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Asymmetric thermal-excitation delayed fluorescence diphenyl ether aromatic phosphine oxide material and synthetic method and application thereof

A delayed fluorescence, aromatic phosphine oxide technology, applied in luminescent materials, chemical instruments and methods, compounds of Group 5/15 elements of the periodic table, etc. It can improve the carrier injection, improve the electron injection and transport ability, and inhibit the interaction effect.

Active Publication Date: 2015-09-02
HEILONGJIANG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0004] The present invention aims to solve the technical problems of high polarity, easy quenching and strong intermolecular interaction of thermally excited delayed fluorescent dyes, and provides an asymmetric thermally excited delayed fluorescent diphenyl ether aromatic phosphine oxide material, synthesized Method and its application

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  • Asymmetric thermal-excitation delayed fluorescence diphenyl ether aromatic phosphine oxide material and synthetic method and application thereof
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  • Asymmetric thermal-excitation delayed fluorescence diphenyl ether aromatic phosphine oxide material and synthetic method and application thereof

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specific Embodiment approach 1

[0059] Specific embodiment 1: In this embodiment, the asymmetric thermally excited delayed fluorescence diphenyl ether aromatic phosphine oxide material introduces 2, 3, or 4 diphenyl ethers at the 2, 2', 4, 4'positions of the diphenyl ether, respectively It is composed of phosphinooxy groups and its general structure is as follows:

[0060] Where X is H or Ph 2 OP, Y is H or Ph 2 OP, Z is H or Ph 2 OP.

[0061] When X and Y are H, Z is Ph 2 In the case of OP, the compound is 2,4DPEDPO, and its structural formula is (II);

[0062] When Y is Ph 2 When OP, X and Z are H, the compound is 2,4’DPEDPO, and its structural formula is (III);

[0063] When Y and Z are Ph 2 When OP and X are H, the compound is 2,4,4’DPETPO, and its structural formula is (IV);

[0064] When X and Y are Ph 2 When OP and Z are hydrogen, the compound is 2,2,4DPETPO, and its structural formula is (V);

[0065] When X, Y, and Z are all Ph 2 In OP, the compound is 2,2,4,4,DPEQPO, and its structural formula is (VI);

[00...

specific Embodiment approach 2

[0068] Specific embodiment 2: Specific embodiment 1 The synthesis method of the asymmetric thermally excited delayed fluorescence diphenyl ether aromatic phosphine oxide material is as follows:

[0069] Mix 1mmol bromodiphenylphosphinooxyphenyl ether, 3-6mmol diphenylphosphine, 3-6mmol anhydrous sodium acetate, 0.005-0.01mmol palladium acetate and 5-10ml DMF, and react for 10 to 36 hours Then pour into ice water and extract to obtain an organic layer. After the organic layer is dried, add 1ml H 2 O 2 After oxidation, extraction and drying, column chromatography purification with a mixed solvent of ethanol and ethyl acetate as the eluent to obtain polyphosphine oxide phenyl ether phosphine oxide;

[0070] Wherein the ratio of the amount of diphenylphosphine to brominated diphenylphosphino phenyl ether in step 2 is (1~2): 1, the amount of palladium acetate and brominated diphenylphosphino phenyl ether substance The ratio is (0.001~0.002):1, and the ratio of sodium acetate to brominat...

specific Embodiment approach 3

[0071] Specific embodiment three: This embodiment is different from the specific embodiment two in that the volume ratio of ethanol to ethyl acetate in the mixed solvent of ethanol and ethyl acetate is 1:20. Others are the same as the first or second embodiment.

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Abstract

The invention provides an asymmetric thermal-excitation delayed fluorescence diphenyl ether aromatic phosphine oxide material and a synthetic method and application thereof and aims at solving the technical problem that the thermal-excitation delayed fluorescence diphenyl ether aromatic phosphine oxide material is large in polarity, is easily quenched and is strong in intermolecular effect. The asymmetric thermal-excitation delayed fluorescence diphenyl ether aromatic phosphine oxide material is formed by introducing 2, 3 or 4 diphenylphosphine oxygen groups to 2, 2', 4 and 4' positions of diphenyl ether. The synthetic method comprises the steps of mixing bromo-diphenyl phosphine oxide phenylate, diphenylphosphine, anhydrous sodium acetate, palladium acetate and DMF, pouring a mixture into icy water to perform extraction, obtaining an organic layer for oxidation and performing extraction, drying and purification. The asymmetric thermal-excitation delayed fluorescence diphenyl ether aromatic phosphine oxide material can effectively inhibit mutual intermolecular effect and accordingly inhibit quenching effect. The asymmetric thermal-excitation delayed fluorescence diphenyl ether aromatic phosphine oxide material serves as a light-emitting layer and used for preparing electro-phosphorescence devices.

Description

Technical field [0001] The invention relates to an aromatic phosphine oxygen main body material, a synthesis method and an application thereof. Background technique [0002] High-efficiency, low-voltage driven organic electroluminescence has brought revolutionary innovations to the development of light-emitting diodes. The research on organic light-emitting materials and devices has attracted widespread attention and in-depth research. Organic electroluminescent diodes are called the third-generation flat display and lighting technology. They have outstanding advantages in energy saving and environmental protection. In order to effectively utilize the singlet and triplet excitons generated in the electroluminescence process, it is currently widely used The method is to use phosphorescent dyes to construct electro-phosphorescence, but the heavy metals involved in phosphorescent dyes are not only expensive but also pollute the environment, and it is urgent to use other materials t...

Claims

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Application Information

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IPC IPC(8): C07F9/53C09K11/06H01L51/54
Inventor 许辉张静丁冬雪
Owner HEILONGJIANG UNIV
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