- New angular-shaped and isomerically pure anthradithiophene with lateral aliphatic side chains for conjugated polymers: Synthesis, characterization, and implications for solution-prossessed organic field-effect transistors and photovoltaics
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An isomerically pure anti-anthradithiophene (aADT) arranged in an angular shape is developed. Formation of the framework of aADT incorporating four lateral alkyl substituents was accomplished by a one-pot benzannulation via multiple Suzuki coupling. This newly designed 2,8-stannylated aADT monomer was copolymerized with a ditheniodiketopyrrolopyrrole (DPP) unit and a bithiophene unit, respectively, to furnish an alternating donor-acceptor copolymer poly(anthradithiophene-alt-dithienyldiketopyrrolopyrrole) (PaADTDPP) and a thiophene-rich poly(anthradithiophene-alt-bithiophene) (PaADTT). PaADTT with crystalline nature achieved a high FET mobility of 7.9 × 10-2 cm2 V-1 s-1 with an on-off ratio of 1.1 × 107. The photovoltaic device based on the PaADTDPP:PC71BM (1:2.5, w/w) blend exhibited a Voc of 0.66 V, a Jsc of 9.49 mA/cm2, and a FF of 58.4%, delivering a power conversion efficiency (PCE) of 3.66%. By adding 1.5 vol % 1-chloronaphthalene (CN) as a processing additive, the PCE can be improved to 4.24%. We demonstrated that these angular-shaped and alkylated aADT-based polymers have better organic photovoltaic (OPVs) and field-effect transistor (FETs) characteristics than the linear-shaped ADT-containing polymers.
- Wu, Jhong-Sian,Lin, Chung-Te,Wang, Chien-Lung,Cheng, Yen-Ju,Hsu, Chain-Shu
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- Synthesis and properties of dicyanomethylene-endcapped thienopyrrole-based quinoidal S,N-heteroacenes
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A new series of highly π-extended dicyanomethyleneendcapped quinoidal S,N-heteroacenes (JH-quinoids) fused with thiophene and pyrrole rings have been designed and synthesized. The α-extension of the central S,N-heteroacene cores gives rise to significant red-shifted absorption maxima in solution without being affected by the long alkyl groups. The absorption maximum of JH10 with the longest quinoidal backbone in the thin film significantly red-shifted to the nearinfrared region of 1260nm as compared to that in solution (880 nm), indicating the formation of strong intermolecular interaction in the solid state. JH-quinoids maintain sufficiently low LUMO energy levels in the range of 14.09~4.22 eV regardless of the fused ring systems and substituents, while the HOMO energy levels increase with extending the length of S,N-heteroacenes; the highest HOMO energy level of JH10 is as high as -15.18 eV owing to the contributions from the nitrogen atoms and chalcogen. The molecular geometries of JH-quinoids optimized from the DFT calculations indicate their complete planar backbones and the trend of HOMO and LUMO energy levels variation is in good agreement with the cyclic voltammetry results. Consequently, the present JHquinoids should be promising candidates for ambipolar organic semiconductors.
- Jiang, Hua,Oniwa, Kazuaki,Xu, Zhanqiang,Bao, Ming,Yamamoto, Yoshinori,Jin, Tienan
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- A pentacyclic nitrogen-bridged thienyl-phenylene-thienyl arene for donor-acceptor copolymers: Synthesis, characterization, and applications in field-effect transistors and polymer solar cells
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A pentacyclic benzodipyrrolothiophene (BDPT) unit, in which two outer thiophene rings are covalently fastened with the central phenylene ring by nitrogen bridges, was synthesized. The two pyrrole units embedded in BDPT were constructed by using one-pot pa
- Tseng, Cheng-An,Wu, Jhong-Sian,Lin, Tai-Yen,Kao, Wei-Shun,Wu, Cheng-En,Hsu, So-Lin,Liao, Yun-Yu,Hsu, Chain-Shu,Huang, Huan-Yi,Hsieh, You-Zung,Cheng, Yen-Ju
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- Pluripotent Features of Doubly Thiophene-Fused Benzodiphospholes as Organic Functional Materials
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Linear ladder-type π-conjugated molecules have attracted much interest because of their intriguing physicochemical properties. To modulate their electronic structures, an effective strategy is to incorporate main-group elements into ladder-type π-conjugated molecules. In line with this strategy, a variety of ladder-type π-conjugated molecules with main-group elements have been synthesized to explore their potential utility as organic functional materials. In this context, phosphole-based π-conjugated molecules are highly attractive, owing to their unique optical and electrochemical properties, which arise from the phosphorus atom. Herein, the synthesis and physicochemical properties of doubly thiophene-fused benzodiphospholes, as a new class of phosphole-based ladder-type π-conjugated molecule, are reported. Systematic investigations into the physicochemical properties of doubly thiophene-fused benzodiphospholes revealed their pluripotent features: intense near-infrared fluorescence, excellent two-photon absorption property, and remarkably high electron-transporting ability. This study demonstrates the potential utility of doubly thiophene-fused benzodiphospholes as organic functional materials for biological imaging, nonlinear optics, organic transistors, and organic photovoltaics.
- Higashino, Tomohiro,Ishida, Keiichi,Sakurai, Tsuneaki,Seki, Shu,Konishi, Tatsuki,Kamada, Kenji,Imahori, Hiroshi,Imahori, Hiroshi
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supporting information
p. 6425 - 6438
(2019/04/26)
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- NON-FULLERENE ELECTRON ACCEPTORS
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The invention provides electron acceptor compound of Formula (I) which may be used in organic compositions for optical or electronic devices.
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Page/Page column 31-32
(2017/12/13)
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- HETEROCYCLIC COMPOUND AND ORGANIC SOLAR CELL COMPRISING THE SAME
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The present specification relates to a heterocyclic compound and an organic solar cell comprising the same. In addition, the organic solar cell comprises: a first electrode; a second electrode provided on the opposite side of the first electrode; and one
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Paragraph 0208; 0209; 0210; 0216
(2016/10/08)
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- Condensed compound and organic light emitting diode comprising the same
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The present invention provides a condensed-cyclic compound represented by Formula 1, and an organic electroluminescent device including the same. Refer to detailed description of the present invention for Ar_1 to Ar_4 and R_1 to R_6 in the Formula 1. The organic electroluminescent device may include an organic layer containing the condensed-cyclic compound with low driving voltage, high luminance, high efficiency,and improved durability.COPYRIGHT KIPO 2015
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Paragraph 0285; 0288; 0289
(2016/10/27)
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- Electron-rich pyrroloindacenodithiophenes: Synthesis, characterization, and spectroscopic studies
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N-Alkyl substituted pyrroloindacenodithiophene (PIDT) and their phenyl substituted derivatives were synthesized. Their single-crystal structures and electrochemical and spectroscopic properties were investigated. Experimental results showed PIDT displayed strong electron-donating properties, reversible redox behaviors, and strong fluorescence and could be controlled to oxidize to radical cation and dication with distinctive optical changes. These attractive properties demonstrated the potential applications of PIDT in the field of switches, molecular machines, and information memories.
- Xiong, Yu,Wu, Qinghe,Li, Jie,Wang, Shitao,Gao, Xike,Li, Hongxiang
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supporting information
p. 752 - 756
(2013/02/26)
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- Polymers Derived from Benzobis(silolothiophene) and their Use as Organic Semiconductors
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The invention relates to conjugated polymers comprising benzo-bis(silolothiophene) units or derivatives thereof, to methods of their preparation, to novel monomer units used therein, to the use of the polymers in organic electronic (OE) devices, and to OE
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