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Indenoimidazole compound, material comprising the indenoimidazole compound, and organic electroluminescent device

An electroluminescent device, indenimidazole technology, applied in the field of organic electroluminescent materials

Active Publication Date: 2020-06-02
SHIJIAZHUANG CHENGZHI YONGHUA DISPLAY MATERIALS CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In recent years, organic electroluminescent display technology has become mature, and some products have entered the market. However, in the process of industrialization, there are still many problems to be solved, especially the various organic materials used to make devices. Injection, transmission performance, material electroluminescence performance, service life, color purity, matching between various materials and electrodes, etc., there are still many problems that have not yet been resolved.

Method used

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  • Indenoimidazole compound, material comprising the indenoimidazole compound, and organic electroluminescent device
  • Indenoimidazole compound, material comprising the indenoimidazole compound, and organic electroluminescent device
  • Indenoimidazole compound, material comprising the indenoimidazole compound, and organic electroluminescent device

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0084] The structural formula of compound CJH-P16 is shown in the following formula:

[0085]

[0086] Its preparation route is as follows:

[0087] The first step: preparation of intermediate Int.-2

[0088]

[0089] 15g (54.5mmol) of 4-bromo-N-phenylbenzamidine Int.-1 and 9.4g (45.5mmol) of chalcone, 1.5g of anhydrous ferric chloride, then add 1.2g of iodine, add 80ml of dichlorobenzene, fed with oxygen, heated to 110°C and stirred for 8 hours, cooled to room temperature, poured the reaction solution into 800ml of petroleum ether, filtered, washed the filter cake with petroleum ether, and recrystallized with ethanol to obtain 16g of yellow solid Int.-2, yield 75%.

[0090] The second step: the preparation of intermediate Int.-3

[0091]

[0092] 15g (31.3mmol) of intermediate Int.-2 was dissolved in 150ml of anhydrous tetrahydrofuran, under the protection of nitrogen, 46.9mmol of phenylmagnesium bromide in tetrahydrofuran was added dropwise, stirred at room tempe...

Embodiment 2

[0104] The structural formula of compound CJH-P48 is shown in the following formula:

[0105]

[0106] Its preparation route is as follows:

[0107] The first step: preparation of intermediate Int.-5

[0108]

[0109] The synthetic operation refers to the second step of Example 1, and replaces the phenylmagnesium bromide in the second step of Example 1 with methylmagnesium iodide to obtain the intermediate Int.-5, a black oil, with a yield of 88%.

[0110] The second step: the preparation of intermediate Int.-6

[0111]

[0112] The synthesis operation refers to the third step of Example 1, and the intermediate Int.-3 in the third step of Example 1 is replaced by the intermediate Int.-5 to obtain the intermediate Int.-6, a black oil, and the yield is 58 %.

[0113] The third step: the preparation of product CJH-P48

[0114]

[0115] 5g (10.4mmol) of intermediate Int.-6, 4g (12.5mmol) of (4-(1-phenyl-1H-benzo[d]imidazole-2-phenyl) boronic acid, 2.2g (20.8mmol) ...

Embodiment 3

[0120] The structural formula of compound CJH-P60 is shown in the following formula:

[0121]

[0122] Its preparation route is as follows:

[0123] The first step: preparation of intermediate Int.-8

[0124]

[0125] The synthesis operation refers to the first step of Example 1, and the chalcone in the first step of Example 1 is replaced by the intermediate Int.-7 to obtain the intermediate Int.-8 as a yellow solid with a yield of 56%.

[0126] The second step: the preparation of intermediate Int.-9

[0127]

[0128] The synthetic operation refers to the second step of Example 1, replace the phenylmagnesium bromide in the second step of Example 1 with methylmagnesium iodide, and replace the intermediate Int.-2 in the second step of Example 1 with intermediate Int.-8, the intermediate Int.-9 was obtained as a black oil, and the yield was 87%.

[0129] The third step: the preparation of intermediate Int.-10

[0130]

[0131] Dissolve the intermediate Int.-9 prep...

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Abstract

The invention discloses indenoimidazole compounds; the structural formula of the indenoimidazole compounds is as shown in a formula I, and the formula I is described in the description. The inventionalso discloses materials containing the indenoimidazole compounds, and an organic light-emitting device (OLED) containing the indenoimidazole compounds. The indenoimidazole compounds provided by the invention have excellent current carrier transport capability; the OLED prepared from the materials provided by the invention can obviously reduce starting voltage and improve luminous efficiency and brightness; the indenoimidazole compounds have the characteristics of better film-forming property, simple material synthesis and purification methods, suitability for large-scale production, and the like, thus being an ideal choice for electronic transmission materials of the OLED.

Description

technical field [0001] The invention relates to the technical field of organic electroluminescent materials. More specifically, it relates to indenoimidazole derivatives, materials containing the indenoimidazole compounds, and organic electroluminescent devices. Background technique [0002] Organic electroluminescence (referred to as OLED) and related research As early as 1963, pope et al. first discovered the electroluminescence phenomenon of organic compound single crystal anthracene. In 1987, Kodak Corporation of the United States made an amorphous film device by evaporating organic small molecules, which reduced the driving voltage to less than 20V. This type of device is ultra-thin, fully cured, self-illuminating, high brightness, wide viewing angle, fast response, low driving voltage, low power consumption, bright color, high contrast, simple process, good temperature characteristics, and can realize flexible display And other advantages, can be widely used in flat ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D401/14C07D403/10C07D401/10C07D235/02C07D405/10C07D409/10C07D471/04C07D471/14C07D487/04C07D417/10C07D413/14C07D405/14C07F7/08C07F9/6506H01L51/54
Inventor 曹建华隋岩董梁王士波华瑞茂
Owner SHIJIAZHUANG CHENGZHI YONGHUA DISPLAY MATERIALS CO LTD
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