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A thermally induced delayed fluorescence compound and its preparation method and application

A delayed fluorescence, compound technology, applied in chemical instruments and methods, semiconductor/solid-state device manufacturing, organic chemistry, etc., can solve the problem of reducing the twist angle between donor/acceptor, molecular HOMO and LUMO cannot be effectively separated, and cannot be obtained. Good stability and high-efficiency TADF new materials, etc., to achieve the effect of high efficiency and breaking through the limit of external quantum efficiency

Active Publication Date: 2021-05-28
CHANGCHUN INST OF APPLIED CHEMISTRY - CHINESE ACAD OF SCI
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] In the current research on TADF materials, the common substitution positions of carbazole are the 3, 6 and 2, 7 positions, but due to the steric hindrance effect, it is difficult to introduce substituents at the 1, 8 positions of carbazole, especially it is difficult to introduce large steric hindrance. The aromatic group makes the carbon-nitrogen single bond between the carbazole donor group and the acceptor group connected by the nitrogen atom easy to rotate, thereby reducing the twist angle between the donor / acceptor and making the molecules HOMO and LUMO Effective separation cannot occur, and new TADF materials with good stability and high efficiency cannot be obtained

Method used

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  • A thermally induced delayed fluorescence compound and its preparation method and application
  • A thermally induced delayed fluorescence compound and its preparation method and application
  • A thermally induced delayed fluorescence compound and its preparation method and application

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preparation example Construction

[0074] The present invention also provides a preparation method of a heat-induced delayed fluorescence compound, comprising:

[0075] The compound having the structure of formula (II) is coupled with the compound of formula (III) to obtain the compound of structure shown in formula (I);

[0076]

[0077] Among them, R 1 , R 2 Independently selected from C1-C30 alkyl, C1-C30 alkoxy, C2-C36 dihydrocarbylamine, C6-C35 substituted aryl or C6-C35 unsubstituted aryl;

[0078] Ar is Ar 1 or Ar 2 ;

[0079] Ar 1 、Ar 2independently selected from C6~C50 substituted aryl, C6~C50 arylamine, C4~C50 substituted heteroaryl, C4~C50 substituted arylheterogroup or hydrogen, and Ar 1 、Ar 2 not simultaneously hydrogen;

[0080] A is a C6-C50 aryl group or a C3-C45 heteroaryl group containing an electron-withdrawing substituent;

[0081] x 1 、X 2 for bromine or hydrogen.

[0082] According to the present invention, the present invention couples the compound with the structure of fo...

Embodiment 1

[0100] Embodiment 1: the synthesis of compound AcPTC

[0101] The preparation process is shown in the following formula:

[0102]

[0103] The specific steps are:

[0104] 1,8-dibromo-9-(4-(4,6-diphenyl-1,3,5-triazine)phenyl)-3,6-di-tert-butylcarbazole (744mg, 1mmol), 4-(9,9'-dimethylacridin-10-yl)phenylboronic acid (1.32g, 4mmol), tris(dibenzylideneacetone)dipalladium (18mg, 0.02mmol), 2-bicyclohexylphosphine- 2',6'-dimethoxybiphenyl (32mg, 0.08mmol), potassium phosphate (1.06g, 4mmol) were added to a 50ml Schlenk bottle, tetrahydrofuran (10mL) and deoxygenated deionized water (2mL) were added, 80 ℃ reflux reaction for 24h. After the reaction, cool to room temperature, pour the reaction liquid into water, extract three times with dichloromethane, and combine the organic phases. The organic phase was washed three times with 100 ml of water, then dried over anhydrous sodium sulfate. The solution was filtered and concentrated. Separation was carried out through a silica...

Embodiment 2

[0105] Embodiment 2: the synthesis of compound PAPTC

[0106] The preparation process is shown in the following formula:

[0107]

[0108] The specific steps are:

[0109] 1,8-dibromo-9-(4-(4,6-diphenyl-1,3,5-triazine)phenyl)-3,6-di-tert-butylcarbazole (744mg, 1mmol), 4-(9,9'-dimethylacridin-10-yl)phenylboronic acid (1.16g, 4mmol), tris(dibenzylideneacetone)dipalladium (18mg, 0.02mmol), 2-bicyclohexylphosphine- 2',6'-dimethoxybiphenyl (32mg, 0.08mmol), potassium phosphate (1.06g, 4mmol) were added to a 50ml Schlenk bottle, tetrahydrofuran (10mL) and deoxygenated deionized water (2mL) were added, 80 ℃ reflux reaction for 24h. After the reaction, cool to room temperature, pour the reaction liquid into water, extract three times with dichloromethane, and combine the organic phases. The organic phase was washed three times with 100 ml of water, then dried over anhydrous sodium sulfate. The solution was filtered and concentrated. Separation was carried out through a silica...

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Abstract

The present invention provides a heat-induced delayed fluorescence compound and its preparation method and application. The compound provided by the present invention has a structure shown in formula (I). The present invention introduces a substituted aromatic group at the 1,8 positions of carbazole, and at the same time The other positions of the carbazole are supplemented with specific groups, so that the obtained compound has a small energy level difference between the first excited singlet state and the first excited triplet state, thereby realizing effective delayed fluorescence. Moreover, the photoluminescent efficiency of the compound is higher in the solid state, which is conducive to the full utilization of the triplet excitons. When the compound is applied to electroluminescent devices, it can break through the 5% external quantum efficiency limit of traditional fluorescent materials.

Description

technical field [0001] The invention relates to the field of organic luminescent materials, in particular to a heat-induced delayed fluorescence compound with limited rotation of an acceptor unit and its preparation and application. Background technique [0002] Since Deng Qingyun et al. (Applied Physics Letters: 1987, 51: 913-915.) invented the organic electroluminescent diode (OLED) with 8-hydroxyquinoline aluminum as the fluorescent small molecule light-emitting material in 1987, OLED has developed rapidly and made great progress. Because of its high luminous efficiency, low energy consumption, and fast response, it has become the research object of many researchers and related companies. Among them, luminescent materials, as key materials for OLED production, have attracted more attention. Traditional fluorescent materials can only use singlet excitons to emit light, and the internal quantum efficiency is limited to 25%. Phosphorescent materials can use the heavy atom ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D401/14C07D403/10C07D403/14C07D209/88C07D209/86C07D401/10C07D409/04C07D409/10C09K11/06H01L51/50H01L51/54
Inventor 程延祥李阔飞朱运会姚兵杨一可战宏梅
Owner CHANGCHUN INST OF APPLIED CHEMISTRY - CHINESE ACAD OF SCI
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