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Siloxane dyestuff containing DCM structure and synthesis method thereof

A synthesis method and technology of siloxane, applied in the directions of organic dyes, azo dyes, organic silicon compounds, etc., can solve the problems such as hindering the practical application of DCM dyes, decreasing luminous intensity and luminous efficiency, unable to obtain red luminescence, etc. The effect of reduced quenching effect, high yield, and high fluorescence efficiency

Inactive Publication Date: 2011-06-01
ZHEJIANG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, due to the strong interaction between DCM dye molecules, the concentration quenching phenomenon is very significant
As the doping concentration of DCM dyes increases, the number of non-radiative transition centers in the luminescent material increases, resulting in a decrease in the probability of radiative transitions, and a decrease in luminous intensity and luminous efficiency.
Moreover, when the DCM dye doping concentration is too low, the luminescent color of the device is yellowish, and true red luminescence cannot be obtained, which seriously hinders the practical application of DCM dyes.

Method used

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  • Siloxane dyestuff containing DCM structure and synthesis method thereof
  • Siloxane dyestuff containing DCM structure and synthesis method thereof
  • Siloxane dyestuff containing DCM structure and synthesis method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0026] R in the general structural formula of siloxane dyes containing DCM structure 1 is methylene, R 2 For methyl.

[0027] The synthetic route of the siloxane dye containing DCM structure is as follows:

[0028]

[0029] The synthesis method is:

[0030] 1) Synthesis of aniline aldehyde intermediate

[0031] Dissolve 1 mol of methylaminoethanol and 1 mol of p-fluorobenzaldehyde in 200 mL of dimethyl sulfoxide, add 2 mol of potassium carbonate and 1 mL of methyl trioctyl ammonium chloride to the solution, and react at 80°C for 3 days. After the reaction, cool to room temperature, pour the reaction solution into ice water, stir and let it stand to precipitate a precipitate, filter and wash with water. The resulting precipitate was purified by silica gel column chromatography to obtain aniline aldehyde intermediate 4-[4-(N-methyl-N-hydroxyethyl)amino]benzaldehyde.

[0032] 2) Synthesis of DCM dyes

[0033] In a three-necked flask, add 1mol of 4-[4-(N-methyl-N-hydroxye...

Embodiment 2

[0040] R in the general structural formula of siloxane dyes containing DCM structure 1 is phenyl, R 2 For phenyl.

[0041] The synthetic route of the siloxane dye containing DCM structure is as follows:

[0042]

[0043] The synthesis method is:

[0044] 1) Synthesis of aniline aldehyde intermediate

[0045] Under nitrogen protection, add 1mol of triphenylamine and 0.5L of N,N-dimethylformamide into a three-necked flask and cool to 0°C, add 2mol of phosphorus oxychloride dropwise and react at 70°C for 15 hours . Then the reactant was poured into ice water, the pH value was adjusted to neutral with sodium hydroxide, and the crude product was obtained by rotary evaporation after extraction with dichloromethane. Then the crude product was dissolved in tetrahydrofuran, and slowly dropped into 100 mL of ethanol solution of sodium borohydride with a concentration of 1.6 g / mL. React at room temperature, and adjust the pH value to neutral with dilute hydrochloric acid at the ...

Embodiment 3

[0052] R in the general structural formula of siloxane dyes containing DCM structure 1 is methylene, R 2 For phenyl.

[0053] The synthetic method of this siloxane dye containing DCM structure is:

[0054] 1) Synthesis of aniline aldehyde intermediate

[0055] Dissolve 1 mol of phenylaminoethanol and 2 mol of p-fluorobenzaldehyde in 500 mL of dimethyl sulfoxide, add 4 mol of potassium carbonate and 2 mL of methyl trioctyl ammonium chloride to the solution, and react at 120 ° C for 2 days. After the reaction, cool to room temperature, pour the reaction solution into ice water, stir and let it stand to precipitate a precipitate, filter and wash with water. The resulting precipitate was purified by silica gel column chromatography to obtain aniline aldehyde intermediate 4-[4-(N-phenyl-N-hydroxyethyl)amino]benzaldehyde.

[0056] 2) Synthesis of DCM dyes

[0057] In a three-necked flask, add 1mol of 4-[4-(N-phenyl-N-hydroxyethyl)amino]benzaldehyde and 2mol of 4-dicyanomethylen...

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Abstract

The invention discloses a siloxane dye which contains the DCM structure and has the structural general formula as shown in 1). In the formula, R1 is a methylene or a phenyl; R2 is an ethyl or a phenyl. In the synthetic method of the dye, an aniline aldehyde intermediate is synthesized firstly; 4-dicyan methylene-2, 6-dimethyl-4H-pyrane reacts with the aniline aldehyde intermediate through Knoevenagel, thus getting molecules of DCM dye, and then the addition reaction of the DCM dye and a silane-coupling agent is carried out. The synthetic process is simple and the yield is high. Compared with the conventional DCM dye, the siloxane dye containing the DCM structure has high fluorescence efficiency, greatly reduced concentration quenching effect, and good dissolubility, and can get higher dosage concentration. The fluorescence emission peak of the siloxane dye is arranged in the red visible light area. The siloxane dye containing the DCM structure is promising to be practically applied in the fields of organic electroluminescent display, lasers and so on as a novel red fluorescent dye.

Description

technical field [0001] The invention relates to a siloxane dye containing a DCM structure and a synthesis method thereof. Background technique [0002] With the rapid development of science and technology and the continuous improvement of human living standards, people have higher and higher requirements for high-density and high-definition display technology. Because organic / polymer electroluminescent devices can realize low power consumption and high-performance large-area flat-panel displays, organic electroluminescent displays, as a new type of flat-panel display technology, have attracted widespread attention. In the past ten years, people have carried out a lot of research on organic light-emitting materials and their photoelectric properties, and the brightness and stability of display devices have also been greatly improved. At present, commercialized organic displays have successively appeared on the market. product. Doping high-efficiency fluorescent dyes into or...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C09B57/00C07F7/02C09K11/06H05B33/14
Inventor 钱国栋崔元靖郁建灿任华森王智宇樊先平王民权
Owner ZHEJIANG UNIV
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