Dithiophene compound as well as preparation method and application thereof

A compound, dithiophene technology, applied in the field of dithiophene compound and its preparation and application, can solve the problems of poor electrical properties, difficult synthesis, poor stability, etc.

Active Publication Date: 2019-06-04
NINGBO LUMILAN NEW MATERIAL CO LTD +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] Therefore, the technical problem to be solved in the present invention is to overcome the technical defects of poor electrical properties, poor stability an

Method used

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  • Dithiophene compound as well as preparation method and application thereof
  • Dithiophene compound as well as preparation method and application thereof
  • Dithiophene compound as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0066] This embodiment provides a dithiophene compound intermediate compound, which has the structure shown in the following formula P01:

[0067]

[0068] The synthetic route of the intermediate compound of dithiophene compound shown in formula P01 is as follows:

[0069]

[0070] The preparation method of the dithiophene compound intermediate compound shown in formula P01 specifically comprises the following steps:

[0071] Take a 500ml double-neck round bottom bottle and put it into a stirring bar, fill it with nitrogen after drying; first add 14.022g of thieno

[0072] [3,2-b]thiophene (0.1mol, 1eq) and 36.488g N-bromosuccinimide (0.205mol, 2.05eq), followed by

[0073] Add 250mL of N,N-dimethylformamide and continue the reaction for 3 hours; stop the reaction with 200mL of saturated aqueous sodium bicarbonate solution, then extract with 200mL of diethyl ether, and repeat the extraction for 3 times, and the obtained extracts are sequentially added to magnesium sulfa...

Embodiment 2

[0077] This embodiment provides a dithiophene compound intermediate compound, which has the structure shown in the following formula P02:

[0078]

[0079] The synthetic route of the intermediate compound of the dithiophene compound shown in formula PO1 is as follows:

[0080]

[0081] The preparation method of the dithiophene compound intermediate compound shown in formula P02 specifically comprises the following steps:

[0082] (1) Synthetic intermediate C01

[0083] Take a 500 ml three-neck round bottom bottle and put it into a stirring bar and an upper addition funnel, fill it with nitrogen after drying; Dissolve 23.841g of compound P01 (0.08mol, 1eq) in 150mL of anhydrous tetrahydrofuran, and add the resulting solution dropwise into a three-neck round bottom flask at -78°C, and continue the reaction for 18 hours after the reaction gradually returns to temperature; Saturated aqueous sodium bicarbonate solution was used to stop the reaction, followed by extraction w...

Embodiment 3

[0089] This embodiment provides a dithiophene compound intermediate compound, which has the structure shown in the following formula P03:

[0090]

[0091] The synthetic route of the intermediate compound of dithiophene compound shown in formula P03 is as follows:

[0092]

[0093] The difference between the preparation method of the dithiophene compound intermediate compound shown in the formula P03 and the preparation step of the intermediate compound of the dithiophene compound shown in P01 provided in Example 1 is only:

[0094] Replace thieno[3,2-b]thiophene in Example 1 with 19.028g 4,8-dichloro-benzo[1,2-b:4,5-b']dithiophene (0.082mol, 1eq), And adjust other reactants to be identical with the molar equivalent in embodiment 1, obtain 37.942g compound P03 (productive rate: 91%)

[0095] Elemental analysis: (C 10 h 2 Br 2 Cl 2 S 2 ) Theoretical value: C, 28.81; H, 0.48; Br, 38.33; Cl, ​​17.00; S, 15.38; found value: C, 28.85;

[0096] HRMS (EI) m / z (M+): theor...

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Abstract

The invention belongs to the technical field of display, and particularly relates to a dithiophene compound as well as a preparation method and an application thereof. The dithiophene compound has a structure as shown in formula I) or formula II), dithiophene is used as a mother nucleus, the conjugated performance is good, an electron withdrawing group increasing the modification property of the mother nucleus is introduced, the LUMO energy level of the dithiophene compound is reduced, the thermal stability of the dithiophene compound is improved, and the solubility is improved; the preparation method is simple, the yield is high, the cost is reduced, the dithiophene compound can be applied to a n-type doping material, promotes the hole generation and carrier combination, can be applied toa hole transport material, promotes hole generation, improves the hole transport speed, and can be applied to an organic electroluminescent device to reduce driving voltage and keep use stability andthe luminous efficiency of the device, and a produced product is good in luminescence property and long in service life and has a good application prospect.

Description

technical field [0001] The invention belongs to the field of display technology, and in particular relates to a dithiophene compound and its preparation and application. Background technique [0002] In 1987, Dr. Deng Qingyun and others from the laboratory of Eastman Kodak in the United States made the first organic electroluminescence (OEL) device (hereinafter referred to as OEL device) (Appl .Phys.Lett., 1987,51,913), they use transparent and conductive indium tin oxide (ITO) as the cathode, and sequentially vapor-deposit diamine derivatives and tris(8-hydroxyquinoline) aluminum on it, Magnesium-silver alloy is used as the anode material. This multilayer structure can reduce the driving voltage of the OEL device and effectively improve the charge injection problem between the material molecule and the electrode interface, thereby improving device performance and life. [0003] Compared with traditional technologies, OEL devices have many advantages such as low turn-on vol...

Claims

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Application Information

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IPC IPC(8): C07D495/04C07D495/14H01L51/50H01L51/54
Inventor 魏定纬谢坤山丁欢达陈志宽
Owner NINGBO LUMILAN NEW MATERIAL CO LTD
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