Blue fluorescent compound comprising double fluorescence groups and preparation method and application of blue fluorescent compound

A blue fluorescence, dual chromophore technology, applied in the field of organic electroluminescence display, can solve the problems of reducing the stability of phosphorescent dyes, decreasing the luminous quantum efficiency, increasing the non-radiative transition rate, etc.

Inactive Publication Date: 2016-05-25
SHANGQIU NORMAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

At present, among the three primary colors of red, green, and blue, the performance of red and green Ir(III) complex phosphorescent materials has met the requirements of OLED industrialization, while the development of blue phosphorescent materials is not ideal (Chemical Progress, 2010,22:2255-2267), the main reasons are: on the one hand, for phosphorescent dyes, adjusting the blue-shift of the luminescent wavelength will lead to an increase in the non-radiative transition rate, thereby reducing the quantum efficiency of luminescence; on the other hand, adjusting the phosphorescent The blue shift of dye emission often requires the introduction of fluorine atoms with high electronegativity, and the introduction of fluorine atoms will reduce the stability of such phosphorescent dyes. These problems seriously hinder the application of OLEDs in the fields of full-color flat panel displays and solid-state white lighting.

Method used

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  • Blue fluorescent compound comprising double fluorescence groups and preparation method and application of blue fluorescent compound
  • Blue fluorescent compound comprising double fluorescence groups and preparation method and application of blue fluorescent compound
  • Blue fluorescent compound comprising double fluorescence groups and preparation method and application of blue fluorescent compound

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Embodiment 1

[0025] Synthesis of compound B1:

[0026]Dissolve 1.00 g (4.8 mmol) of 9,10-phenanthrenequinone, 0.99 g (4.8 mmol) of 9-anthracenaldehyde, 0.92 ml (5.8 mmol) of 4-tert-butylaniline and 4.57 g (59.3 mmol) of ammonium acetate in 50 ml In glacial acetic acid, reflux at 120°C for 24 hours under nitrogen protection. Cool to room temperature, pour the reaction solution into methanol, filter with suction, and then separate by column chromatography (eluent is dichloromethane / petroleum ether=2:1) ​​to obtain the corresponding compound 2-(9-anthracenyl)-1-( 4-tert-butylphenyl)-1H-phenanthrene[9,10-d]imidazole (B1), yield 53%. Synthesize according to the following equation:

[0027]

[0028] Compound by 1 HNMR, mass spectrometry, and elemental analysis have been verified, and the results show that the structure is correct, and the data are as follows:

[0029] 1 HNMR (400MHz, CDCl 3 ,ppm):8.91–8.77(m,3H),8.46(s,1H),7.97–7.95(m,2H),7.74–7.67(m,4H),7.55(t,J=8Hzand4Hz,1H),7.41 (t,...

Embodiment 2

[0034] Synthesis of compound B2:

[0035] Dissolve 1.00 g (4.8 mmol) of 9,10-phenanthrenequinone, 1.10 g (4.8 mmol) of 1-pyrene carboxaldehyde, 0.92 ml (5.8 mmol) of 4-tert-butylaniline and 4.57 g (59.3 mmol) of ammonium acetate in 50 ml In glacial acetic acid, reflux at 120°C for 24 hours under nitrogen protection. Cooled to room temperature, the reaction solution was poured into methanol, suction filtered, and then column chromatography (eluent was dichloromethane / petroleum ether=2:1) ​​to obtain the corresponding compound 2-(1-pyrenyl)-1-( 4-tert-butylphenyl)-1H-phenanthrene[9,10-d]imidazole (B2), yield 74%. Synthesize according to the following equation:

[0036]

[0037] Compound by 1 HNMR, mass spectrometry, and elemental analysis have been verified, and the results show that the structure is correct, and the data are as follows:

[0038] 1 HNMR (400MHz, CDCl 3 ,ppm):8.94(d,J=8Hz,1H),8.84-8.76(m,2H),8.33(d,J=8Hz,1H),8.20(d,J=4Hz,2H),8.11-8.00( m,5H),7.93(d,J=8H...

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Abstract

The invention discloses a blue fluorescent compound comprising double fluorescence groups. The blue fluorescent compound is 2-(9-anthryl)-1-(4-tert-butylphenyl) 1H-phenanthro [9,10-d] imidazole; 2-(1-pyrenyl)-1-(4-tert-butylphenyl) 1H-phenanthro [9,10-d] imidazole. The maximum emission peak of an electroluminescent device (D1) based on dye B1 is located at 460 nm, the chromaticity coordinate is (CIE, x=0.16, and y=0.17), the light is blue light, and the device maximum luminance, the current efficiency and the external quantum efficiency are 5168.4 cd/m<2>, 1.15 cd/A and 0.83% respectively. The maximum emission peak of an electroluminescent device (D2) based on dye B2 is located at 448 nm, the chromaticity coordinate is (CIE, x=0.15, and y=0.12), the light is blue light, and the device maximum luminance, the current efficiency and the external quantum efficiency are 5188.0 cd/m<2>, 0.90 cd/A and 0.85% respectively. The luminous efficiency of the device is reduced remarkably with the increasing of the luminance, which shows weak efficiency roll-off.

Description

technical field [0001] The invention relates to an organic electroluminescence material and its application in an organic electroluminescence device, belonging to the technical field of organic electroluminescence display. Background technique [0002] Organic Light-Emitting Diodes (Organic Light-Emitting Diodes, hereinafter referred to as OLEDs) are widely used in various fields due to their ultra-thin, fast response, self-luminescence, full curing, good temperature characteristics, and flexible display. [0003] In 1963, Pope et al. (J.Chem.Phys.1963,38:2042-2043) studied blue electroluminescent devices based on anthracene single crystal wafers (10-20 μm). Due to the restriction of electrode materials (silver colloid and sodium chloride solution), the luminous starting voltage of the device is as high as 400V, and the efficiency and brightness are low. However, the discovery opens up a new field of light-emitting technology. Over the next two decades, OLED research progr...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C09K11/06C07D235/02H01L51/54
CPCC09K11/06C07D235/02C09K2211/1044H10K85/00
Inventor 张付力李素芝翟滨曹广秀刘双
Owner SHANGQIU NORMAL UNIVERSITY
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