Series of fluorescent OLED materials

A C6-C60, unsubstituted technology used in the field of organic electroluminescence display

Inactive Publication Date: 2016-04-13
SHIJIAZHUANG CHENGZHI YONGHUA DISPLAY MATERIALS CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the reported thermally activated delayed fluorescence materials can only be prepared by doping due to the aggregation fluorescence quenching effect in the solid state.

Method used

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  • Series of fluorescent OLED materials
  • Series of fluorescent OLED materials
  • Series of fluorescent OLED materials

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0088] Embodiment 1, the preparation of compound formula 17

[0089]

[0090] Step 1: Preparation of 2-bromo-4,4’-dimethylbiphenyl

[0091]

[0092] 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 by silica gel column, and concentrated to dryness under reduced pressure to obtain 48 g of a colorless oil, with a yield of 92%.

[0093] The second step: the preparation of 2-bromo-4,4'-dibromomethylenebiphenyl

[0094]

[0095] Dissolve 46g (0.176mol) of 2-bromo-...

Embodiment 2

[0113] Embodiment 2, the preparation of compound formula 55

[0114]

[0115] The first step: the preparation of compound formula 20

[0116]

[0117] The synthesis operation of this step refers to the fifth step of Example 1, using 10g (16.9mmol) 2-bromo-4,4'-bis(2,2-stilbene)biphenyl and 8.5g (20mmol) 3,5- Diphenyl-4-(4-(boronic acid pinacol ester) phenyl)-4H-1,2,4-triazole was subjected to a coupling reaction, separated and purified on a silica gel column to obtain 5.8 g of a yellow solid, Yield 80%.

[0118] The second step: intermediate 4-(4",5'-bis(1-bromo-2,2-distyryl)-[1,1':2',1"-triphenyl]-4- The preparation of -3,5-diphenyl-4H-1,2,4-triazole

[0119]

[0120] The compound formula 20 of 5g (6.2mmol) is mixed with 250ml carbon tetrachloride, adds the free radical initiator AIBN of the NBS of 2.4g (13.6mmol) and 10mg (0.06mmol), is warming up to reflux stirring reaction 24 hours, is cooled to room temperature , add 100ml of water to dilute, heat up to reflu...

Embodiment 3

[0132] Embodiment 3, the preparation of compound formula 95

[0133]

[0134] Step 1: Preparation of intermediate 9,9'-((2-bromo-[1,1'-biphenyl]-4,4'-diyl)bis(methylene))bis(9H-fluorene)

[0135]

[0136] Dissolve 20g (37.5mmol) of 2-bromo-4,4'-bis(phosphodiethylesterylmethylene)biphenyl in 100ml of dry tetrahydrofuran, add 13.5g (75mmol) of 9-fluorenone, and 10g (90mmol) of potassium tert-butoxide was added in batches, stirred for 8 hours, heated and refluxed for 4 hours, cooled to room temperature, poured into 500ml of ice water, extracted with ethyl acetate, and the organic phase was anhydrous sodium sulfate After drying and filtering, the filtrate was concentrated to dryness under reduced pressure, separated and purified by silica gel column, and eluted with petroleum ether to obtain 16.6 g of yellow solid with a yield of 75%.

[0137] The second step: the preparation of compound formula 95

[0138]

[0139] 10g (17mmol) of the upper step intermediate, 6.4g (20....

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Abstract

The invention discloses a series of fluorescent OLED materials, which have the structure as shown in a formula I. The materials shown in the formula I have delayed fluorescence property; the organic electroluminescent device prepared by utilizing the materials can obtain deep blue organic light emitting diodes, the noble metal phosphorescent materials can be replaced, the manufacturing cost of the OLED device is greatly lowered, the material synthesis and purification methods are suitable for large-scale production, and the materials are an ideal choice of a luminescent material of the organic electroluminescent device.

Description

technical field [0001] The invention belongs to the technical field of organic electroluminescence display and relates to a series of fluorescent OLED 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, 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 used. [00...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C49/784C07C317/14C07C255/50C07C255/51C07F9/53C07D333/76C07D335/16C07D279/34C07D207/323C07D241/12C07D241/24C07D241/42C07D249/08C07D235/08C07D487/04C07D271/107C07D271/06C07D239/26C07D251/24C07C15/52C07C25/24C09K11/06H01L51/54H01L51/50
CPCC09K11/06C07C15/52C07C25/24C07C49/784C07C255/50C07C255/51C07C317/14C07D207/323C07D235/08C07D239/26C07D241/12C07D241/24C07D241/42C07D249/08C07D251/24C07D271/06C07D271/107C07D279/34C07D333/76C07D335/16C07D487/04C07F9/53C09K2211/1092C09K2211/1088C09K2211/1059C09K2211/1048C09K2211/1044C09K2211/1029C09K2211/1014C09K2211/1011C09K2211/1007H10K85/649H10K85/654H10K85/655H10K85/656H10K85/6565H10K85/6572H10K85/6576H10K50/11
Inventor 曹建华
Owner SHIJIAZHUANG CHENGZHI YONGHUA DISPLAY MATERIALS CO LTD
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