D–A copolymer with high ambipolar mobilities based on dithienothiophene and diketopyrrolopyrrole for polymer solar cells and organic field-effect transistors

Kim, In-Bok; Khim, Dongyoon; Jang, Soo‐Young; Kim, Jihong; Yu, Byung-Kwan; Kim, Yeong-A; Kim, Dong‐Yu

doi:10.1016/j.orgel.2015.07.003

Cited by 20 publications

(8 citation statements)

References 55 publications

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“…Such mobility values for holes and electrons are in the medium-high range when compared to the mobilities observed in other, nonambipolar columnar phases. The same can be said when considering the mobilities measured in other ambipolar smectic phases or phases obtained by using donor–acceptor dyads, polymers, − or even solid solutions . Particularly for triphenylene materials, hole mobility values have been reported in the range of 10 –4 –10 –1 cm 2 V –1 s –1 . ,− In a few cases, electron mobilities have been measured, obtaining values as fast as for hole mobility, in the range of 10 –3 –10 –1 cm 2 V –1 s –1 by the TOF method .…”

Section: Results and Discussionmentioning

confidence: 94%

H-Bonded Donor–Acceptor Units Segregated in Coaxial Columnar Assemblies: Toward High Mobility Ambipolar Organic Semiconductors

et al. 2016

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A novel approach to ambipolar semiconductors based on hydrogen-bonded complexes between a star-shaped tris(triazolyl)triazine and triphenylene-containing benzoic acids is described. The formation of 1:3 supramolecular complexes was evidenced by different techniques. Mesogenic driving forces played a decisive role in the formation of the hydrogen-bonded complexes in the bulk. All of the complexes formed by nonmesogenic components gave rise to hexagonal columnar (Colh) liquid crystal phases, which are stable at room temperature. In all cases, X-ray diffraction experiments supported by electron density distribution maps confirmed triphenylene/tris(triazolyl)triazine segregation into hexagonal sublattices and lattices, respectively, as well as remarkable intracolumnar order. These highly ordered nanostructures, obtained by the combined supramolecular H-bond/columnar liquid crystal approach, yielded donor/acceptor coaxial organization that is promising for the formation of ambipolar organic semiconductors with high mobilities, as indicated by charge transport measurements.

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Section: Results and Discussionmentioning

confidence: 94%

H-Bonded Donor–Acceptor Units Segregated in Coaxial Columnar Assemblies: Toward High Mobility Ambipolar Organic Semiconductors

et al. 2016

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“…All chemicals were purchased from Aldrich, TCI, Alfa Aesar, Acros, or Strem Chemicals and used without further purification. All the monomers were synthesized according to the previously published literature. ,,, All air- and water-sensitive reactions were conducted under a nitrogen atmosphere. Tetrahydrofuran (THF) was distilled from sodium and benzophenone.…”

Section: Methodsmentioning

confidence: 99%

“…1 H NMR spectra analyses, thermal gravity analyses, scanning calorimetry analyses, cyclic voltammetry measurements, and absorption spectra were conducted according to the previous literatures . Elemental analysis was checked on an EA1112 instrument (CE Instrument).…”

Section: Methodsmentioning

confidence: 99%

“…Several methods have been attempted in order to obtain D-A polymers with high PCEs, including introducing fused heterocycles as a monomer unit or attaching various substituents on their conjugated backbones. − The substitution of fluorine (F) atoms on the conjugated backbones, in particular, has recently shown remarkable results in PSCs arising from their ability of efficient charge transport and proper formation of nanoscale morphology with fullerene derivatives with the aid of solvent additives, such as 1,8-diiodooctane (DIO) or 1-chloronaphthalene (CN). − A F atom itself has a small size with a van der Waals radius of 1.35 Å, also the most electronegative property of all the elements with a Pauling electronegativity of 4.0. Such a small size of the F atom enables a greater planarity of the polymer backbones and consequently promotes efficient charge transport, compared with when they are substituted with other atoms. ,,, An enormous electronegativity value of 4.0 means that the F atom would effectively withdraw the electron density of a conjugated system, therefore, stabilize the highest occupied molecular orbital (HOMO) and the lowest unoccupied molecular orbital (LUMO), facilitating an enhanced open circuit voltage ( V OC ) without introducing steric hindrance along the polymer chains.…”

Section: Introductionmentioning

confidence: 99%

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The Effect of Fluorine Substitution on the Molecular Interactions and Performance in Polymer Solar Cells

Kim

Jang

Kim

et al. 2017

ACS Appl. Mater. Interfaces

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Fluorine (F) substitution on conjugated polymers in polymer solar cells (PSCs) has a diverse effect on molecular properties and device performance. We present a series of three D-A type conjugated polymers (PBT, PFBT, and PDFBT) based on dithienothiophene and benzothiadiazole units with different numbers of F atoms to explain the influence of F substitution by comparing the molecular interactions of the polymers and the recombination kinetics in PSCs. The preaggregation behavior of PFBT and PDFBT in o-DCB at the UV-vis absorption spectra proves that both polymers have strong intermolecular interactions. Besides, more closely packed structures and change into face-on orientation of fluorinated polymers are observed in polymer:PCBM blends by GIXD which is beneficial for charge transport and, ultimately, for current density in PSCs (4.3, 13.0, and 14.5 mA cm for PBT, PFBT, and PDFBT, respectively). Also, the introduction of F atoms on conjugated backbones affects the recombination kinetics by suppressing bimolecular recombination, thereby improving the fill factor (0.41, 0.68, and 0.69 for PBT, PFBT, and PDFBT, respectively). Consequently, the PCE of PSCs reached 7.3% without any additional treatment (annealing, solvent additive, etc.) in the polymer containing difluorinated BT (PDFBT) that is much higher than nonfluorinated BT (PBT ∼ 1%) and monofluorinated BT (PFBT ∼ 6%).

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“…However, polymer-polymer or polymer-fullerene blends have yielded limited performances values of ≈10 −3 cm 2 V −1 s −1 for both hole and electron, presumably due to a lack of interpenetrating and bicontinuous networks in such fabricated fi lms. [ 13 ] Realizing ideal and homogeneous morphologies in polymerpolymer blends with obviously different surface energies, therefore, remains a challenge.…”

Section: Introductionmentioning

confidence: 99%

Facile and Fine Polarity‐Tuning of Polymeric Semiconductors: The Effects of Nitrile Groups on Polymer–Polymer Blend Systems

Cho

Lee²,

Lee

et al. 2016

Adv Elect Materials

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Currently, the majority of high performance ambipolar polymer fi eld effect transistors rely on the synthesis of donor-acceptor conjugated polymers with balanced hole/electron mobilities, whose polarity is predetermined during synthesis. However, further tuning of the device polarity is necessary in many applications, and a facile and fi ne polarity tuning with additional fabrication steps is necessary. To solve these issues, the utilization of polymer-polymer blends is recommended in which the electronic confi guration and charge transport characteristics can be fi nely rationalized. A polymer-polymer blend system consisting of two different donor-acceptor polymeric semiconductors, namely PDPPTVT and PDPPCNTVT, is introduced with nearly identical chemical structures apart from the presence of a nitrile group. The nitrile group in PDPPCNTVT creates some important differences in terms of molecular orientation and surface energy in comparison to PDPPTVT. However, because of the chemical similarity, blend fi lms consisting of these two polymers show outstanding homogeneous morphologies, enabling a facile and fi ne polarity tuning to be realized simply by changing the mixture ratio. A 1:1 blend ratio between PDPPTVT with hole mobility of ≈1 cm 2 V −1 s −1 and PDPPCNTVT with electron mobility of ≈1 cm 2 V −1 s −1 enables an almost balanced charge carrier mobility of ≈0.5 cm 2 V −1 s −1 for both holes and electrons.

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D–A copolymer with high ambipolar mobilities based on dithienothiophene and diketopyrrolopyrrole for polymer solar cells and organic field-effect transistors

Cited by 20 publications

References 55 publications

H-Bonded Donor–Acceptor Units Segregated in Coaxial Columnar Assemblies: Toward High Mobility Ambipolar Organic Semiconductors

H-Bonded Donor–Acceptor Units Segregated in Coaxial Columnar Assemblies: Toward High Mobility Ambipolar Organic Semiconductors

The Effect of Fluorine Substitution on the Molecular Interactions and Performance in Polymer Solar Cells

Facile and Fine Polarity‐Tuning of Polymeric Semiconductors: The Effects of Nitrile Groups on Polymer–Polymer Blend Systems

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