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A kind of axene compound and its preparation method and application

A compound and alkene technology, applied in the field of alkene compounds and their preparation, can solve the problems of short service life, difficult evaporation, small molecular weight, etc., and achieve the effects of improving service life, good thermal stability, and avoiding Joule heat

Active Publication Date: 2021-06-08
NINGBO LUMILAN NEW MATERIAL CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] For methods of improving hole transport (P-doping), the physical properties of the materials used present problems during sublimation purification or vacuum evaporation involving fluorinated tetracyanoquinodimethane (TCNQ or F4TCNQ), due to its small molecular weight, it is easy to diffuse into the equipment during the sublimation process, resulting in contamination of the equipment or devices, so that this type of dopant cannot be used in mass production devices, and the prepared devices have a short service life and are not suitable for commercial applications
[0004] CN103959392A discloses an improved doping method for hole injection and transport layers comprising reacting at least one first compound in neutral form with at least one ionic dopant in a first solvent system to providing a first doping reaction product; isolating the first doping reaction product in solid form; and combining the isolated first doping reaction product with a neutral form of at least one conjugated polymer in a second solvent system to Formation of a second doped reaction product comprising an oxidized form of the conjugated polymer and a neutral form of the first compound; this patent has a relatively short lifetime despite its lower metal content
CN102292839A discloses an OLED stability improved by a doped hole transport layer and an organic light-emitting device, the device comprises an anode and a cathode, a first organic layer is located between the anode and the cathode, the first organic layer comprises The light-emitting layer of the first organic light-emitting material, the device also includes a second organic layer located between the anode and the first organic layer, the second organic layer is a non-light-emitting layer, and the second organic layer contains % concentration of organic small molecule hole transport materials, and organic small molecule electron transport materials with a concentration of 0.1 to 5wt%, this patent makes OLED devices have high stability, but their luminous efficiency is low

Method used

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  • A kind of axene compound and its preparation method and application
  • A kind of axene compound and its preparation method and application
  • A kind of axene compound and its preparation method and application

Examples

Experimental program
Comparison scheme
Effect test

preparation example 1

[0075] A kind of alkene compound P1, preparation method is as follows:

[0076]

[0077] (1) Synthesis of P1-B: in a 25mL three-neck flask, under nitrogen protection, add P1-A (1.32g, 0.01mol), malondicyanide (0.66g, 0.01mol), potassium carbonate (2.07g, 0.015mol) ), ethanol (10 mL), stirred at room temperature for 8 h, after the reaction was completed, cooled to room temperature, quenched by adding 5 mL of water, extracted with ethyl acetate (20 mL × 3), dried over anhydrous sodium sulfate, spin-dried, the crude product was separated into layers Analytical purification (dichloromethane / n-hexane volume ratio, 1 / 5) gave P1-B (1.13 g, yield 63%).

[0078] (2) Synthesis of P1-C: in a 25mL three-necked flask, add P1-8 (3.6g, 0.02mol), nitric acid (6mL), react at room temperature for 1 hour, add water to quench, and adjust the pH to 7 with sodium carbonate, Dichloromethane was extracted, the organic layer was dried over anhydrous magnesium sulfate, and the crude product was pur...

preparation example 2

[0083] A kind of alkene compound P2, preparation method is as follows:

[0084]

[0085] P2 was prepared with reference to the preparation method of Preparation Example 1, except that the diaminomaleonitrile in step (3) was replaced by cis-1,2-difluoroethylene-1,2-diamine (0.94 g, 0.01 mol) to give P2 (2.95 g, 40% yield).

[0086] Elemental Analysis: C 30 N 12 F 6 S 3 Theoretical value: C, 48.79; N, 22.76; Measured value: C, 48.84; N, 22.72; HRMS (ESI) m / z (M + ): theoretical value: 737.9435; measured value: 737.9428.

preparation example 3

[0088] A kind of alkene compound P5, preparation method is as follows:

[0089]

[0090] P5 was prepared with reference to the preparation method of Preparation Example 1, except that malononitrile in step (1) was replaced with 1,1,1,3,3,3-hexafluoropropane (1.52g, 0.01mol), and step ( The diaminomaleonitrile in 3) was replaced with cis-1,2-difluoroethylene-1,2-diamine (0.94 g, 0.01 mol) to give P5 (3.78 g, 38% yield).

[0091] Elemental Analysis: C 30 N 6 F 24 S 3 Theoretical value: C, 36.16; N, 8.43; Measured value: C, 36.12; N, 8.40; HRMS (ESI) m / z (M + ): theoretical value: 995.8963; measured value: 995.8957.

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Abstract

The present invention provides an axene compound, its preparation method and application, including the compound with the structure shown in formula I. The axene compound provided by the present invention has a non-planar structure (three-dimensional structure), and there is no stacking between molecules, which can reduce the annihilation generated by high-energy excitons, promote the anode to inject holes into the hole transport layer, avoid the generation of Joule heat, avoid The stacking and crystallization of the molecules in the hole transport layer can further improve the service life of the device; the axenene compound provided by the invention has good thermal stability and good film-forming property, which is also beneficial to improving the service life of the device.

Description

technical field [0001] The invention belongs to the field of organic electroluminescence, and relates to an axene compound, a preparation method and application thereof. Background technique [0002] In recent years, some optoelectronic materials used in OLED devices have become increasingly known. It is well known that aromatic diamine derivatives are used as hole transport materials in OLED devices. When using this type of material, it is necessary to increase the applied voltage of the device to obtain sufficient luminous brightness. , which shortens the life of the device and increases power consumption. To solve these problems, hole injection and hole transport in OLED devices can be significantly improved by doping electron acceptor compounds (document: He Gufeng, Appl. Phys.lett. 85 (2004) 3911-3913). Under the same luminous efficiency, the addition of its electron acceptor compound can greatly reduce the working voltage of OLED devices; strong electron acceptor comp...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D519/00C07D307/87C07D333/72C09K11/06H01L51/54
CPCC07D519/00C07D307/87C07D333/72C09K11/06C09K2211/1051C09K2211/1092C09K2211/1048C09K2211/1059C09K2211/1088H10K85/653H10K85/655H10K85/654H10K85/657
Inventor 魏定纬蔡烨丁欢达陈志宽
Owner NINGBO LUMILAN NEW MATERIAL CO LTD
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