Diboroxadibenzo[a,h]anthracene derivatives and their applications

A technology of anthracene derivatives and derivatives, applied in the field of optical and optoelectronic materials, to achieve the effect of promoting development, high thermal decomposition temperature and glass transition temperature, and high luminous quantum efficiency

Active Publication Date: 2021-01-29
ZHEJIANG UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] In addition, PAHs, as materials for organic electronics, pigments, sensors, and liquid-layer displays, have received extensive attention in recent years, and a few synthetic examples of boronaza-PAH compounds have been reported, but are suitable as host materials for electro-optic devices or There are fewer related boronazine polycyclic aromatic hydrocarbon compound materials for luminescent materials.

Method used

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  • Diboroxadibenzo[a,h]anthracene derivatives and their applications
  • Diboroxadibenzo[a,h]anthracene derivatives and their applications
  • Diboroxadibenzo[a,h]anthracene derivatives and their applications

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0043] Embodiment 1: Compound BO1 can be synthesized according to the following route:

[0044]

[0045] Add p-diiodobenzene (6.7327g, 20mmol, 98%, 1.0 equivalents), 2-methoxyphenylboronic acid (6.8245g, 44mmol, 98%, 2.2 equivalents) successively to a dry there-necked flask with a magnetic rotor, Palladium acetate (0.2245 g, 1 mmol, 0.05 equiv) and ligand S-Phos (1.0053 g, 2.4 mmol, 98%, 0.12 equiv). The nitrogen was evacuated three times, and then an aqueous solution (30 mL) of 1,4-dioxane (90 mL) and potassium carbonate (13.8200 g, 100 mmol, 5.0 equiv) was added under nitrogen protection. Then place the three-neck flask in an oil bath at 105°C. After stirring for 16 hours, the reaction was complete as monitored by TLC. After cooling to room temperature, the organic phase was separated, and the aqueous phase was extracted with ethyl acetate (30 mL×2). All organic phases were combined, dried over anhydrous sodium sulfate, filtered, and concentrated. The obtained crude pr...

Embodiment 2

[0049] Embodiment 2: Compound BO77 can be synthesized according to the following route:

[0050]

[0051] Add 1,4-dibromo-2,5-dimethoxybenzene (4.5773g, 15mmol, 97%, 1.0eq), phenylboronic acid (4.1048g, 33mmol, 98%, 2.2 equiv), palladium acetate (0.1010 g, 0.45 mmol, 0.03 equiv), and ligand S-Phos (0.3770 g, 0.9 mmol, 98%, 0.06 equiv). The nitrogen was evacuated three times, and then an aqueous solution (30 mL) of 1,4-dioxane (90 mL) and potassium carbonate (10.3650 g, 75 mmol, 5.0 equiv) was added under nitrogen protection. Then place the three-neck flask in an oil bath at 110°C. After stirring for 17 hours, the reaction was complete as monitored by TLC. After cooling to room temperature, the organic phase was separated, and the aqueous phase was extracted with ethyl acetate (30 mL×2). All organic phases were combined, dried over anhydrous sodium sulfate, filtered, and concentrated. The obtained crude product was recrystallized from n-hexane / dichloromethane to obtain A2...

Embodiment 3

[0055] Embodiment 3: compound BO80 can be synthesized according to the following route:

[0056]

[0057] Add 1,4-dibromo-2,5-dimethoxybenzene (3.0515g, 10mmol, 97%, 1.0 equivalents), 4-methylphenylboronic acid (3.0531 g, 22mmol, 98%, 2.2eq), palladium acetate (0.0674g, 0.3mmol, 0.03eq) and ligand S-Phos (0.2513g, 0.6mmol, 98%, 0.06eq). The nitrogen was evacuated three times, and then an aqueous solution (20 mL) of 1,4-dioxane (60 mL) and potassium carbonate (6.9100 g, 50 mmol, 5.0 equiv) was added under nitrogen protection. Then place the three-neck flask in a 100°C oil bath. After stirring for 19 hours, the reaction was complete as monitored by TLC. After cooling to room temperature, the organic phase was separated, and the aqueous phase was extracted with ethyl acetate (30 mL×2). All organic phases were combined, dried over anhydrous sodium sulfate, filtered, and concentrated. The resulting crude product was recrystallized from n-hexane / dichloromethane to obtain A3, 3...

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Abstract

The invention relates to the technical field of optical and photoelectric materials, and discloses a derivative based on bis-boroxadiphenylanthracene, its preparation method and application. The bis-boroxadibenzo[A,H]anthracene derivative has the characteristics of high quantum efficiency, high thermal decomposition temperature and glass transition temperature, and easy adjustment of the triplet state energy level, so it has great potential in the field of host materials or luminescent materials. Huge application prospects.

Description

technical field [0001] The invention relates to the technical field of optics and optoelectronic materials, in particular to a functional material based on bisboroxadibenzo[A, H]anthracene derivatives, which can be applied in optical or optoelectronic devices. Background technique [0002] Compounds that can absorb and / or emit light are ideal materials for a variety of optical and electroluminescent devices, and can be applied in light-absorbing devices such as solar-sensitive devices and photosensitive devices, organic light-emitting diodes (OLEDs), light-emitting devices, Or devices capable of both light absorption and light emission and as markers for biological applications. Much research has been devoted to the discovery and optimization of organic and organometallic materials for use in optical and electroluminescent devices. In general, research in this area aims to achieve a number of goals, including improvements in absorption and emission efficiency, and improveme...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07F5/02C09K11/06H01L51/46H01L51/54
CPCC07F5/025C09K11/06C09K2211/1007C09K2211/1096H10K85/657
Inventor 李贵杰戴健鑫陈少海
Owner ZHEJIANG UNIV OF TECH
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