Utilization of simply alkylated diketopyrrolopyrrole derivative as a p-channel semiconductor for organic devices

Kwon, Ji-Seon; Na, Hanah; Palai, Akshaya K.; Jeong, Ui‐Jin; Cho, Sung‐Woo; Pyo, Seungmoon

doi:10.1016/j.synthmet.2015.07.015

Cited by 12 publications

(8 citation statements)

References 29 publications

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“…First reported in 1974, diketopyrrolopyrroles (DPPs) are ubiquitously employed in industry as high performance organic pigments, owing to their highly desirable coloristic and fastness properties. − More recently, materials based upon DPPs have attracted interest as promising charge transfer mediating materials in optoelectronic devices such as organic light emitting diodes, organic field effect transistors, and organic photovoltaics for solar energy conversion. − The concept of enhanced dimensionality in DPP containing architectures has been reported, although this has focused mainly on an increase in molecular dimensionality based around linear conjugated and nonconjugated systems . In star-shaped molecules such as those described, strong quadrupole based aggregation in the solid state limits charge carrier performance in field effect transistor applications.…”

Section: Introductionmentioning

confidence: 99%

Fluorine Directed Two-Dimensional Cruciform π–π Stacking in Diketopyrrolopyrroles

Calvo‐Castro

Morris

Kennedy

et al. 2016

Crystal Growth & Design

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Enhanced bulk dimensionality in organic materials employed in optoelectronic devices is desirable and can overcome fabrication issues related to structural defects and grain boundaries. Herein, we report a novel fluorinated diketopyrrolopyrrole single crystal structure, which displays a unique, mutually orthogonal, 2-dimensional cruciform π-π stacking arrangement. The crystal structure is characterised by an unusually large number of nearest neighbour dimer pairs which contribute to a greater thermal integrity than structurally analogous equivalents. Binding energies and charge transfer integrals were computed for all of the crystal 2 extracted dimer pairs by means of M06-2X density functional at 6-311G(d) level. Although weak, a number of intermolecular interactions involving organic fluorine (C-F---H, πF---π and C-F---πF) were identified to influence the supramolecular assembly of these dimer pairs. Charge transfer integrals for the two π-π stacking crystal dimers were determined using the energy splitting in dimer method. Ambipolar charge transport favouring electron transfer approaching that of rubrene is predicted in both of these π-π stacks with a greater magnitude of coupling observed from those dimers perpetuating along the crystallographic a-axis. Charge transport behaviour in the single crystal is greatly influenced by selective fluorination of the N-benzyl substituents and is consistent with the crystal extracted π-π stacking dimer geometries and their overall influence on wavefunction overlap. The reported structure is an interesting electron transport material that could be exploited, particularly in thin film based optoelectronic devices, where high bulk dimensionality is required.

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Section: Introductionmentioning

confidence: 99%

Fluorine Directed Two-Dimensional Cruciform π–π Stacking in Diketopyrrolopyrroles

Calvo‐Castro

Morris

Kennedy

et al. 2016

Crystal Growth & Design

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“…5,8,9 Diketopyrrolopyrrole (DPP) based materials are exciting charge transfer mediators, with high mobilities reported in organic field effect transistors (OFETs). [10][11][12][13][14][15][16][17][18][19][20][21][22][23][24][25][26] Our group are engaged in the rational design of crystalline and thin film DPP architectures [27][28][29][30][31][32][33] and have demonstrated in a number of phenyl core-substituted N-benzyl DPPs that small structural variations, particularly involving halogenation, can profoundly influence supramolecular packing via manipulation of single crystal intermolecular interactions. 28,29,31,32 We have pioneered the application of Truhlar's M06-2X density functional in the theoretical analysis of charge transfer integrals, reorganisation energies and interaction energetics in DPPs, [27][28][29][30][31][32][33] many of which are comparable or supersede those computed for the single crystal structures of state of the art organic semiconductors such as rubrene.…”

Section: Introductionmentioning

confidence: 99%

Twist and shout: a surprising synergy between aryl and N-substituents defines the computed charge transport properties in a series of crystalline diketopyrrolopyrroles

et al. 2016

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This version is available at https://strathprints.strath.ac.uk/58791/ Strathprints is designed to allow users to access the research output of the University of Strathclyde. Unless otherwise explicitly stated on the manuscript, Copyright © and Moral Rights for the papers on this site are retained by the individual authors and/or other copyright owners. Please check the manuscript for details of any other licences that may have been applied. You may not engage in further distribution of the material for any profitmaking activities or any commercial gain. You may freely distribute both the url (https://strathprints.strath.ac.uk/) and the content of this paper for research or private study, educational, or not-for-profit purposes without prior permission or charge.Any correspondence concerning this service should be sent to the Strathprints administrator: strathprints@strath.ac.ukThe Strathprints institutional repository (https://strathprints.strath.ac.uk) is a digital archive of University of Strathclyde research outputs. It has been developed to disseminate open access research outputs, expose data about those outputs, and enable the management and persistent access to Strathclyde's intellectual output. Journal Name ARTICLEThis journal is © The Royal Society of Chemistry 20xx J. Name., 2013, 00, 1-3 | 1 The influence of systematic variation of aryl and N-substitution on predicted charge transport behaviour in a series of crystalline diketopyrrolopyrroles is evaluated. A correct combination of substituents is revealed to maximise those properties which dictate device performance in organic single crystals based upon this structural motif. For electron transport, furan and N-alkyl substitution emerge as optimal molecular design strategies, whilst phenyl structures bearing N-benzyl substituents are shown to offer the most significant promise as highly sought after crystalline hole transport materials. IntroductionIn crystalline charge mediating organic materials, control of molecular solid state aggregation -can exert a dramatic impact on intermolecular electronic properties which define delocalised band transport and localised, thermally activated hopping of charge carriers. [1][2][3][4] Electronic coupling, or charge transfer integrals for hole/electron transport, t h/e , describe the extent of wavefunction overlap and are related to the strength of the -and play a significant role in either description. [5][6][7] Inner-sphere reorganisation energy for holes/e h/e , characterises the change in energy between charged and neutral molecular states, owing to geometrical relaxation of the localised molecular environment and can be detrimental to transport behaviour when charge hopping is predominant. Large E CP , are highly desirable in organic semiconductors to preserve the integrity of crystalline intermolecular interactions involving -Thermally--ing domains can result in considerable variation in t h/e , which can ultimately be detrimental to carrier mobility. Regardless of the mechanism of charge transport involved...

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“…Finally, we explored the effect of band boundary incoherence on the linear retardance of coumarin and the charge transport properties of organic semiconductor 2,5-didodecyl-3,6-di-(thiophen-2-yl)pyrrolo [3,4-c]pyrrole-1,4(2H,5H)-dione (DPP-C12). 35 ■ RESULTS AND DISCUSSION Band Boundary Incoherence. Banded spherulites show sharp changes in interference colors when viewed between crossed polarizers by virtue of the helicoidal precession of the crystal refractivity.…”

Section: ■ Introductionmentioning

confidence: 99%

“…This knowledge may find potential applications in organic semiconductor electronics. It has been well established that grain boundaries act as bottlenecks to charge transport in devices comprising polycrystalline organic active layers. , In spherulitic films, the mobility decreases with decreasing spherulite size due to the higher density of grain boundaries. − Therefore, researchers have been advancing strategies to increase domain size; single crystals are typically viewed as the gold standard. , On the other hand, our group previously studied the effect of crystal twisting on carrier mobility of three tetracyanoethylene-based CTCs and a monocomponent organic semiconductor BDT and demonstrated that a greater number of small gaps in twisted crystal films leads to higher mobilities than a fewer number of big gaps in straight crystal films.…”

Section: Introductionmentioning

confidence: 99%

Coherence in Polycrystalline Thin Films of Twisted Molecular Crystals

Yang,

Shtukenberg,

Zhou

et al. 2024

Chem. Mater.

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Helicoidal crystallites in rhythmically banded spherulites manifest spectacular optical patterns in small molecules and polymers. It is shown that concentric optical bands indicating crystallographic orientations typically lose coherence (in-phase twisting) with growth from the center of nucleation. Here, coherence is shown to increase as the twist period decreases for seven molecular crystals grown from the melt. This dependence was correlated to crystallite fiber thickness and length, as well as crystallite branching frequency, a parameter that was extracted from scanning electron micrographs, and supported by numerical simulations. Hole mobilities for 2,5-didodecyl-3,6-di-(thiophen-2-yl)pyrrolo[3,4-c]pyrrole-1,4(2H,5H)-dione (DPP-C12) measured by using organic field-effect transistors demonstrated that more incoherent boundaries between optical bands in spherulites lead to higher charge transport for films with the same twist period. This was rationalized by combining our growth model with electrodynamic simulations. This work illustrates the emergence of complexity in crystallization processes (spherulite formation) that arises in the extra variable of helicoidal radial twisting. The details of the patterns analyzed here link the added complexity in crystal growth to the electronic and optical properties of the thin films.

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Utilization of simply alkylated diketopyrrolopyrrole derivative as a p-channel semiconductor for organic devices

Cited by 12 publications

References 29 publications

Fluorine Directed Two-Dimensional Cruciform π–π Stacking in Diketopyrrolopyrroles

Fluorine Directed Two-Dimensional Cruciform π–π Stacking in Diketopyrrolopyrroles

Twist and shout: a surprising synergy between aryl and N-substituents defines the computed charge transport properties in a series of crystalline diketopyrrolopyrroles

Coherence in Polycrystalline Thin Films of Twisted Molecular Crystals

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