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Compound and preparation method and application thereof

A compound and unsubstituted technology, applied in the field of compound and its preparation, can solve the problems of further improvement of current efficiency and high turn-on voltage, and achieve the effect of improving luminous efficiency and luminous performance, high glass transition temperature, and balanced injection and transmission

Inactive Publication Date: 2019-11-22
NINGBO LUMILAN NEW MATERIAL CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, its turn-on voltage is relatively high, and the current efficiency needs to be further improved.

Method used

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  • Compound and preparation method and application thereof
  • Compound and preparation method and application thereof
  • Compound and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Synthetic example 1

[0100] This synthetic example provides a kind of synthetic method of compound, specifically as follows:

[0101]

[0102](1) Intermediate 1-1 synthesis steps: take 1000 milliliters of double-neck round bottom flasks and put them into a stirring bar and an upper connection reflux tube, fill with nitrogen after drying; first add compound 1-bromo-2-nitrobenzene ( 24.24 g, 1.2 eq), dibenzofuran-3-boronic acid (21.20 g, 1.0 eq), potassium carbonate (1.5 eq), ethanol (100 ml), water (100 ml), toluene (400 ml), tetra( Triphenylphosphine) palladium (0.5 equivalents), then heated to reflux and reacted for 12 hours, and cooled to room temperature after the reaction was completed. It was quenched by adding 200 mL of water and extracted with dichloromethane (3 x 400 mL). The resulting extract was dried by adding magnesium sulfate, filtered and spin-dried; the crude product was purified by chromatography (ethyl acetate / hexane, 1 / 10) to obtain intermediate 1-1 (20.23 g, yield 70% ).

...

Synthetic example 2

[0109] This synthetic example provides a kind of synthetic method of compound, specifically as follows:

[0110]

[0111] (1) Synthesis of intermediate 1-1: same as the synthesis of intermediate 1-1 in Synthesis Example 1;

[0112] (2) Synthesis of intermediate 2-1: same as the synthesis of intermediate 2-1 in Synthesis Example 1;

[0113] (3) Synthesis of intermediate 3-1: same as the synthesis of intermediate 3-1 in Synthesis Example 1;

[0114] (4) Synthesis of intermediate 4-2: take 500 milliliters of double-necked round-bottomed bottles and put them into a stirring bar and an upper connection reflux tube, fill with nitrogen after drying, and add intermediate 3-2 (41.51 grams, 1.0 eq. ), 2-boronic acid-4-phenylquinazoline (50.01 g, 2.0 equivalents), potassium carbonate (1.5 equivalents), ethanol (25 milliliters), water (25 milliliters), toluene (100 milliliters), tetrakis(triphenyl phosphine) palladium (0.5 equiv), and the mixture was refluxed for 12 hours. Cool to r...

Synthetic example 3

[0118] This synthetic example provides a kind of synthetic method of compound, specifically as follows:

[0119]

[0120] (1) Synthesis of intermediate 1-1: Synthesis with 1-1 in Synthesis Example 1;

[0121] (2) Synthesis of intermediate 2-1: Synthesis with 2-1 in Synthesis Example 1;

[0122] (3) Synthesis of intermediate 3-1: Synthesis with 3-1 in Synthesis Example 1;

[0123] (4) Synthesis of intermediate 4-3: take 500 milliliters of double-necked round-bottomed bottles and put them into a stirring bar and an upper connection reflux tube, fill with nitrogen after drying, and first add intermediate 3-1 (41.51 grams, 1.0 equivalent ), 3-(4-boronic acid phenyl)-dibenzofuran (57.6 g, 2.0 eq), potassium carbonate (1.5 eq), ethanol (25 ml), water (25 ml), toluene (100 ml), tetra (Triphenylphosphine)palladium (0.5 equiv), and the mixture was refluxed for 12 hours. Cool to room temperature after reaction. The reaction system was added with water, extracted with dichlorometh...

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Abstract

The invention relates to a compound and a preparation method and application thereof. The compound has any one of structures as shown in formulas (I) to (V), the HOMO energy level and LUMO energy level of the compound are respectively matched with a hole transport layer and an electron transport layer. Meanwhile, due to the specific three-dimensional configuration, molecular stacking of material molecules is avoided, annihilation caused by existence of high-energy excitons is reduced, the energy transfer efficiency is improved, the luminous efficiency is improved, the driving voltage is reduced, the glass-transition temperature of the compound is high, the film-forming property is good, and the device has high stability.

Description

technical field [0001] The invention relates to the technical field of organic electroluminescence, in particular to a compound and its preparation method 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 light-emitting diode (OLED) device (hereinafter referred to as OLED device) by vacuum evaporation for the first time. (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 three (8-hydroxyquinoline) on it ) aluminum, and magnesium-silver alloy is used as the anode material. This multilayer structure can reduce the driving voltage of the OLED device, and effectively improve the charge injection problem between the material molecule and the electrode interface, thereby improving the device performance and life. [0003] Compared with traditional technolog...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D491/048C07D495/04C07D491/22C07D493/04C07D487/04C09K11/06H01L51/30H01L51/46H01L51/54
CPCC07D491/048C07D495/04C07D491/22C07D493/04C07D487/04C09K11/06C09K2211/1044C09K2211/1011C09K2211/1088C09K2211/1092C09K2211/1074C09K2211/1007H10K85/615H10K85/654H10K85/657H10K85/6572H10K85/6576H10K85/6574
Inventor 李祥智蔡烨丁欢达魏定纬陈志宽
Owner NINGBO LUMILAN NEW MATERIAL CO LTD
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