Thermally activated delayed fluorescent material, organic electroluminescent device and application of thermally activated delayed fluorescent material

A kind of compound, the technology of compound of general formula, applied in the field of organic electron light-emitting device

Pending Publication Date: 2021-12-17
BEIJING ETERNAL MATERIAL TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The researchers proposed a method of using triplet exciton quenching to generate singlet excitons in fluorescent devices to improve the efficiency of fluorescent devices, but the theoretical maximum external quantum efficiency of this method is only 62.5%, which is far lower than that of phosphorescence. Material

Method used

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  • Thermally activated delayed fluorescent material, organic electroluminescent device and application of thermally activated delayed fluorescent material
  • Thermally activated delayed fluorescent material, organic electroluminescent device and application of thermally activated delayed fluorescent material
  • Thermally activated delayed fluorescent material, organic electroluminescent device and application of thermally activated delayed fluorescent material

Examples

Experimental program
Comparison scheme
Effect test

Synthetic example 1

[0080] Synthesis Example 1: Synthesis of S1

[0081]

[0082] Synthesis of Intermediate S1-1:

[0083]Add carbazolospirofluorene (14.54g, 35.85mmol), 2,6-dibromo-4-fluorobenzonitrile (10g, 35.85mmol), cesium carbonate (23.36g, 71.71mmol) into a 500ml single-necked bottle at room temperature, N,N-Dimethylformamide (200ml) was reacted overnight at 120°C under nitrogen protection. Stop heating, after cooling to room temperature, add 500ml of water and stir for 10min, a large amount of white solid precipitates, filter with suction, wash the filter cake with ethanol for 2h, cool down and filter with suction to obtain 18g of white solid product, yield 75.6%. Molecular ion mass determined by mass spectrometry: 664.34 (theoretical value: 664.40).

[0084] Synthesis of Compound S1:

[0085] At room temperature, S1-1 (5g, 7.53mmol), carbazole (2.52g, 12.05mmol), Pd 2 (dba) 3 (0.69g, 0.75mmol), P(t-Bu) 3 (0.30g, 1.51mmol), sodium tert-butoxide (2.17g, 22.58mmol), and xylene (...

Synthetic example 2

[0086] Synthesis Example 2: Synthesis of S2

[0087]

[0088] Synthesis of compound S2:

[0089] At room temperature, S1-1 (5g, 7.53mmol), 3,6-dimethylcarbazole (2.94g, 15.05mmol), Pd 2 (dba) 3 (0.69g, 0.75mmol), P(t-Bu) 3 (0.30g, 1.51mmol), sodium tert-butoxide (2.17g, 22.58mmol), and xylene (50ml) were added to a 100ml single-necked bottle, pumped with nitrogen three times, and heated to 130°C to react overnight. The reaction solution was lowered to room temperature, filtered, and the filtrate was concentrated by mixing silica gel. Column chromatography (PE: EA = 100:1) gave 5 g of crude product. Toluene / ethanol recrystallization gave 4 g of white solid, yield 59.5%. Molecular ion mass determined by mass spectrometry: 864.44 (theoretical value: 864.33).

Synthetic example 3

[0090] Synthesis Example 3: Synthesis of S4

[0091]

[0092] Synthesis of compound S4:

[0093] At room temperature, S1-1 (5g, 7.53mmol), 3-isopropylcarbazole (3.78g, 15.05mmol), Pd 2 (dba) 3 (0.69g, 0.75mmol), P(t-Bu) 3 (0.30g, 1.51mmol), sodium tert-butoxide (2.17g, 22.58mmol), and xylene (50ml) were added to a 100ml single-necked bottle, pumped with nitrogen three times, and heated to 130°C to react overnight. The reaction solution was lowered to room temperature, filtered, the filtrate was concentrated by mixing silica gel, column chromatography (PE:EA=100:1) obtained 5.2 g of crude product, recrystallized from toluene / ethanol to obtain 4.5 g of white solid, yield 46.7%. Molecular ion mass determined by mass spectrometry: 920.41 (theoretical value: 920.39).

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Abstract

The invention relates to the technical field of organic electroluminescence, in particular to an organic compound and application thereof. The compound has a structure as shown in a formula (1) (See the specification), wherein D1 is selected from the structure as shown in the formula (I), and D2 is selected from the structure as shown in a general formula (II). When the compound is used as an OLED device, the efficiency of the device can be effectively improved, and the driving voltage can be reduced. The compound is a light-emitting material with good performance.

Description

technical field [0001] The invention relates to the technical field of organic electroluminescent materials, in particular to a compound, a thermally activated delayed fluorescent material, an organic electroluminescent device containing the same and applications thereof. Background technique [0002] Under electro-excited conditions, organic electroluminescent devices will generate 25% singlet and 75% triplet excitons. The traditional fluorescent materials can only use 25 singlet excitons due to the spin-forbidden reason, so the external quantum efficiency is only limited within 5%. Almost all triplet excitons can only be lost as heat. To improve the efficiency of organic electroluminescent devices, triplet excitons must be fully utilized. [0003] To this end, researchers have proposed a number of methods, most notably the use of phosphorescent materials. Due to the introduction of heavy atoms, phosphorescent materials have a spin-orbit coupling effect, which can make f...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D209/96C07D471/04C07D519/00C09K11/06H01L51/50H01L51/54
CPCC07D209/96C07D471/04C07D519/00C09K11/06C09K2211/1029C09K2211/1014C09K2211/1007C09K2211/1044H10K85/631H10K85/6572H10K50/121H10K50/11
Inventor 孙磊魏金贝李熠烺李国孟
Owner BEIJING ETERNAL MATERIAL TECH
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