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Acridine derivative and organic light emitting device with same

A technology of organic light-emitting devices and derivatives, used in light-emitting materials, organic chemistry, electrical solid devices, etc., to achieve high efficiency, long life, and excellent heat resistance.

Inactive Publication Date: 2018-02-16
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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  • Acridine derivative and organic light emitting device with same
  • Acridine derivative and organic light emitting device with same
  • Acridine derivative and organic light emitting device with same

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0041] Embodiment 1: the preparation of compound 1

[0042]

[0043]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-bis A solution of isopropylacridine (4.82g, 18.3mmol) and 4,9 dibromo-1,6 diisopropylpyrene (8.13g, 18.3mmol) in degassed toluene (500mL), and the mixture was Heat 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 (9.17 g, 80% of theory).

[0044] Mass Spectrum m / z: 625.24 (calculated: 625.23). Theoretical element content (%)C 41 h 40 BrN: C, 78.58; H, 6.43; Br, 12.75; N, 2.24 Measured element content (%): C, 78.58; H, 6.43; Br, 12.76;...

Embodiment 2

[0049] Embodiment 2: the preparation of compound 7

[0050] The synthesis steps of intermediate 7-A are the same as those of 1-A in Example 1.

[0051] Preparation of Compound 7:

[0052]

[0053] Add 7-a (15.32g, 59.1mmol), 7-A (37.03g, 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 (38.06 g, 80%).

[0054] Mass Spectrum m / z: 804.42 (calculated: 804.41). Theoretical element content (%)C 59 h 52 N 2 O: C, 88.02; H, 6.51; N, 3.48; O, 1.99 Measured element content (%): C, 88.01; H, 6.52; N, 3.49; O, 1.98. The above results confirmed that the obtained product was the target product.

Embodiment 3

[0055] Embodiment 3: the preparation of compound 16

[0056] The synthesis steps of intermediate 16-A are the same as those of 1-A in Example 1.

[0057] Preparation of compound 16:

[0058]

[0059] Add 16-a (16.27g, 59.1mmol), 16-A (37.03g, 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 16 (38.82 g, 80%).

[0060] Mass Spectrum m / z: 820.40 (calculated: 820.39). Theoretical element content (%)C 59 h 52 N 2 S: C, 86.30; H, 6.38; N, 3.41; S, 3.90 Measured element content (%): C, 86.31; H, 6.37; N, 3.40; S, 3.91. 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 an acridine derivative and an OLED with same and relates to the technical field of organic optoelectronic materials. In the invention, hole movement degree is increased by adjusting the R1, R2, R3, R4, Ar1 and Ar2 groups of the acridine derivative. The acridine derivative can be used in the OLED, especially as an object doping material of a luminescent layer in the OLED. Theacridine derivative is long in service life and high in efficiency and can effectively improve the photoelectric performance of the OLED and the service life of the OLED. The acridine derivative canbe used for flat panel display, planar illuminants, surface light emitting OLED illuminants for illumination, flexible illuminants, duplicators, printers, LCD backlights, or a light source, a displaypanel and an indicator in a dosing machine, etc.

Description

technical field [0001] The invention relates to the technical field of organic photoelectric materials, in particular to an acridine derivative and an organic light-emitting device thereof. Background technique [0002] Organic light-emitting diodes (OLEDs) refer to diodes in which organic light-emitting materials emit light under the action of current or electric field, which can directly convert electrical energy into light energy. According to the molecular weight of organic electroluminescent materials, they can be divided into small molecule organic electroluminescent materials and high molecular organic electroluminescent materials. Among the currently disclosed luminescent materials, small molecule electroluminescent materials have high fluorescence quantum efficiency, are easy to purify, and have better luminous brightness and color purity than polymer materials. Therefore, the application of small molecule electroluminescent materials to light emitting devices has b...

Claims

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Application Information

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