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N-heterocyclic carbazole compound and application thereof

A compound and carbazole technology, applied in the field of deep blue light materials, to achieve the effects of simple operation, mild synthesis conditions and excellent film-forming properties

Active Publication Date: 2022-01-28
GUANGDONG UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0004] At present, organic light-emitting materials containing azacarbazole-imidazole units and organic light-emitting materials based on acridine-azacarbazole units have been prepared. potential, but there are still few types of nitrogen-heterocyclic carbazole compounds. Therefore, it is urgent to develop more novel nitrogen-heterocyclic carbazole compounds suitable for the preparation of light-emitting materials.

Method used

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  • N-heterocyclic carbazole compound and application thereof
  • N-heterocyclic carbazole compound and application thereof
  • N-heterocyclic carbazole compound and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0092] Embodiment 1 Preparation of a nitrogen heterocyclic carbazole compound (A1)

[0093] S1. Mix 3,6-di-tert-butyl-9H-carbazole (1.12g, 4.0mmol), 1-bromo-4-iodobenzene, cuprous iodide, and potassium carbonate at a molar ratio of 1:1.2:0.2:2 Add 20mL of anhydrous N,N-dimethylformamide to a two-necked flask, vacuumize the flask and replace it in dry nitrogen three times, heat and reflux under nitrogen at 140°C and stir for 12h, then cool and filter , extracted with ethyl acetate, the organic layer was separated and dried with anhydrous magnesium sulfate, filtered and evaporated, the crude product was subjected to column chromatography (petroleum ether as eluent) to obtain 1.15 g of white powder (intermediate M1, yield was 66%).

[0094] The reaction formula is as follows:

[0095]

[0096] S2. The intermediate M1 (521 mg, 1.20 mmol), 2,4-biphenyl-6-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaboron) obtained in step S1 Alkyl-2-yl)phenyl)-1,3,5-triazine, tetrakis(triphenylphosphin...

Embodiment 2

[0098] Embodiment 2 Preparation of a nitrogen heterocyclic carbazole compound (A2)

[0099]S1. Mix 3,6-di-tert-butyl-9H-carbazole (279mg, 1.2mmol), methyl 5-bromo-2-iodobenzoate, cuprous iodide, and potassium carbonate at a ratio of 1:1.2:0.2:2 The molar ratio was added to a two-neck flask containing 5 mL of anhydrous N,N-dimethylformamide, the flask was evacuated and replaced in dry argon three times, and heated under reflux at 140°C under argon and stirred for 12 hours. , cooled, filtered, extracted with ethyl acetate, the organic layer was separated and dried with anhydrous magnesium sulfate, filtered and evaporated, the crude product was subjected to column chromatography (petroleum ether as eluent) to obtain 365 mg of white powder (intermediate M2 , the yield was 74%). The reaction formula is as follows:

[0100]

[0101] S2. Add phenylmagnesium bromide into the flask under argon and stir, then slowly add 1 mL of tetrahydrofuran dissolved in intermediate M2 (365 mg, ...

Embodiment 3

[0105] Embodiment 3 Preparation of a nitrogen heterocyclic carbazole compound (A1)

[0106] S1. Mix 3,6-di-tert-butyl-9H-carbazole (1.12g, 4.0mmol), 1-bromo-4-iodobenzene, cuprous iodide, and potassium carbonate at a molar ratio of 1:1.2:0.3:3 Pour into a two-necked flask filled with 20 mL of anhydrous dimethyl sulfoxide, vacuumize the flask and replace it in dry argon three times, heat and reflux under argon at 120°C for 15 h, cool, filter, and use Extracted with ethyl acetate, the organic layer was separated and dried with anhydrous magnesium sulfate, filtered and evaporated, the crude product was subjected to column chromatography (eluent was petroleum ether) to obtain 1.06g white powder (intermediate M1, yield: 61 %). Reaction formula is with embodiment 1.

[0107] S2. The intermediate M1 (521 mg, 1.20 mmol), 2,4-biphenyl-6-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaboron) obtained in step S1 Alkyl-2-yl)phenyl)-1,3,5-triazine, tetrakis(triphenylphosphine)palladium, and potassiu...

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Abstract

The invention provides an N-heterocyclic carbazole compound and an application thereof. As a low-cost dark blue light organic light-emitting small molecule, the N-heterocyclic carbazole compound has good thermal stability, better film-forming property, stronger emission brightness, higher fluorescence quantum yield and better electron transmission capability, the N-heterocyclic carbazole compound is wide in preparation raw material source, low in price and mild in synthesis condition, and the operation is simple.

Description

technical field [0001] The invention belongs to the technical field of deep blue light materials. More specifically, it relates to a nitrogen heterocyclic carbazole compound and its application. Background technique [0002] Due to its light weight, good flexibility, short response time, wide viewing angle, wide operating temperature range, high brightness and contrast, organic light-emitting diodes have gradually become the focus of extensive research by scholars. After decades of development, the technology related to organic light emitting diodes has become increasingly mature, and is widely used in two fields of full-color display and white lighting, especially in the fields of flat panel display and solid-state light-emitting display technology products, which are more widely acclaimed. [0003] Organic light-emitting materials are the core part of organic light-emitting diodes, so properties such as emission brightness and fluorescence quantum yield of organic light-e...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D403/10C07D471/06C09K11/06H01L51/50H01L51/54
CPCC07D403/10C07D471/06C09K11/06C09K2211/1007C09K2211/1029C09K2211/1059H10K85/654H10K85/6572H10K50/11
Inventor 陈国威陈文铖霍延平巫浩瀚陈思维梁辉张浩力籍少敏
Owner GUANGDONG UNIV OF TECH
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