Tetraphenylethylene-phenanthroimidazole derivative and crystal, preparation method and application thereof

A technology of phenanthroimidazole and tetraphenylethylene, applied in the field of luminescent materials, can solve problems such as poor thermal stability, low luminous intensity, and concentration quenching

Inactive Publication Date: 2019-04-16
GUANGDONG UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] The invention provides a tetraphenylethylene-phenanthroimidazole derivative and its crystal, preparation method and application, which solves the technical problems of low luminous intensity, easy concentration quenching and poor thermal stability of existing luminescent materials

Method used

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  • Tetraphenylethylene-phenanthroimidazole derivative and crystal, preparation method and application thereof
  • Tetraphenylethylene-phenanthroimidazole derivative and crystal, preparation method and application thereof
  • Tetraphenylethylene-phenanthroimidazole derivative and crystal, preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0082] (1) Preparation of formula (II) compound

[0083] Weigh 1.82g 4,4-dihydroxy-benzophenone, 6.5g 4-bromo-benzophenone and 6.53g zinc powder in a 250mL round-bottomed flask, add 100mL of tetrahydrofuran to dissolve to obtain a mixed solution; Under the protection of nitrogen, perform magnetic stirring, cool to 0°C, inject 5.6ml of titanium tetrachloride, stir at -10°C for 30min, heat to reflux at 90°C for 20h, cool to room temperature, and add 60ml of dilute hydrochloric acid to quench the reaction. After purification by column chromatography, the eluent was n-hexane / ethyl acetate, and 3.05 g of the compound of formula (II) was isolated as a white solid.

[0084] The reaction equation is as follows:

[0085]

[0086] (2) Preparation of formula (Ⅲ-1) compound

[0087] Weigh 1.2g of (II) compound, 1.54g of methyl iodide and 1.9g of potassium carbonate in a 100ml round bottom flask, add 50ml of N,N dimethylformamide, and carry out magnetic stirring under the protection o...

Embodiment 2

[0099] (1) The preparation of the compound of formula (II) is the same as in Example 1

[0100] (2) Preparation of formula (Ⅲ-2) compound

[0101] Weigh 1.2g of the compound of formula (II), 1.54g of n-bromobutane and 1.9g of potassium carbonate in a 100ml round bottom flask, add 50ml of N,N dimethylformamide, carry out magnetic stirring under the protection of nitrogen, and heat to temperature 70°C, reacted for 15 hours, and cooled to room temperature. After purification by column chromatography, the eluent was n-hexane / dichloromethane, and 1.08 g of the compound of formula (III-2) was isolated as a yellow oil.

[0102] The reaction equation is as follows:

[0103]

[0104] (3) preparation of formula (Ⅴ-2) compound

[0105] Weigh 0.94g formula (Ⅲ-2) compound, 0.5g formula (Ⅳ-1) compound 4-formylphenylboronic acid, 1.52g potassium carbonate and 0.12g tetrakistriphenylphosphine palladium in a 100ml round bottom flask, add 40ml Tetrahydrofuran and 10ml of water were magne...

Embodiment 3

[0113] (1) The preparation of the compound of formula (II) is the same as in Example 1

[0114] (2) Preparation of formula (Ⅲ-3) compound

[0115] Weigh 1.2g of the compound of formula (II), 1.54g of n-bromohexane and 1.9g of potassium carbonate in a 100ml round bottom flask, add 50ml of N,N dimethylformamide, and carry out magnetic stirring under the protection of nitrogen, heating to temperature 70°C, reacted for 15 hours, and cooled to room temperature. After purification by column chromatography, the eluents were n-hexane and dichloromethane, and 1.08 g of the compound of formula (III-3) was isolated as a yellow oil.

[0116] The reaction equation is as follows:

[0117]

[0118] (3) preparation of formula (Ⅴ-3) compound

[0119] Weigh 0.94g formula (Ⅲ-3) compound, 0.5g formula (Ⅳ-1) compound 4-formylphenylboronic acid, 1.52g potassium carbonate and 0.12g tetrakistriphenylphosphine palladium in a 100ml round bottom flask, add 40ml Tetrahydrofuran and 10ml of water w...

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Abstract

The invention relates to the technical field of luminous materials, in particular to a tetraphenylethylene-phenanthroimidazole derivative and a crystal, preparation method and application thereof. Thedisclosed tetraphenylethylene-phenanthroimidazole derivative has a structure represented by a formula (I), wherein R1 is selected from -OCH3,-O(CH2)3CH3 and -O(CH2)5CH3 or a strong electron donatinggroup, and n is 1-2. In the derivative, tetraphenylethylene and phenanthroimidazole are connected through a benzene ring, and since an AIE effect can be generated by an extremely twisted structure oftetraphenylethylene, an ACQ effect of a luminous material with high concentration can be weakened by introducing a TPE group; the phenomenon of exciton annihilation can be effectively inhibited, so that molecules achieve stronger fluorescence emission in a high concentration aggregation state in comparison with a low concentration aggregation state. Meanwhile, because the relative molecular weightof the compound is large, a large conjugated structure exists, and the stability is high. According to experimental data, the provided tetraphenylethylene-phenanthroimidazole derivative can cause anobvious AIE phenomenon and has high thermal stability and luminous intensity.

Description

technical field [0001] The invention relates to the technical field of luminescent materials, in particular to a tetraphenylethylene-phenanthroimidazole derivative and its crystal, preparation method and application. Background technique [0002] Organic electroluminescence refers to the phenomenon of making organic materials emit light under the excitation of electric field or current. According to the different organic electroluminescent materials used, devices made of some special strong fluorescent organic small molecule materials are called organic electroluminescent devices (Organic Light-Emitting Diode), or organic light-emitting diodes. (OLED). OLED has the advantages of wide viewing angle, self-illumination, low operating voltage, thin panel, flexible, etc., and also has the potential of low cost, so it has broad application prospects in the field of flat panel display and solid light source. Its general structure is that a layer of organic electroluminescent mate...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D235/02C09K11/06H01L51/54H01L51/50
CPCC09K11/06C07D235/02C07B2200/13C09K2211/1044C09K2211/1007H10K85/6572H10K50/11
Inventor 王凯霍延平李陆军邱志鹏籍少敏
Owner GUANGDONG UNIV OF TECH
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