Donor-acceptor-structured naphtodithiophene-based copolymers for organic thin-film transistors

Kim, Myeong‐Jong; Lee, Ye-Seul; Shin, Sung Chul; Kim, Yun‐Hi

doi:10.1002/pola.27803

Cited by 6 publications

(4 citation statements)

References 37 publications

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“…The introduction of F atoms is expected to get the high crystallinity and a planar backbone because of intramolecular F-S interactions, as well as deep HOMO energy levels, thus leading to high J SC and V OC . [20][21][22][23][24][25] The acceptor units were benzothiadiazole (BT) derivatives with and without F atoms. [26][27][28][29] The synthesis and characteristics of donor moiety with F substituents and polymers are reported.…”

Section: Introductionmentioning

confidence: 99%

“…Therefore, a new set of IDID donor unit with F substituents was synthesized for organic electronic applications. The introduction of F atoms is expected to get the high crystallinity and a planar backbone because of intramolecular F‐S interactions, as well as deep HOMO energy levels, thus leading to high J SC and V OC 20‐25 . The acceptor units were benzothiadiazole (BT) derivatives with and without F atoms 26‐29 .…”

Section: Introductionmentioning

confidence: 99%

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New 3, 8‐difluoro indoloindole‐based copolymers for organic solar cell

et al. 2021

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The performance of an array of donor-acceptor based bulk heterojunction (BHJ) polymer solar cells (PSC) containing indoloindole as a key donor block with varying degrees of fluorinated benzothiadiazole (BT) as an acceptor block is reported. Fluorination of BT can enhance crystallinity and planarity of the polymer backbone due to intramolecular F-S interactions. This also leads to deeper highest occupied molecular orbital (HOMO) energy levels leading to high J SC and V OC. The PSC properties of this series of new copolymer donors blended with fullerene acceptors show a homogeneous and uniform fibrous network in the blend film. The most homogeneous film was achieved with monofluorinated BT (PFDHI-TFT) that resulted in better charge extraction pathway leading to high power conversion efficiency (PCE). The solar cell using PFDHI-TFT as donor and fullerene acceptor showed PCE of 5.98% with V OC of 0.80 V, J SC of 10.56 mA cm −2 , and fill factor (FF) of 0.71, respectively, under AM 1.5G illumination (100 mW cm −2) in the absence of annealing.

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Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

New 3, 8‐difluoro indoloindole‐based copolymers for organic solar cell

et al. 2021

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“…Conjugated polymers have attracted much attention in the past decades as functional materials for multiple applications . They are widely used in design of organic solar cells (OSCs), organic field effect transistors, and other electronic devices . Synthesis of the vast majority of conjugated polymers is usually based on multistep protocols and technically is rather challenging.…”

Section: Introductionmentioning

confidence: 99%

Direct Heteroarylation versus Stille Polycondensation Reaction for the Synthesis of TQ1 Conjugated Polymer

Akkuratov

Prudnov

Chernyak

et al. 2019

J. Polym. Sci. Part A: Polym. Chem.

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We report a facile synthesis of the well‐known and highly promising conjugated polymer TQ1 using eco‐friendly direct heteroarylation reaction. Optimization of the reaction conditions yielded the target polymer with good optoelectronic and charge‐transport characteristics. The TQ1 polymer obtained in the direct heteroarylation reaction delivered power conversion efficiency of ∼5% in organic bulk heterojunction solar cells, which matches well the characteristics of the reference devices assembled using TQ1 batch synthesized via conventional Stille polycondensation reaction. The obtained results highlight the potential of the direct heteroarylation reaction as an efficient and environment‐friendly alternative to Stille cross‐coupling in the design of high‐quality semiconductor materials for organic electronics. © 2019 Wiley Periodicals, Inc. J. Polym. Sci., Part A: Polym. Chem. 2019, 57, 776–782

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“…Donor–acceptor (D–A) alternating copolymers have been widely used in organic photovoltaics (OPVs) − and organic field effect transistors (OFETs). − Numerous researches have been conducted to develop new donor monomers for making high-mobility D–A copolymers. − Reducing the conformational distortion of polymeric backbone in solid state to promote strong intermolecular π–π interactions is a guideline to develop high-performance conjugated polymers. − The incorporation of trans -1,2-vinylene (CHCH) linkage in the polymeric conjugated backbone not only sterically enhances the coplanarity but also electronically prolongs the conjugation. Poly(phenylenevinylene) (PPV) is the most representative polymer that has been extensively studied for polymer light-emitting diode applications. , Alternatively, ( E )-2-[2-(thiophen-2-yl)vinyl]thiophene unit, where a central vinylene is linked with two thiophenes (also denoted as TVT), emerges as a superior electron-rich donor to make D–A copolymers particularly for OPVs and OFETs applications. − To impart sufficient solubility of the polymers for solution-processability, it is necessary to copolymerize an unsubstituted TVT unit with an electron-accepting unit such as diketopyrrolopyrrole (DPP), perylene diimide (PDI), and naphthalene diimide (NDI), which contain nitrogen atoms to install aliphatic solubilizing groups.…”

Section: Introductionmentioning

confidence: 99%

Thiophene–Vinylene–Thiophene-Based Donor–Acceptor Copolymers with Acetylene-Inserted Branched Alkyl Side Chains To Achieve High Field-Effect Mobilities

Chiou

Hung

et al. 2018

Chem. Mater.

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2-Alkyl (1) alkyl (2) -type aliphatic side chains with a branching point position at the C 2 -position (such as 2-ethylhexyl or 2-octayldodecyl) have been widely implanted into numerous donor−acceptor conjugated copolymers for solution processable transistors or organic solar cells. However, the tertiary branching site located at the second carbon inevitably imposes steric hindrance that twists the main-chain coplanarity and attenuates interchain interactions. In this research, we developed a new two-dimensonal thiophene−vinylene−thiophene (TVT) derivative where a carbon−carbon triple bond is inserted between the thiophene unit and the 2-octyldodecyl group. This acetylene-incorporated TVT (aTVT) was copolymerized with 5,10-di(thiophen-2-yl)naphtho[1,2-c:5,6-c′]bis-([1,2,5]thiadiazole) (DTNT) and 5,6-difluoro-4,7-di(thiophen-2-yl)benzo[c][1,2,5]thiadiazole (DTFBT) to form the polymers PaTVT-NT and PaTVT-FBT, respectively. PTVT-FBT, without the triple bond, was also prepared for comparison. The insertion of a linear triple bond moves the tertiary carbon away from the main chain to reduce the steric hindrance, thereby improving the main-chain coplanarity and facilitating the interchain interactions. The acetylene-incorporated copolymers show better thermal stability, red-shifted absorption spectra, stronger intermolecular aggregation, lower-lying electron affinity, and much higher solid-state crystallinity. Due to the linear and coplanar polymeric backbone supported by theoretical calculation, PaTVT-NT exhibits high crystallinity and adopts strong stacking with an edge-on orientation in the thin film evidenced by 2D-GIXRD, leading to a high p-type OFET mobility up to 1.27 cm 2 V −1 s −1 with an on−off ratio of 9.22 × 10 5 . This value represents the highest value among the NT-based polymers. PaTVT-FBT also achieved a high mobility of 0.78 cm 2 V −1 s −1 , which greatly outperforms the corresponding nonacetylene PTVT-FBT counterpart. Most importantly, the preparation of 2-alkyl (1) alkyl (2) −acetylenyl side chain is synthetically feasible, which can be easily applied to create new conjugated polymers for high-performance solution-processable optoelectronics.

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Donor-acceptor-structured naphtodithiophene-based copolymers for organic thin-film transistors

Abstract: /Vs and an on/off ratio of 5.9 3 10 3 . V C

Cited by 6 publications

References 37 publications

New 3, 8‐difluoro indoloindole‐based copolymers for organic solar cell

New 3, 8‐difluoro indoloindole‐based copolymers for organic solar cell

Direct Heteroarylation versus Stille Polycondensation Reaction for the Synthesis of TQ1 Conjugated Polymer

Thiophene–Vinylene–Thiophene-Based Donor–Acceptor Copolymers with Acetylene-Inserted Branched Alkyl Side Chains To Achieve High Field-Effect Mobilities

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