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Non-aromatic amine small molecule photoelectric material and preparation and application thereof

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 the effect of good carrier transfer characteristics and high fluorescence quantum yield

Active Publication Date: 2019-05-21
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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  • Non-aromatic amine small molecule photoelectric material and preparation and application thereof
  • Non-aromatic amine small molecule photoelectric material and preparation and application thereof
  • Non-aromatic amine small molecule photoelectric material and preparation and application thereof

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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 photoelectric materials, and discloses a non-aromatic amine small molecule photoelectric material and preparation and application thereof. The non-aromatic aminesmall molecule photovoltaic material has a structural formula as shown in the formula (I). In the formula, R1 is selected from H or -CH3; and R1, R2, R3, and R4 are independently selected from S or O.The non-aromatic amine small molecule photoelectric material of the invention has good hole transport ability, can be applied to a hole transport layer of an organic photoelectric device, and can also be combined with a common electron transport type material to generate an exciplex for luminescence, exhibits high fluorescence quantum yield and exhibits the property of thermally activated delayedfluorescence.

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 Applications(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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