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Gathering induced luminescence material containing triphenyl thylene structure, synthesis method and application thereof

A technology of aggregation-induced luminescence and triphenylethylene, which is applied in the direction of luminescent materials, styrene-based dyes, and material excitation analysis, can solve problems such as low glass transition temperature, limited compounds, and difficult molecular design, and achieve high luminous intensity and purification Easy, high glass transition temperature effect

Active Publication Date: 2010-03-03
SUN YAT SEN UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

But so far, very limited compounds with AIE effects have been developed, and many of these compounds are still based on silole derivatives
Throughout the reported literature, silole derivatives have obvious disadvantages: low glass transition temperature; molecular design is more difficult

Method used

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  • Gathering induced luminescence material containing triphenyl thylene structure, synthesis method and application thereof
  • Gathering induced luminescence material containing triphenyl thylene structure, synthesis method and application thereof
  • Gathering induced luminescence material containing triphenyl thylene structure, synthesis method and application thereof

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preparation example Construction

[0017] The synthesis method of above-mentioned luminescent material, comprises the following steps:

[0018] Step 1: Synthesis of Benzophenone Derivatives

[0019] The synthesis of benzophenone derivatives is obtained by reacting 4,4'-dihalogenated benzophenone and 4,4'-methylbenzophenone with other aromatic compounds. The present invention preferably adopts 4,4'-difluorobenzophenone, 4,4'-dibromobenzophenone and 4,4'-methylbenzophenone as raw materials for preparing benzophenone derivatives, and the preparation process is simple, High yield is one of the main features of the present invention. For the synthesis of substituents, according to the mentioned R 4 , R 5 , R 6 , R 7 , R 8 The structure of the substituent is synthesized by conventional organic synthesis methods, including Friedel-Crafts alkylation, amine alkylation, halogenation, Suzuki reaction, Heck reaction, Wittig reaction, etc.

[0020] Step 2: Conversion of ketone carbonyl to double bond

[0021] Method...

Embodiment 1

[0028] Synthesis of p-naphthalene triphenylethylene:

[0029] (1) Synthetic intermediate p-bromotriphenylethylene

[0030] 4,4'-dibromobenzophenone (34.0g, 0.1mol), diethyl 4-bromobenzylidene phosphonate (30.7g, 0.1mol) were added in the there-necked flask, and 200mL of dry tetrahydrofuran was added, and Potassium tert-butoxide (11.2 g, 0.1 mol) was added under the protection of argon, stirred at room temperature for 12 h, and the reaction solution was poured into 500 mL of ethanol for precipitation. Suction filtration, washing with ethanol three times, and drying to obtain 46.8 g of white powder with a yield of 95%.

[0031]

[0032] (2) Synthesis of p-naphthalene triphenylethylene:

[0033] p-Bromotriphenylethylene (0.83g, 0.0017mol), 2-naphthaleneboronic acid (0.85g, 0.005mol) were added to the three-necked flask, and 20mL of toluene, 2M K 2 CO 3 Aqueous solution 5mL, TBAB 1g, after stirring and argon flow for 30min, add 0.01g Pd(PPh 3 ) 4 , The oil bath was heated...

Embodiment 2

[0036] The synthesis method of p-benzothiophene triphenylethylene refers to Example 1, and the boric acid used is 4-dibenzothiophene boronic acid. The pure product was an off-white powder with a yield of 67%.

[0037]

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Abstract

The invention belongs to the technical field of organic luminescence materials. The gathering luminescence material of the invention contains a triphenyl thylene structure, ketone carbonyl is converted into double bonds by substituent phenyl ketone through a Wittig reaction or a Wittig-Horner reaction during synthesis, and the triphenyl thylene structure is formed and then is connected with otheraromatic base groups. The synthesis method has simple technique and easy purification, and the synthesized organic luminescence material containing the triphenyl thylene structure not only has obvious gathering induced luminescence performance, high thermal stability, high vitrifaction transformation temperature and high luminescence intensity, but also is suitable for preparing a luminescence layer material in an organic electroluminescence material component; by introducing proper base groups, and the organic luminescence material also can be used as a fluorescent probe and organic solar battery sensitizing dyestuff.

Description

technical field [0001] The invention belongs to the technical field of organic light-emitting materials, in particular to a synthesis method of aggregation-induced light-emitting materials. Background technique [0002] Organic light-emitting diodes (OLEDs) and other organic light-emitting devices have been highly valued by the scientific and industrial circles in recent years due to their huge potential applications in flexible displays, and are one of the current research and development hotspots (Yllen K M, ScherfU.Organic Light-Emitting Devices: Synthesis, Properties and Applications. Weinheim: Wiley-VCH, 2006). [0003] However, the current organic light-emitting device technology has encountered a bottleneck problem in the development process, that is, the fluorescence efficiency and service life of the light-emitting device have not yet met the practical requirements. For example, the expected OLED display has not yet entered industrial-scale applications. There are ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C09K11/06H01L51/54H01L51/56G01N21/64C09B23/14H01G9/20H01M14/00H01L51/46H01L51/48C07C1/32C07C15/58C07C15/52C07D333/76C07C211/54C07D209/86
CPCY02E10/549Y02P70/50
Inventor 池振国许炳佳黎小芳陈美娜杨志涌王程程刘四委张艺许家瑞
Owner SUN YAT SEN UNIV
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