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Boron-containing heterocyclic compound and application thereof in organic photoelectric device

A technology of compound and boron heterocycle, applied in the field of boron-containing heterocycle compound and its application in organic optoelectronic devices, to achieve high thermal stability, low voltage, and improve the effect of luminescence stability

Active Publication Date: 2018-11-09
陕西蒲城海泰新材料产业有限责任公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Because the fluorescent type uses singlet excitons to emit light, its internal quantum efficiency can only reach 25%.

Method used

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  • Boron-containing heterocyclic compound and application thereof in organic photoelectric device
  • Boron-containing heterocyclic compound and application thereof in organic photoelectric device
  • Boron-containing heterocyclic compound and application thereof in organic photoelectric device

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0112]

[0113] Add 25g of compound 3-1, 25g of 2,4-dibromo-1-fluoro-benzene, 300ml of dimethyl sulfoxide (DMSO) into a 500ml three-necked flask, blow nitrogen, stir to dissolve the raw materials completely, add K 2 CO 3 16.5g, the solution was yellow. Turn on the heating to 110°C for 8 hours and then take samples for monitoring. After the raw materials are completely reacted, cool down to room temperature for post-processing.

[0114] The reaction solution was added to 3 times the volume of water, the product was stirred to precipitate, filtered, the filter cake was dissolved in toluene, and washed with water until neutral. Anhydrous Na 2 SO 4 After drying for 2 hours, the desiccant was removed by filtration, and the filter cake was rinsed with a small amount of toluene. The filtrates were combined, concentrated and purified by column to obtain the target compound 3-2 as a yellow solid 36.1 g, with a yield of 76.2%.

[0115] 1 H NMR (400MHz, CDC13) δ7.61 (s, 2H), 7.3...

Embodiment 2

[0117]

[0118] Add 36g of compound 3-2 and 300ml of tetrahydrofuran (THF) into a 1L three-necked flask, replace the air in the reaction flask with nitrogen, cool down to -78°C, and slowly add n-butyllithium (n-BuLi) dropwise under nitrogen protection ( 2.0M in THF) 75ml, heat preservation reaction at this temperature for 2h, add 9.6g of phenylboronic acid, keep this temperature for 6h and then naturally warm up to room temperature, when TLC monitors that the reaction of raw materials is complete, add 1M ammonium chloride solution to adjust the pH to neutral After stirring for 10 minutes, let it stand for liquid separation. Anhydrous Na for organic phase 2 SO 4 After drying for 2 hours and filtering, the filtrate was concentrated and passed through a silica gel column to obtain 20.1 g of compound 3-3 as a white solid, with a yield of 65.3%.

[0119] 1 H NMR (400MHz, CDC13) δ7.42(t, J=7.6, 1H), 7.35(t, J=7.6, 2H), 7.31(d, J=7.6, 2H), 7.22-7.24(m, 4H) , 7.18 (d, J=7.6, 2H...

Embodiment 3

[0121]

[0122] Add 20g of compound 3-3, 200ml of glacial acetic acid (AcOH), 13g of 30% hydrogen peroxide in a 500ml three-necked flask, stir and react at room temperature for 2h, and after TLC monitors that the raw materials have reacted completely, add 1M sodium bicarbonate solution to adjust the pH to be neutral. After stirring for 10 min, let it stand for liquid separation. The aqueous phase was extracted with dichloromethane, and the combined organic phases were washed with anhydrous Na 2 SO 4 After drying for 2 hours and filtering, the filtrate was concentrated and passed through a silica gel column to obtain 20.1 g of compound 3-4 as a white solid, with a yield of 93.5%.

[0123] 1 H NMR (400MHz, CDC13) δ7.82(d, J=8.0, 2H), 7.66-7.73(m, 4H), 7.42(t, J=7.6, 1H), 7.35(t, J=7.6, 2H) , 7.31 (d, J=7.6, 2H);

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Abstract

The invention provides a boron-containing heterocyclic compound and application thereof in an organic photoelectric device. The boron-containing heterocyclic compound is represented by a general formula (1) shown in the description. The invention further provides application of a material produced from the boron-containing heterocyclic compound in an organic electroluminescence element and application of the organic electroluminescence element in an organic electroluminescence display device. The boron-containing heterocyclic compound provided by the invention has a structure similar to a boron heteroanthracene derivative and has a proper donor-acceptor structure, a relatively small deltaEst energy value and a proper HOMO / LUMO value, the high brightness, low voltage, high efficiency and long service life of an organic EL element can be realized, and meanwhile, a material prepared from the compound has relatively high heat stability, is capable of remarkably improving the light-emittingstability of the luminescent device and can be widely applied to OLED luminescent devices and display devices to be used as a luminescent layer main body material or a thermally active delayed fluorescence luminescent material.

Description

technical field [0001] The invention relates to the field of organic light-emitting elements with high luminous efficiency and organic electroluminescent functional materials, in particular to a boron-containing heterocyclic compound and its application in organic photoelectric devices. Background technique [0002] As a self-luminous electronic component, organic electroluminescent OLED (Organic Light Emission Diodes) display lighting mechanism is a new photoelectric information technology that directly converts electrical energy into light energy with the help of organic semiconductor functional materials under the action of a DC electric field. kind of. Its luminous color can be a single red, green, blue, yellow light or a combination of white light. The biggest feature of OLED light-emitting display technology is ultra-thin, fast response, ultra-lightweight, surface-emitting and flexible display. It can be used to manufacture monochrome or full-color displays. As a new ...

Claims

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Application Information

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IPC IPC(8): C07F7/10C07F9/6596C09K11/06H01L51/50H01L51/54
CPCC09K11/06C07F7/10C07F9/6596C09K2211/1096C09K2211/1044C09K2211/1037C09K2211/1033C09K2211/1003C09K2211/1029H10K85/657H10K85/6572H10K50/11
Inventor 孙军刘凯鹏张宏科杨燕高仁孝王小伟刘骞峰
Owner 陕西蒲城海泰新材料产业有限责任公司
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