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Conjugated polymer with side chain containing triazine group as well as preparation method and application of conjugated polymer

A technology of conjugated polymer and triazine group, applied in the field of conjugated polymer and its preparation, can solve problems such as efficiency roll-off, and achieve the effects of improving performance, simple preparation method and improving current efficiency

Active Publication Date: 2017-06-20
CHANGCHUN INST OF APPLIED CHEMISTRY - CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] Recently, we synthesized conjugated polymers with TADF by alternating copolymerization (Macromolecules2016, 49, 4373). The highest external quantum efficiency of polymer devices obtained in this work is only 12.6%, and the efficiency rolls off seriously.

Method used

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  • Conjugated polymer with side chain containing triazine group as well as preparation method and application of conjugated polymer
  • Conjugated polymer with side chain containing triazine group as well as preparation method and application of conjugated polymer
  • Conjugated polymer with side chain containing triazine group as well as preparation method and application of conjugated polymer

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preparation example Construction

[0061] The present invention also provides a preparation method of the conjugated polymer containing triazine groups in the side chain of the present invention, comprising:

[0062] Copolymerize the compound with the structure of formula (II), the compound with the structure of formula (III) and the compound with the structure of formula (IV) to obtain the compound with the structure shown in formula (I);

[0063]

[0064] Among them, R 1 , R 3 independently selected from C1-C30 alkyl, C1-C30 alkoxy, C6-C35 unsubstituted aryl or C6-C35 substituted aryl;

[0065] R 2 C1-C30 alkyl, C1-C30 alkoxy, C6-C35 unsubstituted aryl, C6-C35 unsubstituted phenol, C6-C35 substituted aryl or C6-C35 substituted phenol;

[0066] x is 0.001

[0067] n is 2-200.

[0068] In the present invention, the present invention will have the compound of formula (II) structure, the compound of formula (III) structure and the compound of formula (IV) structure to copolymerize, obtain the comp...

Embodiment 1

[0073] Example 1: Synthesis of Polymer PCz-HAPT35%

[0074] 1) Preparation of unbrominated formula (II) structural compound

[0075] The preparation process is shown in the following formula:

[0076]

[0077] The specific steps are:

[0078] 9,9-dihexyl-9,10-dihydroacridine (2.0g, 3.7mmol), 4,6-di-tert-butyl-2-p-bromophenyl-1,3,5-triazine (1.3 g, 3.7mmol), Pd2 (dba) 3 (0.003g, 0.04mmol), DPPF (0.005g, 0.08mmol), sodium tert-butoxide (0.71g, 7.4mmol) were added in a 100ml three-necked flask, and 20ml of dry Toluene was pumped out, protected by argon, condensed at 80°C for 20 hours, cooled to room temperature, extracted with water and dichloromethane, the organic phase was rotary evaporated, and separated by a column to obtain 2.0 g of the product with a yield of 90%.

[0079]The obtained product is carried out nuclear magnetic resonance detection, and its hydrogen spectrum is: 1 H NMR (400MHz, CDCl 3 )68.84(d, J=8.3Hz, 2H), 7.40(d, J=8.3Hz, 2H), 7.30(m, 2H), 6.94-6.81(...

Embodiment 2

[0091] Example 2: Synthesis of Polymer PCz-HAPT25%

[0092]

[0093] The specific steps are:

[0094] 2,7-Dibromo-9,9-dihexyl-10-(6-(4',6'-di-tert-butyl-1,3,5-triazine))phenyl-9,10-dihydro Acridine (0.194g, 0.25mmol), 3,6-dibromo-9-heptadecylcarbazole (0.141g, 0.25mmol), 3,6-dipinacol borate-9-heptadecane Carbazole (0.329g, 0.5mmol), bis(tri-o-methylphenylphosphine) palladium dichloride (0.004g, 0.005mmol), and potassium phosphate solution (2M, 1.6ml) were added to a 50ml one-necked flask In the middle, pump and exchange gas, protect with argon, add deoxygenated tetrahydrofuran (8ml), reflux reaction at 80°C for 24h; inject phenylboronic acid (0.015g, 0.1mmol) dissolved in 2ml tetrahydrofuran into the reaction solution, react for 6h, and then Bromobenzene (0.1ml) dissolved in 2ml of tetrahydrofuran was injected into the reaction solution and reacted for 6h; Diethylcarbamothiocarbamate (1g) dissolved in 20ml of water was added to the reaction solution and continued to stir...

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Abstract

The invention provides a conjugated polymer with a side chain containing a triazine group as well as a preparation method and application of the conjugated polymer. The conjugated polymer provided by the invention has a structure represented by formula (I) (as shown in the description). By selecting a specific polymer unit and a proportion of the specific polymer unit, the concentration quenching effect of light-emitting kernel with an E-form delayed fluorescence emitting effect is adequately inhibited, and therefore, the photoluminescence quantum efficiency is remarkably improved; and an electroluminescence device prepared from the conjugated polymer is improved, meanwhile, a roll-off effect of the electroluminescence device under a high light condition is effectively inhibited. Besides, the preparation method of the polymer is simple, and when the polymer is used for preparing a device, the device can be prepared by virtue of simple solution processing manners such as spinning and spray ink printing, so that the preparation method of the electroluminescence device is greatly simplified.

Description

technical field [0001] The invention relates to the field of organic luminescent materials, in particular to a conjugated polymer containing a specific content of triazine groups in side chains and a preparation method and application thereof. Background technique [0002] E-type delayed fluorescence was first discovered in the organic fluorescent dye eosin (Eosin), which was named for its similar phosphorescence lifetime. E-type delayed fluorescence compounds include common organic small molecules such as fluorescein and acridine yellow (Acridine), and the fluorescence intensity of these compounds increases with temperature within a certain range, so E-type delayed fluorescence is also called It is heat-assisted or heat-induced delayed fluorescence [thermoassistant or thermally activated delayed fluorescence (TADF)]. The basic reason for producing TADF is that the energy level difference between the first excited singlet state and the first excited triplet state is small e...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08G61/12C09K11/06H01L51/54
CPCC09K11/06C08G61/122C08G61/124C08G2261/5222C08G2261/95C08G2261/18C08G2261/143C08G2261/3241C08G2261/1412C08G2261/12C09K2211/1466H10K85/111
Inventor 程延祥朱运会杨一可张保华王彦杰战宏梅
Owner CHANGCHUN INST OF APPLIED CHEMISTRY - CHINESE ACAD OF SCI
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