Boron-containing fused ring compound and electronic device

A compound and fused ring technology, which is applied in the field of boron-containing fused ring compounds and electronic devices, can solve problems such as poor luminous effect, achieve the effects of increasing conjugation, easy availability of raw materials, and enhancing multiple resonance effects

Pending Publication Date: 2022-03-18
UNIV OF SCI & TECH OF CHINA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0008] In view of the above problems, the present disclosure provides a boron-containing condensed ring compound and an electronic device, which are used to at least partially solve technical problems such as poor luminous effect of traditional organic light-emitting layer materials

Method used

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  • Boron-containing fused ring compound and electronic device
  • Boron-containing fused ring compound and electronic device
  • Boron-containing fused ring compound and electronic device

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0138] Embodiment 1: the synthesis of compound 1-1

[0139] (Synthesis of Compound M1)

[0140] The structural formula and synthetic route of compound M1 are shown in the figure below:

[0141]

[0142] In a 100mL two-necked flask, add 1.3g (6.0mmol) 2,3-dichlorobromobenzene, 1.0g (5.0mmol) iminodibenzyl, 0.6g (6.0mmol) sodium tert-butoxide, 0.1g (0.2mmol) Tri-tert-butylphosphine tetrafluoroborate, 0.27g (0.3mmol) tris(dibenzylideneacetone) dipalladium, after degassing the reaction system, under the protection of nitrogen, add 40mL of toluene, stir and heat to 110°C for reaction 12 Hour. After the reaction was complete, the system was cooled to room temperature, filtered under reduced pressure, and the filter residue was washed with a large amount of dichloromethane, the filtrate was concentrated to obtain a crude product, and the crude product was washed with dichloromethane:petroleum ether=2:3 (volume ratio) The deagent was separated and purified on a silica...

Embodiment 2

[0151] Embodiment 2: the synthesis of compound 1-16

[0152] (Synthesis of compound M3)

[0153] The structural formula and synthetic route of compound M3 are shown in the figure below:

[0154]

[0155] Add 1.7g (5.0mmol) M1, 1.4g (5.0mmol) bis(4-tert-butylphenyl) amine, 0.6g (6.0mmol) sodium tert-butoxide, 0.05mL (0.2mmol) Tri-tert-butylphosphine, 0.27g (0.3mmol) tris(dibenzylideneacetone)dipalladium, after degassing the reaction system, under the protection of nitrogen, add 40mL of toluene, stir and heat to 110°C for 12 hours. After the reaction was complete, the system was cooled to room temperature, filtered under reduced pressure, and the filter residue was washed with a large amount of dichloromethane, the filtrate was concentrated to obtain a crude product, and the crude product was washed with dichloromethane:petroleum ether=1:1 (volume ratio) The deagent was separated and purified on a silica gel column to obtain 2.0 g of solid with a yield of 68%. M...

Embodiment 3

[0160] Embodiment 3: the synthesis of compound 5-2

[0161] (Synthesis of compound M4)

[0162] The synthetic route of compound M4 is as follows:

[0163]

[0164] In a 100mL two-necked flask, 1.3g (6.0mmol) 2-chloro-3-fluorobromobenzene, 1.0g (5.0mmol) iminodibenzyl, 0.6g (6.0mmol) sodium tert-butoxide, 0.1g (0.3mmol) ) tri-tert-butylphosphine tetrafluoroborate, 0.27g (0.3mmol) tris(dibenzylideneacetone) dipalladium, after degassing the reaction system, under the protection of nitrogen, add 40mL toluene, stir and heat to 110°C for reaction 12 hours. After the reaction was complete, the system was cooled to room temperature, filtered under reduced pressure, and the filter residue was washed with a large amount of dichloromethane, the filtrate was concentrated to obtain a crude product, and the crude product was washed with dichloromethane:petroleum ether=2:3 (volume ratio) The deagent was separated and purified on a silica gel column to obtain 1.7 g of solid w...

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Abstract

The invention relates to the technical field of organic photoelectric materials, in particular to a boron-containing compound and an organic electroluminescent device. According to the boron-containing compound (formula I) disclosed by the invention, rigid aniline (such as iminodibenzyl) and other structures are introduced into a skeleton, so that the rigidity of the whole molecule is further enhanced, and the performance of the material is further improved by carrying out structural modification on the periphery of the rigid skeleton. The boron-containing fused ring compound disclosed by the invention has relatively narrow luminescence peak, excellent film-forming property and thermal stability and relatively high fluorescence quantum yield, and can be used for preparing an organic electroluminescent device. In addition, the boron-containing fused ring compound can be used as a constituent material of a light-emitting layer, and can reduce driving voltage and improve efficiency, brightness, service life, color purity and the like. In addition, the preparation method of the boron-containing fused ring compound is simple, raw materials are easy to obtain, and industrial development requirements can be met.

Description

technical field [0001] The disclosure relates to the technical field of organic photoelectric materials, in particular to a boron-containing condensed ring compound and an electronic device. Background technique [0002] Organic electroluminescent devices have a series of advantages such as self-luminescence, low-voltage drive, full curing, wide viewing angle, simple composition and process, etc. Compared with liquid crystal displays, organic electroluminescent devices do not need a backlight. Therefore, organic electroluminescent devices have broad application prospects. [0003] An organic electroluminescent device generally includes an anode, a metal cathode, and an organic layer sandwiched between them. The organic layer mainly includes a hole injection layer, a hole transport layer, an electron blocking layer, a light-emitting layer, a hole blocking layer, an electron transport layer, and an electron injection layer. In addition, most light-emitting layers adopt a hos...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F5/02C07F7/08C09K11/06H01L51/54H01L51/50
CPCC07F5/027C07F7/0816C09K11/06C09K2211/1055C09K2211/107C09K2211/104C09K2211/1011C09K2211/1088C09K2211/1029C09K2211/1059H10K85/622H10K85/636H10K85/631H10K85/615H10K85/654H10K85/6574H10K85/657H10K85/40H10K85/6572H10K50/11
Inventor 崔林松朱向东叶志峰
Owner UNIV OF SCI & TECH OF CHINA
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