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Diphenylamine organic neutral free radical electroluminescent material as well as preparation and application thereof

An electroluminescent material, diphenylamine technology, applied in the direction of luminescent material, preparation of organic compounds, preparation of amino compounds, etc., can solve the problems of few types of free radicals, harsh reaction conditions, complicated synthesis steps, etc., to improve the stability , the effect of increasing the degree of conjugation and reducing the electron density

Active Publication Date: 2021-06-01
FUDAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] At present, some progress has been made in material design and device fabrication based on tris(2,4,6-trichlorophenyl)methyl radical derivatives, but they are limited to carbazole-based and aryl-substituted tri( 2,4,6-Trichlorophenyl) methyl radical derivatives, less radical species
In addition, the synthesis of these free radicals is to use a specific base (such as potassium tert-butoxide, tetrabutylammonium hydroxide, etc.) to capture hydrogen ions to form a stable carbanion, and then use a suitable Oxidants (such as chloroquinone, iodine, etc.) oxidize carbanions into free radicals, the synthesis steps are cumbersome, and the conditions of some reactions are relatively harsh

Method used

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  • Diphenylamine organic neutral free radical electroluminescent material as well as preparation and application thereof
  • Diphenylamine organic neutral free radical electroluminescent material as well as preparation and application thereof
  • Diphenylamine organic neutral free radical electroluminescent material as well as preparation and application thereof

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0045] Preparation of compound 1:

[0046]

[0047] Under nitrogen atmosphere, weigh tris(2,4,6-trichlorophenyl)methyl radical (830mg, 1.5mmol), diphenylamine (169mg, 1.0mmol), Pd(OAc) 2 (74mg, 0.33mmol), P(t-Bu) 3 (2.0g, 10wt% toluene solution, 0.99mmol) and Cs 2 CO 3 (1.47g, 4.5mmol), dissolved in 20mL of toluene, heated to 80°C, and reacted for 16 hours. After the reaction was finished, the toluene in the reaction system was removed, and the crude product was separated and purified by silica gel column chromatography to obtain 515 mg of compound 1 with a yield of 75%. Its mass spectrum and single crystal structure were shown in figure 1 , Figure 5 shown. Since the free radical has no NMR signal, it is characterized by high-resolution mass spectrometry, and the product HRMS (ESI, m / z): calculated value, 685.8732; measured value, 685.8728.

Embodiment 2

[0049] Preparation of Compound 2:

[0050]

[0051] Under nitrogen atmosphere, weigh tris(2,4,6-trichlorophenyl)methyl radical (830mg, 1.5mmol), diphenylamine (643mg, 3.8mmol), Pd(OAc) 2 (74mg, 0.33mmol), P(t-Bu) 3 (2.0g, 10wt% toluene solution, 0.99mmol) and Cs 2 CO 3 (1.47g, 4.5mmol), dissolved in 20mL of toluene, heated to 100°C, and reacted for 20 hours. After the reaction, the toluene in the reaction system was removed, and the crude product was separated and purified by silica gel column chromatography to obtain 762 mg of compound 2 with a yield of 62%. Since the free radical has no NMR signal, it is characterized by high-resolution mass spectrometry, and the product HRMS (ESI, m / z): calculated value, 816.9886; measured value, 816.9875.

Embodiment 3

[0053] Preparation of compound 3:

[0054]

[0055] Under nitrogen atmosphere, weigh tris(2,4,6-trichlorophenyl)methyl radical (830mg, 1.5mmol), diphenylamine (896mg, 5.3mmol), Pd(OAc) 2 (74mg, 0.33mmol), P(t-Bu) 3 (2.0g, 10wt% toluene solution, 0.99mmol) and Cs 2 CO 3 (1.47g, 4.5mmol), dissolved in 20mL of toluene, heated to 100°C, and reacted for 36 hours. After the reaction, the toluene in the reaction system was removed, and the crude product was separated and purified by silica gel column chromatography to obtain 856 mg of compound 3 with a yield of 60%. Since the free radical has no nuclear magnetic signal, it is characterized by high-resolution mass spectrometry, and the product HRMS (ESI, m / z): calculated value, 950.1011; measured value, 950.1019.

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Abstract

The invention relates to a diphenylamine organic neutral free radical electroluminescent material and preparation and application thereof, the chemical structural formula of the diphenylamine organic neutral free radical electroluminescent material is shown in the specification, and n is 1, 2 or 3; and the preparation method of the material comprises the following steps: taking a tris (2, 4, 6-trichlorophenyl) methyl free radical compound A and a compound B as initial raw materials, and carrying out Buchwald-Hartwig arylation reaction, thereby obtaining the material. The material is applied to organic electroluminescent devices. Compared with the prior art, the organic neutral free radical electroluminescent material has the advantages of near-infrared absorption, low oxidation potential, good electrochemical stability and the like, and is an organic electroluminescent material with excellent performance. The free radical end product can be obtained from the free radical raw material through one-step reaction, and the method has the advantages of few steps, high yield, low cost and the like.

Description

technical field [0001] The invention belongs to the technical field of organic photoelectric materials, and relates to a diphenylamine organic neutral radical electroluminescent material and its preparation and application. Background technique [0002] The light-emitting principle of organic electroluminescent devices can be simply described as: under the action of an electric field, holes and electrons are injected from the anode and cathode of the device respectively, and they meet in the light-emitting area containing organic fluorescent materials to form excitons, and the excitons retreat. Excited to emit light. Among them, the material selection and design of the organic light-emitting layer have a very important influence on the luminous quality and luminous efficiency of the electroluminescent device. However, in the case where the spin directions of injected electrons and holes are random, the ratio of singlet excitons to triplet excitons is 1:3, and for organic fl...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C211/56C07C211/61C07C209/10C07D213/74C07D333/54C09K11/06H01L51/54
CPCC07C211/56C07C211/61C07D333/54C07D213/74C09K11/06C07C2603/18C09K2211/1007C09K2211/1011C09K2211/1014C09K2211/1029C09K2211/1092H10K85/633H10K85/631H10K85/654H10K85/6576Y02E10/549
Inventor 周刚陆雪峰颜川
Owner FUDAN UNIV
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