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Phosphine-containing benzophenone organic light-emitting material, synthesis method and applications thereof

A technology of benzophenones and luminescent materials, applied in luminescent materials, organic chemistry, chemical instruments and methods, etc., can solve the problems of high hole transport efficiency, achieve high fluorescence quantum efficiency, simplify the structure and preparation process, and achieve high electronic efficiency. The effect of transmission performance

Active Publication Date: 2017-04-19
SUN YAT SEN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, for most organic electroluminescent materials, due to the large conjugation plane and some hole transport groups (carbazole, aniline derivatives) in the structure, the hole transport efficiency is much higher than the electron transport efficiency.

Method used

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  • Phosphine-containing benzophenone organic light-emitting material, synthesis method and applications thereof
  • Phosphine-containing benzophenone organic light-emitting material, synthesis method and applications thereof
  • Phosphine-containing benzophenone organic light-emitting material, synthesis method and applications thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0049] (1) Synthesis of intermediate [4-fluoro-4'-iodobenzophenone]

[0050]

[0051] Add 4-iodobenzoyl chloride (5.00g, 18.8mmol) into a 250mL dry three-necked flask, then add fluorobenzene (5.41g, 56.3mmol), stir, add anhydrous aluminum chloride (3.88g, 28.2mmol), Raise the temperature to 40-50°C and react for 5-6 hours. After the reaction, add 50ml of dichloromethane into the three-neck flask to dissolve, slowly add dilute hydrochloric acid, and stir until there is no precipitation. Then the reaction solution was poured into a separatory funnel, extracted 3 times with dichloromethane, and washed 2-3 times with dilute hydrochloric acid until the aqueous layer became colorless. The organic layer was dried over anhydrous sodium sulfate, filtered, and the filtrate was spin-dried in a rotary evaporator to obtain 5.06 g of a yellow-white solid. Yield 83%.

[0052] (2) Synthesis of intermediate [4-iodo-4'-carbazolylbenzophenone]

[0053]

[0054] Add carbazole (1.54g, 9....

Embodiment 2

[0059]

[0060] The product of Example 1 (0.40 g, 0.75 mmol) was added into a round bottom flask, and dissolved in 20 ml of tetrahydrofuran. 6 mL of hydrogen peroxide aqueous solution (30%) was added, and after stirring for 5 hours, 50 mL of dichloromethane and 50 mL of water were added to the reaction liquid, followed by liquid separation. The dichloromethane layer was spin-dried with a rotary evaporator to obtain a white powder. The white powder was recrystallized from dichloromethane / n-hexane to obtain 0.35 g of a white solid with a yield of 85%.

[0061] The fluorescence emission spectra of the toluene solution of the product of this embodiment before and after oxygenation are as follows: image 3 As shown, it is shown that it has a specific response to oxygen and the like.

Embodiment 3

[0063] (1) Synthesis of intermediate [4-iodo-4'-phenothiazinylbenzophenone]

[0064]

[0065] Referring to step (2) of Example 1, 4-iodo-4'-phenothiazinylbenzophenone was synthesized by using phenothiazine instead of carbazole. (49% yield)

[0066] (2) Synthesis of the target product

[0067]

[0068] With reference to step (3) of Example 1, 4-iodo-4'-phenothiazinylbenzophenone was used to replace 4-iodo-4'-carbazolylbenzophenone to synthesize 4-diphenylphosphine-4'- Phenothiazinylbenzophenone. (Yield rate is 63%)

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Abstract

The invention discloses a phosphine-containing benzophenone organic light-emitting material, a synthesis method and applications thereof, wherein the molecular general formula is Ar-Ar'-R, Ar is a phosphine-containing functional group, Ar' is benzophenone, and R is alkane, halogen, aromatic ring or aromatic heterocyclic substituent, and the like. According to the present invention, the synthesis method has advantages of simple process and easy purification, and the synthesized light-emitting material has good electron transmission performance and high fluorescence quantum efficiency, is suitable for preparing the light-emitting layer or electron transmission layer in organic electroluminescent devices, and can further be adopted as the light-emitting material and the electron transmission material in OLEDs, wherein the two layers in the classic OLEDs structure are integrated into one layer so as to simplify the OLEDs device structure and the preparation process; and the light-emitting material of the present invention specifically responds to oxygen, metal ions and the like, and is suitable for use in chemical detection, biological detection, biological imaging, anti-counterfeiting, and other fields.

Description

technical field [0001] The invention relates to the technical field of organic luminescent materials, in particular to the synthesis of novel organic luminescent materials containing phosphine and their application in organic electroluminescent material devices as light-emitting layer or electron transport layer materials. In addition, the novel organic luminescent material containing phosphine in the present invention also has specific responses to oxygen, metal ions, etc., and is suitable for fields such as chemical and biological detection, biological imaging, and anti-counterfeiting. Background technique [0002] Organic electroluminescent materials have great application potential in flat panel display, solid-state lighting and other fields, and have received extensive attention and attention from the scientific and technological and industrial circles in recent years. (Yllen K M, Scherf U. Organic Light-Emitting Devices: Synthesis, Properties and Applications. Weinheim...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F9/572C07F9/6547C07F9/50C09K11/06H01L51/54
CPCC09K11/06C07F9/5022C07F9/5072C07F9/5728C07F9/6547C09K2211/1037C09K2211/1014C09K2211/1007C09K2211/1029H10K85/657H10K85/6572
Inventor 池振国谢宗良于涛黄秋忆欧德培王乐宇毛竹王家强杨志涌张艺刘四委许家瑞
Owner SUN YAT SEN UNIV
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