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Synthesis of novel organic luminescent material containing triphenylethylene carbazole derivant structure and application thereof

A technology of triphenylene carbazole and luminescent materials, applied in luminescent materials, organic chemistry, chemical instruments and methods, etc., can solve the problems of short life, low glass transition temperature, and low luminous efficiency, and achieve high glass transition temperature , simple synthesis process, high luminous intensity effect

Active Publication Date: 2009-01-14
SUN YAT SEN UNIV
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AI Technical Summary

Problems solved by technology

[0005] However, there are still many problems that need to be solved urgently when OLED enters the practical application, such as the luminous color of the device, working life, fluorescence efficiency, etc.
OLED needs green, red, and blue primary color light-emitting materials. At present, green light materials have reached the practical level requirements, but there is still a big gap between the performance of blue light and red light materials, mainly due to low luminous efficiency, poor stability and short life.
Judging from the reported literature, distyryl derivatives are often used to prepare blue light-emitting materials for OLEDs, but its shortcomings are obvious, such as low luminous efficiency, low glass transition temperature (Tg), and low stability. Difference

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  • Synthesis of novel organic luminescent material containing triphenylethylene carbazole derivant structure and application thereof
  • Synthesis of novel organic luminescent material containing triphenylethylene carbazole derivant structure and application thereof
  • Synthesis of novel organic luminescent material containing triphenylethylene carbazole derivant structure and application thereof

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preparation example Construction

[0020] The synthesis method of above-mentioned luminescent material, comprises the following steps:

[0021] The first step: the synthesis of carbazolyl benzophenone

[0022] The synthesis of carbazolyl benzophenone is obtained by reacting 4-halogenated benzophenone with carbazole and substituent carbazole. In the present invention, 4-fluorobenzophenone is preferably used as the raw material for preparing carbazolyl-containing benzophenone. The preparation process is simple and the yield is high, which is one of the main features of the present invention. For the synthesis of the substituent carbazole starting material, according to the mentioned R 1 , R 2 , R 3 , R 4 The structure of the substituent is synthesized by conventional organic synthesis methods, including Friedel-Crafts alkylation, halogenation, Suzuki reaction, Heck reaction, Wittig reaction, etc.

[0023] Step 2: Conversion of ketone carbonyl to double bond

[0024] Both Wittig and Wittig-Horner methods can...

Embodiment 1

[0030] 9,9'-(4,4'-(2-(4-(1-naphthyl)phenyl)-1,1-vinyl)bis(4,1-phenylene))bis(9H-carba azole) synthesis:

[0031] (1) Synthetic intermediate bis(4-(9H-carbazolyl)phenyl)methanone

[0032] 25g (0.15mol) of carbazole was dissolved in 200mL of DMF, 20g (0.19mol) of potassium tert-butoxide was added under stirring and the temperature was raised to 60°C for 30min, then 14.8g (0.068mol) of 4,4'-difluorobenzophenone was added ), and then heated to 110 ° C for 12 h. 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. 150 mL of acetone was added to the filtrate, dichloromethane and most of the acetone were 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 ob...

Embodiment 2

[0041] Synthesis of 9,9'-(4,4'-(2-(4-terphenyl)-1,1-vinyl)bis(4,1-phenylene))bis(9H-carbazole) Method Referring to Example 1, the boric acid used is 4-biphenylboronic acid. The pure product is an off-white powder with a yield of 62%, λ max em It is 457nm, and Tg is 135°C.

[0042]

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Abstract

The invention relates to a novel luminous material containing a triphenylethylene carbazole derivative structure, which belongs to the technical field of the organic luminous materials. When synthesis is performed, the synthesis of carbazyl diphenyl ketone is performed firstly, and then keto carbonyl is converted into double bond through an organic functional base transition method and then connected with other aromatic groups. The art of the synthetic method of the invention is simple, the purification is easy, the synthesized organic luminous material containing the triphenylethylene carbazole derivative structure has a high thermal stability, a high glass-transition temperature and a strong illumination intensity, and mainly emits blue light, thus the material is very suitable for preparing the material of photogenic layers in organic electroluminescent material devices, in addition, 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 synthesis method of blue light materials and aggregation-induced luminescent materials. Background technique [0002] The research on organic electroluminescent devices, that is, organic light-emitting diodes (OLEDs), began in the 1950s. Due to the lack of functions applied to display elements at that time, this electroluminescence phenomenon has not attracted widespread attention, but can only be used as some basic research on the charge injection, transport and luminescence of organic molecular crystals. [0003] Until 1987, Dr. Liu Qingyun (Ching.W.Tang) and Steve VanSlyke (C.W.Tang, S.A.VanSlyke, Appl.Phys.Lett.1987, 51, 913) of Kodak Company first made a thin-film double-layer organic electroluminescence The device can confine the holes and electrons to recombine near the interface between the electron transport layer and the hole transport layer, th...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C09K11/06C07D403/10
Inventor 池振国杨志涌于涛陈美娜张锡奇王程程许炳佳刘四委张艺许家瑞
Owner SUN YAT SEN UNIV
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