- Novel thiophene-containing push-pull chromophores that include carbazole and triphenylamine moieties: study of optical and electrochemical properties
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[Figure not available: see fulltext.] Novel carbazole- and triphenylamine-containing alkylidene malononitriles that include thiophene and bithienyl fragments as π-spacers were synthesized. Quantum-chemical calculations of the frontier molecular orbital energies were performed using the B3LYP/6-31G(d) method with regard to solvent. Electronic absorption spectra and fluorescence spectra were recorded for all the obtained compounds; their electrochemical properties were also studied. The experimental energy values of HOMO and LUMO levels were derived from resulting data. Thin films were obtained by the spin coating technique, and their surface morphology was studied using a NTEGRA Prima scanning tunneling microscope.
- Bakiev, Artur N.,Selivanova, Darya G.,Lunegov, Igor V.,Vasyanin, Aleksandr N.,Maiorova, Olga A.,Gorbunov, Aleksei A.,Shklyaeva, Elena V.,Abashev, Georgii G.
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Read Online
- Controlled synthesis of conjugated microporous polymer films: Versatile platforms for highly sensitive and label-free chemo- and biosensing
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Conjugated microporous polymers (CMPs), in which rigid building blocks form robust networks, are usually synthesized as insoluble and unprocessable powders. We developed a methodology using electropolymerization for the synthesis of thin CMP films. The thickness of these films is synthetically controllable, ranging from nanometers to micrometers, and they are obtained on substrates or as freestanding films. The CMP films combine a number of striking physical properties, including high porosity, extended π conjugation, facilitated exciton delocalization, and high-rate electron transfer. We explored the CMP films as versatile platforms for highly sensitive and label-free chemo- and biosensing of electron-rich and electron-poor arenes, metal ions, dopamine, and hypochloroic acid, featuring rapid response, excellent selectivity, and robust reusability.
- Gu, Cheng,Huang, Ning,Gao, Jia,Xu, Fei,Xu, Yanhong,Jiang, Donglin
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Read Online
- A bipolar emitting material for high efficient non-doped fluorescent organic light-emitting diode approaching standard deep blue
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A deep blue emitting compound 9-(4′-(1,4,5-triphenyl-1H-imidazol-2-yl)-[1,1′-biphenyl] -4-yl)-9H-carbazole was designed and synthesized. The emitting compound characters as donor-π-acceptor structure with carbazole as the electron-donor and imidazole as the electron-acceptor. The emitting compound shows high quantum yield (0.87) in solution and good thermal stability. The emitting compound exhibits bipolar transporting characteristics identified by single-carrier devices. The non-doped fluorescent organic light-emitting diode with the emitting compound as emitting layer exhibits emission peak at 420 nm and full width at half maximum of 54 nm, maximum current efficiency of 2.30 cd/A, and maximum power efficiency of 1.52 lm/W, which are higher than most reported deep blue emitters with a y coordinate ≤0.064. The chromaticity coordinate is stable at (0.166, 0.064) with increasing operation voltage.
- Fan, Shigen,You, Jing,Miao, Yanqin,Wang, Hua,Bai, Qingyun,Liu, Xicheng,Li, Xianggao,Wang, Shirong
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Read Online
- Carbazole-diphenylimidazole based bipolar material and its application in blue, green and red single layer OLEDs by solution processing
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Single layer structure is an ideal way to realize the low cost solution processed organic light-emitting diodes (OLEDs). Efficient electroluminescent material with hole and electron transport characters as well as suitable triplet energy levels is highly desired to realize single layer OLEDs with good performance. In this work, a bipolar compound with carbazole as electron donor and 4,5-diphenylimidazoleas as electron acceptor has been successfully synthesized and applied as emitting layer for both non-doped and doped single layer OLEDs fabricated by solution processing. A pure blue emission achieved in the non-doped single layer OLED with a current efficiency of 0.38 cd A?1, luminance up to 672 cd m?2. The single layer doped OLEDs with the bipolar compound as host achieved blue, green and red phosphorescence OLEDs with current efficiency of 0.083, 13.42, 2.58 cd A?1 and luminance up to 108, 17103, 1347 cd m?2, respectively. The performance of single layer OLEDs has been greatly improved by bipolar emitting materials which show a great potential to simplify the configuration of OLEDs.
- Wang, Panpan,Fan, Shigen,Liang, Junfei,Ying, Lei,You, Jing,Wang, Shirong,Li, Xianggao
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Read Online
- Red emissive organic light-emitting diodes based on codeposited inexpensive CuI complexes
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Inexpensive materials made of abundant natural resources such as CuI complexes are essential to sustain the development of organic light emitting diode (OLED) technology for mass market applications such as solid-state illumination. CuI complexes, however, mostly are neither soluble nor stable toward sublimation, which is a road block for the development of efficient CuI complex based OLEDs using traditional methods of synthesis, sublimation and vacuum evaporation. In this work, two isoquinolyl carbazole (CIQ) compounds 9-(8-(carbazol-9-yl)isoquinolin-5-yl)-carbazole (DCIQ) and 9-(4-(5-(4-(carbazol-9-yl)phenyl)isoquinolin-8-yl)phenyl)-carbazole (DCDPIQ) were synthesized to codeposition with copper iodide (CuI) to form red emissive dimeric CuI complex doped film in situ, which could be utilized directly as the emissive layer (EML) in OLEDs. After a systematic study of the two compounds and their codeposited CuI:CIQ films, as well as optimizing the CuI doping concentration, it is found that red OLEDs can be achieved, showing a maximum emission band, an external quantum efficiency (EQE), a luminance of 643 nm, 3.5%, 3290 cd m-2 for DCIQ, and 635 nm, 3.6%, 853 cd m-2 for DCDPIQ, respectively.
- Ni, Tianchi,Liu, Xiaochen,Zhang, Tao,Bao, Hongliang,Zhan, Ge,Jiang, Nan,Wang, Jianqiang,Liu, Zhiwei,Bian, Zuqiang,Lu, Zhenghong,Huang, Chunhui
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Read Online
- Preparation method of 4-(9H-carbazol-9-yl)phenylboronic acid
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The invention relates to a preparation method of 4-(9H-carbazol-9-yl)phenylboronic acid, belonging to the technical field of organic synthesis. The preparation method comprises the following steps: with carbazole as an initial raw material, subjecting carbazole to reacting with 4-chlorobromobenzene to generate 9-(4-chlorphenyl)-9H-carbazole; and then condensing 9-(4-chlorphenyl)-9H-carbazole with triethyl borate, and carrying out hydrolyzing to generate the 4-(9H-carbazol-9-yl)phenylboronic acid. According to the method, n-butyllithium is not used in the process of preparing the 4-(9H-carbazol-9-yl)phenylboronic acid, so an ultralow-temperature reaction is avoided, and all the reactions are carried out under mild conditions; and compared with an existing synthesis process, the method is more suitable for industrial production.
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Paragraph 0005; 0021; 0024-0025; 0029; 0032-0033
(2021/11/06)
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- COMPOUND AND ORGANIC LIGHT EMITTING DEVICE COMPRISING THE SAME
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The present invention provides a compound of chemical formula 1 and an organic light emitting device comprising the same. The compound according to an embodiment of the present invention has excellent lifespan characteristics and can have high luminous efficiency even at a low driving voltage.COPYRIGHT KIPO 2020
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Paragraph 0143; 0146-0148
(2020/07/29)
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- ORGANIC COMPOUNDS, ORGANIC LIGHT EMITTING DIODE AND ORGANIC LIGHT EMITTID DEVICE HAVING THE COMPOUNDS
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The present invention relates to an organic compound in which a bipyrimidine moiety serving as an electron acceptor is connected via an aromatic linker to a hetero-aromatic moiety serving as an electron donor and containing one to two nitrogen atoms. The organic compound, since it contains both electron donor and electron acceptor moieties in a single molecule, allows electric charges to move easily, thereby increasing luminance efficiency. Also, since the electron donor is made of solid condensed aromatic rings, such as carbazole, acridine, or indole rings, the 3D structure of the molecule is hindered. Thus, the organic compound of the present invention may be used as a delayed fluorescence dopant emitting a blue light of high chromatic purity. The organic compound of the present invention may be applied to organic light-emitting devices, such as an organic light-emitting diode, a display device, and a lighting device, to lower the driving voltage thereof while increasing luminance efficiency and chromatic purity thereof.COPYRIGHT KIPO 2019
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- Aromatic compound and organoelectroluminescent device comprising the compound
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The present invention relates to a novel aromatic compound and an organic electroluminescent device comprising the same. The present invention relates to an organic electroluminescent device including an aromatic compound. (by machine translation)
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Paragraph 0198; 0205-0210
(2019/12/10)
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- Achieving non-doped deep-blue OLEDs by applying bipolar imidazole derivatives
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In this work, we designed and synthesized two novel bipolar deep-blue emitting materials, 2-(4'-(9H-carbazol-9-yl)-[1,1′-biphenyl]-4-yl)-1 (4(tri-fluoromethyl) phenyl)-1H-phenanthro[9,10-d] imidazole (CzB-FMPPI) and 9-(4'-(4,5-diphenyl-1 (4-(trifluoromethyl) phenyl)-1H-imidazole-2-yl)-[1,1′-biphenyl]-4-yl)-9H-carbazole (CzB-FMPIM). Among them, carbazole and phenanthroimidazole are bridged linkage by the biphenyl ring and act as electron-donating part. The CF3-substituted phenyl ring applies as strong electron-withdrawing moiety. The exhibit highly twisted molecular configuration of two compounds efficiently shorten π-conjugation and inhibit intermolecular interaction, resulting in superior thermal stability and deep blue emission. High decomposition temperature of 431 °C and 414 °C, glass transition temperature of 150 °C and 135 °C for CzB-FMPPI and CzB-FMPIM, respectively, had been achieved. As a consequence of breaking the conjugation of phenanthroimidazole chromophore, CzB-FMPIM achieves an 8 nm blue-shifted emission compared with CzB-FMPPI. CzB-FMPPI exhibits a higher relative fluorescence quantum yield of 92.5% than 83.3% of CzB-FMPIM. Moreover, bipolar property was observed in both compound and homogeneous amorphous films were deposited and applied in the non-doped deep-blue OLEDs. The devices based on two emitters showed maximum luminance of 6667 cd/m2 and 3084 cd/m2, maximum EQE of 4.10% and 3.17%, respectively. Commission International de l'éclairage (CIE) coordinates of CzB-FMPIM based device achieved (0.15, 0.07) which is extremely close to the NTSC standard blue CIE (0.14, 0.08).
- Jia, Yi,Wu, Sen,Zhang, Yuteng,Fan, Shigen,Zhao, Xiaoming,Liu, Hongli,Dong, Xiaofei,Wang, Shirong,Li, Xianggao
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p. 289 - 296
(2019/04/13)
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- Heterocyclic com pounds and organic light-emitting diode including the same
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The present invention relates to novel heterocyclic compounds of chemical formula 1 and an organic electroluminescent device containing the same as a light emitting material and, more specifically, to stable heterocyclic compounds with superior light emitting properties such as driving voltage and light emitting efficiency; and an organic electroluminescent device containing the same. Also, the present invention provides an organic electroluminescent device comprising an anode, a cathode, and layers which are inserted between the anode and the cathode and contain the heterocyclic compounds of chemical formula 1.
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Paragraph 0252; 0259-0264
(2019/11/29)
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- New compounds and organic light-emitting diode including the same
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PURPOSE: A compound is provided to improve luminous efficiency and to make low voltage operation possible when applied to an organic electroluminescence device by having low driving voltage and excellent luminous efficiency. CONSTITUTION: A compound is represented by chemical formula 1. In chemical formula 1, each R is selected from hydrogen, deuterium, substituted or unsubstituted C1-6 alkyl, substituted or unsubstituted C7-30 alkyl, substituted or unsubstituted C3-30 cycloalkyl, substituted or unsubstituted C5-30 cycloalkenyl, substituted or unsubstituted C1-30 alkoxy, substituted or unsubstituted C6-30 aryloxy, substituted or unsubstituted C1-30 alkylthioxy, substituted or unsubstituted C5-30 arylthioxy, substituted or unsubstituted C1-30 alkylamine, substituted or unsubstituted C5-30 arylamine, substituted or unsubstituted C5-50 aryl, substituted or unsubstituted C3-50 heteroaryl, substituted or unsubstituted silicon, substituted or unsubstituted boron, substituted or unsubstituted silane, carbonyl, phosphoryl, amino, nitrile, hydroxy, nitro, halogen, amide, and ester.
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Paragraph 0200-0206; 0334; 0341-0346
(2019/08/30)
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- Phenanthroline- tBuOK Promoted Intramolecular C-H Arylation of Indoles with ArI under Transition-Metal-Free Conditions
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The first example of phenanthroline-tBuOK promoted intramolecular radical C-H arylation of N-(2-iodobenzyl)indoles without involvement of transition metals has been developed. A variety of substituted 6H-isoindolo [2, 1-a] indoles were prepared by a simple and efficient intramolecular cyclization using 1,10-phenanthroline in the presence of potassium tert-butoxide and chlorobenzene. This strategy provides a fast and versatile access to isoindolo[2,1-a]indole derivatives for the synthesis of pharmaceuticals and organic electroluminescent (EL) materials.
- Shan, Xiang-Huan,Yang, Bo,Zheng, Hong-Xing,Qu, Jian-Ping,Kang, Yan-Biao
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p. 7898 - 7901
(2019/01/04)
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- Novel thiophene-containing push-pull chromophores that include carbazole and triphenylamine moieties: study of optical and electrochemical properties
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[Figure not available: see fulltext.] Novel carbazole- and triphenylamine-containing alkylidene malononitriles that include thiophene and bithienyl fragments as π-spacers were synthesized. Quantum-chemical calculations of the frontier molecular orbital energies were performed using the B3LYP/6-31G(d) method with regard to solvent. Electronic absorption spectra and fluorescence spectra were recorded for all the obtained compounds; their electrochemical properties were also studied. The experimental energy values of HOMO and LUMO levels were derived from resulting data. Thin films were obtained by the spin coating technique, and their surface morphology was studied using a NTEGRA Prima scanning tunneling microscope.
- Bakiev, Artur N.,Selivanova, Darya G.,Lunegov, Igor V.,Vasyanin, Aleksandr N.,Maiorova, Olga A.,Gorbunov, Aleksei A.,Shklyaeva, Elena V.,Abashev, Georgii G.
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p. 379 - 387
(2021/04/15)
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- Preparation method and application of pyrimidine derivatives connected with four same electron donating groups
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The invention relates to a preparation method and application of pyrimidine derivatives connected with four same electron donating groups, and belongs to the technical field of application of luminescent materials in the production of organic electroluminescent devices. The pyrimidine derivatives utilize a steric hindrance effect generated by dense arrangement of small groups to carry out conjugate blocking between an electron donor and a receptor, so HOMO and LUMO energy levels realize high degree separation, and the high radiation rate constant of molecules is guaranteed. The above organic electroluminescent materials can simultaneously utilize singlet state and triplet state exciton luminescence; and additionally, the materials are organic micro-molecules, have the advantages of stable chemical properties, no precious metal coordination and low cost, and can be applied to the organic electroluminescent devices as luminescent materials.
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- A same substituent containing four of six-double-nitrogen heterocyclic derivatives of the preparation method and application thereof (by machine translation)
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A same substituent containing four of six-double-nitrogen heterocyclic derivatives of the preparation method and its application, which belongs to the light-emitting material in the preparation of the organic electroluminescent device of the application technology field. The derivative is to pyrazine, pyridazine as a light-emitting material electron acceptor, in its peripheral connecting carbazole, phenoxazine, 9, 9 - dimethyl - 9, 10 - dihydro acridine such electron donor, by adjusting with the LUMO HOMO between the degree of overlapping of the front edge of the track, and then expect to obtain a number of thermal delay fluorescent (TADF) nature of the light-emitting material. At room temperature, these derivatives in the visible ultraviolet - with strong absorption, and its dilute solution emit strong fluorescence, peak at 450 - 615 nanometers, which belongs to the range - orange blue light, can be used as a light-emitting material is applied to the organic electroluminescent device. Based on compound M2 device, starting voltage of 3.9 V, when the voltage reaches a 12V when reaching maximum brightness 3846cdm- 2 . In current density for the 0.06mAcm- 2 (4.5V) when, the device reach maximum luminous efficiency 17.4cdA- 1 And the maximum power efficiency 12.2lmW- 1 . (by machine translation)
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Paragraph 0020
(2017/04/26)
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- Delay fluorescent compound and using the same and display device having the organic light-emitting diode (by machine translation)
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The present invention provides a delay fluorescent compound and the use of the compound of the organic light-emitting diode and the display device, the delay fluorescent compound is a type 1 or type 2 delay fluorescent compound : [formula 1] ; [Formula 2] . (by machine translation)
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Paragraph 0225; 0026; 0227; 0228
(2016/10/08)
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- Porous Organic Polymer Films with Tunable Work Functions and Selective Hole and Electron Flows for Energy Conversions
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Organic optoelectronics are promising technologies for energy conversion. However, the electrode interlayer, a key material between active layers and conducting electrodes that controls the transport of charge carriers in and out of devices, is still a chemical challenge. Herein, we report a class of porous organic polymers with tunable work function as hole- and electron-selective electrode interlayers. The network with organoborane and carbazole units exhibits extremely low work-function-selective electron flow; while upon ionic ligation and electro-oxidation, the network significantly increases the work function and turns into hole conduction. We demonstrate their outstanding functions as anode and cathode interlayers in energy-converting solar cells and light-emitting diodes.
- Gu, Cheng,Huang, Ning,Chen, Youchun,Zhang, Huanhuan,Zhang, Shitong,Li, Fenghong,Ma, Yuguang,Jiang, Donglin
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supporting information
p. 3049 - 3053
(2016/03/12)
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- 1, 2, 4-thiadiazole derivatives and their use as electroluminescent materials
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The invention relates to design and synthesis of organic electroluminescence materials which take 1,2,4-thiadiazole electronics transmission groups as a central unit as well as an application of the 1,2,4-thiadiazole electronics transmission groups on an organic electroluminescent device (OLED). The electroluminescent materials take 1,2,4-thiadiazole as a core, groups with different electronic or cavity transmission groups are bonded at positions 3 and 5 sites of 1,2,4-thiadiazole, carrier balance can be effectively solved, exciton recombination with high efficiency is radically realized, thus further combination of high efficiency light-emitting and energy level adjustment of the material can be realized. In addition, the energy level of the compound can be adjusted through an unsymmetrical structure, compared with the electronics transmission groups (such as oxadiazoles, 1,3,5-triazole) in the common main materials, the OLED devices has substantial effects in brightness, efficiency, glass transition temperature and the like, so that the material provided in the invention can be widely applied in the field of organic electroluminescence.
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- Novel green-ray host compound and preparation method and application thereof
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A novel carbazole derivative is a perssad which is used for connecting Ar1 and Ar2 of ether structures in a carbazole compound and improving the three-dimensional performance of the carbazole compound. According to a novel green-ray host compound and a preparation method and application of the novel green-ray host compound, disclosed by the invention, the luminous wave length is easily adjusted while a three-dimensional effect of the carbazole compound is formed by introducing an ether compound, and a new derivative, which is used for increasing the luminous efficiency of a device and prolonging the service life of the device, of the carbazole compound is provided; the device which is made by using the new carbazole derivative has the advantages of high luminance, excellent heat resistance, long service life, high efficiency and the like.
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Paragraph 0035; 0036; 0037
(2016/10/08)
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- New carbazole compound and preparation method and application thereof
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A new carbazole derivative is an asymmetric carbazole compound; the hole mobility degree is increased through linking of Ar1 and Ar2 and introduction of an R1 group, and performance is improved through adjustment of the Ar2 molecular weight and ligand types; devices manufactured by using the new carbazole derivative has the characteristics of high brightness, excellent heat resistance, long lifetime, high efficiency and the like.
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Paragraph 0038; 0039; 0040; 0041
(2016/10/08)
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- MULTICYCLIC COMPOUND HAVING NITROGEN AND ORGANIC LIGHT EMITTING DEVICE USING THE SAME
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The present invention relates to a nitrogen-containing polycyclic compound employing a novel structure and an organic light emitting device using the same. According to the present invention, the nitrogen-containing polycyclic compound can be used to form an organic layer in the organic light emitting device.COPYRIGHT KIPO 2015
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Paragraph 0192-0193; 0202-0203
(2016/10/09)
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- Bipolar host materials for high-efficiency blue phosphorescent and delayed-fluorescence OLEDs
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A series of small molecular isomers, namely o-CzCN, m-CzCN, and p-CzCN, are developed for use as bipolar hosts in blue phosphorescent and fluorescent organic light-emitting diodes (OLEDs). Cyano (CN) substituted phenyl is selected as the n-type unit and N-phenyl-substituted carbazole as the p-type unit. By adjusting the ortho-, meta-, and para-linking styles of the functional units, the physical parameters are regularly tuned to a large extent. The study of complete spatial separation of frontier molecular orbitals and single-carrier devices confirm the bipolar feature. Blue phosphorescent and thermally activated delayed fluorescence (TADF) OLEDs were fabricated using iridium(iii)bis(4,6-(difluorophenyl)pyridinato-N,C2′)picolinate (FIrpic) and 1,2-bis(carbazol-9-yl)-4,5-dicyanobenzene (2CzPN) as doped emitters. A maximum current efficiency of 46.81 cd A-1 and an external quantum efficiency of 23.14% were achieved for the phosphorescent OLED with the m-CzCN host. Furthermore, high efficiencies of 29.23 cd A-1 and 14.98% were obtained for the 2CzPN based blue TADF device with the o-CzCN host, which are higher than the best literature value of 13.6% for 2CzPN devices. Both m-CzCN and o-CzCN always perform better than p-CzCN. The influence of the chemical structures on their properties and performance is interpreted for these CN-decorated host materials.
- Li, Wei,Li, Jiuyan,Liu, Di,Wang, Fang,Zhang, Shufen
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supporting information
p. 12529 - 12538
(2015/12/18)
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- LUMINESCENT ORGANIC COMPOUND CONTAINING FLUORENE GROUP, AND ORGANIC LIGHT EMITTING DIODE INCLUDING THE SAME
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The present invention relates to an organic light emitting compound including a fluorine group having a structure in chemical formula 1 where R^1 is carbazole or carbazole derivative, R^2 is triazole or triazole derivative and R^3 or R^4 is one selected from a group consisting of H, CN randomly substituted C1-C4 alkyl or aryl group. In the present invention, provided are an organic light emitting compound, including a fluorine group which has a high efficiency and an outstanding thermostability and emits blue or green with good quality, and an organic light emitting diode including the same.COPYRIGHT KIPO 2015
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Paragraph 0052; 0066; 0067
(2016/11/24)
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- LUMINESCENT ORGANIC COMPOUND CONTAINING SPIROFLUORENE GROUP, AND ORGANIC LIGHT EMITTING DIODE INCLUDING THE SAME
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The present invention relates to an organic light emitting compound including a spirofluorene group having a structure in chemical formula 1 where R^1 is carbazole or carbazole derivative, and R^2 is triazole or triazole derivative. In the present invention, provided are an organic light emitting compound, including a spirofluorene group which has a high efficiency and an outstanding thermostability and emits blue or green with good quality, and an organic light emitting diode including the same.COPYRIGHT KIPO 2015
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Paragraph 0055; 0066; 0067
(2016/11/28)
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- Tetraphenylsilane group containing carbazoles as high triplet energy host materials for solution-processable PhOLEDs
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A series of solution processable, wide band-gap host materials composed of carbazole and tetraphenylsilane groups were designed and synthesized. Their thermal, electrochemical, and photophysical properties were fully investi- gated. The introduction of bulky tetraphenylsilane and tert-butyl groups around the carbazole led to high glass transition temperatures (Tg) between 120 and 204 ° C. The triplet energies (ET ) of the synthesized materials were examined by low temperature (77 K) photoluminescence studies and determined as ET > 2.6 for all compounds. Phosphorescent organic light-emitting devices with the ITO/PEDOT:PSS/EML/TPBi/Cs2CO3 /Al device structure were fabricated by using synthesized materials as the host and two kinds of phosphorescent emitters, FIrpic and Ir(ppy)3 , as the guests. The highest luminous and power efficiency values obtained by using FIrpic were 3.6 cd A -1 and 1.48 lm W -1 , respectively, with commission International de I'Eclairage (CIE) coordinates of (0.17, 0.36), whereas these values were 7.8 cd A -1 and 2.9 lm W -1 for the device structure when Ir(ppy)3 was used as the guest [CIE (0.28, 0.62)].
- ?ner, Saliha,?ner, Ilker,Akdag, Haydar,Varlikli, Canan
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p. 917 - 929
(2015/10/29)
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- Organic electroluminescent device employing organic light emitting compound as light emitting material
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Provided is an organic electroluminescent device that exhibits an efficient host-dopant energy transfer mechanism, and thus, expresses a certain high-efficiency electroluminescent performance, based on improved electron density distribution. The organic electroluminescent device also overcomes low initial efficiency and short operation life property, and secures high-performance electroluminescent performance with high efficiency and long life property for each color.
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- Synthesis, characterization of a novel conjugated structural oligomer
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An octupolar star-shaped ladder-type oligomer composed of electron deriving from 1,3,5-triazine core end-capped by either an electron donating carbazolemoiety(TA(TL)-Ph(3)-CBZ) have been designed and synthesized to investigate the structure-properties relationship of highly efficient multiphoton absorbing materials. The newly synthesized molecules were characterized by 1H NMR, 13C NMR and mass spectrometry. Linear optical properties of the oligomer were investigated by UV-vis and fluorescence spectrometries, as well as the nonlinear optical properties were characterized by two-photon excited fluorescence (2PEF) measurement.
- An, Dong,Ye, Zhiwen
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p. 2971 - 2974
(2015/11/03)
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- Novel hole transport materials based on N,N′-disubstituted-dihydrophenazine derivatives for electroluminescent diodes
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A series of novel hole transport materials for organic light-emitting diodes (OLEDs) based on 9,14-diphenyl- 9,14-dihydrodibenzo[a,c]phenazine were synthesized and characterized by 1H NMR and 13C NMR, mass spectrometry and single crystal structure analysis methodologies. The crystal structures of three selected molecules reveal large dihedral angles between different functional units. The electro-optical properties of the materials were examined by UV-vis absorption, photoluminescence spectroscopy and cyclic voltammetry. The HOMO of the materials were between 4.83-5.08 eV, indicating a good match between the HOMO of indium tin oxide (ITO) and the HOMO of light-emitting layer, which renders the promising candidates as hole transport materials for organic light-emitting devices. In terms of the device with the structure of ITO/HTM (60 nm)/Alq3 (50 nm)/LiF (1 nm)/Al (200 nm), the device b using N,N-diphenyl-4′ -(14-phenyldibenzo[a,c]phenazin-9(14H)-yl)-[1,1′ -biphenyl]-4-amine presented a maximum luminance of 17 437 cd m-2 at 10.7 V and kept a high current efficiency (the maximum current efficiency is 2.25 cd A-1) at a high current density (>500 mA cm-2), which illustrates the exploited material possesses good hole transport and stable properties.
- Zheng, Zhiwen,Dong, Qingchen,Gou, Liao,Su, Jian-Hua,Huang, Jinhai
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supporting information
p. 9858 - 9865
(2015/02/02)
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- NOVEL ORGANIC ELECTROLUMINESCENCE COMPOUNDS AND ORGANIC ELECTROLUMINESCENCE DEVICE USING THE SAME
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The present invention relates to a novel organic luminescent compound and an organic electroluminescence device containing the same. The compounds according to the present invention have high luminous efficiency and long operation lifetime. Therefore, they can produce an organic electroluminescent device which improves power consumption.
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- Synthesis and characterization of highly stable and efficient star-molecules
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A series of well-defined star-shaped molecules have been synthesized by Pd-catalyzed Suzuki cross-coupling starting from very simple reactants with 1,3,5-trisubstituted benzene, 2,4,6-trisubstituted pyridine and trisubstituted phenylcarbazole as the backbones. These star-molecules are all soluble in common organic solvents and electrochemically stable with reversible cyclic voltammographs and high lying HOMOs. They exhibit excellent blue-fluorescence with quantum yield up to 0.87 and high glass transition temperatures. These molecules offer potential as pure blue-light emitting, hole-transport or host materials for optoelectronic applications.
- Huang, Hai-Fang,Xu, Shi-Hua,He, Yan-Bo,Zhu, Cai-Cai,Fan, He-Liang,Zhou, Xue-Hua,Gao, Xi-Cun,Dai, Yan-Feng
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p. 705 - 713
(2013/03/13)
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- Star-shaped ladder-type ter(p-phenylene)s for efficient multiphoton absorption
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Star-shaped ladder-type ter(p-phenylene)s exhibit remarkably efficient multiphoton absorption properties with 2PA cross-section up to 2579 GM at 700 nm and 3PA cross-section up to 3.35 × 10-76 cm6 s 2 in the femtosecond regime for a blue-emissive molecule despite having such a short π-conjugated framework.
- Guo, Lei,Li, King Fai,Wong, Man Shing,Cheah, Kok Wai
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p. 3597 - 3599
(2013/05/09)
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- Synthesis and biological activity of new 4-(Pyridin-4-yl)-(3-methoxy-5- methylphenyl)- 1H-pyrazoles derivatives as ROS Receptor tyrosine kinase inhibitors
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A series of new 4-(pyridin-4-yl)-(3-methoxy-5-methylphenyl)-1H-pyrazoles (6a-k & 7a-l) has been rationally designed based on the structure of the lead compound KIST301080, a selective ROS receptor tyrosine kinase inhibitor, in order to study the activity of ROS of this new class of inhibitors. The compounds were synthesized and screened against ROS kinase, where compound 6h showed moderate inhibitory activity with an IC50 value of 6.25 μM. The study emphasized the importance of the acetonitrile group at the pyrazole ring and also the importance of having a hydrogen bond donor on the distal phenyl ring linked to the pyridine moiety.
- Park, Byung Sun,El-deeb, Ibrahim M.,Yoo, Kyung Ho,Han, Dong Keun,Tae, Jin Sung,Lee, So Ha
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p. 3629 - 3634
(2013/01/16)
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- Anthracene derivatives and light-emitting devices using the anthracene derivatives
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The present invention provides novel anthracene derivatives. In particular, the present invention provides light-emitting elements with high luminous efficiency, and light-emitting elements with long lifetime. Further, the present invention provides light-emitting devices and electronic devices having long lifetime by using these light-emitting elements. An anthracene derivative represented by the general formula (1) is provided. In addition, since the anthracene derivative represented by the general formula (1) has high luminous efficiency, a light-emitting element using the anthracene derivative represented by the general formula (1) can also have high luminous efficiency. By using the anthracene derivative represented by the general formula (1), light-emitting elements with long lifetime can be provided.
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Page/Page column 180-181
(2012/10/23)
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- Novel multifunctional organic semiconductor materials based on 4,8-substituted 1,5-naphthyridine: Synthesis, single crystal structures, opto-electrical properties and quantum chemistry calculation
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A series of 4,8-substituted 1,5-naphthyridines (1a-1h) have been successfully synthesised by a Suzuki cross-coupling between 4,8-dibromo-1,5- naphthyridine (4) and the corresponding boronic acids (2a-2h) in the presence of catalytic palladium acetate in yields of 41.4-75.8% and have ben well characterized. They are thermally robust with high phase transition temperatures (above 186 °C). Compounds 1b, 1e and 1f crystallized in the monoclinic crystal system with the space groups P21/c, P21/c and P21/n, respectively. All of them show the lowest energy absorption bands (λmaxAbs: 294-320 nm), revealing low optical band gaps (2.77-3.79 eV). These materials emit blue fluorescence with λmaxEm ranging from 434-521 nm in dilute solution in dichloromethane and 400-501 nm in the solid state. 4,8-Substituted 1,5-naphthyridines 1a-1h have estimated electron affinities (EA) of (2.38-2.72 eV) suitable for electron-transport materials and ionization potentials (IP) of 4.85-5.04 eV facilitate excellent hole-injecting/hole-transport materials properties. Quantum chemical calculations using DFT B3LYP/6-31G* showed nearly identical the lowest unoccupied molecular orbitals (LUMO) of -2.39 to -2.19 eV and the highest occupied molecular orbitals (HOMO) of -5.33 to -6.84 eV. These results demonstrate the 4,8-substituted 1,5-naphthyridines 1a-1h with a simple architecture might be promising blue-emitting (or blue-green-emitting) materials, electron-transport materials and hole-injecting/hole-transport materials for applications for developing high-efficiency OLEDs.
- Wang, Kun-Yan,Chen, Chen,Liu, Jin-Fang,Wang, Qin,Chang, Jin,Zhu, Hong-Jun,Li, Chong
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p. 6693 - 6704
(2012/09/22)
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- Durene-decorated CBP derivatives as phosphorescent hosts and exciton-blocking materials for efficient blue OLEDs
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Two novel durene-containing molecules, 1,4-bis-[4-(9-carbazolyl)-phenyl]- durene (CPD) and 1,4-bis-{4-[9-(3,6-(di-tert-butyl)carbazoyl)]-phenyl}-durene (t-BuCPD), which are derived from 4,4′-bis(9-carbazolyl)biphenyl (CBP) by inserting durene in its biphenyl core, are designed and synthesized for use as host materials for blue phosphors in organic light-emitting diodes (OLEDs). Inserting durene in biphenyl causes a right-angle torsion between the durene and the adjacent phenyl groups due to the strong steric hindrance effect of the durene group, confining the effective π-conjugation on only one carbazole and one phenyl and increasing the triplet energies of CPD and t-BuCPD to over 3.0 eV. These durene-decorated molecules show higher thermal stabilities than many other CBP derivatives. Blue phosphorescent OLEDs were fabricated using CPD and t-BuCPD as triplet hosts and traditional iridium(iii)bis(4,6-(difluorophenyl) pyridinato-N,C2′)picolinate (Firpic) as a dopant and excellent performances were achieved. In particular, peak efficiencies of 26.2 cd A -1 and 14.8 lm W-1 were realized when CPD was used as both a host and exciton-blocking material. This is the first report using durene to tune the triplet energy levels of phosphorescent host materials.
- Deng, Lijun,Li, Jiuyan,Wang, Xinzeng,Zhang, Zhengchuan
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p. 19700 - 19708,9
(2020/08/31)
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- Benzoxazole derivative, and light-emitting element, light-emitting device, and electronic device using benzoxazole derivative
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Disclosed is a novel benzoxazole derivative which has high excitation energy, particularly high triplet excitation energy, and is a bipolar substance. A benzoxazole derivative represented by the following General Formula (G1) is provided. In the formula, R1 and R2 independently represent a hydrogen atom, an alkyl group with 1 to 4 carbon atoms, or a substituted or unsubstituted aryl group with 6 to 13 carbon atoms, substituents of the substituted aryl group may be bonded to form a ring which may form a spiro ring structure, R11 to R14 independently represent a hydrogen atom, a halogen, an alkyl group with 1 to 4 carbon atoms, or an unsubstituted aryl group with 6 to 10 carbon atoms, a bond formed between any two of α, β, and γ forms a carbazole skeleton, and n is 0 to 3.
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- Starburst dendrimers consisting of triphenylamine core and 9-phenylcarbazole-based dendrons: Synthesis and properties
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Novel dendrimers consisting of a triphenylamine core and 1st to 3rd generations of 9-phenylcarbazole-based dendrons were synthesized by Suzuki coupling reaction through convergent approach. Their structures were confirmed by two-dimensional correlated H-H COSY and C-H HSQC NMR spectra, MALDI-TOF MS and elemental analysis. The dendrimers exhibit excellent thermal stability with 5% weight loss temperatures over 540 °C. The computer modeling reveals that the dendrons in dendrimers greatly twisted with the generation, leading to the dendrimers decreased crystalline ability. Of interest is the observation that, for an identical dendrimer, the solid film displays the similar UV absorption and luminescence emission profiles to the solution sample, indicating that, after evaporation of solvent, the rigid dendrimer can well maintain its conformational morphology and the aggregation or stacking of the chromophoric groups is significantly inhibited. All the dendrimers can emit intense fluorescence with narrow full width at half maximum (FWHM) around 46-50 nm. Moreover, with the incremental generation, the quantum efficiencies remarkably increase from 64 to 95%, suggesting that the highly contorted and bulky dendrons effectively decrease energy wastage and non-radiative decay. The synergistic effect of electron-donating triphenylamine core and 9-phenylcarbazole-based dendrons results in the HOMO energy level of -5.36 eV for the 3rd-generation dendrimer, very close to the work function of the ITO/PEDOT electrode (-5.2 eV), which characteristic is very advantageous for the hole injection and transport materials.
- You, Jia,Li, Guiyang,Wang, Zhonggang
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p. 9481 - 9490
(2013/01/15)
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- Synthesis, structure, photophysical and electrochemical properties of series of new fac-triscyclometallated iridium complexes with carbazole or oxadiazole moieties
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A series of new fac-triscyclometallated iridium complexes Ir(Ln) 3 (n = 1-6) (L1: 2-{4-[5-phenyl-[1,3,4]oxadiazol-2-yl]- phenyl}-pyridine, L2: 2-{4-[5-(4-tert-butyl-phenyl)-[1,3,4] oxadiazol-2-yl]- phenyl}-pyridine, L3: 9-(4-pyridin-2-yl-phenyl)-9H-carbazole, L4: 1-[4-(5-phenyl-[1,3,4]oxadiazol-2-yl)-phenyl]-isoquinoline, L5: 1-{4-[5-(4-tert-butyl-phenyl)-[1,3,4] oxadiazol-2-yl]-phenyl}-isoquinoline, L6: 9-(4-isoquinolin-1-yl-phenyl)-9H-carbazole) based on Ir(ppy)3 (ppy = phenyl-pyridine) and Ir(piq)3 (piq = 1-phenylisoquinoline) were synthesized from Ir(acac)3 and corresponding ligands by a new and effective way using anthracene as a solvent. Single-crystal X-ray diffraction spectra of three complexes were studied and the iridium centers were found to adopt distorted octahedral coordination geometry. UV-Vis, photoluminescence, cyclic voltammetry were employed for studying the photophysical and electrochemical properties. These complexes exhibit intense phosphorescence in toluene solution at room temperature with high quantum efficiencies (0.07-0.58) and submicrosecond lifetimes (0.57-0.87 μs).
- Xu, Qiu-Lei,Li, Hong-Yan,Wang, Cheng-Cheng,Zhang, Song,Li, Tian-Yi,Jing, Yi-Ming,Zheng, You-Xuan,Huang, Wei,Zuo, Jing-Lin,You, Xiao-Zeng
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- NOVEL ORGANIC ELECTROLUMINESCENT COMPOUNDS AND ORGANIC ELECTROLUMINESCENT DEVICE USING THE SAME
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Provided are novel organic electroluminescent compounds and organic electroluminescent devices using the same. Since the organic electroluminescent compound exhibits good luminous efficiency and excellent life property compared to the existing material, it may be used to manufacture OLED devices having superior operation life and consuming less power due to improved power efficiency.
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- Carbazole and arylamine functionalized iridium complexes for efficient electro-phosphorescent light-emitting diodes
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We report the synthesis and characterization of four cyclometalated iridium complexes based on carbazole and arylamine modified 2-phenylpyridine. The carbazole and arylamine groups are linked to 2-phenyl pyridine backbone to enhance the energy harvesting and transfer from host to guest materials. The electrochemical and photophysical properties of the complexes are studied and electroluminescent devices are fabricated. The results show that the complexes with ligands containing carbazole moieties have desirable phosphorescent properties. The device with complex 3 doped PVK (poly (vinylcarbazole)) as emission layer achieves maximum luminous efficiency of 6.56 cd A-1 and maximum brightness of 14448 cd m-2.
- Wang, Dan,Wang, Jian,Fan, He-Liang,Huang, Hai-Fang,Chu, Zeng-Ze,Gao, Xi-Cun,Zou, De-Chun
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p. 340 - 345
(2011/05/12)
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- AROMATIC AMINE DERIVATIVE AND ORGANIC ELECTROLUMINESCENT ELEMENT
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Provided are a long-lifetime organic electroluminescence device which can be fabricated in an improved yield owing to suppressed crystallization of molecules, and an aromatic amine derivative that realizes the device, i.e. , a novel aromatic amine derivative having a specific structure. Specifically provided are an organic electroluminescence device, including an organic thin film layer formed of one or more layers including at least a light emitting layer, the organic thin film layer being interposed between a cathode and an anode, and an aromatic amine derivative for at least one layer of the organic thin film layer, in particular, a hole transporting layer, the derivative having at least one such structure that a substituent in which two or more specific heterocycles are linked to each other, in particular, a substituent in which two or more specific heterocycles are linked through an aryl group is bonded to an amine through an aryl group.
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Page/Page column 28; 38
(2012/01/11)
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- Pyrene-cored dendrimer with carbazole derivatives as dendrons: Synthesis, properties and application in white light-emitting diode
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A new dendrimer using pyrene as core and carbazole derivative as dendron has been successfully prepared via Suzuki coupling reaction. Its chemical structure was confirmed through 1H NMR, elemental analysis and MALDI-TOF MS methods. The dendrimer synthesized possessed excellent thermal stability with initial decomposition temperature over 470 °C and high fluorescence quantum yield of 86%. The luminescence spectra showed that, relative to the solution sample, the emission peaks of the solid dendrimer film were apparently broadened and red-shifted, indicating the strong π-π stacking effect between the pyrene moieties. By doping 1.5% of the dendrimer in 4,4′-bis[N-(1-naphthyl)-N-phenylamino]biphenyl (NPB), a light-emitting diode device was fabricated in the ITO/NPB/NPB:dendrimer (1.5%)/TPBI/Mg:Ag configuration, which emitted a white color with Commission Internationale de L'Eclairage (CIEx,y) coordinates of (0.29, 0.34) and a maximum brightness of 1300 cd m-2, exhibiting promising potential in white light-emitting diode application. This journal is the Owner Societies.
- You, Jia,Li, Guiyang,Wang, Renjie,Nie, Qiuping,Wang, Zhonggang,Li, Jiuyan
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experimental part
p. 17825 - 17830
(2012/07/17)
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- Stable, glassy, and versatile binaphthalene derivatives capable of efficient hole transport, hosting, and deep-blue light emission
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Organic light-emitting diodes (OLEDs) have great potential applications in display and solid-state lighting. Stability, cost, and blue emission are key issues governing the future of OLEDs. The synthesis and photoelectronics of a series of three kinds of binaphthyl (BN) derivatives are reported. BN 1-3 are "melting-point-less" and highly stable materials, forming very good, amorphous, glass-like films. They decompose at temperatures as high as 485-545 °C. At a constant current density of 25 mA cm -2, an ITO/BN3/Al single-layer device has a much-longer lifetime (>80 h) than that of an ITO/NPB/Al single-layer device (8 h). Also, the lifetime of a multilayer device based on BN1 is longer than a similar device based on NPB. BNs are efficient and versatile OLED materials: they can be used as a hole-transport layer (HTL), a host, and a deep-blue-light-emitting material. This versatility may cut the cost of large-scale material manufacture. More importantly, the deep-blue electroluminescence (emission peak at 444 nm with CIE coordinates (0.16, 0.11), 3.23 cd A-1 at 0.21 mA cm-2, and 25200cd m-2 at 9V) remains very stable at very high current densities up to 1000 mA cm -2.
- Wei, Bin,Liu, Ji-Zhong,Zhang, Yong,Zhang, Jian-Hua,Peng, Hua-Nan,Fan, He-Liang,He, Yan-Bo,Gao, Xi-Cun
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p. 2448 - 2458
(2011/11/30)
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- Benzoxazole Derivative, and Light-Emitting Element, Light-Emitting Device, and Electronic Device Using Benzoxazole Derivative
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Disclosed is a novel benzoxazole derivative which has high excitation energy, particularly high triplet excitation energy, and is a bipolar substance. A benzoxazole derivative represented by the following General Formula (G1) is provided. In the formula, R1 and R2 independently represent a hydrogen atom, an alkyl group with 1 to 4 carbon atoms, or a substituted or unsubstituted aryl group with 6 to 13 carbon atoms, substituents of the substituted aryl group may be bonded to form a ring which may form a spiro ring structure, R11 to R14 independently represent a hydrogen atom, a halogen, an alkyl group with 1 to 4 carbon atoms, or an unsubstituted aryl group with 6 to 10 carbon atoms, a bond formed between any two of α, β, and γ forms a carbazole skeleton, and n is 0 to 3.
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- Stilbene derivative, light emitting element, light emitting device, and electronic appliance
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An object is to provide a novel substance which exhibits blue light emission with excellent color purity, and to provide a light emitting element and a light emitting device using the novel substance. A stilbene derivative represented by the general formula (G1) is provided. Note that in the general formula (G1), each of A1 and B1 represents any one of structures represented by the following general formulae (G1-1) to (G1-4). In addition, in each of the general formulae (G1-1) to (G1-4), each of R1 to R24 represents any one of hydrogen and an alkyl group having 1 to 4 carbon atoms. Such a stilbene derivative can exhibit blue light emission with excellent color purity.
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Page/Page column 78; 79
(2010/08/04)
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- METHOD FOR SYNTHESIZING ANTHRACENE DERIVATIVE AND ANTHRACENE DERIVATIVE, LIGHT EMITTING ELEMENT, LIGHT EMITTING DEVICE, ELECTRONIC DEVICE
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It is an object to provide a novel method for synthesizing an anthracene derivative with the small number of steps. It is another object to provide a novel anthracene derivative. It is further another object to provide a light-emitting element, a light-emitting device, and an electronic device, each using the anthracene derivative. A method for synthesizing an anthracene derivative represented by a general formula (1) is provided by coupling a 9-arylanthracene derivative having an active site at a 10-position with a 9-arylcarbazole derivative having an active site in an aryl group using metal, a metal compound, or a metal catalyst.
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Page/Page column 76-77
(2010/11/30)
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- Organic compound, anthracene derivative, and light-emitting element, light-emitting device, and electronic device using anthracene derivative
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Objects of the present invention are to provide novel anthracene derivatives and novel organic compounds; a light-emitting element that has high emission efficiency; a light-emitting element that is capable of emitting blue light with high luminous efficiency; a light-emitting element that is capable of operation for a long time; and a light-emitting device and an electronic device that have lower power consumption. An anthracene derivative represented by a general formula (1) and an organic compound represented by a general formula (17) are provided. A light-emitting element that has high emission efficiency can be obtained by use of the anthracene derivative represented by the general formula (1). Further, a light-emitting element that has a long life can be obtained by use of the anthracene derivative represented by the general formula (1).
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Page/Page column 282
(2008/12/08)
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- Stilbene Derivative, Light Emitting Element, Light Emitting Device, and Electronic Appliance
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An object is to provide a novel substance which exhibits blue light emission with excellent color purity, and to provide a light emitting element and a light emitting device using the novel substance. A stilbene derivative represented by the general formula (G1) is provided. Note that in the general formula (G1), each of A1 and B1 represents any one of structures represented by the following general formulae (G1-1) to (G1-4). In addition, in each of the general formulae (G1-1) to (G1-4), each of R1 to R24 represents any one of hydrogen and an alkyl group having 1 to 4 carbon atoms. Such a stilbene derivative can exhibit blue light emission with excellent color purity.
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- Synthesis and properties of 3,8-bis[4-(9H-carbazol-9-yl)phenyl]-1,10- phenanthroline for phosphorescent OLEDs
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A novel bipolar molecule, 3,8-bis[4-(9H-carbazol-9-yl)-phenyl]-1,10- phenanthroline (CZPT) was synthesized and employed as the host in phosphorescent organic light-emitting devices (OLEDs). A maximum luminance of 7000 cd/m 2 was achieved using fac-tris(2-phenylpyridine)iridium (Ir(ppy) 3) as the emitting material. Copyright
- Ge, Ziyi,Hayakawa, Teruaki,Ando, Shinji,Ueda, Mitsuru,Akiike, Toshiyuki,Miyamoto, Hidetoshi,Kajita, Toru,Kakimoto, Masa-aki
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p. 262 - 263
(2008/09/20)
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