Structure–property relationships for bis-diketopyrrolopyrrole molecules in organic photovoltaics

Wang, Q.; Franeker, Jacobus J. van; Bruijnaers, Bardo J.; Wienk, MM Martijn; Janssen, Raj René

doi:10.1039/c6ta01533f

Cited by 35 publications

(18 citation statements)

References 111 publications

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“…The position, length, and stereoisomerism of the aliphatic chains attached to the aromatic backbone of the semiconductor small molecules is known to affect the morphology in the solid state, and thereby the optoelectronic properties and the photovoltaic performance. By introducing hexyl side chains on different positions of the terminal thiophene rings, we find that it is possible to effectively tune the packing in thin films between H‐like and J‐like aggregates.…”

Section: Introductionmentioning

confidence: 99%

The Effect of H‐ and J‐Aggregation on the Photophysical and Photovoltaic Properties of Small Thiophene–Pyridine–DPP Molecules for Bulk‐Heterojunction Solar Cells

Más‐Montoya

Janssen

2017

Adv Funct Materials

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261

195

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(1 of 12) 1605779 structure, and the perfectly reproducible synthetic procedures that largely avoid the variability between different batches seen in polymerizations. Recently, successful small-molecule donor systems have been reported that reach high power conversion efficiencies (PCEs) in organic solar cells. [2] The combination of a judicious molecular design with the optimal material processing conditions and device engineering remains a critical point for the success in the photoenergy conversion process. Rational molecular design is of great importance for further improving the photovoltaic performance of small-molecule bulk-heterojunction organic solar cells. However, achieving a high performance employing newly designed small-molecule materials remains a challenge because it is difficult to predict in sufficient detail how mole cules assemble in thin films and how this affects photovoltaic performance.When small-molecule chromophores assemble in the solid state, they often form H-type or J-type aggregates, depending on the relative alignment of the transition dipole moments on adjacent molecules. In an H-aggregate, molecules stack predominantly face-to-face, while J-aggregates form when molecules primarily stack in a head-to-tail arrangement. The formation of such aggregates has important consequences for the energies of the excited states and the oscillator strengths of the transitions to these states from the ground state. Consequently, H-and J-aggregation can strongly modify optical absorption and the photoluminescence spectra. To contribute to our understanding of the effect of molecular packing on photovoltaic performance, it is of interest to assemble one type of molecule in different packing modes.In this contribution, we do that by using molecules based on diketopyrrolopyrrole (DPP) flanked by two 5-(thiophen-2-yl) pyridin-2-yl units in which solubilizing hexyl side chains are introduced on the free positions of the peripheral thiophene units (Scheme 1). The DPP fragment has been extensively explored for organic semiconductors, because of its strong optical absorption and excellent charge transport properties, [3] especially for the design of materials for organic photovoltaic applications. [4] The electron density of the DPP core can be modified by employing different (hetero)aromatic flanking groups. The combination of DPP with two flanking pyridin-2-yl moieties leads to the simultaneous decrease of the frontier energy levels due to the electron-withdrawing nature of

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Section: Introductionmentioning

confidence: 99%

The Effect of H‐ and J‐Aggregation on the Photophysical and Photovoltaic Properties of Small Thiophene–Pyridine–DPP Molecules for Bulk‐Heterojunction Solar Cells

Más‐Montoya

Janssen

2017

Adv Funct Materials

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261

195

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“…In addition, the easy functionalization of its nitrogen atom with the presence of different linkage sites makes them suitable candidates in the tuning of polymer optoelectronic properties . However, carbazole is not actively used in donor moiety of recent high performance D–A copolymers for OFETs and OPVs in comparison to the thiophene‐based derivatives such as bithiophene (BT), thieno‐[3,2‐b]thiophene, and thienylenevinylene due to their relatively low charge carrier mobility …”

Section: Introductionmentioning

confidence: 99%

Bis‐Diketopyrrolopyrrole and Carbazole‐Based Terpolymer for High Performance Organic Field‐Effect Transistors and Infra‐Red Photodiodes

Opoku

Lim

Shin

et al. 2019

Macro Chemistry & Physics

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Carbazoles constitute one of the most widely used donor moieties for organic semiconductors due to their excellent hole transport and high environmental stability. However, they are seldomly used in recent high performance donor–acceptor (D–A) copolymers. In the present study, a planar regular terpolymer, PCbisDPP, composed of carbazole and thiophene flanked bis‐diketopyrrolopyrrole (bis‐DPP) for application as an active layer for high‐performance organic devices is reported. Organic field‐effect transistors with PCbisDPP as the active layer exhibit field‐effect mobility up to 1.48 cm2 v−1 s−1, which to the best of the current knowledge corresponds to the highest hole mobility reported to date for carbazole‐based D–A polymers. The high mobility is achieved via a tailored polymer‐design resulting in high crystallinity and a strong aggregating property without sacrificing solubility. PCbisDPP is applied as an active donor material in organic photodiode with fullerene derivative PC61BM as an acceptor in a bulk heterojunction blend. Binary additive combinations (tetralin: 1,8‐diiodooxtane (3:3) v/v%) utilization achieves an impressive performance with an external quantum efficiency of 80%, an average responsivity of 309.1 mA W−1, and specific detectivity of 4.73 × 1011 Jones in the near infra‐red light region (730 nm) utilizing a simple single layer organic photodiode structure as ITO/PEDOT:PSS/PCbisDPP:PC61BM/LiF/Al.

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“…37 Furthermore, it is worth noting that the charge mobility can been improved through introducing extended aromatic bridges to the DPP derivatives. 38 Recently, DPP-based DDP-pyrene-DDP type molecules have been reported for use as donor material for SMOSCs. It was found that these molecules exhibited high hole mobility and PCEs for SMOSCs applications.…”

Section: Variety Of Structures Including A-d-a D-a-d D-p-a D-p-dmentioning

confidence: 99%

Improving optoelectronic and charge transport properties of D–π–D type diketopyrrolopyrrole-pyrene derivatives as multifunctional materials for organic solar cell applications

Jin

Han

2019

RSC Adv.

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Structure–property relationships for bis-diketopyrrolopyrrole molecules in organic photovoltaics

Cited by 35 publications

References 111 publications

The Effect of H‐ and J‐Aggregation on the Photophysical and Photovoltaic Properties of Small Thiophene–Pyridine–DPP Molecules for Bulk‐Heterojunction Solar Cells

The Effect of H‐ and J‐Aggregation on the Photophysical and Photovoltaic Properties of Small Thiophene–Pyridine–DPP Molecules for Bulk‐Heterojunction Solar Cells

Bis‐Diketopyrrolopyrrole and Carbazole‐Based Terpolymer for High Performance Organic Field‐Effect Transistors and Infra‐Red Photodiodes

Improving optoelectronic and charge transport properties of D–π–D type diketopyrrolopyrrole-pyrene derivatives as multifunctional materials for organic solar cell applications

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