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Phosphine-containing fused heterocyclic compound as well as preparation method and application thereof

A technology of fused heterocycles and compounds, which is applied in the field of phosphine-containing fused heterocycles and its preparation, can solve the problems of less electron transport materials and less research accumulation of OLED devices, so as to improve electron transport capabilities, inhibit molecular stacking, and reduce drive The effect of voltage

Active 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

[0006] However, the current research on OLED devices is less accumulated, and the available electron transport materials are less, and new electron transport materials still need to be developed urgently.

Method used

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  • Phosphine-containing fused heterocyclic compound as well as preparation method and application thereof
  • Phosphine-containing fused heterocyclic compound as well as preparation method and application thereof
  • Phosphine-containing fused heterocyclic compound as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

preparation example 1

[0075] The synthesis of compound 1-1, its synthetic route is as follows:

[0076]

[0077] Concrete synthetic steps are as follows:

[0078] (1) Synthesis of intermediate 1-(1-1): under a nitrogen atmosphere, 1,4-dibromo-2,3-diiodo-5,6-dimethoxyl ( 54.77 grams, 0.1mol, 1 equivalent), o-bromophenylboronic acid (60.00 grams, 0.3mol, 3 equivalents), tetrakis (triphenylphosphine) palladium (5.8 grams, 0.005mol), potassium phosphate (55.16 grams, 0.4mol, 4 equivalents), THF (150 ml), water (40 ml), the reactants were heated to 80 degrees Celsius and stirred for 20 hours. After the reaction was completed, the solvent was spin-dried, and the crude product was purified by chromatography (ethyl acetate / hexane=1 / 15) to obtain intermediate 1-(1-1) (32.71 g, yield 54%).

[0079] (2) Synthesis of intermediate 2-(1-1): under a nitrogen atmosphere, add intermediate 1-(1-1) (30.29 grams, 0.05mol, 1 equivalent), tetrahydrofuran (100 milliliters), slowly add n-butyllithium (12.82 grams, 0...

preparation example 2

[0086] The synthesis of compound 2-1 and compound 2-2, its synthetic route is as follows:

[0087]

[0088] Concrete synthetic steps are as follows:

[0089] (1) Synthesis of intermediate 1-(2-1): under a nitrogen atmosphere, 1,4-dibromo-3,6-diiodo-2,5-dimethoxyl ( 54.77 grams, 0.1mol, 1 equivalent), o-bromophenylboronic acid (60.00 grams, 0.3mol, 3 equivalents), tetrakis (triphenylphosphine) palladium (5.8 grams, 0.005mol, 0.05 equivalents), potassium phosphate (55.16 grams, 0.4mol, 4 equivalents), THF (150ml), water (40ml), the reactants were heated to 80°C and stirred for 20 hours. After the reaction was completed, the solvent was spin-dried, and the crude product was purified by chromatography (ethyl acetate / hexane=1 / 15) to obtain intermediate 1-(2-1) (32.71 g, yield 54%).

[0090] (2) Synthesis of intermediate 2-(2-1): under a nitrogen atmosphere, add intermediate 1-(2-1) (30.29 grams, 0.05mol, 1 equivalent), tetrahydrofuran (100 milliliters), slowly add n-butyllith...

preparation example 3

[0098] The synthesis of compound 3-1, its synthetic route is as follows:

[0099]

[0100] Concrete synthetic steps are as follows:

[0101] (1) Synthesis of intermediate 1-(3-1): under a nitrogen atmosphere, 1,3-dibromo-4,6-diiodo-2,5-dimethoxyl ( 54.77 g, 0.1 mol, 1 eq), 2-bromo-5-methylphenylboronic acid (64.20 g, 0.3 mol, 3 eq), tetrakis(triphenylphosphine) palladium (5.8 g, 0.005 mol, 0.05 eq), Potassium phosphate (55.16 g, 0.4 mol, 4 equivalents), THF (150 ml), water (40 ml), and the reactants were heated to 80°C and stirred for 20 hours. After the reaction was completed, the solvent was spin-dried, and the crude product was purified by chromatography (ethyl acetate / hexane=1 / 15) to obtain intermediate 1-(3-1) (36.76 g, yield 58%).

[0102] (2) Synthesis of intermediate 2-(3-1): under nitrogen atmosphere, add intermediate 1-(3-1) (31.69 grams, 0.05mol, 1 equivalent), tetrahydrofuran (100 milliliters), slowly add n-butyllithium (12.82 grams, 0.2mol, 4 equivalents) in...

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Abstract

The invention provides a phosphine-containing fused heterocyclic compound as well as a preparation method and an application thereof. The phosphine-containing fused heterocyclic compound has a structure as shown in a formula I, a formula II, a formula III, a formula IV or a formula V. The phosphine-containing fused heterocyclic compound provided by the invention has double phosphorus-oxygen bonds,and an electron-withdrawing or large-volume Ar3 group and an Ar4 group are introduced; therefore, the material has a low LUMO energy level, a high electron transport capability and a high thermal decomposition temperature, can be used as an electron transport material of a photoelectric device, reduces the driving voltage of the device, improves the current efficiency, maintains thermal stabilityin the preparation and use processes of the device, and prolongs the service life of the device.

Description

technical field [0001] The invention belongs to the technical field of organic photoelectric materials, and in particular relates to a phosphine-containing condensed heterocyclic compound and its preparation method and application. Background technique [0002] Organic light-emitting diode (OLED) is an organic electroluminescent device. Compared with inorganic electroluminescence, it has high brightness, fast response, wide viewing angle, simple process, high color purity, and can realize the range from blue light to red light. The advantages of full-color display and flexibility are favored by many scientists and have broad application prospects in the fields of display and lighting. [0003] The development of OLED has a history of more than 50 years. The earliest discovery of organic electroluminescence was in 1963. Pope et al. used hundreds of volts of voltage to add organic aromatic single crystal anthracene to observe the luminescence phenomenon. However, due to the l...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F9/6568H01L51/54H01L51/50
CPCC07F9/65685H10K85/6565H10K85/654H10K85/6574H10K85/657H10K85/6572H10K50/16
Inventor 魏定纬蔡烨谢坤山丁欢达陈志宽
Owner NINGBO LUMILAN NEW MATERIAL CO LTD
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