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Halogenated aromatic ketone derivative based organic electroluminescent material, preparation method therefor and application of organic electroluminescent material

A technology of electroluminescent materials and derivatives, applied in the fields of luminescent materials, organic chemistry, chemical instruments and methods, etc., can solve the problems of efficiency roll-off, and achieve the effect of efficiency roll-off, high device efficiency, and strong applicability

Pending Publication Date: 2020-02-11
SOUTH CHINA UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, non-doped TADF materials basically face serious efficiency roll-off problems, and must be doped to reduce adverse effects, which greatly increases the process requirements

Method used

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  • Halogenated aromatic ketone derivative based organic electroluminescent material, preparation method therefor and application of organic electroluminescent material
  • Halogenated aromatic ketone derivative based organic electroluminescent material, preparation method therefor and application of organic electroluminescent material
  • Halogenated aromatic ketone derivative based organic electroluminescent material, preparation method therefor and application of organic electroluminescent material

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0029] Example 1: Preparation of organic electroluminescent molecules (3-CCP-BP-PXZ) based on halogenated aromatic ketone derivatives

[0030]

[0031] synthetic route:

[0032]

[0033] (1) 3-chloro-N-phenylcarbazole (0.83g, 3.0mmol), p-fluorobenzoyl chloride (0.57g, 3.6mmol) and AlCl 3 (0.48g, 3.6mmol) was added to a 100mL two-necked flask, vacuumed, filled with N 2 (repeat 3 times), add ultra-dry dichloromethane (30 mL) under ice-bath conditions, heat up to 40° C., and react for 4 hours. Cooled to room temperature, quenched with dilute hydrochloric acid washing solution (30 mL), extracted with dichloromethane, dried over anhydrous magnesium sulfate, concentrated and passed through column to obtain white intermediate 2 with a yield of 88%.

[0034] (2) Add intermediate 2 (0.40g, 1.0mmol), phenoxazine (0.27g, 1.5mmol) and potassium tert-butoxide (0.22g, 2.0mmol) into a 100mL two-necked flask, pump and exchange gas 3 times, and protect with nitrogen DMF (20 mL) was ad...

Embodiment 2

[0036] Example 2: Preparation of organic electroluminescent molecules (9-CCP-BP-PXZ) based on halogenated aromatic ketone derivatives

[0037]

[0038] synthetic route:

[0039]

[0040] (1) 9-chloro-N-phenylcarbazole (0.83g, 3.0mmol), p-fluorobenzoyl chloride (0.57g, 3.6mmol) and AlCl 3 (0.48g, 3.6mmol) was added to a 100mL two-necked flask, vacuumed, filled with N 2 (repeat 3 times), add ultra-dry dichloromethane (30 mL) under ice-bath conditions, heat up to 40° C., and react for 4 hours. Cooled to room temperature, quenched with dilute hydrochloric acid washing solution (30 mL), extracted with dichloromethane, dried over anhydrous magnesium sulfate, concentrated and passed through column to obtain white intermediate 2 with a yield of 90%.

[0041] (2) Add intermediate 2 (0.40g, 1.0mmol), phenoxazine (0.27g, 1.5mmol) and potassium tert-butoxide (0.22g, 2.0mmol) into a 100mL two-necked flask, pump and exchange gas 3 times, and protect with nitrogen DMF (20 mL) was ad...

Embodiment 3

[0043] Example 3: Preparation of organic electroluminescent molecules (3,9-CCP-BP-PXZ) based on halogenated aromatic ketone derivatives

[0044]

[0045] synthetic route:

[0046]

[0047] (1) 3,9-dichloro-N-phenylcarbazole (0.93g, 3.0mmol), p-fluorobenzoyl chloride (0.57g, 3.6mmol) and AlCl 3 (0.48g, 3.6mmol) was added to a 100mL two-necked flask, vacuumed, filled with N 2 (repeat 3 times), add ultra-dry dichloromethane (30 mL) under ice-bath conditions, heat up to 40° C., and react for 4 hours. Cooled to room temperature, quenched with dilute hydrochloric acid washing solution (30 mL), extracted with dichloromethane, dried over anhydrous magnesium sulfate, concentrated and passed through column to obtain white intermediate 2 with a yield of 88%.

[0048] (2) Add intermediate 2 (0.43g, 1.0mmol), phenoxazine (0.27g, 1.5mmol) and potassium tert-butoxide (0.22g, 2.0mmol) into a 100mL two-necked flask, pump and exchange gas 3 times, and protect with nitrogen DMF (20 mL) ...

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Abstract

The invention discloses a halogenated aromatic ketone derivative based organic electroluminescent material, a preparation method therefor and an application of the organic electroluminescent material.The organic electroluminescent material has a structure represented by a formula shown in the description, wherein R1 are different aromatic ring electron-donating groups or halogenated aromatic ringelectron-donating groups, R2 is methyl, an aromatic ring electron-donating group or halogenated aromatic ring electron-donating group, and X is a hydrogen atom or halogen atom; and at least one groupof the X, the R1 and the R2 contains a halogen atom. The organic electroluminescent material has AIDF properties and high solid-state fluorescence quantum efficiency. A synthesis method is simple andefficient. OLEDs devices based on the organic electroluminescent material have high non-doped device efficiency, and the efficiency roll-off is still very low in case of high brightness. The organicelectroluminescent material disclosed by the invention is high in applicability, and the OLEDs devices of different doped concentrations all show high device efficiency and low efficiency roll-off athigh brightness, so that the organic electroluminescent material is advantageously applied extensively to illumination and display devices.

Description

technical field [0001] The invention belongs to the field of organic electroluminescent materials, and in particular relates to a class of organic electroluminescent materials based on halogenated aromatic ketone derivatives and a preparation method and application thereof. Background technique [0002] Organic Light Emitting Diode (OLED), as a new generation of display device, has the advantages of self-illumination, wide viewing angle, high contrast, low power consumption and extremely fast response speed. Due to the above advantages, OLED display technology has been more and more used in display fields such as mobile phones, TVs, and computers. As a new generation of display devices, OLED has broad development prospects. Therefore, it is of great significance to develop new high-efficiency and high-stability OLED materials. [0003] Traditional OLED materials can only use 25% of the singlet excitons to emit light during the electroluminescent process, while the remaining...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D413/10C09K11/06H01L51/50H01L51/54
CPCC07D413/10C09K11/06C09K2211/1029C09K2211/1033H10K85/657H10K85/6572H10K50/11
Inventor 唐本忠赵祖金徐静文朱翔宇秦安军胡蓉蓉王志明
Owner SOUTH CHINA UNIV OF TECH
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