Semiconducting π-extended porphyrin dimer and its characteristics in OFET and OPVC

Park, Woo Jea; Chae, Seung Hyun; Shin, Jicheol; Choi, Dong Hoon; Lee, Suk Joong

doi:10.1016/j.synthmet.2015.04.017

Cited by 12 publications

(5 citation statements)

References 35 publications

(11 reference statements)

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“…Using the π-extended strategy, single-crystal OFETs made of four 2-ethynyl-5-hexylthiophene peripheral-arms-substituted porphyrin derivatives (H 2 TP (17c) and ZnTP (18a)) provided mobilities as high as 0.85 and 2.90 cm 2 V −1 s −1 , respectively, which are higher than those of film devices [68]. Similarly, OFETs of the π-extended porphyrin derivatives (2TBPH (19a), 2TBPZ (19b), TEPP (20a), DTEPP (20b), 20c, 20d, PD-1 (21), H2TPEP (22a), and ZnTPEP (22b)) displayed high hole mobilities ranging from 0.026 to 2.57 cm 2 V −1 s −1 [69][70][71][72][73]. For double-thiophenesubstituted porphyrin derivatives (H2DTP (23a), NiDTP (23b), and CuDTP (23c)) [74], their single-crystal OFETs exhibited mobilities of up to 0.15, 1.50, and 0.74 cm 2 V −1 s −1 , respectively.…”

Section: P-type Macrocycle Semiconductorsmentioning

confidence: 94%

Structure–Property Relationship of Macrocycles in Organic Photoelectric Devices: A Comprehensive Review

et al. 2023

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Macrocycles have attracted significant attention from academia due to their various applications in organic field-effect transistors, organic light-emitting diodes, organic photovoltaics, and dye-sensitized solar cells. Despite the existence of reports on the application of macrocycles in organic optoelectronic devices, these reports are mainly limited to analyzing the structure–property relationship of a particular type of macrocyclic structure, and a systematic discussion on the structure–property is still lacking. Herein, we conducted a comprehensive analysis of a series of macrocycle structures to identify the key factors that affect the structure–property relationship between macrocycles and their optoelectronic device properties, including energy level structure, structural stability, film-forming property, skeleton rigidity, inherent pore structure, spatial hindrance, exclusion of perturbing end-effects, macrocycle size-dependent effects, and fullerene-like charge transport characteristics. These macrocycles exhibit thin-film and single-crystal hole mobility up to 10 and 26.8 cm2 V−1 s−1, respectively, as well as a unique macrocyclization-induced emission enhancement property. A clear understanding of the structure–property relationship between macrocycles and optoelectronic device performance, as well as the creation of novel macrocycle structures such as organic nanogridarenes, may pave the way for high-performance organic optoelectronic devices.

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Section: P-type Macrocycle Semiconductorsmentioning

confidence: 94%

Structure–Property Relationship of Macrocycles in Organic Photoelectric Devices: A Comprehensive Review

et al. 2023

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“…Despite the utilization of solvent additives to modulate the device performance in photovoltaic and thermoelectric devices, its significance in polymer OFET is less explored. Solvent additives like DIO and chloronaphthalene were previously used as morphology modifiers for achieving enhanced mobility. − By introducing solvent additives of varying volatility, the alignment of the polymer chains is modulated, and the charge transport property is also regulated. − Less volatile solvent additives are reported to help in controlling the thin film morphology to achieve better charge transport, nevertheless residuals of these solvents hamper the stability of the device. Even DIO is reported to form photoacid in the presence of light, hence, any of its residuals degrades the device performance further .…”

Section: Introductionmentioning

confidence: 99%

Tuning Polymer Semiconductor Morphology through Additive Engineering for a Stable Phototransistor

Choudhury

Gupta

Garai

et al. 2021

ACS Appl. Electron. Mater.

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The application of PTB7-Th polymer as an efficient semiconductor material in a phototransistor (PT) has been demonstrated, with a strategy to improve the hole transport and enhance the device stability under dark as well as illumination conditions. The results have been established using two solvent additives, namely 1,8-diiodooctane (DIO) and 1,8-dibromooctane (DBrO) which have the ability to modulate the polymer morphology. These additives also improve the charge transport properties and help in achieving higher mobility in organic field effect transistors (OFETs). The DIO and DBrO-modified devices show an increase in mobility (0.09 and 0.22 cm2/V-s, respectively) with respect to the control device (without any additive). Further, the device stability in the dark as well as under illumination improves drastically for the DBrO-modified device, whereas photodegradation of the DIO-modified device is observed. The photophysical studies, AFM, FESEM, XRD, and electrical investigations were carried out to understand the effect of the solvent additive in lowering the contact resistance, suppressing traps, and improving the morphology. With the optimized concentration of DBrO as the solvent additive, a PTB7-Th based PT is implemented and a responsivity of 688 A/W is obtained.

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“…Park et al reported a pi-extended porphyrin dimer with a field-effect mobility of 1.32 × 10 −2 cm 2 /Vs and an on/off ratio of 10 5 . 15 Chae et al reported tetrakis((4hexylphenyl)ethynyl) porphyrin with 0.029 cm 2 /Vs charge carrier mobility and an on/off ratio of 10 4 . 8 These studies reported pi-extended planar porphyrins as one of the best candidates for the OFET fabrication.…”

Section: ■ Introductionmentioning

confidence: 99%

“…Of the various molecules under investigation for organic electronics, porphyrins and their related macrocycles are of special interest because they are robust and their properties can be modulated by chelation of a metal ion and functionalization on the macrocycle. Park et al reported a pi -extended porphyrin dimer with a field-effect mobility of 1.32 × 10 –2 cm 2 /Vs and an on/off ratio of 10 5 . Chae et al reported tetrakis((4-hexylphenyl)ethynyl) porphyrin with 0.029 cm 2 /Vs charge carrier mobility and an on/off ratio of 10 4 .…”

Section: Introductionmentioning

confidence: 99%

Solution-Processable meso-Triarylamine Functionalized Porphyrins with a High Mobility and ON/OFF Ratio in Bottom-Gated Organic Field-Effect Transistors

Kurlekar

Anjali

Sonalin

et al. 2020

ACS Appl. Electron. Mater.

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A series of metal-free porphyrin molecules with functionalized triarylamines at the meso-position are designed and synthesized. All the functionalized porphyrins possess good thermal stability and high decomposition temperatures over 422 °C and also exhibited electrochemical reproducibility. The calculated ionization potentials are in the range of −5.01 to -5.42 eV, and electron affinity levels are in between −2.47 and −2.91 eV, which supports stable charge ejection. Organic fieldeffect transistor (OFET) devices with bottom-gate/top-contact architecture are fabricated by a solution-processable technique. OFETs with an active layer of porphyrin with electron-accepting trifluorophenyl groups gave the highest charge carrier mobility of 4.4 cm 2 /Vs and an on/off ratio of 10 7 . The obtained results indicate these compounds to be efficient hole-transporting materials. This research work presents the highest mobilities of the porphyrins reported until now.

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Semiconducting π-extended porphyrin dimer and its characteristics in OFET and OPVC

Cited by 12 publications

References 35 publications

Structure–Property Relationship of Macrocycles in Organic Photoelectric Devices: A Comprehensive Review

Structure–Property Relationship of Macrocycles in Organic Photoelectric Devices: A Comprehensive Review

Tuning Polymer Semiconductor Morphology through Additive Engineering for a Stable Phototransistor

Solution-Processable meso-Triarylamine Functionalized Porphyrins with a High Mobility and ON/OFF Ratio in Bottom-Gated Organic Field-Effect Transistors

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