Acrylic ester and methyl acrylic ester kind side chain type luminous polymer and its synthesis

A technology of methacrylic acid and light-emitting polymer, applied in the directions of light-emitting materials, chemical instruments and methods, etc., can solve the problems of short service life of devices, low light-emitting efficiency of devices, urgent improvement of device stability, etc., and achieves a wide reaction temperature range. , the effect of mild reaction conditions

Active Publication Date: 2006-06-14
上海种亿化学技术有限公司
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] Organic electroluminescent devices are a multidisciplinary research field involving physics, chemistry, materials, and electronics. After decades of research and development, great achievements have been made, but there are still some problems on the road to mass production. The following problems: (1) The luminous efficiency of the device is still low; (2) The service life of the device is too short; (3) The stability of the device needs to be improved urgently; (4) The research on the luminescence mechanism is still not thorough
For general oil-soluble monomers, the temperature requirement of the polymerization reaction is relatively high, and a highly active initiating system is required to initiate, so it is difficult to realize the ATRP reaction at low temperature.

Method used

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  • Acrylic ester and methyl acrylic ester kind side chain type luminous polymer and its synthesis
  • Acrylic ester and methyl acrylic ester kind side chain type luminous polymer and its synthesis
  • Acrylic ester and methyl acrylic ester kind side chain type luminous polymer and its synthesis

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0036] Example 1: Synthesis of 4-(2'-cyanobiphenyl)methyl (meth)acrylate

[0037] 1. Hydrolysis of 2-cyano-4'-bromomethylbiphenyl

[0038] In 800ml of dilute alkali (potassium hydroxide or sodium hydroxide) with a concentration of 0.3 to 1%, add 1 to 3 g of 2-cyano-4'-bromomethylbiphenyl and heat to reflux, and filter off unreacted raw materials while hot. After cooling, crystals were precipitated, filtered and dried to obtain the hydrolyzed product 2-cyano-4'-hydroxymethyl biphenyl.

[0039] 2. Synthesis of 4-(2'-cyanobiphenyl)methyl (meth)acrylate

[0040] Take 4.0g of the above-mentioned hydrolyzed product 2-cyano-4'-hydroxymethyl biphenyl and dissolve it in 60-100ml tetrahydrofuran, add 7.0-9.0ml triethylamine under ice bath, and take another 4.0-6.0ml (methyl) Acryloyl chloride is dissolved in tetrahydrofuran (the volume ratio of the two is 1:4), and then added dropwise to the above solution, reacted under ice bath for 2-3 hours, and then reacted at room temperature for...

Embodiment 2

[0041] Example 2: Synthesis of (meth)acrylic acid-4'-(2-carboxybiphenyl)methyl ester

[0042] 1. Hydrolysis of 4'-bromomethylbiphenyl-2-carboxylate

[0043] In 800ml of 0.3-1% dilute alkali (potassium hydroxide or sodium hydroxide), add 2-4 grams of 4'-bromomethylbiphenyl-2-methyl carboxylate and heat to reflux, and filter off unreacted raw materials while hot , cooled, crystals were precipitated, filtered and dried to obtain the hydrolyzed product 4'-hydroxymethylbiphenyl-2-carboxylic acid.

[0044] With other 4'-bromomethylbiphenyl-2-carboxylic acid alkyl esters as raw materials, corresponding reactions can also occur to obtain 4'-hydroxymethylbiphenyl-2-carboxylic acid.

[0045] 2. Synthesis of (meth)acrylic acid-4'-(2-carboxybiphenyl)methyl ester

[0046]Take 4.2g of the above hydrolyzed product 4'-hydroxymethylbiphenyl-2-carboxylic acid and dissolve it in 60~100ml tetrahydrofuran, add 7.0~9.0ml triethylamine under ice bath, and take another 4.0~6.0ml (meth)propylene Th...

Embodiment 3

[0047] Embodiment Three: Synthesis of (meth)acrylate-4-(biphenyl)methyl ester

[0048] 1. Hydrolysis of 4-bromomethylbiphenyl

[0049] In 800ml of 0.3-1% dilute alkali (potassium hydroxide or sodium hydroxide), add 1-3g of 4-bromomethylbiphenyl and heat to reflux, filter off unreacted raw materials while hot, cool down, precipitate crystals, filter and dry In the hydrolysis product 4-hydroxymethyl biphenyl.

[0050] 2. Synthesis of 4-(biphenyl)methyl (meth)acrylate

[0051] Take 3.6g of the above-mentioned hydrolyzed product 4-hydroxymethylbiphenyl and dissolve it in 60-100ml tetrahydrofuran, add 7.0-9.0ml triethylamine under ice bath, and take another 4.0-6.0ml (meth)acryloyl chloride and dissolve it in tetrahydrofuran ( The volume ratio of the two is 1:4), and then added dropwise to the above solution, reacted under ice bath for 2-3 hours, and then reacted at room temperature for 8-16 hours. The reactant was washed successively with dilute alkali and dilute acid to obtain...

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Abstract

The present invention discloses an acrylate and methylacrylate side chain type luminescent polymer. It is characterized by that on the side chain of polymer the diphenyl group is contained. Said invention also provides the method adopted for synthesizing said polymer and monomer synthesized in the reaction process. Said invention can utilize an atomic transfer free radical polymerization method to synthesize a new side-chain type luminescent polymer.

Description

technical field [0001] The present invention relates to a class of (meth)acrylic ester monomers containing biphenyl groups, and side-chain light-emitting polymers synthesized from the monomers through atom transfer radical polymerization; the present invention also relates to their synthesis method. Background technique [0002] Light-emitting polymers have attracted widespread attention because of their good application prospects as fluorescent materials and electroluminescent materials. Electroluminescent devices made of organic small molecule materials have been put into practical use, and the products are mainly focused on small screen displays. For example, Philips in the Netherlands has built a production line for organic electroluminescent devices, which are mainly used for the production of mobile phones and other portable devices. The backlight display of electronic equipment, and the light-emitting devices based on organic polymer material...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C09K11/06C08F20/10
Inventor 路建美张振江徐庆锋王丽华夏雪伟
Owner 上海种亿化学技术有限公司
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