High mobility organic thin film transistor and efficient photovoltaic devices using versatile donor–acceptor polymer semiconductor by molecular design

Sonar, Prashant; Singh, Samarendra P.; Li, Yuning; Ooi, Zi En; Ha, Tae‐Jun; Wong, O. I.; Soh, Mui Siang; Dodabalapur, Ananth

doi:10.1039/c1ee01213d

Cited by 170 publications

(157 citation statements)

References 31 publications

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“…Of particular interest is the sensitivity of the polaron generation and decay with respect to the applied voltage. For all polymers, the voltage at which ground state bleaching and weak polaron absorption was first observed was 0.6 V. The HOMO values for PDPP-FPF, PDPP-FNF, PDPP-FAF, and PDPP-TNT were reported [30,31] to be very close to one another at 5.40, 5.34, 5.33, and 5.30 eV, respectively. At larger applied voltages, while additional bleaching of ground-state absorption was observed, the polaron signal started to decay, as illustrated by the drop in their corresponding absorption.…”

Section: Spectroeclectrochemistrymentioning

confidence: 84%

“…In this paper we investigate the optical properties of a series of furan substituted diketopyrrolopyrrole co-polymers with phenylene, naphthalene and anthracene co-monomer blocks: poly(3,6-difuran-2-yl-2,5-di(2-octyldodecyl)-pyrrolo [3,4-c]pyrrole-1,4-dione-alt-phenylene) (PDPP-FPF), poly(3,6-difuran-2-yl-2,5-di(2-octyldodecyl)-pyrrolo [3,4-c]pyrrole-1,4-dione-alt-naphthalene) (PDPP-FNF) and poly(3,6-difuran-2-yl-2,5-di(2-octyl dodecyl)-pyrrolo [3,4-c]pyrrole-1,4-dione-alt-anthracene) (PDPP-FAF) [30]. We also investigate a thipohene analogue to PDPP-FNF, Poly(3,6-dithiophene-2-yl-2,5-di(2-octyldodecyl)-pyrrolo [3,4-c] pyrrole-1,4-dione-alt-naphthalene) (PDPP-TNT) [31,32]. The molecular structure for all polymers is shown in Scheme 1.…”

Section: Introductionmentioning

confidence: 99%

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Optical Characterization of the Hole Polaron in a Series of Diketopyrrolopyrrole Polymers Used for Organic Photovoltaics

et al. 2014

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A strategy that is often used for designing low band gap polymers involves the incorporation of electron-rich (donor) and electron-deficient (acceptor) conjugated segments within the polymer backbone. In this paper we investigate such a series of Diketopyrrolopyrrole (DPP)-based co-polymers. The co-polymers consisted of a DPP unit attached to a phenylene, naphthalene, or anthracene unit. Additionally, polymers utilizing either the thiophene-flanked DPP or the furan-flanked DPP units paired with the naphthalene comonomer were compared. As these polymers have been used as donor materials and subsequent hole transporting materials in organic solar cells, we are specifically interested in characterizing the optical absorption of the hole polaron of these DPP based copolymers. We employ chemical doping, electrochemical doping, and photoinduced OPEN ACCESSPolymers 2015, 7 70 absorption (PIA) studies to probe the hole polaron absorption spectra. While some donor-acceptor polymers have shown an appreciable capacity to generate free charge carriers upon photoexcitation, no polaron signal was observed in the PIA spectrum of the polymers in this study. The relations between molecular structure and optical properties are discussed.

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Section: Spectroeclectrochemistrymentioning

confidence: 84%

Section: Introductionmentioning

confidence: 99%

Optical Characterization of the Hole Polaron in a Series of Diketopyrrolopyrrole Polymers Used for Organic Photovoltaics

et al. 2014

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“…The HOMO level and E g ec of PDPP-TNT were reported to be −5.29 and 1.99 eV, respectively. 6 These results indicate that our PDPP-TDNT has a larger E g ec but a deeper HOMO level compared to the reported PDPP-TNT. It has been reported that electron-releasing substituents such as alkoxy groups on electron-donor units can tuned the HOMO level of the resulting conjugated polymers.…”

Section: Resultsmentioning

confidence: 45%

“…On the other hand, the absorption pattern of PDPP-TNT was reported to be reversed from PDPP-TDNT, which absorbed much more intensely at 500-800 nm than at 300-500 nm. 6 The absorption in the longer wavelength region can be attributed to intermolecular charge transfer between the electron-rich and electron-poor units in the polymer chain. This comparison suggests that the low absorption intensity of PDPP-TDNT in the longer wavelength region may result from less efficient charge transfer between the DNT and DPP moieties through the thiophene spacer due to the bulky alkoxy substituents on the naphthalene ring.…”

Section: Resultsmentioning

confidence: 99%

Alternating Copolymers Consisting of Dialkoxylated Naphthalene along with Either Dithiophenylated 1,4-Dioxopyrrolo-[3,4c]-pyrrole or 5H-thieno[3,4-c]pyrrole-4,6-dione: Synthesis and Photo-Electrochemical Properties

Lim¹,

Yang²,

Kim³

et al. 2013

Bulletin of the Korean Chemical Society

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Recently, research has rapidly progressed on the development of bulk heterojunction polymer solar cells that use low band-gap polymers (p-type semiconducting polymers or electron donors) blended with (6,6)-phenyl-butyric acid methyl ester (PCBM, a n-type organic molecule or an electron acceptor) in the active layers, and their power conversion efficiency (PCE) has been increased over 8%.1 One approach to further improve the performance of polymer solar cells is through the use of new conjugated polymers with ideal properties such as low band-gap, high charge mobility, and appropriate energy levels of the highest/lowest molecular orbital (HOMO/LUMO).Low band-gap polymers have been developed which allow polymer solar cells to harvest more sunlight. Low band-gap polymers for use in solar cells have been synthesized from many different types of electron-rich and electron-poor monomers.2 One strategy for obtaining low bandgap polymers is to synthesize alternating copolymers by combining appropriate electron-rich monomers with electron-poor monomers (so-called "push-pull" architecture).The charge mobility of active layers in polymer solar cells has been increased using various methods such as thermal annealing 2b and the use of additives. The energy difference between the HOMO level of the p-type polymer and the LUMO level of PCBM is closely related to the open-circuit voltage (V oc ) of a solar cell, which increases as the HOMO/ LUMO difference increases. Thus, p-type conjugated polymers with low (or deep) HOMO levels are preferred. The energy levels of the HOMO/LUMO of p-type polymers can be tuned by combining appropriate electron-rich monomers with electron-poor monomers.Dialkoxynaphthalene (DN) is planar and can form intermolecular π-π stacks, leading to high charge mobility.3 Alternating polymers based on DN that contain benzodithiadiazole, thiazolothiazole, bithiophene, and (Z)-2,3-di(thiophen-2-yl)acrylonitrile units have been used to fabricate solar cells. The PCEs of solar cells fabricated using these p-type polymers were in the range of 0.06-2.90%. Diketopyrrolo [3,4-c]pyrrole (DPP) is a strong electron acceptor that can lower the HOMO level. Some DPP-containing conjugated polymers exhibited high hole mobilities, up to 2 × 10 −3 cm 2 / V·s, and PCEs up to 6.5%.4 Thieno [3,4-c]pyrrole-4,6-dione (TPD) is also a strong electron acceptor, and some TPDcontaining conjugated polymers were reported to have deep HOMO levels, leading to a high V oc and the highest reported PCE of 7.30%. 5A DPP-naphthalene polymer (PDPP-TNT) with a thiophene spacer between the DPP and naphthalene units has been reported to have a PCE of 4.7%.6 A DPP-containing polymer analog (PDPP-TDNT) is also interesting since alkoxy substituents can tune the HOMO/LUMO levels by increasing the electron-donating properties of the naphthalene moiety.

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“…20 The introduction of 23 Although the crystallinity of the T-DPP-T based polymer was improved due to the rigidity of the arylenevinylene linkage, this did not change the hole mobility (measured at 0.2 cm 2 /Vs). In order to increase the overall planarity of the conjugated backbone, two fused aromatic systems, naphthalene (P15) 24 and…”

Section: Discussionmentioning

confidence: 99%

Recent advances in high mobility donor–acceptor semiconducting polymers

et al. 2012

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A combination of improved understanding of molecular design criteria and polymer purification techniques, as well as optimised fabrication techniques and device surface treatments, have driven recent advances in the performance of semiconducting polymers for transistor applications. This development has allowed polymer-based devices to reach parity with the best values obtained for small molecule evaporated devices. Herein, we present the most recent work on solution processable high mobility donor-acceptor type polymers. We discuss the approaches that have been taken to improve both hole (and electron) mobility further. We will not only focus on chemical design criteria, but also describe certain processing approaches which have led to impressive hole mobilities of up to 5.5 cm 2 /Vs.

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High mobility organic thin film transistor and efficient photovoltaic devices using versatile donor–acceptor polymer semiconductor by molecular design

Cited by 170 publications

References 31 publications

Optical Characterization of the Hole Polaron in a Series of Diketopyrrolopyrrole Polymers Used for Organic Photovoltaics

Optical Characterization of the Hole Polaron in a Series of Diketopyrrolopyrrole Polymers Used for Organic Photovoltaics

Alternating Copolymers Consisting of Dialkoxylated Naphthalene along with Either Dithiophenylated 1,4-Dioxopyrrolo-[3,4c]-pyrrole or 5H-thieno[3,4-c]pyrrole-4,6-dione: Synthesis and Photo-Electrochemical Properties

Recent advances in high mobility donor–acceptor semiconducting polymers

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