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Pyrene imidazole derivatives, preparation method thereof, and electroluminescent device

An electroluminescent device and imidazole derivative technology, applied in the field of organic electroluminescence, can solve the problems of reduced luminous efficiency, non-luminescence, quenching and the like, and achieve the effects of simple synthesis method, strong fluorescence properties and wide application range

Active Publication Date: 2020-04-14
JILIN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0005] There is generally a problem in organic electroluminescent materials: most organic light-emitting materials have good luminous properties in solution state, but in the aggregated state, the luminous efficiency will be greatly reduced or even not luminous, that is, aggregation caused quenching (aggregation caused quenching). quenching, ACQ)
Ma Yuguang's research group designed and synthesized cis-DPDSB molecules, and believed that the two double bonds in the excited state of the molecule were restricted in twisting in the aggregated state, which prevented cis-trans isomerization, which was the reason for the enhanced solid-state luminescence.

Method used

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  • Pyrene imidazole derivatives, preparation method thereof, and electroluminescent device
  • Pyrene imidazole derivatives, preparation method thereof, and electroluminescent device
  • Pyrene imidazole derivatives, preparation method thereof, and electroluminescent device

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0029] Example 1: cis-1,1'-2phenyl-2,2'-2tetraphenylethenyl-4,5,9,10-pyrenimidazole (M1)

[0030]

Embodiment 2

[0031] Example 2: trans-1,1'-2phenyl-2,2'-2tetraphenylethenyl-4,5,9,10-pyrenimidazole (M2)

[0032]

[0033] Heat an appropriate amount of pyrenequinone (0.5g), tristyrylbenzaldehyde (1.6g), aniline (2ml) and ammonium acetate (1.5g) in 15ml of glacial acetic acid to reflux at 120°C for two hours, then stop heating and cool After reaching room temperature, filter to obtain dark green solid, adopt SiO 2 Column separation, dichloromethane:petroleum ether volume ratio of 1:1 and dichloromethane were successively purified through the column to obtain 0.45g of the green target product (Example 1), with a yield of 22%. like figure 1 As shown in (1), 1 H NMR (500MHz, d8-THF, ppm): 9.02(d,2H), 8.16(t,1H), 7.62(m,10H), 7.41(d,4H), 7.32(d,2H), 7.20(t ,1H), 7.12-7.03(m,18H), 7.03-6.97(m,12H), 6.93(d,4H). Mass spectrometry data (C 82 h 54 N 4 ) theoretical value: 1095.33; measured value: 1096.8. Elemental analysis (C 82 h 54 N 4 ) theoretical value: C: 89.92; H: 4.97; N: 5.12...

Embodiment 3

[0035] Embodiment 3: the preparation of electroluminescent device

[0036] like figure 2 The device structure shown includes: a substrate layer 1 , a hole injection layer 2 , a hole transport layer 3 , a light emitting layer 4 , an electron transport layer 5 , and a cathode layer 6 . The substrate layer 1 is glass and the conductive layer attached to it is indium tin oxide (positive electrode, ITO, 40nm), the hole injection layer 2 is polyethylenedioxythiophene (PEDOT, 40nm), and the hole transport layer 3 is 4,4 '-bis(N-phenyl-N-naphthyl)-biphenyl (NPB, 40nm), the light emitting layer 4 is a pyrenimidazole compound (30nm), and the electron transport layer 5 is 1,3,5-tri(1 -Phenyl-1H-benzimidazol-2-yl)benzene (TPBi, 50nm), the cathode layer 6 is a metal layer (LiF / Al, 0.75nm / 100nm).

[0037] The electroluminescent device is prepared according to methods known in the art, such as the fabrication method disclosed in reference (Adv. Mater. 2003, 15, 277.). The specific method...

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Abstract

The present invention provides a pyrenimidazole derivative, which has the following structure: the present invention also provides a preparation method of the pyrenimidazole derivative. It belongs to the technical field of organic electroluminescence. Bipolar pyrenimidazole derivatives are fluorescent materials with bipolar carrier transport properties, which contain units with hole transport properties and units with electron transport properties. The synthesis method of the compound of the invention is simple and suitable for wide application. The material of the invention has bipolar carrier transport properties, and can be used alone as a light-emitting layer or a carrier transport layer, or can be doped with other dyes as a light-emitting layer or a carrier transport layer. The compound involved in the invention exhibits strong fluorescent properties in solid state, can form a uniform thin film, and has good optical and thermal stability.

Description

technical field [0001] The invention belongs to the technical field of organic electroluminescence, and in particular relates to a class of fluorescent luminescent materials with bipolar carrier transport properties—pyrene imidazole derivatives and their preparation methods and their use as electroluminescent materials in the field of electroluminescence Applications. Background technique [0002] Since Tang and Van Slyke (Appl.Phys.Lett.1987, 51(12).21) reported organic light emitting diodes (OLEDs) in 1987, the field of electroluminescence has been developed for more than 20 years. Great progress has been made in material systems, device applications and related theories. Organic thin-film electroluminescent devices have a series of advantages such as self-luminescence, low-voltage DC drive, full curing, wide viewing angle, and rich colors, and have broad application prospects. [0003] A typical structure of an OLED includes a cathode layer, an anode layer, and an organ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D487/04C09K11/06H01L51/54
CPCC09K11/06C07D487/04C09K2211/1044C09K2211/1007H10K85/6572
Inventor 路萍高曌刘豫龙
Owner JILIN UNIV
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