Carbazole-N-yldistyryltriphenylamine derivative hole-transport material and preparation method thereof

A technology of distyryl triphenylamine and hole transport material, which is applied in the field of carbazole-N-based distyryl triphenylamine derivative hole transport material and preparation thereof, and can solve the problem that cannot meet the practical application of optoelectronic devices , poor solubility of styrene materials, low glass transition temperature and other problems, to achieve the effect of high yield, convenient purification and low cost

Inactive Publication Date: 2019-05-21
TIANJIN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] The styrene structure has a large conjugated structure and strong carrier transport ability, and is often used as the core group of optoelectronic materials; but the solubility of styrene materials is poor and the glass transition temperature is low, which cannot meet the practical application of optoelectronic devices; The carbazole triphenylamine material has good hole transport ability and thermal stability; the combination of styrene structure and carbazole triphenylamine group provides a new method for the development of hole transport materials with high hole mobility and thermal stability. new ideas

Method used

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  • Carbazole-N-yldistyryltriphenylamine derivative hole-transport material and preparation method thereof
  • Carbazole-N-yldistyryltriphenylamine derivative hole-transport material and preparation method thereof
  • Carbazole-N-yldistyryltriphenylamine derivative hole-transport material and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

example 1

[0034] The synthesis of example 1 methyl trianilino styrene carbazole

[0035] (1) Synthesis of Benzophenone Carbazole

[0036] N 2 Under protection, add carbazole (16.71g, 0.1mol) to a 250ml four-neck round bottom flask, add 150ml of anhydrous DMF as a solvent, then add potassium tert-butoxide (9.8g, 0.12mol), and heat to 65°C in an oil bath , stirred for 10 min. Add 4,4'-difluorobenzophenone (10.93 g, 0.5 mol) to the reactant and react at 65° C. for 12 h. Cool to room temperature, pour into ice-water mixture at 0 °C, filter, and wash three times with deionized water. Dry to give crude product. The crude product was recrystallized with acetone to obtain 24.13 g of a yellow-green solid with a yield of 94.1%.

[0037] 1 H NMR (400MHz, CDCl 3 )δ8.20(q, 2H), δ7.87–7.82(d, 1H), δ7.60(d, 1H), δ7.547.43(t, 1H), δ7.36(t, 1H)

[0038]

[0039] (2) Synthesis of Methyltrianiline Phosphate Ylide Salt

[0040] N 2 Under protection, in the 100mL four-neck flask, add methyltrip...

example 2

[0047] The synthesis of example 2 methyltriphenylamine styrene methyl carbazole

[0048] The synthesis of example 2 refers to the synthetic method of example 1, and the carbazole used is a methyl-substituted carbazole, and the color of the pure product is light yellow, and the productive rate is 71.2%.

[0049] The ratio of methylcarbazole, potassium tert-butoxide and 4,4'-difluorobenzophenone is: 3:3:1

[0050] The ratio of methylcarbazolylbenzophenone, sodium tert-butoxide and triphenylamine ylide salt is: 3:7:1

[0051]

example 3

[0052] Synthesis of Example 3 Isopropyltriphenylamineethylene Isopropylcarbazole

[0053] The synthesis of example 3 refers to the synthetic method of example 1, and the carbazole used is isopropyl substituted carbazole, and the color of pure product is pale yellow, and productive rate is 71.2%

[0054] The ratio of tert-butylcarbazole, potassium tert-butoxide and 4,4'-difluorobenzophenone is: 3:3:1

[0055] The ratio of isopropyltriphenylamine benzyl alcohol to triphenylphosphine hydrobromide is: 1:2

[0056] The ratio of tert-butylcarbazophenone, sodium tert-butoxide and triphenylamine ylide salt is: 2:6:1

[0057]

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Abstract

The invention relates to a carbazole-N-yldistyryltriphenylamine derivative hole-transport material and a preparation method thereof. The structural formula of the transport material is as shown in thespecification, wherein R is H or C1-10 branched or linear alkyl, C1-10 alkoxy, vinyl, diphenylamine and carbazolyl. The invention overcomes defects of existing styrene materials and provides a novelstyrene carbazole triphenylamine hole-transport material (HTM). The material has adjustable HOMO, LUMO energy level, high glass transition temperature and excellent hole-transport performance. The material can be used in organic light emitting diodes and also can be used in perovskite solar cells and organic field effect transistors.

Description

technical field [0001] The invention relates to the field of organic photoelectric luminescence, in particular to a carbazole-N-yldistyryltriphenylamine derivative hole transport material and a preparation method thereof. Background technique [0002] Organic light-emitting diode (OLED) display has the advantages of self-illumination, wide viewing angle, fast response time, low operating voltage, thin panel thickness, large-size bendable flexible panel, and low-cost potential. It has attracted the continuous attention of researchers and has been widely used in the fields of solid-state lighting and flat panel display. [0003] OLED devices are composed of electrode materials and multilayer organic functional materials. The organic functional layer materials mainly include hole transport materials (HTM), light emitting materials (EM), electron transport materials (ETM) and so on. The role of hole transport materials in OLED devices is to improve the flatness of the anode sur...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D209/86C07D209/88H01L51/54H01L51/50
Inventor 李祥高朱红伟王世荣刘红丽董晓菲
Owner TIANJIN UNIV
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