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Enhanced open-circuit voltages of trifluoromethylated quinoxaline-based polymer solar cells
Putri, Sella Kurnia,Jin, Ho Cheol,Whang, Dong Ryeol,Kim, Joo Hyun,Chang, Dong Wook Elsevier 2019 ORGANIC ELECTRONICS Vol.65 No.-
<P><B>Abstract</B></P> <P>Three quinoxaline-based conjugated polymers with donor-π-acceptor configurations have been synthesized by Stille coupling reaction. The electron-donating 2,3-dioctylthienyl- substituted benzodithiophene (BDT) unit was linked to the electron-accepting 2,3-diphenylquinoxaline (DPQ) group through a thiophene bridge, to produce a reference polymer <B>PTBDT-Qx</B>. Furthermore, the strong electron-withdrawing trifluoromethyl moieties were introduced at the <I>para</I>-position of the phenyl groups in the 2,3-positions of DPQ and 6,7-difluorinated DPQ, to afford <B>PTBDT-QxCF3</B> and <B>PTBDT-FQxCF3</B>, respectively. Owing to the continuous reduction in their HOMO energy levels with increasing number of electron-withdrawing groups, the open-circuit voltage (<I>V</I> <SUB>oc</SUB>) in polymer solar cells (PSCs) shows a gradual improvement in the order of <B>PTBDT-Qx</B> < <B>PTBDT-QxCF3</B> < <B>PTBDT-FQxCF3</B>. The inverted-type PSC based on <B>PTBDT-FQxCF3</B> with a configuration of ITO/ZnO/polymer:PC<SUB>71</SUB>BM/MoO<SUB>3</SUB>/Al provides the best power conversion efficiency of 6.47%, together with a <I>V</I> <SUB>oc</SUB> of 0.99 V, a short-circuit current of 10.03 mA/cm<SUP>2</SUP>, and a fill factor of 65.1%.</P> <P><B>Highlights</B></P> <P> <UL> <LI> A series of conjugated polymers based on quinoxaline have been synthesized. </LI> <LI> Incorporation of trifluoromethyl group on the quinoxaline acceptors. </LI> <LI> Optical, electrochemical and photovoltaic properties have been investigated. </LI> </UL> </P> <P><B>Graphical abstract</B></P> <P>A series of trifluoromethylated quinoxaline-based polymers were systematically synthesized by Stille coupling reaction. The results obtained in this study clearly reveal the significant contribution of the electron-withdrawing trifluoromethyl groups in enhancing the open-circuit voltages, as well as producing a sharp improvement in the power conversion efficiencies of polymer solar cells with bulk-heterojunction structure.</P> <P>[DISPLAY OMISSION]</P>
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>
김준태,진호철,Sella Kurnia Putri,황동렬,김주현,장동욱 한국고분자학회 2019 Macromolecular Research Vol.27 No.12
Three quinoxaline-based small molecules possessing multiple electronwithdrawing moieties were synthesized by the Suzuki coupling reaction for organic photovoltaic cells (OPVs). The electron-donating triarylamine units were linked to both ends of electron-accepting 2,3-diphenyl quinoxaline (DPQ) derivatives with strong electron-withdrawing trifluoromethyl (CF3) moieties to produce a reference D-A-D type small molecule of CF3Qx-0F. Furthermore, one and two fluorine atoms were additionally introduced to the 6,7-positions of the DPQ unit of CF3Qx-0F affording CF3Qx-1F and CF3Qx-2F, respectively. Owing to the significant contribution of the electron-withdrawing CF3 and fluorine units, all invertedtype OPVs based on three small molecules exhibited high open circuit voltages greater than 0.82 V. In addition, the power conversion efficiencies (PCEs) of the devices were gradually improved with increasing number of fluorine atoms. The highest PCE (2.82%) with a V oc of 0.88 V, a short-circuit current of 6.38 mA cm-2, and a fill factor of 50.6% was achieved from the device based on CF3Qx-2F.
Shinta Lieviana Handoko,진호철,황동렬,Sella Kurnia Putri,김주현,장동욱 한국공업화학회 2019 Journal of Industrial and Engineering Chemistry Vol.73 No.-
Two quinoxaline-based conjugated polymers with multiple electron-withdrawing moieties weresynthesized by the Stille coupling reaction for polymer solar cells (PSCs). For the construction of a typicaldonor-p-acceptor structure, the electron-donating indacenodithiophene (IDT) and indacenodithieno[3,2-b]thiophene (IDTT) were linked to the electron-withdrawing quinoxaline (DPQCF3F) that containedtrifluoromethyl andfluorine units via a thiophene bridge to produce PIDT-Qx and PIDTT-Qx, respectively. Owing to the significant contribution of the DPQCF3F unit in the polymer backbone, Voc of the inverted-type PSCs was increased up to 0.92 V. In addition, the replacement of two thiophenes of IDT to two thieno[3,2-b] thiophene units of IDTT in the quinoxaline-based polymer backbone can efficiently improved thelight absroption and charge carrier mobility of the resultant polymer. Therefore, a higher PCE of 4.54%was achieved from the device based on PIDTT-Qx with a short circuit current density of 9.30 mA/cm2, anopen-circuit voltage of 0.92 V, and afill factor of 53%, compared with the device based on PIDT-Qx(2.83%).