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Preparation method of bisbenzimidazole group-containing phenanthroline-type derivative and organic light-emitting device (OLED)

A technology of dibenzimidazolyl phenanthrene and benzimidazolyl phenanthrene, which is applied in the field of organic optoelectronic materials, can solve problems such as no synthesis method, and achieve the effects of good solubility, excellent thermal stability and high glass transition temperature

Inactive Publication Date: 2015-07-08
JILIN OPTICAL & ELECTRONICS MATERIALS
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

There are also some related literatures that propose similar structures, but there is no corresponding synthesis method

Method used

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  • Preparation method of bisbenzimidazole group-containing phenanthroline-type derivative and organic light-emitting device (OLED)
  • Preparation method of bisbenzimidazole group-containing phenanthroline-type derivative and organic light-emitting device (OLED)
  • Preparation method of bisbenzimidazole group-containing phenanthroline-type derivative and organic light-emitting device (OLED)

Examples

Experimental program
Comparison scheme
Effect test

Synthetic example

[0044]

[0045] Add 20.8g (0.1mol) 4,7-dimethyl-1,10-phenanthroline and 49.9g (0.45mol) selenium dioxide to a 5L three-necked flask, add to the mixture of 1300ml dioxane and 55ml water Solution, temperature raised to 100°C, reflux reaction for 3-4 hours, use TLC method to determine the end of the reaction, stop the reaction, pass it through the diatomaceous earth funnel while it is hot, and solid precipitates after cooling, tetrahydrofuran recrystallization to obtain dialdehyde compounds 19.1 g (0.081 mol) of yellow crystals, yield 81%.

[0046] In a 1L three-necked flask, put 19g (0.08mol) of the above dialdehyde compound, 36.6g (0.2mol) of o-aminodiphenylamine, and 38g (0.2mol) of sodium metabisulfite in 400ml of DMF, and reflux for overnight reaction. After the reaction was detected by TLC, cool to room temperature, washed with water, extracted with ethyl acetate, and recrystallized to obtain 33.9 g (0.06 mol) of a white solid with a yield of 75%.

[0047] Synthesis exa...

Embodiment 1

[0064] Measuring Example 1: Luminescent Properties of Compounds of Formula (I), Formula (II) and Comparative Samples

[0065] Under the same conditions, the samples of Comparative Example 1 and the samples of the application examples formula (I) and formula (II) were measured. The measurement uses the KEITHLEY Keithley 235 source measurement unit, Spectrascan PR650 Spectrum scanning colorimeter to evaluate driving voltage, luminous brightness, luminous efficiency, and luminous color. The results are listed in Table 2:

[0066] Table 2

[0067]

[0068] According to Table 2, the above-mentioned samples exhibit blue emission color in the wavelength range of 460-480nm. Compared with the sample of Comparative Example 1 using the sample of Example 1, the organic light emitting device using the organic layer of the dibenzoimidazolylphenanthroline derivative may have lower driving voltage, higher luminance, and higher efficiency.

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Abstract

The invention provides a bisbenzimidazole group-containing phenanthroline-type organic semiconductor material, which is excellent in thermo-stability, solubility and film-forming property. An optical-spectrum test proves that the maximum light-emitting wavelength of the material is in the range of blue light. Meanwhile, because that the structure of the light-emitting material contains phenanthroline and two bisbenzimidazole groups, the light-emitting material is good in symmetry, excellent in charge transfer capacity and high in glass-transition temperature. In addition, a crystallization effect can be prevented.

Description

technical field [0001] The invention relates to the field of organic photoelectric materials, in particular to a class of dibenzimidazolylphenanthroline derivatives, a preparation method and an organic light-emitting device. Background technique [0002] Organic electroluminescent (EL) devices (hereinafter, simply referred to as "organic EL devices"). It generally consists of two opposing electrodes and at least one layer of organic light-emitting compound interposed between the two electrodes. Charges are injected into the organic layer formed between the anode and cathode to form electron and hole pairs, which cause light emission from organic compounds having fluorescent or phosphorescent properties. [0003] With the development of the information age, organic electroluminescent flat panel displays (OLEDs) with high efficiency, energy saving and light weight and large-area white light illumination have attracted more and more attention. OLED technology has attracted ...

Claims

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Application Information

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IPC IPC(8): C07D471/04C09K11/06H01L51/54
Inventor 高春吉汪康李文军
Owner JILIN OPTICAL & ELECTRONICS MATERIALS
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