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Thermal activation delayed fluorescence material based on dibenzothiophene sulfone

A technology of heat-activated delayed and fluorescent materials, applied in the direction of luminescent materials, organic chemistry, chemical instruments and methods, etc., can solve the problems of few types and low luminous efficiency

Pending Publication Date: 2021-09-24
XI AN JIAOTONG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the currently reported thermally activated delayed fluorescent materials have problems such as few types and low luminous efficiency, especially the low luminous efficiency of deep blue light / blue light thermally activated delayed fluorescent materials, usually not higher than 80%

Method used

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  • Thermal activation delayed fluorescence material based on dibenzothiophene sulfone
  • Thermal activation delayed fluorescence material based on dibenzothiophene sulfone
  • Thermal activation delayed fluorescence material based on dibenzothiophene sulfone

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0020] The target luminescent molecular structure of the present embodiment is

[0021] Refer figure 1 and figure 2 The synthesis route includes the following steps:

[0022] The first step: 9,9-dimethyl-9,10-dihydrridine (1 Equiv), 2-bromo-5-iodo (1 Equiv), copper iodide (0.02 equiv) and Sodium tert-butyl alcohol (2 equiv) is added to the reaction tube, and the nitrogen is drawn three times, and the mixture is stirred under nitrogen protection to add 50 ml of 1,4-dioxane (solvent). After the material is dissolved, 1,2-diaphrafonyl ring is added. Alkane (coordinator). The mixture was stirred at 110 ° C for 6 h. After cooling to room temperature, 100 ml of water was added to the reaction mixture and extracted with dichloromethane to obtain an organic layer. Finally, the organic layer was concentrated to obtain a crude product, separated by silica gel column chromatography to give a white solid product Y-BR with a yield of 70%.

[0023] Step 2: Y-BR (1 Equiv.), Combined boronic aci...

Embodiment 2

[0026] The target luminescent molecular structure of the present embodiment is:

[0027] Refer figure 1 and figure 2 The synthesis route includes the following steps:

[0028] The first step: Phenoxazine (1 Equivoxyl), 2-bromo-5-iodoenzene (1 Equiv.), Copper iodide (0.02 equiv.) And tert-butanol sodium (2 equiv.), The nitrogen was drawn three times, and 50 ml of 1,4-dioxane (coated 1,2-diaminocyclohexane) was added under nitrogen protection. The mixture was stirred at 110 ° C for 6 h. After cooling to room temperature, 100 ml of water was added to the reaction mixture and extracted with dichloromethane to obtain an organic layer. Finally, the organic layer was concentrated to obtain a crude product, separated by silica gel column chromatography to give a white solid product O-BR with a yield of 65%.

[0029] Step 2: O-BR (1 Equiv.), Which is the frequency of boronic acid-band, 1,1-di (diphenylphosphine) diomorite palladium (II) (0.02equiv. Potassium acetate (1.5 equiv.) Is dissol...

Embodiment 3

[0032] The target luminescent molecular structure of the present embodiment is:

[0033] Refer figure 2 The synthesis route includes the following steps:

[0034] Carbazole boric acid (2.3 equiv.), 4,6-dibromo-diphenylene-5,5-dioxide (1 Equiv), four (triphenylphosphine) palladium (0.1equiv), 50 ml of toluene And 25 ml of potassium carbonate (concentration of 2 mol / L) was stirred at 120 ° C for 24 h. After cooling to room temperature, 100 ml of water was added to the reaction mixture and extracted with dichloromethane to obtain an organic layer. Finally, the organic layer was concentrated to obtain a crude product, separated by silica gel column chromatography to obtain a target luminescent molecule 3, and the yield was 80%. The nuclear magnetic table data is: 1 H NMR (400MHz, CDCL 3 : δ (PPM) 8.15 (D, 4H), 7.99 (D, 4H), 7.94 (D, 2H), 7.78 (T, 2H), 7.72 (D, 4H), 7.58 (DD, 6H), 7.42 ( T, 4H), 7.29 (t, 4h).

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Abstract

The invention discloses a thermal activation delayed fluorescent material based on dibenzothiophene sulfone. The material has a chemical general formula disclosed in the invention, in the formula, a substituent group R1 is a hydrogen atom, an electron donor carbazole and a derivative thereof, phenoxazine and a derivative thereof, or acridine and a derivative thereof; a substituent R2 is a hydrogen atom, an electron donor carbazole and a derivative thereof, phenoxazine and a derivative thereof, or acridine and a derivative thereof; substituent groups R1 and R2 can be the same or different; according to the invention, the electron donor is introduced to the 4 and 6 sites of a dibenzothiophene sulfone group by using a chemical single bond, so that the molecular configuration of the fluorescence material can be optimized; by changing the type and the number of the electron donors, the light emitting color of the fluorescence material can be adjusted; the luminous efficiency of the fluorescence material can be enhanced by comprehensively utilizing the two means, so that the obtained fluorescence material has the thermal delay fluorescence characteristic, and meanwhile, the luminous quantum efficiency of the fluorescence material is remarkably improved to 95%.

Description

Technical field [0001] The present invention relates to the technical field of organic light-emitting materials, and more particularly to a type of thermally activated delayed fluorescent material based on diphenylgarneside. Background technique [0002] Organic light-emitting materials have important application value in the fields of electrolumubae, biodetes, and signal identity. In particular, the organic light-emitting diode prepared based on organic light-emitting materials is gradually applied to high-end display and solid state lighting equipment, and the related device has the advantages of color gamut, high contrast, and thin appearance, and even develop foldable. Curly Form of goods. At present, the organometallic complex in the precious metal ruthenium / platinum is one of the best luminescent materials for the preparation of high-efficiency organic light-emitting diodes. The reason is that the presence of heavy metal centers can promote the inter-line and utilization ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D409/10C07D409/14C07D413/10C07D413/14C09K11/06
CPCC07D409/14C07D413/14C07D409/10C07D413/10C09K11/06C09K2211/1029C09K2211/1033C09K2211/1092
Inventor 周桂江黎博琛杨晓龙孙源慧焦博
Owner XI AN JIAOTONG UNIV
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