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Phosphinosulfenyl electron transfer material, preparation method thereof, and organic electroluminescent device

An electron transport material, phosphine thio-based technology, applied in electric solid devices, organic chemistry, electrical components, etc., can solve the problems of poor thermal stability, poor luminous efficiency, and short component life, and achieve novel structure, The effect of high electroluminescence efficiency 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

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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, preparation method thereof, and organic electroluminescent device
  • Phosphinosulfenyl electron transfer material, preparation method thereof, and organic electroluminescent device
  • Phosphinosulfenyl electron transfer material, preparation method thereof, and organic electroluminescent device

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0029] The phosphinethio-based electron transport material of this embodiment, namely 2,7-bis(4-(diphenylphosphinethio)phenyl)-4,9-diphenylpyrido[2,3-g]quinoline, Its preparation steps are as follows:

[0030]

[0031] Under the protection of argon, 2,7-dibromo-4,9-diphenylpyrido[2,3-g]quinoline (98 mg, 0.2 mmol), diphenyl (4-pinacol boronic acid Esterphenyl)phosphine sulfur (168mg, 0.4mmol) was added to a flask filled with 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 added bistriphenylphosphinepalladium dichloride (5.6mg, 0.008mmol); the flask was heated to 120°C for Suzuki coupling reaction for 24h. 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...

Embodiment 2

[0034] The phosphinethio-based electron transport material of this embodiment, namely 2,7-bis(4-(diphenylphosphinethio)phenyl)-4,9-diphenylpyrido[2,3-g]quinoline, Its preparation steps are as follows:

[0035]

[0036] Under the protection of mixed gas of nitrogen and argon, 2,7-dibromo-4,9-diphenylpyrido[2,3-g]quinoline (167mg, 0.3mmol), diphenyl (4-pina Alcohol borate phenyl)phosphine sulfur (252mg, 0.6mmol) and 15mL tetrahydrofuran were added into a 50mL two-necked bottle, and after fully dissolving, a mixture of nitrogen and argon was introduced to exhaust the air for about 20 minutes, and then tetratriphenyl Phosphine palladium (4mg, 0.003mmol) was added to it, and after fully dissolved, sodium bicarbonate (3mL, 2mol / L) solution was added. 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 d...

Embodiment 3

[0038] The phosphinethio-based electron transport material of this embodiment, namely 2,7-bis(4-(diphenylphosphinethio)phenyl)-4,9-diphenylpyrido[2,3-g]quinoline, Its preparation steps are as follows:

[0039]

[0040] Under nitrogen protection, 2,7-dibromo-4,9-diphenylpyrido[2,3-g]quinoline (167mg, 0.3mmol), diphenyl(4-pinacol borate benzene Base) phosphine sulfur (277mg, 0.66mmol), palladium acetate (3.5mg, 0.015mmol) and tris (o-methoxyphenyl) phosphine (21mg, 0.06mmol) were added to a 12mL N,N-dimethyl In the formamide flask, add potassium carbonate (3mL, 2mol / L) solution after fully dissolving, then blow nitrogen into the flask and exhaust the air for about 30min; heat the flask 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 extrac...

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Abstract

The invention belongs to the field of organic semiconductors, and discloses a phosphinosulfenyl electron transfer material, a preparation method and an organic electroluminescent device. The structural formula of the above host material is shown in the specification. In the phosphinosulfenyl electron transfer material, diphenylphosphinoquinoline has 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 the organic electroluminescent device 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 a preparation method thereof. The invention also relates to an organic electroluminescent device using a phosphine-thio-based electron transport material as the material of the electron transport layer 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 cons...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F9/6561H01L51/54
Inventor 周明杰张振华王平陈吉星
Owner OCEANS KING LIGHTING SCI&TECH CO LTD
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