Efficient solution processed D1-A-D2-A-D1 small molecules bulk heterojunction solar cells based on alkoxy triphenylamine and benzo[1,2-b:4,5-b′]thiophene units

Kumar, Challuri Vijay; Cabau, Lydia; Koukaras, Emmanuel Ν.; Sharma, Ganesh D.; Palomares, Emilio

doi:10.1016/j.orgel.2015.07.014

Cited by 18 publications

(6 citation statements)

References 77 publications

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“…Finally, solution‐processed BHJ OSCs based on DAD‐5 gave a high PCE reaching 6.13%; this benzothiadiazole derivative is indeed a D 1 AD 2 AD 1 system with a central electron‐rich dithienobenzene flanked by two alkylated thiophene substituents …”

Section: Tpa‐based Push–pull Molecular Donors For Organic Photovoltaicsmentioning

confidence: 94%

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

Blanchard

Malacrida

Cabanetos

et al. 2018

Polymer International

107

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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: Tpa‐based Push–pull Molecular Donors For Organic Photovoltaicsmentioning

confidence: 94%

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

Blanchard

Malacrida

Cabanetos

et al. 2018

Polymer International

107

View full text Add to dashboard Cite

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“…The b19 :PC 61 BM based devices show the highest V OC of 1.11 V owing to the lowest HOMO energy level of b19 ; the J SC of b18 (13.60 mA cm –2 ) and b20 (14.00 mA cm –2 ) based devices are higher than those of b17 (10.48 mA cm –2 ) and b19 (11.20 mA cm –2 ) based devices, which is consistent with the absorption and mobility; the PCEs of b17-b20 :PC 61 BM-based devices are 3.53%, 4.12%, 4.14%, and 4.86%, respectively. Palomares and co-workers synthesized molecule b21 (Figure ) with benzo[1,2- b :4,5- b ′]dithiophene (BDT) as the core, BT as the bridge, and alkoxy-substituted TPA as the end group . The BDT unit is a strong electron-donating group with planar conjugated structure, thus molecule b21 possesses a coplanar molecular backbone and shows broad absorption from 350 to 750 nm.…”

Section: Taa and Related Materials In Oscsmentioning

confidence: 96%

“…The hole mobilities (measured by SCLC) of b18 (1.6 × 10 −4 cm 2 V −1 s −1 ) and b20 (7.2 × 10 −4 cm 2 V −1 s −1 ) in blended films are higher than those of b17 (1.0 × 10 −5 Palomares and co-workers synthesized molecule b21 (Figure 6) with benzo[1,2-b:4,5-b′]dithiophene (BDT) as the core, BT as the bridge, and alkoxy-substituted TPA as the end group. 92 The BDT unit is a strong electron-donating group with planar conjugated structure, thus molecule b21 possesses a coplanar molecular backbone and shows broad absorption from 350 to 750 nm. The HOMO and LUMO energy levels of b21 are −5.13 eV and −3.08 eV, respectively.…”

Section: Chemical Reviewsmentioning

confidence: 99%

Triarylamine: Versatile Platform for Organic, Dye-Sensitized, and Perovskite Solar Cells

et al. 2016

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Triarylamine (TAA) and related materials have dramatically promoted the development of organic and hybrid photovoltaics during the past decade. The power conversion efficiencies of TAA-based organic solar cells (OSCs), dye-sensitized solar cells (DSSCs), and perovskite solar cells (PSCs) have exceeded 11%, 14%, and 20%, which are among the best results for these three kinds of devices, respectively. In this review, we summarize the recent advances of the high-performance TAA-based materials in OSCs, DSSCs, and PSCs. We focus our discussion on the structure-property relationship of the TAA-based materials in order to shed light on the solutions to the challenges in the field of organic and hybrid photovoltaics. Some design strategies for improving the materials and device performance and possible research directions in the near future are also proposed.

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“…The replacement of the active hydrogen by an alkyl group was found to be an efficient tool not only to increase the electrochemical stability of donor-acceptor small molecules, 15,16 but also to control their solubility and a number of important solid-state physical properties by simple adjustment of the alkyl chain length in the DCV substituent. 17,18 To fine-tune the energy levels in small molecules, some additional electron-donating blocks such as dithienosilole, [19][20][21][22] benzodithiophene, 23,24 and dithienopyrrole, 25 and etc., are often used. For the design of star-shaped molecules, a triphenylamine (TPA) core is one of the widely used electron-donating blocks due to its low cost, high electrochemical stability and hole transporting ability.…”

Section: Introductionmentioning

confidence: 99%

Star-shaped D–π–A oligothiophenes with a tris(2-methoxyphenyl)amine core and alkyldicyanovinyl groups: synthesis and physical and photovoltaic properties

et al. 2016

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Synthesis of a series of star-shaped oligomers having a novel electron donating tris(2-methoxyphenyl)-amine (m-TPA) core, which is linked through a bithiophene or terthiophene p-bridge with electrondeficient alkyldicyanovinyl (alkyl-DCV) groups, is described. A comprehensive study of the oligomers revealed significant dependence of their physical properties, including absorption, molecular frontier energy levels, crystal packing, and melting and glass transition temperatures, upon the chemical structure. A comparison of their photophysical properties to the nearest analog having the common dicyanovinyl (DCV) groups demonstrated a number of benefits to use alkyl-DCV units for the design of donor-acceptor small molecules: higher solubility, increased electrochemical stability, better photovoltaic performance, and possibility to control the relative physical and photovoltaic properties by a simple adjustment of alkyl and p-bridge lengths. Modification of the well-known triphenylamine (TPA) core in the star-shaped oligomers by methoxy groups increases not only solubility, but also crystallinity of the oligomers, whereas their photovoltaic performance stays on a similar level as their analogs with a TPA core. The study demonstrates that these design strategies represent interesting and simple tools for the effective modulation of properties of star-shaped molecules.

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Efficient solution processed D1-A-D2-A-D1 small molecules bulk heterojunction solar cells based on alkoxy triphenylamine and benzo[1,2-b:4,5-b′]thiophene units

Cited by 18 publications

References 77 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

Triarylamine: Versatile Platform for Organic, Dye-Sensitized, and Perovskite Solar Cells

Star-shaped D–π–A oligothiophenes with a tris(2-methoxyphenyl)amine core and alkyldicyanovinyl groups: synthesis and physical and photovoltaic properties

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