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Carbazole-containing eight-membered ring compound and application thereof

A compound and eight-membered ring technology, which is applied in the field of organic electroluminescent materials, can solve the problems that the luminous efficiency and service life of light-emitting elements cannot meet the practical requirements, limit the development of OLED technology, etc., and achieve good thermal stability and film formation Effect of high performance, luminous efficiency and brightness, reduction of power consumption and manufacturing cost

Pending Publication Date: 2022-07-22
BEIJING BAYI SPACE LCD MATERIALS TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

In particular, various organic materials used to make components, their carrier injection, transport performance, material electroluminescence performance, service life, color purity, matching between various materials and electrodes, etc. problem not solved
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-containing eight-membered ring compound and application thereof
  • Carbazole-containing eight-membered ring compound and application thereof
  • Carbazole-containing eight-membered ring compound and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0087] The preparation method of compound D254, comprises the steps:

[0088] Step 1: Preparation of Intermediate Int-1

[0089]

[0090] 22.0 mmol of 2-(2-phenylboronic acid pinacol ester) indole and 20.0 mmol of tert-butyl 4,5-dibromocarbazole-9-carboxylate, 40.0 mmol of anhydrous sodium carbonate, 0.1 mmol of Pd (PPh 3 ) 4 The catalyst was added with 80 mL of toluene, 40 mL of ethanol and 40 mL of water, and under nitrogen protection, the reaction was stirred for 8 hours under heating and reflux, filtered, and the filtrate was concentrated to dryness under reduced pressure, and then separated and purified with a silica gel column to obtain a yellow solid Int-1, Yield: 77%.

[0091] Step 2: Preparation of the intermediate Int-2

[0092]

[0093] 20.0 mmol of Int-1 was dissolved in 120 mL of toluene, under nitrogen protection, 40.0 mmol of sodium tert-butoxide and 0.1 mmol of Pd were added 2 (dba) 3 and 0.2 mmol of Xphos, heated to 100 °C and stirred for 12 hours,...

Embodiment 2

[0098] The preparation method of compound D309 comprises the following steps:

[0099] Step 1: Preparation of the intermediate Int-3

[0100]

[0101] With reference to the synthetic method of the first step of Example 1, only the 2-(2-phenylboronic acid pinacol ester) indole of the first step of Example 1 is replaced with 1-(2-phenylboronic acid pinacol ester) Benzo[d]imidazole to obtain compound Int-3, yellow solid, yield: 82%.

[0102] Step 2: Preparation of the intermediate Int-4

[0103]

[0104] 20.0 mmol of Int-3 was dissolved in 120 mL of toluene, under nitrogen protection, 30.0 mmol of sodium tert-butoxide and 0.1 mmol of Pd were added 2 (dba) 3 and 0.4 mL of 10% tri-tert-butylphosphorus toluene solution, heated to 100°C and stirred for 12 hours, cooled to room temperature, added 50 mL of 3N aqueous dilute hydrochloric acid, extracted with toluene, dried the organic phase, filtered, and concentrated to dryness under reduced pressure. It was passed through a ...

Embodiment 3

[0124] Preparation of compound D388:

[0125]

[0126] 20.0 mmol of Int-2 was dissolved in 60 mL of toluene, under nitrogen protection, 30.0 mmol of sodium tert-butoxide, 24.0 mmol of 2-(2-bromophenyl)-4,6-diphenyl-1 were added, 3,5-Triazine and 0.2 mmol of Pd 2 (dba) 3 and 0.5 mL of 10% tri-tert-butylphosphorus toluene solution, heated to 100 °C and stirred for 12 hours, cooled to room temperature, added 20 mL of water, extracted with toluene, dried the organic phase, filtered, concentrated to dryness under reduced pressure, and passed through silica gel for a short period of time. column, eluted with toluene-dichloromethane, and concentrated to dryness under reduced pressure to obtain a yellow solid, yield: 85%. MS(MALDI-TOF): m / z 664.2509[M+H] + .

[0127] With reference to the similar synthetic method of above-mentioned Example 3, the following compounds were prepared:

[0128]

[0129]

[0130]

[0131]

[0132]

[0133] wherein each G is independentl...

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PUM

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Abstract

The invention relates to an eight-membered ring compound containing carbazole, an organic electroluminescent element, a display device and a lighting device. The carbazole-containing eight-membered ring compound disclosed by the invention has a relatively 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. The material for the organic electroluminescent element, which contains the carbazole-containing eight-membered ring compound, has the characteristics of low starting voltage, high luminous efficiency and high brightness. Besides, the compound provided by the invention has good thermal stability and film-forming property, and can prolong the service life when being applied to materials for organic electroluminescent elements, the 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 belongs to the technical field of organic electroluminescence materials, and in particular relates to an eight-membered ring compound containing carbazole, an organic electroluminescence element, a display device and a lighting device. Background technique [0002] In recent years, organic electroluminescence display technology has matured, and some products have entered the market, but in the process of industrialization, there are still many problems to be solved urgently. Especially for various organic materials used to make components, there are still many more for their carrier injection, transport properties, material electroluminescence properties, service life, color purity, matching between various materials and with each electrode, etc. The problem is not solved yet. In particular, the luminous efficiency and service life of light-emitting elements have not yet met the practical requirements, which greatly limits the developmen...

Claims

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Application Information

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IPC IPC(8): C07D487/16C07D487/06C07D519/00C09K11/06H01L51/50H01L51/54
CPCC07D487/16C07D487/06C07D519/00C09K11/06C09K2211/1044C09K2211/1059C09K2211/1088C09K2211/1092C09K2211/1007C09K2211/1011C09K2211/1048H10K85/622H10K85/615H10K85/6576H10K85/6574H10K85/657H10K85/6572H10K50/11
Inventor 谢佩张海威徐先锋王振宇李利铮李程辉张昊
Owner BEIJING BAYI SPACE LCD MATERIALS TECH
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