transporting Layer in Perovskite Solar Cells

Gheno

Vedraine

Ratier

et al. 2016

Metals

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Hybrid organometal halide perovskites have attracted much attention these past four years as the new active layer for photovoltaic applications. Researches are now intensively focused on the stability issues of these solar cells, the process of fabrication and the design of innovative materials to produce efficient perovskite devices. In this review, we highlight the recent progress demonstrated in 2015 in the design of new π-conjugated organic materials used as hole transporters in such solar cells. Indeed, several of these "synthetic metals" have been proposed to play this role during the last few years, in an attempt to replace the conventional 2,2 1 ,7,7 1 -tetrakis-(N,N-di-4-methoxyphenylamino)-9,9 1 -spirobifluorene (Spiro-OMeTAD) reference. Organic compounds have the benefits of low production costs and the abundance of raw materials, but they are also crucial components in order to address some of the stability issues usually encountered by this type of technology. We especially point out the main design rules to reach high efficiencies.

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“…We have prepared a new hole-transport material with a very strong hole-donor capability, adding to the redox-tunable series of substituted-DATPA HTMs we reported previously in the context of ssDSSC. 13 For the first time we have applied two DATPA molecules as the HTMs in perovskite solar cells leading to excellent efficiencies in both cases, despite the large difference in hole-donor strength. Close inspection indicates a trade-off in V OC with J SC as the HTM redox potential is changed, however the differences are perhaps not as great as might be expected; a 0.44 V difference in oxidation potential between the DATPA HTMs leads to only a 0.12 V difference in average V OC of the resulting cells.…”

mentioning

confidence: 99%

“…S4). 13 This involved a spin-coated layer of the HTM on an ITO/PEDOT-PSS substrate, followed by an evaporated gold counter electrode.…”

mentioning

confidence: 99%

Hole-transport materials with greatly-differing redox potentials give efficient TiO₂–[CH₃NH₃][PbX₃] perovskite solar cells

Abate

Planells

Hollman

et al. 2015

Phys. Chem. Chem. Phys.

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Two diacetylide-triphenylamine hole-transport materials (HTM) with varying redox potential have been applied in planar junction The recent development of lead halide perovskite based solar cells has led to a step change in the efficiencies of solution-processable solar cells culminating recently in certified power-conversion efficiencies reaching the range 16-18%. 1 The exceptional performance of these devices has been attributed to key properties of the perovskite layer including excellent electron and exciton mobility and direct band gap of appropriate energy for visible light harvesting. 2To date, Spiro-OMeTAD has been most commonly used as the HTM in the highest efficiency cells, however this material requires an expensive multi-step synthesis and shows holetransport too low to carry all generated current. 3,4 In response, there has been increased recent interest in developing new HTMs aimed at addressing these limitations. [3][4][5][6][7][8][9][10][11][12] This work has explored alternative HTM structures, in particular based on the triarylamine and carbazole motifs, 6-11 leading to impressive power-conversion efficiencies (PCE) reaching around 14%. (Fig. 1a) was synthesised by a similar route to that we already reported for MeO-DATPA. 13This involved Ullmann coupling to form the triarylamine fragment, followed by Sonogashira coupling to add a trimethylsilyl acetylide fragment and, after deprotection to remove the trimethylsilyl unit, a final oxidative homocoupling to form the central diacetylide unit (see ESI † for full details).Single crystals suitable for X-ray diffraction (XRD) were obtained by layer addition in EtOAc/DMSO. Me 2 N-DATPA crystallised in the space group P2 1 /n and showed one molecule in the asymmetric unit (ESI †). The structure is arranged with the central diacetylide moieties approximately parallel between molecules. As expected the geometry around each triphenylamine is approximately planar and viewed along the long molecular axis, the molecules form herringbone arrangements that run in alternating directions. No intermolecular interactions are within van der Waal radii, however the positioning of Me 2 N-groups on the periphery of the molecule enables

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Diacetylene bridged triphenylamines as hole transport materials for solid state dye sensitized solar cells

Cited by 112 publications

References 54 publications

Integrated Design of Organic Hole Transport Materials for Efficient Solid‐State Dye‐Sensitized Solar Cells

Integrated Design of Organic Hole Transport Materials for Efficient Solid‐State Dye‐Sensitized Solar Cells

π-Conjugated Materials as the Hole-Transporting Layer in Perovskite Solar Cells

Hole-transport materials with greatly-differing redox potentials give efficient TiO₂–[CH₃NH₃][PbX₃] perovskite solar cells

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Diacetylene bridged triphenylamines as hole transport materials for solid state dye sensitized solar cells

Cited by 112 publications

References 54 publications

Integrated Design of Organic Hole Transport Materials for Efficient Solid‐State Dye‐Sensitized Solar Cells

Integrated Design of Organic Hole Transport Materials for Efficient Solid‐State Dye‐Sensitized Solar Cells

π-Conjugated Materials as the Hole-Transporting Layer in Perovskite Solar Cells

Hole-transport materials with greatly-differing redox potentials give efficient TiO2–[CH3NH3][PbX3] perovskite solar cells

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Product

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Hole-transport materials with greatly-differing redox potentials give efficient TiO₂–[CH₃NH₃][PbX₃] perovskite solar cells