Heteroanthracene derivative and organic light-emitting device thereof

A technology of organic light-emitting devices and derivatives, which is applied in the fields of light-emitting materials, organic chemistry, and electric solid-state devices, and can solve problems such as low efficiency and short device life

Inactive Publication Date: 2018-01-19
CHANGCHUN HYPERIONS TECH CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, some OLEDs have technical problems such as short device life and low efficiency. Therefore, it is urgent to solve technical problems such as short device life and low efficiency.

Method used

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  • Heteroanthracene derivative and organic light-emitting device thereof
  • Heteroanthracene derivative and organic light-emitting device thereof
  • Heteroanthracene derivative and organic light-emitting device thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0043] Embodiment 1: the preparation of compound 1

[0044]

[0045] To phenoxazine (3.38 g, 18.3 mmol) and 3,8 dibromo-1,6 isopropyl-1,9-dihydropyrene (8.17 g, 18.3 mmol) in degassed toluene (500 mL), and the mixture was refluxed Lower the heat for 2 hours. The reaction mixture was cooled to room temperature, diluted with toluene and filtered through celite. The filtrate was diluted with water and extracted with toluene, and the combined organic phases were evaporated under vacuum. The residue was filtered through silica gel and recrystallized to obtain Intermediate 1-A (8.03 g, 80% of theory).

[0046]Mass Spectrum m / z: 615.13 (calculated: 615.12). Theoretical element content (%)C 34 h 30 BrNO: C, 74.45; H, 5.51; Br, 14.57; N, 2.55; O, 2.92 Measured element content (%): C, 74.44; H, 5.51; Br, 14.58; The above results confirmed that the obtained product was the target product.

[0047] Preparation of compound 1:

[0048]

[0049] Add 1-a (10g, 59.1mmol), 1-A (3...

Embodiment 2

[0051] Embodiment 2: the preparation of compound 36

[0052] The synthesis steps of intermediate 36-A are the same as those of 1-A in Example 1.

[0053] Preparation of compound 36:

[0054]

[0055] Add 5-a (16.27g, 59.1mmol), 5-A (27.44g, 59.1mmol), tris(dibenzylideneacetone) dipalladium (0.67g, 0.58mmol), tri-tert-butyl Phosphine (15%, 0.15g), sodium tert-butoxide (0.9g), toluene (400ml), stirred at 60°C for 12 hours. After the reaction solution was cooled, it was filtered with a silica gel filter, and after the solution was concentrated, it was subjected to column chromatography with dichloromethane and hexane to obtain compound 36 (35.13 g, 80%).

[0056] Mass Spectrum m / z: 742.38 (calculated: 742.37). Theoretical element content (%)C 52 h 46 N 4 O: C, 84.06; H, 6.24; N, 7.54; O, 2.15 The measured element content (%): C, 84.08; H, 6.24; N, 7.54; O, 2.17. The above results confirmed that the obtained product was the target product.

Embodiment 3

[0057] Embodiment 3: the preparation of compound 39

[0058] The synthesis steps of intermediate 39-A are the same as those of 1-A in Example 1.

[0059] Preparation of Compound 39:

[0060]

[0061] Add 39-a (16.63g, 59.1mmol), 39-A (36.44g, 59.1mmol), tris(dibenzylideneacetone) dipalladium (0.67g, 0.58mmol), tri-tert-butyl Phosphine (15%, 0.15g), sodium tert-butoxide (0.9g), toluene (400ml), stirred at 60°C for 12 hours. After the reaction solution was cooled, it was filtered with a silica gel filter, and after the solution was concentrated, it was subjected to column chromatography with dichloromethane and hexane to obtain compound 39 (35.41 g, 80%).

[0062] Mass Spectrum m / z: 748.27 (calculated: 748.26). Theoretical element content (%)C 50 h 40 N2OS 2 : C, 80.18; H, 5.38; N, 3.74; O, 2.14; S, 8.56. Measured element content (%): C, 80.18; H, 5.39; N, 3.74; O, 2.13; S, 8.56. The above results confirmed that the obtained product was the target product.

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PUM

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Abstract

The invention provides a heteroanthracene derivative and an organic light-emitting device thereof, and belongs to the technical field of organic photoelectric materials. The heteroanthracene derivative is capable of increasing the hole movement degree through regulation of R1 and R2 groups and Ar1 and Ar2 groups on the heteroanthracene derivative. The heteroanthracene derivative disclosed by the invention can be used in the organic light-emitting device, can be particularly used as an object doping material of a light emitting layer in the organic light-emitting device and has the characteristics of long service life and high efficiency.

Description

technical field [0001] The invention relates to the technical field of organic photoelectric materials, in particular to a xanthene derivative and an organic light-emitting device thereof. Background technique [0002] Organic light-emitting diodes (OLEDs) have great application potential in the fields of flat-panel displays and solid-state lighting due to their advantages of flexibility, thinness, portability, low cost, low power consumption, fast response, high luminous efficiency, and large-area preparation. Organic electroluminescence technology is very promising to become a new generation of flat panel display technology, and OLED is also favored by more and more international research institutions as a new generation of solid-state lighting source and backlight source for liquid crystal display. [0003] The development history of OLED technology is inseparable from the development of OLED materials and devices. With the development of organic light-emitting materials...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D265/38C07D279/22C07D241/46C07D219/02C07D401/12C07D401/14C07D403/12C07D403/14C07D413/12C07D413/14C07D417/12C07D417/14C07D409/12C07D409/14C07D405/12C09K11/06H01L51/50H01L51/54
Inventor 蔡辉王雪
Owner CHANGCHUN HYPERIONS TECH CO LTD
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