- Multi-dipolar Chromophores Featuring Phosphine Oxide as Joint Acceptor: A New Strategy toward High-Efficiency Blue Thermally Activated Delayed Fluorescence Dyes
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Blue thermally activated delayed fluorescence (TADF) dyes are basically combinations of strong acceptors and weak donors. In this work, a weak acceptor P=O group was employed to construct a series of weak acceptor-strong donor (WASD)-type emitters with a phenoxazine donor, namely 10-(4-(diphenylphosphoryl)phenyl)-10H-phenoxazine (SPXZPO), 10,10′-(4,4′-(phenylphosphoryl)bis(4,1-phenylene))bis(10H-phenoxazine) (DPXZPO), and 10,10′,10″-(4,4′,4″-phosphoryltris(benzene-4,1-diyl))tris(10H-phenoxazine) (TPXZPO). Owing to the insulating effect of P=O on conjugation extension and intramolecular electronic communications, the photoluminescence spectra of these molecules are almost identical, manifesting the superiority of WASD structure in emission color preservation. Simultaneously, the multi-dipolar characteristics of TPXZPO enhance the intramolecular charge transfer (ICT), facilitating reverse intersystem crossing for higher TADF efficiency and shorter lifetime. As a consequence, TPXZPO realized the desired pure-blue electroluminescence peak at 464 nm, accompanied by a favorable external quantum efficiency (ηext) up to 15.3%, 100% exciton utilization, and reduced efficiency roll-offs. Its complementary full-TADF white organic light-emitting diodes also achieved ηext as high as 16.3%, among the best results reported so far for white TADF devices. The success of TPXZPO, the first example of a P=O-based WASD-type blue TADF dye, is attributed to the comprehensive and harmonized effects of the P=O joint on controlling conjugation and intramolecular electronic communication and the multi-dipolar structure on enhancing ICT.
- Duan, Chunbo,Li, Jing,Han, Chunmiao,Ding, Dongxue,Yang, He,Wei, Ying,Xu, Hui
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Read Online
- Molecular Design of Thermally Activated Delayed-Fluorescent Emitters Using 2,2′-Bipyrimidine as the Acceptor in Donor–Acceptor Structures
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Donor–acceptor–donor (D–A–D)-type thermally activated delayed fluorescence (TADF) emitters 5,5′-bis{4-[9,9-dimethylacridin-10(9H)-yl]phenyl}-2,2′-bipyrimidine (Ac-bpm) and 5,5′-bis[4-(10H-phenoxazin-10-yl)phenyl]-2,2′-bipyrimidine (Px-bpm), based on the 2,2′-bipyrimidine accepting unit, were developed and their TADF devices were fabricated. The orthogonal geometry between the donor unit and the 2,2′-bipyrimidine accepting core facilitated a HOMO/LUMO spatial separation, thus realizing thermally activated delayed fluorescence. The exhibited electroluminescence ranged from green to yellow, depending on the donor unit, with maximum external quantum efficiencies of up to 17.1 %.
- Park, Hee-Jun,Han, Si Hyun,Lee, Jun Yeob
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Read Online
- Thermal activation delayed fluorescence material based on dibenzothiophene sulfone
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The chemical formula of the thermal activation delayed fluorescent material based on dibenzothiophene sulfone is as shown in the specification. In the above formula, the substituent R is substituted. 1 A hydrogen atom is used. The invention relates to an electron donor carbazole and derivatives thereof, a phenoxazine and derivatives thereof or acridine and derivatives thereof. Substituent R2 For the hydrogen atom, the electron donor carbazole and its derivatives, phenazine and its derivatives or acridine and derivatives thereof. The substituents R1, R2 may be the same or different. The electron donor is introduced to 4 and 6 positions of the dibenzothiophene sulfone group by using a chemical single bond, and the molecular configuration of the luminescent material can be optimized. The luminescent color of the luminescent material can be adjusted by changing the type and the quantity of the electron donor. By comprehensively utilizing the two means, the luminous efficiency of the luminescent material can be enhanced, so that the obtained luminescent material has thermal retardation and fluorescence characteristics, and the luminous quantum efficiency of the luminescent material is obviously improved to 95%.
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Paragraph 0025-0028
(2021/09/26)
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- ORGANIC ELECTROLUMINESCENCE DEVICE AND ORGANIC COMPOUND FOR ORGANIC ELECTROLUMINESCENCE DEVICE
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The organic electroluminescent device according to an embodiment 1 is an n-type electrode. The EML includes 2 electrodes and an emitting layer disposed between the (1 and 2) th electrodes, and the EML includes the compound represented by Formula 1, and the EML may exhibit high emission efficiency characteristics and improved lifetime characteristics. Chemical Formula 1. Wherein each substituent in Formula 1 is as defined in the description of the invention.
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Paragraph 0157-0159
(2021/07/27)
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- Compound for organic luminescence and application thereof
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The invention relates to a compound for organic luminescence. The structure of the compound is shown as a formula (I) in the description, wherein X is selected from one of carbonyl, oxygen atom or sulfur atom; and the formula (I) is also connected with a
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Paragraph 0029-0033
(2021/03/13)
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- Small-molecule luminescent materials based on 1,3-benzodiazine (quinazoline) and production method and application of small-molecule luminescent materials based on 1,3-benzodiazine (quinazoline)
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The invention provides small-molecule luminescent materials based on 1,3-benzodiazine (quinazoline) and a production method and application of the small-molecule luminescent materials based on the 1,3-benzodiazine (quinazoline), and belongs to the technical field of organic photoelectric materials. A structural formula of the luminescent materials is shown in a formula (1)as shown in the description, in theformula (1), each of R1, R2, R3, R4, R5 and R6 is selected from one of a hydrogen atom, an alkoxy group, an alkylthio group, an alkylamine group, an arylamine group, an aryloxy group, an arylthio group, an aryl group and an aromatic heterocyclic group, and at least one of R1, R2, R3, R4, R5 and R6 is an aromatic heterocyclic group. According to the small-molecule luminescent materials based on the 1,3-benzodiazine (quinazoline) and the production method and application of the small-molecule luminescent materials based on the 1,3-benzodiazine (quinazoline), the 1,3-benzodiazine (quinazoline) is introduced into TADF materials for the first time, and high luminescence efficiency is achieved. The materials are simple to synthesize, steps are short, and synthesis cycles are short. Reaction yields are high, and the yields of all the steps are higher than 70%, so that the cost is saved. The OLED luminescent efficiency is high, and the highest efficiency can exceed 20%.
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Paragraph 0050-0054
(2020/02/14)
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- Heterocyclic compound and organic light emitting device including the same
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Provided are a heterocyclic compound and an organic light-emitting device including the same. The heterocyclic compound may be represented by Formula 1: in the Formula 1, A1, X2, Y1, Y2, m1, m2, R10,R20, R30, b10, b20 and b30 are same as described in the description.
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Paragraph 060-0610
(2020/07/15)
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- Organic light-emitting material containing benzo[c][1,2,5]thiadiazole derivative receptor structural unit and application
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The invention provides an organic light-emitting material based on a donor-receptor structure of a benzo[c][1,2,5]thiadiazole-4-aldehyde group receptor and a 2-(benzo[c][1,2,5]thiadiazole-4-methylene)malononitrile receptor and application thereof. The organic light-emitting material is a receptor-donor separation system, wherein the receptor is benzo[c][1,2,5]thiadiazole-4-aldehyde or 2-(benzo[c][1,2,5]thiadiazole-4-methylene) malononitrile, and a donor is carbazole and a derivative or benzoxazine and the like. The lowest unoccupied molecular orbital (LUMO) in the material is located in the receptor, and the highest occupied molecular orbital (HOMO) in the material is located in the donor, so that the molecular orbital energy level of the luminescent material can be effectively regulated and controlled through electrical regulation of the receptor structure and the donor. By regulating and controlling the structure of the light-emitting material or the electron donating capability of the donor, the light-emitting color of material molecules can be conveniently regulated. The organic light-emitting material has the characteristic that the light-emitting color is easy to adjust, andcan be used as a light-emitting material for preparing an OLED device.
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Paragraph 0072-0074
(2020/08/09)
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- Thermally activated delayed fluorescence material for locking triphenylphosphine oxide receptor based on ether bond conformation
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The invention discloses a thermally activated delayed fluorescence material for locking a triphenylphosphine oxide receptor based on ether bond conformation. The material has a structure as shown in aformula which is described in the specification. The thermally activated delayed fluorescence material has very good blue light or green light color purity, very high luminous quantum efficiency andcharge injection/transmission performance, and is applicable as a luminescent material for preparation of a high-performance organic electroluminescent device; in addition, the blue light-emitting material also has a very high excited state energy level, and can be used as a host material for preparing a high-performance organic light-emitting device.
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Paragraph 0029; 0036-0037; 0040-0041
(2020/03/05)
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- The role of distance between donor and acceptor in configuration stability of Z/E isomers based on cyanostilbene
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Cyanostilbene has been widely used in the design of photoelectrical materials, and our previous work has confirmed its Z/E isomerization reaction under photoirradiation can be suppressed by forming a suitable donor-acceptor (D-A) structure. In this work, we report two D-A cyanostilbene derivatives with AIE activity, abbreviated as PZPNC and PZNC, whose chemical structures only differ by one more phenyl between donor and acceptor. Their Z/E isomers were characterized with single crystal structures and the impact of D-A distance on their stability of Z/E configuration was studied. The in-situ UV–vis spectra and HPLC results of Z/E-PZPNC and Z/E-PZNC under photoirradiation demonstrated that the Z/E isomerization reaction of PZNC was slower than PZPNC, indicating that the shorter D-A distance is conductive to the stability of cyanostilbene due to the relatively stronger charge transfer state with lower energy.
- Xu, Chendong,Dong, Yujie,Li, Weijun,Zhao, Ruiyang,Dai, Yuyu,Zhang, Cheng,Song, Qingbao
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- LIGHT-EMITTING MATERIAL, ORGANIC LIGHT-EMITTING DEVICE, AND COMPOUND
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A compound represented by the general formula (11) is useful as a light-emitting material. R1, R2, R4 and R5 represent a group represented by the general formula (2), R11 to R20 represent a hydrogen atom or a substituent, and L12 represents a substituted or unsubstituted arylene group or a substituted or unsubstituted heteroarylene group.
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Paragraph 0222-0224
(2019/11/22)
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- Universal bipolar host material containing pyridine group, as well as preparation and application thereof in organic light emitting diodes
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The invention belongs to the technical field of organic photoelectric materials, and discloses a universal bipolar host material containing a pyridine group, as well as preparation and application thereof in organic light emitting diodes. The universal bipolar host material containing a pyridine group has a structure as shown in the specification, wherein n is an integer of 1-10, R1 is a hydrogenatom or alkyl chain, and Ar is an aromatic nucleus derivative electron-donating group. The invention further discloses a method for preparing the host material. The host material has excellent electron transmission performance and hole transporting performance since triplet energy is increased, can be used for preparing blue-light, green-light and red-light PHOLEDs with excellent performance, suchas high efficiency, low efficiency roll-off and the like. High-performance white-light PHOLEDs of single host is expected to achieve by utilizing the host material. The host material can be applied to the field of organic photoelectric devices.
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Paragraph 0091; 0095; 0096; 0097
(2019/04/27)
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- Asymmetric thermally activated delayed fluorescence (TADF) emitters with 5,9-dioxa-13: B -boranaphtho[3,2,1- de] anthracene (OBA) as the acceptor and highly efficient blue-emitting OLEDs
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A series of new organic emitters was prepared by introducing various donors (Ds) to the meta-position of the boron atom in the central phenyl ring in the acceptor (A) of 5,9-dioxa-13b-boranaphtho[3,2,1-de]anthracene (OBA). Moreover, their thermal, photophysical, electrochemical and electroluminescent (EL) properties were characterized in detail. The photophysical results revealed that these OBA-based molecules adopted a D-A configuration and exhibited efficient thermally activated delayed fluorescence (TADF) properties with a reverse inter-system crossing constant (kRISC) in the order of 105 s-1. It has been shown that introducing the -Br group to the OBA acceptor could increase kRISC by 2 to 3 times. Importantly, the deep-blue TADF emitter OBA-O showed a high photoluminescent quantum yield (PLQY) of 0.84, while its blue analog OBA-BrO with the -Br group exhibited an even higher PLQY of 0.92 in the doped film state. Benefitting from their high PLQYs as blue-emitting TADF emitters, the doped organic light-emitting diodes (OLEDs) based on these OBA-based TADF emitters exhibited attractive electroluminescent (EL) performances. The blue-emitting OLEDs with CIE (0.17, 0.17) showed the maximum external quantum efficiency (ηext) of 17.8%, current efficiency (ηL) of 33.2 cd A-1 and power efficiency (ηP) of 34.2 lm W-1, while that for the bluish-green device were 22.5%, 49.2 cd A-1 and 56.9 lm W-1, respectively. Thus, the great potential of these TADF emitter-based OBA acceptors was clearly demonstrated by their EL data. In addition, these asymmetric OBA-based molecules will enrich the structural diversity of this type of TADF emitter.
- Song, Dongdong,Yu, Yue,Yue, Ling,Zhong, Daokun,Zhang, Yindi,Yang, Xiaolong,Sun, Yuanhui,Zhou, Guijiang,Wu, Zhaoxin
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supporting information
p. 11953 - 11963
(2019/10/16)
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- Cyanodiphenylethylene compound with stable Z/E configuration in excited state and preparation method and application thereof
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The invention provides cyanodiphenylethylene compound with stable Z/E configuration in excited state and a preparation method and application thereof. The cyanodiphenylethylene compound with stable Z/E configuration in excited state acts as a novel light-emitting isomer; the structure can be controlled by introducing different push-pull electron groups so as to adjust light emission color and efficiency of the isomer; therefore, the cyanodiphenylethylene compound has a very promising application prospect in the fields, such as photoluminescence, piezochromism and fluorescent sensing.
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Paragraph 0066-0068
(2019/01/23)
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- Thermal activation delay materials and organic electro-optical device comprising thermal activation delay materials
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The invention relates to thermal activation delay materials and an organic electro-optical device comprising the thermal activation delay materials. The thermal activation delay materials are chemicalcompounds having a structure as shown in the formula (I). The organic electro-optical device comprises an anode, a cathode and an organic thin film layer located between the anode and the cathode, wherein the organic thin film layer comprises a light-emitting layer, and any kind of or the combination of at least two kinds of a hole transporting layer, a hole injecting layer, an electron resistinglayer, a hole resisting layer, an electron transporting layer and an electron injecting layer; the light-emitting layer comprises any kind of or the combination of at least two kinds of the thermal activation delay materials; and the chemical compounds are used as any kind of doped materials, co-doped materials or main body materials. Delta Est of the thermal activation delay materials provided by the invention is smaller than or equal to 0.30eV, and even the delta Est is smaller than or equal to 0.15eV, so that the light-emitting efficiency of the organic electro-optical device is improved.
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Paragraph 0086; 0087
(2019/01/23)
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- Organic micromolecule material based on 2,6-dimethyl-4-cyanophenyl receptor unit, preparation and application
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The invention belongs to the technical field of organic photoelectric materials, and discloses an organic micromolecule material based on a 2,6-dimethyl-4-cyanophenyl receptor unit, preparation and application. The organic micromolecule material has a structural formula as shown in formula (I), and Ar in the formula shows a phenyl aromatic amine heterocycle or phenyl aromatic amine donor unit. Thematerial has a weak intramolecular charge transfer state, and thus, fluorescence emission of a zone from dark blue to ultraviolet can be realized. Meanwhile, because the molecules have quite short effective conjugated length, the material has high triplet state energy level. In the application of an organic electroluminescent device, the problem of unbalanced charge carriers of a unipolar organicphotoelectric material can be solved effectively, therefore, the structure of the device is simplified, and the performance of the device is improved.
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Paragraph 0082; 0084; 0085
(2018/10/19)
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- D-pi-A type organic fluorescent material on basis of naphthalene and method for preparing D-pi-A type organic fluorescent material
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The invention relates to a D-pi-A type organic fluorescent material on the basis of naphthalene and a method for preparing the D-pi-A type organic fluorescent material. A structural formula of the D-pi-A type organic fluorescent material is shown as a formula (I), the D in the formula (I) represents electron donor units, and the A in the formula (I) represents electron acceptor units. The method includes main preparation steps of carrying out reaction on electron donor compounds and electron acceptor compounds at the room temperature in inert gas atmosphere in the presence of catalysts and solvents for 20-30 minutes; dropwise adding potassium carbonate solution into reaction products and carrying out reaction at the temperature of 75-90 DEG C for 8-24 hours; separating and purifying products to obtain the D-pi-A type organic fluorescent material on the basis of the naphthalene. A molar ratio of the electron donor compounds to the electron acceptor compounds is 1:(1-3). The D-pi-A typeorganic fluorescent material and the method have the advantages that the naphthalene is used as a pi conjugate platform, the electron donor units (D) and the electron acceptor units (A) are led onto 1, 8 locations, and accordingly the D-pi-A type organic fluorescent material can be constructed without precious metal and is low in synthesis cost, good in heat stability and high in luminous and quantum efficiency.
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Paragraph 0122; 0126; 0127
(2018/07/15)
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- COMPOUND, LIGHT EMITTER COMPOUND, LIGHT EMITTER, LIGHT-EMITTING DEVICE, LIGHT SOURCE, AUTHENTICATION DEVICE, AND ELECTRONIC APPARATUS
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PROBLEM TO BE SOLVED: To provide: a compound and a light emitter compound that are capable of providing an efficient, long-life light emitter emitting light in a wide wavelength region of the near-infrared region by being included in a light-emitting layer included in a light emitter; an efficient, long-life light emitter emitting light in a wide wavelength region of the near-infrared region; and a light-emitting device, a light source, an authentication device and an electronic apparatus that comprise the light emitter. SOLUTION: A light emitter 1 comprises a positive electrode 3, a negative electrode 8, and a light-emitting layer 5 disposed between the positive electrode 3 and the negative electrode 8 to emit light upon energization between the positive electrode 3 and the negative electrode 8. The light-emitting layer 5 contains a compound represented by a general formula IRD as a light-emitting material. SELECTED DRAWING: Figure 1 COPYRIGHT: (C)2018,JPOandINPIT
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Paragraph 0194; 0199; 0201-0202
(2018/08/30)
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- The azatryptophan-based fluorescent platform for in vitro rapid screening of inhibitors disrupting IKKβ-NEMO interaction
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The nuclear factor-κB (NF-κB) plays an important role in inflammatory and immune responses. Aberrant NF-κB signaling is implicated in multiple disorders, including cancer. Targeting the regulatory scaffold subunit IκB kinase γ (IKKγ/NEMO) as therapeutic interventions could be promising due to its specific involvement in canonical NF-κB activation without interfering with non-canonical signaling. In this study, the use of unnatural amino acid substituted IKKβ with unique photophysical activity to sense water environment changes upon interaction with NEMO provides a powerful in vitro screening platform that would greatly facilitate the identification of compounds having the potential to disrupt IKKβ-NEMO interaction, and thus specifically modulate the canonical NF-κB pathway. We then utilized a competitive binding platform to screen the binding ability of a number of potential molecules being synthesized. Our results suggest that a lead compound (?)-PDC-099 is a potent agent with ascertained potency to disrupt IKKβ-NEMO complex for modulating NF-κB canonical pathway.
- Chao, Wei-Chih,Chiang, Tzu-Hsuan,Chaudhari, Prakash D.,Lin, Li-Ju,Lu, Jyh-Feng,Hong, Bor-Cherng,Wang, Jinn-Shyan,Lin, Ta-Chun,Shen, Jiun-Yi,Chou, Pi-Tai
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supporting information
p. 504 - 511
(2018/09/29)
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- Organic compound with dibiphenyl five-membered heterocyclic ring as skeleton and application of same to OLEDs
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The invention relates to an organic compound with a dibiphenyl five-membered heterocyclic ring as a skeleton and application of the same to OLEDs. The compound uses the dibiphenyl five-membered heterocyclic ring as the skeleton and an aromatic structure derived from a phenyl group, a dibiphenyl group or a naphthyl group as a branched chain. The compound provided by the invention has high glass transition temperature and molecular heat stability, appropriate HOMO and LUMO energy levels and high Eg. Through optimization of the structures of OLED devices, the photoelectric properties and service life of the OLED devices can be effectively improved.
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Paragraph 0058; 0060
(2017/10/13)
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- Organic light-emitting diode materials
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Described herein are molecules for use in organic light emitting diodes. Example molecules comprise at least one acceptor moiety A, at least one donor moiety D, and optionally one or more bridge moieties B. Each moiety A is covalently attached to either the moiety B or the moiety D, each moiety D is covalently attached to either the moiety B or the moiety A, and each moiety B is covalently attached to at least one moiety A and at least one moiety D. Values and preferred values of moieties A, D, and B are defined herein.
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Paragraph 0360; 0361; 0365; 0377
(2017/07/26)
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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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Paragraph 0013
(2017/02/09)
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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 0022
(2017/04/26)
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- Full-Color Delayed Fluorescence Materials Based on Wedge-Shaped Phthalonitriles and Dicyanopyrazines: Systematic Design, Tunable Photophysical Properties, and OLED Performance
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Purely organic light-emitting materials, which can harvest both singlet and triplet excited states to offer high electron-to-photon conversion efficiencies, are essential for the realization of high-performance organic light-emitting diodes (OLEDs) without using precious metal elements. Donor-acceptor architectures with an intramolecular charge-transfer excited state have been proved to be a promising system for achieving these requirements through a mechanism of thermally activated delayed fluorescence (TADF). Here, luminescent wedge-shaped molecules, which comprise a central phthalonitrile or 2,3-dicyanopyrazine acceptor core coupled with various donor units, are reported as TADF emitters. This set of materials allows systematic fine-tuning of the band gap and exhibits TADF emissions that cover the entire visible range from blue to red. Full-color TADF-OLEDs with high maximum external electroluminescence quantum efficiencies of up to 18.9% have been demonstrated by using these phthalonitrile and 2,3-dicyanopyrazine-based TADF emitters.
- Park, In Seob,Lee, Sae Youn,Adachi, Chihaya,Yasuda, Takuma
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p. 1813 - 1821
(2016/03/30)
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- Dimesitylarylborane-based luminescent emitters exhibiting highly-efficient thermally activated delayed fluorescence for organic light-emitting diodes
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Triarylboranes are widely used as luminescent molecules. However, there are few reports focused on thermally activated delayed fluorescence (TADF) characteristics. In this study, new donor-acceptor triarylboranes exhibiting TADF characteristics are designed, synthesized, and applied to organic light-emitting diodes (OLEDs) as an emitter. Electro-accepting dimesitylphenylborane connected with carbazole (7), 9,9-dimethylacridane (8), and phenoxazine (9) as electron-donating units are synthesized in only two steps with good yield. Compounds 8 and 9 exhibit light blue and green TADF with good PL quantum yields of 89 and 87% in toluene, respectively. On the other hand, compound 7 shows normal deep blue fluorescence without TADF characteristics. Density functional theory and time-dependent density functional theory studies reveal that high electron-donating ability of donor unit and large dihedral angles between cross-linking phenylene and donor units are attributed to spatially separate the HOMO and LUMO, which results in lowering the energy gap between lowest singlet (S1) and triplet (T1) excited states and accelerating reverse intersystem crossing of excitons from T1 to S1 states. OLEDs using compounds 8 and 9 as emitters exhibit light blue and green emission with very good external quantum efficiencies of 16.0 and 17.3%, respectively.
- Kitamoto, Yuichi,Namikawa, Taketo,Suzuki, Takatsugu,Miyata, Yasuo,Kita, Hiroshi,Sato, Tetsuo,Oi, Shuichi
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p. 208 - 217
(2016/05/11)
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- Triphenyl phosphorus oxide-based thermal excitation delayed fluorescent blue light guest material and its preparation method and use
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The invention relates to a fluorescent blue light guest material and its preparation method and use and especially relates to a triphenyl phosphorus oxide-based thermal excitation delayed fluorescent blue light guest material and its preparation method and use. The triphenyl phosphorus oxide-based thermal excitation delayed fluorescent blue light guest material solves the problem that because of large difference of an electron donor and an acceptor, when the electron donor is increased, guest emission wavelength produces red shift so that stable and efficient blue guest luminescence cannot be realized. The blue light guest material has a structural formula shown in the description. The preparation method comprises 1, preparing PXZPhBr, PXZPhBr, PTZPhBr and DMACPhBr, 2, mixing the products obtained through the step 1 and tetrahydrofuran, adding n-butyllithium and diphenylphosphinous chloride into the mixture, adding hydrogen peroxide into the mixture, carrying out stirring and carrying out chromatography and recrystallization. The triphenyl phosphorus oxide-based thermal excitation delayed fluorescent blue light guest material is used for preparation of a thermal excitation delayed fluorescent electroluminescent device. The material utilizes short-axis modification strategy, effectively keeps a matrix triplet state energy level, has a donor-acceptor (D-A)-type molecular structure and balances carrier injection and transmission. The preparation method belongs to the field of fluorescent material preparation.
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Paragraph 0074; 0075
(2016/10/31)
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- Light blue and green thermally activated delayed fluorescence from 10H-phenoxaborin-derivatives and their application to organic light-emitting diodes
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New luminescent compounds consisting of 10H-phenoxaboryl groups as electron-accepting units and carbazole (9), 9,9-dimethylacridane (10), or phenoxazine (11) as an electron-donating unit have been synthesized. Compounds 10 and 11 showed thermally activated delayed fluorescence (TADF) with light blue and green emissions, respectively, with very high PL quantum yields (PLQYs), however, compound 9 exhibited only a prompt emission and no delayed component. Photoluminescence studies and quantum chemical calculation based on density functional theory (DFT) and time-dependent density functional theory (TD-DFT) revealed that in comparison with compound 9, the HOMO and LUMO for compounds 10 and 11 are well separated, resulting in lowering of ΔEST and effective reverse intersystem crossing (RISC) between a lowest triplet excited state (T1) and a lowest singlet excited state (S1). Organic light-emitting diodes (OLEDs) using compounds 10 and 11 exhibited light blue and green emissions with very good maximum ηext of 15.1% and 22.1%, respectively.
- Kitamoto, Yuichi,Namikawa, Taketo,Ikemizu, Dai,Miyata, Yasuo,Suzuki, Takatsugu,Kita, Hiroshi,Sato, Tetsuo,Oi, Shuichi
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p. 9122 - 9130
(2015/09/07)
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- A general route for synthesis of N-aryl phenoxazines via copper(i)-catalyzed N-, N-, and O-arylations of 2-aminophenols
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A novel copper(i)-catalyzed tandem reaction of N- and O-arylations of 2-[N-(2-chlorophenyl)amino]phenols was developed, by which a series of structurally novel N-aryl phenoxazines were synthesized efficiently. This success owes much to the discovery of hi
- Liu, Nan,Wang, Bo,Chen, Wenwen,Liu, Chulong,Wang, Xinyan,Hu, Yuefei
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p. 51133 - 51139
(2014/12/10)
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- A comparative study on properties of two phenoxazine-based dyes for dye-sensitized solar cells
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Two phenoxazine (POZ)-based organic D-π-A sensitizers (POZ-1 and POZ-2) were synthesized. Then these two dyes were applied in dye-sensitized solar cells (DSSCs) to investigate the influence of different conjugated direction, extra phenyl ring and alkyl chain on the light-harvesting, energy level and photovoltaic properties through a joint spectral, electrochemical and photovoltaic study. The result shows that dye POZ-2 exhibits higher power conversion efficiency (η = 6.5%) than dye POZ-1 (η = 2.4%) under standard illumination (Global Air Mass 1.5). Besides, the geometries of the dyes were optimized to gain insight into the molecular structure and electron distribution. The charge extraction and transient photovoltage decay measurements were further performed to understand the alterative order of efficiency.
- Tan, Haijun,Pan, Chunyue,Wang, Gang,Wu, Yingying,Zhang, Yiping,Yu, Guipeng,Zhang, Min
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- Bromination of 10-Phenylphenothiazine and 10-Phenylphenoxazine
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The reaction of either 10-phenylphenothiazine (1) with bromine in acetic acid or the cation radical of 1 with bromide ion gives ring substitution only and in accord with customary stoichiometry for nucleophilic substitution of aromatic cation radicals.However, the reaction of 1 with pyridinium bromide perbromide (2) gives predominantly 10-phenyl ring substitution and a small amount of ring substitution products.Evidence is presented which indicates that ring substitution occurs via cation radical whereas 10-phenyl substitution proceeds via electrophilic attack on the neutral molecule 1.Substitution of 10-phenylphenoxazine (4) occurs predominantly but not exclusively on the phenoxazine ring; some bromination does occur on the 10-phenyl ring.In contrast, the reaction of 4 with bromine gives only ring mono- and disubstitution products.These results indicate that both 1 and 4 react similarly under the same conditions.
- Jovanovic, Misa V.,Biehl, Edward R.
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p. 1905 - 1908
(2007/10/02)
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