- Dithieno[3,2-b:2′,3′-d]pyrrole-benzo[c][1,2,5]thiadiazole conjugate small molecule donors: Effect of fluorine content on their photovoltaic properties
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Two new small molecule donors, namely ICT4 and ICT6 with D1-A-D2-A-D1 architecture having 2,4-bis(2-ethylhexyl)-4H-dithieno[3,2-b:2′,3′-d]pyrrole (EHDTP, D1) and 4,8-bis((2-ethylhexyl)oxy)benzo[1,2-b:4,5-b′]dithiophene (OBDT, D2) as the terminal and central donor, and benzo[c][1,2,5]thiadiazole (BT for ICT4) and 5,6-difluorobenzo[c][1,2,5]thiadiazole (F2BT for ICT6) as the acceptor (A) moieties, are synthesized and their optical, electronic and photovoltaic properties are investigated. Both ICT4 and ICT6 have considerable solubility in various solvents and possess efficient light absorption ability [ε (×105 mol-1 cm-1) is 0.99 and 1.06, respectively for ICT4 and ICT6] and appropriate frontier molecular orbital energy offsets with [6,6]-phenyl-C71-butyric acid methyl ester (PC71BM). Bulk heterojunction solar cells (BHJSCs) are fabricated using ICT4/ICT6 and PC71BM as donors and acceptors, respectively and BHJSCs with two-step annealed (thermal followed by solvent vapor annealing) active layers of ICT4 and ICT6 show overall power conversion efficiencies (PCEs) of 5.46% and 7.91%, respectively. The superior photovoltaic performance of the ICT6 based BHJSCs is due to the favourable morphology with a nanoscale interpenetrating network in the ICT6:PC71BM active layer induced by the fluorine atoms on the BT acceptor, which significantly enhances the dissociation of excitons, charge transport and the charge collection efficiency, and suppresses bimolecular recombination in the BHJ. The observed higher PCE of 7.91% indicates that ICT6 is one of the best BT based donor material for small molecular BHJSCs.
- Busireddy, Manohar Reddy,Chereddy, Narendra Reddy,Shanigaram, Balaiah,Kotamarthi, Bhanuprakash,Biswas, Subhayan,Sharma, Ganesh Datt,Vaidya, Jayathirtha Rao
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- Synthesis and photovoltaic properties of low band gap polymers containing benzo[1,2- b:4,5- c ′]dithiophene-4,8-dione
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Two low-bandgap polymers P1 and P2 were synthesized by copolymerization of benzo[1,2-b:4,5-c']-dithiophene-4,8-dione (BDTD) with benzo-[1,2-b:4,5-b'] dithiophene (BDT) and dithieno[3,2- b:2',3'-d]silole (DTS), respectively. Thermogravimetric analyses of P1 and P2 were found and the temperature of 5% weight-loss was selected as the onset point of decomposition. Both the polymers are found to exhibit low-lying HOMO and good light-absorption properties. The absorption spectra of the polymers in chloroform and films are found to be of the range of 500-650 nm. The optimized weight ratios for P1 and P2 both are found to be 1:1.5. The AFM images show the morphology change for the polymer/PC61BM composite films and the rms roughness for the film is found to decrease from 6.94 to 0.47 nm. P2 device exhibits higher external quantum efficiency (EQE) than that of P1, which is due to stronger sunlight absorption of P2 film.
- Cao, Jiamin,Zhang, Wei,Xiao, Zuo,Liao, Lingyan,Zhu, Weiguo,Zuo, Qiqun,Ding, Liming
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- Synthesis and characterization of organic semiconducting polymers containing dithienylfluorenone for use in organic photovoltaic cells
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2,7-Bis(5-bromo-4-hexylthiophen-2-yl)-9H-fluoren-9-one (DTFO) was synthesized as a new electron-accepting material in semiconducting polymers for use in photovoltaic devices. The synthesized DTFO was polymerized with two different electron-donating counter monomers:2,7-dibromo-9,9-dioctyl-9H-fluorene (DOF) and 2,6-bis(trimethyltin)-4,8-di(2-ethylhexyloxyl)benzo [1,2-b:4,5-b']dithiophene (BDT). Two alternating copolymers, poly(DTFO-alt-DOF) and poly(DTFOalt-BDT), were synthesized through the Suzuki and Stille coupling polymerizations, respectively. The synthesized polymers exhibited good solubility in common solvents and show good thermal stability up to 350 °C. The optical band gap energies of poly(DTFO-alt-DOF) and poly(DTFO-alt-BDT) were determined to be 2.44 and 2.23 eV, respectively. The positions of the highest occupied molecular orbital (HOMO) and lowest unoccupied molecular orbital (LUMO) of the polymers were determined by cyclic voltammetry (CV). One of these devices showed a power conversion efficiency of 0.50%, with an open-circuit voltage of 0.67 V, a short-circuit current of 2.34 mA/cm2, and a fill factor of 0.30 under air mass (AM) 1.5 global (1.5 G) illumination conditions (100 mW/cm2). Copyright
- Byun, Yun-Sun,Kim, Ji-Hoon,Park, Jong Baek,Hwang, Do-Hoon
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- Thieno[3,4-b]thiophene ebenzo[1,2-b:4,5-b′]dithiophene-based polymers bearing optically pure 2-ethylhexyl pendants: Synthesis and application in polymer solar cells
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Optically active narrow-bandgap polymers ((R,R)- and (S,S)-PTB5) consisting of alternating n-octyl thieno [3,4-b]thiophene-2-carboxylate and benzo[1,2-b:4,5-b′]dithiophene units bearing optically pure (R)- and (S)-2-ethylhexyl pendants, respectively, were synthesized for the first time. (R,R)- and (S,S)-PTB5 films showed apparent circular dichroism in their absorption regions of the polymer backbone due to the formation of a chirally ordered superstructure induced by the chirality of the branched alkyl pendants. Inverted-type bulk heterojunction polymer solar cells (PSCs) were fabricated using (R,R)- or (S,S )-PTB5 as electron donors and [6,6]-phenyl-C61-butyric acid methyl ester as an electron acceptor. The photovoltaic properties of the PSCs were compared with those of the corresponding PSC containing optically inactive PTB5 bearing racemic 2-ethylhexyl pendants.
- Ikai, Tomoyuki,Kojima, Ryotaro,Katori, Sinji,Yamamoto, Tomoyuki,Kuwabara, Takayuki,Maeda, Katsuhiro,Takahashi, Kohshin,Kanoh, Shigeyoshi
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- Polymer solar cells based on quinoxaline and dialkylthienyl substituted benzodithiophene with enhanced open circuit voltage
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A poly[benzodithiophene-alt-di-2-thienyl-quinoxaline] series (PBDTDPQ-EH, PBDTDPQ-OD, and PBDTDPQ-HDT) was synthesized via Stille coupling. Deep highest occupied molecular orbital (HOMO) levels were achieved by the introduction of 2-decyl-4-hexyl-thiophen-yl (HDT) side chains. The introduction of the various side chains increased the molecular weight of the polymers, and the polymers dissolved well in common organic solvents at room temperature. The HOMO energy level (-5.20 to -5.49 eV) decreased because of the 2D conjugated structure. X-ray diffraction analysis showed that PBDTDPQ-OD had a slightly edge-on structure. In the case of PBDTDPQ-HDT, however, the structure was amorphous due to the thiophene side chain, and the extent of π stacking increased. After fabricating bulk-heterojunction-type polymer solar cells, the OPV characteristics were evaluated. The values of open-circuit voltage (V oc), short-circuit current (Jsc), fill factor, and power conversion efficiency (PCE) were 0.88 V, 7.9 mA cm-2, 45.4%, and 3.2%, respectively.
- Song, Kwan Wook,Lee, Tae Ho,Ko, Eui Jin,Back, Kyung Hun,Moon, Doo Kyung
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- Effect of fluorine on optoelectronic properties in DI-A-DII-A-DI type organic molecules: A combined experimental and DFT study
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The impact of the substitution of fluorine atom/atoms on the optoelectronic features of organic molecules having DI-A-DII-A-DI type architecture is examined in the current work. The three synthesized organic molecules (SMD1, SMD2 and SMD3) comprise of a dithienopyrrole (DTP) derivative as a central donor (DII), which is flanked between two benzothiadiazole (BT) moieties (electron acceptors, A). The BT core on each of two ends is joined to an electron-donating benzodithiophene (BDT) derivative (DI). The SMD1, SMD2 and SMD3 are substituted with 0, 2 and 4 fluorine atoms on their BT moiety respectively. The assistance of DFT methods is taken to evaluate the influence of fluorine on reorganization energies, ionizing potential and electron affinity of molecules. The thermal stability of molecules is mapped by TGA studies. Cyclic voltammetry studies are carried out to comprehend the characteristics of highest molecular orbital, lowest unoccupied molecular orbital and the bandgap of molecules, which are also supported by DFT methods. The molecules displayed better absorption properties in the near-infrared (NIR) region, excellent solution processability in a variety of organic solvents, low bandgap and optimum thermal toughness to make them applicable in the construction of OBHJSCs to play the role of donor materials when connected with acceptors like fullerene derivatives.
- Appalanaidu, Ejjurothu,Busireddy, Manohar Reddy,Chetti, Prabhakar,Vaidya, Jayathirtha Rao,Vidya, V. M.
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- Effects of π-conjugated bridges on photovoltaic properties of donor-π-acceptor conjugated copolymers
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A series of conjugated donor (D)-π-acceptor (A) copolymers, P(BDT-F-BT), P(BDT-T-BT), and P(BDT-TT-BT), based on benzodithiophene (BDT) donor unit and benzothiadiazole (BT) acceptor unit with different π-bridges, were designed and synthesized via a Pd-catalyzed Stille-coupling method. The π-bridges between the BDT donor unit and BT acceptor unit are furan (F) in P(BDT-F-BT), thiophene (T) in P(BDT-T-BT) and thieno[3,2-b]thiophene (TT) in P(BDT-TT-BT). It was found that the π-bridges significantly affect the molecular architecture and optoelectronic properties of the copolymers. With the π-bridge varied from furan to thiophene, then to thieno[3,2-b]thiophene, the shape of the molecular chains changed from z-shaped to almost straight line gradually. Band gaps of P(BDT-F-BT), P(BDT-T-BT) and P(BDT-TT-BT) were tuned from 1.96 to 1.82 to 1.78 eV with HOMO levels up-shifted from -5.44 to -5.35 to -5.21 eV, respectively. Bulk heterojunction solar cells with the polymers as donor and PC71BM as acceptor demonstrated power conversion efficiency varied from 2.81% for P(BDT-F-BT) to 3.72% for P(BDT-T-BT) and to 4.93% for P(BDT-TT-BT). Compared to furan and thiophene, thieno[3,2-b]thiophene π-bridge in the copolymers shows superior photovoltaic performance. The results indicate that the photovoltaic performance of some high efficiency D-A copolymers reported in literatures could be improved further by inserting suitable π-bridges.
- Wang, Xiaochen,Sun, Yeping,Chen, Song,Guo, Xia,Zhang, Maojie,Li, Xiaoyu,Li, Yongfang,Wang, Haiqiao
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- Efficient polymer solar cells based on the copolymers of benzodithiophene and thienopyrroledione
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Bulk heterojunction solar cells based on a novel low band gap polymer, PBDTTPD, were investigated. In the conventional device structures, a power conversion efficiency of 4.1% could be achieved from the thin film blend of PBDTTPD:PC71BM(1:2) with a current density of 9.8mAcm-2, Voc of 0.84 V, and FF of ~ 50%. The high Voc (0.87 V) is the result of the lower HOMO level of the polymer. In addition, inverted devices with PBDTTPD: PC71BM (1:2) as active layer were also investigated.
- Zhang, Yong,Hau, Steven K.,Yip, Hin-Lap,Sun, Ying,Acton, Orb,Jen, Alex K.-Y.
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- Synthesis and photovoltaic properties of new low bandgap isoindigo-based conjugated polymers
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A series of new isoindigo-based low banbap polymers, containing thiophene, thieno[3,2-b]thiophene and benzo[1,2-b:4,5-b′]dithiophene as donors, have been synthesized by Stille cross-coupling reaction. Their photophysical, electrochemical and photovoltaic properties have been investigated. These new polymers exhibit broad and strong absorption between 400 and 800 nm with absorption maxima around 700 nm. The HOMO energy levels of polymers vary between -5.20 and -5.49 eV and the LUMO energy levels range from -3.66 to -3.91 eV. The optical bandgaps of the polymers are optimized for solar cell applications and they are at about 1.5 eV. Polymer solar cells (PSC) based on these new polymers were fabricated with device structures of ITO/PEDOT:PSS/polymers: PC 71BM (1:2, w/w)/LiF/Al. The photovoltaic properties of the polymers have been evaluated under AM 1.5G illumination at 100 mW/cm2 with a solar simulator. The combination of broad absorption, optimal bandgap and well matched energy levels with those of PCBMs makes these isoindigo-based low bandbap polymers promising materials for photovoltaic applications.
- Zhang, Guobing,Fu, Yingying,Xie, Zhiyuan,Zhang, Qing
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- Synthesis of Amphiphilic RuII Heteroleptic Complexes Based on Benzo[1,2-b:4,5-b′]dithiophene: Relevance of the Half-Sandwich Complex Intermediate and Solvent Compatibility
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The detailed synthesis and characterization of four ruthenium(II) complexes [RuLL′(NCS)2] is reported, in which L represents a 2,2′-bipyridine ligand functionalized at the 4,4′ positions with benzo[1,2-b:4,5-b′]dithiophene derivatives (BDT) and L′ is 2,2′-bipyridine-4,4′-dicarboxylic acid unit (dcbpy) (NCS=isothiocyanate). The reaction conditions were adapted and optimized for the preparation of these amphiphilic complexes with a strong lipophilic character. The photovoltaic performances of these complexes were tested in TiO2 dye-sensitized solar cell (DSSC) achieving efficiencies in the range of 3-4.5 % under simulated one sun illumination (AM1.5G).
- Urbani, Maxence,Medel, María,Kumar, Sangeeta Amit,Ince, Mine,Bhaskarwar, Ashok N.,González-Rodríguez, David,Gr?tzel, Michael,Nazeeruddin, Mohammad Khaja,Torres, Tomás
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- A novel D2-A-D1-A-D2-type donor–acceptor conjugated small molecule based on a benzo[1,2-b:4,5-b″]dithiophene core for solution processed organic photovoltaic cells
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A novel D2-A-D1-A-D2-type donor–acceptor conjugated small molecule (DTPA-Q-BDT-Q-DTPA) with a benzo[1,2-b:4,5-b′]dithiophene (BDT) core and two D2-A arms has been synthesized and employed as electron donor for organic solar cells. Solution-processed organic photovoltaic (OPV) devices were fabricated with a configuration of ITO/PEDOT:PSS/DTPA-Q-BDT-Q-DTPA:[6,6]-phenyl-C61-butyric acid methyl ester (PC61BM)/LiF/Al. A power conversion efficiency (PCE) of 1.22% with an open-circuit voltage (VOC) of 0.64?V, a short-circuit current (JSC) of 6.10?mA?cm?2, and a fill factor (FF) of 31.0% was achieved. The PCE is 2.9 times higher than that in the other devices using D2-A-type small molecule TPA-Q-TPA as donor.
- Yu, Junting,Zhu, Weiguo,Tan, Hua,Peng, Qing
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- Syntheses and solar cell applications of conjugated copolymers containing tetrafluorophenylene units
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Novel conjugated copolymers containing tetrafluorophenylene unit have been synthesized and evaluated in bulk heterojunction solar cell. The tetrafluorophenylene unit, as the strong electron deficient moeity, has been applied for the syntheses of donor-acceptor type copolymers with a narrow-band-gap for bulk heterojunction solar cells. DTBT, tetrafluorophenylene and four types of BDT derivatives as the electron rich units were incorporated using Stille polymerization to generate PE-BDTF, PO-BDTF, PE-BDTTF and PO-BDTTF. The introduction of even 1% of tetrafluorophenylene unit substituting DTBT of BDTDTBT type of polymers results in significant decrease of the band gap of the polymers. The device with PO-BDTF:PC71BM (1:1) showed an open-circuit voltage (VOC) of 0.75 V, a short circuit current (JSC) of 11.80 mA/cm2, and a fill factor (FF) of 0.59, which yields PCE of 5.22%.
- Kim, Jinwoo,Kim, Taehyo,Kim, Nam Hee,Kim, Juae,Shim, Joo Young,Kim, Il,Chun, Ho Hwan,Kim, Jin Young,Jin, Jong Sung,Kim, Jong Pil,Jeong, Euh Duck,Suh, Hongsuk
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- Dithienopyrrole-benzodithiophene based donor materials for small molecular BHJSCs: Impact of side chain and annealing treatment on their photovoltaic properties
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Two small molecular organic materials denoted as ICT1 and ICT2 with A-D1-D2-D1-A architecture have been synthesized and their thermal, photo-physical, electrochemical and photovoltaic properties are explored. Synthesized materials have n-butylrhodanine acceptor (A), dithienopyrrole (DTP) (D1) and benzodithiophene (BDT) (D2) (Alkoxy BDT and alkylthiophene BDT, respectively for ICT1 and ICT2) donor moieties. Both the materials have good solubility (up to 25 mg/mL) in most common organic solvents and have excellent thermal stability with the decomposition temperature (Td) as 348 and 382 °C, respectively for ICT1 and ICT2. Both ICT1 and ICT2 have broad and intense visible region absorption (molar excitation coefficient is 1.71 × 105 and 1.65 × 105 mol?1 cm?1, respectively for ICT1 and ICT2) and have suitable HOMO and LUMO energy levels for PC71BM acceptor. Bulk heterojunction solar cells with ITO/PEDOT:PSS/blend/Al structure are fabricated using these materials. The BHJSCs fabricated by spin cast of ICT1:PC71BM and ICT2:PC71BM (1:2 wt ratio) blend from chloroform showed power conversion efficiency (PCE) of 2.77% (Jsc = 6.84 mA/cm2, Voc = 0.92 V and FF = 0.44) and 3.27% (Jsc = 7.26 mA/cm2, Voc = 0.96 V and FF = 0.47), respectively. Annealing the active layer significantly improved the PCE of these BHJSCs to 5.12% (Jsc = 10.15 mA/cm2, Voc = 0.87 V and FF = 0.58) and 5.90% (Jsc = 10.68 mA/cm2, Voc = 0.92 V and FF = 0.60), respectively for ICT1 and ICT2 donors. The enhancement in the PCE is due to higher light harvesting ability of the active layer, better nanoscale morphology for efficient and balanced charge transport and effective exciton dissociation at the donor-acceptor interface.
- Busireddy, Manohar Reddy,Mantena, Venkata Niladri Raju,Chereddy, Narendra Reddy,Shanigaram, Balaiah,Kotamarthi, Bhanuprakash,Biswas, Subhayan,Sharma, Ganesh Datt,Vaidya, Jayathirtha Rao
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- Poly(4,8-bis(2-ethylhexyloxy)benzo1,2-b:4,5-b ldithiophene vinylene): Synthesis, Optical and photovoltaic properties
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A new benzodithiophene (BDT)-based polymer, poly(4,8-bis(2-ethyl hexyloxy )benzo[1,2-b:4,5-b']dithiophene vinylene) (PBDTV), was synthesized by Pd-catalyzed Stille-coupling method. The polymer is soluble in common organic solvents and possesses high thermal stability. PBDTV film shows a broad absorption band covering from 350 nm to 618 nm, strong photoluminescence peaked at 545 nm and high hole mobility of 4.84 χ 10 3 cm 2/Vs. Photovoltaic properties of PBDTV were studied by fabricating the polymer solar cells based on PBDTV as donor and PC70BM as acceptor. With the weight ratio of PBDTV: PC70BM of 1:4 and the active layer thickness of 65 nm, the power conversion efficiency of the device reached 2.63% with Voc = 0.71 V, Zsc,. = 6.46 mA/cm 2, and FF = 0.7 under the illumination of AM1.5, 100 mW/cm 2.
- He, Youjun,Zhou, Yl,Zhao, Guangjin,Min, Jie,Guo, Xia,Zhang,Zhang, Maojie,Zhang, Jing,Li, Yongfang,Zhang, Fenguiig,Inganas, Olle
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- Organic Semiconductor Compound, Organic Thin Film Including the Organic Semiconductor Compound and Electronic Device Including the Organic Thin Film
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Provided is an organic semiconductor compound which is represented by chemical formula 1 or 2. Moreover, provided is an organic thin film containing the same. In the chemical formulas 1 and 2, each substituent is the same as defined in the present specification. According to the present invention, it is possible to reduce production costs for devices.COPYRIGHT KIPO 2018
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Paragraph 0215-0219
(2018/06/07)
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- Hole transporting material for perovskite solar cell and application thereof
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The invention discloses a hole transporting material 2,6-bistriphenylamine-4,8-bis(alkoxy)benzo[1,2-B:4,5-B']dithiophene for a perovskite solar cell. The hole transporting material has simple molecular structures, high hole mobility, high efficiency, high conductivity and good solubility; aromatic functional radicals can be introduced into lateral groups; the perovskite solar cell prepared from the hole transporting material can be matched with the energy level of perovskite. The invention also discloses a preparation method of the hole transporting material. The hole transporting material for the perovskite solar cell is prepared and obtained by using 2,6-dibromo-4,8-bis(alkoxy)benzo[1,2-B:4,5-B']dithiophene and 4-(Diphenylamino)phenylboronicacid as raw materials through a one-step SUZUKI reaction. The preparation method provided by the invention has the characteristics that the operation is simple, the raw materials are low-cost and easily obtained, the separation is easy, and the yield is high.
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Paragraph 0094; 0095; 0096; 0097; 0152; 0153
(2017/07/20)
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- 2,6-bis(triphenylamine)-4,8-bis(alkoxy)benzo[1,2-b:4,5-b']bithiophene and preparation for same
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The invention discloses a hole transport material 2,6-bis(triphenylamine)-4,8-bis(alkoxy)benzo[1,2-b:4,5-b']bithiophene for a perovskite solar cell. The hole transport material has a simple molecular structure, a lateral group to which an aromatic functional group can be introduced, high hole mobility, high efficiency, high electrical conductivity and high dissolubility, and the perovskite solar cell prepared from the hole transport material can be matched with a perovskite energy level. The invention also discloses a preparation method for the hole transport material. The hole transport material for the perovskite solar cell is prepared by an SUZUKI reaction step from raw materials 2,6-dibromo-4,8-bis(alkoxy)benzo[1,2-b:4,5-b']dithiophene and 4-(diphenylamino)phenylboronicacid. The preparation method has the characteristics of simplicity in operation, readily available raw materials, easiness for separation and high yield.
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Paragraph 0095; 0096; 0097; 0098
(2017/07/21)
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- A 2, 1, 3-benzothiadiazole and b thiophene derivatives and its synthetic method
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The invention discloses 2,1,3-benzothiadiazoledithiophene derivatives. The derivatives relate to 5,8-dialkylbisthiophene benzothiadiazole. A preparation method includes preparing in sequence 5,5'-dialkyl-3,3'-bithiophene, 2,7-dialkylbenzodithiophene-4,5-diketone, 2,7-dialkylbenzodithiophene-4,5-dione dioxime, 2,7-dialkyl-4,5-dihydrobenzodithiophene-2,5-diamine, adding dropwise SOCl2 into a mixture of the 2,7-dialkyl-4,5-dihydrobenzodithiophene-2,5-diamine, triethylamine and CH2Cl2, and reacting at room temperature to obtain the 5,8-dialkylbisthiophene benzothiadiazole. The derivatives have good plane regularity, heat stability and good environment adaptability. The derivatives are liable to be processed to membrane, and can be used as intermediates in synthesis for organic solar energy battery materials.
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Paragraph 0052; 0053; 0054; 0055
(2016/10/09)
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- UNIMOLECULAR AND ORGANIC SOLAR CELL COMPRISING THE SAME
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Provided are a single molecule and an organic solar cell including the single molecule. Specifically, the single molecule has an end represented by chemical formula 1 and includes at least two units selected from the group consisting of units represented by chemical formula 2, wherein the two units are the same or different from each other.COPYRIGHT KIPO 2015
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Paragraph 0477-0479
(2016/10/09)
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- HETEROCYCLIC COMPOUND AND ORGANIC SOLAR CELL COMPRISING THE SAME
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The present specification provides a heterocyclic compound and an organic solar cell comprising the same. In addition, the present specification comprises: a first electrode; a second electrode provided opposite to the first electrode; and one or more organic material layers which are provided between the first electrode and the second electrode and include a photoactive layer.COPYRIGHT KIPO 2016
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Paragraph 0475-0478
(2016/11/24)
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- Organic electronic device
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An organic electronic device may include an organic semiconductor compound represented by the following Chemical Formula 1 or Chemical Formula 2. Each substituent of the above Chemical Formulas 1 and 2 may be the same as described in the detailed description.
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Page/Page column 45
(2015/02/18)
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- Novel electro-optic chromophores based on substituted benzo[1,2-b:4,5- b′]dithiophene π-conjugated bridges
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Two novel non-linear optical (NLO) chromophores were designed and synthesized based on the substituted benzo[1,2-b:4,5-b′]dithiophene unit (BDT), tricyanofuran (TCF) electron acceptor and two different electron donors. These new chromophores, which exhibited good thermal stability and solubility in common organic solvents, were systematically characterized by thermogravimetric analysis, UV-Vis spectra, density functional theory (DFT) calculations and measurements of the electro-optic (EO) coefficients. Compared with the dodecyl group in chromophore BDT1 that we have previously reported, the isooctane group in BDT2 could act as a suitable isolation group, and as a result, the guest-host system containing 30% of BDT2 in amorphous polycarbonate (APC) displayed the largest EO coefficient of 102 pm V-1, which was greatly improved over BDT1 and the analogous thiophene-based chromophore with the same electron donor and acceptor. The solvatochromic analysis and DFT study demonstrated that the julolidine group in BDT3 possessed a stronger donating ability. However, the 30% BDT3/APC exhibited an EO coefficient of only 82 pm V-1, which was probably caused by the diminishment of the hyperpolarizability value of BDT3 in the polar polymer matrix. These results indicate the potential of the isooctane-substituted benzo[1,2-b:4,5-b′]dithiophene π-conjugated bridge in chromophore design and NLO materials, and further illustrate the critical role of suitable isolation groups and fine-tuning of the donor's electron-donating strength in optimizing the non-linear properties of NLO chromophores. the Partner Organisations 2014.
- Si, Peng,Liu, Jialei,Deng, Guowei,Huang, Heyan,Xu, Huajun,Bo, Shuhui,Qiu, Ling,Zhen, Zhen,Liu, Xinhou
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p. 25532 - 25539
(2014/07/07)
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- Importance of the Donor:Fullerene intermolecular arrangement for high-efficiency organic photovoltaics
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The performance of organic photovoltaic (OPV) material systems are hypothesized to depend strongly on the intermolecular arrangements at the donor:fullerene interfaces. A review of some of the most efficient polymers utilized in polymer:fullerene PV devices, combined with an analysis of reported polymer donor materials wherein the same conjugated backbone was used with varying alkyl substituents, supports this hypothesis. Specifically, the literature shows that higher-performing donor-acceptor type polymers generally have acceptor moieties that are sterically accessible for interactions with the fullerene derivative, whereas the corresponding donor moieties tend to have branched alkyl substituents that sterically hinder interactions with the fullerene. To further explore the idea that the most beneficial polymer:fullerene arrangement involves the fullerene docking with the acceptor moiety, a family of benzo[1,2-b:4,5-b]dithiophene-thieno[3,4-c]pyrrole-4,6-dione polymers (PBDTTPD derivatives) was synthesized and tested in a variety of PV device types with vastly different aggregation states of the polymer. In agreement with our hypothesis, the PBDTTPD derivative with a more sterically accessible acceptor moiety and a more sterically hindered donor moiety shows the highest performance in bulk-heterojunction, bilayer, and low-polymer concentration PV devices where fullerene derivatives serve as the electron-accepting materials. Furthermore, external quantum efficiency measurements of the charge-transfer state and solid-state two-dimensional (2D) 13C{1H} heteronuclear correlation (HETCOR) NMR analyses support that a specific polymer:fullerene arrangement is present for the highest performing PBDTTPD derivative, in which the fullerene is in closer proximity to the acceptor moiety of the polymer. This work demonstrates that the polymer:fullerene arrangement and resulting intermolecular interactions may be key factors in determining the performance of OPV material systems.
- Graham, Kenneth R.,Cabanetos, Clement,Jahnke, Justin P.,Idso, Matthew N.,El Labban, Abdulrahman,Ngongang Ndjawa, Guy O.,Heumueller, Thomas,Vandewal, Koen,Salleo, Alberto,Chmelka, Bradley F.,Amassian, Aram,Beaujuge, Pierre M.,McGehee, Michael D.
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supporting information
p. 9608 - 9618
(2014/07/22)
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- Effect of extended conjugation on the optoelectronic properties of benzo[1,2-d:4,5-d′]bisoxazole polymers
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Four copolymers comprising benzo[1,2-d:4,5-d']bisoxazole (BBO) and benzo[1,2-b:4,5-b′]dithiophene (BDT) bearing phenylethynyl substituents on either the BBO, BDT moieties or both units were synthesised and the influence of two-dimensional conjugation on their optoelectronic properties investigated. Extending conjugation along the BBO resulted in a 0.5eV decrease in the LUMO level, whereas the HOMO level was raised by 0.2eV. Extending conjugation across the BDT moiety in also resulted in a 0.5eV decrease in the LUMO level, however, the effect was negligible on the HOMO level. Thus, cross-conjugation can be used to independently tune the LUMO level within these systems. CSIRO 2014.
- Tlach, Brian C.,Tomlinson, Aimee L.,Morgan, Kiley D.,Collins, Christopher R.,Zenner, Michael D.,Jeffries-El, Malika
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p. 711 - 721
(2014/06/09)
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- PROCESS FOR PRODUCING FUSED-RING AROMATIC COMPOUND, AND CONJUGATED POLYMER
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The invention addresses a problem of purifying a monomer to be a precursor according to a simpler and milder method so as to obtain a polymer having a higher molecular weight. The invention relates to a method for producing a condensed polycyclic aromatic compound having n active groups (wherein n is an integer of 1 or more and 4 or less), which comprises bringing a composition containing the condensed polycyclic aromatic compound and a solvent into contact with zeolite.
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Paragraph 0239; 0240; 0241; 0257; 0258; 0259; 0260
(2014/09/29)
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- Synthesis and photovoltaic performances of benzo[1,2-b:4,5-b']dithiophene- alt-2,3-diphenylquinoxaline copolymers pending functional groups in phenyl rings
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Two donor/acceptor (D/A)-based benzo[1,2-b:4,5-b′]dithiophene-alt-2, 3-biphenyl quinoxaline copolymers of P1 and P2 were synthesized pending different functional groups (thiophene or triphenylamine) in the 4-positions of phenyl rings. Their thermal, photo
- Tan, Hua,Deng, Xianping,Yu, Junting,Chen, Jianhua,Nie, Kaixuan,Huang, Ying,Liu, Yu,Wang, Yafei,Zhu, Meixiang,Zhu, Weiguo
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p. 1051 - 1057
(2013/08/24)
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- A copolymer based on benzo[1,2-b:4,5-b′]dithiophene and quinoxaline derivative for photovoltaic application
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A D-A-D copolymer (PBDTQx) with a bandgap of 1.78 eV, containing alkoxy-substituted benzo[1,2-b:4,5-b′]dithiophene (BDT) as donor and quinoxaline derivative (Qx) as acceptor, was synthesized by Stille coupling reaction. In order to study the photovoltaic property of PBDTQx, polymer solar cells (PSCs) were fabricated with PBDTQx as the electron donor blended with [6,6]-phenyl-C61-butyric acid methyl ester (PC61BM) as the electron acceptor. The power conversion efficiency (PCE) of PSC was 1.01% for an optimized PBDTQx: PC61BM ratio of 1:5, under the illumination of AM 1.5, 100 mW/cm2. The results indicated that PBDTQx was a promising donor candidate in the application of polymer solar cells.
- Wu, Haimei,Qu, Bo,Cong, Zhiyuan,Liu, Hongli,Tian, Di,Gao, Bowen,An, Zhongwei,Gao, Chao,Xiao, Lixin,Chen, Zhijian,Liu, Huanhuan,Gong, Qihuang,Wei, Wei
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p. 897 - 903
(2012/10/30)
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- SEMICONDUCTING COMPOUNDS AND DEVICES INCORPORATING SAME
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Disclosed are molecular and polymeric compounds having desirable properties as semiconducting materials. Such compounds can exhibit desirable electronic properties and possess processing advantages including solution-processability and/or good stability. Organic transistor and photovoltaic devices incorporating the present compounds as the active layer exhibit good device performance.
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Page/Page column 37;42
(2012/10/08)
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- Low bandgap polymers with benzo [1,2-b:4,5-b′] dithiophene and bisthiophene-dioxopyrrolothiophene units for photovoltaic applications
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New donor/acceptor polymers PBDTTPT1 and PBDTTPT2 with alternating benzodithiophene (BDT) and bisthiophene-dioxopyrrolothiophene (TPT) units were synthesized by Stille coupling reaction. The polymers had optical bandgaps of 1.78 and 1.82 eV, and HOMO energy levels of -5.30 and -5.35 eV for PBDTTPT1 and PBDTTPT2, respectively. Polymeric solar cell devices based on these copolymers as donors and PC71BM as acceptor showed the highest open circuit voltage of 0.95 V and power conversion efficiency of 2.68% under the illumination of AM 1.5, 100 mW/cm2.
- Zhang, Guobing,Fu, Yingying,Xie, Zhiyuan,Zhang, Qing
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experimental part
p. 415 - 421
(2012/01/05)
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- Synthesis and photovoltaic properties of copolymers based on benzo[1,2-b:4,5-b′]dithiophene and thiophene with electron-withdrawing side chains
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Six alternating conjugated copolymers (PL1-PL6) of benzo[1,2-b:4,5- b′]dithiophene (BDT) and thiophene, containing electron-withdrawing oxadiazole (OXD), ester, or alkyl as side chains, were synthesized by Stille coupling reaction. The structures of the polymers were confirmed, and their thermal, optical, electrochemical, and photovoltaic properties were investigated. The introduction of conjugated electron-withdrawing OXD or formate ester side chain benefits to decrease the bandgaps of the polymers and improve the photovoltaic performance due to the low steric hindrance of BDT. Bulk heterojunction polymer solar cells (PSCs) were fabricated based on the blend of the as-synthesized polymers and the fullerene derivative [6,6]-phenyl-C 61-butyric acid methyl ester (PC61BM) in a 1:2 weight ratio. The maximum power conversion efficiency of 2.06% was obtained for PL5-based PSC under the illumination of AM 1.5, 100 mW/cm2.
- Nie, Yujuan,Zhao, Bin,Tang, Peng,Jiang, Peng,Tian, Zongfang,Shen, Ping,Tan, Songting
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experimental part
p. 3604 - 3614
(2012/05/05)
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- Synthesis and characterization of thieno[3,4-b]thiophene-based copolymers bearing 4-substituted phenyl ester pendants: Facile fine-tuning of homo energy levels
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A study was conducted to design and synthesize PTB-based polymers bearing 4-substituted phenyl esters in place of the alkyl esters as the pendants of the thieno[3,4-b]thiophene (TT) unit. It was found that their highest occupied molecular orbital (HOMO) energy levels were readily fine-tuned by changing the substituents on the phenyl groups. Four novel TT monomers bearing various phenyl ester groups (TT1-TT4) were easily prepared in one pot from commercially available phenol derivatives and the key precursor compound, 4,6-dibromothieno[3,4-b]thiophene-2-carboxylic acid, which was synthesized by modified literature procedures. The molecular weights of the obtained polymers were determined by size-exclusion chromatography (SEC) in tetrahydrofuran (THF). The thermal stability of these polymers was investigated by thermal gravimetric analysis (TGA) under a nitrogen atmosphere. The results show that all polymers have good thermal stability with 5% weight loss temperatures (Td) above 300 °C, which is adequate for application in PSC devices.
- Yamamoto, Tomoyuki,Ikai, Tomoyuki,Kuzuba, Mitsuhiro,Kuwabara, Takayuki,Maeda, Katsuhiro,Takahashi, Kohshin,Kanoh, Shigeyoshi
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scheme or table
p. 6659 - 6662
(2012/03/26)
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- Conjugated polymers based on benzodithiophene and arylene imides: Extended absorptions and tunable electrochemical properties
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Three novel conjugated polymers have been designed and synthesized via the alternative copolymerization of the electron-donating monomer benzodithiophene (BDT) and three different electron-accepting monomers: perylene diimide (PDI), naphthalene diimide (NDI), and phthalimide (PhI). All obtained copolymers show good solubility in common organic solvents as well as broader absorptions in visible region and narrower optical band gaps compared to homopolymers from BDT units. It is found that the absorptions of the copolymers are red-shifted with increasing the electron-withdrawing ability of the co-monomer. In particular, the absorption edge of P(BDT-NDI) film extends to 760. nm, whereas that of P(BDT-PhI) film is only at 577. nm. Cyclic voltammograms of the three polymers disclose that P(BDT-PDI) and P(BDT-NDI) are typical n-type materials because PDI and NDI are strong electron-accepting groups, while P(BDT-PhI) is a stable p-type material where the weak electron-withdrawing monomer (PhI) is introduced. The results suggest that the absorption range and the electrochemical properties of the conjugated polymers can be tuned by appropriate molecule-tailoring, which will help exploring ideal conducting polymers for potential applications in polymer optoelectronics, especially in polymer solar cells.
- Chen, Jian,Shi, Min-Min,Hu, Xiao-Lian,Wang, Mang,Chen, Hong-Zheng
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experimental part
p. 2897 - 2902
(2011/11/06)
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- Benzo[1,2-b:4,5-b′]dithiophene-dioxopyrrolothiophen copolymers for high performance solar cells
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New donor/acceptor polymers PBDTDPT1 and PBDTDPT2 with alternating benzodithiophene and N-alkylated dioxopyrrolo-thiophene were synthesized. The new polymers had deep HOMO levels of -5.42 and -5.44 eV for PBDTDPT1 and PBDTDPT2, respectively. A PBDTDPT2 based BHJ solar cell device achieved a PCE of 4.79% and Voc of 0.91 V.
- Zhang, Guobing,Fu, Yingying,Zhang, Qing,Xie, Zhiyuan
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supporting information; experimental part
p. 4997 - 4999
(2010/08/19)
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- Highly efficient solar cell polymers developed via fine-tuning of structural and electronic properties
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This paper describes synthesis and photovoltaic studies of a series of new semiconducting polymers with alternating thieno[3,4-b]thiophene and benzodithiophene units. The physical properties of these polymers were finely tuned to optimize their photovoltaic effect. The substitution of alkoxy side chains to the less electron-donating alkyl chains or introduction of electron-withdrawing fluorine into the polymer backbone reduced the HOMO energy levels of polymers. The structural modifications optimized polymers' spectral coverage of absorption and their hole mobility, as well as miscibility with fulleride, and enhanced polymer solar cell performances. The open circuit voltage, Voc, for polymer solar cells was increased by adjusting polymer energy levels. It was found that films with finely distributed polymer/fulleride interpenetrating networkexhibited improved solar cell conversion efficiency. Efficiency over 6p ercent has been achieved in simple solar cells based on fluorinated PTB4/PC61BM films prepared from mixed solvents. The results proved that polymer solar cells have a bright future.
- Liang, Yongye,Feng, Danqin,Wu, Yue,Tsai, Szu-Ting,Li, Gang,et al.
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experimental part
p. 7792 - 7799
(2009/10/17)
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