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- 주제어 : fluorinated benzothiadiazole (검색결과 4 건)
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장문정,이정훈,이상면,유도혁,신태주,양창덕,오준학 한국공업화학회 2015 한국공업화학회 연구논문 초록집 Vol.2015 No.1
To assess a rich data set for the influence of the fluorinated 2,1,3-benzothiadiazole (BT) units on the charge-transport characteristics in organic field-effect transistors (OFETs), we synthesized two new polymers (PDPP-FBT and PDPP-2FBT) incorporating diketopyrrolopyrrole (DPP) and either single- or double-fluorinated BT and thoroughly investigated them via a range of techniques. The resulting polymers exhibited electron-dominant ambipolar transport behavior with more stable n-channel operation.
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Fluorinated benzothiadiazole-based small molecules for photovoltaic applications
Putri, Sella Kurnia,Lee, Min Seok,Chang, Dong Wook,Kim, Joo Hyun Elsevier 2016 Synthetic metals Vol.220 No.-
<P><B>Abstract</B></P> <P>A series of medium band gap conjugated small molecules with a typical D-π-A-π-D structure, in which triphenylamine, thiophene, and benzothiadiazole are used as an electron-donor, a bridge, and an electron-acceptor, respectively, have been synthesized. To investigate the effects of strong electron-withdrawing fluorine atoms on various properties, one and two fluorine substituents are introduced to the central benzothiadiazole unit of N-(4-(5-(7-(5-(4-(diphenylamino)phenyl)thiophen-2-yl)benzo[c][1,2,5]thiadiazol-4-yl)thiophen-2-yl)phenyl)-N-phenylbenzenamine (<B>TPA-TBT</B>) to give <B>TPA-TBT-1F</B> and <B>TPA-TBT-2F</B>, respectively. Owing to the significant contributions of fluorine atoms, these small molecules exhibit clearly distinctive optical and electrochemical properties. Inverted-type organic photovoltaic cells (OPVs) with a configuration of ITO/ZnO/small molecules: PC<SUB>71</SUB>BM/MoO<SUB>3</SUB>/Al were fabricated and the fabricated cells showed maximum power conversion efficiencies of 0.84, 1.15 and 1.70% for <B>TPA-TBT</B>, <B>TPA-TBT-1F</B> and <B>TPA-TBT-2F</B>, respectively. The superior photovoltaic performance of <B>TPA-TBT-2F</B> is attributed to the relatively deep energy level of highest occupied molecular orbital (HOMO) and to more balanced electron- and hole-mobility within photoconversion layer. Therefore, this study can provide insights into the tuning the properties of benzothiadiazole-based small molecules by introducing fluorine substituents.</P> <P><B>Highlights</B></P> <P> <UL> <LI> A series of medium band gap conjugated small molecules have been synthesized. </LI> <LI> Selective incorporation of fluorine atoms on the benzothiadiazole acceptors. </LI> <LI> Optical, electrochemical and photovoltaic properties have been investigated. </LI> </UL> </P> <P><B>Graphical abstract</B></P> <P>[DISPLAY OMISSION]</P>
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Lee, Junghoon,Jang, Moonjeong,Lee, Sang Myeon,Yoo, Dohyuk,Shin, Tae Joo,Oh, Joon Hak,Yang, Changduk American Chemical Society 2014 ACS APPLIED MATERIALS & INTERFACES Vol.6 No.22
<P>Over the past few years, one of the most remarkable advances in the field of polymer solar cells (PSCs) has been the development of fluorinated 2,1,3-benzothiadiazole (BT)-based polymers that lack the solid working principles of previous designs, but boost the power conversion efficiency. To assess a rich data set for the influence of the fluorinated BT units on the charge-transport characteristics in organic field-effect transistors (OFETs), we synthesized two new polymers (<B>PDPP-FBT</B> and <B>PDPP-2FBT</B>) incorporating diketopyrrolopyrrole (DPP) and either single- or double-fluorinated BT and thoroughly investigated them via a range of techniques. Unlike the small differences in the absorption properties of <B>PDPP-FBT</B> and its nonfluorinated analogue (<B>PDPP-BT</B>), the introduction of doubly fluorinated BT into the polymer backbone induces a noticeable change in its optical profiles and energy levels, which results in a slightly wider bandgap and deeper HOMO for <B>PDPP-2FBT</B>, relative to the others. Grazing incidence X-ray diffraction (GIXD) analysis reveals that both fluorinated polymer films have long-range orders along the out-of-plane direction, and π–π stacking in the in-plane direction, implying semicrystalline lamellar structures with edge-on orientations in the solid state. Thanks to the strong intermolecular interactions and highly electron-deficient π-systems driven by the inclusion of F atoms, the polymers exhibit electron mobilities of up to 0.42 and 0.30 cm<SUP>2</SUP> V<SUP>–1</SUP> s<SUP>–1</SUP> for <B>PDPP-FBT</B> and <B>PDPP-2FBT</B>, respectively, while maintaining hole mobilities higher than 0.1 cm<SUP>2</SUP> V<SUP>–1</SUP> s<SUP>–1</SUP>. Our results highlight that the use of fluorinated BT blocks in the polymers is a promising molecular design strategy for improving electron transporting performance without sacrificing their original hole mobility values.</P><P><B>Graphic Abstract</B> <IMG SRC='http://pubs.acs.org/appl/literatum/publisher/achs/journals/content/aamick/2014/aamick.2014.6.issue-22/am505925w/production/images/medium/am-2014-05925w_0007.gif'></P><P><A href='http://pubs.acs.org/doi/suppl/10.1021/am505925w'>ACS Electronic Supporting Info</A></P>
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Choi, E.Y.,Eom, S.H.,Song, C.E.,Nam, S.Y.,Lee, J.,Woo, H.Y.,Jung, I.H.,Yoon, S.C.,Lee, C. Elsevier Science 2017 Organic Electronics Vol.46 No.-
We synthesized a novel wide bandgap polymer, PDTFBT, forming a weak donor (WD)-weak acceptor (WA) structure for use in organic photodetectors (OPDs) and organic solar cells (OSCs). The fluorination in the D unit and the alkoxy substitution in the A unit induced WD and WA properties, respectively. The WD-WA structure of PDTFBT effectively broadened the bandgap compared to typical D-A structures, and the S-F and S-O dipole-dipole interactions induces a highly planar backbone structure with excellent π-π stacking in the vertical direction. In OPDs, conformationally less disordered PDTFBT polymer retained the constant responsivity and significantly improved the detectivity of PDTFBT:PC<SUB>71</SUB>BM devices even with a thick active layer of 470 nm, contrary to the variation in the responsivity of P3HT:PC<SUB>61</SUB>BM devices depending on the thickness. In OSCs, the deep HOMO energy level (-5.57 eV) of PDTFBT led to high Voc of 0.92 V in PDTFBT:PC<SUB>71</SUB>BM devices, which was 0.3 eV higher than that of P3HT:PC<SUB>61</SUB>BM devices (0.62 V), resulting in 1.8-fold enhanced power conversion efficiency. We demonstrated that the WD-WA structure with S-F and S-O interactions is highly promising strategy to make wide bandgap polymers for organic photodetectors and for the bottom cell of tandem architecture.
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