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Pyroimidazole derivative, preparation method thereof and electroluminescent device

An electroluminescent device and technology of imidazole derivatives, applied in the field of organic electroluminescence, can solve the problems of no light emission, reduction of luminous efficiency, quenching, etc., and achieve strong fluorescence properties, simple synthesis method, and wide application range

Active Publication Date: 2015-05-06
JILIN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

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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  • Pyroimidazole derivative, preparation method thereof and electroluminescent device
  • Pyroimidazole derivative, preparation method thereof and electroluminescent device
  • Pyroimidazole derivative, preparation method thereof and electroluminescent device

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0028] Example 1: cis-1,1'-2phenyl-2,2'-2tetraphenylethenyl-4,5,9,10-pyrenimidazole (M1)

[0029]

Embodiment 2

[0030] Example 2: trans-1,1'-2phenyl-2,2'-2tetraphenylethenyl-4,5,9,10-pyrenimidazole (M2)

[0031]

[0032] 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%. Such as 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...

Embodiment 3

[0034] Embodiment 3: the preparation of electroluminescent device

[0035] Such as 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).

[0036] 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 met...

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Abstract

The invention provides a pyroimidazole derivative. The pyroimidazole derivative has a structure shown in the specification. The invention also provides a preparation method of the pyroimidazole derivative, belonging to the technical field of organic electroluminescence. The bipolar pyroimidazole derivative is a fluorescence emitting material with a bipolar carrier transport property and contains a unit with a hole transport property and a unit with an electron transport property. The compound is simple in synthesis method and is suitable to apply widely. The material has a bipolar carrier transport property, can individually serve as a light emitting layer or a carrier transport layer and can be also mixed with other dyes and serve as the light emitting layer or the carrier transport layer. The compound shows stronger fluorescent properties in a solid state, can form uniform films and has better 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 Applications(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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