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Synthesis of novel organic luminescent material containing carbazolyl toluylene derivant structure and application thereof

A technology of carbazolyl stilbene and light-emitting materials, which is applied in the fields of light-emitting materials, organic chemistry, and material excitation analysis. It can solve the problems of poor OLED stability, low luminous efficiency and intensity, and short life, and achieve high glass transition. Effects of temperature, ease of purification, and high thermal stability

Active Publication Date: 2009-01-14
SUN YAT SEN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Obviously, low Tg is one of the main reasons for the poor stability and short life of OLEDs; on the other hand, due to the existence of aggregation quenching, the luminous efficiency and intensity of most luminescent materials in solid state are significantly lower than those in solution. , and the luminescent material is used in solid state in OLED, so overcoming aggregation quenching is also the main research direction at present.

Method used

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  • Synthesis of novel organic luminescent material containing carbazolyl toluylene derivant structure and application thereof
  • Synthesis of novel organic luminescent material containing carbazolyl toluylene derivant structure and application thereof
  • Synthesis of novel organic luminescent material containing carbazolyl toluylene derivant structure and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0016] Synthesis of 4,4'-bis(2,2-bis(4-(9H-carbazolyl)phenyl)vinyl)biphenyl:

[0017] (1) Synthetic intermediate bis(4-(9H-carbazolyl)phenyl)methanone

[0018] Dissolve 25g (0.15mol) of carbazole in 200mL of DMF, add 20g (0.19mol) of potassium tert-butoxide under stirring and raise the temperature to 60°C for 30min, then add 14.8g (0.068mol) of difluorobenzophenone, and then raise the temperature to 110 ℃ reaction 12h. Stop the reaction, pour into 500mL water for precipitation after cooling, filter with suction, and wash with water several times. Dissolve the solid in 150mL of dichloromethane to form a solution, add an appropriate amount of anhydrous sodium sulfate to dry, and filter. Add 150mL of acetone to the filtrate, dichloromethane and most of the acetone are evaporated by a rotary evaporator to obtain a precipitate, filtered by suction, washed 3 times with a small amount of acetone, and vacuum-dried to obtain 32g of light yellow powder with a yield of 92%.

[0019] ...

Embodiment 2

[0024] The synthetic method of 2,5-bis(4-(2,2-bis(4-(9H-carbazolyl)phenyl)vinyl)phenyl)-1,3,4-oxadiazole) refers to the example 1, the phosphonate ylide reagent used is tetraethyl (4,4'-(1,3,4-oxadiazole-2,5-diyl) bis(4,1-phenylene)) bis(sub- Methyl) bisphosphonate. The yield was 65%. lambda max em 471nm, Φ FL is 2.5%, Tg is 192°C, and Td is 495°C.

[0025]

Embodiment 3

[0027] Synthesis of 4,4'-bis(2,2-bis(4-(3,6-di-tert-butyl-9H-carbazolyl)phenyl)vinyl)biphenyl:

[0028] (1) Synthesis of intermediate bis(4-(3,6-di-tert-butyl-9H-carbazolyl)phenyl)methanone

[0029] 4.2 g (0.015 mol) of 3,6-di-tert-butyl-9H-carbazole was dissolved in 50 mL of DMF, 2 g (0.019 mol) of potassium tert-butoxide was added under stirring and the temperature was raised to 60 ° C for 30 min, then difluoro di 1.5 g (0.0068 mol) of benzophenone was heated to 110° C. for 12 hours. Stop the reaction, pour it into 500mL water after cooling to produce a precipitate, filter it with suction, and wash it with water several times. Dissolve the solid in 150mL of dichloromethane to form a solution, add an appropriate amount of anhydrous sodium sulfate to dry, and filter. Add 150mL of acetone to the filtrate, dichloromethane and most of the acetone are evaporated by a rotary evaporator to obtain a precipitate, filtered by suction, washed 3 times with a small amount of acetone, an...

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Abstract

The invention relates to novel luminous material containing a carbazyl stilbene derivative structure, which belongs to the technical field of the organic luminous materials. When the synthesis is performed, two carbazyl diphenyl ketones (2) are connected by an aromatic compound containing two ylide groups; or the carbazyl diphenyl ketones are changed into an intermediate body (3) or an intermediate body (4) firstly, and then the carbazyl stilbene is coupled by a crossed coupling method. The art of the synthetic method provided by the invention is simple, the purification is easy, the synthesized organic luminous material containing the carbazyl stilbene derivative structure has a high thermal stability, a high glass-transition temperature and a strong illumination intensity, the material is suitable for preparing the material of photogenic layers in organic electroluminescent material devices, the luminous material with aggregation-induced emission effect can be serviced as stimuli-response functional material to be applied to chemical / biochemical sensors.

Description

technical field [0001] The invention belongs to the technical field of organic luminescent materials, in particular to a luminescent material with a high glass transition temperature and a synthesis method of an aggregation-induced luminescent material. Background technique [0002] A thin-film display based on an organic light-emitting diode (OLED) device, which is thinner, lighter, actively luminous, high brightness, rich in color, high in efficiency, fast in response, high in definition, wide in viewing angle, low in power consumption, low in cost, and available Curl, low temperature resistance, excellent shock resistance and many other advantages are known as "dream displays" (Wen Shangsheng, Li Aiyuan, Wen Fei, etc., Research Progress in Flexible Organic Electroluminescent Devices. Journal of Quantum Electronics, 2007, 24 (6) :664). It is now recognized as a new generation of graphics and image display devices after liquid crystal display LCD and plasma display PDP. It...

Claims

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Application Information

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IPC IPC(8): C09K11/06C07D209/82G01N21/66H05B33/14
Inventor 池振国杨志涌张锡奇于涛陈美娜许炳佳王程程周林刘四委张艺许家瑞
Owner SUN YAT SEN UNIV
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