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Purple fluorescent material crystal based on trifluoromethyl and preparation method

A trifluoromethyl, violet fluorescence technology, applied in the direction of luminescent materials, organic chemistry methods, chemical instruments and methods, etc., can solve the problem of not many, violet fluorescent material crystals are rare, etc., to achieve small energy level difference, easy to large The effect of large-scale preparation and short material synthesis route

Inactive Publication Date: 2018-03-02
SOUTHEAST UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

So far, there are not many types of violet fluorescent materials, and a large number of violet fluorescent materials with excellent performance have yet to be designed and synthesized, and reports on crystals of violet fluorescent materials are even rarer.

Method used

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  • Purple fluorescent material crystal based on trifluoromethyl and preparation method
  • Purple fluorescent material crystal based on trifluoromethyl and preparation method
  • Purple fluorescent material crystal based on trifluoromethyl and preparation method

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0024] Embodiment 1: Preparation of 9-[3,5 bis(trifluoromethyl)phenyl]-9H-carbazole

[0025] Add 1-bromo-3,5-bis(trifluoromethyl)benzene 2.91g (10mmol), carbazole 1.80g (10.8mmol), cuprous iodide 0.19g (1mmol), anhydrous potassium carbonate 2.72g (20mmol ), 0.2 g (1 mmol) of 1,10-phenanthroline monohydrate and 73 g (1 mol) of N, N-dimethylformamide were mixed uniformly, and reflux reaction was carried out under nitrogen protection for 40 h. The reaction solution was cooled to room temperature, poured into 100 g of water to precipitate a solid, and after suction filtration, the filter cake was made into sand and subjected to column chromatography, and eluted with petroleum ether with a boiling range of 60-90°C to obtain a white solid with a yield of 63.1%. 1 H NMR (300MHz, CDCl 3 )δ (ppm): 8.18 (d, J = 7.8Hz, 2H), 8.11 (s, 2H), 7.99 (s, 1H), 7.50 (t, J = 7.2Hz, 6.9Hz, 2H), 7.42-7.35 (m, 4H). 1 H NMR spectrum as image 3 shown.

Embodiment 2

[0026] Example 2: Preparation of 9-[3,5-bis(trifluoromethyl)phenyl]-9H-carbazole

[0027] Add 2.91g (10mmol) of 1-bromo-3,5-bis(trifluoromethyl)benzene, 1.67g (10mmol) of carbazole, 0.39g (2mmol) of cuprous iodide, and 2.04g (15mmol) of anhydrous potassium carbonate , 0.40 g (2 mmol) of 1,10-phenanthroline monohydrate and 36.5 g (0.5 mol) of N, N-dimethylformamide were mixed uniformly, and reflux reaction was carried out under nitrogen protection for 20 h. The reaction solution was cooled to room temperature, poured into 50 g of water to precipitate a solid, and after suction filtration, the filter cake was made into sand and subjected to column chromatography, and eluted with petroleum ether with a boiling range of 60-90°C to obtain a white solid with a yield of 53.9%. 1 H NMR (300MHz, CDCl 3 )δ (ppm): 8.18 (d, J = 7.8Hz, 2H), 8.11 (s, 2H), 7.99 (s, 1H), 7.50 (t, J = 7.2Hz, 6.9Hz, 2H), 7.42-7.35 (m, 4H). 1 H NMR spectrum as image 3 shown.

Embodiment 3

[0028] Example 3: Preparation of 9-[3,5-bis(trifluoromethyl)phenyl]-9H-carbazole

[0029] Add 2.91g (10mmol) of 1-bromo-3,5-bis(trifluoromethyl)benzene, 2.0g (12mmol) of carbazole, 0.19g (1mmol) of cuprous iodide, and 2.72g (20mmol) of anhydrous potassium carbonate , 0.20 g (1 mmol) of 1,10-phenanthroline monohydrate and 73 g (1 mol) of N, N-dimethylformamide were mixed uniformly, and refluxed for 20 h under the protection of nitrogen. The reaction solution was cooled to room temperature, poured into 100 g of water to precipitate a solid, and after suction filtration, the filter cake was made into sand and subjected to column chromatography, and eluted with petroleum ether with a boiling range of 60-90°C to obtain a white solid with a yield of 64.2%. 1 H NMR (300MHz, CDCl 3 )δ (ppm): 8.18 (d, J = 7.8Hz, 2H), 8.11 (s, 2H), 7.99 (s, 1H), 7.50 (t, J = 7.2Hz, 6.9Hz, 2H), 7.42-7.35 (m, 4H). 1 H NMR spectrum as image 3 shown.

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Abstract

The invention discloses a purple fluorescent material crystal based on trifluoromethyl and a preparation method of the purple fluorescent material crystal. The material is 9-[3,5bis(trifluoromethyl)phenyl]-9H-carbazole with a structure shown as a formula (I) in the description. Crystallization is performed through a mixed solvent of ethanol and dichloromethane; white needle-like crystals of the material are respectively obtained; a single crystal structure of the material is an orthorhombic crystal system; crystal axes are shown in the description; an included angle alpha between crystal surfaces is 90.00 degrees, an included angle beta between the crystal surfaces is 90.00 degrees, and an included angle gamma between the crystal surfaces is 90.00 degrees. The purple fluorescent material crystal based on the trifluoromethyl has the advantages that the preparation method is simple; the purple light emission is realized; the singlet state-triplet state energy level difference is small; the purple fluorescent material crystal can be used as a purple delay fluorescent material in an electrofluorescence device luminous layer.

Description

technical field [0001] The invention belongs to the technical field of organic light-emitting materials, and in particular relates to a trifluoromethyl-based purple fluorescent material crystal and a preparation method thereof. Background technique [0002] Violet fluorescent materials have very broad application prospects in the fields of flat panel display and information storage. [0003] Compared with red, green, and blue fluorescent materials, purple fluorescent materials require strict control of the degree of molecular conjugation due to the high requirements for molecular design. So far, there are not many types of violet fluorescent materials, and a large number of violet fluorescent materials with excellent performance have yet to be designed and synthesized, and reports on crystals of violet fluorescent materials are rare. Currently reported purple fluorescent materials mainly include diphenyl sulfone derivatives (Ye J et al. Chemistry of Materials, 2013, 25: 263...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D209/86C09K11/06H01L51/50H01L51/44
CPCC09K11/06C07D209/86C07B2200/13C09K2211/1029C09K2211/1007H10K85/6572H10K50/11Y02E10/549
Inventor 黄斌蒋伟汪洋洋朱佳磊孙岳明林保平
Owner SOUTHEAST UNIV
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