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Enaminone boron complex fluorescent material as well as preparation method and application thereof

A technology of enaminone boron and fluorescent materials, applied in luminescent materials, chemical instruments and methods, compounds containing elements of group 3/13 of the periodic table, etc., can solve the problems of limited electron-pulling ability and luminescence limitation, and achieve high The effect of external quantum efficiency and good application prospects

Pending Publication Date: 2022-08-05
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, due to the limited electron-withdrawing ability of tricoordinate boron complexes such as triarylboron, the luminescence of TADF materials based on tricoordinate boron complexes is mostly limited to blue and green light.

Method used

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  • Enaminone boron complex fluorescent material as well as preparation method and application thereof
  • Enaminone boron complex fluorescent material as well as preparation method and application thereof
  • Enaminone boron complex fluorescent material as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0038] Embodiment 1: an enaminone boron complex thermally activated delayed fluorescent material with a structure of C1, the synthetic route is as follows:

[0039]

[0040] (1) Synthesis of intermediates with structure 1: in an inert atmosphere, Z-1-(4-bromophenyl)-3-(anilino)propenone (3.0 mmol, 0.90 g), 9,10-di Hydrogen-9,9-dimethylacridine (4.5mmol, 0.94g), tris(dibenzylideneacetone)dipalladium (Pd 2 (dba) 3 , 0.15mmol, 137mg), tri-tert-butylphosphine tetrafluoroborate ((t-Bu) 3 PH-BF 4 , 1.2mmol, 348mg) and sodium tert-butoxide (9.0mmol, 0.86g) were added to a 250mL two-necked flask, and then the reaction system was pumped and ventilated three times. After that, 80 mL of anhydrous toluene solvent was introduced into the reaction system, and finally the reaction system was heated to 95° C. and reacted at this temperature for 12 h. The reaction was stopped after the disappearance of the raw materials was detected by TLC plate. After cooling the reaction system to ro...

Embodiment 2

[0042] Embodiment 2: a thermally activated delayed fluorescent material of an enaminone boron complex with a structure of C2, the synthetic route is as follows:

[0043]

[0044] (1) Synthesis of intermediates with structure 2: In an inert atmosphere, Z-1-(4-bromophenyl)-3-(4-cyanoanilino)propenone (3.0 mmol, 0.98 g), 9 , 10-dihydro-9,9-dimethylacridine (4.5mmol, 0.94g), tris(dibenzylideneacetone)dipalladium (Pd 2 (dba) 3 , 0.15mmol, 137mg), tri-tert-butylphosphine tetrafluoroborate ((t-Bu) 3 PH-BF 4 , 1.2mmol, 348mg) and sodium tert-butoxide (9.0mmol, 0.86g) were added to a 250mL two-necked flask, and then the reaction system was pumped and ventilated three times. After that, 80 mL of anhydrous toluene solvent was introduced into the reaction system, and finally the reaction system was heated to 95° C. and reacted at this temperature for 12 h. The reaction was stopped after the disappearance of the raw materials was detected by TLC plate. After cooling the reaction sys...

Embodiment 3

[0046] Embodiment 3: a kind of structure is C3 enamino ketone boron complex fluorescent material, the synthetic route is as follows:

[0047] Intermediate 2 was synthesized according to step (1) in Example 2.

[0048] Synthesis of C3: The raw material intermediate 2 (1 mmol, 0.46 g) and tris(4-fluorophenyl) boron (1.5 mmol, 0.44 g) were added to a 250 mL round-bottomed flask, and argon was replaced under vacuum, and then anhydrous toluene was introduced 60 mL, the reaction body was reacted at 110 °C overnight. After the reaction, the solvent was spin-dried, and 0.47 g of solid was obtained by silica gel column separation, and the yield was 70%. MALDI-TOF MS: Calculated: 655.3 [M] + , measured value: 655.2[M] + .

[0049]

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Abstract

The invention relates to an enaminone boron complex fluorescent material as well as a preparation method and application thereof, and belongs to the technical field of organic luminescent materials. The structure of the enaminone boron complex fluorescent material is shown as a formula 1, and the enaminone boron complex fluorescent material is composed of a ligand on a boron atom of an enaminone boron complex, an aryl group, a heteroaryl group or a fused heterocyclic group connected to a nitrogen atom of the enaminone boron complex, and an aryl group, a heteroaryl group or a fused heterocyclic group connected to a carbon atom adjacent to an oxygen atom of the enaminone boron complex. An enaminone boron complex is used as an acceptor and is combined with an electron donor unit to form a donor-acceptor structure, and an electron withdrawing structural unit is introduced to one side of an enaminone nitrogen atom, so that the LUMO energy level is effectively regulated and controlled, and the material has the characteristics of red light emission and thermal activation delayed fluorescence. The enaminone boron complex fluorescent material disclosed by the invention is used for constructing a luminescent layer of an organic electroluminescent device, can realize red light emission with relatively high external quantum efficiency, and can be applied to organic electroluminescent display.

Description

technical field [0001] The invention relates to the technical field of organic light-emitting materials, in particular to an enaminone boron complex fluorescent material and a preparation method and application thereof. Background technique [0002] Compared with traditional display technologies, organic light-emitting diodes (OLEDs) have the advantages of self-luminescence, high contrast, low energy consumption, light weight, fast response speed, and the ability to prepare flexible large-area devices. and other fields have broad application prospects. OLED light-emitting devices are usually composed of electrode material film layers and organic functional layers sandwiched between two electrode film layers, including hole injection layer, hole transport layer, light-emitting layer, hole blocking layer, electron transport layer, electron injection layer. The mechanism of OLED light-emitting device is that a voltage is applied between two electrodes. Under the action of an ...

Claims

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Application Information

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IPC IPC(8): C07F5/02C09K11/06H01L51/54
CPCC07F5/02C09K11/06C09K2211/1029C09K2211/1096C09K2211/104H10K85/657H10K85/6572Y02E10/549
Inventor 王利祥童辉吴晓甫栗华
Owner CHANGCHUN INST OF APPLIED CHEMISTRY - CHINESE ACAD OF SCI
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