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Side-chain liquid crystal polymer with aggregation-induced emission property and preparation method thereof

A technology of aggregation-induced luminescence and side-chain type liquid crystal, which is applied in liquid crystal materials, chemical instruments and methods, etc., to achieve good application prospects, obvious aggregation-induced luminescence effect, and easy purification.

Inactive Publication Date: 2017-08-04
XIANGTAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] The purpose of the present invention is to provide a new type of side chain type liquid crystal polymer luminescent material with simple synthesis and excellent luminescent performance and its preparation method in view of the current research status of luminescent liquid crystal polymer materials

Method used

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  • Side-chain liquid crystal polymer with aggregation-induced emission property and preparation method thereof
  • Side-chain liquid crystal polymer with aggregation-induced emission property and preparation method thereof
  • Side-chain liquid crystal polymer with aggregation-induced emission property and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0047] 1. Synthesis of cyano-stilbene derivatives

[0048] Add p-octadecyloxybenzaldehyde (10.0g, 26.7mmol), NaOH (2.14g, 53.4mmol) and 150ml of dehydrated alcohol successively in a 250ml single-necked bottle, then add p-hydroxyphenylacetonitrile (3.6g, 26.7 mmol), reflux at 85°C for 4 hours, then cool the reaction solution to room temperature, then pour it into a large amount of ice water for precipitation, filter with suction, wash the filter cake with dilute hydrochloric acid and deionized water successively, and collect the crude product under vacuum at 35°C After drying for 48 h, the dried crude product was recrystallized from ethyl acetate to obtain a pale yellow pure solid product.

[0049] 2. Synthesis of cyano-stilbene derivatives containing flexible spacers

[0050] Add 4-hydroxyl-4'-octadecyloxycyano-stilbene (4.5g, 9.2mmol), anhydrous potassium carbonate (3.8g, 27.6mmol) and the acetone of 150ml successively in a 250ml single-necked bottle, and then Add 1,6-dibro...

Embodiment 2

[0057] 1. Synthesis of cyano-stilbene derivatives

[0058] Same as Example 1

[0059] 2. Synthesis of cyano-stilbene derivatives containing flexible spacers

[0060] Add 4-hydroxy-4'-octadecyloxycyano-stilbene (10.0g, 20.4mmol), anhydrous potassium carbonate (8.5g, 61.2mmol) and 120ml of DMF successively in a 250ml single-necked bottle, and then Add 1,4-dibromobutane (8.8g, 40.8mmol) and react at 65°C for 24h under magnetic stirring in an oil bath, then slowly add the reaction solution to 1000ml of ice water for precipitation, suction filter, and vacuum dry at 35°C for 48h , the crude product was filtered with dichloromethane to remove insoluble solid impurities, and the filtrate was spin-dried to obtain a light blue solid powder.

[0061] 3. Synthesis of flexible spacer monomers

[0062] In a 250ml round bottom flask, add 4-bromobutoxy-4'-hexyloxycyano toluene (15.0g, 24.0mmol), then add potassium bicarbonate (7.2g, 71.2mmol), DMF120ml and Methacrylic acid (2.1g, 48.0mmol...

Embodiment 3

[0067] 1. Synthesis of cyano-stilbene derivatives

[0068] Same as Example 1

[0069] 2. Synthesis of cyano-stilbene derivatives containing flexible spacers

[0070] Add 4-hydroxyl-4'-octadecyloxycyano-stilbene (10.0g, 20.4mmol), anhydrous potassium carbonate (7.1g, 51.1mmol) and 120ml of acetone successively in a 250ml single-necked bottle, and then Add 1,8-dibromooctane (8.3g, 30.6mmol) and react at 65°C for 16h under magnetic stirring in an oil bath, then slowly add the reaction solution into 1000ml of ice water to precipitate, filter with suction, and dry in vacuum at 35°C for 48h , the crude product was filtered with dichloromethane to remove insoluble solid impurities, and the filtrate was spin-dried to obtain a light blue solid powder.

[0071] 3. Synthesis of flexible spacer monomers

[0072] In a 250ml round bottom flask, add 4-bromooctyloxy-4'-octadecyloxycyano-stilbene (20.0g, 29.4mmol), then add potassium bicarbonate (7.4g, 73.6mmol), Acetone 150ml and methacry...

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Abstract

The invention discloses a side-chain liquid crystal polymer with aggregation-induced emission property and a preparation method thereof. A substituted cyano-distyrene compound is generated by using a substituent-containing para benzaldehyde derivative and hydroxybenzyl cyanide through Knoevenagel reaction, so that, on one hand, the substituted cyano-distyrene compound can react with polymerizable double bond-containing acids such as saturated dihalide, methacrylic acid or acrylic acid in sequence to generate a polymerizable monomer and a side-chain liquid crystal polymer with a flexible spacer is obtained through free radical polymerization; and on the other hand, the substituted cyano-distyrene compound can directly react with polymerizable double bond-containing acyl chloride such as methacryloyl chloride or acryloyl chloride to generate the polymerizable monomer and a side-chain liquid crystal polymer free of the flexible spacer is obtained through free radical polymerization. A fluorescent chromogenic group and a liquid crystal unit are combined into one; the method is simple in synthesis and easy to purify, and the obtained polymer has an obvious aggregation-induced emission effect, has excellent liquid crystal property and has a good application prospect.

Description

technical field [0001] The invention belongs to the technical field of organic light-emitting materials, and in particular relates to a side-chain type liquid crystal polymer with aggregation-induced light-emitting performance and a preparation method thereof. Background technique [0002] Luminescent liquid crystals have aroused great interest of researchers because of their important applications in optical devices such as anisotropic light-emitting diodes and light-emitting liquid crystal displays. Eu(TTA) 3 (TTA: thienyl trifluoroacetone) was mixed into the nematic liquid crystal 4-n-pentyl-4-cyanobiphenyl to obtain a red light emitting sample material, creating a new field of research on rare earth liquid crystal materials; Deum etc. (Journal of Materials Chemistry, 2003,13,1520) transform different rare earth ion complexes Nd(dbm) 3 -(phen), Er(dbm) 3 -(phen) and Yb(dbm) 3 -(phen) was doped into nematic liquid crystal MBBA, and the near-infrared luminescence phenom...

Claims

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Application Information

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IPC IPC(8): C08F120/36C09K19/38
CPCC08F120/36C09K19/3852
Inventor 张海良袁勇杰黎金娣廖军秋
Owner XIANGTAN UNIV
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