A review on triphenylamine (TPA) based organic hole transport materials (HTMs) for dye sensitized solar cells (DSSCs) and perovskite solar cells (PSCs): evolution and molecular engineering

Agarwala, Pooja; Kabra, Dinesh

doi:10.1039/c6ta08449d

Cited by 323 publications

(225 citation statements)

References 269 publications

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“…Triphenylamine (TPA) derivatives are a class of versatile redox‐active molecules that have attracted particular attention in relation to their promising hole transport properties . Applications include various thin layer opto‐electronic devices comprising organic light emitting diodes (OLEDs), electrochromic devices, dye sensitized solar cells, organic solar cells (OSCs) and perovskite solar cells . The electron‐rich character of TPA has also been exploited for electrochemical storage of energy and electrical memory devices .…”

Section: Introductionmentioning

confidence: 99%

Triphenylamine and some of its derivatives as versatile building blocks for organic electronic applications

Blanchard

Malacrida

Cabanetos

et al. 2018

Polymer International

109

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This review article gives an overview of past and current activities in the Linear Conjugated Systems Group of Angers and in the IPOC – Functional Polymers Group of the Institute of Polymer Chemistry of Stuttgart on the use of triphenylamine (TPA) as versatile building block for organic electronics. In the first part, the properties of TPA itself are introduced including geometrical and energy level considerations. Dimerization of TPA to tetraphenylbenzidine upon electrochemical oxidation is highlighted. The blocking of TPA para‐positions and its implications in terms of electroactivity is further discussed. The second part shows that dimerization of TPA as pendant redox‐active moieties in polymers is a versatile strategy to crosslink polymer films. Coming from redox homopolymers the crosslinking strategy is extended towards conjugated redox polymers based on polythiophenes and block copolymers. Conductivity mechanisms and the influence of doping level on conductivity are probed with cyclic voltammetry coupled with in situ conductance and four‐point probe measurements. The last part is dedicated to the use of TPA as an electron‐donating block in the design of donor‐π‐acceptor chromophores and their use as active material in organic photovoltaics. An overview of some relevant TPA‐based push–pull molecules from the literature and our contribution to this field is presented emphasizing the progress of the photovoltaic performance of organic solar cells made over the last decade. © 2018 Society of Chemical Industry

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Section: Introductionmentioning

confidence: 99%

Triphenylamine and some of its derivatives as versatile building blocks for organic electronic applications

Blanchard

Malacrida

Cabanetos

et al. 2018

Polymer International

109

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“…[10][11][12] Organic HTMs are amenable to low-temperature solution processing while also being capable of mediating high power conversion efficiencies (PCEs). [13,14] Spiro-OMeTAD [15] ( Figure 1) is aw idely used organic HTM and is capable of reaching PCEs greater than 20 %w hen integrated in PSCs. [16,17] However, Spiro-OMeTAD is expensive to manufacture because the tetrahedral spiro carbon that bridges the two perpendicular fluorene moieties (9,9'-spirobifluorene) can only be accessed through as uccession of substitution, lithiation, condensation and bromination steps.…”

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confidence: 99%

Precise Control of Thermal and Redox Properties of Organic Hole‐Transport Materials

et al. 2018

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We report design principles of the thermal and redox properties of synthetically accessible spiro-based hole transport materials (HTMs) and show the relevance of these findings to high-performance perovskite solar cells (PSCs). The chemical modification of an asymmetric spiro[fluorene-9,9'-xanthene] core is amenable to selective placement of redox active triphenylamine (TPA) units.W etherefore leveraged computational techniques to investigate five HTMs bearing TPAgroups judiciously positioned about this asymmetric spiro core.Itwas determined that TPAg roups positioned about the conjugated fluorene moiety increase the free energy change for holeextraction from the perovskite layer,w hile TPAs about the xanthene unit govern the T g values.T he synergistic effects of these characteristics resulted in an HTM characterized by both al ow reduction potential ( % 0.7 Vv s. NHE) and ah igh T g value (> 125 8 8C) to yield adevice power conversion efficiency (PCE) of 20.8 %inaP SC.

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“…The TGA measurements demonstrate a stable alkoxy‐PTEG even under high temperatures (Figure d). In addition, no peaks were observed in the DSC curve, thereby indicating amorphous characteristics which would be favorable for device operation and stability (inset in Figure d) …”

Section: Resultsmentioning

confidence: 99%

Nonaromatic Green‐Solvent‐Processable, Dopant‐Free, and Lead‐Capturable Hole Transport Polymers in Perovskite Solar Cells with High Efficiency

Lee

Kim

et al. 2020

Advanced Energy Materials

152

117

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With the recent developments in the efficiency of perovskite solar cells (PSCs), diverse functionalities are necessary for next‐generation charge‐transport layers. Specifically, the hole‐transport layer (HTL) in the various synthesized materials modified with functional groups is explored. A novel donor–acceptor type polymer, alkoxy‐PTEG, composed of benzo[1,2‐b:4,5:b′]dithiophene and tetraethylene glycol (TEG)‐substituted 2,1,3‐benzothiadiazole is reported. The alkoxy‐PTEG exhibits high solubility even in nonaromatic solvents, such as 3‐methylcyclohexanone (3‐MC), and can prevent possible lead leakage via chelation. The optical and electronic properties of alkoxy‐PTEG are thoroughly analyzed. Finally, a dopant‐free alkoxy‐PTEG device processed with 3‐MC exhibits 19.9% efficiency and a device with 2‐methyl anisole, which is a reported aromatic food additive, exhibits 21.2% efficiency in a tin oxide planar structure. The PSC device shows 88% stability after 30 d at ambient conditions (40–50% relative humidity and room temperature). In addition, nuclear magnetic resonance reveals that TEG groups can chelate lead ions with moderate strength (Kbinding = 2.76), and this strength is considered to be nondestructive to the perovskite lattice to prevent lead leakage. This is the first report to consider lead leakage and provide solutions to reduce this problem.

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A review on triphenylamine (TPA) based organic hole transport materials (HTMs) for dye sensitized solar cells (DSSCs) and perovskite solar cells (PSCs): evolution and molecular engineering

Abstract: Development of triphenylamine (TPA) based hole-transporting-materials (HTMs) leading to highTg, higher morphological stability and longevity of dye-sensitized and perovskite solar cells.

Cited by 323 publications

References 269 publications

Triphenylamine and some of its derivatives as versatile building blocks for organic electronic applications

Triphenylamine and some of its derivatives as versatile building blocks for organic electronic applications

Precise Control of Thermal and Redox Properties of Organic Hole‐Transport Materials

Nonaromatic Green‐Solvent‐Processable, Dopant‐Free, and Lead‐Capturable Hole Transport Polymers in Perovskite Solar Cells with High Efficiency

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