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Conjugated polymer and preparation method and application thereof

A conjugated polymer and polymer technology, which is used in semiconductor/solid-state device manufacturing, electrical components, circuits, etc., can solve the problem that conjugated polymers cannot meet market demands, and achieves improved device application range and high external quantum efficiency. , the effect of good luminous performance

Active Publication Date: 2020-05-19
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

However, the currently developed conjugated polymers still cannot meet the market demand. Therefore, it is still of great significance to further improve the luminescent properties of conjugated polymers to prepare high-efficiency polymer electroluminescent materials.

Method used

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  • Conjugated polymer and preparation method and application thereof
  • Conjugated polymer and preparation method and application thereof
  • Conjugated polymer and preparation method and application thereof

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preparation example Construction

[0061] The present invention also provides a kind of preparation method of polymer described in 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) or formula (V) to obtain the polymer with the structure shown in formula (I);

[0063]

[0064]

[0065] Wherein, D is a C6-C50 aryl group with electron-donating ability or a C5-C50 heteroaryl group with electron-donating ability;

[0066] Ar is a C6-C50 aryl group or a C4-C50 heteroaryl group;

[0067] R 1 is H, halogen or cyano;

[0068] n is 1-200;

[0069] x is 0

[0070] According to 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 or formula (V) structure copolymerization, obtain the polymer of the structure shown in formula (I) Wh...

Embodiment 1

[0075] Embodiment 1: the synthesis of polymer PCzAQC0.1

[0076] (1) Synthesis of 9,9-dihexyl-2,7-dimethyl-9,10-dihydroacridine

[0077] The preparation process is shown in the following formula:

[0078]

[0079] The specific steps are:

[0080] Methyl 2-(N-p-methylphenyl)amino-5-methylbenzoate (27.9g, 109.4mmol) was added to a 500mL three-necked flask, pumped and ventilated several times, protected by argon, and anhydrous and oxygen-free The tetrahydrofuran (120mL) was stirred and dissolved, and then the newly prepared tetrahydrofuran solution of Grignard reagent hexylmagnesium bromide (156mL, 2.9mol / L) was slowly added to the reaction system. Hydrochloric acid aqueous solution (400mL, 1mol / L), extracted with ether, and the organic phase was evaporated under reduced pressure to remove the solvent to obtain the intermediate; the intermediate, 240mL glacial acetic acid and 60mL concentrated hydrochloric acid were added to a 500mL single-necked flask, refluxed and condense...

Embodiment 2

[0097] Embodiment 2: the synthesis of polymer PCzAQC0.3

[0098] The preparation process is shown in the following formula:

[0099]

[0100] The specific steps are:

[0101] Accurately weigh 5,8-dibromo-2,3-bis(4-(9,9-dihexyl-2,7-dimethylacridin-10(9 hydrogen) base)phenyl)quinoxaline- 6,7-dinitrile (1.5mg, 0.0012mmol), 2,7-dibromo-9-heptadecylcarbazole (112.0mg, 0.1988mmol), 2,7-dipinacol borate-9 -Heptadecylcarbazole (131.5mg, 0.20mmol) and bis(tris(o-methylphenyl)phosphine)palladium dichloride (1.6mg, 0.002mmol) were placed in a 50mL Schlenk bottle, and the gas was exchanged several times, Under argon protection, add anhydrous and oxygen-free tetrahydrofuran (15 mL), stir to dissolve, then add tripotassium phosphate aqueous solution (1 mL, 2 mmol / mL), heat up to 50 ° C for 0.5 h; dissolve phenylboronic acid (0.20 g, 1.6mmol) was added to the system for 5h; 0.3mL bromobenzene was added to the system for 5h; sodium diethylcarbamate (0.2g) dissolved in 10mL of water was ...

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Abstract

The invention provides a conjugated polymer and a preparation method and application thereof. The main chain of the polymer with the structure as shown in the formula (I) contains an electron acceptorof quinoxaline or a derivative thereof, and a side group is an electron donor. What is found through experiments is that the energy level difference between the first excited singlet state and the first excited triplet state of the conjugated polymer is small, and therefore the conjugated polymer has E-type delayed fluorescence emission and is long-wavelength red to dark red E-type delayed fluorescence emission. The polymer provided by the invention has good luminescence property and low turn-on voltage when being applied to an electroluminescent device, and the obtained electroluminescent device not only has high external quantum efficiency under a low-brightness condition, but also has high external quantum efficiency under a high-brightness condition, so that the application range of the device is expanded.

Description

technical field [0001] The invention relates to the field of organic electroluminescent materials, in particular to a conjugated polymer whose main chain contains quinoxaline or derivatives thereof, 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 because of the same lifetime of phosphorescence associated with it. 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 the E-type delayed fluorescence is that the energy level difference between the first excited singlet state an...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08G61/12H01L51/50H01L51/54
CPCC08G61/124C08G61/122C08G61/126C08G2261/122C08G2261/143C08G2261/1412C08G2261/18C08G2261/3241C08G2261/411C08G2261/5222C08G2261/3243H10K85/151H10K50/11H10K2101/40H10K50/12
Inventor 程延祥汪涛李阔飞姚兵衣小虎
Owner CHANGCHUN INST OF APPLIED CHEMISTRY - CHINESE ACAD OF SCI
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