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A thermally activated delayed fluorescent material and electroluminescent device

An electroluminescent device, thermal activation delay technology, applied in luminescent materials, electro-solid devices, electrical components, etc., can solve the problem of low luminous efficiency of thermally activated delayed fluorescent materials, and achieve effective regulation of luminescence performance, enhanced interaction, Effects of Nonradiative Transition Suppression

Active Publication Date: 2022-06-03
SHENZHEN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] In view of the above deficiencies in the prior art, the object of the present invention is to provide a thermally activated delayed fluorescent material and an electroluminescent device, aiming at solving the problem of low luminous efficiency of thermally activated delayed fluorescent material

Method used

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  • A thermally activated delayed fluorescent material and electroluminescent device
  • A thermally activated delayed fluorescent material and electroluminescent device
  • A thermally activated delayed fluorescent material and electroluminescent device

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0037] The preparation method of compound 11 comprises the following steps:

[0038] 1), the preparation reaction formula of intermediate 11-1 is as follows:

[0039]

[0040] Prepare a 25mL dry round-bottomed flask, add 4-bromodiphenyl sulfoxide (1.12g, 4.0mmol), sodium azide (0.31g, 4.8mmol) and 8mL chloroform at a temperature of 0 °C, add dropwise 1.60 mL of concentrated sulfuric acid was added, and the mixture was heated at 45 °C and stirred for 12 h. After the 4-bromodiphenyl sulfoxide was completely reacted, it was cooled to room temperature, the reaction was quenched with water, the organic layer was extracted with chloroform, washed with salt, the organic layer was dried with anhydrous sodium sulfate, filtered and concentrated, and the crude product was passed through the column layer Further purification by analytical column chromatography gave a colorless solid, intermediate 11-1 (0.83 g, 2.8 mmol), with HPLC purity of 99.3% and yield of 70%. MS(MALDI-TOF): m / z ...

Embodiment 2

[0048] The preparation method of compound 15 comprises the following steps:

[0049] 1), the preparation reaction formula of intermediate 15-1 is as follows:

[0050]

[0051] In a 50 mL round-bottomed flask was added 4-bromodiphenyl sulfoxide (1.13 g, 4.0 mmol, 1.0 equiv.), PhI(OAc) 2 (3.87 g, 12.0 mmol, 3.0 equiv.), ammonium carbamate (1.25 g, 16.0 mmol, 4.0 equiv.) and methanol (8.0 mL), stirred openly at room temperature for 30 min and removed the solvent by rotary evaporation. The crude product was subjected to column chromatography Purification and drying in vacuo gave a colorless solid, Intermediate 15-1 (0.83 g, 2.80 mmol), HPLC purity 99.2%, yield 70%. MS(MALDI-TOF): m / z 294.9[M + ].

[0052] 2), the preparation reaction formula of intermediate 15-2 is as follows:

[0053]

[0054] Intermediate 15-1 (0.75g, 3.0mmol), triethylamine (0.68mL, 0.83g, 5.2mmol) and 50mL of dichloromethane were added to a 150mL single-neck round bottom flask, dissolved, cooled in a...

Embodiment 3

[0059] The preparation method of compound 45 comprises the following steps:

[0060] 1), the preparation reaction formula of intermediate 45-1 is as follows:

[0061]

[0062]2-Bromodibenzothiophene (2.62g, 10.0 mmol), iodobenzenediacetic acid (16.10g, 50.0mmol, 5equiv.), ammonium carbonate (2.88g, 30.0mmol, 3equiv.) were successively added to a 250mL single-necked round bottom flask. ) and 80 mL of methanol, the above mixture was stirred at room temperature for 48 hours. The solvent was removed by rotary evaporation, purified by column chromatography, and dried in vacuo to obtain 2.40 g (8.20 mmol) of a colorless solid with HPLC purity of 99.5% and yield of 82%. MS(MALDI-TOF): m / z 293.0[M + ].

[0063] 2), the preparation reaction formula of intermediate 45-2 is as follows:

[0064]

[0065] Intermediate 45-1 (0.75g, 2.6mmol), dissolved in 50mL dichloromethane, diphenylphosphine chloride (1.21g, 0.98mL, 5.2mmol) and pyridine (0.41mL) were added to a 150mL single-nec...

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PUM

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Abstract

The present invention provides a thermally activated delayed fluorescent material and an electroluminescent device. The thermally activated delayed fluorescent material has the following structure: the molecular structure of the thermally activated delayed fluorescent material provided by the present invention is a donor-acceptor type molecule, wherein, The electron-deficient acceptor contains a sulfoximine group, which is connected with a nitrogen-containing heterocyclic electron donor, and forms a small Singlet-triplet energy level difference; In addition, due to the enhanced intramolecular and / or intermolecular interactions of the sulfoximine group, the molecular rigidity increases, the non-radiative decay rate decreases, and the luminous efficiency increases; the introduction of different The electron-withdrawing functional group to the electron-deficient sulfoximine N substitution position is simple to synthesize and has various forms, which can effectively control the luminescent properties of TADF materials.

Description

technical field [0001] The invention relates to the field of organic electroluminescent materials, in particular to a thermally activated delayed fluorescent material and an electroluminescent device. Background technique [0002] Organic light-emitting diodes (OLEDs) have the characteristics of self-luminescence, short response time, wide operating temperature range, low driving voltage, low energy consumption, light weight and high flexibility. Lighting, flexible display, transparent display and other aspects have broad application prospects, so they have attracted much attention from domestic and foreign scientific and technological circles and industries. [0003] It is generally believed that the ratio of electrons and holes injected into organic materials to form singlet and triplet excitons is 1:3, and electrons in the triplet state cannot transition back to the ground state due to the conservation of spin angular momentum, so the maximum internal quantum of OLED is ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D219/02C07F7/10C07D401/12C07D401/14C07D409/04C07D409/14C07F9/64C07F9/6568C07F9/6558C07D495/04C07D495/14C07D411/04C07D411/14C07F9/6561C07F7/08C07D417/04C07D417/10C07D513/14C07D265/38C07D413/12C07D413/14C07F9/6533C07F9/6544C07D293/10C07D421/04C07D491/052C07D513/16C07D209/86C07C381/10C09K11/06H01L51/50H01L51/54
CPCC07D219/02C07F7/10C07D401/12C07D401/14C07D409/04C07D409/14C07F9/64C07F9/65681C07F9/65586C07D495/04C07D495/14C07D411/04C07D411/14C07F9/6561C07F7/0816C07D417/04C07D417/10C07D513/14C07D265/38C07D413/12C07D413/14C07F9/65335C07F9/6547C07D293/10C07D421/04C07D491/052C07D513/16C07D209/86C07C381/10C09K11/06C09K2211/1029C09K2211/1092C09K2211/1051C09K2211/1037C09K2211/1033C09K2211/1096H10K85/631H10K85/654H10K85/657H10K85/6572H10K85/40H10K50/11Y02B20/30
Inventor 曹啸松曾洋杨楚罗
Owner SHENZHEN UNIV
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