Synthesis and characterization of solution-processable diketopyrrolopyrrole (DPP) and tetrathienothiophene (TTA)-based small molecules for organic thin film transistors and organic photovoltaic cells

Vegiraju, Sureshraju; Hsieh, Cheng Ming; Huang, Deng Yi; Chen, Yen Chia; Priyanka, Pragya; Ni, Jen‐Shyang; Esya, Firdausy Amalina; Kim, Choongik; Yau, Shueh Lin; Chen, Chih‐Ping; Chen, Ming Chou

doi:10.1016/j.dyepig.2016.05.041

Cited by 29 publications

(10 citation statements)

References 57 publications

(42 reference statements)

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“…When extending π‐conjugation by inserting thiophene rings between DPP and TTA it produces compounds 63 and 64 , which decrease the mobilities to 0.02 and 4.5 × 10 −4 cm 2 V −1 s −1 , respectively. [ 50 ] Compound 65 with a TTA core is connected with O ‐alkylated DPP moiety, which yields a mobility 0.018 cm 2 V −1 s −1 after annealing at 110 °C. [ 49 ] Compound 66 shows similar device performance to that of 63.…”

Section: Tetrathienoacene (Tta)‐based Small Molecular Semiconductor F...mentioning

confidence: 99%

“…[ 49 ] Compound 66 shows similar device performance to that of 63. [ 50 ] Apart from OSCs, the TTA core has also been exploited as a π‐bridge unit in the organic sensitizer with the molecular architecture of donor‐π‐bridge‐acceptor (D‐π‐A) for high performance DSSCs, [ 51 ] vide infra.…”

Section: Tetrathienoacene (Tta)‐based Small Molecular Semiconductor F...mentioning

confidence: 99%

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Fused thiophene based materials for organic thin‐film transistors

Velusamy

Afraj

Yau

et al. 2022

J Chinese Chemical Soc

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Section: Tetrathienoacene (Tta)‐based Small Molecular Semiconductor F...mentioning

confidence: 99%

Section: Tetrathienoacene (Tta)‐based Small Molecular Semiconductor F...mentioning

confidence: 99%

Fused thiophene based materials for organic thin‐film transistors

Velusamy

Afraj

Yau

et al. 2022

J Chinese Chemical Soc

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“…As a result, these small molecular materials showed broad and strong absorptions, low-lying HOMO energy levels, high hole mobilities, and desirable molecular stacking mode. These features have contributed to create highly efficient small molecular system and to understand the relationships of structure-device performance. − Currently, the popular strategy for high efficient small molecular donor was based on oligothiophene/benzodithiophene (BDT) or other electron-rich units as core and capped with relatively electron-withdrawing units, which was called as “A-D-A” sequence system. Chen and other groups did outstanding research work in A-D-A sequenced small molecules with the PCEs of over 10%. − Recently, D-A-D-A-D sequenced small molecules, that can be viewed as modified A-D-A sequenced small molecules by further end-capping of donor terminal units, have attracted much attention.…”

Section: Introductionmentioning

confidence: 99%

Applying Thienyl Side Chains and Different π-Bridge to Aromatic Side-Chain Substituted Indacenodithiophene-Based Small Molecule Donors for High-Performance Organic Solar Cells

Wang

Liu

et al. 2017

ACS Appl. Mater. Interfaces

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A pair of linear tetrafluorinated small molecular donors, named as ThIDTTh4F and ThIDTSe4F, which are with tetrathienyl-substituted IDT as electron-rich central core, electron-deficient difluorobenzothiadiazole as acceptor units, and donor end-capping groups, but having differences in the π-bridge (thiophene and selenophene), were successfully synthesized and evaluated as donor materials in organic solar cells. Such π-bridge and core units in these small molecules play a decisive role in the formation of the nanoscale separation of the blend films, which were systematically investigated through absorption spectra, grazing incidence X-ray diffraction pattern, transmission electron microscopy images, resonant soft X-ray scattering profiles, and charge mobility measurement. The ThIDTSe4F (with selenophene π-bridge)-based device exhibited superior performance than devices based on ThIDTh4F (with thiophene π-bridge) after post annealing treatment owing to optimized film morphology and improved charge transport. Power conversion efficiency of 7.31% and fill factor of ∼0.70 were obtained by using a blend of ThIDTSe4F and PC 71 BM with thermal annealing and solvent vapor annealing treatments, which is the highest PCE from aromatic side-chain substituted IDT-based small molecular solar cells. The scope of this study is to reveal the structure–property relationship of the aromatic side-chain substituted IDT-based donor materials as a function of π-bridge and the post annealing conditions.

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“…π-Conjugated polymers comprising electron accepting (A) and electron donating (D) units are widely investigated as semiconductors in organic electronic devices such as organic thin-film transistors (OTFTs) and polymer solar cells (PSCs). − The development of these new polymers relies on the creative design and synthesis of novel A/D building blocks combined with achieving desired structural and physical properties of the polymers such as backbone planarity, considerable π-conjugation, and solid-state chain interactions, as well as sufficient solubility for solution processing. − Furthermore, enabling physical properties specific to a particular device function is required . For instance, for OTFT applications, molecular orbital energies must be compatible with efficient charge injection from the contacts and stable charge transport.…”

Section: Introductionmentioning

confidence: 99%

New Benzo[1,2-d:4,5-d′]bis([1,2,3]thiadiazole) (iso-BBT)-Based Polymers for Application in Transistors and Solar Cells

et al. 2019

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In this paper we report the rationale and implementation of a new building block for organic electronics based on 4,8-di(2-thienyl)-benzo[1,2-d:4,5-d′]bis([1,2,3]thiadiazole) (iso-BBT-T2) and realization of two alkyl-functionalized iso-BBT-tetrathiophene (T4) alternating copolymers (P1 with alkyl = 2DT and P2 with alkyl = 2DH). Compared to the previously investigated small molecules/polymers based on the conventional 4,8-di(2-thienyl)-benzo[l,2-c:4,5-c′]bis[ l,2,5]thiadiazole (BBT-T2), the use of the iso-BBT heterocycle widens the polymer band gap to a region (∼1.4 eV) compatible for use in single junction solar cells. The influence of iso-BBT vs BBT structural variation on the molecular structure, electronic characteristics, and optical properties was accessed by DFT computations, single-crystal determination, optical absorption, and electrochemical measurements. In-plane charge transport for P1 and P2 was investigated in an organic thin-film transistor (OTFT) structure demonstrating hole mobilities approaching 1 cm2 V–1 s–1 and further enhanced by off-center spin-coating method to 1.32 cm2 V–1 s–1. Using PC61BM as acceptor, a remarkable PCE of 10.28% was achieved for P1 along with a current density > 20 mA/cm2. The substantial PCEs of these devices, despite the relatively narrow donor energy gap, is due to retention of high open circuit voltages ( V oc > 0.8 V) as the result of the small energy loss (E loss < 0.6 eV). Atomic force microscopy, transmission electron microscopy, and X-ray diffraction characterization further support the solar cell trends and rationalize structure–property correlations. These results demonstrate that iso-BBT-T2-based polymers are promising candidates for both organic electronics and photonic applications.

show abstract

Synthesis and characterization of solution-processable diketopyrrolopyrrole (DPP) and tetrathienothiophene (TTA)-based small molecules for organic thin film transistors and organic photovoltaic cells

Cited by 29 publications

References 57 publications

Fused thiophene based materials for organic thin‐film transistors

Fused thiophene based materials for organic thin‐film transistors

Applying Thienyl Side Chains and Different π-Bridge to Aromatic Side-Chain Substituted Indacenodithiophene-Based Small Molecule Donors for High-Performance Organic Solar Cells

New Benzo[1,2-d:4,5-d′]bis([1,2,3]thiadiazole) (iso-BBT)-Based Polymers for Application in Transistors and Solar Cells

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