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Carbazole ring-containing compound and application thereof

A compound, carbazole ring technology, applied in the field of new carbazole ring-containing compounds

Pending Publication Date: 2020-10-27
北京燕化集联光电技术有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, there is still much room for improvement in the luminescence performance of existing organic electroluminescent materials, and the industry urgently needs to develop new organic electroluminescent materials.

Method used

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  • Carbazole ring-containing compound and application thereof
  • Carbazole ring-containing compound and application thereof
  • Carbazole ring-containing compound and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0055] Example 1 Synthesis of Intermediate P1

[0056] The synthetic route is:

[0057]

[0058] The synthesis specifically includes the following steps:

[0059] (1) Take a 1 liter three-necked flask with magnetic stirring, add 20.35g (0.189mol) of sodium carbonate, 12g (0.1mol) of phenylboronic acid and 100ml of toluene after nitrogen replacement; add 5g (7mmol) Pd132 after nitrogen replacement; add After finishing, heat to 80℃; then start to add dropwise a solution consisting of 27.72g 5,6-dibromopyridin-2-amine (0.11mol) and 100ml toluene, and control the temperature at 75-90℃; after the reaction, separate The organic phase was extracted, dried, column chromatography, and the solvent was spin-dried to obtain 18.675 g of yellow solid P1-1 with a yield of 75%.

[0060] (2) Take a 1 liter three-necked flask with magnetic stirring. After nitrogen replacement, add 20.35g (0.189mol) of sodium carbonate, 24.5g (0.1mol) of (4-chloro-2-nitrophenyl)boronic acid and 100ml of toluene; After...

Embodiment 2

[0065] Example 2 Synthesis of intermediate P2

[0066] The synthetic route is:

[0067]

[0068] The difference between the preparation method and Example 1 is that in step (3), concentrated hydrobromic acid and cuprous bromide are used instead of concentrated hydrochloric acid and cuprous chloride, respectively, and an appropriate material ratio is selected, and other raw materials and steps are uniform. In the same manner as in Example 1, intermediate P2 was obtained.

[0069] Product MS (m / e): 432; Elemental analysis (C 23 H 14 BrClN 2 ): Theoretical value C: 63.69%, H: 3.25%, N: 6.46%; measured value: C: 63.24%, H: 3.50%, N: 6.15%.

Embodiment 3

[0070] Example 3 Synthesis of Compound I-1

[0071]

[0072] The synthetic route is as follows:

[0073]

[0074] The synthesis of compound I-1 includes the following specific steps:

[0075] Take a 1000ml three-necked flask with magnetic stirring. After nitrogen replacement, add 38.8g compound P1 (0.1mol), (4-phenylquinazolin-2-yl)boronic acid 52.5g (0.21mol), cesium carbonate (78g, 0.24) mol) and 500ml of dioxane, start stirring. After replacing with nitrogen again, add (0.8g, 4mmol) tri-tert-butylphosphine and (1.4g, 1.5mmol) tris(dibenzylideneacetone)dipalladium. After the addition, heat to 80-90°C and react for 5 hours , TLC monitors that the reaction is complete. Then the temperature was lowered to room temperature, the pH was adjusted to neutral, the organic phase was separated, extracted, dried, column chromatography, and the solvent was spin-dried to obtain 58.96 g of pale yellow solid I-1 with a yield of 81%.

[0076] Product MS (m / e): 728; Elemental analysis (C 51 H 32 N...

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Abstract

The invention relates to the technical field of organic electroluminescent display, particularly discloses an organic material of a carbazole ring-containing compound, and also discloses application of the organic material in an organic electroluminescent device. The carbazole ring-containing compound provided by the invention is shown as a general formula (I), can be applied to the field of organic electroluminescence, and can be used as a luminescent layer host material. The compound with the structure provided by the invention is applied to an OLED device, and the device has the advantagesof high current efficiency and low working voltage.

Description

Technical field [0001] The present invention relates to the technical field of organic functional materials, in particular to the technical field of materials for organic electroluminescence displays, and specifically discloses a novel compound containing a carbazole ring and its application in organic electroluminescence devices. Background technique [0002] The application of organic electroluminescence (OLED) materials in the fields of information display materials and organic optoelectronic materials has great research value and bright application prospects. With the development of multimedia information technology, the performance requirements of flat panel display devices are getting higher and higher. At present, the main display technologies are plasma display devices, field emission display devices and organic electroluminescence display devices (OLEDs). Among them, OLEDs have a series of advantages such as self-luminescence, low-voltage DC drive, light and thin, power...

Claims

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Application Information

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IPC IPC(8): C07D471/04C07D519/00H01L51/54H01L51/50
CPCC07D471/04C07D519/00H10K85/6565H10K85/654H10K85/6572H10K85/657H10K50/11
Inventor 黄春雪曹占广范洪涛段陆萌杭德余李仲庆班全志陈婷
Owner 北京燕化集联光电技术有限公司
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