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Organic small molecule hole transport material, preparation method and application thereof

A technology of hole transport materials and small molecules, which is applied in the field of organic small molecule hole transport materials and their preparation, can solve the problems such as the need to improve the luminous efficiency, and achieve the effects of excellent solubility, simple preparation method, and large steric hindrance

Active Publication Date: 2021-04-23
CHINA PETROLEUM & CHEM CORP
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005]Literature reports (Organic Electronics, 2017, Vol. Methyl-N-[4-(9-phenyl-9H-carbazol-3-yl)phenyl]-9H-fluorene-2-amine (BCFN) was introduced into blue light-emitting polymer electroluminescence with polyfluorene as the light-emitting layer In light emitting devices, the performance is improved, but the maximum lumen efficiency is only 4.31cd A-1
Blue light electroluminescent efficiency still needs to be improved

Method used

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  • Organic small molecule hole transport material, preparation method and application thereof
  • Organic small molecule hole transport material, preparation method and application thereof
  • Organic small molecule hole transport material, preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0041] Preparation of small molecules M1-3

[0042] (1) N,N-bis(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)aniline (M1-1) synthesis:

[0043] Under argon atmosphere, 4,4-dibromotriphenylamine (1.00g, 2.48mmol), biboronic acid pinacol ester (1.89g, 7.44mmol), potassium acetate (1.46g, 14.89mmol), catalyst 1,1 '-bis(diphenylphosphino)ferrocenepalladium dichloride (Pd(dppf)Cl 2) (0.054g, 0.074mmol) was dissolved in 1,4-dioxane (20ml), heated to reflux, and reacted for 24h under reflux conditions; the solvent and potassium acetate were removed, purified by silica gel column chromatography, and the eluent Petroleum ether / dichloromethane=3 / 1 (volume ratio), and then recrystallized in tetrahydrofuran / ethanol to obtain a white powder (M1-1). 1 HNMR, 13 CNMR, MS and elemental analysis results show that the obtained compound is the target product, and the chemical reaction equation of the preparation process is as follows:

[0044]

[0045] (2) N-phenyl-4-(9-phenyl-9H...

Embodiment 2

[0053] Preparation of Polymer M2-3

[0054] (1) 4-methyl-N, N-bis(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)aniline ( Synthesis of M2-1):

[0055] Under argon atmosphere, 4-bromo-N-(4-bromophenyl)-N-(p-tolyl)aniline (1.00g, 2.40mmol), biboronic acid pinacol ester (1.83g, 7.19mmol), Potassium acetate (1.41 g, 14.38 mmol), catalyst 1,1'-bis(diphenylphosphino)ferrocenepalladium dichloride (Pd(dppf)Cl 2 ) (0.052g, 0.072mmol) was dissolved in 1,4-dioxane (20ml), heated to reflux, and reacted for 24h under reflux conditions; the solvent and potassium acetate were removed, purified by silica gel column chromatography, and the eluent Petroleum ether / dichloromethane=3 / 1 (volume ratio), and then recrystallized in tetrahydrofuran / ethanol to obtain a white powder (M2-1). 1 HNMR, 13 CNMR, MS and elemental analysis results show that the obtained compound is the target product, and the chemical reaction equation of the preparation process is as follows:

[0056]

[0057] ...

Embodiment 3

[0064] Preparation of small molecule M3-3

[0065] (1) 4-methoxy-N,N-bis(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)aniline Synthesis of (M3-1):

[0066] Under argon atmosphere, 4-bromo-N-(4-bromophenyl)-N-(4-methoxyphenyl)aniline (1.00g, 2.31mmol), biboronic acid pinacol ester (1.76g, 6.93mmol), potassium acetate (1.36g, 13.86mmol), catalyst 1,1'-bis(diphenylphosphino)ferrocenepalladium dichloride (Pd(dppf)Cl 2 ) (0.051g, 0.069mmol) was dissolved in 1,4-dioxane (20ml), heated to reflux, and reacted for 24h under reflux conditions; the solvent and potassium acetate were removed, purified by silica gel column chromatography, and the eluent Petroleum ether / dichloromethane=3 / 1 (volume ratio), and then recrystallized in tetrahydrofuran / ethanol to obtain a white powder (M3-1). 1 HNMR, 13 CNMR, MS and elemental analysis results show that the obtained compound is the target product, and the chemical reaction equation of the preparation process is as follows:

[0067] ...

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PUM

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Abstract

The invention belongs to the technical field of organic photoelectric materials, and discloses an organic small molecule hole transport material, a preparation method and application thereof. The structural formula of the small molecule hole transport material is shown as a formula (I). The invention also discloses a preparation method of the small molecule hole transport material, and the preparation method is simple and can be used for large-scale production. The small molecule hole transport material is large in steric hindrance, excellent in solubility and good in film forming quality, hole injection and transport are facilitated, and the turn-on voltage of a device is reduced; moreover, the maximum luminous efficiency of an OLED device taking the small molecule material as a hole transport layer can reach 11.0 candela / ampere, and excellent electroluminescent performance is shown.

Description

technical field [0001] The invention belongs to the technical field of organic photoelectric materials, and in particular relates to a class of organic small molecule hole-transporting materials and a preparation method and application thereof. Background technique [0002] In recent years, organic / polymer light-emitting diodes (O / PLEDs) have gradually entered the public's field of vision, and OLEDs are mainly used in two major fields of display and lighting. In the field of display, compared with liquid crystal displays, OLED displays have the advantages of active light emission, no backplane, high contrast, wide viewing angle, fast response speed, low driving voltage, and wide operating temperature range. In the field of lighting, OLED light sources do not contain ultraviolet radiation, do not cause glare, and do not contain mercury in the device structure, which is a green and healthy light source. The many advantages in display and lighting field make OLED become the fo...

Claims

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Application Information

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IPC IPC(8): C07D209/86H01L51/50H01L51/54
CPCC07D209/86H10K85/146H10K85/633H10K85/6572H10K50/15Y02E10/549
Inventor 应磊郭婷石林瑞胡黎文曹镛
Owner CHINA PETROLEUM & CHEM CORP
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