Spirobifluorene organic electroluminescent compound and organic electroluminescent device

The technology of a compound, spirobifluorene, is applied in the field of organic electroluminescent materials, which can solve the problems of insufficient development of organic electroluminescent materials and backward panel manufacturing enterprises, and achieve good aromaticity and thermal stability, reduce planarity and crystallization Sexuality and the effect of reducing manufacturing costs

Active Publication Date: 2020-12-01
NANJING TOPTO MATERIALS CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] As far as the actual needs of the current organic electroluminescent industry are concerned, the develop...

Method used

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  • Spirobifluorene organic electroluminescent compound and organic electroluminescent device
  • Spirobifluorene organic electroluminescent compound and organic electroluminescent device
  • Spirobifluorene organic electroluminescent compound and organic electroluminescent device

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0053]

[0054] The specific synthetic method of compound G20 is as follows:

[0055]

[0056] (1) Compound 1 (0.1mol, 25.7g), FeCl3 (0.1eq, 0.01mol, 1.62g), CS 2 (514g, 20 times the mass of compound 1) was added to the reaction flask, chlorobutane (1.1eq, 0.11mol, 10.18g) was added under ice bath, and after the addition was completed, the room temperature was slowly returned to the reaction for 10h, and the reaction solution was poured into Ice cubes (1028g, the mass of ice cubes is CS 2 2 times of mass), hydrochloric acid was added dropwise until the pH of the system reached 2-3, and then dichloromethane (1028g, CS 2 2 times the mass of the compound) for extraction, dichloromethane phase separation, washing with water several times, drying over anhydrous sodium sulfate, and concentrating under reduced pressure to obtain the crude product of compound 2, which was purified by column chromatography to obtain the pure product of compound 2 (18.3g, harvested rate 58.3%), ...

Embodiment 2

[0063]

[0064] The specific synthetic method of compound G116 is as follows:

[0065]

[0066] (1) Compound 7 (1eq, 288g / mol, 57mmol, 16.4g) and anhydrous THF (164g, 10 times the mass of compound 7) were added to the reaction flask under the protection of nitrogen. The liquid nitrogen was cooled to -78°C, and added dropwise n-Butyllithium (1.1eq, 62.7mmol), after reacting for 30min, compound 1 (14.7g, 257.97g / mol, 57mmol), anhydrous THF (147g, 10 times the mass of compound 2) were mixed and added dropwise, Continue to react at -78°C for 2 hours, then add ammonium chloride solution to quench, slowly return to room temperature, add dichloromethane and water for extraction and separation, separate the dichloromethane phase, wash with water several times, dry over anhydrous sodium sulfate, reduce Concentrate under reduced pressure to obtain the crude product of compound 8, obtain the pure product of compound 8 (15.2g, yield 57.1%) after column chromatography purification, M...

Embodiment 3

[0072]

[0073] The specific synthetic method of compound G148 is as follows:

[0074] Operation in step (1) and step (2) is basically the same as in Example 2, and step (3) is as follows:

[0075]

[0076] (3) Under nitrogen protection, compound 9 (10g, 22.2mmol), compound 10 (1.1eq, 321g / mol, 24.4mmol, 7.84g), sodium tert-butoxide (1.1eq, 96.1g / mol, 24.4mmol, 2.35g), Pd 2 (dba) 3 (5%eq, 915.72g / mol, 1.11mmol, 1.02g), tri-tert-butylphosphine (5%eq, 202.317g / mol, 1.11mmol, 0.223g), toluene (100g, 10 times the mass of compound 9) Add it into the reaction flask, heat up to reflux reaction for 5 hours after the addition, cool down to room temperature after the reaction, add water and stir for 15 minutes, and then filter to obtain the filtrate. After the filtrate is separated, the organic phase is obtained. After purification by column chromatography, high-purity G148 (7.63g, yield 49.9%) was obtained, MS (EI): 691 (M + ).

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PUM

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Abstract

The invention discloses a spirobifluorene organic electroluminescent compound and an organic electroluminescent device. The structural formula of the spirobifluorene organic electroluminescent compound is shown as a formula I, the compound can be used as an organic electroluminescent material. Compared with the techniques in the prior art, the planarity of material molecules is reduced so that theuse effect and the use range of the material can be effectively improved; the increase of the molecular torque and degree of freedom of the material effectively improves the hole transport capabilityof the material, and adjusts the HOMO energy level of the hole transport material, thereby greatly reducing the driving voltage of the organic electroluminescent device, effectively reducing the energy consumption, and greatly prolonging the service life of the organic electroluminescent device.

Description

technical field [0001] The invention belongs to the technical field of organic electroluminescent materials, and in particular relates to a spirobifluorene organic electroluminescent compound and an organic electroluminescent device. Background technique [0002] Organic light-emitting devices (Organic Light-emitting Devices, OLED) are spontaneous light-emitting devices using the following principle: when an electric field is applied, fluorescent substances emit light through the recombination of holes injected from the positive electrode and electrons injected from the negative electrode. This self-luminous device has the characteristics of low voltage, high brightness, wide viewing angle, fast response, good temperature adaptability, etc., and is ultra-thin, and can be fabricated on flexible panels. It is widely used in mobile phones, tablet computers, TVs, lighting, etc. and other fields. [0003] The organic electroluminescent device is like a sandwich structure, includ...

Claims

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Application Information

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IPC IPC(8): C07C211/61C07D307/91C07D209/88C07D209/80C07D239/20C07D251/24C07D213/38C07D251/42C07D209/86C09K11/06H01L51/50H01L51/54
CPCC07C211/61C07D307/91C07D209/88C07D209/80C07D239/20C07D251/24C07D213/38C07D251/42C07D209/86C09K11/06C09K2211/1007C09K2211/1011C09K2211/1014C09K2211/1029C09K2211/1044C09K2211/1059C09K2211/1088H10K85/622H10K85/624H10K85/636H10K85/626H10K85/633H10K85/615H10K85/631H10K85/654H10K85/6574H10K85/6572H10K50/15H10K50/00C07D209/82
Inventor 钱超许军
Owner NANJING TOPTO MATERIALS CO LTD
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