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Condensed ring compound containing boron atoms and nitrogen atoms and application thereof

A technology of nitrogen atoms and boron atoms, which is applied in the field of organic electroluminescence, can solve the problems of low luminous efficiency, fast efficiency roll-off, and high cost of luminescent materials, and achieve improved luminous efficiency and life, low manufacturing cost, and low roll-off Effect

Pending Publication Date: 2022-03-11
GUANGZHOU CHINARAY OPTOELECTRONICS MATERIALS
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0005] In view of the above deficiencies in the prior art, the object of the present invention is to provide a fused ring compound containing boron atoms and nitrogen atoms and its application, aiming to solve the problem of high cost of existing phosphorescent materials, rapid efficiency roll-off under high luminance, The problem of short life, and solve the problem of low luminous efficiency and short life of luminescent materials

Method used

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  • Condensed ring compound containing boron atoms and nitrogen atoms and application thereof
  • Condensed ring compound containing boron atoms and nitrogen atoms and application thereof
  • Condensed ring compound containing boron atoms and nitrogen atoms and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0130] The synthetic route of compound (1) is as follows:

[0131]

[0132] Synthesis of Intermediates 1-3:

[0133] Under nitrogen protection atmosphere, in a dry three-necked flask, add 10mmol intermediate 1-1 and 10mmol intermediate 1-2, 0.2mmol palladium acetate, 30mmol potassium carbonate, 0.2mmol tri-tert-butylphosphine, and add 150ml toluene to make It was dissolved, heated to 80°C until the reaction solution was refluxed, and reacted for 12 hours. After the reaction was complete, water was added to extract the reaction, and the organic phase was extracted with dichloromethane at the same time. The organic phase was combined and washed several times, dried with anhydrous magnesium sulfate, and filtered. The solvent was evaporated to dryness to obtain a crude product, which was purified by flash column chromatography to obtain 3.62 mmol of intermediate 1-3 with a yield of 36.2%. MS (ASAP) = 562.1.

[0134] Synthesis of compound (1):

[0135] In a 250ml three-necked...

Embodiment 2

[0137] The synthetic route of compound (2) is as follows:

[0138]

[0139] Synthesis of Intermediate 2-3:

[0140] Under a nitrogen atmosphere, in a dry three-necked flask, add 10mmol of intermediate 2-1 and 10mmol of intermediate 2-2, 0.2mmol of palladium acetate, 30mmol of potassium carbonate, 0.2mmol of tri-tert-butylphosphine, and add 150ml of toluene to make It was dissolved, heated to 80°C until the reaction solution was refluxed, and reacted for 12 hours. After the reaction was complete, water was added to extract the reaction, and the organic phase was extracted with dichloromethane at the same time. The organic phase was combined and washed several times, dried with anhydrous magnesium sulfate, and filtered. The solvent was evaporated to dryness to obtain a crude product, which was purified by flash column chromatography to obtain intermediate 2-3 with a molar weight of 4.39 mmol and a yield of 43.9%. MS (ASAP) = 674.1.

[0141] Synthesis of compound (2):

[01...

Embodiment 3

[0144] The synthetic route of compound (3) is as follows:

[0145]

[0146] Synthesis of Intermediate 3-3:

[0147] Under the atmosphere of nitrogen protection, in a dry three-necked flask, add 10mmol of intermediate 3-1 and 10mmol of intermediate 3-2, 0.2mmol of palladium acetate, 30mmol of potassium carbonate, 0.2mmol of tri-tert-butylphosphine, and add 150ml of toluene to make It was dissolved, heated to 80°C until the reaction solution was refluxed, and reacted for 12 hours. After the reaction was complete, water was added to extract the reaction, and the organic phase was extracted with dichloromethane at the same time. The organic phase was combined and washed several times, dried with anhydrous magnesium sulfate, and filtered. The solvent was evaporated to dryness to obtain a crude product, which was purified by flash column chromatography to obtain intermediate 3-3 with a molar weight of 5.77 mmol and a yield of 57.7%. MS (ASAP) = 774.6.

[0148] Synthesis of comp...

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Abstract

The invention discloses a fused ring compound containing boron atoms and nitrogen atoms and application thereof. The fused ring compound containing the boron atoms and the nitrogen atoms has a structure as shown in a general formula (1). The thermal excitation delayed fluorescence (TADF) characteristic can be conveniently realized in a non-D-A structure. The compound can be used as a TADF luminescent material, the luminescent efficiency and the service life of the compound as an electroluminescent device can be improved by matching with a proper host material, and a solution of the luminescent device which is low in manufacturing cost, high in efficiency, long in service life and low in roll-off is provided.

Description

technical field [0001] The invention relates to the technical field of organic electroluminescence, in particular to condensed ring compounds containing boron atoms and nitrogen atoms and applications thereof. Background technique [0002] Organic semiconductor materials are versatile in synthesis, relatively low in manufacturing cost, and have excellent optical and electrical properties. Organic light-emitting diodes (OLEDs) have great potential in the application of optoelectronic devices such as flat panel displays and lighting. [0003] In order to improve the luminous efficiency of organic light-emitting diodes, various light-emitting material systems based on fluorescence and phosphorescence have been developed. Organic light-emitting diodes using fluorescent materials have the characteristics of high reliability, but their internal electroluminescence quantum The efficiency is limited to 25% because of the 1:3 branching ratio of the singlet excited state to the triple...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F5/02C09K11/06H01L51/54H01L51/50
CPCC07F5/027C09K11/06C09K2211/1055C09K2211/1014C09K2211/1007C09K2211/1011C09K2211/1029C09K2211/1085H10K85/636H10K85/626H10K85/615H10K85/654H10K85/657H10K85/6572H10K50/11
Inventor 宋鑫龙何锐锋宋晶尧
Owner GUANGZHOU CHINARAY OPTOELECTRONICS MATERIALS
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