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Carbazole derivative based on epoxybutane as well as preparation method and application of carbazole derivative

A technology of butylene oxide and carbazole, which is applied in the field of organic optoelectronics, can solve problems such as damage and interlayer miscibility, and achieve the effects of simple process, good solvent resistance and thermal stability, and improved hole transport capability.

Pending Publication Date: 2022-05-31
NANJING UNIV OF POSTS & TELECOMM
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, due to the similar structure of the organic functional layer materials, most of them are dissolved in the same organic solvent, so when the light-emitting layer film is prepared, the prepared hole transport layer film will be destroyed, that is, the phenomenon of interlayer miscibility

Method used

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  • Carbazole derivative based on epoxybutane as well as preparation method and application of carbazole derivative
  • Carbazole derivative based on epoxybutane as well as preparation method and application of carbazole derivative
  • Carbazole derivative based on epoxybutane as well as preparation method and application of carbazole derivative

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0042] Example 1: Oxe-DCzTPA (3,5-bis(4-((6-((3-ethyloxetan-3-yl)methoxy)hexyl)oxy)-9H-carbazole -9-yl)-N,N-diphenylaniline) preparation method

[0043] The synthetic route of described Oxe-DCzTPA is as follows:

[0044]

[0045] The Oxe-DCzTPA preparation process and NMR data are characterized by:

[0046] (1) Preparation of Compound 1: Dissolve 3g of compound 9H-carbazol-4-ol, 4.5g of potassium carbonate and 0.528g of compound TBABr in 160mL of ethyl acrylate for 1h at room temperature, then add 3.06mL of compound CH 3 I obtain compound 1, 3.01g, productive rate 94% after heating to reflux 24h: 1 H NMR (400MHz, Chloroform-d) δ8.32 (d, J = 7.8Hz, 1H), 8.03 (s, 1H), 7.43–7.30 (m, 3H), 7.26–7.21 (m, 1H), 7.08 – 7.00(m,1H),6.68(d,J=8.0Hz,1H),4.08(s,3H).

[0047] (2) Preparation of compound 2: Add 2 g of compound 1, an appropriate amount of 2.24 g of compound t-BuOK and 576 μL of 1-bromo-3,5-difluorobenzene into 10 mL of DMSO to dissolve in sequence, and heat to reflux for...

Embodiment 2

[0054] Embodiment 2: the photophysical property of Oxe-DCzTPA film

[0055] figure 2 The ultraviolet absorption spectrum, fluorescence spectrum and low temperature phosphorescence spectrum of the compound Oxe-DCzTPA in the film are given. The compound was dissolved in dichloromethane at a mass concentration of 4 mg / mL to form a film, and then its spectrum, fluorescence spectrum and low-temperature phosphorescence spectrum were measured. In the film, the ultraviolet absorption peaks of the compound are located at 246, 288 and 337nm respectively, the fluorescence spectrum of the compound has a peak at 379nm, and a slightly weaker peak at 363nm, and it can be known from the low-temperature phosphorescence spectrum that it is short at 420nm According to the calculation of the starting point on the wavelength side, the compound has a high triplet energy of 2.95eV, and the high triplet energy also makes it have good exciton blocking ability, which can be used as an exciton blockin...

Embodiment 3

[0056] Embodiment 3: the photophysical property of Oxe-DCzTPA solution

[0057] image 3 The fluorescence spectra of the compound Oxe-DCzTPA in different solutions are given, and the compounds are formulated into 10 -5 mol / L n-ethane, toluene, dichloromethane, tetrahydrofuran, dimethylformamide solvent dilute solution, pipette a certain volume of the compound solution into a fluorescence cuvette, and test its fluorescence spectrum. The fluorescence emission positions of the compounds in n-ethane, toluene, dichloromethane, tetrahydrofuran, and dimethylformamide solutions are all the same, and the emission wavelengths of the spectral peaks are 363nm, 371nm, 376nm, 376nm, and 384nm in sequence.

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Abstract

The invention discloses a carbazole derivative based on epoxybutane and a preparation method and application thereof, the carbazole derivative based on epoxybutane is a crosslinkable compound with hole transport capability, and the carbazole hole transport material based on epoxybutane has hole transport performance and high triplet energy. The cross-linkable epoxybutane is introduced, so that the material has relatively high thermal stability and solvent resistance; the prepared carbazole hole transport material based on epoxybutane is introduced into an organic semiconductor device, especially an organic light-emitting device as a hole transport layer, and the solvent resistance and hole transport capacity of the hole transport layer can be improved.

Description

technical field [0001] The invention belongs to the field of organic optoelectronics, and relates to a class of carbazole derivatives based on butylene oxide, a preparation method thereof, and an application thereof as a hole transport layer material of an organic semiconductor device. [0002] technical background [0003] Organic semiconductor devices, such as organic light emitting diodes (Organic Light Emitting Diode, OLED) can also be called organic light-emitting semiconductors, which have outstanding advantages such as self-luminescence, high contrast, low energy consumption, wide viewing angle, and instant response. They are widely used For high-quality lighting devices and high-performance display devices, in the prior art, the main preparation methods of OLEDs are solution method and vacuum evaporation method. On the one hand, vacuum evaporation produces dense and uniform films, the film thickness can be precisely controlled, and the material selection is less restr...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D405/14C07D413/14C07D417/14H01L51/54H01L51/50
CPCC07D405/14C07D413/14C07D417/14H10K85/653H10K85/631H10K85/657H10K85/6572H10K50/15Y02E10/549
Inventor 叶尚辉景彤彤张攀峰陈智恒唐星星李宇鹏黄维
Owner NANJING UNIV OF POSTS & TELECOMM
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