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Anthracene imidazole derivative, organic electroluminescent material and consumer product

A technology of anthrazimidazole and its derivatives, which is applied in the field of organic electroluminescent materials, can solve the problems of low thermal stability and high driving voltage, achieve lower starting voltage, increase π-π conjugation intensity, improve luminous efficiency and The effect of brightness

Active Publication Date: 2021-09-24
BEIJING BAYI SPACE LCD MATERIALS TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

For example, CN103833507B, CN107573328B, CN107556310B publicly authorized by the Chinese Patent Office and TPBI recorded in U.S. Patent No. 5,645,948 published by Kodak in 1996 are materials for the electron transport layer with imidazole groups. In its structure, 1 of benzene , There are three N-phenylbenzimidazole groups in the 3,5 substitution position. In terms of function, it not only has the ability to transport electrons, but also has the function of blocking holes from the light-emitting layer, but in practical applications There are problems of low thermal stability and high driving voltage in components

Method used

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  • Anthracene imidazole derivative, organic electroluminescent material and consumer product
  • Anthracene imidazole derivative, organic electroluminescent material and consumer product
  • Anthracene imidazole derivative, organic electroluminescent material and consumer product

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0064] The preparation method of compound CJHP196 comprises the steps:

[0065] The first step: preparation of intermediate Int-1

[0066]

[0067] 54.5 mmol of 3-iodo-2-cyanonaphthalene (prepared with reference to patent CN104193783A) and 60.0 mmol of phenylacetylene, 5.5 mmol of cuprous iodide, 0.5 mmol of PdCl 2 (PPh 3 ) 2 Catalyst, then add 80 mL of THF and 10 mL of triethylamine, under the protection of nitrogen, stir the reaction at room temperature for 8 hours, filter, concentrate and dry the filtrate under reduced pressure, then separate and purify with silica gel column to obtain Int-1 as a yellow solid, The yield is 94%.

[0068] The second step: the preparation of intermediate Int-2

[0069]

[0070] Dissolve 50.0 mmol of Int-1 in 80 mL of DMSO, add 0.1 mol of nitromethane and 0.1 mol of potassium hydroxide under nitrogen protection, raise the temperature to 110°C and stir for 1 hour, cool to room temperature, add 150 mL Saturated aqueous sodium bisulfite...

Embodiment 2

[0095] With reference to the synthetic method of Example 1, prepare the following compounds, that is, the method steps are the same as in Example 1, the difference is only that according to the desired product, different compounds are used to replace the 3-iodine in the first step of Example 1 according to actual needs -2-cyanonaphthalene and phenylacetylene, replace the 2-naphthylboronic acid in the ninth step of embodiment 1, and change the mass consumption of this compound according to the molar weight, prepare the following compounds:

[0096]

Embodiment 3

[0098] Preparation of Compounds CJHP186, CJHP187, CJHP197 and CJHP198:

[0099] With reference to the synthetic method of Example 1, prepare the following compounds, that is, the method steps are the same as in Example 1, the difference is only that according to the desired product, different compounds are used to replace the 3-iodine in the first step of Example 1 according to actual needs -2-cyanonaphthalene is 6-bromo-3-iodo-2-cyanonaphthalene or 7-bromo-3-iodo-2-cyanonaphthalene, and the mass dosage of the compound is changed according to the molar weight to prepare the compound: CJHP186 , CJHP187, CJHP197 and CJHP198;

[0100] Compound CJHP186, MS(MALDI-TOF): m / z=676.2772 [M+H] + ;

[0101] Compound CJHP187, MS(MALDI-TOF): m / z=676.2726 [M+H] + ;

[0102] Compound CJHP197, MS(MALDI-TOF): m / z=776.3008 [M+H] + ;

[0103] Compound CJHP198, MS(MALDI-TOF): m / z=776.3036 [M+H] + .

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PUM

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Abstract

The invention relates to an anthracene imidazole derivative, an organic electroluminescent material and a consumer product. The structural formula of the anthracene imidazole derivative is as shown in the formula (I) described in the specification. Because of the structure of the anthracene imidazole derivative, the pi-pi conjugation strength of an imidazole ring is increased, and the thermal stability and electron transport capability of the material are improved. For an organic electroluminescent element prepared from the anthracene imidazole derivative, the starting voltage can be obviously reduced, and the luminous efficiency and the brightness can be improved.

Description

technical field [0001] The invention belongs to the technical field of organic electroluminescent materials, and in particular relates to anthrazimidazole derivatives, organic electroluminescent materials and consumer products. Background technique [0002] In general, the organic light-emitting phenomenon refers to a phenomenon in which light is emitted when electric energy is applied to an organic substance. That is, when an organic layer is arranged between an anode and a cathode, when a voltage is applied between the two electrodes, holes are injected from the anode into the organic layer, and electrons are injected from the cathode into the organic layer. When the injected holes and electrons meet, excitons are formed, and when the excitons transition to the ground state, light and heat are emitted. [0003] As a method of effectively manufacturing organic electroluminescent elements, research has been carried out to replace the organic layer in a single-layer manufact...

Claims

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Application Information

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IPC IPC(8): C07D235/02C07D401/04C07D401/14C07D403/10C07D401/10C07D405/04C07D405/14C07D409/04C07D409/14C07F7/08C09K11/06H01L51/50H01L51/54
CPCC07D235/02C07D401/04C07D401/14C07D403/10C07D401/10C07D405/04C07D405/14C07D409/04C07D409/14C07F7/0816C09K11/06H10K85/622H10K85/615H10K85/626H10K85/654H10K85/6576H10K85/6574H10K85/40H10K85/6572H10K50/14H10K50/17H10K50/11
Inventor 韩洪波赵雷唐伟谢佩李程辉王志杰徐先锋李利铮
Owner BEIJING BAYI SPACE LCD MATERIALS TECH
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