Phosphine sulfur group electron transport material, 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 thermal stability, poor luminous efficiency, and short service life of components, and achieve novel structure, High electroluminescence efficiency, high electron mobility effect

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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  • Phosphine sulfur group electron transport material, preparation method and application thereof
  • Phosphine sulfur group electron transport material, preparation method and application thereof
  • Phosphine sulfur group electron transport material, 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 3,6-diphenyl-2,5-bis(4-(diphenylphosphinethio)phenyl)benzodifuran are as follows:

[0030]

[0031] Under the protection of argon, 3,6-diphenyl-2,5-dibromobenzodifuran (94 mg, 0.2 mmol), diphenyl (4-pinacol borate phenyl) phosphine sulfur ( 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 added bistriphenyl Phosphine palladium dichloride (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. The...

Embodiment 2

[0034] The preparation steps of the phosphinethio-based electron transport material of this example, namely 3,6-diphenyl-2,5-bis(4-(diphenylphosphinethio)phenyl)benzodifuran are as follows:

[0035]

[0036] Under the protection of a mixed gas of nitrogen and argon, 3,6-diphenyl-2,5-dibromobenzodifuran (140 mg, 0.3 mmol), diphenyl (4-pinacol borate phenyl) Phosphine sulfur (252mg, 0.6mmol) and 15mL tetrahydrofuran were added into a 50mL two-necked bottle, and after fully dissolved, a mixture of nitrogen and argon was introduced to exhaust the air for about 20 minutes, and tetrakistriphenylphosphine palladium (4mg, 0.003mmol ) into it, fully dissolved and then added sodium bicarbonate (3mL, 2mol / L) solution. 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 methanol was added to...

Embodiment 3

[0038] The preparation steps of the phosphinethio-based electron transport material of this example, namely 3,6-diphenyl-2,5-bis(4-(diphenylphosphinethio)phenyl)benzodifuran are as follows:

[0039]

[0040] Under nitrogen protection, 3,6-diphenyl-2,5-dibromobenzodifuran (140mg, 0.3mmol), diphenyl(4-pinacol borate phenyl)phosphine sulfur (277mg, 0.66mmol), palladium acetate (3.5mg, 0.015mmol) and three (o-methoxyphenyl) phosphine (21mg, 0.06mmol) were added to the flask containing 12mL of N,N-dimethylformamide, fully After dissolving, add potassium carbonate (3mL, 2mol / L) solution, 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 extract until colorless, ...

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Abstract

Belonging to the field of organic semiconductors, the invention discloses a phosphine sulfur group electron transport material, a preparation method and application thereof. The structural formula of the host material is shown as the specification. In the phosphine sulfur group electron transport material provided by the invention, dibenzofuran has a large plane rigid structure; and the diphenyl diphenyl phosphine sulfur group contains electron-withdrawing P=S, and is a good electron transport unit. Thus, the material has high electron mobility and good thermal stability, and can be used as an electron transport layer in organic electroluminescent devices to improve the luminous 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): C07F9/6561H01L51/54
Inventor 周明杰张振华王平陈吉星
Owner OCEANS KING LIGHTING SCI&TECH CO LTD
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