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Benzophenanthrene derivative and organic light-emitting device thereof

An organic light-emitting device and a technology of triphenylenes, which are applied in the field of triphenylene derivatives and organic light-emitting devices to achieve the effect of improving the mobility of holes

Inactive Publication Date: 2018-02-02
CHANGCHUN HYPERIONS TECH CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] Generally speaking, the direction of OLED in the future is to develop high-efficiency, high-brightness, long-life, low-cost white light devices and full-color display devices, but the industrialization process of this technology still faces many problems

Method used

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

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0040] Embodiment 1: the preparation of compound 1

[0041]

[0042] Tri-tert-butylphosphine (4.4 mL of a 1.0 M solution in toluene, 1.48 g, 0.05 mmol), palladium acetate (0.4 g, 1.83 mmol) and sodium tert-butoxide (22.7 g, 237 mmol) were added to 2.7-diisopropyl Acridine (4.82 g, 18.3 mmol) and 6,12 dibromodridine (7.07 g, 18.3 mmol) in degassed toluene (500 mL), and the mixture was heated at reflux 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 (8.32 g, 80% of theory).

[0043] Mass Spectrum m / z: 567.17 (calculated: 567.16). Theoretical element content (%)C 37 h 30BrN: C, 78.16; H, 5.32; Br, 14.05; N, 2.46 Measured element content (%): C, 78.15; H, 5.33; Br, 14.04; N, 2.47. The above re...

Embodiment 2

[0048] Embodiment 2: the preparation of compound 7

[0049] The synthesis steps of intermediate 7-A are the same as those of 1-A in Example 1.

[0050] Preparation of Compound 7:

[0051]

[0052] Add 7-a (15.32g, 59.1mmol), 7-A (33.60g, 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 7 (35.32 g, 80%).

[0053] Mass Spectrum m / z: 746.34 (calculated: 746.33). Theoretical element content (%)C 55 h 42 N 2 O: C, 88.44; H, 5.67; N, 3.75; O, 2.14 Measured element content (%): C, 88.43; H, 5.68; N, 3.74; O, 2.15. The above results confirmed that the obtained product was the target product.

Embodiment 3

[0054] Embodiment 3: the preparation of compound 19

[0055] The synthesis steps of intermediate 19-A are the same as those of 1-A in Example 1.

[0056]

[0057] Preparation of compound 19:

[0058] Add 19-a (16.27g, 59.1mmol), 19-A (33.60g, 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 19 (36.07 g, 80%).

[0059] Mass Spectrum m / z: 762.32 (calculated: 762.31). Theoretical element content (%)C 55 h 42 N 2 S: C, 86.58; H, 5.55; N, 3.67; S, 4.20 The measured element content (%): C, 86.57; H, 5.56; N, 3.66; S, 4.21. The above results confirmed that the obtained product was the target product.

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Abstract

Relating to the technical field of organic photoelectric materials, the invention provides a benzophenanthrene derivative and an organic light-emitting device thereof. The benzophenanthrene derivativeprovided by the invention improves the hole mobility through adjustment of R1, R2 and Ar1, Ar2 groups on benzophenanthrene organic compounds, can be used for an organic light-emitting device, especially can serve as a luminescent layer object doped material in the organic light-emitting device, shows high efficiency and long service life, and is superior to existing common OLED devices. The organic light-emitting device provided by the invention can be applicable to flat panel display, plane luminous bodies, surface luminescent OLED luminous bodies for illumination, flexible luminous bodies,copiers, printers, LCD backlight lamps or measuring machines' light sources, display panels, logos and the like.

Description

technical field [0001] The invention relates to the technical field of organic photoelectric materials, in particular to a triphenylene derivative and an organic light-emitting device thereof. Background technique [0002] The research work on organic electroluminescence began in the 1960s, but until 1987, Tang et al. of Kodak Company of the United States first used 8-hydroxyquinoline aluminum (Alq3) as a light-emitting material to prepare organic light-emitting diodes (OLEO), pioneering It has opened up a new situation in the research of organic electroluminescent materials and devices. This breakthrough has made OLED a hot spot in the research of light-emitting devices. Because OLED has the advantages of high brightness, wide vision, fast response, stable image, rich luminous color, high resolution, low driving voltage, full curing, ultra-thin, etc., it is widely used in mobile phones, digital cameras, DVD players, personal digital Assistants (PDAs), laptops, car stereos...

Claims

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Application Information

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IPC IPC(8): C07D219/02C07D401/12C07D405/12C07D409/12H01L51/54C09K11/06
CPCC09K11/06C07D219/02C07D401/12C07D405/12C07D409/12C09K2211/1029C09K2211/1014C09K2211/1011C09K2211/1007C09K2211/1092C09K2211/1088H10K85/622H10K85/636H10K85/633H10K85/6576H10K85/6574H10K85/6572
Inventor 蔡辉韩春雪
Owner CHANGCHUN HYPERIONS TECH CO LTD
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