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Organic compound, organic electroluminescent material and application thereof

An organic compound and selected technology, applied in the field of organic compounds and organic electroluminescent materials, can solve the problems of high glass transition temperature, small concentration quenching effect, large intermolecular attraction, etc., to avoid crystallization and reduce work. Voltage and energy consumption, the effect of extending operating life

Active Publication Date: 2021-06-22
WUHAN TIANMA MICRO ELECTRONICS CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

CN107311978A discloses a phosphorescent host material, its preparation method and an organic light-emitting device using the material. The molecule of the phosphorescent host material contains a fluorene structural unit, and the fluorene structural unit is connected with a carbazolyl group and a pyridyl group. Band gap, and the glass transition temperature is higher, the concentration quenching effect is small
However, the current phosphorescent host materials have a planar molecular structure, and the intermolecular attraction is large, which is not conducive to evaporation; and the phosphorescent host materials generally have defects such as high turn-on voltage, low luminous efficiency, and short working life, which cannot be achieved in terms of energy consumption and efficiency. , processability and stability

Method used

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  • Organic compound, organic electroluminescent material and application thereof
  • Organic compound, organic electroluminescent material and application thereof
  • Organic compound, organic electroluminescent material and application thereof

Examples

Experimental program
Comparison scheme
Effect test

preparation example 1

[0108]

[0109] Under a nitrogen atmosphere, add about 20mL of anhydrous dimethyl sulfoxide (DMSO) to the reaction flask, then add reactant a1 (5mmol), reactant 1 (5.25mmol), and cesium carbonate (15mmol) in sequence, and heat up to 120 After reacting at ℃ for 2 hours, continue to raise the temperature to 180℃ for 4 hours. Cool to room temperature, add dichloromethane (DCM) / H 2 O was extracted, and the collected organic phase was washed with anhydrous Na 2 SO 4 After drying, the filtrate was collected by suction filtration, the solvent was spun off and purified by column chromatography to obtain intermediate A-1 (yield 72%).

[0110]Characterization results of intermediate A-1: ​​MALDI-TOF MS (m / z) obtained by matrix-assisted laser desorption ionization time-of-flight mass spectrometry: C 13 h 7 BrN 2 O, calculated: 285.97, found: 286.17.

[0111] Intermediates B-1 and C-1 were prepared according to the above synthetic route, and the raw materials, products and test r...

preparation example 2

[0115]

[0116] Under nitrogen atmosphere, add 100mL solvent (toluene:ethanol:water=7:2:1) in reaction bottle, then add reactant A-1 (4mmol), reactant 2 (4.5mmol), potassium carbonate (10mmol) successively and palladium catalyst Pd(PPh 3 ) 4 (0.2 mmol), heated to 90°C, and reacted overnight. Cool to room temperature, add DCM / H 2 O was extracted, and the collected organic phase was washed with anhydrous Na 2 SO 4 After drying, the filtrate was collected by suction filtration, the solvent was spun off and purified by column chromatography to obtain intermediate A-2 (yield 76%).

[0117] Characterization results of intermediate A-2: MALDI-TOF MS (m / z): C 19 h 11 ClN 2 O, Calculated: 318.06, Found: 318.27.

[0118] Intermediates B-2 and C-2 were prepared according to the above synthetic route, and the raw materials, products and test results are shown in Table 2.

[0119] Table 2

[0120]

preparation example 3

[0122]

[0123] Under nitrogen atmosphere, intermediate A-2 (3mmol) was added to anhydrous tetrahydrofuran (THF), stirred at -78°C to cool the reaction solution, and then 1.6M n-butyl lithium (n-BuLi, 3mmol) was added dropwise Add and keep reacting at -78°C for 2h; Slowly add reaction intermediate 3-1 (3mmol) into the low-temperature reaction solution dropwise. After the reaction is completed, add a small amount of water to quench, add DCM / H 2 O was extracted, the organic phase was collected and washed with anhydrous Na 2 SO 4 Dry, collect the filtrate by suction filtration, and spin off the solvent to obtain the crude product;

[0124] The above crude product was added to 20 mL of acetic acid under nitrogen, stirred and heated, and reacted at 120° C. for 2 h, then added 2 mL of hydrochloric acid, and heated at this temperature for 12 h. After the reaction was completed, it was cooled and extracted, and the organic phase was collected and the solvent was spun off, and pu...

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Abstract

The invention provides an organic compound, an organic electroluminescent material and application thereof, the organic compound has a structure as shown in a formula I, has a high triplet state energy level and a suitable HOMO / LUMO energy level through mutual cooperation of a skeleton structure and substituent groups, and can effectively improve equilibrium migration of current carriers and expand an exciton recombination region; meanwhile, the skeleton structure containing the spiro ring can prevent material stacking and crystallization, so that the organic compound has higher glass transition temperature and molecular thermal stability, and the luminous efficiency and the service life of the device are further improved. The organic compound serving as an electroluminescent material can be applied to a luminescent layer, an electron blocking layer or an optical auxiliary layer of an OLED device, the luminous efficiency of the device can be remarkably improved, the working voltage and energy consumption of the device are reduced, and the service life of the device is prolonged.

Description

technical field [0001] The invention belongs to the technical field of organic electroluminescent materials, and in particular relates to an organic compound, an organic electroluminescent material and applications thereof. Background technique [0002] Organic electroluminescence (EL) technology is the most promising next-generation display technology. Compared with inorganic EL devices, organic EL devices (Organic Light Emitting Diode, OLED) have ultra-thin, self-luminous, With the advantages of wide viewing angle, fast response, high luminous efficiency, good temperature adaptability, easy bending, simple production process, low driving voltage, low energy consumption, and full luminous color, it is widely used in flat panel display, flexible display, solid-state lighting and vehicle display industries. be widely used. [0003] In OLED devices, the structure and properties of organic materials directly affect the light-emitting performance of the device, so the choice of...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D487/20C07D498/10C07D498/22C07D513/10C07D519/00C09K11/06H01L51/54H01L51/50
CPCC07D513/10C07D519/00C07D498/22C07D487/20C07D498/10C09K11/06C09K2211/1077C09K2211/1033C09K2211/1029C09K2211/1088C09K2211/1092C09K2211/1044C09K2211/1048C09K2211/1074C09K2211/1081C09K2211/1037C09K2211/1059H10K85/615H10K85/636H10K85/657H10K85/6574H10K85/6576H10K85/6572H10K50/18H10K50/11
Inventor 冉佺高威张磊代文朋翟露
Owner WUHAN TIANMA MICRO ELECTRONICS CO LTD
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