Reduced roughness for improved mobility in benzodipyrrolidone-based, n-type OFETS

Rumer, Joseph W.; Rossbauer, Stephan; Planells, Miquel; Watkins, Scott E.; Anthopoulos, Thomas D.; McCulloch, Iain

doi:10.1039/c4tc01790k

Cited by 25 publications

(17 citation statements)

References 35 publications

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“…The TVT units have already been known to be useful for constructing planar D–A polymer, because the vinylene unit is less likely to be twisted and energetically favors a 2D conformation. Interestingly, although the BT unit contains a single bond, the CC bond between the two thiophene rings of bithiophene is not remarkably twisted and the overall planarity of PIIG–BT was found to be similar to PIIG–TVT. Both of the polymers had a small dihedral angle (9.9°–13.8°) at the D–A bond and an even smaller torsion angle (0.2°–2.2°) inside the donor units.…”

Section: Resultsmentioning

confidence: 99%

Effect of Donor Molecular Structure and Gate Dielectric on Charge‐Transporting Characteristics for Isoindigo‐Based Donor–Acceptor Conjugated Polymers

Park

Kim

Yang

et al. 2016

Adv Funct Materials

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with CYTOP dielectric though the BT units have less planarity than the TVT and Np units. The reasons for the different mobility in IIG-based polymers are studied by analyzing the energy structure by absorption spectra, calculating transport levels by density functional theory, investigating the in-and out-of-plane crystallinity of thin film by grazing-incidence wideangle X-ray scattering, and extracting key transport parameters via lowtemperature measurements. By combining theoretical, optical, electrical, and structural analyses, this study finds that the large difference in OFET mobility mainly originates from the transport disorders determined by the different microcrystal structure, rather than the intrinsic transport properties in isolated chains for different polymers. bithiophene (BT), and thiophene-vinylene-thiophene (TVT). These three groups are selected because they are of the similar size and thus should give similar contribution to electron density to the semiconducting polymers, simplifying the comparative study. In addition, these groups have been widely adapted in synthesizing D-A semiconducting polymers. PIIG-Np, PIIG-BT, and PIIG-TVT polymers were synthesized by Pd-catalyzed Suzuki (PIIG-Np) and Stille (PIIG-BT and PIIG-TVT) cross-coupling according to the literature [5a,6,8] and applied in the active layer of top-gate and bottom-contact (TG/BC) OFETs with poly(methyl methacrylate) (PMMA) or CYTOP as a gate dielectric layer.All OFETs showed stable p-type transistor characteristics, but a huge mobility difference was observed among polymers with different donor units. Though the BT unit has less planarity than the Np and TVT units and is not considered the best partner for charge transport, PIIG-BT OFETs showed 50 times higher hole mobility (0.63 cm 2 V −1 s −1 ) than PIIG-TVT and PIIG-Np ones of ≈ 0.01 cm 2 V −1 s −1 (with CYTOP dielectric). The reasons for the structure-property relationship are studied here by a combination of various analyses: (i) Analyzing energy structure by absorption spectra; (ii) calculating transport levels by density functional theory (DFT); (iii) investigating the inand out-of-plane crystallinity of thin film by grazing-incidence wide-angle X-ray scattering (GIWAXS); and (iv) extracting key transport parameters via low-temperature measurements. The large difference in OFET mobility mainly originates from the transport disorders determined by the different microcrystal structure, rather than the intrinsic transport properties in isolated chains for different polymers. In particular, PIIG-BT polymer exhibits a special crystal structure and the highest crystalline degree, which apparently benefits the charge transport occurring in both in-plane and out-of-plane directions.

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Section: Resultsmentioning

confidence: 99%

Effect of Donor Molecular Structure and Gate Dielectric on Charge‐Transporting Characteristics for Isoindigo‐Based Donor–Acceptor Conjugated Polymers

Park

Kim

Yang

et al. 2016

Adv Funct Materials

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“…McCulloch’s group reported a series of isoDPP-polymers (P22–26, Figure 6) [75]. The UV/vis absorption maxima of all polymers in thin film located between 620 and 650 nm except P25 and P26 being of 687 and 554 nm, respectively.…”

Section: Polymersmentioning

confidence: 99%

Conjugated Polymers Containing Building Blocks 1,3,4,6-Tetraarylpyrrolo[3,2-b]pyrrole-2,5-dione (isoDPP), Benzodipyrrolidone (BDP) or Naphthodipyrrolidone (NDP): A Review

Deng

et al. 2019

Polymers

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π-Conjugated organic donor–acceptor (D–A) type polymers are widely developed and used in electronic device. Among which, diketopyrrolopyrrole (DPP)-based polymers have received the most attention due to their high performances. The novel chromophores named 1,3,4,6-tetraarylpyrrolo[3,2-b]pyrrole-2,5-dione (isoDPP), benzodipyrrolidone (BDP) and naphthodipyrrolidone (NDP) are resemble DPP in chemical structure. IsoDPP is an isomer of DPP, with the switching position of carbonyl and amide units. The cores of BDP and NDP are tri- and tetracyclic, whereas isoDPP is bicyclic. π-Conjugation extension could result polymers with distinct optical, electrochemical and device performance. It is expected that the polymers containing these high-performance electron-deficient pigments are potential in the electronic device applications, and have the potential to be better than the DPP-based ones. IsoDPP, BDP, and NDP based polymers are synthesized since 2011, and have not receive desirable attention. In this work, the synthesis, properties (optical and electrochemical characteristics), electronic device as well as their relationship depending on core-extension or structure subtle optimization have been reviewed. The final goal is to outline a theoretical scaffold for the design the D–A type conjugated polymers, which is potential for high-performance electronic devices.

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“…The charge carrier mobility of polymers with trans -vinylene and thiophene-derived repeating units ( trans -poly(thienylenevinylene)s; PTVs) has been reported to be the highest among π-conjugated polymers. − However, trans -PTVs have strong interchain π–π interactions due to their planar structure, which limits their solubility. , The more twisted configuration of the cis -vinylene units tends to result in less optimized interchain stacking and thus higher solubility . We have demonstrated that thin films of cis -poly( p -phenylenevinylene)s undergo cis-to-trans isomerization under UV irradiation (Figure e). − A similar isomerization of cis -vinylene may provide a direct and efficient route to the fabrication of trans -PTVs thin films (Figure f).…”

Section: Introductionmentioning

confidence: 98%

“…16−22 However, trans-PTVs have strong interchain π−π interactions due to their planar structure, which limits their solubility. 20,21 The more twisted configuration of the cis-vinylene units tends to result in less optimized interchain stacking and thus higher solubility. 23 We have demonstrated that thin films of cis-poly(pphenylenevinylene)s undergo cis-to-trans isomerization under UV irradiation (Figure 1e).…”

Section: ■ Introductionmentioning

confidence: 99%

Formation of trans-Poly(thienylenevinylene) Thin Films by Solid-State Thermal Isomerization

et al. 2021

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e r i z a t i o n o f p o l y -(thienylenevinylene) is found to be a viable fabrication method for semiconducting trans-poly(thienylenevinylene) (trans-P1) thin films. Specifically, thin films of trans-P1, an alternating copolymer containing isoindigo and (E)-1,2-dithienylethene units, which are well known as an excellent p-type semiconductor, were prepared by thermally annealing thin films of the cis-poly(thienylenevinylene) (cis-P1) isomer (92% cis) at 240 °C for 30 min. The hole mobility of the isomerized films is comparable to that of films prepared from spin-coated solutions of the trans-isomer. Taking advantage of the greater solubility of the cis-isomer, it was possible to replace the toxic halogenated solvents normally needed for the dissolution of trans-P1 with the environmentally friendly 2-MeTHF. Solid-state cis-to-trans isomerization is therefore a potentially attractive fabrication option for the commercial development of sustainable, printable electronics.

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Reduced roughness for improved mobility in benzodipyrrolidone-based, n-type OFETS

Cited by 25 publications

References 35 publications

Effect of Donor Molecular Structure and Gate Dielectric on Charge‐Transporting Characteristics for Isoindigo‐Based Donor–Acceptor Conjugated Polymers

Effect of Donor Molecular Structure and Gate Dielectric on Charge‐Transporting Characteristics for Isoindigo‐Based Donor–Acceptor Conjugated Polymers

Conjugated Polymers Containing Building Blocks 1,3,4,6-Tetraarylpyrrolo[3,2-b]pyrrole-2,5-dione (isoDPP), Benzodipyrrolidone (BDP) or Naphthodipyrrolidone (NDP): A Review

Formation of trans-Poly(thienylenevinylene) Thin Films by Solid-State Thermal Isomerization

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