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Anthracene derivative and preparation method and application thereof

An anthracene derivative and naphthalene anthracene technology, applied in the field of anthracene derivatives and their preparation, can solve the problems of insufficient color purity, intramolecular charge transfer, fluorescence quenching and the like, and achieve the effect of a simple preparation method

Pending Publication Date: 2020-10-30
GUANGDONG UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

So far, although there have been many reports on anthracene-based light-emitting materials used in small-molecule organic electroluminescent devices, most of them are in the aggregated state due to the formation of π-π stacking due to the planar structure of the molecules, resulting in the quenching of their fluorescence. , thereby reducing the device efficiency
[0003] Anthracene-based light-emitting materials modified with traditional groups, due to the general electron transport and hole transport capabilities of their molecules, lead to unbalanced carrier transport and poor device performance in devices using it as the light-emitting layer
Moreover, due to the strong electron-donating or electron-withdrawing ability between the modifying group and the anthracene group, the modified molecule has a serious intramolecular charge transfer phenomenon, which makes the luminescence red-shifted and the color purity is not enough, which affects the application of the material.
Chinese patent CN108586367A discloses an organic luminescent material. The organic luminescent material is a structure in which an asymmetric anthracene is connected to a triazine with good electron transport performance. It is obtained by modifying the structure of anthracene-containing derivatives. Reach the deep blue emission of international standard OLED devices (x+y<0.30)

Method used

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  • Anthracene derivative and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0042] Embodiment 1 provides a kind of anthracene derivative, the preparation method of this anthracene derivative is as follows:

[0043] P-bromo-naphthalene anthracene (1.15g, 3mmol), tetraphenylnaphthaleneboronic acid (2.51g, 4.5mmol) and tetrakistriphenylphosphine palladium (0.16g, 0.21mmol) were added in a 100ml two-necked flask, and the flask was Evacuated under vacuum and replaced three times in dry nitrogen;

[0044] Add 60 mL THF and 8 mL saturated K 2 CO 3 Aqueous solution, heated to reflux and stirred at 90°C for 48 hours to obtain a mixed solution;

[0045] Use saturated brine and dichloromethane to extract the above mixed solution, distill under reduced pressure to obtain a black solid, which is purified by column chromatography, wherein the stationary phase is silica gel powder, and the eluent is petroleum ether / dichloromethane to obtain anthracene Derivative An-TNa1, 1.0 g in total, yield 80%.

[0046] The reaction process is as follows:

[0047]

Embodiment 2

[0049] Embodiment 2 provides a kind of anthracene derivative, the preparation method of this anthracene derivative is as follows:

[0050] Two-p-bromoanthracene (1.01g, 3mmol), tetraphenylnaphthaleneboronic acid (5.02g, 9mmol) and tetrakistriphenylphosphine palladium (0.16g, 0.21mmol) were added in a 100ml two-necked flask, and the flask was placed under vacuum Evacuate and replace three times in dry nitrogen;

[0051] Add 60 mL THF and 8 mL saturated K 2 CO 3 Aqueous solution, heated to reflux and stirred at 90°C for 48 hours to obtain a mixed solution;

[0052]Use saturated brine and dichloromethane to extract the above mixed solution, and distill under reduced pressure to obtain a black solid; it is purified by column chromatography, wherein the stationary phase is silica gel powder, and the eluent is petroleum ether / dichloromethane to obtain anthracene Derivative An-TNa2, a total of 1.69g, yield 66.7%.

[0053] The reaction process is as follows:

[0054]

Embodiment 3

[0056] Example 3 provides an anthracene derivative. The difference between its preparation method and Example 1 is that the addition amount of tetraphenylnaphthalene boronic acid is 3 mmol, and the addition amount of tetrakistriphenylphosphine palladium is 0.15 mmol.

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Abstract

The invention discloses an anthracene derivative and a preparation method and application thereof. The anthracene derivative is prepared by mixing bromo-anthracene, tetraphenylnaphthaleneboronic acidand a catalyst and carrying out Suzuki reaction in the presence of strong base under the protection of inert gas. By introducing a tetraphenyl naphthalene group, the carrier injection and transmissionof the anthracene derivative are more balanced; the charge transfer effect between an electron donor and an acceptor is balanced, the dark blue emission of a solid-state thin film can be maintained while the aggregation-state high fluorescence quantum efficiency of the solid-state thin film is achieved, and organic light-emitting small molecules with good carrier transport capacity and high fluorescence quantum yield in an aggregation state are synthesized.

Description

technical field [0001] The present invention relates to the field of organic luminescent materials, and more specifically, to an anthracene derivative and its preparation method and application. Background technique [0002] With the rise of high-tech products such as large-screen smartphones, tablet computers, and wearable devices, traditional liquid crystal display materials are becoming more and more difficult to meet the increasingly thinner and lower power consumption requirements of mobile terminals. Humans have begun to pay attention to organic electroluminescent devices with advantages such as higher flexibility, thinner thickness, lower power consumption, wider viewing angle, and higher color saturation. Among them, OLED devices are of decisive significance to display technologies such as full-color display and solid-state lighting. So far, although there have been many reports on anthracene-based light-emitting materials used in small-molecule organic electrolumin...

Claims

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Application Information

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IPC IPC(8): C07C15/60C07C1/32C09K11/06H01L51/50H01L51/54
CPCC07C15/60C07C1/321C09K11/06C07C2531/24C09K2211/1007C09K2211/1011C07C2603/24H10K85/626H10K85/615H10K50/11
Inventor 陈文铖邱志鹏霍延平李振声
Owner GUANGDONG UNIV OF TECH
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