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

A technology of conjugated polymers and aroyl groups, which is applied in the field of conjugated polymer delayed fluorescence materials and its preparation, can solve the problems of increasing material cost and difficulty in structural modification, difficulty in achieving delayed fluorescence emission, and far from reaching performance. Achieve the effect of simple preparation method, inhibition of efficiency roll-off, and efficiency roll-off

Active Publication Date: 2019-06-21
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 large conjugated delocalization systems make it difficult to achieve delayed fluorescence emission, although non-conjugated polymers with E-type delayed fluorescence can be obtained through flexible connections and ingenious synthesis methods (Adv. Mater .2015, 27, 7236), but it is far from the expected performance. Recently, we synthesized a conjugated polymer with E-type delayed fluorescence by the method of alternating copolymerization (Macromolecules 2016, 49, 4373), but in the literature The highest external quantum efficiency of the obtained conjugated polymer is only 12.6%, and the efficiency rolls off seriously

Method used

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

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preparation example Construction

[0075] The present invention also provides a preparation method of the conjugated polymer containing aroyl groups in the side chain of the present invention, comprising:

[0076] 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);

[0077]

[0078] Among them, 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 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 compound of structure shown in formula (I); Wherein, in the structure R1 , R2, Ar, x and n are selected in the same range as ...

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 containing an aroyl group in the side chain and its preparation method and application. The conjugated polymer containing an aroyl group in the side chain has the structure of formula (I). The polymer provided by the invention is the first The energy level difference between the first excited singlet state and the first excited triplet state is small, so that the polymer has E-type delayed fluorescence emission, and the conjugated polymer provided by the present invention is selected by selecting a specific polymer unit and selecting a specific polymer unit ratio, so that the obtained conjugated polymer can be applied to electroluminescent devices, and the external quantum efficiency of the electroluminescent device made by using the obtained conjugated polymer is high, and the polymer provided by the invention can effectively inhibit Efficiency roll-off of electroluminescent devices; 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 make devices, which greatly simplifies A method for fabricating electroluminescent devices.

Description

technical field [0001] The invention relates to the field of organic luminescent materials, in particular to a conjugated polymer delayed fluorescence material containing an aroyl group in a side chain, 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 stat...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C08G61/12C09K11/06H01L51/54
CPCC09K11/06C08G61/122C08G61/124C08G2261/95C08G2261/5222C08G2261/12C08G2261/18C08G2261/3241C08G2261/1428C08G2261/143C08G2261/1412C09K2211/1466H10K85/111
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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