Enabling high-mobility, ambipolar charge-transport in a DPP-benzotriazole copolymer by side-chain engineering

Gruber, Matthias; Jung, Soo Yeon; Schott, Sam; Venkateshvaran, Deepak; Kronemeijer, Auke Jisk; Andreasen, Jens Wenzel; McNeill, Christopher R.; Wong, Wallace W. H.; Shahid, Munazza; Heeney, Martin; Lee, Jin‐Kyun; Sirringhaus, Henning

doi:10.1039/c5sc01326g

Cited by 94 publications

(77 citation statements)

References 65 publications

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“…3A, from which we extracted the activation energies (E A ) using the Arrhenius relation, μ ∝ exp(−E A /kT), where k is the Boltzmann constant. Interestingly, the plots show two different activation regimes, with a transition occurring at T ∼190 K (24,25). In the low-T regime, DPP2T shows an E A of ∼19 meV, which is fairly low compared with the values reported for other high-mobility polymers (26,27).…”

Section: Resultsmentioning

confidence: 74%

Optically transparent semiconducting polymer nanonetwork for flexible and transparent electronics

Park

Kim

et al. 2016

Proc. Natl. Acad. Sci. U.S.A.

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Simultaneously achieving high optical transparency and excellent charge mobility in semiconducting polymers has presented a challenge for the application of these materials in future "flexible" and "transparent" electronics (FTEs). Here, by blending only a small amount (∼15 wt %) of a diketopyrrolopyrrole-based semiconducting polymer (DPP2T) into an inert polystyrene (PS) matrix, we introduce a polymer blend system that demonstrates both high field-effect transistor (FET) mobility and excellent optical transparency that approaches 100%. We discover that in a PS matrix, DPP2T forms a web-like, continuously connected nanonetwork that spreads throughout the thin film and provides highly efficient 2D charge pathways through extended intrachain conjugation. The remarkable physical properties achieved using our approach enable us to develop prototype high-performance FTE devices, including colorless all-polymer FET arrays and fully transparent FET-integrated polymer light-emitting diodes.semiconducting polymer | organic electronics | flexible and transparent device | polymer blend | charge transport O ptically transparent and mechanically flexible circuitries have long been desired for next-generation electronics requiring unprecedented features, such as "see-through" visibility, deformability, and even skin-attachable functionality for health care systems (1-3). This new paradigm for electronic applications has motivated researchers to eagerly pursue new innovative semiconducting materials, and one promising candidate is the class of materials called semiconducting conjugated polymers (4). Their unique benefits, including mechanical flexibility, light weight, and processing advantages based on high-throughput fabrication processes using solution-printing technologies, have accelerated the development of these materials as key building blocks for next-generation ubiquitous systems (2, 5, 6). Nevertheless, these materials still cannot fulfill the ultimate requirements for future "flexible" and "transparent" electronics (FTEs). Together with their inferior charge-carrier mobility because of conformational and energetic disorder (7), their high light absorption in the visible range, which is inherent to this class of materials (absorption coefficient ∼10 5 cm −1 ) (8), makes it difficult to apply these materials in FTEs. Indeed, despite extensive investigations seeking a suitable model system for FTEs by varying the polymer-structure design and the processing techniques used, the simultaneous achievement of optical transparency and high mobility in semiconducting polymers remains a formidable challenge (9, 10).Among the various types of semiconducting polymers, lowbandgap polymers using the donor-acceptor (D-A) copolymerization scheme are promising candidate materials for FTE applications. These semiconducting copolymers usually exhibit much less absorption in the visible range compared with other typical midbandgap polymers because of their red-shifted π-π* absorption spectrum, which exhibits strong absorption in the ne...

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Section: Resultsmentioning

confidence: 74%

Optically transparent semiconducting polymer nanonetwork for flexible and transparent electronics

Park

Kim

et al. 2016

Proc. Natl. Acad. Sci. U.S.A.

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“…Recently, small conjugated molecules and polymers containing diketopyrrolopyrrole (DPP) received a lot of attention for application in organic light‐emitting devices, dye lasers, solar cells, and organic field‐effect transistors (OFETs) . Nowadays, the DPP‐based materials became a benchmark among organic semiconductors . Particularly, DPP‐based conjugated polymers have attained impressive hole mobility of 12 cm 2 /V s −1 , electron mobility of 3 cm 2 /V s −1 , and balanced ambipolar mobility with a ratio of hole to electron mobility of 1.18/1.86 cm 2 /V s −1 in OFETs .…”

Section: Introductionmentioning

confidence: 99%

A comparative analysis of symmetric diketopyrrolopyrrole‐cored small conjugated molecules with aromatic flanks: From geometry to charge transport

et al. 2018

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Diketopyrrolopyrrole (DPP) derivatives are promising compounds for application in organic electronics. Here, we investigate several symmetrical N‐unsubstituted and N‐methyl substituted DPPs which differ in the heteroatom in the aromatic flanks. The conformational, electronic, and optical properties are characterized for single molecules in vacuum or a solvent. The intermolecular interactions are evaluated for interacting dimers. Here, a number of stacking geometries is tested, and dimers with mutual orientation of the molecules corresponding to the minimal binding energies are determined. The predicted charge carrier mobilities for stacks having minimal binding energies corroborate experimentally measured values. We conclude that DFT prediction of such stacks is a promising and computationally inexpensive approach to a rough estimation of transport properties. Additionally, the super‐cell of the experimentally resolved crystal structure is used to study the dynamics and to compute the charge transport along the hopping pathways. We discuss obtained high mobilities and relate them to the symmetry of DPP core. © 2018 Wiley Periodicals, Inc.

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“…Ambipolar conjugated polymers, which transport holes and electrons simultaneously, have great potential in simple and low cost fabrication of light emitting field‐effect transistors (FETs) and complementary‐like inverter through one‐step printing process . The most effective way to realize ambipolar polymers is copolymerization of an electron donor and acceptor unit (D–A) having the same charge transport capability.…”

Section: Introductionmentioning

confidence: 99%

Controlling Ambipolar Charge Transport in Isoindigo‐Based Conjugated Polymers by Altering Fluorine Substitution Position for High‐Performance Organic Field‐Effect Transistors

Kim

Park

et al. 2019

Adv Funct Materials

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A molecular design strategy to achieve highly balanced ambipolar charge transport for donor–acceptor (D–A) isoindigo (IIG)‐based copolymer through systematic selection of fluorination positions is reported. To study fluorine substitution site effects on electronic and structural properties, two fluorinated IIG‐based copolymers (PIIG‐iFT2 and PIIG‐oFT2) are synthesized, which contain two fluorine atoms at the bithiophene (T2) inner and outer site and compare them with a nonfluorinated copolymer of IIG and T2 (PIIG‐T2) as the reference polymer. Fluorination at the outer site of T2 in PIIG‐oFT2 polymer effectively lowers molecular energy levels and increases molecular planarity more than fluorination at the T2 inner site. PIIG‐oFT2 organic field‐effect transistors show highly balanced ambipolar mobility, hole mobility (μh)/electron mobility (μe) = 1 by increasing electron mobility, whereas PIIG‐T2 (μh/μe = 9.0) and PIIG‐iFT2 (μh/μe = 2.4) exhibit unbalanced ambipolar transport. The ambipolar complementary‐like inverter is also demonstrated by simple one‐time coating of PIIG‐oFT2 with gain = 21.

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Enabling high-mobility, ambipolar charge-transport in a DPP-benzotriazole copolymer by side-chain engineering

Abstract: In this article we discuss the synthesis of four new low band-gap co-polymers based on the diketopyrrolopyrrole (DPP) and benzotriazole (BTZ) monomer unit.

Cited by 94 publications

References 65 publications

Optically transparent semiconducting polymer nanonetwork for flexible and transparent electronics

Optically transparent semiconducting polymer nanonetwork for flexible and transparent electronics

A comparative analysis of symmetric diketopyrrolopyrrole‐cored small conjugated molecules with aromatic flanks: From geometry to charge transport

Controlling Ambipolar Charge Transport in Isoindigo‐Based Conjugated Polymers by Altering Fluorine Substitution Position for High‐Performance Organic Field‐Effect Transistors

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