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Phenanthroimidazole symmetric derivative host material and electroluminescent device

A technology of phenanthroimidazole and host material, which is applied in the field of phenanthroimidazole symmetrical derivative host material and electroluminescent device, and can solve the problems of unsatisfactory luminous efficiency, lifetime and optical purity, etc.

Active Publication Date: 2015-10-21
NANJING TOPTO MATERIALS CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although the currently known OLED materials have greatly improved their performance, they have not yet achieved satisfactory luminous efficiency, lifetime and light purity.

Method used

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  • Phenanthroimidazole symmetric derivative host material and electroluminescent device
  • Phenanthroimidazole symmetric derivative host material and electroluminescent device
  • Phenanthroimidazole symmetric derivative host material and electroluminescent device

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0088] Embodiment 1: the preparation of compound G1

[0089] The first step: prepare intermediate A according to the following steps:

[0090]

[0091] (1) Synthesis of intermediate A-1:

[0092] Add 2.08g (0.01mol) phenanthrene-9,10 diketone, 2.04g (0.011mol) p-bromobenzaldehyde, 0.186g (0.02mol) aniline, 50ml acetic acid in a 100ml three-necked flask, add ammonium acetate dropwise under nitrogen protection After the addition was completed, the temperature was lowered to 25°C after 130°C reaction for 18 hours. The reaction solution was filtered, washed with water and saturated sodium bicarbonate to obtain 3.4 g of the product, hplc: 98%, yield: 76%.

[0093] (2) Synthesis of Intermediate A:

[0094] Add 9g of 2-(4-bromophenyl)-1-phenylphenanthroimidazole (0.02mol) into 150ml THF, cool down to -78°C, and drop 12ml (2.5M / L, 0.03mol ) n-BuLi, keep warm for 30 minutes, add 4.26g (0.041mol) trimethyl borate dropwise, finish the reaction after 2 hours of reaction, add 50ml o...

Embodiment 2

[0100] Embodiment 2: the preparation of compound G3

[0101] The preparation of the target compound G3 of this embodiment, its structural formula and synthetic route are as follows:

[0102]

[0103] Specifically, the preparation method of compound G3 includes:

[0104] (1) Intermediate A is prepared according to the same method as in Example 1;

[0105] (2) 8.28g (0.02mol) of intermediate A, 2.86g (0.01mol) of 1,4-dibromonaphthalene, 4.15g (0.03mol) of potassium carbonate, 50ml of toluene, 30ml of ethanol and 30ml of water were mixed, and the Next, add tetrakis(triphenylphosphine) palladium 0.23g (0.0002mol) to react, raise the temperature to reflux, point the plate to monitor until the reaction is complete, end the reaction, spin the reaction solution to dryness, add 100ml of dichloromethane, make it dissolve completely and Pass through a silica gel column, add 100ml of water to the filtrate, wash with water, separate the organic phase, spin it to dryness, boil it twice...

Embodiment 3

[0106] Embodiment 3: the preparation of compound G4

[0107] The preparation of the target compound G4 of this embodiment, its structural formula and synthetic route are as follows:

[0108]

[0109] Specifically, the preparation method of the compound G4 includes:

[0110] (1) Intermediate A is prepared according to the same method as in Example 1;

[0111] (2) 8.28g (0.02mol) of intermediate A, 2.86g (0.01mol) of 1,5-dibromonaphthalene, 4.15g (0.03mol) of potassium carbonate, 50ml of toluene, 30ml of ethanol and 30ml of water were mixed, and the Next, add tetrakis(triphenylphosphine) palladium 0.23g (0.0002mol) to react, raise the temperature to reflux, point the plate to monitor until the reaction is complete, end the reaction, spin the reaction solution to dryness, add 100ml of dichloromethane, make it dissolve completely and Pass through a silica gel column, add 100ml of water to the filtrate, wash with water to separate the organic phase, spin it to dryness, boil it...

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Abstract

The invention relates to a phenanthroimidazole symmetric derivative host material. The structure of the host material is represented by formula I, and can be used to form an organic electroluminescent device with the advantages of high luminescence efficiency, low driving voltage, long life, high brightness and high color purity. In the formula I, R1 and R2 are respectively independently selected from the hydrogen atom, substituted or unsubstituted C1-C30 alkyl groups, C1-C30 cycloalkyl groups, C1-C30 saturated alkyl groups, substituted or unsubstituted C1-C30 alkyloxy groups, substituted or unsubstituted C6-C30 aryl groups, substituted or unsubstituted C6-C30 aryloxy groups, substituted or unsubstituted C6-C30 arylamino groups, substituted or unsubstituted C2-C30 heterocyclic groups, substituted or unsubstituted C6-C30 fused polycyclic groups, hydroxy groups, cyan groups or substituted or unsubstituted amino groups.

Description

technical field [0001] The invention relates to an organic compound, in particular to a host material of a phenanthroimidazole symmetrical derivative and an electroluminescence device. Background technique [0002] Organic electroluminescence technology, or organic light-emitting diode technology, is seen as the next generation display technology. Compared with traditional liquid crystal (Liquid Crystal Display, LCD) technology, there is no need for backlight illumination and color filters, and pixels can emit light by themselves and appear on a color display panel. Moreover, it has the characteristics of ultra-high contrast, ultra-wide viewing angle, curved surface, and thin profile. [0003] Organic electroluminescent devices can be traced back to 1963 when Pope et al. studied blue electroluminescence with anthracene as a single crystal (10-20 μm). Because of the thick anthracene single crystal light-emitting layer and the constraints of the electrode materials used, the ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D235/02C07D235/18C07D403/14C07D409/14C07D405/14H01L51/54
CPCC07D235/02C07D235/18C07D403/14C07D405/14C07D409/14H10K85/624H10K85/626H10K85/6574H10K85/6572
Inventor 钱超许军王德宁
Owner NANJING TOPTO MATERIALS CO LTD
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