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Yellow-light electroluminescent material based on 8-hydroxyquinoline zinc metal complex tripolymer and controllable preparation method thereof

A technology of electroluminescent materials and metal complexes, which is applied in the fields of luminescent materials, chemical instruments and methods, semiconductor/solid-state device manufacturing, etc., and can solve unfavorable device production, low synthesis yield, and poor solubility of 8-hydroxy metal derivatives etc. to achieve the effects of good charge transport performance, clear crystal structure and good solubility

Inactive Publication Date: 2015-03-04
GUANGDONG UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0003] As a mature electroluminescent material, 8-hydroxyquinoline metal complex Mqn is widely used in various LEDs. 8-Hydroxyquinoline metal complex Mqn has the characteristics of high fluorescence efficiency, easy purification, and vacuum evaporation film formation. However, there are still the following problems in the research of 8-hydroxyquinoline metal complex Mqn: the research on the synthesis method and purification method of 8-hydroxyquinoline metal complex Mqn is insufficient, and it cannot meet its requirements. Requirements for commercial mass production; research on the luminescent mechanism of 8-hydroxyquinoline metal complexes Mqn is relatively weak, especially the relationship between molecular spatial structure and material properties still needs a lot of research work, the above problems restrict 8 Development of -Hydroxyquinoline Metal Complex Mqn
[0005] However, the existing 8-hydroxyl metal derivatives have poor solubility, which is not conducive to the manufacture of devices, and the synthesis yield is low, which is not conducive to commercial production. No metal single crystal has been obtained, and the metal compound space structure and optical properties have not been targeted. Research

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  • Yellow-light electroluminescent material based on 8-hydroxyquinoline zinc metal complex tripolymer and controllable preparation method thereof
  • Yellow-light electroluminescent material based on 8-hydroxyquinoline zinc metal complex tripolymer and controllable preparation method thereof
  • Yellow-light electroluminescent material based on 8-hydroxyquinoline zinc metal complex tripolymer and controllable preparation method thereof

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Effect test

Embodiment 1

[0033] The controllable preparation method of the yellow photoluminescent material based on the 8-hydroxyquinoline zinc metal complex trimer comprises the following steps:

[0034] (1) Preparation of intermediate (E)-2-[2-(2-fluoro-4-methoxyphenyl)vinyl]-8-acetoxyquinaldine: A, weigh 8-hydroxyquinaldine Pyridine 1.3g and p-methoxybenzaldehyde 1.25g are dissolved in 9ml of acetic anhydride; B, the mixed solution obtained in step A is placed in a 50mL two-necked round-bottomed flask, and magnetically stirred under the protection of nitrogen, Heating to reflux for 19h; C. After the heating to reflux reaction, cool to room temperature, pour the reaction solution into 750mL of ice water, filter when solids are precipitated, extract the filtrate three times with dichloromethane, and combine the organic phases obtained by the three extractions D, wash off the acetic acid in the organic phase with distilled water, use anhydrous sodium sulfate to dry for 4.5h, and then evaporate the so...

Embodiment 2

[0038] The controllable preparation method of the yellow photoluminescent material based on the 8-hydroxyquinoline zinc metal complex trimer comprises the following steps:

[0039] (1) Preparation of intermediate (E)-2-[2-(2-fluoro-4-methoxyphenyl)vinyl]-8-acetoxyquinaldine: A, weigh 8-hydroxyquinaldine Pyridine 1.35g and p-methoxybenzaldehyde 1.3g are dissolved in 10ml of acetic anhydride; B, the mixed solution obtained in step A is placed in a 50mL two-necked round-bottomed flask, and magnetically stirred under the protection of nitrogen, Heating to reflux for 20h; C. After the heating to reflux reaction, cool to room temperature, pour the reaction solution into 780mL of ice water, filter when solids are precipitated, extract the filtrate three times with dichloromethane, and combine the organic phases obtained by the three extractions D, wash off the acetic acid in the organic phase with distilled water, use anhydrous sodium sulfate to dry for 5h, then evaporate the solvent...

Embodiment 3

[0043] The controllable preparation method of the yellow photoluminescent material based on the 8-hydroxyquinoline zinc metal complex trimer comprises the following steps:

[0044] (1) Preparation of intermediate (E)-2-[2-(2-fluoro-4-methoxyphenyl)vinyl]-8-acetoxyquinaldine: A, weigh 8-hydroxyquinaldine Pyridine 1.4g and p-methoxybenzaldehyde 1.35g are dissolved in 11ml of acetic anhydride; B, the mixed solution obtained in step A is placed in a 50mL two-necked round-bottomed flask, and magnetically stirred under the protection of nitrogen, Heating to reflux for 21h; C. After the heating to reflux reaction, cool to room temperature, pour the reaction solution into 850mL of ice water, filter when solids are precipitated, extract the filtrate three times with dichloromethane, and combine the organic phases obtained by the three extractions D, wash off the acetic acid in the organic phase with distilled water, use anhydrous sodium sulfate to dry for 5.5h, and then evaporate the s...

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Abstract

The invention discloses a yellow-light electroluminescent material based on an 8-hydroxyquinoline zinc metal complex tripolymer and a controllable preparation method thereof. According to the controllable preparation method, an electron-withdrawing group and an electron-donating group are simultaneously introduced to a 8-hydroxyquinoline ligand, the electron-withdrawing group has the effects of reducing the electron cloud density of a pyridine ring and enhancing the charge transmission property of the pyridine ring, and the electron-donating group has the function of enhancing the solubility of a complex. The controllable preparation method disclosed by the invention realizes the controllable preparation of a single-crystal structure of the 8-hydroxyquinoline zinc metal complex tripolymer, and the maximum absorption peak of the single-crystal structure is in a yellow-light emitting area of 588 nanometers. The yellow-light electroluminescent material disclosed by the invention has the advantages of good solubility property, good film-forming property, high yield, high luminous efficiency, good stability and low cost and can be used for conveniently processing and manufacturing a large-area display device.

Description

technical field [0001] The invention relates to an 8-hydroxyquinoline zinc metal complex luminescent material with a trimer crystal structure, in particular to a yellow photoluminescence material based on an 8-hydroxyquinoline zinc metal complex trimer and its potential Control the preparation method. Background technique [0002] Organic electroluminescent device OLED is a new type of flat display device, which has the characteristics of energy saving, fast response, stable color, no radiation, long life, light weight and thin thickness. The research on organic electroluminescent device OLED began in the mid-1980s. In 1987, C.W.Tang of the United States invented a luminescent material with outstanding performance using n-bromopropane NPB as the hole transport material and 8-hydroxyquinoline aluminum Alq3 as the light emitting material. The organic electroluminescent device OLED indicates the broad application prospect of the organic electroluminescent device OLED in the di...

Claims

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Application Information

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IPC IPC(8): C09K11/06C07D215/30H01L51/54
Inventor 霍延平陆继果李晓阳赵丰华黄宝华方岩雄张力
Owner GUANGDONG UNIV OF TECH
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