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A kind of phosphine heterocyclic compound, synthesis method and application thereof

A compound and ring technology, applied in the field of organic electroluminescent materials, can solve the problems of low efficiency of OLED devices, unbalanced carrier transport, low thermal stability, etc., achieve good thermal stability, improve efficiency, and reduce LUMO track effect

Active Publication Date: 2020-04-07
郑州金上化成新材料有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, there are still some problems in the organic materials currently used in organic electroluminescent devices: low thermal stability, low electron injection and transport capabilities resulting in unbalanced carrier transport, and aggregation fluorescence quenching effects that make the solid-state thin film These are the bottlenecks that restrict the development of organic electroluminescent devices, resulting in low efficiency and short service life of OLED devices, which seriously restrict their wider application, especially large-screen displays. Therefore, for organic electroluminescent devices The wider application of luminescent materials requires the development of stable and efficient new materials

Method used

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  • A kind of phosphine heterocyclic compound, synthesis method and application thereof
  • A kind of phosphine heterocyclic compound, synthesis method and application thereof
  • A kind of phosphine heterocyclic compound, synthesis method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0024] The synthesis of embodiment 1 compound Ia

[0025]

[0026] Synthesis of compound Ⅱ

[0027] Under argon protection, 1-pyreneboronic acid (24.6g), o-bromoiodobenzene (28.2g), toluene (300mL), water (30mL), and tetrakis(triphenylphosphine) palladium (200mg) were successively added to the flask. , Potassium carbonate (27.6g), heated to reflux for 10h. Stop the reaction, extract three times with ethyl acetate, combine the organic phases, and wash with water until neutral; separate the organic phases, add anhydrous magnesium sulfate to dry, filter with suction, and spin dry; silica gel column chromatography yields 30.3 g of compound II as a white solid, Yield 85%.

[0028] Synthesis of compound Ⅲ

[0029] Under the protection of argon, compound II (20g) and tetrahydrofuran (200mL) were added to the flask, then the system was cooled to -78°C, and a 2.5M n-hexane solution (25mL) containing n-butyllithium was added dropwise to the system , after the dropwise addition, r...

Embodiment 2

[0033] ESI, m / z: [M+H] + calcd for C 28 h 18 OP, theoretical value: 401.1095; measured value: 401.1093. The synthesis of embodiment 2 compound 1b

[0034]

[0035] Compound III (5.0 g), toluene (100 mL) and palladium acetate (120 mg) obtained according to the synthesis method of Example 1 were added into the flask, and the reaction was heated under reflux for 10 hours. After returning to room temperature, excess sulfur powder was added to the system, reacted for 5 hours, and spin-dried; silica gel column chromatography yielded 3.4 g of a light yellow solid, with a yield of 76%.

[0036] 31 PNMR (162Hz, CDCl 3 ), δ: 34; 1 HNMR (400MHz, CDCl 3 ), δ:6.71~6.89(m,5H),7.04~7.72(m,10H),7.83~8.05(m,2H);

[0037] ESI, m / z: [M+H] + calcd for C 28 h 18 PS, theoretical value: 417.0867; measured value: 417.0864. The synthesis of embodiment 3 compound Ic

Embodiment 3

[0037] ESI, m / z: [M+H] + calcd for C 28 h 18 PS, theoretical value: 417.0867; measured value: 417.0864. The synthesis of embodiment 3 compound Ic

[0038]

[0039] Compound III (5.0 g), toluene (100 mL) and palladium acetate (120 mg) obtained according to the synthesis method of Example 1 were added into the flask, and the reaction was heated under reflux for 10 hours. After returning to room temperature, excess selenium powder was added to the system, reacted for 5 hours, and spin-dried; silica gel column chromatography gave 3.8 g of a light yellow solid, with a yield of 75%.

[0040] 31 PNMR (162Hz, CDCl 3 ), δ: 37; 1 HNMR (400MHz, CDCl 3 ), δ:6.70~6.89(m,5H),7.03~7.74(m,10H),7.81~8.03(m,2H);

[0041] ESI, m / z: [M+H] + calcd for C 28 h 18 SeP, theoretical: 465.0311; found: 465.0310.

[0042] The following is the application of the compounds of the present invention

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Abstract

The invention discloses a phosphine heterocyclic compound, a synthesis method and an application thereof, belonging to the field of organic electroluminescent materials. This type of compound has the general structural formula shown in Formula I, wherein X is O, S or Se. The organic electroluminescent compound of the present invention can be applied to the light-emitting layer of an organic electroluminescent device, and the light-emitting performance of the corresponding device can be regulated by simple chemical modification of the phosphine atom; this type of compound has good thermal stability, and the existence of the phosphine heterocyclic structure effectively reduces the The intermolecular stacking effect can be eliminated, which can significantly improve the efficiency and lifetime of the corresponding organic electroluminescent devices. I.

Description

technical field [0001] The invention relates to the field of organic electroluminescent materials, in particular to a phosphine heterocyclic organic electroluminescent compound, a synthesis method and an application thereof. Background technique [0002] As a new type of display technology, organic electroluminescent devices have self-illumination, wide viewing angles, low energy consumption, high efficiency, thinness, rich colors, fast response speed, wide applicable temperature range, low driving voltage, flexible, bendable and The unique advantages of transparent display panels and environmental friendliness can be applied to flat panel displays and new generation lighting, and can also be used as LCD backlight. Since their invention in the late 1980s, organic electroluminescent devices have found industrial applications, such as screens for cameras and mobile phones. However, there are still some problems in the organic materials currently used in organic electrolumines...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07F9/6568C09K11/06H01L51/50H01L51/54
CPCC09K11/06C07F9/65685C09K2211/1096C09K2211/1007H10K85/657H10K50/00
Inventor 陈辉孙敏青屈凤波张银龙杨振强杨瑞娜段征席振峰
Owner 郑州金上化成新材料有限公司
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