Aggregation-induced light emission red delay material, preparation method and application thereof

An aggregation-induced luminescence, red technology, applied in the direction of luminescent materials, preparation of organic compounds, chemical instruments and methods, etc., can solve the problems of fluorescence quenching, device efficiency roll-off, long fluorescence lifetime, etc., achieve short synthesis route, reduce Lighting up voltage, cheap and easy-to-obtain raw materials

Inactive Publication Date: 2017-02-01
JIANGSU INSTITUTE OF EDUCATION
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, due to the long fluorescence lifetime of thermally activated delayed fluorescent materials, fluorescence quenching is prone to occur in the device, resulting in a roll-off of device efficiency.

Method used

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  • Aggregation-induced light emission red delay material, preparation method and application thereof
  • Aggregation-induced light emission red delay material, preparation method and application thereof
  • Aggregation-induced light emission red delay material, preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0044] Preparation of 2-carbazol-9-yl-anthraquinone

[0045]In a 100mL three-necked flask, add 2-bromoanthraquinone (3.45g, 12mmol), carbazole (2.00g, 12mmol), cuprous iodide (0.23g, 1.2mmol), 1,10-phenanthroline monohydrate (0.24g, 1.2mmol), anhydrous potassium carbonate (2.45g, 18mmol), and 18.5mL N,N-dimethylformamide were mixed evenly, and refluxed for 20 hours under nitrogen protection. The reaction solution was cooled to room temperature, and 50mL water, and then extracted with dichloromethane (2*100 mL), the organic layers were combined, dried over anhydrous sodium sulfate and concentrated to give a brown oil. After column chromatography, eluting with a mixture of dichloromethane and petroleum ether at a volume ratio of 1:5, a red solid 2-carbazol-9-yl-anthraquinone was obtained, and the prepared 2-carbazole-9 The yield of -yl-anthraquinone is 65.7%. 1 H NMR (300MHz, CDCl 3 )δ, (ppm): 8.56-8.76 (d, 2H), 8.37-8.46 (t, 2H), 8.17-8.19 (d, 2H), 8.07-8.10 (m, 1H), 7.86-7....

Embodiment 2

[0047] Preparation of 2-carbazol-9-yl-anthraquinone

[0048] In a 100mL three-necked flask, add 2-bromoanthraquinone (3.45g, 12mmol), carbazole (2.00g, 12mmol), cuprous iodide (0.35g, 1.83mmol), 1,10-phenanthroline monohydrate (0.35g, 1.77mmol), anhydrous potassium carbonate (3.28g, 24mmol), 40mLN, N-dimethylformamide were mixed uniformly, and reflux reaction was carried out under nitrogen protection for 24 hours, the reaction solution was cooled to room temperature, and 50mL of water was added, Then it was extracted with ethyl acetate (2*100 mL), the organic layers were combined, dried over anhydrous sodium sulfate and concentrated to obtain a brown oil. After column chromatography, eluting with a mixture of dichloromethane and petroleum ether at a volume ratio of 1:10, a red solid 2-carbazol-9-yl-anthraquinone was obtained, and the prepared 2-carbazole-9 The yield of -yl-anthraquinone was 72.3%. 1 H NMR (300MHz, CDCl 3 )δ, (ppm): 8.56-8.76 (d, 2H), 8.37-8.46 (t, 2H), 8.17...

Embodiment 3

[0050] In a 100mL three-necked flask, add 2-bromoanthraquinone (3.45g, 12mmol), carbazole (2.40g, 14.4mmol), cuprous iodide (0.46g, 2.4mmol), 1,10-phenanthroline monohydrate Compound (0.484g, 2.4mmol), anhydrous potassium carbonate (3.28g, 24mmol), 46mL N, N-dimethylformamide were mixed evenly, and the reaction was refluxed under nitrogen protection for 40 hours. The reaction solution was cooled to room temperature, 50 mL of water was added, and then extracted with dichloromethane (2*100 mL), the organic layers were combined, dried over anhydrous sodium sulfate and concentrated to obtain a brown oil. After column chromatography, eluting with a mixture of dichloromethane and petroleum ether at a volume ratio of 1:20, a red solid 2-carbazol-9-yl-anthraquinone was obtained, and the prepared 2-carbazole-9 The yield of -yl-anthraquinone was 68.7%. 1 H NMR (300MHz, CDCl 3 )δ, (ppm): 8.56-8.76 (d, 2H), 8.37-8.46 (t, 2H), 8.17-8.19 (d, 2H), 8.07-8.10 (m, 1H), 7.86-7.91 (m, 2H ), 7....

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Abstract

The invention relates to an aggregation-induced light emission red delay material which is composed of an electron withdrawing group anthraquinone and an electron-donating group carbazole or triphenylamine. The material is represented as the structure formula (I), wherein R1 is the carbazole or triphenylamine and is particularly represented as the following structure. The aggregation-induced light emission red delay material has short synthetic route and simple synthetic method, is prepared from easy-to-obtain raw materials, and is suitable for wide application. A red light device prepared from the material as a luminescent layer has high brightness, high efficiency, and low turn-on voltage, and can be widely applied in the field of organic electroluminescence.

Description

technical field [0001] The invention belongs to the field of luminescent materials, and in particular relates to an aggregation-induced luminescent red retardation material, a preparation method and an application. Background technique [0002] In electroluminescent devices, the light-emitting layer is a key factor affecting device performance. In the first generation of electroluminescent devices, traditional fluorescent materials are used in the light-emitting layer. Since fluorescent materials can only use 25% of singlet excitons in theory, the maximum internal quantum efficiency is only 25%, and the device efficiency is not high; In the second-generation electrophosphorescent device, the light-emitting layer adopts the structure of the host-guest light-emitting system, that is, the host-guest light-emitting material is doped with the guest light-emitting material (usually a noble metal complex), and the complex uses platinum, iridium and other noble metal elements, It p...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C09K11/06C07D209/86C07C221/00C07C225/26H01L51/54
CPCC09K11/06C07C221/00C07D209/86C09K2211/1029C09K2211/1014H10K85/631H10K85/6572C07C225/26
Inventor 黄斌季益刚李紫荆戚嘉敏周娜吴丽君时智慧徐俊宝伍蓉
Owner JIANGSU INSTITUTE OF EDUCATION
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