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Boron-containing spiro compound and organic electroluminescent device

A spiro compound, unsubstituted technology, applied in the field of electronic materials, can solve problems such as easy aggregation, poor color purity of materials and devices with luminous performance

Pending Publication Date: 2021-07-06
SHENZHEN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] Aiming at the deficiencies of the prior art, the purpose of the present invention is to overcome the easy aggregation of thermally activated fluorescent materials of the boron / nitrogen multiple resonance system in the existing D-A type thermally activated fluorescent materials, and the aggregation-induced quenching effect is easy to occur when preparing electroluminescent devices , and when the doping ratio is high, the aggregation will lead to a broadening of the half-peak width, thereby deteriorating the luminescent performance of the material and the color purity of the device, thereby providing a boron-containing spiro compound and an organic electroluminescent device.

Method used

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  • Boron-containing spiro compound and organic electroluminescent device

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0127]This embodiment provides a boron-containing spiro compound S-1, which has the following structure:

[0128]

[0129] The synthetic route of compound S-1 is as follows:

[0130]

[0131] The preparation method of compound S-1 specifically comprises the following steps:

[0132] 1) Synthesis of intermediate 3

[0133] Compound 1 (3.48g, 10mmol) was dissolved in 30mL of dry tetrahydrofuran, cooled to -78°C, n-BuLi (2.5mol / L, 11mmol) was added dropwise to the above solution, and the reaction was continued at this temperature for 2h; Compound 2 (2.83g, 10mmol) was dissolved in 20mL of dry THF, and added dropwise to the above mixture, continued to react at -78°C for 30min, then naturally warmed to room temperature, and reacted at room temperature for 12h, and 20mL 3mol / L of HCl was added dropwise to the above mixed solution, the reaction was continued for 12h, and the above mixed solution was poured into saturated Na 2 CO 3 solution, and then utilize dichloromethane ...

Embodiment 2

[0142] This embodiment provides a boron-containing spiro compound S-69, which has the following structure:

[0143]

[0144] The synthetic route of compound S-69 is as follows:

[0145]

[0146] The preparation method of compound S-69 specifically comprises the following steps:

[0147] 1) Synthesis of Intermediate 6

[0148] The above intermediate 4 (1.2g, 2mmol) and naphthol (577mg, 4mmol) were dissolved in 10mL N-methylpyrrolidone, cesium carbonate (2.6g, 8mmol) was added, and the temperature was raised to 170°C for 18h. After the reaction was completed, , cooled to room temperature, then using dichloromethane to extract the reaction solution, drying the organic phase with anhydrous sodium sulfate, spinning to remove the organic solvent, and separating by column chromatography to obtain white solid intermediate 6 (1.16g, 68%), MS (EI):m / z 850.2[M + ].

[0149] 2) Synthesis of target product S-69

[0150] Dissolve the above-prepared intermediate 6 (852mg, 1mmol) i...

Embodiment 3

[0152] This embodiment provides a boron-containing spiro compound S-1036, which has the following structure:

[0153]

[0154] The synthetic route of compound S-1036 is as follows:

[0155]

[0156] The preparation method of compound S-1036 specifically comprises the following steps:

[0157] 1) Synthesis of Intermediate 7

[0158] The above intermediate 4 (1.2g, 2mmol) and p-cyanophenol (476mg, 3mmol) were dissolved in 10mL of N-methylpyrrolidone, cesium carbonate (2.6g, 8mmol) was added, and the temperature was raised to 170°C for 18h. After completion, cool to room temperature, then use dichloromethane to extract the reaction solution, dry the organic phase with anhydrous sodium sulfate, spin dry to remove the organic solvent, and separate by column chromatography to obtain white solid intermediate 7 (1.12g, 70%) , MS(EI):m / z 800.1[M + ].

[0159] 2) Synthesis of target product S-1036

[0160] Dissolve the above-prepared intermediate 7 (802mg, 1mmol) in 40mL of d...

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Abstract

The invention relates to the technical field of electronic materials, in particular to a boron-containing spiro compound and an organic electroluminescent device. The boron-containing spiro compound provided by the invention has a structure as shown in a formula I. The boron-containing spiro compound provided by the invention effectively improves the aggregation-induced fluorescence quenching effect caused by a rigid plane structure of a boron-nitrogen condensed ring and the defect that the half-peak width is increased due to aggregation, and reduces the half-peak width, so that in the process of increasing the doping ratio, the light-emitting property and the color purity of the device are not reduced but are improved to a certain extent.

Description

technical field [0001] The invention relates to the technical field of electronic materials, in particular to a boron-containing spiro compound and an organic electroluminescence device. Background technique [0002] Since it was first reported by C.W.Tang and S.A.VanSlyke in 1987, organic electroluminescent diodes (OLEDs) have been favored by a large number of scientific researchers and have shown huge market value. [0003] Although the commercialized organic electroluminescent diodes have shown many advantages, the current luminescent materials have a wide excitation spectrum (>40nm) due to the vibrational coupling between the ground state and the excited state and the relaxation of the excited state structure. , so that the color purity of the device prepared by the luminescent material is not high, which cannot meet people's requirements for high color purity display. In recent years, thermally activated delayed fluorescent materials, which have received widespread ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F5/02C09K11/06C07F7/08H01L51/54
CPCC07F5/02C09K11/06C07F7/0816C09K2211/1037C09K2211/1055C09K2211/104C09K2211/107C09K2211/1085H10K85/657
Inventor 杨楚罗华涛黄忠衍
Owner SHENZHEN UNIV
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