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Isoindigo-Based Small Molecules with Varied Donor Components for Solution-Processable Organic Field Effect Transistor Devices.

ABSTRACT: Two solution-processable small organic molecules, (E)-6,6'-bis(4-(diphenylamino)phenyl)-1,1'-bis(2-ethylhexyl)-(3,3'-biindolinylidene)-2,2'-dione (coded as S10) and (E)-6,6'-di(9H-carbazol-9-yl)-1,1'-bis(2-ethylhexyl)-(3,3'-biindolinylidene)-2,2'-dione (coded as S11) were successfully designed, synthesized and fully characterized. S10 and S11 are based on a donor-acceptor-donor structural motif and contain a common electron accepting moiety, isoindigo, along with different electron donating functionalities, triphenylamine and carbazole, respectively. Ultraviolet-visible absorption spectra revealed that the use of triphenylamine donor functionality resulted in an enhanced intramolecular charge transfer transition and reduction of optical band gap, when compared with its carbazole analogue. Both of these materials were designed to be donor semiconducting components, exerted excellent solubility in common organic solvents, showed excellent thermal stability, and their promising optoelectronic properties encouraged us to scrutinize charge-carrier mobilities using solution-processable organic field effect transistors. Hole mobilities of the order of 2.2 × 10(-4) cm²/Vs and 7.8 × 10(-3) cm²/Vs were measured using S10 and S11 as active materials, respectively.

SUBMITTER: Patil H

PROVIDER: S-EPMC6332248 | biostudies-literature | 2015 Sep

REPOSITORIES: biostudies-literature

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Isoindigo-Based Small Molecules with Varied Donor Components for Solution-Processable Organic Field Effect Transistor Devices.

Patil Hemlata H Chang Jingjing J Gupta Akhil A Bilic Ante A Wu Jishan J Sonar Prashant P Bhosale Sheshanath V SV

Molecules (Basel, Switzerland) 20150918 9

Two solution-processable small organic molecules, (E)-6,6'-bis(4-(diphenylamino)phenyl)-1,1'-bis(2-ethylhexyl)-(3,3'-biindolinylidene)-2,2'-dione (coded as S10) and (E)-6,6'-di(9H-carbazol-9-yl)-1,1'-bis(2-ethylhexyl)-(3,3'-biindolinylidene)-2,2'-dione (coded as S11) were successfully designed, synthesized and fully characterized. S10 and S11 are based on a donor-acceptor-donor structural motif and contain a common electron accepting moiety, isoindigo, along with different electron donating func ...[more]

PMID: 26393566

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Project description:The development of solution-processable n-type molecular semiconductors that exhibit high electron mobility (μe ≥ 0.5 cm2/(V·s)) under ambient conditions, along with high current modulation (Ion/Ioff ≥ 106-107) and near-zero turn on voltage (Von) characteristics, has lagged behind that of other semiconductors in organic field-effect transistors (OFETs). Here, we report the design, synthesis, physicochemical and optoelectronic characterizations, and OFET performances of a library of solution-processable, low-LUMO (-4.20 eV) 2,2'-(2,8-bis(3-alkylthiophen-2-yl)indeno[1,2-b]fluorene-6,12-diylidene)dimalononitrile small molecules, β,β'-Cn-TIFDMTs, having varied alkyl chain lengths (n = 8, 12, 16). An intriguing correlation is identified between the solid-isotropic liquid transition enthalpies and the solubilities, indicating that cohesive energetics, which are tuned by alkyl chains, play a pivotal role in determining solubility. The semiconductors were spin-coated under ambient conditions on densely packed (grafting densities of 0.19-0.45 chains/nm2) ultrathin (∼3.6-6.6 nm) polystyrene-brush surfaces. It is demonstrated that, on this polymer interlayer, thermally induced dispersive interactions occurring over a large number of methylene units between flexible alkyl chains (i.e., zipper effect) are critical to achieve a favorable thin-film crystallization with a proper microstructure and morphology for efficient charge transport. While C8 and C16 chains show a minimal zipper effect upon thermal annealing, C12 chains undergo an extended interdigitation involving ∼6 methylene units. This results in the formation of large crystallites having lamellar stacking ((100) coherence length ∼30 nm) in the out-of-plane direction and highly favorable in-plane π-interactions in a slipped-stacked arrangement. Uninterrupted microstructural integrity (i.e., no face-on (010)-oriented crystallites) was found to be critical to achieving high mobilities. The excellent crystallinity of the C12-substituted semiconductor thin film was also evident in the observed crystal lattice vibrations (phonons) at 58 cm-1 in low-frequency Raman scattering. Two-dimensional micrometer-sized (∼1-3 μm), sharp-edged plate-like grains lying parallel with the substrate plane were observed. OFETs fabricated by the current small molecules showed excellent n-channel behavior in ambient with μe values reaching ∼0.9 cm2/(V·s), Ion/Ioff ∼ 107-108, and Von ≈ 0 V. Our study not only demonstrates one of the highest performing n-channel OFET devices reported under ambient conditions via solution processing but also elucidates significant relationships among chemical structures, molecular properties, self-assembly from solution into a thin film, and semiconducting thin-film properties. The design rationales presented herein may open up new avenues for the development of high-electron-mobility novel electron-deficient indenofluorene and short-axis substituted donor-acceptor π-architectures via alkyl chain engineering and interface engineering.

Dataset Information

Isoindigo-Based Small Molecules with Varied Donor Components for Solution-Processable Organic Field Effect Transistor Devices.

Publications

Isoindigo-Based Small Molecules with Varied Donor Components for Solution-Processable Organic Field Effect Transistor Devices.

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