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Acridine D-A type thermal activation delayed fluorescent material as well as preparation method and application thereof

A technology of heat-activated delayed and fluorescent materials, which is applied in the fields of luminescent materials, chemical instruments and methods, organic chemistry, etc., to achieve the effects of high yield, novel material structure and high efficiency

Inactive Publication Date: 2018-09-14
NINGBO INST OF MATERIALS TECH & ENG CHINESE ACADEMY OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] The invention provides an acridine-type D-A thermally activated delayed fluorescent material, which contains a similar electron-donating group acridine, and the overall structure of the material is changed by introducing different electron-withdrawing groups such as benzene ring, fluorene, carbazole and sulfone. structure, to achieve high-purity, multi-color luminescence, especially blue light, which can improve the lack of thermally activated delayed fluorescent materials for blue light and poor performance.

Method used

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  • Acridine D-A type thermal activation delayed fluorescent material as well as preparation method and application thereof
  • Acridine D-A type thermal activation delayed fluorescent material as well as preparation method and application thereof
  • Acridine D-A type thermal activation delayed fluorescent material as well as preparation method and application thereof

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Experimental program
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Effect test

Embodiment 1

[0032] In this embodiment, the structural formula of the thermally activated delayed fluorescent material BP-Ph-DPAC is as follows:

[0033]

[0034] The synthetic route of the above-mentioned thermally activated delayed fluorescent material is as follows:

[0035]

[0036] The specific synthesis process is as follows:

[0037] 4-benzoyl-4-bromobiphenyl (0.337g, 1.0mmol), 9,10-dihydro-9,9-diphenylacridine (0.37g, 1.1mmol), tri-tert-butylphosphine tetra Fluoroborate (0.02g) and sodium tert-butoxide (0.2g) were added to a 100ml three-neck flask, vacuum replaced three times with nitrogen, and 20ml of dried toluene was added. Stir at room temperature for 15 min, add Pd 2 (dba) 3 (0.02g), stirred at 120°C for 18h. Cool to room temperature, pass through the elution column (eluted with DCM), spin dry, add silica gel powder for sample preparation, and perform column chromatography separation. 0.54 g of white solid (Y=92%) was obtained, which was recrystallized from hexane / c...

Embodiment 2

[0040] In this embodiment, the structural formula of the thermally activated delayed fluorescent material DPAC-PS-DPAC is as follows:

[0041]

[0042] The synthetic route of the above-mentioned thermally activated delayed fluorescent material is as follows:

[0043]

[0044] The specific synthesis process is as follows:

[0045] 4,4'-dibromodiphenylsulfone (0.11g, 0.3mmol), 9,10-dihydro-9,9-diphenylacridine (0.23g, 0.66mmol), tri-tert-butylphosphine tetrafluoro Add borate (0.02g) and sodium tert-butoxide (0.2g) into a 100ml three-necked flask, vacuumize and replace nitrogen three times, and add 20ml of dried toluene. Stir at room temperature for 15 min, add Pd 2 (dba) 3 (0.02g), stirred at 120°C for 18h. Cool to room temperature, elute through the column (eluted with DCM), spin dry, add silica gel powder to prepare a sample, and perform column chromatography to obtain 0.21 g of white solid (Y=79%).

[0046] NMR analysis product: 1H NMR (400MHz, CDCl3) δ [ppm] 8.05...

Embodiment 3

[0048] In this embodiment, the structural formula of the thermally activated delayed fluorescent material BP-DPAC is as follows:

[0049]

[0050] The synthetic route of the above-mentioned thermally activated delayed fluorescent material is as follows:

[0051]

[0052] The specific synthesis process is as follows:

[0053] Synthesis of BP-DPAC. 4-bromobenzophenone (0.055g, 0.21mmol), 9,10-dihydro-9,9-diphenylacridine (0.077g, 0.23mmol), tri-tert-butylphosphine tetrafluoroborate (0.02g), sodium tert-butoxide (0.2g) was added into a 100ml three-necked flask, vacuum replaced nitrogen three times, and 15ml of dried toluene was added. Stir at room temperature for 15min, add Pd 2 (dba) 3 (0.02g), stirred at 120°C for 18h. Cool to room temperature, pass through the elution column (eluted with DCM), spin dry, add silica gel powder to prepare a sample, and perform column chromatography separation. Reprecipitation with methanol gave 0.09 g of white solid (Y=83.5%).

[005...

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Abstract

The invention provides an acridine D-A type thermal activation delayed fluorescent material. The acridine D-A type thermal activation delayed fluorescent material contains similar electron-donating group acridine, the integrated structure of the material is changed by introducing different electron-withdrawing groups such as a benzene ring, fluorine, carbazole and sulphone, light emission with high purity and multiple colors, particularly blue color is realized, and the problems of shortage of the existing blue light thermal activation delayed fluorescent material and bad performance are solved. The material is novel in structure, has excellent performance, can be synthesized through Ullmann coupling reaction, is simple in synthesis method and high in yield, can serve as a light-emitting layer material in an organic electroluminescent device, has high light-emitting efficiency and low efficiency roll-off, and can effectively reduce lighting voltage.

Description

technical field [0001] The invention belongs to the technical field of luminescent materials, and in particular relates to an acridine D-A type thermally activated delayed fluorescent material, a preparation method and an application thereof. Background technique [0002] In recent years, organic light-emitting diodes (organic light-emitting diodes, OLEDs) have developed rapidly due to their unique structures and properties (light weight, bright colors, low power consumption, bendability, etc.). Electronic products such as TVs and smart phones using OLED as screens have been introduced to the market on a large scale, which means that OLED display technology is about to usher in a peak period of development. Although OLED has developed very rapidly in recent years, the technology has become more mature, and its market share has increased significantly, but the selection of luminescent materials has largely restricted the development of OLED. [0003] Luminescent materials ar...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D219/02C07D221/20C07D401/14C07D401/10C07D401/04C07D471/04C09K11/06H01L51/54H01L51/50
CPCC09K11/06C07D219/02C07D221/20C07D401/04C07D401/10C07D401/14C07D471/04C09K2211/1044C09K2211/1011C09K2211/1007C09K2211/1029H10K85/615H10K85/6572H10K50/11
Inventor 葛子义杨荣娟彭瑞祥张磊刘志洋雷涛李旺
Owner NINGBO INST OF MATERIALS TECH & ENG CHINESE ACADEMY OF SCI
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