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Boron-containing heterocyclic organic compound, mixture, composition, and organic electronic device

A technology of organic compounds and boron heterocycles, applied in the field of electroluminescent materials, can solve problems such as performance gaps, and achieve the effect of improving luminous efficiency and lifespan

Pending Publication Date: 2022-02-25
GUANGZHOU CHINARAY OPTOELECTRONICS MATERIALS
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] The existing red and green TADF materials have been developed for a period of time, and have achieved certain results in many aspects of performance. However, compared with phosphorescent materials, their performance still has certain limitations in terms of efficiency and life. gap

Method used

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  • Boron-containing heterocyclic organic compound, mixture, composition, and organic electronic device
  • Boron-containing heterocyclic organic compound, mixture, composition, and organic electronic device
  • Boron-containing heterocyclic organic compound, mixture, composition, and organic electronic device

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0152] The synthetic route of compound (1) is as follows:

[0153]

[0154] (1) Synthesis of Intermediate 1-3:

[0155] Under nitrogen protection atmosphere, in a dry three-necked flask, add 10mmol intermediate 1-1 and 10mmol intermediate 1-2, 0.2mmol palladium acetate, 1.38 grams of potassium carbonate respectively, add 150mL of tetrahydrofuran to dissolve it, and heat to 80 ℃ to the reaction liquid reflux, react for 12 hours, after the reaction is complete, add water to extract the reaction, and at the same time extract the organic phase with dichloromethane, combine and wash the organic phase several times, dry with anhydrous magnesium sulfate, filter, and rotary evaporate to dryness to obtain Coarse, purified by flash column chromatography to obtain 5.74 mmol of intermediate 1-3, yield: 57.4%. MS (ASAP) = 434.2.

[0156] (2) Synthesis of Intermediate 1-5:

[0157] Under a nitrogen atmosphere, add 1 mmol of intermediate 1-3 and 1 mmol of intermediate 1-4 to a dry thre...

Embodiment 2

[0161] The synthetic route of compound (2) is as follows:

[0162]

[0163] (1) Synthesis of intermediate 2-3:

[0164] Under nitrogen protection atmosphere, in a dry three-necked flask, add 10mmol intermediate 2-1 and 10mmol intermediate 2-2, 0.2mmol palladium acetate, 1.38 g potassium carbonate respectively, add 150mL tetrahydrofuran to dissolve it, and heat to 80°C until the reaction solution was refluxed, and reacted for 12 hours. After the reaction was complete, the reaction was extracted with water, and the organic phase was extracted several times with dichloromethane. , and purified by flash column chromatography to obtain intermediate 2-3 with a molar weight of 6.93 mmol and a yield of 69.3%. MS (ASAP) = 924.1.

[0165] (2) Synthesis of intermediate 2-5:

[0166] Under a nitrogen atmosphere, add 1 mmol of intermediate 2-3 and 1 mmol of intermediate 2-4 to a dry three-necked flask, pour 100 mL of DMSO into a solvent, add dry K 2 CO 3 As a base, react at 120°C f...

Embodiment 3

[0170] The synthetic route of compound (3) is as follows:

[0171]

[0172] (1) Synthesis of intermediate 3-3:

[0173]Under nitrogen protection atmosphere, in a dry three-necked flask, add 10mmol intermediate 3-1 and 10mmol intermediate 3-2, 0.2mmol palladium acetate, 1.38 g potassium carbonate respectively, add 150mL tetrahydrofuran to dissolve it, and heat to 80°C until the reaction solution was refluxed, and reacted for 12 hours. After the reaction was complete, the reaction was extracted with water, and the organic phase was extracted several times with dichloromethane. , and purified by flash column chromatography to obtain intermediate 3-3 with a molar weight of 6.72 mmol and a yield of 67.2%. MS (ASAP) = 321.4.

[0174] (2) Synthesis of Intermediate 3-5:

[0175] Under a nitrogen atmosphere, add 1 mmol of intermediate 3-3 and 1 mmol of intermediate 3-4 to a dry three-necked flask, pour 100 mL of DMSO into a solvent, add dry K 2 CO 3 As a base, react at 120°C fo...

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Abstract

The invention relates to a boron-containing heterocyclic organic compound, a mixture, a composition and an organic electronic device. The organic compound containing the boron heterocyclic ring has a structure as shown in a formula (1), and can improve the electroluminescent efficiency and prolong the service life of a device when being used in a luminescent material organic electronic device.

Description

technical field [0001] The present invention relates to the field of electroluminescent materials, in particular to a boron heterocycle-containing organic compound, mixture, composition and organic electronic device. Background technique [0002] Due to the diversity of synthesis, relatively low manufacturing cost and excellent optical and electrical properties of organic semiconductor materials, their application in optoelectronic devices, especially OLED devices, has great potential. [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 the branching ratio of the singlet excited state to the triplet excited state of the excitons is 1:3. In contrast, ...

Claims

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Application Information

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IPC IPC(8): C07F5/02H01L51/54
CPCC07F5/02C09K2211/1055C09K2211/1085H10K85/657H10K85/6572
Inventor 宋鑫龙何锐锋肖志华宋晶尧
Owner GUANGZHOU CHINARAY OPTOELECTRONICS MATERIALS
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