- Synthesis and light-emitting properties of new polyfluorene copolymers containing 2,3-diphenylfumaronitrile
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A series of polyfluorene copolymers composed of 9,9-dioctylfluorene (DOF) and 2,3-diphenylfumaronitrile (DPFN), poly(DOF-co-DPFN)s, have been synthesized through a palladium (0)-catalyzed Suzuki coupling reaction, and their light-emitting properties have
- Mi, Dongbo,Kim, Hee Un,Lee, Seon Young,Lee, Jonghee,Hong, Sung-Chul,Pyo, Sungmoon,Hwang, Do-Hoon
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- Deep blue light-emitting polymers with fluorinated backbone for enhanced color purity and efficiency
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Two fluorene-based copolymers (PF-33F and PF-50F) with p-difluorophenylene units in the backbone were synthesized. In comparison with the reference poly(9,9-dioctylfluorene) (PFO), the introduction of p-difluorophenylene units not only increased the fluorescent quantum yields, but also improved the spectra purity and stability of these deep blue emitting copolymers. The famous green emission band at 520 nm from fluorenone defects was never detected for these copolymers even after they were thermal annealed in air at 150 °C. Organic light-emitting diodes were fabricated using them as emitting layer and pure blue electroluminescence was obtained. It was observed that PF-33F based device exhibited much higher current density and brightness than PF-50F and PFO devices. A maximum external quantum efficiency of 1.14% (1.14 cd A-1) and the CIE (0.16, 0.13) were achieved for PF-33F device, which are among the best performance for polyfluorenes reported so far.
- Zhang, Ting,Wang, Renjie,Ren, Huicai,Chen, Zhiguang,Li, Jiuyan
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- Effect of Arylmethylene Substitutions on Molecular Structure, Optoelectronic Properties and Photovoltaic Performance of Dithienocyclopentafluorene-Based Small-Molecule Acceptors
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Two dithienocyclopentafluorene-based small-molecule acceptors (SMAs) were developed that feature methylene-functionalized conjugated side chains, to study the effect of arylmethylene substitution and its number on structure, optoelectronic properties and device performance. Results showed that two SMAs have better absorption properties and planarity, lower bandgaps and higher LUMOs compared with the control SMA without conjugated side chains. The synthesized SMAs were tested in polymer solar cells for examples of their applicability. This work argues that the introduction of methylene-functionalized conjugated side chains has great potential in tuning molecular structure, optoelectronic properties, device physics and photovoltaic performance of SMAs.
- Tang, Xuejiao,Liao, Haitao,Zheng, Tao,Yin, Pan,Cao, Jing,Zeng, Xiaoying,Weng, Chao,Shen, Ping
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- Achieving highly efficient blue light-emitting polymers by incorporating a styrylarylene amine unit
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A series of novel blue light-emitting polymers were designed and synthesized by incorporating a blue styrylarylene amine (DV) chromophore into the backbone of poly(9,9-dioctylfluorene). All the resultant polymers exhibit blue emission peaking at around 46
- Peng, Feng,Zhong, Zhiming,Ma, Yawei,Huang, Zhenqiang,Ying, Lei,Xiong, Jian,Wang, Shirong,Li, Xianggao,Peng, Junbiao,Cao, Yong
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- Tunable Control of the Hydrophilicity and Wettability of Conjugated Polymers by a Postpolymerization Modification Approach
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A facile method to prepare hydrophilic polymers by a postpolymerization nucleophillic aromatic substitution reaction of fluoride on an emissive conjugated polymer (CP) backbone is reported. Quantitative functionalization by a series of monofunctionalized ethylene glycol oligomers, from dimer to hexamer, as well as with high molecular weight polyethylene glycol is demonstrated. The length of the ethylene glycol sidechains is shown to have a direct impact on the surface wettability of the polymer, as well as its solubility in polar solvents. However, the energetics and band gap of the CPs remain essentially constant. This method therefore allows an easy way to modulate the wettability and solubility of CP materials for a diverse series of applications.
- Cong, Shengyu,Creamer, Adam,Fei, Zhuping,Hillman, Sam A. J.,Rapley, Charlotte,Nelson, Jenny,Heeney, Martin
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- Electroluminescent poly(fluorene-co-thiophene-S,S-dioxide): Synthesis, characterisation and structure-property relationships
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A new copolymer, constituted by the regular alternation of a fluorene derivative with a 1,1-dioxothiophene moiety, has been synthesised via Suzuki coupling. The molecular, thermal, structural, and photophysical characterisations have been performed. The material showed two dimensional order, enhanced by annealing; molecular modelling calculations afforded a consistent structural model accounting for the optical data. In comparison with both polyfluorenes and 1,1-dioxothiophene oligomers the unusual photoluminescence quantum yields observed in solution and in the solid state can be related to a significant contribution of internal conversion to the deactivation process in solution, and the formation of intra-chain hydrogen-bonds, due to a peculiar chain conformation, in the solid state. LED devices based on this new copolymer showed the highest efficiency compared with similar copolymers containing both fluorene and 1,1-dioxothiophene functionalities.
- Pasini, Mariacecilia,Destri, Silvia,Porzio, William,Botta, Chiara,Giovanella, Umberto
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- Thieno[3,2-b]thiophene-based conjugated polyfluorene copolymer for efficient polymer solar cell
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We have synthesized and characterized a polyfluorene derivative composed of octyl-substituted thieno[3,2,-b]thiophene and 2,1,3-benzothiadiazole as an acceptor unit. The best power conversion efficiencies of the polymer were showed with 1.63% and 2.31% by using PCBM and PC71BM, respectively. Copyright
- Kim, Joo Yeon,Kim, Hye-Min,Lee, Ja-Eun,Kim, Tae-Dong,Baek, Nam Seob
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- Synthesis and optical and electroluminescent properties of novel conjugated copolymers derived from fluorene and benzoselenadiazole
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A novel series of light-emitting copolymers derived from 9,9-dioctylfluorene (DOF) and 2,1,3-benzoselenadiazole (BSeD) is prepared by means of palladium-catalyzed Suzuki coupling reaction. The feed ratios of DOF to BSeD were 50:50, 85:15, 92:8, and 98:2, respectively. All of the copolymers are soluble in common organic solvents and highly fluorescent in solid state. Devices from such copolymers emit orange-red light with λmax = 570-600 nm. The maximal EL emissions of the devices slightly red-shifted gradually with increasing BSeD's contents. The maximal external quantum efficiency of the polymer light-emitting devices (PLED) reaches 1.0%, which indicates that this new seleno-containing EL polymer based on fluorene and benzoselenadiazole is a promising candidate for fabricating PLEDs.
- Yang, Renqiang,Tian, Renyu,Hou, Qiong,Yang, Wei,Cao, Yong
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- 4-hexylbithieno[3,2-b:2′3′-e]pyridine: An efficient electron-accepting unit in fluorene and indenofluorene copolymers for light-emitting devices
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4-Hexylbithienopyridine has been prepared as a novel electron-accepting monomer for conjugated polymers. To test its electronic properties, alternating copolymers with fluorene and indenofluorene polymers have been prepared. The copolymers displayed reduction potentials about 0.5 V lower than for the corresponding fluorene and indenofluorene homopolymers, indicating much improved electron-accepting properties. Analysis of the microscopic morphology of thin films of the copolymers by AFM shows that they lack the extensive supramolecular order seen with the homopolymers, which is attributed to the bithienopyridine units disrupting the π-stacking. LEDs using these polymers as the emitting layer produce blue-green emission with low turn-on voltages with aluminum electrodes confirming their improved electron affinity. The indenofluorene copolymer displayed an irreversible red shift in emission at high voltages, which is attributed to oxidation of the indenofluorene units. This red shift occurred at higher potentials than for indenofluorene homopolymers in LEDs, suggesting that the heterocyclic moieties offer some protection against electrically promoted oxidation.
- Sonar, Prashant,Zhang, Jingying,Grimsdale, Andrew C.,Müllen, Klaus,Surin, Mathieu,Lazzaroni, Roberto,Leclère, Philippe,Tierney, Steve,Heeney, Martin,McCulloch, Iain
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- High-Efficiency Saturated Red Emitting Polymers Derived from Fluorene and Naphthoselenadiazole
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A variety of novel light-emitting copolymers derived from 9,9-dioctylfluorene (DOF) and 2,1,3-naphthozoselenadiazole (NSeD) were prepared by the palladium-catalyzed Suzuki coupling reaction. The feed ratios of DOF to NSeD were 99.9:0.1, 99.5:0.5, 99:1, 98:2, 95:5, and 85:15. All of the polymers are soluble in common organic solvents and highly fluorescent in solid state. Devices based on the copolymers emit saturated red light, and the emission slightly red-shifted gradually with increasing NSeD's contents. The maximal external quantum efficiency of the polymer light-emitting devices (PLED) reaches 3.1%, and luminous efficiency is greater than 1.0 cd/A with emission maximum at 657 nm and Commission Internationale de L'Eclairage (CIE) coordinates of (0.64, 0.33). This is the highest efficiency with saturated red emission for a single-layer device with nonblend type emitter reported so far in the scientific literature. This indicates that the new EL polymers based on fluorene and naphthoselenadiazole are promising as a red emitter in polymer light-emitting displays.
- Yang, Jian,Jiang, Changyun,Zhang, Yong,Yang, Renqiang,Yang, Wei,Hou, Qiong,Cao, Yong
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- Diastereoselective Radical Oxidative C-H Aminations toward Chiral Atropoisomeric (P, N) Ligand Precursors
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A new class of chiral atropoisomeric (P, N) ligand precursors has been obtained with excellent diastereoselectivities and high yields through diastereoselective metal-free intramolecular radical oxidative C-H amination with chiral phosphamide as the auxil
- Ma, Yan-Na,Cheng, Ming-Xing,Yang, Shang-Dong
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- Synthesis of new conjugated polymers with coordinated praseodymium complexes for polymer memory devices
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A series of novel praseodymium(Pr)-coordinated polymers with fluorene, phthalimide and bipyridine moieties in the main chain were synthesized via a coordination reaction and palladium-catalyzed Suzuki coupling polycondensation. Their structures, optical features and memory performance have been well studied. A resistive switching device with the configuration of ITO/polymer/Al was constructed using a spin-coating process. The device exhibits nonvolatile write-once-read-many-times (WORM) memory behavior. Based on the electrochemical properties and theoretical calculations of the polymers, the effects of the phthalimide moiety and neutral Pr complex on the polymer memory device performance were investigated. Our work offers valuable clues on the development of polymer memory devices.
- Lv, Wei,Liu, Huijiao,Wang, Wen,Yang,Zhen, Hongyu,Ling, Qidan
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- Effective structural modifications enabled by end-capped effects based on fluorene-core donor, with high open-circuit voltage in organic photovoltaic devices
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End-capped effects are important in modifying the structures of donor materials, with the purpose of regulating material properties and achieving high open-circuit voltage (VOC). A series of acceptor-π-donor-π-acceptor (A-π-D-π-A) type small-molecule donor (SMD) materials for bulk-heterojunction (BHJ) organic solar cells with PC71BM as electron acceptor have been designed and synthesized. Three novel small molecules are denoted as flu(3TRD)2, flu(3TCN)2 and flu(3TIN)2, with dioctyl-substituted fluorene as core, 3,3″-dioctyl-2,2':5′,2″-terthiophene as π-bridge, terminated by rhodanine, malononitrile and 1,3-indanedione, respectively. Improvements of photovoltaic performance have been successfully realized via tuning terminal electron-withdrawing units. The power conversion efficiency (PCE) of the devices as-cast prepared from flu(3TRD)2, flu(3TCN)2 and flu(3TIN)2 increases in turn, which is ascribed to incremental optical absorption thereby promoting short-circuit current density (JSC). Particularly, flu(3TCN)2 shows deeper LUMO and HOMO energy levels than flu(3TRD)2 and flu(3TIN)2 due to the strong electron-withdrawing character of malononitrile. As expected, the device as-cast based on flu(3TCN)2 exhibits a reasonable high VOC of 1.07 V. In addition, a satisfactory PCE of 7.06percent has been obtained for flu(3TCN)2 based device with dichloromethane vapor treatment.
- Hu, Chunxiao,Li, Yanqin,Xie, Bao,Yin, Lunxiang
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- Synthesis and optoelectronic properties of novel fluorene-bridged dinuclear cyclometalated iridium (III) complex with A-D-A framework in the single-emissive-layer WOLEDs
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To explore the influence of push-pull chromophores on properties of emitter in organic light-emitting devices (OLEDs), an acceptor-donor-acceptor (A-D-A)-based dinuclear iridium (III) complex of (dfppy)4Ir2(dipic-FL) was synthesized via Suzuki coupling reaction, in which dfppy is 2-(2,4-difluorophenyl)pyridine and dipic-FL is 2,7-di(5-pyridyl-2-carboxyl)- 9,9-dioctyl-9H-fluorene. An intense emission peak at about 480 nm resulting from the (dfppy)2Ir(pic) chromophore and a weak long-wavelength emission band at 580-660 nm attributed to intramolecular charge transfer transition were exhibited for (dfppy)4-Ir2(dipic-FL) in dichloromethane solution. But a remarkably hypsochromic photoluminescence profile with an intense characteristical emission peak at 422 nm was observed, which is attributed to the intraligand (IL) π-πexcited states in its thin film. White emission with a maximum luminance of 1040 cd/m2 and current efficiency of 1.2 cd/A was obtained in its single-emissive-layer (SEL) OLEDs with a configuration of ITO/PEDOT:PSS/ (dfppy)4Ir2(dipic-FL) (10 wt%):TCTA/TPBi/LiF/Al. To our knowledge, this is one of the best examples in term of dinuclear iridium complex as single dopant in the high-performance white-emitting SEL-OLEDs.
- He, Keqi,Wang, Xiangdong,Yu, Junting,Jiang, Haigang,Xie, Guangshan,Tan, Hua,Liu, Yu,Ma, Dongge,Wang, Yafei,Zhu, Weiguo
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- Facile photopatterning of polyfluorene for patterned neuronal networks
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In this paper, we demonstrated a facile photopatterning method that uses photocrosslinkable polyfluorene to fabricate micro-sized photopatterns on transparent indium tin oxide substrate for neuronal patterning. The modified poly(ethyleneimine) (m-PEI) with trimethoxysilane moiety was chemically attached to the hydroxyl group-terminated ITO surface and then the photopatternable polyfluorene derivative was spin coated as a cell-repellent layer onto the m-PEI-coated surface. The well-defined micropatterns were easily created over an entire surface by photocrosslinking of bromoalkyl-substituted polyfluorene (Br-PF) via the radical coupling reaction of a C-Br bond under UV irradiation without an initiator. UV-Vis absorbance, photoluminescence, ATR-FTIR and X-ray photoelectron spectroscopy were used to confirm the photocrosslinking process and the surface composition before and after the photocrosslinking of polyfluorene. The pairing of adhesive m-PEI and repulsive Br-PF effectively guided the neurite outgrowth and controlled neurite extension from individual neurons to the pre-patterned direction with excellent pattern fidelity. Guided neuronal cells were maintained for at least 25 days in vitro without any detachment of neuronal cells during cell culture. A photopatternable polyfluorene derivative in combination with cell-adhesive m-PEI is proved to be an effective way to modify the electrode surface to achieve single cell level neuronal networks.
- Baek, Nam Seob,Kim, Yong Hee,Han, Young Hwan,Lee, Bong Joon,Kim, Tae-Dong,Kim, Sin-Tae,Choi, Young-Seok,Kim, Gook Hwa,Chung, Myung-Ae,Jung, Sang-Don
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- Enhanced three-photon absorption and excited up-conversion fluorescence of phenanthroimidazole derivatives
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Two novel phenanthroimidazole derivatives were synthesized for efficient three-photon excited fluorescence and absorption. By introducing spirobi [9H-fluorene] to replace fluorene, the three-photon-excited fluorescence and cross-section are significantly
- Zhang, Xingye,Cao, Shilin,Huang, Liulian,Chen, Lihui,Ouyang, Xinhua
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- Novel fluorene/trifluoromethylphenylene copolymers: Synthesis, spectra stability and electroluminescence
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A group of novel fluorene-based copolymers were synthesized and characterized. The trifluoromethylphenylene unit was introduced into the copolymer backbone and its content ratio was varied from 10 mol% to 50 mol%. The electronic bandgap of the copolymer increases regularly with increasing trifluoromethylphenylene ratio. In contrast to pure polyfluorene, the deep-blue fluorescence of these copolymers is quite stable and not contaminated by the well-known green emission associated with fluorenone defects. The copolymers were used as an emitting layer to fabricate organic light-emitting diodes with a pure blue electroluminescence with a CIE coordinate y ≤ 0.10 obtained for most copolymers. Whilst the presence of the trifluoromethylphenylene units in the copolymers seemed unfavorable for charge injection and device current, improved spectral purity and stability in both the photoluminescence and electroluminescence were noted and ascribed to the electron-withdrawing nature of the trifluoromethylphenylene units and the enhanced anti-autoxidation ability of the fluorene rings in these copolymers.
- Zhang, Ting,Deng, Lijun,Wang, Renjie,Zhou, Wei,Li, Jiuyan
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- Synthesis and characterization of fluorene and cyclopentadithiophene-based copolymers exhibiting broad absorption for photovoltaic devices
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In this study, two low bandgap copolymers composed of fluorene (Fl), cyclopentadithiophene (CDT), and 4,7-bis(2-thienyl)-2,1,3-benzothiadiazole (DBT) were synthesized, and their optical, electrochemical, and photovoltaic (PV) characteristics were investigated for applications in PV devices. The feed ratio of the Fl and CDT moieties was modulated to tune the electronic structures and resulting optical properties of the polymers. In the copolymeric structures, the Fl-CDT unit absorbs the short-wavelength UV/vis regions, and the CDT-DBT (or Fl-DBT) unit with strong intramolecular charge transfer characteristics covers the long-wavelength visible regions. P1 exhibited a wide UV absorption spectrum covering the UV and entire visible region in the range of 300-800 nm, and P2 showed absorption covering from 300 to 700 nm. UV/vis and electrochemical studies confirmed the desirable highest occupied molecular orbital/lowest unoccupied molecular orbital levels of the copolymers with bandgaps of 1.62-1.86 eV, enabling efficient electron transfer and a high open-circuit voltage when blending them with fullerene derivatives. When the polymers were blended with [6,6]phenyl-C61-butyric acid methyl ester, P1 exhibited the best device performance with an open-circuit voltage of 0.66 V, short-circuit current of 4.92 mA cm-2, and power conversion efficiency of 1.13% under Air Mass 1.5 Global (AM 1.5G, 100 mW cm-2) illumination.
- Jung, In Hwan,Kim, Sun Hee,Jeong, Eunjae,Yang, Renqiang,Lee, Kwanghee,Woo, Han Young,Shim, Hong-Ku
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- Synthesis and luminescent properties of fluorene copolymers bearing DCM pendants
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A series of copolymers, poly[(9,9-dioctylfluorene-2,7-diyl) -co-(4-dicyanomethylene-2-methyl-6-[4-(diphenylamino)styryl]-4H-pyran-4′, 4″-diyl], were synthesized by polymerizing 2,7-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9,9-dioctylfluorene with mixtures of 2,7-dibromo-9,9-dioctylfluorene and 4-dicyanomethylene-2-methyl-6-[bis(4′-bromophenyl)amino]styryl]-4H-pyran (a DCM derivative) by the palladium-catalyzed Suzuki coupling reaction. The copolymers were characterized by molecular weight determination, elemental analysis, 1H NMR, FT-IR spectroscopy, DSC, TGA, UV-vis spectroscopy, and photoluminescence (PL) and electroluminescence (EL) spectroscopy. The copolymers showed two absorption peaks at 380 and 485 nm, and the long-wavelength absorption increased with increasing the fraction of the DCM comonomer. The PL spectra of copolymers in chloroform solution displayed emission from both the main chain (420 nm) and DCM units (620 nm). In the solid state, however, PL spectra of copolymers showed only the long wavelength red emission at 620 nm with no trace of emission from the main chain, which implies a facile exciton migration or energy transfer to the lower energy sites from the fluorene part to the DCM part. This results in emission of only the red light originating from the latter segments. A study on time-resolved PL rise and decay of the polymers clearly supports the energy transfer mechanism. Light-emitting diode (LED) devices were fabricated to have the configuration of ITO (indiumtin oxide)/PEDOT/polymer/Li:Al alloy. EL spectra of the devices showed only red emissions as observed in the PL spectra of the polymers' thin films. EL efficiency decreased with increasing DCM contents. When a tris(8-hydroxyquinolinato)aluminum (Alq3) layer was inserted between the emitting polymer layer and the cathode to make the ITO/PEDOT/polymer/Alq3/Li:Al alloy configuration, the device efficiencies became much higher (~10-2%) than those (5 × 10-5-5 × 10-3%) of single-layer devices.
- Cheon, Cheol Hong,Joo, Sung-Hoon,Kim, Kyungkon,Jin, Jung-Il,Shin, Hee-Won,Kim, Yong-Rok
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- Synthesis and characterization of a new light-emitting fluorene-thieno[3,2-b]thiophene-based conjugated copolymer
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A new alternating polyfluorene copolymer, poly(9,9′-dioctylfluorene-alt-thieno[3,2-b]thiophene)(PFTT), containing a thiophene-condensed thieno[3,2-b]thiophene moiety has been synthesized via a palladium-catalyzed Suzuki coupling reaction. The synthesized polymer was successfully characterized by 1H NMR, 13C NMR, and elemental analysis. It shows good thermal stability and displays unique phase transition behavior between the crystalline and liquid-crystalline states. The ionization potential and electron affinity of PFTT are -5.38 eV and -2.40 eV, respectively, as determined by cyclic voltammetry. Thus, PFTT has an electrochemical band gap of approximately 2.98 eV, which is smaller than that of common polyfluorene (PF) homopolymers. As a film, PFTT exhibits UV-vis and photoluminescence maxima at 471 and 511 nm, respectively. A light-emitting diode device fabricated with an ITO/PEDOT/PFTT/LiF/Al configuration exhibits pure green light emission with the full width at half-maximum (fwhm) of only 57 nm and a low turn-on voltage of 3.3 V. Especially, this emission has the CIE coordinates (0.29, 0.63), which are very close to the standard for green used by the National Television System Committee. In addition, PFTT exhibits better electroluminescence performance than other similar PF homopolymers and than fluorene- and thiophene-based copolymers.
- Lim, Eunhee,Jung, Byung-Jun,Shim, Hong-Ku
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- Substituent effects on fluorene-based linear supramolecular polymerizsation
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Two supramolecular systems were constructed based on fluorene-based π-conjugated monomers with or without spiro structures, respectively, and their self-assemble behaviour and optical properties were investigated. Concentration-dependent 1H NMR
- Zhang, Guang-Wei,Luo, Meng-Cheng,Lei, Jia-Qi,Zhong, Tao-Tao,Wei, Ying,Xie, Ling-Hai,Huang, Wei
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- Novel base-dopable poly(2,7-fluorenylene) derivatives
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A novel acidic poly(fluorenylene) derivative has been synthesized which, upon base-doping, shows electrical conductivities of 10-6-10-5 S cm-1; this new doping method for conjugated polymers opens the way to the preparation of air-stable n-type conducting polymers.
- Ranger, Maxime,Leclerc, Mario
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- MATERIALS FOR ORGANIC ELECTROLUMINESCENT DEVICES
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The present invention relates to compounds of the formulae (1) to (4), which are suitable for use in electronic devices, in particular organic electroluminescent devices, to intermediate compounds for the compounds or formulae (1) to (4) and to electronic devices, which comprise the compounds of formulae (1) to (4).
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Paragraph 0153; 0154; 0157; 0158
(2021/11/26)
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- A novel boron ketoiminate-based conjugated polymer with large Stokes shift: AIEE feature and cell imaging application
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AIE/AIEE-active conjugated polymers have shown great potential in bioimaging applications. However, the absorption of many AIE/AIEE polymers poorly matches with the laser excitation used in confocal imaging, which may greatly affect the imaging quality. I
- Dai, Chunhui,Yang, Dongliang,Hu, Yanling,Deng, Yue,Yang, Xiaoman,Liu, Zhonglin
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p. 4071 - 4076
(2021/03/08)
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- 1,2,3-Triazolyl functionalized thiophene, carbazole and fluorene based A-: Alt -B type π-conjugated copolymers for the sensitive and selective detection of aqueous and vapor phase nitroaromatics (NACs)
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A series of highly emissive π-conjugated A-alt-B type copolymers (P1-P3) appended with a 1,2,3-triazole moiety was synthesized via Suzuki polymerization. The well-defined and soluble π-conjugated copolymers were characterized via multinuclear NMR spectroscopy and tetradetector GPC studies, showing a molecular weight (Mn) in the range of 16.4-20.1 kDa with a polydispersity index in the range of 1.25-1.42. The synthesized emissive π-conjugated polymer probes were explored as fluorescent chemosensors for nitroaromatic compounds (NACs) in solution, vapor and contact mode. Detailed photophysical and sensing studies were performed to understand the polymer-NAC interaction, inducing the selective fluorescence quenching of the π-conjugated polymer probes through the photoinduced electron transfer (PET) mechanism. All the polymeric probes (P1-P3) were highly reversible in nature with NACs, and thus could be reused multiple times. The limit of detection of the probes towards nitroaromatics was found to be in the range of 120-200 ppb with a high association constant in the order of 104 M-1. Furthermore, test paper kits were also fabricated, which allowed the trace detection of picric acid by the naked eye, making it a practical means for the quick, easy and inexpensive on-site detection of NAC-based explosives.
- Giri, Dipanjan,Patra, Sanjib K.
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supporting information
p. 14469 - 14480
(2020/11/09)
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- Bipolar micromolecule luminescent material processed by using environment-friendly solvent as nucleus and preparation method and application thereof
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The invention discloses a bipolar small molecular luminescent material capable of being processed by adopting an environment-friendly solvent and taking a naphtho-indenofluorene unit as a core as well as a production method and application of the bipolar small molecular luminescent material. The production method comprises the following steps: by taking the naphtho-indenofluorene unit containing a polar substituent group as the core; carrying out a Suzuki coupling reaction, and connecting an electron donor unit and an electron withdrawing unit onto two sides of the naphtho-indenofluorene unit in sequence, so as to obtain the bipolar small molecular luminescent material taking the naphtho-indenofluorene unit as the core. The bipolar small molecular luminescent material taking the naphtho-indenofluorene unit as the core, disclosed by the invention, has good solubility, film forming property and thin film form stability in the environment-friendly solvent; a luminescent layer produced by the luminescent material can avoid a mixing phenomenon with a hole/electron transmission layer interface; the prepared luminescent layer does not need to be subjected to annealing treatment when being used for preparing a luminescent device, so that a preparation process is simple.
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Paragraph 0094; 0098-0099
(2020/05/08)
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- Isomeric effect of fluorene-based fused-ring electron acceptors to achieve high-efficiency organic solar cells
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Acceptor-donor-acceptor (A-D-A) non-fullerene electron acceptors (NFEAs) using ladder-type donor structures have become the dominant n-type materials for achieving high-efficiency OSCs. In this work, two isomeric fluorene-based ladder-type structures FCTT (TT-C-F-C-TT) and FTCT (T-C-TFT-C-T) have been designed and synthesized. These two isomeric donors with the different fused-ring arrangement, molecular geometry, and side-chain placement were end-capped with the FIC acceptors to form two NFEAs FCTT-FIC and FTCT-FIC isomeric materials. Compared to FTCT-FIC using the thiophene (T)-terminal donor, FCTT-FIC with the thienothiophene (TT)-terminal donor has more evenly distributed side chains on both sides of the backbone and less steric hindrance near the FIC acceptors, which enables stronger antiparallel π-π packing among the end-groups to create a channel for efficient electron transport, as evidenced by the thin-film GIWAXS measurements. FCTT-FIC displayed a larger optical bandgap and deeper-lying energy levels than its FTCT-FIC isomer. Compared to the PBDB-T:FTCT-FIC device, the PBDB-T:FCTT-FIC device showed a higher PCE of 10.32% with an enhanced Jsc of 19.63 mA cm-2 and an FF of 69.14%. A PM6:FCTT-FIC device using PM6 as a p-type polymer achieved the highest PCE of 12.23%. By introducing PC71BM as the second acceptor to enhance the absorption at shorter wavelengths, optimize the morphology and facilitate electron transport, the ternary-blend PM6:FCTT-FIC:PC71BM (1 : 1 : 0.5 in wt%) device yielded the highest PCE of 13.37% with a Voc of 0.92 V, a higher Jsc of 19.86 mA cm-2, and an FF of 73.2%. This result demonstrated that the TT-terminal ladder-type donor is generally a better molecular design than the corresponding T-terminal ladder-type isomer for the development of new A-D-A NFEAs.
- Cao, Fong-Yi,Cheng, Yen-Ju,Huang, Po-Kai,Su, Yen-Chen,Xue, Yung-Jing
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supporting information
p. 5315 - 5322
(2020/03/19)
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- NITROGENOUS CYCLIC COMPOUND AND COLOR CHANGING FILM COMPRISING SAME
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The present specification relates to a compound containing nitrogen, and a color conversion film, a backlight unit, and a display device, including the same.
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Paragraph 0120-0121 0210-0211
(2020/04/10)
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- A-pi-D-pi-A type small molecule solar cell receptor material based on thiophene indenone and fluorene and preparation method of A-pi-D-pi-A type small molecule solar cell receptor material
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The invention discloses an A-pi-D-pi-A type small molecule solar cell receptor material based on thiophene indenone and fluorene and a preparation method of the A-pi-D-pi-A type small molecule solar cell receptor material. According to the receptor material, fluorine is adopted as a central core structure, groups such as thiophene, furan and benzene are adopted as pi bridges, and aldehyde groups at both ends are subjected to a condensation reaction with active sites of an electrondrawing group thiophene indanone to obtain symmetric target molecules at normal temperature and normal pressure. The A-pi-D-pi-A type small molecule solar cell receptor material based on thiophene indenone and fluorine is simple in synthesis method, easy in reaction condition control, high in yield, good in universal applicability and possible in efficient synthesis, can be widely applied to fields such as energy, life, analysis, material science, and the like, and is particularly suitable for being used as organic small molecule solar cell receptor materials, and the like.
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Paragraph 0053-0054
(2020/03/06)
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- PADAP derivative, and preparation method and application thereof
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The invention provides a PADAP derivative. The PADAP derivative is as shown in a formula (I) which is described in the specification. In the formula (I), X is halogen; and R1 and R2 are respectively and independently selected from the group consisting of
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Paragraph 0024; 0060-0061
(2020/07/13)
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- Double-(S, S - dioxo - dibenzo thiophene) and high output compound and its preparation method and application
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The invention discloses a bi(S,S-dioxo-dibenzothiophene) five-membered ring compound and a preparation method and application thereof. The existence of bi-sulfuryl in the bi(S,S-dioxo-dibenzothiophene) five-membered ring compound is more beneficial for improving the electron affinity of molecules. Alkyl chains are introduced on a five-membered ring, so that the solubility of monomers in an organic solvent can be obviously improved. The plane conjugacy of the compound is better, and is beneficial for the transmission of a current carrier. Higher D-A mutual effect existing in the molecules of the compound endows higher fluorescence of the material. The bi(S,S-dioxo-dibenzothiophene) five-membered ring compound is synthesized and obtained through common organic chemistry reactions such as substitution reactions, Suzuki coupling and ring-closure reactions and oxidation reactions. The compound has good solubility in the organic solvent, and is suitable for solution processing. The compound has wide application prospects in the fields of organic luminescence display, organic photovoltaic cells and organic field-effect tubes.
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Paragraph 0035-0037; 0040
(2019/06/26)
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- Can adopt the environment friendly solvent processing in order to alkyl Philippine unit as the nuclear double-polar small molecular light-emitting material and its preparation method and application
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The invention discloses a bipolar small-molecular luminescent material capable of being processed with an environment-friendly solvent and adopting an alkyl phenanthrene unit as a core as well as a preparation method and an application of the bipolar smal
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Paragraph 0071-0072; 0075-0076
(2019/05/28)
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- SEMICONDUCTING COMPOSITIONS COMPRISING SEMICONDUCTING POLYMERS
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A semiconducting composition comprising a semiconducting polymer and a semiconducting non-polymeric polycyclic compound, wherein the semiconducting polymer comprises units of A and/or B: wherein R1, R2, R5, R6, R7, R8, x, y, p, q, r, R3, R4, R9, R10 and R11 have any of the meanings defined in the description.
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Paragraph 0553-0556
(2019/05/15)
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- Bipolar small-molecule luminescent material taking diphenanthro indene fluorene units as cores, and preparation method and application of material
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The invention discloses a bipolar small-molecule luminescent material taking diphenanthro indene fluorene units as cores, and a preparation method and application of the material. According to the invention, diphenanthro indene fluorene units containing substituent groups are used as cores, an electron donor unit and an electron acceptor unit are connected to the two sides of each diphenanthro indene fluorene unit containing substituent groups through a Suzuki coupling reaction, and therefore the bipolar small-molecule luminescent material taking diphenanthro indene fluorene units as cores isobtained. The material provided the invention has a simple synthesis method, is easy to purify, and is beneficial for industrial application. The bipolar small-molecule luminescent material has good solubility, film-forming property and film morphologic stability, and the luminescent layer based on the bipolar small-molecule luminescent material does not need annealing treatment when devices are prepared, so that the preparation process is simple.
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Paragraph 0052-0056
(2018/03/26)
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- Highly Luminescent Encapsulated Narrow Bandgap Polymers Based on Diketopyrrolopyrrole
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We present the synthesis and characterization of a series of encapsulated diketopyrrolopyrrole red-emitting conjugated polymers. The novel materials display extremely high fluorescence quantum yields in both solution (>70%) and thin film (>20%). Both the absorption and emission spectra show clearer, more defined features compared to their naked counterparts demonstrating the suppression of inter and intramolecular aggregation. We find that the encapsulation results in decreased energetic disorder and a dramatic increase in backbone colinearity as evidenced by scanning tunnelling microscopy. This study paves the way for diketopyrrolopyrrole to be used in emissive solid state applications and demonstrates a novel method to reduce structural disorder in conjugated polymers.
- Leventis, Anastasia,Royakkers, Jeroen,Rapidis, Alexandros G.,Goodeal, Niall,Corpinot, Merina K.,Frost, Jarvist M.,Bu?ar, Dejan-Kre?imir,Blunt, Matthew Oliver,Cacialli, Franco,Bronstein, Hugo
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supporting information
p. 1622 - 1626
(2018/02/17)
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- Luminescent material with naphthoindene carbazole unit containing polar substituent, and preparation and application of luminescent material
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The invention belongs to the technical field of organic photoelectricity and discloses a luminescent material with a naphthoindene carbazole unit containing a polar substituent, and a preparation andapplication of the luminescent material. The luminescent material has a structure shown in the description. The luminescent material taking the naphthoindene carbazole unit containing the polar substituent as the center is obtained by taking the naphthoindene carbazole unit containing the polar substituent as a core and selecting a unit having an electron-transport property. The naphthoindene carbazole unit has strong chemical stability and chemical modification performance, and can undergo a variety of chemical reactions. The presence of lone pair electrons on a nitrogen atom, gives the naphthoindene carbazole unit better hole injection and transport properties. The naphthoindene carbazole unit is good in flatness, has high fluorescence quantum efficiency, and is conducive to improve thephotoelectric properties of the material. The luminescent material can be dissolved in polar solvents such as methanol, DMF, DMSO and water. The luminescent material prepared by the invention can be used to prepare a light-emitting layer of a light-emitting diode by a solution processing technology such as spin coating, ink-jet printing or printing film forming.
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- Design and synthesis of N-substituted perylene diimide based low band gap polymers for organic solar cell applications
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In this study, we report on the synthesis and device studies of a series of new copolymers containing N-substituted perylene dimide and dioctylfluorene units as part of the main backbone. A facile synthetic approach avoiding non-selective bromination was used to synthesize the monomer M1 by the reaction of perylene-3,4,9,10-tetracarboxylic dianhydride with 2-amino-7-bromo-9,9-dioctylfluorene. The copolymers P1 and P2 were synthesized by Suzuki polycondensation of M1 with 2,2′-(9,9-dioctyl-9H-fluoren-2,7-diyl)bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolane) M2 and 9-(heptadecan-9-yl)-2,7-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-carbazole M3, respectively. The copolymer P3 was synthesized by direct arylation polymerization of M1 with 4,7-bis(4-octylthiophen-2-yl)benzo[c]-1,2,5-thiadiazole M4. All the copolymers showed thermal stability greater than 380 °C as evidenced from thermogravimetric analysis. The copolymers exhibited a narrow optical band gap (1.80-2.08 eV) with their UV-visible absorption spectra extending up to the NIR region and they are found to be suitable for use in OSC applications. The molecular weights of the polymers P1-P3 were found to be in the range of 10.68 to 16.02 kg mol-1 as measured from GPC analysis. The surface morphology of the active layers based on P1/P2/P3:P3HT blend films was investigated by AFM and the rms values from height images range from 0.65 to 2.90 nm. The polymers were blended with P3HT to fabricate BHJ solar cells in three different weight ratios i.e. 1 : 1, 1.5 : 1 and 2 : 1 and the best power conversion efficiency was observed for the binary film of P3:P3HT blend device in a 1 : 1 weight ratio which reached up to 1.96% with a Voc of 0.55 V, Jsc of 10.12 mA cm-2 and FF of 34.63% which is among the highest reported for BHJ solar cells with N-substituted PDI based acceptors.
- Meena, Savita,Mohammad, Tauheed,Dutta, Viresh,Jacob, Josemon
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p. 30468 - 30480
(2018/09/11)
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- Phenyl-bridged and carboxyl-terminated A1-pi-A-D-A-pi-A1 type BT derivative and preparation method thereof
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The invention discloses a phenyl-bridged and carboxyl-terminated A1-pi-A-D-A-pi-A1 type BT derivative and a preparation method thereof. The preparation method of the phenyl-bridged and carboxyl-terminated A1-pi-A-D-A-pi-A1 type BT derivative comprises the
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- Dialkyl-substituted naphtho-dioxodibenzothiophene monomer and preparation method thereof and polymer containing dialkyl-substituted naphtho-dioxodibenzothiophene unit and application of polymer
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The invention discloses a dialkyl-substituted naphtho-dioxodibenzothiophene monomer and a preparation method thereof and a polymer containing a dialkyl-substituted naphtho-dioxodibenzothiophene unit and the application of the polymer. A high-absorption electron unit -SO2- exists in the dialkyl-substituted naphtho-dioxodibenzothiophene monomer, and thus the electron affinity of a molecule can be improved. Through introducing of an unsymmetrical substituting condensed ring structure and an alkyl group, the electron affinity of the monomer can be lowered, and meanwhile, solubleness of the monomer in organic solvent is improved greatly. The dialkyl-substituted naphtho-dioxodibenzothiophene monomer obtains a homopolymer or a copolymer containing the dialkyl-substituted naphtho-dioxodibenzothiophene unit through Suzuki or Stille or Yamamoto polymerization reaction, and the obtained polymer has good solubleness in the organic solvent, is suitable for solution processing, and has wide application prospects in preparation of electroluminescent devices, organic solar cells and organic field effect transistors.
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Paragraph 0053; 0054; 0055; 0056
(2017/08/28)
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- Blue oligomer based on dibenzothiophene-S,S-dioxide unit and preparation method and application of blue oligomer
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The invention discloses a blue oligomer based on a dibenzothiophene-S,S-dioxide unit and a preparation method and application of the blue oligomer. The blue oligomer is mainly characterized by comprising a fluorene structure unit and the dibenzothiophene-S,S-dioxide structure unit. The preparation method mainly comprises the step of preparation of the blue oligomer based on the dibenzothiophene-S,S-dioxide unit. Due to the fact that the electroluminescence efficiency and the spectral stability are improved by introducing the dibenzothiophene-S,S-dioxide structure unit into the oligomer, the novel oligomer blue-light emitting material is obtained. According to the obtained blue oligomer based on the dibenzothiophene-S,S-dioxide unit, an electroluminescence device prepared through film formation of a solution processing method is high in efficiency, good in spectral stability and suitable for being adopted as a light-emitting layer of a light-emitting diode and a flat-panel displayer.
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Paragraph 0053; 0054; 0055; 0056
(2017/03/08)
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- Bipolar luminescent material being processable in environment-friendly solvent and having alkyl phenanthroline unit as core, and preparation method and application thereof
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The invention discloses a bipolar luminescent material which is processable in an environment-friendly solvent and has an alkyl phenanthroline unit as a core, and a preparation method and an application thereof. The bipolar luminescent material herein is
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Paragraph 0080; 0084-0085
(2017/09/01)
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- The invention relates to a heterocyclic aryl and yinyin wu unit as the nuclear double-polar small molecular light-emitting material preparation method and application (by machine translation)
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The invention discloses a to aryl heterocyclic and yinyin wu unit as the nuclear double-polar small molecular light-emitting material and its preparation method and application. The invention through the Suzuki coupling reaction of preparing the aryl hete
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Paragraph 0048; 0049; 0050; 0051
(2017/07/20)
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- Bipolar micromolecular luminescent material taking naphthalene diindenofluorene cell as core, and preparation method and application of bipolar micromolecular luminescent material
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The invention discloses a bipolar micromolecular luminescent material taking a naphthalene diindenofluorene cell as a core, and a preparation method and application of the bipolar micromolecular luminescent material. The naphthalene diindenofluorene cell
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Paragraph 0055; 0056; 0057; 0058; 0059
(2017/07/19)
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- Bipolar small molecular luminescent material taking diphenanthro-2,8-indene fluorine unit as core as well as preparation method and application thereof
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The invention discloses a bipolar small molecular luminescent material taking a diphenanthro-2,8-indene fluorine unit as a core as well as a preparation method and application thereof. The preparation method comprises the following steps: by taking diphen
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Paragraph 0055-0059
(2017/10/07)
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- Double-S, S - dioxo - dibenzo thiophene and five-membered ring monomer and its preparation method and polymer
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The invention discloses a bis S,S-dioxo-dibenzothiophene five-membered ring monomer, a preparation method thereof and a polymer. Due to a bis sulfonyl group in the bis S,S-dioxo-dibenzothiophene five-membered ring, the electron affinity of molecules can be improved more easily. By introducing an alkyl chain to the five-membered ring, the solubility of the monomer in organic solvent can be significantly improved, and meanwhile the steric hindrance influence on polymerization reaction from the position of the alkyl chain can be avoided. Due to a large conjugate plane, the cavitation and electron transmission performance of the polymer can be improved. Through Suzuki or Stille or Yamamotor polymerization reaction of the bis S,S-dioxo-dibenzothiophene five-membered ring monomer, a homopolymer or copolymer can be obtained. The polymer of the series has good solubility in organic solvent and is suitable for solution processing. The bis S,S-dioxo-dibenzothiophene five-membered ring monomer has broad application prospects in the fields of organic light-emitting display, organic photovoltaic cells and organic field effect transistors.
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Paragraph 0082; 0084; 0087
(2018/01/11)
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- Can adopt the environment friendly solvent processing in order to Spirofluorene unit as the nuclear double-polar small molecular light-emitting material and its preparation method and application (by machine translation)
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The present invention discloses the use of environmental friendly solvent processing of Spirofluorene unit as the nuclear to double-polar small molecular light-emitting material and its preparation method and application. The invention relates to a nuclear Spirofluorene unit, by Suzuki coupling reaction, the electron withdrawing unit and connected to the electronic unit in the two sides of the Spirofluorene unit, can be prepared by solvent processing of environment-friendly to Spirofluorene unit as the nuclear double-polar small molecular light-emitting material. The invention of Spirofluorene unit as the nuclear to double-polar small molecular light-emitting material in the environment friendly solvent with good solubility, film-forming property and thin membrane shape stability, while at the same time has good electron and hole transmission performance, can balance the carrier injection with the transmission, so that the more electron and hole effectively composite generating excitons, based on the material of the light-emitting layer can be avoided between the hole/electron transport layer interface mixing phenomenon, thereby improving the efficiency of the light emitting device, and in the preparation of electroluminescent device is not required for the annealing treatment, so that the simple preparation process. (by machine translation)
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Paragraph 0060; 0061
(2017/09/01)
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- Naphthoindenofluorene unit-containing micromolecule luminescent material processed through eco-friendly solvent and its preparation method and use
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The invention discloses a naphthoindenofluorene unit-containing micromolecule luminescent material processed through an eco-friendly solvent and its preparation method and use. The micromolecule luminescent material utilizes naphthoindenofluorene as a core unit. Through use of a group with an electron transmission unit, a micromolecule material with naphthoindenofluorene as a core is obtained. The naphthoindenofluorene unit-containing micromolecule luminescent material can be processed through an eco-friendly solvent. The prepared micromolecule material can be used for preparation of an organic light-emitting diode luminescent layer.
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Paragraph 0084; 0085
(2017/01/19)
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- Fluorene derivative and use thereof
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Provided is the fluorene derivative represented in formula (1). (In the formula, R1 and/or R2 represents an alkoxy group, an alkenyloxy group, an alkynyloxy group, an aryloxy group, a heteroaryloxy group or an alkyl group that includes at least one ether structure, R3 and R4 represent a prescribed substituent, n1 and n2 are integers 0-3, and Ar1 and Ar2 represent a prescribed nitrogen-containing group.)
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Paragraph 0120; 0125; 0126
(2016/11/21)
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- Bridged bis-boron-dipyrromethene (BODIPY) derivative containing fluorene at meso-position and preparation method thereof
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The invention discloses a bridged double-center BODIPY derivative containing fluorene at a meso-position and a preparation method thereof. The preparation method comprises the following steps: synthesizing a symmetric dialdehyde compound containing bridging groups consisting of benzene, thiophene and furan and different substituent groups like a butyl group and an octyl group; then subjecting the symmetric dialdehyde compound and pyrrole to a reaction under the catalysis of indium trichloride so as to synthesize a bis(dipyrrolidine) compound; and successively carrying out oxidation by chloranil and fluoroboronation by boron trifluoride ether so as to obtain a fluorene-containing different bridging group-substituted BODIPY dye which has a structural general formula as shown in a formula I that is described in the specification. According to the invention, fluorene and the bridging groups consisting of benzene, thiophene and furan are introduced for the first time and conventional synthetic methods are improved, so the obtained double-center BODIPY dye has stable spectral absorption; and introduction of thiophene, furan and fluorene enables the fluorescence emission peak of the derivative presents obvious red shift, and fluorescence effect is enhanced with enhancement of system conjugative effect. The organic dye can be efficiently synthesized and widely used in fields like life science, analytical chemistry and environmental energy.
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- organic semiconductor compound, manufacturing method thereof, and organic electronic device that contains it
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The present invention relates to an organic semiconductor compound, a method for manufacturing the same, and an organic electronic device comprising the same and, more specifically, to an organic semiconductor compound including quinoxaline, a method for manufacturing the same, and an organic electronic device comprising the same. In addition, by having a low band gap by synthesizing and copolymerizing a thiophene derivative containing sulfur (S) with a quinoxaline-based compound, the organic electronic device comprising the same has a higher efficiency with an innovative combination with a fullerene derivative, which is a photoactive layer, with the organic semiconductor compound of the present invention. The organic semiconductor compound of the present invention has high thermal stability and high solubility and the organic electronic device comprising the same has excellent electric characteristics, thereby can be valuably used as a n-type material of the organic electronic device, especially an organic solar cell or an organic thin film transistor.
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Paragraph 0152; 0159-0160
(2016/10/09)
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- Synthesis of fluorene-based di-BODIPY dyes containing different aromatic linkers and their properties
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Three novel fluorene-based symmetric di-BODIPY dyes (BDPa-c) featuring a fluorene motif as the central core, BODIPY as the terminal groups, and several types of aromatic groups, including phenyl, thiophene, and furan, as linkers were synthesized. The optical and electrochemical properties of these BODIPY dyes were investigated, and DFT theoretical calculations were performed. All these dyes show absorption bands in the region of 300-650 nm with high extinction coefficients. Furan-linked dye BDPc exhibit a more coplanar molecular structure, which increases the efficient π-conjugation length and causes intensive intramolecular charge transfer (ICT), resulting in broadened and red-shifted absorption bands. The luminescence of these dyes is located in near-infrared regions with large Stokes shifts (1013-4862 cm-1). The HOMO/LUMO energy levels, as investigated by CV are approximately 5.5 eV and 3.6 eV, respectively.
- Zhao, Hongbin,Liao, Junxu,Peng, Min,Wang, Yucai,Zhou, Weinan,Li, Bohong,Shen, Songping,Xie, Zechuan
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p. 7145 - 7149
(2015/12/12)
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- Fluorene copolymer, method for preparation and use thereof
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A fluorene copolymer, method for preparation thereof, and use thereof are provided. Said fluorene copolymer comprises copolymer represented by formula (I), wherein R1-R2, R5-R8 are selected from H or C1-C20 alkyl, R3-R4 are selected from H, C1-C20 alkyl, C1-C20 alkoxyl, phenyl or phenoxyl, x+y=1, x≠0, y≠0; n is an integer of 1 to 200, Ar1 is thiophene unit-containing group. On account of thiophene unit and thienopyrazine unit, the fluorene copolymer has wide spectrum response range and favorable stability.
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Page/Page column 18
(2014/07/22)
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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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p. 6038 - 6042
(2014/12/09)
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- Synthesis and optoelectronic properties of novel fluorene-bridged dinuclear cyclometalated iridium (III) complex with A-D-A framework in the single-emissive-layer WOLEDs
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To explore the influence of push-pull chromophores on properties of emitter in organic light-emitting devices (OLEDs), an acceptor-donor-acceptor (A-D-A)-based dinuclear iridium (III) complex of (dfppy)4Ir2(dipic-FL) was synthesized via Suzuki coupling reaction, in which dfppy is 2-(2,4-difluorophenyl)pyridine and dipic-FL is 2,7-di(5-pyridyl-2-carboxyl)-9,9-dioctyl-9H-fluorene. An intense emission peak at about 480 nm resulting from the (dfppy)2Ir(pic) chromophore and a weak long-wavelength emission band at 580-660 nm attributed to intramolecular charge transfer transition were exhibited for (dfppy)4Ir2(dipic-FL) in dichloromethane solution. But a remarkably hypsochromic photoluminescence profile with an intense characteristical emission peak at 422 nm was observed, which is attributed to the intraligand (IL)
- He, Keqi,Wang, Xiangdong,Yu, Junting,Jiang, Haigang,Xie, Guangshan,Tan, Hua,Liu, Yu,Ma, Dongge,Wang, Yafei,Zhu, Weiguo
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p. 2942 - 2949
(2015/02/02)
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- ORGANIC SEMICONDUCTOR MATERIAL, PREPARATION METHODS AND USES THEREOF
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Disclosed are organic semiconductor material, preparation methods and uses thereof. The organic semiconductor material is shown as the following formula (P), in which R1, R2, R3, m, n, x and y are defined as the description. The said organic semiconductor material can be used in organic solar cell, organic field effect transistor, organic electroluminescence element, organic optical storage, organic non-linear material or organic laser element.
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Paragraph 0047; 0048; 0049; 0050; 0051
(2013/11/19)
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- ORGANIC SEMICONDUCTOR MATERIAL, PREPARATION METHODS AND USES THEREOF
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Disclosed are organic semiconductor material, preparation methods and uses thereof. The organic semiconductor material is shown as the following formula (P), in which R1, R2, R3, m, n, x and y are defined as the description. The said organic semiconductor material can be used in organic solar cell, organic field effect transistor, organic electroluminescence element, organic optical storage, organic non-linear material or organic laser element.
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Paragraph 0049; 0050
(2013/11/19)
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- Electron-transporting naphthalimide-substituted derivatives of fluorene
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Naphthalimide-substituted derivatives of fluorene were synthesized by Suzuki-Miyaura coupling reactions. Most of the synthesized materials were found to constitute glasses with glass transition temperatures ranging from 30 to 76 C as characterized by differential scanning calorimetry. Their initial weight loss temperatures range from 315 to 466 C. Dilute solutions of the naphthalimide-substituted derivatives of fluorene in nonpolar solvents were found to emit in the blue region with high quantum yield ranging from 0.47 to 0.69, while in the solid state fluorescence quantum yields were found to be in the range of 0.06-0.25. Fluorenes possessing two naphthalimide moieties exhibited higher values of the fluorescence quantum yield due to enhanced oscillator strength of the transition. The derivatives of fluorene containing naphthalimide moieties exhibited pronounced positive solvatochromic behaviour in polar solvents indicating on charge-transfer character of the lowest excited states. Fluorescence red shift in dimethylsulfoxide is found of 94 nm, while the fluorescence quantum yield is increasing with polarity from 0.47 in cyclohexane to 0.84 in dimethylsulfoxide. Such untypical enhancement of fluorescence quantum yield is accounted to reduced intersystem crossing in polar solvents, which is proved by almost 10 fold increase in the values of nonradiative decay rate for compounds dissolved in polar solvents. Time-of-flight electron drift mobilities of the layer of 2,7-di((N-octyl-1,8-naphthalimide)-4-yl)-9,9-dioctyl- 9H-fluorene in air at 25 C appproach 1.2 × 10-3 cm2 V-1 s-1 at an eletric field of 6.4 × 105 Vcm-1.
- Gudeika,Reghu,Grazulevicius,Buika,Simokaitiene,Miasojedovas,Jursenas,Jankauskas
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p. 895 - 902
(2013/09/12)
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- Fluorescence quenching and enhancement of vitrifiable oligofluorenes end-capped with tetraphenylethene
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We report the synthesis of novel amorphous fluorene-based fluorophores that have been end-capped with tetraphenylethene (TPE). Although in the solid state the fluorophores show bright cyan fluorescence with high (68%) photoluminescence quantum efficiency (PLQE), strong fluorescence quenching is observed in solution with low PLQE values ranging from 0.3% to 2.1%. When the fluorophores were added to a 90% water-THF solvent mixture nanoparticles were formed, which was confirmed by Dynamic Light Scattering (DLS) and Atomic Force Microscopy (AFM). Subsequent fluorescence measurements reveal that all the fluorophores exhibit aggregation induced emission (AIE) with high PLQE (41%). We have carried out a comparative study of 5 fluorene-based TPE materials (F(1-5)TPE), in which the fluorene core is extended, and investigated their thermal, optical, electrochemical and electroluminescence properties. From fluorescence quantum yield data we have discovered that the AIE effect decreases as the fluorene core increases both in the nanoparticle and in the solid state. Thermal analysis reveals that all fluorophores are amorphous with high thermal stabilities. Potential application in solid state vapour sensing has been demonstrated using dichloromethane that shows "on" and "off" fluorescence behaviour. Finally, Organic Light Emitting Diodes (OLEDs) have been fabricated with device configuration ITO/PEDOT/F(1-5)TPE/TPBi/LiF/Al. The best OLED device that incorporates F1-TPE as the emitter exhibits a turn-on voltage of 5.8 V, Lmax = 1300 cd m-2, ηP,max = 1 lm W -1 and ηC,max = 2.6 cd A-1.
- Aldred, Matthew P.,Li, Chong,Zhang, Guo-Feng,Gong, Wen-Liang,Li, Alexander D. Q.,Dai, Yanfeng,Ma, Dongge,Zhu, Ming-Qiang
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supporting information; experimental part
p. 7515 - 7528
(2012/06/01)
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- COMPOUND AND ORGANIC ELECTROLUMINESCENT ELEMENT USING SAID COMPOUND
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The present invention provides a novel compound having an excellent property to inject a hole into a device such as an organic EL device. More specifically, the present invention provides a compound comprising a residue obtained by removing at least one hydrogen atom from a structure represented by the following formula (1): wherein each R1 represents a hydrogen atom, an alkyl group, or the like, each of such groups optionally having a substituent; the R1s may be the same or different; each R2 represents a hydrogen atom, an alkyl group, or the like, each of such groups optionally having a substituent; the R2s may be the same or different; each R4 represents a hydrogen atom, an alkyl group, or the like, each of such groups optionally having a substituent; the R4s may be the same or different; each R15 represents an alkyl group or the like, each of such groups optionally having a substituent; where there are a plurality of R15, they may be the same or different; each e represents an integer of from 0 to 6; and the e's may be the same or different.
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Page/Page column 77-78
(2012/12/13)
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