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Bi(trimethylphenyl) boron derivatives and application thereof in white organic light-emitting diode

A technology of boron derivatives and trimethylbenzene, which is applied to bis(trimethylphenyl)boron derivatives and its application in white light organic electroluminescent diodes, and can solve the problem of non-luminescence mechanism and the like

Active Publication Date: 2014-07-02
TECHNICAL INST OF PHYSICS & CHEMISTRY - CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Because fluorescent materials can only utilize singlet excitons that account for 25% of the total number of excitons in the light-emitting layer, the theoretical internal quantum efficiency of this mechanism can only reach 25%, which is obviously not an efficient light-emitting mechanism.

Method used

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  • Bi(trimethylphenyl) boron derivatives and application thereof in white organic light-emitting diode
  • Bi(trimethylphenyl) boron derivatives and application thereof in white organic light-emitting diode
  • Bi(trimethylphenyl) boron derivatives and application thereof in white organic light-emitting diode

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0076] Synthesis of compound I1: the synthetic route is as follows:

[0077]

[0078] Synthesis of compound I1: Stir 1.6g of 4-bromo-4'-(diphenylamino)biphenyl and 20mL of tetrahydrofuran (analytical pure) at -78°C under nitrogen protection, slowly add 2.5ml dropwise to a concentration of 2.4mol / L The n-hexane solution of n-butyllithium was stirred for 1 h, then a solution of 1.6 g of bis(trimethylphenyl) boron fluoride dissolved in 10 ml of tetrahydrofuran (analytical grade) was added, and stirred for 12 h. The reaction solution was extracted with dichloromethane, washed with water and dried over anhydrous sodium sulfate, and evaporated to dryness under reduced pressure to obtain a crude product. The crude product was separated on a silica gel column. The eluent used was a mixture of dichloromethane and petroleum ether at a volume ratio of 1:3. After drying in a vacuum oven, 1.69 g of white solid I1 was obtained with a yield of 75%.

[0079] MS (m / e) of product I1: 569, c...

Embodiment 2

[0081] The synthetic route of compound I2 is as follows:

[0082]

[0083] Synthesis of compound I2: Stir 0.876g of 9-(7-bromo-9,9'-dimethyl-2-fluorenyl)carbazole and 10mL of tetrahydrofuran (analytical pure) at -78°C under nitrogen protection, slowly drop Add 1.25ml of n-butyllithium n-hexane solution with a concentration of 2.4mol / L, stir for 1h, then add a solution of 0.804g of bis(trimethylphenyl)boron fluoride dissolved in 5ml of tetrahydrofuran (analytical grade), and stir for 12h. The reaction solution was extracted with dichloromethane, washed with water and dried over anhydrous sodium sulfate, and evaporated to dryness under reduced pressure to obtain a crude product. The crude product was separated on a silica gel column, and the eluent used was a mixture of dichloromethane and petroleum ether at a volume ratio of 1:2. After drying in a vacuum oven, 0.8 g of white solid I2 was obtained, with a yield of 65%.

[0084] MS (m / e) of product I2: 607, corresponding to: ...

Embodiment 3

[0086] The synthetic route of compound I3 is as follows:

[0087]

[0088] Synthesis of compound I3: 1.1g of N-(7-bromo-9,9'-dimethyl-2-fluorenyl)di-tert-butyldiphenylamine and 10mL of tetrahydrofuran (analytical grade) were placed at -78°C under nitrogen protection Stir, slowly add 1.25ml of n-butyllithium n-hexane solution with a concentration of 2.4mol / L dropwise, stir for 1h, then add 0.804g of bis(trimethylphenyl)boron fluoride dissolved in 5ml of tetrahydrofuran (analytical pure) solution, Stir for 12h. The reaction solution was extracted with dichloromethane, washed with water and dried over anhydrous sodium sulfate, and evaporated to dryness under reduced pressure to obtain a crude product. The crude product was separated on a silica gel column, and the eluent used was a mixture of dichloromethane and petroleum ether at a volume ratio of 1:4. After drying in a vacuum oven, 0.95 g of white solid I3 was obtained, with a yield of 66%.

[0089] MS (m / e) of product I3:...

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Abstract

The invention discloses bi(trimethylphenyl) boron derivatives. The derivatives are compounds with a structure show in a formula I; the formula I is as shown in the specification; the compounds shown in the formula I can emit efficient blue fluorescence, and also have high triplet level; green and red phosphor doped materials also can be sensitized when the efficient blue fluorescence is emitted; therefore, the technological conditions of preparation of white organic light-emitting diodes (WOLEDs) are met. Meanwhile, the invention also discloses a preparation method of the compounds shown in the formula I and application thereof in preparation of the white organic light-emitting diodes.

Description

technical field [0001] The invention relates to the field of organic electroluminescent materials, in particular to a bis(trimethylphenyl)boron derivative and its application in white light organic electroluminescent diodes. Background technique [0002] In recent years, the research on white light organic electroluminescent materials and devices has received great attention from international academic circles, governments and industries. Countries and regions such as the United States, Europe, Japan, etc. have launched major research programs (the Next Generation Lighting Initiative of the United States, the European Union OLLA, Japan 21Century Lighting Program) to strengthen research in this field, because white organic electroluminescent technology (WOLED) is expected to become one of the most important solid-state light source technologies in the new generation. The theory of WOLED predicts that the electro-optical conversion efficiency will be several times, even more t...

Claims

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Application Information

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IPC IPC(8): C07F5/02C09K11/06H01L51/54H01L51/50
Inventor 张晓宏陈湛郑才俊欧雪梅李凡
Owner TECHNICAL INST OF PHYSICS & CHEMISTRY - CHINESE ACAD OF SCI
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