Recent Advances in the Development of Semiconducting DPP‐Containing Polymers for Transistor Applications

Nielsen, Christian B.; Turbiez, Mathieu; McCulloch, Iain

doi:10.1002/adma.201201795

Cited by 814 publications

(773 citation statements)

References 68 publications

(103 reference statements)

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“…However, through appropriate synthetic routes and rational molecular design, several n-type molecular and polymeric semiconductors have been synthesized exhibiting OTFT electron mobilities of 0.1-2.0 cm 2 V À1 s À1 under inert/nitrogen atmosphere as well as under ambient atmosphere. [16][17][18][19][20] By satisfying de Leeuw's hypothesis, our group has reported a high electron mobility of 3 cm 2 V À1 s À1 for a diketopyrrolopyrrolediketopyrrolopyrrole based conjugated polymer. 21 The polymer was substituted with hydrophobic and hydrophilic side-chains on alternate units of DPP.…”

Section: Introductionsupporting

confidence: 62%

Use of side-chain for rational design of n-type diketopyrrolopyrrole-based conjugated polymers: what did we find out?

Kanimozhi

Yaacobi‐Gross

Burnett

et al. 2014

Phys. Chem. Chem. Phys.

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The primary role of substituted side chains in organic semiconductors is to increase their solubility in common organic solvents. In the recent past, many literature reports have suggested that the side chains play a critical role in molecular packing and strongly impact the charge transport properties of conjugated polymers. In this work, we have investigated the influence of side-chains on the charge transport behavior of a novel class of diketopyrrolopyrrole (DPP) based alternating copolymers. To investigate the role of sidechains, we prepared four diketopyrrolopyrrole-diketopyrrolopyrrole (DPP-DPP) conjugated polymers with varied side-chains and carried out a systematic study of thin film microstructure and charge transport properties in polymer thin-film transistors (PTFTs). Combining results obtained from grazing incidence X-ray diffraction (GIXD) and charge transport properties in PTFTs, we conclude side-chains have a strong influence on molecular packing, thin film microstructure, and the charge carrier mobility of DPP-DPP copolymers. However, the influence of side-chains on optical properties was moderate. The preferential ''edge-on'' packing and dominant n-channel behavior with exceptionally high field-effect electron mobility values of 41 cm 2 V À1 s À1 were observed by incorporating hydrophilic (triethylene glycol) and hydrophobic side-chains of alternate DPP units. In contrast, moderate electron and hole mobilities were observed by incorporation of branched hydrophobic side-chains. This work clearly demonstrates that the subtle balance between hydrophobicity and hydrophilicity induced by side-chains is a powerful strategy to alter the molecular packing and improve the ambipolar charge transport properties in DPP-DPP based conjugated polymers. Theoretical analysis supports the conclusion that the side-chains influence polymer properties through morphology changes, as there is no effect on the electronic properties in the gas phase. The exceptional electron mobility is at least partially a result of the strong intramolecular conjugation of the donor and acceptor as evidenced by the unusually wide conduction band of the polymer.

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Section: Introductionsupporting

confidence: 62%

Use of side-chain for rational design of n-type diketopyrrolopyrrole-based conjugated polymers: what did we find out?

Kanimozhi

Yaacobi‐Gross

Burnett

et al. 2014

Phys. Chem. Chem. Phys.

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“…Various conjugated molecules and polymers have been investigated intensively 5, 6, 7, 8, 9, 10, 11. These studies reveal that intermolecular/interchain packing and thin film crystallinity play a vital role in determining the charge transporting properties 12, 13.…”

mentioning

confidence: 99%

A Facile Approach to Improve Interchain Packing Order and Charge Mobilities by Self‐Assembly of Conjugated Polymers on Water

et al. 2018

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Development of facile and economic approaches for assembling organic semiconductors into more ordered structures toward high charge mobilities is highly demanding for the fabrication of organic circuits. Here a simple and facile approach is reported to prepare conjugated polymer thin films with improved crystallinities and charge mobilities by self‐assembling semiconducting polymers on water. The formation of polymer thin films with more ordered structures is attributed to coffee ring effect induced by solvent‐evaporation on water, and the hydrophobic nature of conjugated polymers that forces the polymer chains to pack densely and orderly on water surface. This approach is applicable to typical semiconducting polymers, and charge mobilities of their thin films are boosted remarkably. Finally, this new method can be utilized to easily fabricate the array of field‐effect transistors with high charge mobilities in an economic way.

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“…18,[27][28][29] These conjugated D-A polymers have led to a number of p-type and ambipolar semiconducting properties with high charge carrier mobilities. For instance, Liu and co-workers designed and synthesized conjugated DPP-based polymer (DPPTTT) with thienothiophene (TT) as the electron-donating moieties, and OFETs with this polymer displayed high hole mobilities up to 10.5 cm 2 V − 1 s − 1 .…”

Section: Conjugated D-a Terpolymers For Applications In Ofetsmentioning

confidence: 99%

Conjugated D–A terpolymers for organic field-effect transistors and solar cells

Luo

Liu

Zhang

2017

Polym J

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The incorporation of additional electron donors or acceptors into the backbones of conjugated polymers with alternating donors and acceptors results in various conjugated D-A terpolymers. The presence of additional electron donors or acceptors in the conjugated backbones can modulate the electronic absorptions and highest occupied molecular orbital/lowest unoccupied molecular orbital levels, as well as interchain interactions and thin-film morphology. Because of these structural features, conjugated D-A terpolymers have been intensively investigated in recent years for applications in field-effect transistors and photovoltaic cells. In this review, we introduce the recent developments of conjugated D-A terpolymers with various combinations of electron donors and acceptors, and discuss the future perspectives for conjugated terpolymers. In recent decades, conjugated polymers have demonstrated promising applications in flexible, large-area and low-cost electronic devices, such as organic field-effect transistors (OFETs) 1-3 and solar cells (OSCs). [4][5][6][7] This is attributed to the conjugated electronic and polymeric structures of these polymers, resulting in semiconducting properties with good solution processability, mechanical property and thermal stability. 8,9 Among the conjugated polymers, conjugated alternating polymers consisting of both electron donors (D) and electron acceptors (A), referred to as conjugated D-A polymers, [10][11][12][13][14][15][16][17] have been extensively investigated in recent years. The studies indicate that electronic absorptions, highest occupied molecular orbital/lowest unoccupied molecular orbital (HOMO/LUMO) energies (and bandgaps), interchain interactions and thin-film morphologies of conjugated D-A polymers can be effectively tuned 10-17 by properly varying the electron donors and acceptors as well as the linkers. Consequently, the semiconducting performance of conjugated D-A polymers can be tuned in this way. In fact, polymeric p-type, n-type and even ambipolar semiconductors with high charge mobilities have been developed on the basis of conjugated D-A polymers. 18-21 Moreover, conjugated D-A polymers have been successfully utilized as either electron donors or acceptors for OSCs with high power conversion efficiencies (PCEs). [22][23][24][25] Apart from conjugated polymers with alternating electron donor and acceptor moieties, conjugated D-A terpolymers, which contain either one kind of acceptor/two types of electron donors (2D1A) or one kind of donor/two types of electron acceptors (1D2A) in the backbones as illustrated in Scheme 1, have received increased attention. It is expected that an additional dimension is generated for tuning the electronic structures of conjugated polymers and thus their absorptions and HOMO/LUMO levels as well as interchain packing 8,26 with such conjugated D-A terpolymers. Moreover, the combination of existing electron donors and acceptors can yield a huge number of terpolymers, which can be prepared in the same manner as conventional D-A ...

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Recent Advances in the Development of Semiconducting DPP‐Containing Polymers for Transistor Applications

Cited by 814 publications

References 68 publications

Use of side-chain for rational design of n-type diketopyrrolopyrrole-based conjugated polymers: what did we find out?

Use of side-chain for rational design of n-type diketopyrrolopyrrole-based conjugated polymers: what did we find out?

A Facile Approach to Improve Interchain Packing Order and Charge Mobilities by Self‐Assembly of Conjugated Polymers on Water

Conjugated D–A terpolymers for organic field-effect transistors and solar cells

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