Compound taking olefinic bond-containing seven-membered ring as core, and application of compound

A compound and a seven-membered ring technology, applied in the application field of organic electroluminescent devices, can solve problems such as performance differences

Pending Publication Date: 2020-07-03
JIANGSU SUNERA TECH CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In addition, for the collocation of OLED devices with different structures, the photoelectric functional materials used have strong selectivity, and the performance of the same material in devices with different structures may be completely different.

Method used

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  • Compound taking olefinic bond-containing seven-membered ring as core, and application of compound
  • Compound taking olefinic bond-containing seven-membered ring as core, and application of compound
  • Compound taking olefinic bond-containing seven-membered ring as core, and application of compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0061] Embodiment 1: the preparation of intermediate M:

[0062]

[0063] Starting material B-1 (0.5 mmol) was dissolved in tetrahydrofuran (1.5 ml) and the solution was cooled to -78°C (dry ice / acetone). The mixture was then treated with a small amount of trimethylsilyldiazomethane (2M, 0.25ml, 0.5mmol) in ether until the intense color of starting material B-1 disappeared; the mixture was allowed to warm slowly to -45°C until N 2 of elimination. Then, raw material A-1 (0.5 mmol) was added using an ice bath (0° C.) for 10 minutes, and a mixture solution of tetrabutylammonium fluoride (1M solution in tetrahydrofuran, 1 ml, 1 mmol) was added to the solution. After removal of the solvent under vacuum, the crude product was purified by column chromatography to afford intermediate M-1. Elemental analysis structure (molecular formula C 28 h 17 Br): Theoretical C, 77.61; H, 3.95; Br, 18.44; Found: C, 77.62; H, 3.95; Br, 18.43. ESI-MS (m / z) (M+): The theoretical value is 432.0...

Embodiment 2

[0068] Embodiment 2: the synthesis of compound 3:

[0069]

[0070] Dissolve 0.01 mol of intermediate M-1 and 0.012 mol of raw material C-1 in 150 mL of toluene and ethanol (V toluene: V ethanol = 5: 1) mixed solution, add 0.0002 mol of Pd(PPh 3 ) 4 and 0.02mol K 2 CO 3 , reacted at 110°C for 24 hours under an atmosphere of nitrogen gas, took a sample and spotted the plate, after the raw materials were completely reacted, cooled and filtered, the filtrate was rotary evaporated to remove the solvent, and the crude product was passed through a silica gel column to obtain compound 3; the elemental analysis structure ( Molecular formula C 51 h 30 N 2 O): theoretical value C, 89.19; H, 4.40; N, 4.08; found value: C, 89.19; H, 4.40; N, 4.07. ESI-MS (m / z) (M+): theoretical value 686.24, found value 686.54.

Embodiment 3

[0071] Embodiment 3: the synthesis of compound 12:

[0072]

[0073] The preparation method of compound 12 is the same as Example 2, and the difference is that intermediate M-1 is replaced with intermediate M-2, and raw material C-1 is replaced with raw material C-2; Elemental analysis structure (molecular formula C 51 h 30 N 2 O): theoretical value C, 89.19; H, 4.40; N, 4.08; found value: C, 89.19; H, 4.40; N, 4.07. ESI-MS (m / z) (M+): The theoretical value is 686.24, and the measured value is 686.79.

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Abstract

The invention discloses a compound taking an olefinic bond-containing seven-membered ring as a core, and application of the compound, wherein the structure of the compound is represented by a generalformula (1). The compound provided by the invention has high glass transition temperature and molecular thermal stability, proper HOMO and LUMO energy levels and high Eg, and by optimizing the devicestructure, the photoelectric property of an OLED device can be effectively improved, and the service life of the OLED device can be effectively prolonged.

Description

technical field [0001] The invention relates to the technical field of semiconductor materials, in particular to a compound with an ethylenic bond-containing seven-membered ring as the core, a preparation method thereof and an application in an organic electroluminescent device. Background technique [0002] Organic electroluminescent (OLED: Organic Light Emission Diodes) device technology can be used to manufacture new display products and also can be used to make new lighting products, which is expected to replace the existing liquid crystal display and fluorescent lighting, and has a wide application prospect. The OLED light-emitting device is like a sandwich structure, including electrode material film layers and organic functional materials sandwiched between different electrode film layers. Various functional materials are superimposed on each other according to the application to form an OLED light-emitting device. OLED light-emitting devices are current devices. When...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D471/04C07D491/048C07D491/056C07D491/147C07D519/00C09K11/06H01L51/54
CPCC07D491/147C07D471/04C07D491/056C07D491/048C07D519/00C09K11/06C09K2211/1011C09K2211/1029C09K2211/1033C09K2211/1088H10K85/626H10K85/615H10K85/657H10K85/6572
Inventor 李崇张兆超陈海峰王芳
Owner JIANGSU SUNERA TECH CO LTD
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