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Spirofluorene benzyl fluorescent material

A technology based on phenyl and aryl groups, applied in the field of organic electroluminescence display, can solve the problems of difficulty in improving luminous efficiency and small luminous contribution

Inactive Publication Date: 2016-04-06
SHIJIAZHUANG CHENGZHI YONGHUA DISPLAY MATERIALS CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Usually, the generation ratio of singlet excitons and triplet excitons is 1:3, and according to the prohibition effect of quantum statistics, triplet excitons mainly undergo non-radiative attenuation, which contributes very little to luminescence, and only singlet excitons Therefore, for organic / polymer electroluminescent devices, the fundamental reason why the luminous efficiency is difficult to improve is that the luminescence process is the luminescence of singlet excitons

Method used

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  • Spirofluorene benzyl fluorescent material
  • Spirofluorene benzyl fluorescent material
  • Spirofluorene benzyl fluorescent material

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0079] The preparation of embodiment 1 compound I001

[0080]

[0081] The first step: the preparation of 2-bromo-4,4'-dimethylbiphenyl (I-1)

[0082]

[0083] Dissolve 36.5g (0.2mol) of 4,4'-dimethylbiphenyl in 360ml of anhydrous dichloromethane, add 1 grain of iodine at room temperature, stir for 1 hour, slowly add 35.2g (0.22mol) of bromine dropwise The solution dissolved in dichloromethane was stirred and reacted for 24 hours, 120ml of saturated aqueous sodium bisulfite solution was added, stirred and reacted for 1 hour, the organic phase was separated, the organic phase was dried with anhydrous sodium sulfate, filtered, and the filtrate was concentrated to dryness under reduced pressure , separated and purified with a silica gel column, and concentrated to dryness under reduced pressure to obtain 48 g of I-1 as a colorless oil, with a yield of 92%.

[0084] The second step: the preparation of intermediate I-2

[0085]

[0086] Stir and dissolve 20g of intermedi...

Embodiment 2

[0105] The preparation of embodiment 2 compound I017

[0106]

[0107] The first step: the preparation of intermediate I-4

[0108]

[0109] Under the protection of nitrogen, 10.4g of the intermediate I-3 prepared in Example 1 was dissolved in 120ml of dry tetrahydrofuran, placed in a low-temperature tank and cooled to -78°C, and 20ml of 2.5M n-butyllithium-hexane solution was added dropwise , stirred and reacted for 30 minutes, added dropwise a solution of 9.2g of N,N-diethylbenzamide dissolved in tetrahydrofuran, stirred and reacted for 30 minutes, raised to room temperature and stirred for 1 hour, added 100ml of 3M dilute hydrochloric acid aqueous solution, stirred and reacted 1 hour. Extract three times with ethyl acetate. The organic phases were combined and washed with 100ml of saturated brine, the organic phase was dried with anhydrous sodium sulfate, filtered, the filtrate was concentrated to dryness under reduced pressure, the residue was separated and purifie...

Embodiment 3

[0122] The preparation of embodiment 3 compound I051

[0123]

[0124] The first step: the preparation of intermediate I-4

[0125]

[0126] Under nitrogen protection, 10.0g of the intermediate I-3 prepared in Example 1 was dissolved in 120ml of dry N,N-dimethylformamide, 5.5g of thiophenol and 13.0g of anhydrous cesium carbonate were added and 38mg of cuprous iodide, stirred and reacted for 30 minutes, then added 0.5ml of N,N'-dimethylethylenediamine, heated to 100°C, stirred and reacted for 12 hours, cooled to room temperature, poured the reaction solution into 500ml of dilute In aqueous hydrochloric acid solution, stirred and reacted for 1 hour, filtered, washed the filter cake with water, and recrystallized with dichloromethane-ethanol to obtain 9.3 g of an intermediate, a yellow solid, with a yield of 84%.

[0127] The above intermediate of 9.3g was dissolved in 150ml of dichloromethane, 19g of m-chloroperoxybenzoic acid (75%) was added in batches, stirred and reac...

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Abstract

The invention discloses a luminescent material with a spirofluorene benzyl unit. 9,9'-spirobifluorene molecules are taken as a main body to prepare a series of luminescent materials (see general formula I) by connection with different substituent groups. The compound provided by the invention has the characteristics of high glass transition temperature, high triplet state energy level, high quantum efficiency and the like, and can be applied to organic electroluminescent LEDs to serve as a luminescent material. Moreover, raw materials are easily available, the preparation is simple and convenient, the overall yield is high, and the cost of the luminescent material is greatly reduced.

Description

technical field [0001] The invention belongs to the field of organic electroluminescence display and relates to a series of spirofluorene benzyl fluorescent materials. Background technique [0002] Organic electroluminescence (referred to as OLED) and related research As early as 1963, pope et al. first discovered the electroluminescence phenomenon of organic compound single crystal anthracene. In 1987, Kodak Corporation of the United States made an amorphous film device by evaporating organic small molecules, which reduced the driving voltage to less than 20V. This type of device is ultra-thin, fully cured, self-illuminating, high brightness, wide viewing angle, fast response speed, low driving voltage, low power consumption, bright color, high contrast, simple process, good temperature characteristics, and can realize flexible display. And other advantages, can be widely used in flat panel displays and surface light sources, so it has been widely researched, developed and...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D209/82C07C255/58C07D213/74C07D307/91C07D333/76C07D235/04C07D209/12C07D471/04C07D207/323C07D219/02C07D265/38C07D279/22C07C317/14C07D417/14C09K11/06H01L51/50H01L51/54
CPCC07C255/58C07D209/12C07D209/82C07D213/74C07D235/04C07D307/91C07D333/76C07D471/04C09K2211/1051C09K2211/1044C09K2211/1037C09K2211/1033C09K2211/1029C09K2211/1014C09K2211/1092C09K2211/1088H10K85/624H10K85/653H10K85/6576H10K85/6574H10K85/657H10K85/6572H10K50/00H10K50/11
Inventor 曹建华
Owner SHIJIAZHUANG CHENGZHI YONGHUA DISPLAY MATERIALS CO LTD
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