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Tri-hypo-phenanthrene nitrogen-containing seven-membered ring compound, preparation method therefor and application of tri-hypo-phenanthrene nitrogen-containing seven-membered ring compound

A compound and seven-membered ring technology, which is applied in the field of Sanya phenanthrene nitrogen-containing seven-membered ring compound and its preparation, can solve problems affecting performance and difficulty in forming a uniform film, and achieve high glass transition temperature, easy access, and reaction The effect of regulation

Active Publication Date: 2020-01-24
NINGBO LUMILAN NEW MATERIAL CO LTD +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] Therefore, the technical problem to be solved by the present invention is to overcome the defects that it is difficult to form a uniform thin film of the red light-emitting organic material in the prior art, which further affects various performances, so as to provide a film that can be formed uniformly and has good thermal stability. Sanya phenanthrene nitrogen-containing seven-membered ring compound with high luminous efficiency and its preparation method and use

Method used

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  • Tri-hypo-phenanthrene nitrogen-containing seven-membered ring compound, preparation method therefor and application of tri-hypo-phenanthrene nitrogen-containing seven-membered ring compound
  • Tri-hypo-phenanthrene nitrogen-containing seven-membered ring compound, preparation method therefor and application of tri-hypo-phenanthrene nitrogen-containing seven-membered ring compound
  • Tri-hypo-phenanthrene nitrogen-containing seven-membered ring compound, preparation method therefor and application of tri-hypo-phenanthrene nitrogen-containing seven-membered ring compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0044] This embodiment provides a nitrogen-containing seven-membered ring compound of Sanyaphenanthrene, which has the structure shown in the following formula F-1:

[0045]

[0046] The synthetic route of compound shown in formula F-1 is as follows:

[0047]

[0048] The preparation method of the compound shown in formula F-1 specifically comprises the following steps:

[0049] (1) Preparation of intermediate (C-1)

[0050] Under nitrogen protection, in a 500ml four-necked flask, compound (A) 22.9g (84mmol), compound (B-1) 14.1g (70mmol), Pd (PPh 3 ) 4 4g, (34.6mmol), Na 2 CO 3 22.3g (210mmol) was dissolved in a mixture of 200mL of toluene, 50mL of EtOH, and 50mL of distilled water, refluxed and stirred at 120°C for 6 hours, then quenched the reaction with water, separated the water phase, removed most of the solvent by rotary evaporation, precipitated solid and dried to obtain the intermediate Compound (C-1) 24.1g (98% yield);

[0051] (2) Preparation of Intermed...

Embodiment 2

[0057] This embodiment provides a nitrogen-containing seven-membered ring compound of Sanyaphenanthrene, which has the structure shown in the following formula F-2:

[0058]

[0059] The synthetic route of compound shown in formula F-2 is as follows:

[0060]

[0061] The preparation method of the compound shown in formula F-2 specifically comprises the following steps:

[0062] (1) Preparation of intermediate (C-1)

[0063] The preparation of intermediate (C-1) is the same as in Example 1;

[0064] (2) Preparation of Intermediate (D-1)

[0065] The preparation of intermediate (D-1) is the same as in Example 1;

[0066] (3) Preparation of compound (F-2)

[0067] Under nitrogen protection, in a 500ml four-necked flask, add 19g (60mmol) compound (D-1) at room temperature, 17.7g (65mmol) compound (E-2), 200ml of toluene, 11.5g (120mmol) sodium tert-butoxide , 182 mg (0.2 mmol) Pd 2 (dba) 3 , 1.2ml (0.6mmol) 10% tri-tert-butylphosphine toluene solution, after reflux r...

Embodiment 3

[0070] This embodiment provides a nitrogen-containing seven-membered ring compound of Sanyaphenanthrene, which has the structure shown in the following formula F-3:

[0071]

[0072] The synthetic route of compound shown in formula F-3 is as follows:

[0073]

[0074] The preparation method of the compound shown in formula F-3 specifically comprises the following steps:

[0075] (1) Preparation of intermediate (C-1)

[0076] The preparation of intermediate (C-1) is the same as in Example 1;

[0077] (2) Preparation of Intermediate (D-1)

[0078] The preparation of intermediate (D-1) is the same as in Example 1;

[0079] (3) Preparation of Compound (F-3)

[0080] Under nitrogen protection, in a 500ml four-necked flask, add 19g (60mmol) compound (D-1) at room temperature, 21g (65mmol) compound (E-3), 200ml of toluene, 11.5g (120mmol) sodium tert-butoxide, 182mg (0.2mmol) Pd 2 (dba) 3 , 1.2ml (0.6mmol) 10% tri-tert-butylphosphine toluene solution, after reflux reacti...

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Abstract

The invention belongs to the technical field of organic electroluminescent materials and particularly relates to a tri-hypo-phenanthrene nitrogen-containing seven-membered ring compound, a preparationmethod therefor and an application of the tri-hypo-phenanthrene nitrogen-containing seven-membered ring compound. The compound has a structure represented by a formula (F) shown in the description. According to the compound, a nitrogen-containing seven-membered ring serves as a center, a large PI-PI conjugated system is relatively difficult to form, and thus, electron migration and charge transfer of a whole system trend to gain certain balance; and the compound is relatively high in glass transition temperature and easy to form a uniform film, so that the material is good in thermal stability and high in luminescence efficiency.

Description

technical field [0001] The invention belongs to the technical field of organic electroluminescent materials, and in particular relates to a nitrogen-containing seven-membered ring compound of Sanyaphenanthrene and its preparation method and application. Background technique [0002] Organic light-emitting diodes (OLEDs) based on small molecules or polymers have attracted much attention due to their potential applications in full-color, flat-panel displays, and lighting since the pioneering work of Tang et al. Diodes (OLEDs), as a brand-new display technology, have unparalleled advantages in various performances of existing display technologies, such as all-solid-state, self-luminous, high brightness, high resolution, wide viewing angle (above 170 degrees), Fast response, thin thickness, small size, light weight, flexible substrate, low-voltage DC drive (3-10V), low power consumption, wide operating temperature range, etc., make it widely used in the market, such as lighting ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D223/14C07D403/04C07D405/04C09K11/06H01L51/50H01L51/54
CPCC07D223/14C07D405/04C07D403/04C09K11/06C09K2211/1029C09K2211/1044C09K2211/1088H10K85/615H10K85/631H10K85/6572H10K85/6574H10K50/11
Inventor 张玉祥唐省兵丁欢达陈志宽
Owner NINGBO LUMILAN NEW MATERIAL CO LTD
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