Chalcogenophene Comonomer Comparison in Small Band Gap Diketopyrrolopyrrole-Based Conjugated Polymers for High-Performing Field-Effect Transistors and Organic Solar Cells

Ashraf, Raja Shahid; Meager, Iain; Nikolka, Mark; Kirkus, Mindaugas; Planells, Miquel; Schroeder, Bob C.; Holliday, Sarah; Hurhangee, Michael; Nielsen, Christian B.; Sirringhaus, Henning; McCulloch, Iain

doi:10.1021/ja511984q

Cited by 377 publications

(329 citation statements)

References 48 publications

(76 reference statements)

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“…= 866 nm) can be used to generate bulk heterojunction solar cells with PCE values in the range of 5.07.1%, with both inverted and conventional device architectures reported. 26 In related studies by Jo and co-workers, the isoindigotellurophene polymer 18 was prepared and shown to exhibit modest PCE values (1.1%) when blended with PC 61 BM ([6,6]-phenyl-C61-butyric acid methyl ester). 28 …”

Section: New Routes To Tellurium Heterocycles and Post-functionalizatmentioning

confidence: 99%

“…23 The same group reported solar cells consisting of molecular donor molecules with capping benzotellurophene substituents, leading to elevated PCE values of up to 5.8%. 25 The use of 2,5-bis(trimethylstannyl)tellurophene (15) as a synthon to prepare conducting polymers via Stille coupling has been reported recently by both Ashraf (polymer 16) 26 and Choi (polymer 17).…”

Section: New Routes To Tellurium Heterocycles and Post-functionalizatmentioning

confidence: 99%

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Tellurophenes and Their Emergence as Building Blocks for Polymeric and Light-emitting Materials

Rivard

2015

Chemistry Letters

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Section: New Routes To Tellurium Heterocycles and Post-functionalizatmentioning

confidence: 99%

Section: New Routes To Tellurium Heterocycles and Post-functionalizatmentioning

confidence: 99%

Tellurophenes and Their Emergence as Building Blocks for Polymeric and Light-emitting Materials

Rivard

2015

Chemistry Letters

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“…It is well known that large crystals show high stability and that the morphology stability of the active layer affects the device performance. [63][64][65][66][67][68] Aside from that, using a phase-separation strategy to achieve self-ecapsulation has also been found to be very effective. In 2008, Kang et al used this method and mixed TIPS-pentacene with two different molecular weight PαMS ( Figure 5).…”

Section: Api Effects On Stability Of Ofetsmentioning

confidence: 99%

Engineering of Amorphous Polymeric Insulators for Organic Field‐Effect Transistors

Jiang

Guo

Liu

2017

Adv Elect Materials

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Organic field‐effect transistors (OFETs) have received considerable attention across the world due to their potential applications in integrated circuits for large‐area, flexible and low‐cost electronics, and a series of breakthroughs in their research have been made in the past decade. Although numerous novel organic semiconductive materials with outstanding properties have been synthesized, the fabrication of OFETs and the investigation of amorphous polymer insulators (APIs) are attracting more and more research interest due to their significance in semiconductor growth, charge transport and device stability. In this review, an introduction to APIs and OFETs is given, and the following aspects are then successively discussed: commonly used APIs in OFETs, applications of API in high‐performance OFETs, low‐energy‐consumption OFETs, functional OFETs, and self‐healing OFETs. In the last section, a projection of some future trends for APIs in OFETs is presented.

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“…For example, chalcogenophene-diketopyrrolopyrrole copolymers behave as active materials in polymer/fullerene bulk heterojunction solar cells with energy conversion efficiencies above 7%. [11] Using different chalcogenophenes in polymeric semiconductors is an efficient bandgap engineering strategy. [12] Herein, we report the systematic study of AIID-chalcogenophene polymers (PAIID), exploring the impact of structural variation on charge transport properties.…”

Section: Introductionmentioning

confidence: 99%

Tuning Frontier Orbital Energetics of Azaisoindigo‐Based Polymeric Semiconductors to Enhance the Charge‐Transport Properties

Huang

Chen

Mao

et al. 2017

Adv Elect Materials

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Crucial to the development of polymeric semiconductors has been the establishment of structure-property correlations to achieve high-mobility and versatile devices. [2] Despite the continuing improvement of carrier mobilities, a clear understanding of charge transport mechanisms and the relationship between device function and molecular structure are yet to be fully explored. Thanks to the thirdgeneration donor-acceptor (D-A) alternating conjugated copolymers, tunable comonomers are able to be incorporated into the backbone, evolving in the diversity and complexity to deeply investigate the influencing factors. [3] Coplanarity, π-conjugation, linearity, symmetry, frontier molecular orbital (FMO) energy, heteroatom effect, molecular weight, and density of side chains, to name but a few, are usually deemed critical in the structural and conformational control for rational design of conjugated polymers. When attempting to gain insight into these sophisticated factors, one might select a state-of-the-art building block and adjust the other moiety to fine-tune electronic and solid-state structures. A delicate compromise between such factors is also needed to achieve the optimal device performance. [4] Exploring new structures to boost device performance has always been the motivation of synthetic scientists. [1c,h,5] During the past few years, bislactam or bisimide has emerged as electron-withdrawing building blocks for high-performance semiconductors. For example, field-effect transistors of diketopyrrolopyrrole-, isoindigo-, and naphthalenediimide-based polymeric semiconductors exhibit mobilities of 1-10 cm 2 V −1 s −1 , which are comparable to inorganic counterparts. [1c,d] The incorporation of bislactam or bisimide provides three major advantages: (a) the electron deficient nature of these functional groups lowers the FMO energy levels to stabilize injected charge carriers and enhances stacking interactions between π-orbitals by depleting electron density and subsequently relieving electrostatic repulsion; [6] (b) the presence of intramolecular throughspace interactions minimizes dihedral torsions and promotes backbone coplanarity; [1c] (c) readily introduced side chains can not only tune the polymer aggregation tendency but also ensure solution processability. [3b] Among these bislactam-orTo establish a structure-property relationship between polymer backbone structures and field-effect transistor performance has emerged as a new topic in organic electronics. The tunability and diversity of organic semiconductors provide the feasibility of controlling the electrical properties. Herein the characterization of thienothiophene-, dithiophenylethene-, biselenophene-, and diselenophenylethene-containing azaisoindigo copolymers is presented. As suggested by both theoretical calculations and experimental results, backbone electronic structure and linearity, density of side chains, aggregation, and thin film microstructure are involved in the differences in optical and electrical properties of these polymers. As...

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Chalcogenophene Comonomer Comparison in Small Band Gap Diketopyrrolopyrrole-Based Conjugated Polymers for High-Performing Field-Effect Transistors and Organic Solar Cells

Cited by 377 publications

References 48 publications

Tellurophenes and Their Emergence as Building Blocks for Polymeric and Light-emitting Materials

Tellurophenes and Their Emergence as Building Blocks for Polymeric and Light-emitting Materials

Engineering of Amorphous Polymeric Insulators for Organic Field‐Effect Transistors

Tuning Frontier Orbital Energetics of Azaisoindigo‐Based Polymeric Semiconductors to Enhance the Charge‐Transport Properties

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