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Aggregation-induced emission material with long alkyl chain toluylene carbazole structure, synthesizing method and application thereof

An aggregation-induced luminescence, stilbene carbazole-based technology, applied in luminescent materials, chemical instruments and methods, organic chemistry, etc., can solve the problem of fluorescent efficiency and lifespan of luminescent materials with service life, which has not been well solved, and OLED devices. The fluorescence efficiency and service life cannot meet the practical requirements, and the OLED display cannot enter the industrial scale application, etc., to achieve the effects of good solubility, easy purification, and good luminous characteristics

Inactive Publication Date: 2013-07-10
SOUTH CHINA NORMAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] However, at present, OLED technology has encountered a bottleneck problem in the development process, that is, the fluorescence efficiency and service life of OLED devices have not yet met the practical requirements, resulting in the long-awaited OLED display being unable to enter industrial-scale applications.
The main reason for affecting the fluorescence efficiency and service life of OLED devices is that the fluorescence efficiency and life of luminescent materials have not been well resolved.
Dilute solutions of most luminescent materials have high fluorescence quantum yields, but in their solid state they become weakly or not at all fluorescent due to aggregation-induced fluorescence quenching

Method used

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  • Aggregation-induced emission material with long alkyl chain toluylene carbazole structure, synthesizing method and application thereof
  • Aggregation-induced emission material with long alkyl chain toluylene carbazole structure, synthesizing method and application thereof
  • Aggregation-induced emission material with long alkyl chain toluylene carbazole structure, synthesizing method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0028] Synthesis of 4,4'-bis(2,2'-bis(4-(6-(9H-carbazolyl)hexyloxy)phenyl)vinyl)biphenyl

[0029] (1) Synthesis of intermediate compound N-6-bromohexyl-9H-carbazole

[0030] In a 100ml three-necked flask equipped with a reflux device and protected by nitrogen, 3g (0.018mol) carbazole, 35ml acetone, 4.3g KOH, and 18ml (0.115mol) 1,6-dibromohexane were sequentially added. Stir at room temperature for 24 h, then pour into water, extract 3 times with dichloromethane, wash the organic phase with water 4 times, wash with anhydrous Mg 2 SO 4 After drying for 3 h, the solvent was distilled under reduced pressure. The remaining solid was separated by column chromatography (SiO 2 ; Eluent: dichloromethane / n-hexane=1:6, v / v), to obtain a white solid product.

[0031]

[0032] (2) Synthetic intermediate bis(4-(6-(9H-carbazolyl)hexyloxy)phenyl)methanone

[0033] In a 100ml three-neck flask equipped with a reflux device and protected by argon, add 1g (3mmol) compound N-6-bromohexyl-...

Embodiment 2

[0043] Synthesis of 4,4'-bis(2,2'-bis(4-(12-(9H-carbazolyl)dodecyloxy)phenyl)vinyl)biphenyl

[0044] (1) Synthesis of intermediate N-12-bromododecyl-9H-carbazole

[0045] In a 100ml three-necked flask equipped with a reflux device and protected by nitrogen, 3g (0.018mol) carbazole, 35ml acetone, 4.3g KOH, and 38g (0.115mol) 1,12-dibromododecane were sequentially added. Stir at room temperature for 24 h, then pour into water, extract 3 times with dichloromethane, wash the organic phase with water 4 times, wash with anhydrous Mg 2 SO 4 After drying for 3h, it was distilled under reduced pressure. The remaining solid was separated by column chromatography (SiO 2 ; Eluent: dichloromethane / n-hexane=1:6, v / v), to obtain a white product.

[0046]

[0047] (2) Synthetic intermediate bis(4-(12-(9H-carbazolyl)dodecyloxy)phenyl)methanone

[0048] In a 100ml three-necked flask equipped with a reflux device and protected by argon, 1.7g (3mmol) N-12-bromododecyl-9H-carbazole, 20ml D...

Embodiment 3

[0054] Synthesis of 4,4'-bis(2,2'-bis(4-(4-(9H-carbazolyl)butoxy)phenyl)vinyl)biphenyl

[0055] (1) Synthesis of intermediate compound N-4-bromobutyl-9H-carbazole

[0056] In a 100ml three-necked flask equipped with a reflux device and protected by nitrogen, add 3g (0.018mol) carbazole, 35ml acetone, 0.02g TBAB, 4.3g KOH, and 25g (0.115mol) 1,4-dibromobutane in sequence. Stir at room temperature for 24 h, then pour into water, extract 3 times with dichloromethane, wash the organic phase with water 4 times, wash with anhydrous Mg 2 SO 4 After drying for 3 h, the solvent was distilled under reduced pressure with a rotary evaporator. The remaining solid was separated by column chromatography (SiO 2 ; Eluent: dichloromethane / n-hexane=1:6, v / v) to obtain a white product.

[0057]

[0058] (2) Synthesis of bis(4-(4-(9H-carbazolyl)butoxy)phenyl)methanone

[0059] In a 100ml three-necked flask equipped with a reflux device and protected by argon, add 0.9g (3mmol) N-4-bromobuty...

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Abstract

The invention belongs to the technical field of an organic light emission material which is of a carbazole based toluylene derivative structure with a long alkyl chain. The carbon-carbon double bond in the light emission material is formed by synthesizing through a Wittig-Horner reaction. According to the synthesizing method of the light emission material provided by the invention, the synthesizing process is simple, the purification is easy, the synthesized organic light emission material with the carbazole based toluylene derivative structure with a long alkyl chain has the characteristic of high light emission strength, in particular better light emission property in an aggregation state; the light emission material has an excellent dissolubility due to the long alkyl chain structure, can be easily filmed; and the light emission material has aggregation induced emission and gas-sensitivity effects, is suitable for preparing an emission layer material in organic electroluminescence devices, and can be used as an impulse response functional material applied to chemical / biological sensors.

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] Since the advent of organic electroluminescent devices (OLEDs), organic electroluminescent materials have been highly valued by the scientific and industrial circles for their high luminous brightness and luminous efficiency, rich colors, and easy processing of materials. [0003] However, at present, OLED technology has encountered a bottleneck problem in the development process, that is, the fluorescence efficiency and service life of OLED devices have not yet met the practical requirements, resulting in the long-awaited OLED display being unable to enter industrial-scale applications. The main reason for affecting the fluorescence efficiency and service life of OLED devices is that the fluorescence efficiency and life of luminescent materials have not been...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C09K11/06C07D209/86H01L51/54
Inventor 石光何文刘聪
Owner SOUTH CHINA NORMAL UNIVERSITY
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