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Cyclic arylamine as hole transferring material with high vitrification point and its synthesis process

A hole transport material and high vitrification technology, applied in chemical instruments and methods, luminescent materials, organic chemistry, etc.

Inactive Publication Date: 2007-12-19
NANCHANG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] It can be seen that the above-mentioned existing hole-transporting materials obviously still have deficiencies and defects, and need to be further improved urgently.

Method used

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  • Cyclic arylamine as hole transferring material with high vitrification point and its synthesis process
  • Cyclic arylamine as hole transferring material with high vitrification point and its synthesis process
  • Cyclic arylamine as hole transferring material with high vitrification point and its synthesis process

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0025] A cyclic aromatic amine compound (abbreviated as CAA), its structural formula is:

[0026]

[0027] Its synthetic method is: in 250 milliliters of three-neck flasks, add 50 milliliters of o-xylenes, add N, N '-diphenyl-p-phenylenediamine (5mmol), m-dibromobenzene (5mmol), sodium tert-butoxide ( 12mmol), then add catalyst palladium acetate (0.02mmol) and tri-tert-butylphosphine (0.025mmol), and reflux at 130°C for 12 hours. After the reaction, the solvent was distilled off under reduced pressure, and the residue was recrystallized from tetrahydrofuran, separated by column chromatography with toluene as the eluent, and then sublimated by gradient to obtain the pure product. NMR analysis 1 H NMR (400MHz, CDCl 3 ), the results are: 7.26-7.20 (m, 18H), 6.70 (s, 6H), 6.86 (s, 7H), 6.67 (s, 3H), 6.33 (s, 2H). The elemental analysis result of this compound (molecular formula is C 48 h 36 N 4 ): Theoretical value: C, 86.20; H, 5.42; N, 8.38. Tested value: C, 86.26; H, 5...

Embodiment 2

[0029] N, N'-diphenyl substituted cyclic aromatic amine compounds, its structural formula is:

[0030]

[0031] Its synthesis method is: add 50 milliliters of o-xylene in 250 milliliters of three-neck bottles, add N, N'-bis(4-N, N'-diphenylphenyl)-p-phenylenediamine (5mmol), N, N- diphenyl substituted m-dibromobenzene (5mmol), sodium tert-butoxide (12mmol), then add catalyst palladium acetate (0.02mmol) and tri-tert-butylphosphine (0.025mmol), and reflux at 130°C for 12 hours. After the reaction, the solvent was distilled off under reduced pressure, and the residue was recrystallized from tetrahydrofuran, separated by column chromatography using toluene as the eluent, and then sublimated by gradient to obtain the pure product. Elemental analysis (molecular formula is C 120 h 90 N 10 ): Theoretical value: C, 86.23; H, 5.39; N, 8.38. Tested value: C, 86.25; H, 5.37; N, 8.42.

Embodiment 3

[0033] Its structural formula is:

[0034]

[0035] Its synthetic method is: in 250 milliliters three-neck flasks, add 50 milliliters of o-xylenes, add N, N '-diphenyl-m-phenylenediamine (5mmol), m-dibromobenzene (5mmol), sodium tert-butoxide ( 12mmol), then add catalyst palladium acetate (0.02mmol) and tri-tert-butylphosphine (0.025mmol), and reflux at 130°C for 12 hours. After the reaction, the solvent was distilled off under reduced pressure, and the residue was recrystallized from tetrahydrofuran, separated by column chromatography using toluene as the eluent, and then sublimated by gradient to obtain the pure product.

[0036] The elemental analysis result of this compound (molecular formula is C 48 h 36 N 4): Theoretical value: C, 86.23; H, 5.39; N, 8.38. Tested value: C, 86.58; H, 5.46; N, 8.60.

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Abstract

The present invention relates to cyclic arylamine as hole transferring material with high vitrification point and its synthesis process. The hole transferring material is prepared with N, N' -diphenyl-p-phenylene diamine or its derivative and m-dibromo benzene as material, or N, N' -diphenyl-m-phenylene diamine or its derivative as material, and one-xylene as solvent, and through reflux reaction with tert-butyl alcohol sodium under the protection of nitrogen and the catalysis of palladium acetate and tert-butyl phosphorus at 130-160 deg.c to obtain coarse product, and the subsequent purification to obtain pure product. The cyclic arylamine may be applied as hole transferring material in organic electroluminescent device.

Description

technical field [0001] The invention relates to a cyclic aromatic amine hole transport material with high glass transition temperature and a synthesis method. Background technique [0002] Organic electroluminescent technology has become a popular technology for the new generation of display technology due to its wide range of material choices, low energy consumption, wide viewing angle, ultra-thin large screen, bright colors, and fast response. It is currently on the eve of large-scale marketization. The main problem is that the stability of the device is not high enough. The important factor limiting the stability of the device is the thermal stability of the material. Among them, the thermal stability of hole transport materials is lower than that of light emitting materials and electron transport materials. At present, the most widely used are aromatic amine organic small molecule compounds as hole transport materials. Others such as carbazole derivatives, helical co...

Claims

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Application Information

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IPC IPC(8): C07D257/10C09K11/06H01L51/50H01L51/54
Inventor 高希存徐敏杨长剑
Owner NANCHANG UNIV
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