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Phosphinosulfenyl electron transfer material, and preparation method and application thereof

An electron transport material, phosphine-thio-based technology, applied in chemical instruments and methods, circuits, electrical components, etc., can solve problems such as poor luminous efficiency, poor thermal stability, and short service life of components, and achieve excellent electron transport The effects of performance, novel structure, and high electron mobility

Inactive Publication Date: 2015-01-21
OCEANS KING LIGHTING SCI&TECH CO LTD +2
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The carrier mobility of traditional electron transport materials is one-thousandth of that of hole transport materials, and the thermal stability is not good. Therefore, it often leads to problems such as poor luminous efficiency or short service life of components. According to relevant literature , the charge consumption ratio of electron transport materials is 35.9%, which is second only to the consumption of the light-emitting layer (39.8%). Therefore, the development of high-carrier electron transport materials is the focus of current OLED material development.
[0003] Alq 3 Because of its good film-forming properties, it is the main emitter of electron transport materials commonly used at present, but there are some carrier mobility and T g Higher than Alq 3 The emergence of materials, such as metal (Be, Al, Zn) complexes, 1,2,4-phosphine sulfur (TAZ) derivatives, fluorine-containing compounds and silicon-containing compounds, etc., however, these known materials carry The ion mobility is still poor, and there are problems such as poor thermal stability or low current density when used in devices. Therefore, the development of new electron transport materials is a very important topic.

Method used

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  • Phosphinosulfenyl electron transfer material, and preparation method and application thereof
  • Phosphinosulfenyl electron transfer material, and preparation method and application thereof
  • Phosphinosulfenyl electron transfer material, and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0029] The preparation steps of the phosphinethio-based electron transport material of this example, namely 2,8-bis(4-(diphenylphosphinethio)phenyl)dibenzo[b,d]thiophene sulfone, are as follows:

[0030]

[0031] Under argon protection, 2,8-dibromodibenzo[b,d]thiophene sulfone (75mg, 0.2mmol), diphenyl(4-pinacol borate phenyl)phosphinesulfur (168mg, 0.4mmol) was added to a flask containing 10ml of toluene solvent, and after fully dissolving, potassium carbonate (2mL, 2mol / L) solution was added to the flask, vacuumed to remove oxygen and filled with argon, and then bistriphenylphosphine di Palladium chloride (5.6mg, 0.008mmol); the flask was heated to 90°C for Suzuki coupling reaction for 36h. Subsequently, the polymerization reaction was stopped after cooling down, and 50 ml of methanol was added dropwise to the flask for sedimentation; after filtering through a Soxhlet extractor, the mixture was sequentially extracted with methanol and n-hexane for 24 hours. Then use chlo...

Embodiment 2

[0034] The preparation steps of the phosphinethio-based electron transport material of this example, namely 2,8-bis(4-(diphenylphosphinethio)phenyl)dibenzo[b,d]thiophene sulfone, are as follows:

[0035]

[0036] Under the protection of mixed gas of nitrogen and argon, 2,8-dibromodibenzo[b,d]thiophenesulfone (112mg, 0.3mmol), diphenyl(4-pinacol borate phenyl)phosphinesulfur (252mg, 0.6mmol) and 15mL of tetrahydrofuran were added to a 50mL two-necked bottle, fully dissolved, and a mixture of nitrogen and argon was introduced to exhaust the air for about 20 minutes, and then tetrakistriphenylphosphine palladium (4mg, 0.003mmol) was added Among them, sodium bicarbonate (3mL, 2mol / L) solution was added after fully dissolved. Then, the mixed gas of nitrogen and argon was exhausted for about 10 minutes, and the two-neck flask was added to 70°C for Suzuki coupling reaction for 96 hours. Subsequently, the polymerization reaction was stopped after cooling down, and 40 mL of methano...

Embodiment 3

[0038] The preparation steps of the phosphinethio-based electron transport material of this example, namely 2,8-bis(4-(diphenylphosphinethio)phenyl)dibenzo[b,d]thiophene sulfone, are as follows:

[0039]

[0040] Under nitrogen protection, 2,8-dibromodibenzo[b,d]thiophenesulfone (112mg, 0.3mmol), diphenyl(4-pinacol borate phenyl)phosphinesulfur (277mg, 0.66mmol ), palladium acetate (3.5mg, 0.015mmol) and tris(o-methoxyphenyl)phosphine (21mg, 0.06mmol) were added to a flask containing 12mL of N,N-dimethylformamide, and after fully dissolving Potassium carbonate (3mL, 2mol / L) solution was added, and then the flask was purged with nitrogen for about 30min; the flask was heated to 130°C for Suzuki coupling reaction for 12h. Subsequently, stop the polymerization reaction after cooling down, add 40mL methanol to the flask for precipitation, filter through a Soxhlet extractor and then extract with methanol and n-hexane for 24h; then use chloroform as a solvent to extract until col...

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Abstract

The invention belongs to the field of organic semiconductors, and discloses a phosphinosulfenyl electron transfer material, and a preparation method and an application thereof. The structural formula of the above host material is shown in the specification. In the phosphinosulfenyl electron transfer material, dibenzothiophene sulfone has an excellent electron transfer performance and a large planar rigid structure; and a diphenylphosphinosulfenyl group contains electron-withdrawing P=S, and is a very good electron transfer unit, so the material has high electron mobility and good thermal stability, and can be used in organic electroluminescent devices as an electron transfer layer to improve the luminescence efficiency.

Description

technical field [0001] The invention relates to the field of organic semiconductor materials, in particular to a phosphine-thio-based electron transport material and its preparation method and application. Background technique [0002] Organic electroluminescent devices have excellent characteristics such as lightness, thinness, self-luminescence, low power consumption, no need for light source, no viewing angle limitation, high reaction rate and can be fabricated on flexible substrates. Tomorrow's star. The carrier mobility of traditional electron transport materials is one-thousandth of that of hole transport materials, and the thermal stability is not good. Therefore, it often leads to problems such as poor luminous efficiency or short service life of components. According to relevant literature The charge consumption ratio of electron transport materials is 35.9%, which is second only to the consumption of the light-emitting layer (39.8%). Therefore, the development of ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F9/6553H01L51/54
Inventor 周明杰张振华王平陈吉星
Owner OCEANS KING LIGHTING SCI&TECH CO LTD