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Carbazole derivative and application thereof

A technology of carbazole derivatives and groups, which is applied in the field of materials for organic electroluminescent elements, can solve the problems that the luminous efficiency and service life of light-emitting elements cannot meet the practical requirements, and limit the development of OLED technology.

Active Publication Date: 2021-03-05
BEIJING BAYI SPACE LCD MATERIALS TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0002] In recent years, organic electroluminescent display technology has become mature, and some products have entered the market, but there are still many problems to be solved in the process of industrialization, especially the various organic materials used to make components, their current-carrying Injection, transport performance, material electroluminescent performance, service life, color purity, matching between various materials and electrodes, etc., there are still many problems that have not yet been resolved.
In particular, the luminous efficiency and service life of light-emitting elements have not yet met the practical requirements, which greatly limits the development of OLED technology.

Method used

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  • Carbazole derivative and application thereof
  • Carbazole derivative and application thereof
  • Carbazole derivative and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0066] The preparation method of intermediate Int-2, comprises the steps:

[0067] The first step: preparation of compound Int-1

[0068]

[0069] Mix 0.9mol of 1-bromocarbazole, 1.1mol of 1,8-dibromonaphthalene and 2000mL of xylene, and add 1.2mol of sodium tert-butoxide and 4.5mmol of Pd under nitrogen protection 2 (dba) 3 CHCl 3 and 2.0 mL of 10% tri-tert-butylphosphonium toluene solution, heated to 110 ° C, stirred for 15 hours, cooled to room temperature, diluted with 200 mL of water, extracted with toluene, collected organic phase, dried, filtered, and the filtrate was concentrated under reduced pressure to dryness. Recrystallized from ethanol to obtain the intermediate Int-2 as a yellow solid with a yield of 72%.

[0070] The second step: the preparation of intermediate Int-2

[0071]

[0072] Dissolve 0.5mol of intermediate Int-1 in 2000mL of dry toluene, under nitrogen protection, add 0.55mol of p-chloroaniline and 1.5mol of sodium tert-butoxide, and then ad...

Embodiment 2

[0074] The preparation method of intermediate Int-4, comprises the steps:

[0075] The first step: preparation of compound Int-3

[0076]

[0077] Dissolve 0.75mol of 1-aminocarbazole in 2200mL of dry toluene, add 0.5mol of 1,8-dibromonaphthalene and 0.75mol of sodium tert-butoxide, and then add 2.5mmol of Pd 2 (dba) 3 and 5.0mmol of Xantphos, heated to 100°C, stirred for 12 hours, cooled to room temperature, diluted with 100mL of water, extracted with toluene, collected organic phase, dried, filtered, the filtrate was concentrated to dryness under reduced pressure, separated and purified with silica gel column, ethanol Recrystallization gave the intermediate Int-3 as a white solid with a yield of 75%.

[0078] The second step: the preparation of compound Int-4

[0079]

[0080] 0.5 mol of intermediate Int-3 was dissolved in 2000 mL of dry xylene, under nitrogen protection, 0.75 mol of sodium tert-butoxide and 2.0 mmol of Pd were added 2 (dba) 3 CHCl 3 and 1.0mL of...

Embodiment 3

[0082] Preparation of compound CJHK021, with T 1 Take the N-phenyl compound CJHK021-1 as an example:

[0083]

[0084] 10.0mmol of intermediate Int-2 was dissolved in 60mL of toluene, and under nitrogen protection, 12.0mmol of N-phenyl-3-carbazole boronic acid (PC-boric acid), 24.0mmol of anhydrous potassium carbonate and 0.01mmol of Pd(PPh 3 ) 4 Catalyst, heated and refluxed and stirred for 12 hours, cooled to room temperature, diluted with 50 mL of water, extracted with dichloromethane, collected the lower organic phase, dried, filtered, the filtrate was concentrated to dryness under reduced pressure, and the solid was separated and purified with a silica gel column to obtain the compound CJHK021- 1. Yellow solid, yield 86%.

[0085] MS of compound CJHK021-1 and 1 HNMR test results are as follows:

[0086] MS (MALDI-TOF): m / z 624.2455 [M+H] + ; 1 HNMR (δ, CDCl 3 ): 8.19~8.15(3H,m); 7.98~7.96(1H,d); 7.72~7.65(4H,m); 7.58~7.51(7H,m); 7.44~7.31(8H,m); 7.26~7.22 (4H,...

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Abstract

The invention relates to the technical field of materials for organic electroluminescent elements, in particular to a carbazole derivative and application thereof. The structure of the carbazole derivative is shown as a formula (I). The carbazole derivative has a high triplet state energy level and a high glass transition temperature, and is suitable for being used as a material for an organic electroluminescent element, and the material for the organic electroluminescent element containing the carbazole derivative has the characteristics of low starting voltage, high luminous efficiency and high brightness. Besides, the carbazole derivative has good thermal stability and film-forming property, and can prolong the service life when applied to materials for organic electroluminescent elements, organic electroluminescent elements, display devices and lighting devices. Therefore, the manufacturing cost of the material for the organic electroluminescent element, the organic electroluminescent element, the display device and the lighting device can be reduced.

Description

technical field [0001] The invention relates to the technical field of materials for organic electroluminescent elements, in particular to carbazole derivatives and applications thereof. Background technique [0002] In recent years, organic electroluminescence display technology has become mature, and some products have entered the market, but there are still many problems to be solved in the process of industrialization, especially the various organic materials used to make components, their current-carrying Injection, transport performance, material electroluminescence performance, service life, color purity, matching between various materials and electrodes, etc., there are still many problems that have not been resolved. In particular, the luminous efficiency and service life of light-emitting elements have not yet met the practical requirements, which greatly limits the development of OLED technology. [0003] Organic electroluminescence is mainly divided into fluores...

Claims

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Application Information

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IPC IPC(8): C07D487/06C07D519/00C09K11/06H01L51/50H01L51/54H01L51/52
CPCC07D487/06C07D519/00C09K11/06C09K2211/1011C09K2211/1014C09K2211/1029C09K2211/1044C09K2211/1059C09K2211/1088C09K2211/1092H10K85/622H10K85/624H10K85/626H10K85/615H10K85/654H10K85/6576H10K85/6574H10K85/6572H10K50/15H10K50/18H10K50/8426H10K50/11Y02E10/549
Inventor 曹建华戴雄谢佩李程辉程友文白爽王学涛
Owner BEIJING BAYI SPACE LCD MATERIALS TECH
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