A kind of conjugated polymer containing triazine group in side chain and its preparation method and application

A technology of conjugated polymers and triazine groups, applied in the field of conjugated polymers and their preparation, can solve problems such as efficiency roll-off, achieve the effects of improving performance, inhibiting concentration quenching, and simplifying the preparation method

Active Publication Date: 2019-06-21
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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  • A kind of conjugated polymer containing triazine group in side chain and its preparation method and application
  • A kind of conjugated polymer containing triazine group in side chain and its preparation method and application
  • A kind of conjugated polymer containing triazine group in side chain and its preparation method and application

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preparation example Construction

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

[0062] Copolymerizing the compound having the structure of formula (II), the compound of formula (III) and the compound of formula (IV) to obtain the compound of the structure of formula (I);

[0063]

[0064] where 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 group, C1-C30 alkoxy group, C6-C35 unsubstituted aryl group, C6-C35 unsubstituted phenol group, C6-C35 substituted aryl group or C6-C35 substituted phenol group;

[0066] x is 0.001

[0067] n is 2-200.

[0068] In the present invention, the present invention copolymerizes the compound with the structure of formula (II), the compound of the structure of formula (III) and the compound of the structure of formula (IV) to obtain the compoun...

Embodiment 1

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

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

[0075] The preparation process is as follows:

[0076]

[0077] The specific steps are:

[0078] 9,9-Dihexyl-9,10-dihydroacridine (2.0 g, 3.7 mmol), 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 to a 100ml three-necked flask, and 20ml of dry Toluene, ventilation, argon protection, condensation reaction at 80°C for 20h, cooled to room temperature, extracted with water and dichloromethane, the organic phase was rotary evaporated, and column separated to obtain 2.0g of product with a yield of 90%.

[0079]The obtained product was detected by nuclear magnetic resonance, and its hydrogen spectrum was: 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(m, 4H), 6.19(d, J=8.8Hz, 2H), 2...

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 boronate-9-heptadecane Base carbazole (0.329g, 0.5mmol), bis(tri-o-methylphenylphosphonium) palladium dichloride (0.004g, 0.005mmol), deoxygenated potassium phosphate solution (2M, 1.6ml) were added to a 50ml single-necked flask In the middle, pump and ventilate, argon protection, add deoxygenated tetrahydrofuran (8ml), reflux at 80°C for 24h reaction; inject phenylboronic acid (0.015g, 0.1mmol) dissolved in 2ml of tetrahydrofuran into the reaction solution, react for 6h, and then add Bromobenzene (0.1ml) dissolved in 2ml of tetrahydrofuran was injected into the reaction solution and reacted for 6h; sodium diethylaminothiocarbamate (1g) dissolved in 20ml of water was added to the reaction so...

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Abstract

The invention provides a conjugated polymer containing a triazine group in the side chain and its preparation method and application. The conjugated polymer provided by the invention has a structure of formula (I), and the conjugated polymer provided by the invention is obtained by selecting The specific polymer unit and the selected ratio of the specific polymer unit enable the concentration quenching effect of the luminescent nucleus with E-type delayed fluorescence emission to be fully suppressed, thereby significantly improving its photoluminescence quantum efficiency. The efficiency of the electroluminescence device prepared by this polymer is also improved, and at the same time, the roll-off effect at high brightness is effectively suppressed. In addition, the preparation method of the polymer provided by the present invention is simple, and the obtained polymer can be prepared by simple solution processing methods such as spin coating and inkjet printing when used to prepare devices, which greatly simplifies the preparation method of electroluminescent devices.

Description

technical field [0001] The invention relates to the field of organic light-emitting materials, in particular to a conjugated polymer containing a triazine group in a side chain of a specific content and a preparation method and application thereof. Background technique [0002] E-type delayed fluorescence was first discovered in the organic fluorescent dye eosin (Eosin). E-type delayed fluorescence compounds include common small organic molecules such as Fluorescein and Acridine. These compounds increase with temperature and fluorescence intensity within a certain range. Therefore, E-type delayed fluorescence is also called E-type delayed fluorescence. For thermally assisted or thermally induced delayed fluorescence [thermoassistant or thermally activated delayedfluorescence (TADF)]. The basic reason for the generation of TADF is that the energy level difference between the first excited singlet state and the first excited triplet state is small enough. At this time, the co...

Claims

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Application Information

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Patent Type & Authority Patents(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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