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9,10-phenanthroimidazole derivatives and use thereof as electroluminescent materials

A technology of phenanthroimidazole and derivatives, applied in the field of organic electroluminescence, can solve the problems of poor film-forming performance, easy crystallization, low luminous efficiency and the like

Inactive Publication Date: 2011-09-21
JILIN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The U.S. Patent No. 4,539,507 mentions the use of small-molecule organics as light-emitting materials, but small-molecule materials have many disadvantages, such as poor film-forming performance and easy crystallization, etc.
In recent years, the use of polymers as organic light-emitting materials has been studied, but the luminous efficiency of general polymers is lower than that of small molecule materials.

Method used

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  • 9,10-phenanthroimidazole derivatives and use thereof as electroluminescent materials
  • 9,10-phenanthroimidazole derivatives and use thereof as electroluminescent materials
  • 9,10-phenanthroimidazole derivatives and use thereof as electroluminescent materials

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0050] Example 1: 1,2-diphenyl substituted 9,10-phenanthroimidazole

[0051]

[0052] Heat an appropriate amount of phenanthrenequinone (2.0g), benzaldehyde (0.5ml), aniline (0.5ml) and ammonium acetate (8.0g) in 120ml of glacial acetic acid to reflux at 140°C for two hours, stop heating, and cool to room temperature Filtration afforded a white solid which was taken over SiO 2 Column separation, developing solvent is CH 2 Cl 2 , and purified to obtain the target product with a yield of 90.5%.

[0053] 1 H NMR (500MHz, DMSO, ppm): 8.93(d, J=8.2Hz, 1H), 8.75(d, J=8.5Hz, 1H), 8.69(d, J=7.6Hz, 1H), 7.78(t, J=7.6Hz, 7.0Hz, 1H), 7.73-7.65(m, 6H), 7.58(dd, J=7.9Hz, 2.1Hz, 2H), 7.55(t, J=7.0Hz, 7.3Hz, 1H), 7.39-7.30 (m, 4H), 7.08 (d, J=8.2Hz, 1H). Mass spectrometry data (C 27 h 18 N 2 ) theoretical value: 370.5; measured value: 370.2. Elemental analysis (C 27 h 18 N 2 ) Theoretical: C, 87.54; H, 4.90; N, 7.56. Found: C, 87.50; H, 4.92; N, 7.55.

[0054] It showed that...

Embodiment 2

[0055] Example 2: 4,4-bis-(1-phenyl-9,10-phenanthroimidazole)biphenyl

[0056]

[0057] Heat appropriate amount of phenanthrenequinone (2.0g), 4,4-disubstituted biphenyl dialdehyde (1.0g), aniline (0.5ml) and ammonium acetate (8.0g) in 120ml of glacial acetic acid to reflux at 140°C for 2 hours Afterwards, stop heating, filter after cooling to room temperature, obtain yellow-green solid, adopt SiO 2 Column separation, developing solvent is CH 2 Cl 2 , and purified to obtain the target product with a yield of 80.5%.

[0058] 1 H NMR (500MHz, DMSO, ppm): 8.94 (d, J = 8.5Hz, 2H), 8.89 (d, J = 8.2Hz, 2H), 8.72 (d, J = 8.2Hz, 2H), 7.80-7.65 ( m, 22H), 7.57 (t, J = 7.9Hz, 7.6Hz, 2H), 7.35 (t, J = 7.3Hz, 7.3Hz, 2H), 7.09 (d, J = 8.2Hz, 2H). Mass spectrometry data (C 54 h 34 N 4 ) theoretical value: 738.28; measured value: 739.0. Elemental analysis (C 54 h 34 N 4 ) Theoretical values: C, 87.78; H, 4.64; N, 7.58. Found: C, 87.80; H, 4.62; N, 7.57.

[0059] It showed th...

Embodiment 3

[0060] Example 3: 1,3,5-triphenyl-(1-phenyl-9,10-phenanthroimidazole)benzene

[0061]

[0062] Heat appropriate amount of phenanthrenequinone (2.0g), 1,3,5-triphenyl substituted trialdehyde (0.6g), aniline (1ml) and ammonium acetate (10g) in 120ml of glacial acetic acid to 140°C and reflux for two hours , stop heating, filter after cooling to room temperature, obtain a yellow-green solid, use SiO 2 Column separation, developing solvent is CH 2 Cl 2 , and purified to obtain the target product with a yield of 76.5%.

[0063] 1 H NMR (500MHz, DMSO, ppm): 8.93(d, J=8.8Hz, 3H), 8.88(d, J=7.3Hz, 3H), 8.72(d, J=7.6Hz, 3H), 7.98(s, 3H), 7.93(d, J=8.2Hz, 6H), 7.80-7.66(m, 27H), 7.57(t, J=7.9Hz, 7.6Hz, 3H), 7.35(t, J=8.2Hz, 7.3Hz , 3H), 7.09 (d, J = 7.9 Hz, 3H). Mass spectrometry data (C 87 h 54 N 6 ) Theoretical value: 1182.44; measured value: 1183.50. Elemental analysis (C 87 h 54 N 6 ) Theoretical values: C, 88.30; H, 4.60; N, 7.10. Found: C, 88.26; H, 4.60; N, 7.08....

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Abstract

The invention discloses 9,10-phenanthroimidazole derivatives and use thereof as electroluminescent materials, and belongs to the technical field of organic electroluminescence. The luminescent materials have the structural general formula as the description. A core group is 9,10-phenanthro4,5-1,3imidazole or derivatives; substituent groups R0-R8 are respectively selected from hydrogen, alkyl, hydroxyl, alkoxy, nitro, cyan, amino, sulfydryl, halogen atom, phenyl, tolyl, naphthyl, furyl, thienyl, pyrryl, pyridyl, pyranyl, quinolyl, indolyl, carbazolyl and aniline. The organic electroluminescent materials can be applied to luminous layers or carrier transmission layers in multi-layer organic electroluminescent devices.

Description

technical field [0001] The invention belongs to the technical field of organic electroluminescence, and in particular relates to a new type of organic light-emitting material, which can be used in flat panel display devices, light-emitting diodes and electronic imaging equipment. Background technique [0002] Today, with the development of multimedia technology and the advent of the information society, the requirements for flat panel display performance are getting higher and higher. Three new display technologies have emerged in recent years: plasma display, field emission display and organic electroluminescent display (OLED), all of which have made up for the shortcomings of cathode ray tubes and liquid crystal displays to a certain extent. Among them, organic thin-film EL devices have a series of advantages such as self-luminescence, low-voltage DC drive, full curing, wide viewing angle, and rich colors. Compared with liquid crystal displays, OLED does not require a back...

Claims

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Application Information

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IPC IPC(8): C07D235/02C07D403/10C07D403/14C07F7/10C07D409/14C09K11/06H01L51/54
Inventor 马於光路萍王志明高曌李维军刘贺
Owner JILIN UNIV
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