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Organic compound and electroluminescent material and applications thereof

An organic compound, selected technology, applied in the field of organic compounds and electroluminescent materials, can solve the problems of phosphorescent host materials that cannot take into account energy consumption, efficiency, processability and life, low luminous efficiency and working life, and high turn-on voltage , to achieve the effect of reducing the injection barrier, improving the luminous performance and stability, and reducing the driving voltage

Active Publication Date: 2021-02-05
WUHAN TIANMA MICRO ELECTRONICS CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, in the current research status of phosphorescent host materials, there are still problems such as high turn-on voltage, high energy consumption, low luminous efficiency and working life. Phosphorescent host materials cannot take into account the comprehensive performance of energy consumption, efficiency, processability and lifetime requirements

Method used

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  • Organic compound and electroluminescent material and applications thereof
  • Organic compound and electroluminescent material and applications thereof
  • Organic compound and electroluminescent material and applications thereof

Examples

Experimental program
Comparison scheme
Effect test

preparation example 1

[0114]

[0115] Under a nitrogen atmosphere, add about 100mL of anhydrous toluene to a 250mL reaction flask, then add reactant A1 (4mmol), reactant 1-1 (4mmol), sodium tert-butoxide t-BuONa (10mmol), palladium catalyst Pd 2 (dba) 3 (0.2 mmol) and the ligand 2-dicyclohexylphosphine-2',6'-dimethoxybiphenyl (S-Phos, 0.6 mmol), the temperature was raised to 110° C., and the reaction was carried out overnight. After the reaction is complete, 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 B1 (yield 83%).

[0116] Characterization results of intermediate B1:

[0117] MALDI-TOF MS (m / z) obtained by matrix-assisted laser desorption ionization time-of-flight mass spectrometry analysis: C 31 h 19 BrO, calculated to be 486.06, found to be 486...

preparation example 2

[0122]

[0123] Under a nitrogen atmosphere, add the reaction solvent 1,2-dichlorobenzene in the reaction flask, add reactant a1 (6mmol), reactant 2-1 (7mmol), potassium carbonate (12mmol), catalyst CuI (0.6mmol) and Ligand 18-crown-6 (0.6mmol), heated to 180°C, reacted for 24h. After the reaction is completed, cool to room temperature, collect the organic phase by suction filtration, 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 b1-1 (yield 71%).

[0124] Characterization results of intermediate b1-1:

[0125] MALDI-TOF MS (m / z) obtained by matrix-assisted laser desorption ionization time-of-flight mass spectrometry analysis: C 23 h 13 N 3 O, the calculated value is 347.11, and the measured value is 347.30.

[0126] The intermediates b1-2, b1-3, b1-4 and b1-5 were prep...

preparation example 3

[0131]

[0132] Under a nitrogen atmosphere, reactant 3-1 (3 mmol) was added to anhydrous tetrahydrofuran THF, stirred at -78°C to cool the reaction solution, and then 1.6M n-butyllithium n-BuLi (3 mmol) was added dropwise, And keep the reaction at -78°C for 2h; slowly drop the reactant A (3mmol) into the low-temperature reaction liquid, after the dropwise addition, continue the reaction at low temperature for 2h, then raise the temperature to room temperature and react overnight. 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;

[0133] 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 rea...

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Abstract

The invention provides an organic compound and an electroluminescent material and applications thereof; the organic compound has a structure represented by a formula I, by designing a spiro parent nucleus structure and introducing a specific substituent, material stacking can be prevented, and the crystallinity of molecules can be reduced; due to the design of the spiro structure and a substituentgroup, the organic compound has a high triplet state energy level T1, and due to a nitrogen heterocyclic ring and a connecting group thereof, the organic compound has relatively good electron transport and hole transport characteristics; HOMO and LUMO energy levels are appropriate, so that energy level matching with adjacent layers is facilitated; the glass transition temperature is high, and themolecular thermal stability is good; the light-emitting efficiency and the service life of the device can be effectively improved. The organic compound can be used as an electroluminescent material for a light-emitting layer, a hole blocking layer or an electron blocking layer of an OLED device, is especially suitable for being used as a phosphorescent host material to be applied in the light-emitting layer, and can significantly improve the light-emitting performance of the device and prolong the service life of the device.

Description

technical field [0001] The invention belongs to the technical field of organic electroluminescent materials, and in particular relates to an organic compound, an electroluminescent material and applications thereof. Background technique [0002] Organic Light Emitting Diode (OLED) is a new generation of display technology developed rapidly in recent years, featuring ultra-thin, self-illuminating, wide viewing angle, fast response, high luminous efficiency, good temperature adaptability, Low driving voltage, low power consumption and flexibility have been widely used in industries such as flat panel display, flexible display, solid-state lighting and automotive display. [0003] In OLED devices, the choice of materials is crucial, and the structure and properties of materials directly affect the final performance of the device. According to the luminescence mechanism, organic electroluminescent materials can be divided into two types: electrofluorescence and electrophosphore...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D471/10C07D471/20C07D471/22C07D491/20C07D491/22C07D495/20C07D495/22C07D519/00C07F7/08C09K11/06H01L51/50H01L51/54H01L27/32H10K99/00
CPCC07D495/20C07D519/00C07F7/0816C07D491/20C07D471/20C07D471/10C07D495/22C07D471/22C07D491/22C09K11/06C09K2211/1011C09K2211/1014C09K2211/1022C09K2211/1029C09K2211/1033C09K2211/1037C09K2211/104C09K2211/1044C09K2211/1048C09K2211/1051C09K2211/1059C09K2211/1074C09K2211/1077C09K2211/1081C09K2211/1088C09K2211/1092H10K85/624H10K85/636H10K85/633H10K85/615H10K85/631H10K85/6576H10K85/6574H10K85/657H10K85/40H10K85/6572H10K50/12C07D493/22C07D471/04C07D493/20H10K50/11H10K85/653H10K85/654H10K85/656H10K50/18
Inventor 冉佺高威张磊代文朋
Owner WUHAN TIANMA MICRO ELECTRONICS CO LTD
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