Conjugated polymer with aryl-containing side chain, and preparation method and applications thereof

A conjugated polymer and aroyl technology, which is applied in the field of conjugated polymer delayed fluorescent materials and their preparation, can solve the problems of increasing the cost of materials and the difficulty of structural modification, difficult to achieve delayed fluorescent emission, and far from achieving performance, etc. To achieve the effect of simple preparation method, inhibition of efficiency roll-off, and efficiency roll-off

Active Publication Date: 2017-08-18
CHANGCHUN INST OF APPLIED CHEMISTRY - CHINESE ACAD OF SCI
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, the external quantum efficiency of traditional conjugated polymer fluorescent materials can only reach 5-6%.
An effective way to improve device performance is to introduce "chemical doping" of phosphorescent units of heavy metal complexes in polymers, thereby making full use of the singlet and triplet excitons produced, and the external quantum efficiency can reach 20% (J.Am .Chem.Soc.2012, 134, 15189; Adv.Funct.Mater.2008, 18, 1430), but the introduction of phosphorescent units increases the cost of materials and the difficulty of structural modification
The inherent characteristics of conjugated polymers such as

Method used

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  • Conjugated polymer with aryl-containing side chain, and preparation method and applications thereof
  • Conjugated polymer with aryl-containing side chain, and preparation method and applications thereof
  • Conjugated polymer with aryl-containing side chain, and preparation method and applications thereof

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preparation example Construction

[0075] The present invention also provides a method for preparing the side chain aroyl-containing conjugated polymer of the present invention, comprising:

[0076] 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);

[0077]

[0078] where R 1 , R 2 independently selected from C1-C30 alkyl, C1-C30 alkoxy or C6-C35 substituted aryl;

[0079] Ar is a C6-C50 aryl group or a C3-C45 heteroaryl group;

[0080] x is 0

[0081] n is 1-200.

[0082] 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 compound of the structure of formula (I); wherein, R1 in the structure , R2, Ar, x and n are selected in the same range as the aforementioned conjugated polymer; the present i...

Embodiment 1

[0086] Example 1: Synthesis of Polymer PAPBPC50

[0087] The preparation process is shown in the following formula:

[0088]

[0089] The specific steps are:

[0090] 2,7-dibromo-9,9-dihexyl-10-(4-phenylbenzoyl)-9,10-dihydroacridine (0.688g, 1.0mmol), 3,6-dipinacol Borate-9-heptadecylcarbazole (0.658g, 1.0mmol), bis(tri-o-methylphenylphosphine)palladium dichloride (0.008g, 0.01mmol), potassium phosphate (1.698g, 8.0mmol ) was added to a 100mL Schlenk bottle, pumped and exchanged three times, protected by argon, added deoxygenated and dried tetrahydrofuran (20mL) and deoxygenated deionized water (4mL), and refluxed at 80°C for 24h; benzene dissolved in 4mL of tetrahydrofuran Boric acid (0.012g, 0.1mmol) was injected into the reaction solution, reacted for 6h, and then 2mL of oxybenzene was injected into the reaction solution, and reacted for 6h; Diethylcarbamate sodium (1.0g) dissolved in 20mL of water was added to the reaction solution Continue to stir for 12 hours; cool...

Embodiment 2

[0092] Example 2: Synthesis of polymer PAPBPC25

[0093] The preparation process is shown in the following formula:

[0094]

[0095] The specific steps are:

[0096] 2,7-dibromo-9,9-dihexyl-10-(4-phenylbenzoyl)-9,10-dihydroacridine (0.344g, 0.5mmol), 3,6-dioxyl- 9-heptadecylcarbazole (0.282g, 0.5mmol), 3,6-dipinacol borate-9-heptadecylcarbazole (0.658g, 1.0mmol), bis(tri-o-methyl Phenylphosphine)palladium dichloride (0.008g, 0.01mmol) and potassium phosphate (1.698g, 8.0mmol) were added to a 100mL Schlenk bottle, the gas was exchanged 3 times, protected by argon, and deoxygenated and dried tetrahydrofuran (20mL ) and deoxygenated deionized water (4mL), reflux at 80°C for 24h; inject phenylboronic acid (0.012g, 0.1mmol) dissolved in 4mL of tetrahydrofuran into the reaction solution, react for 6h, then inject 2mL of bromobenzene into the reaction solution, React for 6h; add sodium diethylcarbamate (1.0g) dissolved in 20mL of water to the reaction solution, and continue st...

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Abstract

The invention provides a conjugated polymer with an aryl-containing side chain, and a preparation method and applications thereof. The conjugated polymer with an aryl-containing side chain has a structure shown as the formula (I). The energy difference between a first excited singlet state and a first excited triplet state of the polymer is small, so that the polymer has E type delay fluorescent emission, the corrugated polymer can be applied to an electroluminescence device by selecting specific polymer units and selecting a specific polymer unit ratio, the external quantum efficiency of the electroluminescence device prepared from the obtained corrugated polymer is high, and the efficiency roll-off of the electroluminescence device can be efficiently inhibited by utilizing the polymer. In addition, the preparation method of the polymer is simple, and the device can be prepared by using spin-coating, ink-jet printing and other simple solution processing modes when the polymer is used for manufacturing the device, so that the preparation method of the electroluminescence device can be greatly simplified.

Description

technical field [0001] The invention relates to the field of organic light-emitting materials, in particular to a conjugated polymer delayed fluorescent material containing an aroyl group in the side chain and a preparation method and application thereof. Background technique [0002] E-type delayed fluorescence was first discovered in the organic fluorescent dye eosin (Eosin), named after the same phosphorescence lifetime associated with it. 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 E-type delayed fluorescence is that the energy level difference between the first...

Claims

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Application Information

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IPC IPC(8): C08G61/12C09K11/06H01L51/54
CPCC09K11/06C08G61/122C08G61/124C08G2261/95C08G2261/5222C08G2261/12C08G2261/18C08G2261/3241C08G2261/1428C08G2261/143C08G2261/1412C09K2211/1466H10K85/111
Inventor 程延祥杨一可朱运会王淑萌战宏梅
Owner CHANGCHUN INST OF APPLIED CHEMISTRY - CHINESE ACAD OF SCI
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