Naphthalenedicarboximide- vs Perylenedicarboximide-Based Copolymers. Synthesis and Semiconducting Properties in Bottom-Gate N-Channel Organic Transistors

Chen, Zhihua; Zheng, Yan; He, Yan; Facchetti, Antonio

doi:10.1021/ja805407g

Cited by 539 publications

(513 citation statements)

References 34 publications

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“…Thin film of reference polymer P(NDI2OD-T2) exhibited two reversible reduction peaks, which were attributed to the formation of radical anion and dianions of NDI in the polymer backbone. 27 All random copolymers showed quasi-reversible reduction peaks with almost similar values of electrochemical reduction like P(NDI2OD-T2). None of the copolymer showed oxidation peak during anodic scan up to 2 V. The lowest occupied molecular orbital (LUMO) energy levels were estimated based on the onset value of first reduction peak and reference energy level of ferrocene (4.8 eV below the vacuum level) according to E LUMO (eV) = −e × (E red onset + 4.8) below the vacuum level.…”

Section: ■ Results and Discussionmentioning

confidence: 93%

“…These values are comparable with literature reports. 27,28 Random copolymers showed lower weight-average molecular weight (M w ) and M w / M n with M w in the range of 32.4−60.7 kDa and PDI in range of 2.5−3.1 (Table 1). Furthermore, the M w and M w /M n were found to decrease as the content of PDI unit increased in the random copolymer.…”

Section: ■ Results and Discussionmentioning

confidence: 99%

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Improved All-Polymer Solar Cell Performance of n-Type Naphthalene Diimide–Bithiophene P(NDI2OD-T2) Copolymer by Incorporation of Perylene Diimide as Coacceptor

et al. 2016

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Naphthalene diimide−bithiophene P(NDI2OD-T2) is a well-known donor−acceptor polymer, previously explored as n-type material in all-polymer solar cells (all-PSCs) and organic field effect transistor (OFETs) applications. The optical, bulk, electrochemical, and semiconducting properties of P(NDI2OD-T2) polymer were tuned via random incorporation of perylene diimide (PDI) as coacceptor with naphthalene diimide (NDI). Three random copolymers containing 2,2′-bithiophene as donor unit and varying compositions of naphthalene diimide (NDI) and perylene diimide (xPDI, x = 15, 30, and 50 mol % of PDI) as two mixed acceptors were synthesized by Stille coupling copolymerization. Proton NMR spectra recorded in CDCl 3 showed that the π−π stacking induced aggregation among the naphthalene units could be successfully disrupted by the random incorporation of bulky PDI units. The newly synthesized random copolymers were investigated as electron acceptors in BHJ all-PSCs, and their performance was compared with P(NDI2OD-T2) as reference polymer. An enhanced PCE of 5.03% was observed for BHJ all-PSCs (all-polymer solar cells) fabricated using NDI-Th-PDI30 as acceptor and PTB7-Th as donor, while the reference polymer blend with the same donor polymer exhibited PCE of 2.97% efficiency under similar conditions. SCLC bulk carrier mobility measured for blend devices showed improved charge mobility compared to reference polymer, with PTB7-Th:NDI-Th-PDI30 blend device exhibiting the high hole and electron mobility of 4.2 × 10 −4 and 1.5 × 10 −4 cm 2 /(V s), respectively. This work demonstrates the importance of molecular design via random copolymer strategy to control the bulk crystallinity, compatibility, blend morphology, and solar cell performance of n-type copolymers.

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Section: ■ Results and Discussionmentioning

confidence: 93%

Section: ■ Results and Discussionmentioning

confidence: 99%

Improved All-Polymer Solar Cell Performance of n-Type Naphthalene Diimide–Bithiophene P(NDI2OD-T2) Copolymer by Incorporation of Perylene Diimide as Coacceptor

et al. 2016

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“…Analogously with previous reports on PNDI2OD-T2, the two distinctive peaks observed can be attributed to a π-π* transition and an intramolecular transition with charge transfer character between the electron-donating unit and the electronacceptor unit, respectively. [63][64][65][66][67] With respect to the analogue NDI copolymer with the thienylene moiety instead of the selenophene, PNDI-SVS UV-vis absorption maxima are 30 nm red shifted owing to the introduction of a slightly stronger electron donor unit. Correspondingly, the optical band gap of PNDI-SVS, estimated at the onset of absorption maxima, is 1.31 eV, slightly narrower than the bandgap of PNDI-TVT.…”

Section: Synthesis and Density Functional Theory Calculationmentioning

confidence: 99%

High‐Mobility Naphthalene Diimide and Selenophene‐Vinylene‐Selenophene‐Based Conjugated Polymer: n‐Channel Organic Field‐Effect Transistors and Structure–Property Relationship

Sung

Luzio

Park

et al. 2016

Adv Funct Materials

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Interdependence of chemical structure, thin-film morphology, and transport properties is a key, yet often elusive aspect characterizing the design and development of high-mobility, solution-processed polymers for large-area and flexible electronics applications. There is a specific need to achieve >1 cm 2 V −1 s −1 field-effect mobilities (μ) at low processing temperatures in combination with environmental stability, especially in the case of electron-transporting polymers, which are still lagging behind hole transporting materials. Here, the synthesis of a naphthalene-diimide based donor-acceptor copolymer characterized by a selenophene vinylene selenophene donor moiety is reported. Optimized field-effect transistors show maximum μ of 2.4 cm 2 V −1 s −1 and promising ambient stability. A very marked film structural evolution is revealed with increasing annealing temperature, with evidence of a remarkable 3D crystallinity above 180 °C. Conversely, transport properties are found to be substantially optimized at 150 °C, with limited gain at higher temperature. This discrepancy is rationalized by the presence of a surface-segregated prevalently edge-on packed polymer phase, dominating the device accumulated channel. This study therefore serves the purpose of presenting a promising, high-electron-mobility copolymer that is processable at relatively low temperatures, and of clearly highlighting the necessity of specifically investigating channel morphology in assessing the structure-property nexus in semiconducting polymer thin films.

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“…19(a)]. 120,121 Although several promising high electron mobility polymers have been synthesized, 122 all-polymer solar cells still lags behind in efficiency.…”

Section: Reviewmentioning

confidence: 99%

On the morphology of polymer‐based photovoltaics

Liu

Jung

et al. 2012

J Polym Sci B Polym Phys

304

242

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We review the morphologies of polymer-based solar cells and the parameters that govern the evolution of the morphologies and describe different approaches to achieve the optimum morphology for a BHJ OPV. While there are some distinct differences, there are also some commonalities. It is evident that morphology and the control of the morphology are important for device performance and, by controlling the thermodynamics, in particular, the interactions of the components, and by controlling kinetic parameters, like the rate of solvent evaporation, crystallization and phase separation, optimized morphologies for a given system can be achieved. While much research has focused on P3HT, it is evident that a clearer understanding of the morphology and the evolution of the morphology in low bad gap polymer systems will increase the efficiency further. While current OPVs are on the verge of breaking the 10% barrier, manipulating and controlling the morphology will still be key for device optimization and, equally important, for the fabrication of these devices in an industrial setting.

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Naphthalenedicarboximide- vs Perylenedicarboximide-Based Copolymers. Synthesis and Semiconducting Properties in Bottom-Gate N-Channel Organic Transistors

Cited by 539 publications

References 34 publications

Improved All-Polymer Solar Cell Performance of n-Type Naphthalene Diimide–Bithiophene P(NDI2OD-T2) Copolymer by Incorporation of Perylene Diimide as Coacceptor

Improved All-Polymer Solar Cell Performance of n-Type Naphthalene Diimide–Bithiophene P(NDI2OD-T2) Copolymer by Incorporation of Perylene Diimide as Coacceptor

High‐Mobility Naphthalene Diimide and Selenophene‐Vinylene‐Selenophene‐Based Conjugated Polymer: n‐Channel Organic Field‐Effect Transistors and Structure–Property Relationship

On the morphology of polymer‐based photovoltaics

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