- Modulation of the Physicochemical Properties of Donor–Spiro–Acceptor Derivatives through Donor Unit Planarisation: Phenylacridine versus Indoloacridine—New Hosts for Green and Blue Phosphorescent Organic Light-Emitting Diodes (PhOLEDs)
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This work reports a detailed structure–property relationship study of a series of efficient host materials based on the donor–spiro–acceptor (D-spiro-A) design for green and sky-blue phosphorescent organic light-emitting diodes (PhOLEDs). The electronic and physical effects of the indoloacridine (IA) fragment connected through a spiro bridge to different acceptor units, namely, fluorene, dioxothioxanthene or diazafluorene moiety, have been investigated in depth. The resulting host materials have been easily synthesised through short, efficient, low-cost, and highly adaptable synthetic routes by using common intermediates. The dyes possess a very high triplet energy (ET) and tuneable HOMO/LUMO levels, depending on the strength of the donor/acceptor combination. The peculiar electrochemical and optical properties of the IA moiety have been investigated though a fine comparison with their phenylacridine counterparts to study the influence of planarisation. Finally, these molecules have been incorporated as hosts in green and sky-blue PhOLEDs. For the derivative SIA-TXO2as a host, external quantum efficiencies as high as 23 and 14 % have been obtained for green and sky-blue PhOLEDs, respectively.
- Thiery, Sébastien,Tondelier, Denis,Geffroy, Bernard,Jeannin, Olivier,Rault-Berthelot, Jo?lle,Poriel, Cyril
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Read Online
- Enabling high efficiency and long lifetime of pure blue phosphorescent organic light emitting diodes by simple cyano modified carbazole-based host
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Herein, we report two simple and efficient high triplet energy bipolar host materials named 2'-(9H-carbazol-9-yl)-[1,1′-biphenyl]-2-carbonitrile (CzBPCN) and 9-(2′-cyano-[1,1′-biphenyl]-2-yl)-9H-carbazole-3-carbonitrile (CNCzBPCN) by connecting carbazole type donor and cyano acceptor on 2 and 2′ positions of a biphenyl linker, respectively. The effect of cyano substitution on carbazole building block on photophysical and electroluminescence properties was unveiled. Both the compounds revealed high triplet energy (ET) of above 3.0 eV attributed to the interrupted interchromophoric electronic interactions between the donor and acceptor units. The computational studies and carrier transport analysis proved that the compounds secured good bipolar charge transporting feature. The applicability of these materials as hosts for blue phosphorescent organic light emitting diodes (PhOLEDs) was tested. Interestingly, the CNCzBPCN hosted device exhibited superior performance with three fold improved external quantum efficiency (EQEmax) of 20.2% over the CzBPCN hosted device which showed EQEmax of 7.1%. Importantly, the CNCzBPCN hosted device demonstrated 11 fold extended operational lifetime of 121 h up to 50% of its intimal luminance (L0 = 200 cd/m2) compared to CzBPCN. We believe that this work demonstrates the cost-effective and efficient high triplet energy bipolar host materials for simultaneous achievement of high EQE over 20% and long operational lifetime of blue PhOLEDs.
- Chung, Won Jae,Konidena, Rajendra Kumar,Lee, Jun Yeob
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Read Online
- Spiro?type TADF emitters based on acridine donors and anthracenone acceptor
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Two rigid spiro-type TADF emitters (CBZANQ, PXZANQ) were designed and synthesized via a two-step route. CBZANQ and PXZANQ both contain an anthracenone acceptor along with a carbazole?acridine-fused donor and a phenoxazine?acridine-fused donor, respectively, where each donor and acceptor are linked by a spiro bridge to form D-σ-A structures with an orthogonal arrangement. Both CBZANQ and PXZANQ have the difference between the singlet and triplet energy values (ΔEST) of 0.05 eV and 0.03 eV, respectively, which are sufficiently small for efficient triplet harvesting. CBZANQ with a weak electron donor (carbazole) exhibited a weak intramolecular charge transfer (ICT) character, resulting in a low photoluminescence quantum yield (PLQY) of 18%. On the other hand, when combined with a strong electron donor (phenoxazine), PXZANQ exhibited a strong ICT character, resulting in a high PLQY of 71%. Organic light-emitting diode (OLED) devices based on CBZANQ emitter and bis[2-(diphenylphosphino)phenyl] ether oxide (DPEPO) host exhibited sky-blue electroluminescence (EL) at 492 nm with a low external quantum efficiency (EQE) of 6.7%. Conversely, the OLED devices fabricated using PXZANQ emitter and DPEPO host exhibited green emission at 528 nm, along with a high EQE of 22.1%. Additionally, the efficiency of PXZANQ-based devices remained high at high luminance, indicating relatively small efficiency roll-off (13.9% EQE under 500 cd/m2).
- Hong, Jong-In,Huh, Jin-Suk,Yang, Dongwook
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- Composition For Capping Layer of Organic Light Emitting Diode and Organic Light Emitting Diode Having The Same
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The present invention relates to an organic electroluminescent device, and more particularly, to an indolocarbazole derivative compound used as a material for a capping layer (CPL) of the organic electroluminescent device. More specifically, the present invention relates to an indolocarbazole derivative compound having an amine substituent, a composition for the CPL of the organic electroluminescent device comprising the same, and the organic electroluminescent device comprising the same.
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Paragraph 0178-0182
(2021/02/16)
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- Organic Light Emitting Material and Organic Light Emitting Diode Having The Same
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The present invention relates to a compound derivative for an organic electroluminescent device and an organic electroluminescent device using the same. The present invention relates to an aromatic compound including an indolocarbazolyl group and a spirobifluorenyl group, and more particularly, to an aromatic compound including an indolocarbazolyl group and a spirobifluorenyl group.
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Paragraph 0104-0107
(2021/11/02)
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- Hole transport type main body material, preparation method thereof and application of hole transport type main body material in preparation of organic electroluminescent device
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The invention belongs to the technical field of organic photoelectric materials, and discloses a hole transport type main body material, a preparation method thereof and an application of the hole transport type main body material in preparation of an organic electroluminescent device. The hole transport type main body material has a structural formula as shown in a formula (I). The hole transport material provided by the invention has high hole transport capability, can be applied to a hole layer of an organic electroluminescent device or can be combined with an electron transport material to form an exciplex as a luminescent layer or a main body material in the luminescent layer, and realizes relatively high device efficiency. The hole transport material disclosed by the invention has relatively high stability, can be applied to an exciplex main body, and effectively realizes an electroluminescent device with relatively long service life.
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Paragraph 0048-0053
(2021/08/07)
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- Impact of the donor structure in new D-π-A systems based on indolo[3,2,1-jk]carbazoles on their thermal, electrochemical, optoelectronic and luminescence properties
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In this work, novel fluorophores with D-π-A architectures (ICz-1-ICz-6) were synthesized and investigated, where the indolo[3,2,1-jk]carbazole (ICz) framework is connected by an ethylene bridge with extensive donor moieties -e.g., fluorene, carbazole, phenothiazine, methoxyphenyl, bithiophene, and dibenzothiophene. The influences of the donor character of the substituents in the indolocarbazole derivatives on their thermal, optical and electrochemical properties were explored and compared with the quantum chemical calculations based on DFT and TD-DFT. AllICz-1-ICz-6compounds emit blue light with emission peaks between 390 and 430 nm in solution, except for compoundICz-5with a strong phenothiazine donor, which emits light at 463 nm. TheICz-6derivative with the dibenzothiophene unit features an exception to Kasha's rule. For the selected compoundsICz-2,ICz-4, andICz-5, preliminary electroluminescence tests were performed, both based on devices with a neat compound (ITO/PEDOT:PSS/ICz/Al) and with a guest-host configuration (ITO/PEDOT:PSS/PVK:PBD:ICz/Al), where two emission bands were detected covering the range from 400 to over 900 nm. Additionally, several multilayer OLED devices (ITO/PEDOT:PSS/poly-TPD/ICz-2-5/TPBi/LiF/Al) were prepared, and all diodes showed electroluminescence at 570 nm.
- Goriachiy, Dmitry,Ma?kowski, Sebastian,Schab-Balcerzak, Ewa,Siwy, Mariola,Slodek, Aneta,Sulowska, Karolina,Szafraniec-Gorol, Gra?yna,Taydakov, Ilya,Vasylieva, Marharyta,Zych, Dawid
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p. 7351 - 7362
(2021/06/22)
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- COMPOUND, MATERIAL FOR ORGANIC ELECTROLUMINESCENT ELEMENTS, ORGANIC ELECTROLUMINESCENT ELEMENT, AND ELECTRONIC DEVICE
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A compound represented by formula (1) provides an organic electroluminescence device having lifetime further improved: wherein R1 to R9, R11 to R18, R21 to R27, Ar, L1, L2, and L3 are as defined in the description.
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Paragraph 0201-0202
(2021/04/02)
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- Efficient organic light-emitting diodes based on iridium(iii) complexes containing indolo[3,2,1-jk]carbazole derivatives with narrow emission bandwidths and low efficiency roll-offs
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In this work, two cyclometalated ligands 2-(pyridin-2-yl)indolo[3,2,1-jk]carbazole (pyidcz) and 2-(4-(trifluoromethyl)pyridin-2-yl)indolo[3,2,1-jk]carbazole (tfpyidcz) containing an indolo[3,2,1-jk]carbazole unit were synthesized for achieving highly efficient iridium(iii) complexes (pyidcz)2Ir(tmd) and (tfpyidcz)2Ir(tmd) (tmd = 2,2,6,6-tetramethyl-3,5-heptanedione). The two Ir(iii) complexes exhibit emissions peaking at 499 and 554 nm, respectively, with narrow full width at half maximum (FWHM) values of 35 and 53 nm, respectively, short phosphorescence lifetimes less than 1 μs and high photoluminescence quantum yields of up to 90% in CH2Cl2solution. The organic light-emitting diodes (OLEDs) with (pyidcz)2Ir(tmd) and (tfpyidcz)2Ir(tmd) emitters show good performances. The (pyidcz)2Ir(tmd)-based device shows a turn-on voltage (Von) of 3.6 V with a maximum brightness (Lmax) of 39123 cd m?2, a maximum current efficiency (ηc,max) of 69.2 cd A?1, a maximum power efficiency (ηp,max) of 36.8 lm W?1and a maximum external quantum efficiency (EQEmax) of 21.2%. In particular, the FWHM bandwidth of the electroluminescence spectrum is only 33 nm, which was rarely reported for Ir(iii) complex-based OLEDs. The performance of the (tfpyidcz)2Ir(tmd)-based device is slightly better with aVonof 3.3 V, aLmaxof 31714 cd m?2, aηc,maxof 78.4 cd A?1, aηp,maxof 54.7 lm W?1and an EQEmaxof 24.0%. Furthermore, the efficiency roll-offs of both devices are small, and theηcvalues at 10?000 cd m?2brightness are still maintained at 60.0 and 71.4 cd A?1, respectively, which provide a powerful reference for developing indolo[3,2,1-jk]carbazole-based Ir(iii) complexes for efficient OLEDs.
- Liao, Xiang-Ji,Lu, Jun-Jian,Luo, Xu-Feng,Yan, Zhi-Ping,Yuan, Li,Zhang, Yi-Pin,Zheng, You-Xuan,Zhu, Jin-Jun
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p. 8226 - 8232
(2021/07/13)
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- ORGANIC MOLECULES FOR OPTOELECTRONIC DEVICES
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The invention relates to an organic compound, in particular for the application in optoelectronic devices. According to the invention, the organic compound has a first chemical moiety with a structure of formula I, and two second chemical moieties, each independently from another with a structure of formula II, wherein the first chemical moiety is linked to each of the two second chemical moieties via a single bond; wherein T, V is selected from the group consisting of RA and R1;W, X, Y is the binding site of a single bond linking the first chemical moiety to one of the two second chemical moieties or is selected from the group consisting of RA and R2;RA has a structure of Formula Py: which is bonded to the structure of Formula I via the position marked by the dotted line; and RW, RX, RY is the binding site of a single bond linking the first chemical moiety to one of the two second chemical moieties or is RI.
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Paragraph 0313; 0314; 0349; 0352; 0356; 0360
(2021/01/21)
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- Combined experimental and density functional theory studies on novel 9-(4/3/2-cyanophenyl)-9H-carbazole-3-carbonitrile compounds for organic electronics
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We have synthesized a series of novel hybrid molecules 9-(2-cyanophenyl)-9H-carbazole-3-carbonitrile (o-CNCbzCN), 9-(3-cyanophenyl)-9H-carbazole-3-carbonitrile (m-CNCbzCN) and 9-(4-cyanophenyl)-9H-carbazole-3-carbonitrile (p-CNCbzCN), comprising electron-donating carbazole and electron-accepting nitrile groups. Three positional isomers were synthesized with a view to tune photophysical and electrochemical properties of the hybrids. The photophysical study displayed absorption maxima in the range of 281–340 nm and 277–298 nm whereas emission maxima in the range of 349–366 nm and 366–369 nm in toluene and dimethylformamide (DMF), respectively. These molecules demonstrated suitable frontier molecular orbital (FMO) energy levels and ensure good thermal and morphological stability. Among these synthesized molecules, m-CNCbzCN showed very high decomposition temperature (Td = 341°C) whereas p-CNCbzCN exhibited good glass transition (Tg = 182°C) as well as melting temperature (Tm = 236°C), indicating its significant stability and potential utility as a bipolar host material for efficient phosphorescent organic light-emitting diodes (PhOLEDs).
- Patil, Bhausaheb,Lade, Jatin,Sathe, Pratima,Tripathi, Anuj,Pownthurai,Chetti, Prabhakar,Jadhav, Yogesh,Chaskar, Atul
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- Method for synthesizing N-aryl carbazole compound by catalyzing reaction of carbazole with aryl hydrazine by using transition metal
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The invention relates to a method for synthesizing an N-aryl carbazole compound by catalyzing reaction of carbazole with aryl hydrazine through transition metal. According to the method, a transitionmetal salt is used as a catalyst, a carbazole compound and an aryl hydrazine compound are used as reaction substrates, the reaction substrates and an alkali compound are added into a solvent for a reaction for a certain period of time to obtain a reaction solution, and the reaction solution is separated and purified to obtain the N-aryl carbazole compound. According to the method, low-boiling-point acetonitrile is used as a reaction solvent, so post-reaction treatment is easy to carry out; oxygen in the air serves as an oxidizing agent, so reaction conditions are environmentally friendly and safe, cost is low, and excessive oxidation is avoided; an aryl hydrazine compound is used as an arylation reagent, and reaction byproducts only comprise water and nitrogen, so the method is environment-friendly and pollution-free; the transition metal salt is used as the catalyst, the activity of the transition metal salt is high, the use of equivalent noble metals is avoided, and synthesis cost isreduced; and generally speaking, the synthesis method is friendly to environment, simple in process, good in reaction selectivity and high in yield, and has a relatively strong industrial applicationprospect.
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Paragraph 0061-0064; 0100
(2020/12/14)
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- Organic Light Emitting Material and Organic Light Emitting Diode Having The Same
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The present invention relates to a compound derivative used in an organic electroluminescent device, and an organic electroluminescent device using the same. More particularly, the present invention relates to an indolocarbazole derivative compound having an amine substituent. When using the indolocarbazole derivative compound as a light emitting material for an organic layer of an organic electroluminescent device, an effect of deriving high luminous efficiency even with a low driving voltage can be provided.(AA) Negative electrode(BB) Electron injection layer(CC) Electron transport layer 2(DD) Electron transport layer 1(EE) Light emission layer(FF) Electron suppression layer(GG) Hole transport layer(HH) Hole injection layer(II) Positive electrode(JJ) SubstrateCOPYRIGHT KIPO 2021
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Paragraph 0094; 0098-0099
(2020/09/16)
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- COMPOUND, MATERIAL FOR ORGANIC ELECTROLUMINESCENCE ELEMENT, ORGANIC ELECTROLUMINESCENCE ELEMENT, AND ELECTRONIC DEVICE
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A novel compound represented by formula (1): wherein R1 to R7, R11 to R18, L1 to L3, a to c, n, and Ar are as defined in the description, provides an organic electroluminescence device having a device lifetime further improved.
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Paragraph 0320-0321
(2020/02/10)
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- COMPOUND, MATERIAL FOR ORGANIC ELECTROLUMINESCENT ELEMENT, ORGANIC ELECTROLUMINESCENT ELEMENT, AND ELECTRONIC DEVICE
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A compound represented by formula (1): wherein R1 to R7, R11 to R18, L1 to L3, a to c, n, and Ar are as defined in the description, provides an organic electroluminescence device having an emission efficiency and a device lifetime further improved.
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Paragraph 0355; 0356
(2020/12/25)
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- Facile Assembly of Carbazolyl-Derived Phosphine Ligands and Their Applications in Palladium-Catalyzed Sterically Hindered Arylation Processes
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Phosphine ligands embodying a carbazolyl motif have been found to be successful in many palladium-catalyzed biaryl syntheses and direct C-H bond arylation processes. Here, a practical scaled-up synthesis of a series of carbazolyl-derived phosphine ligands, the PhenCarPhos series, is described. The original protocol for accessing the target ligand skeleton via aromatic C-N bond formation is limited by the use of a substoichiometric amount of copper salt and diamine catalysts, which both add cost and generate purification problems (significant amounts of side products and copper residues). In order to develop a more attractive and scalable synthetic pathway, a simple nucleophilic substitution method was attempted involving simple heating of 1-bromo-2-fluorobenzene, a carbazole derivative, and KOH in DMF without inert atmosphere protection. This route enables the large-scale synthesis of the desired ligand skeletons and minimizes the association of inseparable reduction side products. Particular examples of the use of these ligands in Pd-catalyzed sterically hindered arylation processes are also shown.
- Leung, Man Pan,Choy, Pui Ying,Lai, Wing In,Gan, Kin Boon,Kwong, Fuk Yee
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p. 1602 - 1609
(2019/08/20)
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- Indolo[3, 2, 1-jk]carbazole derivative, preparation method and application thereof, and electronic device
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The invention relates to an indolo[3, 2, 1-jk]carbazole derivative, a preparation method and application thereof, and an electronic device. The indolo[3, 2, 1-jk]carbazole derivative has a hole mobility up to 6.5*10cmVS, also can be applied as a hole transport material in solar cell devices, and can effectively inhibit energy consumption and improve the energy conversion efficiency, device life, electric current density, filling factor, threshold voltage and other performance of solar cell devices.
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Paragraph 0063; 0064
(2019/10/04)
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- COMPOUND AND ORGANIC ELECTRONIC DEVICE COMPRISING THE SAME
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The present invention relates to compounds represented by chemical formula I, and organic electronic devices comprising the same. The compound according to one embodiment of the present invention is used in an organic electronic device including an organic light emitting device, to lower the driving voltage of the organic electronic device, improve the light efficiency, and improve the lifetime characteristics of the device by the thermal stability of the compound.COPYRIGHT KIPO 2018
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Paragraph 0243; 0264-0267
(2018/05/03)
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- Novel carbazole derivatives designed by an: Ortho -linkage strategy for efficient phosphorescent organic light-emitting diodes
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Two novel carbazole derivatives 2′-(9H-carbazol-9-yl)-[1,1′-biphenyl]-4-carbonitrile (CNPhCz) and 2′-(9H-carbazol-9-yl)-[1,1′:3′,1′′-terphenyl]-4,4′′-dicarbonitrile (DCNPhCz) were designed and prepared as host materials for phosphorescent organic light-emitting diodes (PHOLEDs). CNPhCz and DCNPhCz were synthesized by an ortho-linkage strategy. In CNPhCz, one cyanophenyl and one carbazole unit were attached to the central benzene ring at the neighboring positions, while in DCNPhCz the carbazole group was surrounded by two cyanophenyl groups. The influence of different numbers of electron-withdrawing groups in these host materials on the charge-transport behavior and OLED device performance was studied systematically. Blue and green PHOLEDs based on these hosts were fabricated using common device structures with bis(4,6-(difluorophenyl)pyridinato-N,C2′)picolinate iridium(iii) (FIrpic) and bis(2-phenylpyridine) (acetylacetonate)iridium(iii) (Ir(ppy)2(acac)) as the dopants, respectively. The results indicated that the material with a smaller number of electron-withdrawing cyanobenzene groups (CNPhCz) showed better green PHOLED device performance with maximum efficiencies of 88.0 cd A-1, 86.1 lm W-1 and 24.4%.
- Liu, Xiang-Yang,Ge, Hui-Ting,Zhao, Yue,Zhao, Danli,Fan, Jian,Liao, Liang-Sheng
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p. 4300 - 4307
(2018/04/26)
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- A pyrimidine derivatives and application thereof (by machine translation)
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The invention discloses a pyrimidine derivative and its application, the pyrimidine derivatives having the following -like type (I) indicated by the structure; wherein said R1 , R2 , R3 Are selected from the carbon atom number is 1 - 60 alkyl, substituted and non-substituted aromatic heterocyclic radical, and substituted and non-substituted aromatic ring in base of any one group. The invention through the pyrimidine derivatives key chemical structure and the like is improved, and the pyrimidine derivatives as material is applied to the electro-luminescent layer in the organic electroluminescent device, compared with the prior art can effectively solve the organic electroluminescent device in blue light material of poor stability, low efficiency and the like. (by machine translation)
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Paragraph 0035; 0064; 0073; 0074
(2018/07/30)
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- COMPOUND, MATERIAL FOR ORGANIC ELECTROLUMINESCENCE DEVICES, ORGANIC ELECTROLUMINESCENCE DEVICE, AND ELECTRONIC DEVICE
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A compound represented by formula (1): wherein each symbol is as defined in the specification, provides a high performance organic electroluminescence device which comprises a cathode, an anode and an organic layer between the cathode and the anode, wherein the organic layer comprises a light emitting layer and at least one layer of the organic layer comprises the compound.
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Paragraph 0189-0191
(2018/07/15)
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- ORGANIC ELECTROLUMINESCENCE DEVICE AND ELECTRONIC DEVICE
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A compound represented by formula (1): wherein R1 to R8, R12 to R18, R21 to R25, R31 to R48, L1 to L3, and Ar are as defined in the specification, provides a high performance organic electroluminescence device which comprises a cathode, an anode and an organic layer between the cathode and the anode, wherein the organic layer comprises a light emitting layer and at least one layer of the organic layer comprises the compound.
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Paragraph 0212-0213
(2018/07/15)
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- COMPOUND, MATERIAL FOR ORGANIC ELECTROLUMINESCENT ELEMENT, ORGANIC ELECTROLUMINESCENT ELEMENT, AND ELECTRONIC APPARATUS
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PROBLEM TO BE SOLVED: To provide a compound that creates an organic EL element showing excellent organic EL performance, an organic EL element containing the compound and showing excellent organic EL performance, and an electronic apparatus containing the organic EL element. SOLUTION: The present invention provides an organic EL element containing, for example, compound 1, and an electronic apparatus containing the organic EL element. SELECTED DRAWING: None COPYRIGHT: (C)2018,JPO&INPIT
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Paragraph 0227-0228
(2018/08/02)
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- Synthesis method of photoelectric material intermediate 9-(4'-chlorobiphenyl-2-yl) carbazole
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The invention discloses a synthesis method of a photoelectric material intermediate 9-(4'-chlorobiphenyl-2-yl) carbazole, and belongs to the field of organic chemical synthesis. According to the method, 9-(2-bromophenyl) carbazole is synthesized from carbazole and o-dibromobenzene as raw materials, and then reacts with 4-chlorophenylboronic acid to synthesize a target compound. In synthesis of the intermediate 9-(2-bromophenyl) carbazole, the o-dibromobenzene is taken as a reaction material and is also taken as a reaction solvent, and L-lysine is taken as a catalyst ligand, so that the reaction rate is improved, the post-treatment step is simplified, the production cost is reduced, and industrial production is facilitated.
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Paragraph 0014; 0015
(2017/08/29)
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- Synthesis and electroluminescence properties of new blue dual-core OLED emitters using bulky side chromophores
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Using a 1-anthracen-9-yl-pyrene (AP) dual-core emitter, two new emitters of blue light, 1-spiro-9,9′-bifluoren-4-yl-6-(10-spiro-9,9′-bifluoren-4-yl-anthracen-9-yl)-pyrene (DSF-AP) and 1-[2-(9H-carbazol-9-yl)phenyl]-6-[2-(9H-carbazol-9-yl)phenyl-anthracen-9-yl]-pyrene (DCP-AP), were synthesized through boration and the Suzuki aryl-aryl coupling reaction. These two materials exhibited PLmax values at 443?nm and 448?nm in a chloroform solution, and at 458?nm and 463?nm in a thin-film state. EL devices with the synthesized compounds were fabricated in the following configuration: ITO/4,4′,4″-tris(N-(2-naphthyl)-N-phenylamino)triphenylamine (2-TNATA) (60?nm)/N,N′-bis (naphthalene-1-yl)-N,N′-bis(phenyl)benzidine (NPB) (15?nm)/synthesized blue light-emitting materials (35?nm)/Tris-(8-hydroxyquinoline)aluminum (Alq3) (20?nm)/lithium fluoride (LiF) (1?nm)/Al (200?nm). Compared with the device made using an AP core lacking side groups, the device made with DCP-AP displayed 31% higher luminance efficiency (resulting in a value of 4.37?cd/A) and 32% higher power efficiency (to yield 1.93?lm/W), as well as a high external quantum efficiency (3.64%).
- Lee, Suji,Kim, Beomjin,Jung, Hyocheol,Shin, Hwangyu,Lee, Hayoon,Lee, Jaehyun,Park, Jongwook
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p. 255 - 261
(2016/09/07)
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- S-triazine volution arene steric hindrance type bipolar luminescent material and compounding method thereof
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The invention discloses an s-triazine volution arene steric hindrance type bipolar luminescent material and a simple compounding method thereof, and relates to third-generation luminescent display materials and technologies. The specific design structure of the s-triazine volution arene steric hindrance type bipolar luminescent material is shown as below. The material has the advantages of high triplet state energy level, high luminescence efficiency, high thermal decomposition temperature and glass-transition temperature, bipolar transmission characteristic, three-dimensional large-volume steric hindrance effect and simplicity and easiness of the compounding method. The s-triazine volution arene steric hindrance type bipolar luminescent material can be applied to organic electroluminescence devices by taking its initial structure as a main body material. The compound, as the main body material, has wide application prospect and potential commercial value in the field of phosphorescent organic light emitting diodes.
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Paragraph 0039; 0040
(2018/01/11)
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- Effect of increasing electron donor units for high-efficiency blue thermally activated delayed fluorescence
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To enhance the efficiency of organic light-emitting diodes (OLEDs), the application of triplet excitons must be maximized. Two donor–acceptor-type molecules bearing bis-carbazolyl and tris-carbazolyl groups at the ortho position of a phenyl-attached triazine ring were synthesized. These molecules showed very small singlet–triplet energy gaps (ΔEST) of 0.06 and 0.03?eV, respectively, and transient photoluminescence (PL) characteristics, which indicate that they are thermally activated delayed fluorescence (TADF) materials. A high external quantum efficiency (EQE) of 16.5% with deep blue color coordinates of (0.15, 0.22) was observed using a TrisCz–Trz TADF emitter. This interaction between the electron donor and electron acceptor substituents plays a key role in achieving a very small ΔEST and good intramolecular charge transfer (ICT) activities with high photoluminescence (PL).
- Cha, Jae-Ryung,Lee, Chil Won,Gong, Myoung-Seon
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p. 399 - 406
(2017/02/10)
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- Condensed-cyclic compound and organic light-emitting diode comprising the same
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A condensed-cyclic compound is represented by Formula 1, and an organic light-emitting diode includes the condensed-cyclic compound. The organic light-emitting diode includes a first electrode, a second electrode facing the first electrode, and an organic layer. The organic layer includes an emission layer and the condensed-cyclic compound. The condensed-cyclic compound can be included in the emission layer as a host, and the emission layer may further include a dopant.
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Page/Page column 66; 67
(2018/01/20)
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- A novel spiro-annulated host based on carbazole with good thermal stability and high triplet energy for efficient blue and green phosphorescent organic light-emitting diodes
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A novel spiro-annulated host based on carbazole was synthesized and fully characterized. The thermal, photophysical and electrochemical properties of this host material were investigated. The host exhibited good thermal stabilities with a decomposition temperature of 427 °C and also exhibited excellent morphological properties. A high triplet energy (2.90 eV) was obtained for the host due to its spiro-annulated structure. This host was proved to be effective for both blue and green phosphorescent organic light-emitting diodes. Four different blue devices were fabricated with the best performance that a maximum current efficiency of 12.2 cd A-1 and a maximum power efficiency of 8.8 lm W-1. The performance of the host was better than that of 4,4′-bis(9-carbazolyl)-biphenyl which is the benchmark host material in green PHOLED devices.
- Tian, Guojian,Liang, Wenqing,Chen, Yi,Xiang, Ning,Dong, Qingchen,Huang, Jinhai,Su, Jian-Hua
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p. 296 - 302
(2016/01/15)
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- Design of ortho-linkage carbazole-triazine structure for high-efficiency blue thermally activated delayed fluorescent emitters
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Blue thermally activated delayed fluorescent (TADF) emitters were developed by linking a donor moiety to a triazine core via the ortho-position of an aromatic moiety. Three phenylcarbazole derivatives with different substituents were incorporated into the 4,6-diphenyltriazine core to prepare the blue TADF emitters. The photophysical properties and device performance of the blue TADF emitters were investigated, and the blue TADF emitters with 3,6-dimethyl-9-phenylcarbazole as the donor moiety showed a high quantum efficiency of 14.7%.
- Cha, Jae-Ryung,Lee, Chil Won,Lee, Jun Yeob,Gong, Myoung-Seon
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p. 562 - 568
(2016/08/23)
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- Site-Selective N-Arylation of Carbazoles with Halogenated Fluorobenzenes
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A method for the highly site-selective C-N bond-formation reaction of halogenated fluorobenzenes with carbazoles is described. The selectivity of iodine and fluorine atoms on the aromatic ring of fluorinated iodobenzenes was initially determined with a copper-N,N-diisopropylethylamine catalytic system. By changing the position of the iodine atom on the aromatic ring from the 3- or 4-position to the 2-position, the preferred coupling site was switched from the iodine atom to the fluorine atom. Steric hindrance of the fluorinated iodobenzenes is responsible for the selectivity switch. After elucidating the reaction mechanisms of these reaction processes, a metal-free method for the highly site-selective C-N bond-formation reaction of halogenated fluorobenzenes with carbazoles was revealed through C-F bond activation. The metal-free system is able to handle a range of halogenated groups. Thus, a broad range of chlorinated, brominated, and iodinated N-arylated carbazoles were generated, which are widely useful in organic chemistry.
- Wang, Lei,Ji, Enhui,Liu, Ning,Dai, Bin
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p. 737 - 750
(2016/02/27)
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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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Paragraph 0041
(2017/02/28)
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- ORGANIC OPTOELECTRIC DEVICE AND DISPLAY DEVICE
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The present invention relates to an organic optoelectronic element, and a display device comprising the organic optoelectronic element. More particularly, the organic optoelectronic element comprises: an anode and a cathode facing each other; a luminous layer positioned between the anode and the cathode; a hole transfer layer positioned between the anode and the luminous layer; and a hole transfer assistant layer positioned between the hole transfer layer and the luminous layer. The hole transfer layer includes at least one type of a first compound represented by chemical formula 1, and the hole transfer assistant layer includes at least one type of a second compound represented by a combination of chemical formula 2 and chemical formula 3. The chemical formula 1 to chemical formula 3 are the same as defined in the specification.COPYRIGHT KIPO 2016
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Paragraph 0217
(2016/10/24)
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- PHOSPHORUS COMPOUND AND TRANSITION METAL COMPLEX OF THE SAME
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The present invention provides a compound represented by general formula (1) and a transition metal complex containing the compound as a ligand: wherein R1 to R10, N, P, Y, and Z have the meanings as defined in DESCRIPTION.
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Paragraph 0054-0058
(2015/11/10)
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- Organic Light Emitting Material and Organic Light Emitting Diode Having The Same
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The present invention relates to a compound derivative used in an organic light emitting diode and to an organic light emitting diode using the same. More specifically, the present invention provides the organic light emitting diode which manufactures aromatic compounds, increases life of the diode using the aromatic compound as a hole transport material of the organic light emitting diode, and has enhanced luminance and luminous efficiency.(AA) Negative electrode(BB) Electron injection layer(CC) Electron transport layer(DD) Light emitting layer(EE) Hole transport layer(FF) Hole injection layer(GG) Positive electrode(HH) SubstrateCOPYRIGHT KIPO 2015
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Paragraph 0040-0043
(2016/11/28)
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- Organic Light Emitting Material and Organic Light Emitting Diode Having The Same
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The present invention relates to a compound derivative used in an organic light emitting diode and to an organic light emitting diode using the same. More specifically, the present invention provides the organic light emitting diode which manufactures aromatic amine derivative compounds, increases life of the diode using the aromatic amine derivative compound as a hole transporting material of the organic light emitting diode, and has enhanced luminance and luminous efficiency.
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Paragraph 0049-0052
(2020/04/22)
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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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- ORGANIC ELECTROLUMINESCENT MATERIALS AND DEVICES
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Novel host compounds containing indolo[3,2,1-jk]carbazole moiety are disclosed. These compounds are useful in phosphorescent OLEDs and particularly as hosts and/or electron-blocking layer materials.
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Paragraph 0087
(2015/11/16)
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- Copper/β-diketone-catalysed N-arylation of carbazoles
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A copper-catalysed C-N bond-forming reaction of carbazoles with aryl iodides is described. Several commercially available ligands such as β-diketone and diamine, are tested in the N-arylation of carbazoles. The catalytic system generated in situ from an inexpensive copper salt, simple β-diketone and inorganic base efficiently N-arylated the carbazoles. A wide range of aryl iodides and carbazoles can be coupled to generate N-arylcarbazoles in the presence of various functional groups. However, the sterically hindered effect of aryl iodides is evident in this catalytic system. The selectivity of two iodine atoms on the aromatic ring of diiodobenzene is evaluated in the developed catalytic system. Results showed that the selectivity of diiodobenzene can be tuned by the reaction temperature.
- Chen, Fei,Liu, Ning,Ji, Enhui,Dai, Bin
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p. 51512 - 51523
(2015/06/25)
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- Fluorescent compound and Organic light emitting diode device using the same
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A fluorescent compound overcomes problems of increase in the costs and reduction of productivity by complicated structure, and problems of degradation of light emitting efficiency by reduction of hole mobility. Provided in the present invention is a fluorescent compound represented by the chemical formula, and characterized by having each X and Y independently selected an aromatic ring compound, a hetero-ring compound and amine, and having each R1 and R2 be independently hydrogen or be mutually connected to form an aliphatic-confused ring, an aromatic-confused ring, or a hetero-confused ring.COPYRIGHT KIPO 2015
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Paragraph 0069-0072
(2016/12/07)
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- This polycarbazole-phosphine oxide compound and an organic electroluminescence element including (by machine translation)
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The present invention relates to a carbazole-based phosphine oxide compound, and an organic electroluminescent device including the same. According to the present invention, provided are a compound for an organic electroluminescent device which can improve unstable thermal stability and low efficiency characteristics which are the problems of known compounds for an organic electroluminescent device, and particularly, can implement excellent efficiency characteristics in a pure blue phosphorescent device, by using the carbazole-based phosphine oxide compound of the compound for the organic electroluminescent device, and the organic electroluminescent device. According to one aspect of the present invention, the carbazole-based phosphine oxide compound of the compound for the organic electroluminescent device is provided, and the organic electroluminescent device containing the same which can implement thermal stability and high efficiency characteristics is also provided.
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Paragraph 0163
(2016/10/10)
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- Efficient synthesis of π-extended phenazasilines for optical and electronic applications
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The rhodium-catalyzed synthesis of phenazasilines from readily achievable biarylhydrosilanes is presented. This highly efficient method offers opportunities for preparing π-extended phenazasilines with enhanced optoelectronic properties for device applications in organic electronics.
- Li, Huanhuan,Wang, Yang,Yuan, Kai,Tao, Ye,Chen, Runfeng,Zheng, Chao,Zhou, Xinhui,Li, Junfeng,Huang, Wei
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supporting information
p. 15760 - 15763
(2015/01/09)
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- A facile synthesis of indolo[3,2,1-jk]carbazoles via palladium-catalyzed intramolecular cyclization
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A new efficient synthesis of indolo[3,2,1-jk]carbazoles by the palladium-catalyzed cyclization of N-(2-bromoaryl)carbazoles is described. The reaction involves intramolecular C-C bond formation, coupled with the cleavage of a C-X bond and a C-H bond on carbazole ring. Substitutions on N-aryl core with either electron-donating or electron-withdrawing groups are introduced, and different reaction factors for cyclization are evaluated.
- Lv, Jun,Liu, Qiancai,Tang, Jie,Perdih, Franc,Kranjc, Kristof
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p. 5248 - 5252
(2012/10/30)
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- Highly efficient carbazolyl-derived phosphine ligands: Application to sterically hindered biaryl couplings
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A new family of phosphine ligands bearing a bulky carbazolyl scaffold is described. With the combination of ligand 2a and Pd(OAc)2, difficult tri-ortho-substituted biaryl couplings are accomplished smoothly. In particular, the catalyst loading as low as 0.02 mol% of Pd for non-activated 2,6-disubstituted aryl chloride coupling can be achieved.
- Chun To, Sheung,Yee Kwong, Fuk
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supporting information; experimental part
p. 5079 - 5081
(2011/06/10)
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- Structure-property relationship in high triplet energy host materials with a phenylcarbazole core and diphenylphosphine oxide substituent
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A series of high triplet energy host materials with a carbazole core and a diphenylphosphine oxide substituent were synthesized and the effect of the substitution position on the photophysical properties and device performances of the host material was investigated. The substitution position of the diphenylphosphine oxide on the phenyl ring was changed and the substitution at ortho position of the phenyl ring induced the intramolecular charge transfer complex formation. The intramolecular charge transfer complex formation in the ortho substituted compound improved the current density. A maximum quantum efficiency of 20.4% was obtained in the phenylcarbazole host material with the phosphine oxide at para position of the phenyl group and the efficiency was degraded in the ortho substituted host.
- Son, Hyo Suk,Lee, Jun Yeob
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experimental part
p. 1025 - 1032
(2012/03/08)
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- Synthesis of fused phenylcarbazole phosphine oxide based high triplet energy host materials
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High triplet energy host materials based on novel fused phenylcarbazole core structure and diphenylphosphine oxide were synthesized and the physical properties of the host materials were investigated. A high triplet energy of 2.95 eV was obtained from the fused phenylcarbazole based host materials and the energy levels could be manipulated using the diphenylphosphine oxide group. The fused phenylcarbazole based high triplet energy host materials showed excellent morphological stability at high temperature. High triplet energy host materials based on novel fused phenylcarbazole core structure and diphenylphosphine oxide were synthesized and a high triplet energy of 2.95 eV could be obtained from the host materials.
- Jeon, Soon Ok,Lee, Jun Yeob
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experimental part
p. 7295 - 7301
(2010/10/01)
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- COMPOUNDS AND ORGANIC LIGHT EMITTING DIODE USING THE SAME
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Disclosed are new compounds and an organic light emitting diode using the same. The organic light emitting diode using the new compound according to the present invention exhibits excellent characteristics in terms of actuating voltage, light efficiency, and lifespan.
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Page/Page column 115
(2010/04/23)
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- COMPOUNDS AND ORGANIC LIGHT EMITTING DIODE USING THE SAME
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Disclosed are new compounds and an organic light emitting diode using the same. The organic light emitting diode using the new compound according to the present invention exhibits excellent characteristics in terms of actuating voltage, light efficiency, and lifespan.
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Page/Page column 115
(2010/04/23)
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- NEW COMPOUNDS AND ORGANIC LIGHT EMITTING DIODE USING THE SAME
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Disclosed are new compounds and an organic light emitting diode using the same. The organic light emitting diode using the new compound according to the present invention exhibits excellent characteristics in terms of actuating voltage, light efficiency, and lifespan.
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Page/Page column 47
(2008/12/06)
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