- Single chain white-light-emitting polyfluorene copolymers containing iridium complex coordinated on the main chain
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We report the synthesis of single chain white-light-emitting polyfluorene copolymers containing a novel iridium complex with β-diketonate unit, bis(2-benzothiazol-2-yl-N-ethylcarbazole)iridium-l,3bis(p-bromophenyl)l, 3-propanedione ((bec)2IrdbmBr), as the red emission unit. The synthesized polyfluorene copolymers containing the carbazole and iridium complex, poly{9,9-bis(4-octyloxyphenyl)fluorene-2,7-diyl-co(N-hexylcarbazole-3, 6-diyl)-co-[bis(2-benzothiazol-2-yl-N-ethylcarbazole)iridium-l, 3-bis(p-bromophenyl)propanedione-l,3-diyl]} (PFCzIrbecs), were synthesized via palladium-catalyzed Suzuki coupling reactions. These polymers were found to be thermally stable and readily soluble in common organic solvents. Interestingly, the synthesized polymers, PFCzIrbec 05 and PFCzIrbec 2, exhibited two strong emission bands in both the blue and red spectral regions. Light-emitting devices based on these polymers were fabricated in an ITO/PEDOT:PSS/poly(TPD)/polymers/ TPBi/LiF/Al configuration. We obtained white light emission from a single polymer chain by incorporating (bec)2IrdbmBr as the red emission unit into a BOPF and carbazole main chain as the host and blue emission. This device exhibited good performance. In particular, EL device fabricated with PFCzIrbec 2 was found to emit white light consisting of simultaneous blue and red emission with CIE coordinates of (0.31, 0.32), which are close to the standard for white light emission. Moreover, the EL spectrum of PFCzIrbec 2 was stable with respect applied voltage, and CIE coordinates were almost not changed at various driving voltages.
- Park, Moo-Jin,Kwak, Jeonghun,Lee, Jonghee,Jung, In Hwan,Kong, Hoyoul,Lee, Changhee,Hwang, Do-Hoon,Shim, Hong-Ku
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- Copper catalysed Gomberg-Bachmann-Hey reactions of arenediazonium tetrafluoroborates and heteroarenediazonium o-benzenedisulfonimides. Synthetic and mechanistic aspects
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Gomberg-Bachmann-Hey reactions were carried out in the presence of copper as a catalyst and gave rise to biaryls or heterobiaryls in good yields and in mild reaction conditions. A computational study of some key points of the reaction was performed. The results are coherent with the experimental data and confirm some aspects of the mechanism. The reaction free energies for the reduction in benzene by CuI of a set of 40 (hetero)arenediazonium tetrafluoroborates were calculated. Both the experiments and the calculations showed that in the coupling with substituted solvents (toluene, bromobenzene, nitrobenzene and anisole) the binding to the ortho position was always favoured.
- Antenucci, Achille,Barbero, Margherita,Dughera, Stefano,Ghigo, Giovanni
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- Design, Synthesis, and Pharmacological Characterization of Carbazole Based Dopamine Agonists as Potential Symptomatic and Neuroprotective Therapeutic Agents for Parkinson's Disease
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We have developed a series of carbazole-derived compounds based on our hybrid D2/D3 agonist template to design multifunctional compounds for the symptomatic and disease-modifying treatment of Parkinson's disease (PD). The lead molecules (-)-11b (D-636), (-)-15a (D-653), and (-)-15c (D-656) exhibited high affinity for both D2 and D3 receptors and in GTPγS functional assay, the compounds showed potent agonist activity at both D2 and D3 receptors (EC50 (GTPγS); D2 = 48.7 nM, D3 = 0.96 nM for 11b, D2 = 0.87 nM, D3 = 0.23 nM for 15a and D2 = 2.29 nM, D3 = 0.22 nM for 15c). In an animal model of PD, the test compounds exhibited potent in vivo activity in reversing hypolocomotion in reserpinized rats with a long duration of action compared to the reference drug ropinirole. In a cellular antioxidant assay, compounds (-)-11b, (-)-15a, and (-)-15c exhibited potent activity in reducing oxidative stress induced by neurotoxin 6-hydroxydopamine (6-OHDA). Also, in a cell-based PD neuroprotection model, these lead compounds significantly increased cell survival from toxicity of 6-OHDA, thereby producing a neuroprotective effect. Additionally, compounds (-)-11b and (-)-15a inhibited aggregation and reduced toxicity of recombinant alpha synuclein protein in a cell based in vitro assay. These observations suggest that the lead carbazole-based dopamine agonists may be promising multifunctional molecules for a viable symptomatic and disease-modifying therapy of PD and should be further investigated.
- Elmabruk, Asma,Das, Banibrata,Yedlapudi, Deepthi,Xu, Liping,Antonio, Tamara,Reith, Maarten E. A.,Dutta, Aloke K.
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p. 396 - 411
(2019/01/24)
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- Blue light emission of new anthracene derivatives produced using optimized side group link positions
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Using an anthracene chromophore as a core group and a phenyl carbazole chromophore as a side group, three new emitters of blue light, 2-DCPA, 3-DCPA and 4-DCPA, were synthesized. The three compounds differed with regard to the position of the carbazole linked to the core, with 2-DCPA and 4-DCPA using carbazole nodes and 3-DCPA using the lobe position. Density functional theory calculations were performed to determine which positions of the carbazole moiety had node characteristics and which had lobe characteristics. The PLmax values of 2-DCPA, 3-DCPA and 4-DCPA in the film state were in the blue region, at 453, 457, and 452 nm, respectively. Of these materials, 3-DCPA, i.e., that with the linkage to the lobe position, showed the highest efficiency, with a value of 2.91 cd/A, and EQE, with a value of 2.65%. In a doped device using CBP as a host material and 3-DCPA as a dopant, the ELmax emission was observed to be in the deep blue region, at 433 nm, and with a CIE value of (0.150, 0.068).
- Kang, Seokwoo,Jung, Hyocheol,Lee, Hayoon,Lee, Suji,Jung, Mina,Lee, Jaehyun,Chul Kim, Young,Park, Jongwook
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p. 369 - 378
(2018/05/09)
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- COMPOUND, MATERIAL FOR ORGANIC ELECTROLUMINESCENCE DEVICE, ORGANIC ELECTROLUMINESCENCE DEVICE AND ELECTRONIC APPARATUS
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A compound represented by the following formula (1):
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Paragraph 0290; 0291; 0292; 0306; 0310
(2018/12/11)
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- COMPOUND FOR ORGANIC ELECTROLUMINESCENT DEVICE AND ORGANIC ELECTROLUMINESCENT DEVICE COMPRISING THE SAME
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This invention provides a compound for an organic electroluminescent device and an organic electroluminescent device including the same. This invention provides a compound for an organic EL device, which may have high thermal stability, improved light emission efficiency and lifetime and hole transport capability. Further, when this compound is used as a hole transport layer material in contact with a light emitting layer, thereby increasing a triplet energy, ultimately improving efficiency of the organic EL device and lifetime.
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Paragraph 261; 262; 263; 264
(2017/12/01)
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- Iridium complexes demonstrating broadband emission through controlled geometric distortion and applications thereof
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Iridium compounds and their uses are disclosed herein. For example, carbazole containing iridium compounds are disclosed. The compounds are useful in many devices, including, but not limited to, electroluminescent devices.
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Page/Page column 27; 28
(2016/05/09)
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- Synthetic method of 2-bromocarbazole and intermediate thereof
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The invention discloses a synthetic method of 2-bromocarbazole and an intermediate thereof. The synthetic method includes the steps of 1) with dichloromethane as a solvent and tert-butyl nitrite as a diazotization reagent, diazotizating o-nitroaniline and performing a coupling reaction to the diazotizated o-nitroaniline and bromobenzene to prepare an intermediate 4-bromo-2'-nitrobiphenyl; 2) adding enough triethyl phosphite to the 4-bromo-2'-nitrobiphenyl to perform a ring closing reaction to the 4-bromo-2'-nitrobiphenyl and the triethyl phosphite; 3) when the ring closing reaction is finished, adding enough hydrochloric acid to damage the triethyl phosphite which is not reacted; and 4) filtering and drying a reaction product to prepare the 2-bromocarbazole.
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Paragraph 0023; 0026
(2016/10/17)
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- Organic electroluminescent materials and devices
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Novel phosphorescent platinum complexes containing tetradentate ligands are provided. The disclosed compounds have three 6-membered metallocycle units in each tertadentate ligand. The disclosed compounds have desirable electronic properties that make them useful when incorporated into a variety of OLED devices.
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Page/Page column 185
(2016/10/27)
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- Organic electroluminescent materials and devices
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Phosphorescent metal complexes comprising a pendant redox-active metallocene are disclosed. These complexes are useful as emitters for phosphorescent OLEDs.
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Page/Page column 140; 141
(2016/10/17)
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- ORGANIC ELECTROLUMINESCENT MATERIALS AND DEVICES
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Imidazophenanthridine ligands and metal complexes are provided. The compounds exhibit improved stability through a linking substitution that links a nitrogen bonded carbon of an imidizole ring to a carbon on the adjacent fused aryl ring. The compounds may be used in organic light emitting devices, particularly as emissive dopants, providing devices with improved efficiency, stability, and manufacturing. In particular, the compounds provided herein may be used in blue devices having high efficiency.
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- METAL COMPLEXES, METHODS, AND USES THEREOF
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Metal complexes that exhibit multiple radiative decay mechanisms, together with methods for the preparation and use thereof.
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Paragraph 0156; 0157
(2015/12/23)
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- Ni(II) catalyzed bromination of aryl C-H bonds
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Bromination of unactivated aromatic C-H bonds without directing and/or chelating groups was achieved by employing an air stable N-heterocyclic Ni(II) complex. PhI(OAC)2 and N-bromosuccinimide have been used as the oxidizing agent and the bromin
- Bhattacharya, Moumita,Cluff, David B.,Das, Siddhartha
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p. 238 - 241
(2014/12/11)
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- Ni(II) catalyzed bromination of aryl C-H bonds
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Bromination of unactivated aromatic C-H bonds without directing and/or chelating groups was achieved by employing an air stable N-heterocyclic Ni(II) complex. PhI(OAC)2and N-bromosuccinimide have been used as the oxidizing agent and the bromine source, respectively. Yields for bromination are as high as >99%, especially in presence of electron-withdrawing groups like -NO2and -CF3. This is a rare report on C-H bond activation with Ni(II) where, instead of homo C-C coupling, reductive elimination to form C-halogen could be achieved.
- Bhattacharya, Moumita,Cluff, David B.,Das, Siddhartha
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p. 238 - 241
(2015/02/20)
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- NOVEL ORGANIC ELECTROLUMINESCENT COMPOUNDS AND ORGANIC ELECTROLUMINESCENT DEVICE COMPRISING THE SAME
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The present invention relates to a novel organic electroluminescent compound and an organic electroluminescent device comprising the same. The organic electroluminescent compound according to the present invention has high green luminous efficiency and superior material lifespan characteristics, compared with conventional phosphorescent host materials, and thus can provide an organic electroluminescent device which is excellent in operational lifespan, and induces increased power efficiency and improves power consumption.
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Paragraph 160; 161
(2013/11/18)
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- Iridium complexes containing 2-aryl-benzothiazole ligands: Color tuning and application in high-performance organic light-emitting diodes
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Three 2-aryl-benzothiazole chromophores were designed and synthesized for use as major cyclometalating ligands of iridium complexes, in which the aryl groups were N-phenyl-3-carbazolyl, 2-(9,9-dioctyl)fluorenyl and N-phenyl-2-carbazolyl. The homoleptic tris-cyclometalated and heteroleptic bis-cyclometalated iridium complexes, 1-5, were synthesized using these ligands. By adjusting the chemical structures and then the electronic state of these complexes, we were able to continuously tune the phosphorescence from yellow to saturated red with peak wavelengths in the order of 1 -1, 48.2 lm W-1, and 23.0% with CIE (0.46, 0.53), which represent the highest efficiencies for yellow OLEDs up to now. Furthermore, 1 was used to fabricate two-element white OLEDs in combination with a blue phosphor and high efficiencies of 57.9 cd A-1 and 21.9% were achieved, which are among the best efficiencies for two-emitting-component white OLEDs reported so far. The Royal Society of Chemistry 2013.
- Li, Jiuyan,Wang, Renjie,Yang, Ruixia,Zhou, Wei,Wang, Xin
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p. 4171 - 4179
(2013/08/15)
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- SYNTHESIS OF PLATINUM AND PALLADIUM COMPLEXES AS NARROW-BAND PHOSPHORESCENT EMITTERS FOR FULL COLOR DISPLAYS
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Platinum and palladium complexes are disclosed that can be useful as narrow band phosphorescent emitters. Also disclosed are methods for preparing and using the platinum and palladium complexes
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Page/Page column 28
(2012/12/13)
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- NOVEL ORGANIC ELECTROLUMINESCENT COMPOUNDS AND ORGANIC ELECTROLUMINESCENT DEVICE USING THE SAME
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Organic electroluminescent compounds comprising a triphenylene conjugated to a five-ring fused heterocyclic system, as depicted in formula 1 are provided. Also provided is an organic electroluminescent device comprising these compounds. The organic electroluminescent compounds disclosed herein exhibit good luminous efficiency and excellent material life. They can be used to manufacture OLED devices very superior in terms of operating life and which consume less power due to improved power efficiency.
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Page/Page column 20
(2012/04/10)
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- NOVEL COMPOUNDS FOR ORGANIC ELECTRONIC MATERIAL AND ORGANIC ELECTROLUMINESCENT DEVICE USING THE SAME
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The present invention relates to a novel compound and an organic electroluminescent device containing the same. Since the compounds according to the present invention have high efficiency in transporting electrons, crystallization could be prevented when manufacturing a device. Further, the compounds have good layer formability and improve the current characteristic of the device. Therefore, they can produce an organic electroluminescent device having lowered driving voltages and enhanced power efficiency.
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Page/Page column 16
(2013/02/27)
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- PROCESS FOR THE PRODUCTION OF BIPHENYLS
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The present invention relates to a novel process for the preparation of a compound of formula (I): which comprises reacting a compound of formula (II): with a compound of general formula (III): wherein R1 and R2 are H or C1-4 alkyl or R1 and R2 join together to form a C2-3 alkylene group, which is optionally substituted by from 1 to 4 methyl or ethyl groups, or an anhydride of the compound (III), in the presence of a base and of a palladium catalyst which is (a) a palladium (0)- or palladium (IΙ)-triarylphosphine complex optionally in the presence of additional amounts of a triarylphoshine ligand, or (b) a palladium (II) salt in the presence of a triarylphosphine ligand, or (c) metallic palladium, optionally deposited on a support, in the presence of triarylphosphine; there being used from 0.9 to 2 moles of compound (III) for each mole of compound (II).
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Page/Page column 10-11
(2008/06/13)
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- Syntheses and photophysical properties of some 4-arylpyridinium salts
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A number of 4-arylpyridines, many methoxy substituted, were prepared by an efficient two-step method involving aryl Grignard addition to 1-methyl-4-piperidone and direct aromatization of the resulting 4-aryl-4-piperidinols. The pyridines were N-alkylated to give sulfonate salts desired for their fluorescent properties. Study of selected compounds as laser dyes revealed several structures to be efficient dyes lasing in the 530-550 nm range. Two new diazaquaterphenyls were prepared and were quaternized. These salts exhibited intense fluorescence in the 420-450 nm range, but would not lase. A phenolic azaterphenyl suitably substituted for excited state intramolecular proton transfer (ESIPT) did not fluoresce at all.
- Kelley,Ansu,Budisusetyo,Ghiorghis,Qin,Kauffman
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- Process for preparing nitrobiphenylene
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The invention concerns a process for preparing nitrobiphenylene of formula (I) wherein m stands for 1 or 2, R means halogen, R' or OR', R' being a C-organic group which can carry groups which are inert in the reaction conditions, n stands for 0, 1, 2 or 3 and, if n is 2 or 3, the R groups can also be different. According to the invention, a chloronitrobenzene of formula (II) is reacted in the presence of a palladium catalyst and a base in a solvent with a phenyl boric acid (IIIa), one of its alkyl esters of formula (IIIb), R meaning C1-C6 alkyl, or one of its anhydrides. The compounds (I) are suitable as initial products for biphenylamines which are in turn intermediate products for fungicidal plant-growth substances.
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