A kind of non-aromatic amine small molecule optoelectronic material and its preparation and application

A technology of aromatic amines and optoelectronic materials, which is applied in the direction of luminescent materials, circuits, electrical components, etc., can solve the problems that the exciplex system has not been reported, and achieve good carrier mobility characteristics, high fluorescence quantum yield, and structure single effect

Active Publication Date: 2021-06-08
SOUTH CHINA UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Bimolecular systems based on non-aromatic amine units have small ΔE ST The exciplex system has not been reported so far

Method used

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  • A kind of non-aromatic amine small molecule optoelectronic material and its preparation and application
  • A kind of non-aromatic amine small molecule optoelectronic material and its preparation and application
  • A kind of non-aromatic amine small molecule optoelectronic material and its preparation and application

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0036] The reaction formula of intermediate 1 is as follows:

[0037]

[0038] Concrete reaction steps are as follows:

[0039] Thianthrene (5mmol, 1.08g) was added to a reaction flask containing 100mL of acetic acid, and liquid bromine (5mmol, 800mg) was slowly added dropwise. After passing nitrogen gas for 15 minutes, the reaction was heated at 80° C. for 5 hours. After the reaction, when the system returned to room temperature, sodium bisulfite was added to quench the reaction, extracted with dichloromethane and saturated brine, the organic phase was recovered, and the solvent was distilled off under reduced pressure. The crude product was separated and purified by column chromatography, the eluent was petroleum ether / dichloromethane 5:1, and the obtained intermediate product was dried overnight and dissolved in 60 mL of tetrahydrofuran in the reactor, followed by adding 2-isopropoxy- 4,4,5,5-tetramethyl-1,3,2-dioxaborolane (5mmol, 0.82mL), slowly drop n-butyllithium (...

Embodiment 2

[0041] The reaction formula of intermediate 2 is as follows:

[0042]

[0043] Concrete reaction steps are as follows:

[0044]Compared with intermediate 1, the difference is that thianthrene is replaced by an equivalent amount of dibenzo-p-dioxin, and other raw materials and steps are the same as intermediate 1. Finally, intermediate 2 was obtained with a yield of 92%. Intermediate 2 Molecular formula: C 18 h 19 BO 4 ; Molecular weight: m / z: 310.14; Elemental analysis results: C, 69.71; H, 6.17; B, 3.49; O, 20.63.

Embodiment 3

[0046] The reaction formula of intermediate 3 is as follows:

[0047]

[0048] Concrete reaction steps are as follows:

[0049] Add 2-cyanothiophenol (10mmol, 1.26g), 1,4-dibromo-dinitrobenzene (10mmol, 2.78g), potassium tert-butoxide (30mmol, 3.5g), and DMF 100mL into the reactor in sequence In the process, after passing nitrogen gas for 30 minutes, the reaction was carried out under heating at 160° C. for 24 hours. After the reaction, the system was returned to room temperature, extracted with dichloromethane and saturated brine, the organic phase was recovered, and the solvent was distilled off under reduced pressure. The crude product was separated and purified by column chromatography. The eluent was petroleum ether / dichloromethane 5:1. The obtained intermediate product was dried overnight and dissolved in 80 mL of tetrahydrofuran in the reactor, and then 2-isopropoxy- 4,4,5,5-tetramethyl-1,3,2-dioxaborolane (10mmol, 1.64mL), slowly drop n-butyl lithium (7.5mmol, 5mL...

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Abstract

The invention belongs to the field of optoelectronic materials, and discloses a non-aromatic amine small molecule optoelectronic material as well as its preparation and application. Described non-aromatic amine small molecule optoelectronic material has the structural formula shown in formula (I); In the formula, R 1 selected from H or ‑CH 3 , R 1 , R 2 , R 3 , R 4 each independently selected from S or O. The non-aromatic amine small molecule photoelectric material of the present invention has good hole transport ability, can be applied to the hole transport layer of organic photoelectric devices, and can also be combined with commonly used electron transport materials to generate exciplex state light emission , showing a high fluorescence quantum yield and exhibiting the property of thermally activated delayed fluorescence.

Description

technical field [0001] The invention belongs to the field of optoelectronic materials, and in particular relates to a non-aromatic amine small molecule optoelectronic material and its preparation and application. Background technique [0002] Organic Light Emitting Diode (OLED) devices have great application prospects in the field of flat panel display and solid light source. In order to improve the efficiency of organic photoelectric devices, organic small molecule material systems have the advantages of simple preparation process, stable structure, and convenient purification compared with polymer light-emitting materials, so that higher device efficiency can be obtained, so that it is close to commercial applications. At present, based on the development of small molecules, red, green and blue three-color luminescent materials can be obtained and multilayer flexible devices can be prepared, which has attracted strong attention and made great progress. In recent years, ma...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D339/08C07D327/08C07D411/10C07D409/10C09K11/06H01L51/54
Inventor 苏仕健蔡欣佚邱伟栋李梦珂李彬彬
Owner SOUTH CHINA UNIV OF TECH
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