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Aromatic amine compound based on pyrene and carbazole, preparation method of aromatic amine compound and application of aromatic amine compound as organic electroluminescent material

A compound and aromatic amine technology, applied in the application field of organic electroluminescent materials, can solve the problems of poor color purity, poor luminous efficiency, wide emission spectrum, etc., and achieve the effects of reduced driving voltage, reduced operating voltage, and strong luminous efficiency

Active Publication Date: 2022-03-08
安徽秀朗新材料科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, most blue fluorescent materials (such as BD1) have problems such as too wide emission spectrum, poor color purity, and poor luminous efficiency.

Method used

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  • Aromatic amine compound based on pyrene and carbazole, preparation method of aromatic amine compound and application of aromatic amine compound as organic electroluminescent material
  • Aromatic amine compound based on pyrene and carbazole, preparation method of aromatic amine compound and application of aromatic amine compound as organic electroluminescent material
  • Aromatic amine compound based on pyrene and carbazole, preparation method of aromatic amine compound and application of aromatic amine compound as organic electroluminescent material

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preparation example Construction

[0048] The present invention provides the preparation method of the above-mentioned aromatic amine compound based on pyrene and carbazole, comprising the following steps:

[0049] (1) Under the action of a phosphine-palladium catalyst, a compound having a structure shown in formula a and a compound having a structure shown in formula b carry out the first Suzuki reaction to obtain a compound having a structure shown in formula c;

[0050]

[0051] (2) a compound having a structure shown in formula c is subjected to a halogenation reaction with bromosuccinimide to obtain a compound having a structure shown in formula d;

[0052]

[0053] (3) A compound having a structure shown in formula d is mixed with n-butyllithium and trimethyl borate, and subjected to a lithiation reaction to obtain a compound having a structure shown in formula e;

[0054]

[0055] (4) under the action of the phosphine-palladium catalyst, the compound having the structure shown in formula e and t...

Embodiment 1

[0123] Preparation of aromatic amine compound I-5 based on pyrene and carbazole

[0124] The first step: the preparation of intermediate 1

[0125]

[0126] In the reaction flask, add 100mmol raw material 1, 100mmol raw material 2, 200mmol potassium carbonate, 200mL toluene, 100mL ethanol and 10mL deionized water, add 0.5g tetrakistriphenylphosphine palladium under nitrogen atmosphere, react at 100 degrees for 10 hours, cool , filtered, and the product was recrystallized from toluene with a yield of 91%.

[0127] The second step: the preparation of intermediate 2

[0128]

[0129] In the reaction bottle, add 70mmol intermediate 1, 73mmol bromosuccinimide, 180ml DMF, react at room temperature for 12 hours, add 550mL deionized water, filter, dry, and recrystallize with toluene, the yield is 86%.

[0130] The third step: the preparation of intermediate 3

[0131]

[0132] In the reaction bottle, add 50mmol of intermediate 2, 150ml of anhydrous tetrahydrofuran, under t...

Embodiment 2

[0147] Preparation of organic electroluminescent devices OLEDs using compound I-5 as blue light material: device preparation equipment: MB-MO-SE1 vacuum thermal evaporation coating equipment from Mbraun, Germany; testing equipment: Keithley Source 2400, PhotoResearch PR655 spectrometer.

[0148] The structure of the device is: ITO / HAT-CN(10nm) / NPB(50nm) / BH:8% compound I-5(30nm) / TmPyPB(40nm) / LiF(1nm) / Al(100nm)

[0149] The compounds used in the device are all commercial products, and the structural formula is as follows:

[0150]

[0151]

[0152] The specific preparation steps of the device are as follows:

[0153] Use 10Ω / sq ITO glass as the substrate, clean it with glass cleaning agent first, then use deionized water and acetone to sonicate 3 times each, and after UV-ozone treatment for 15 minutes, the organic layer is evaporated. First, 10nm hole injection material HAT-CN was deposited on the ITO glass substrate, then 50nm NPB was deposited as a hole transport layer,...

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Abstract

The invention provides an aromatic amine compound based on pyrene and carbazole, a preparation method of the aromatic amine compound and application of the aromatic amine compound as an organic electroluminescent material, and belongs to the technical field of electroluminescent materials. Anthracene and pyrene groups are introduced on the basis of aromatic amine, and the two groups have very high quantum efficiency, so that the luminous efficiency of the material can be effectively improved, and blue light can be emitted under a power-on condition. Meanwhile, the two groups have good thermal stability, the roll-off phenomenon of the device can be improved, and the service life of the device can be prolonged. The carbazole group is introduced, so that the stability and planarity of the aromatic amine compound can be improved, the luminous efficiency is improved, and the working voltage is reduced. When the aromatic amine compound based on pyrene and carbazole provided by the invention is used as a luminescent material of an organic electroluminescent device, the working voltage is 4.3 V, and the current efficiency is 7.7 cd / A. Compared with an organic electroluminescent device element taking BD1 as a blue light doping material, the aromatic amine compound based on pyrene and carbazole has the advantages that the efficiency is higher, and the driving voltage is reduced.

Description

technical field [0001] The invention relates to the technical field of organic electroluminescent materials, in particular to an aromatic amine compound based on pyrene and carbazole, a preparation method thereof and an application as an organic electroluminescent material. Background technique [0002] Organic Electroluminescence Devices (Organic Electroluminescence Devices or OrganicLightEmitting Diodes, hereinafter referred to as OLEDs) have a wide range of applications in various fields due to their ultra-thin, fully cured, self-luminous, fast response, good temperature characteristics, and flexible displays. application. The light-emitting mechanism of OLED is generally considered to be driven by the external voltage, the electrons and holes injected by the electrode meet in the organic matter, and the energy is transferred to the organic light-emitting molecules, and the electric energy is converted into internal energy of the molecule, so that it is excited. From the...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D209/86C09K11/06H01L51/54H01L51/50
CPCC07D209/86C09K11/06C09K2211/1011C09K2211/1007C09K2211/1014C09K2211/1029H10K85/626H10K85/633H10K85/6572H10K50/11Y02E10/549
Inventor 曹辰辉税新凤庞玉东魏斌
Owner 安徽秀朗新材料科技有限公司
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