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Mixture applied to hole injection layer and organic light emitting device thereof

A technology of organic light-emitting devices and hole injection layers, which is applied in the fields of electric solid-state devices, semiconductor devices, semiconductor/solid-state device manufacturing, etc., to achieve the effects of low driving voltage, high efficiency, and simple manufacturing methods

Inactive Publication Date: 2019-04-02
CHANGCHUN HYPERIONS TECH CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The vacuum evaporation method has many difficulties such as a complicated process and the need for a large evaporation device, so it is desired to form an organic light-emitting device by a wet film

Method used

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  • Mixture applied to hole injection layer and organic light emitting device thereof
  • Mixture applied to hole injection layer and organic light emitting device thereof
  • Mixture applied to hole injection layer and organic light emitting device thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0067] Embodiment 1: the preparation of compound TM8

[0068]

[0069] Add NaH (1.6 g, 16 mmol) into 40 mL of ethylene glycol dimethyl ether, and slowly drop it into 10 mL of pentafluorophenylacetonitrile (4 g, 20 mmol) in ethylene glycol dimethyl ether with stirring in an ice bath. The ice bath was removed, and the reaction solution was gradually warmed up to room temperature, and reacted at room temperature for 15 minutes. The reaction liquid was cooled to 0°C again, and a solution of tetrachlorocyclopropene (0.9 g, 5 mmol) in 10 mL of ethylene glycol dimethyl ether was slowly added dropwise into the reaction liquid. The reaction solution gradually turned dark red, warmed up to room temperature, and continued to stir for 24 h. After the reaction, pour the reaction solution into 1.2L of ice water, adjust the pH value of the resulting mixture to 1 with concentrated hydrochloric acid (add about 24ml of hydrochloric acid), then extract with 3×50ml of chloroform, combine the ...

Embodiment 2

[0071] Embodiment 2: the preparation of compound TM10

[0072]

[0073] Compound 1-2 in Example 1, ie, pentafluorophenylacetonitrile, was replaced by equimolar compound 2-2, and the other steps were the same to obtain compound 10. Mass Spectrum m / z: 800.75 (calculated: 800.98). Theoretical element content (%)C 30 f 21 N 3 : C, 44.97; F, 49.79; N, 5.24 The measured element content (%): C, 44.98; F, 49.77; N, 5.25. The above results confirmed that the obtained product was the target product.

Embodiment 3

[0074] Embodiment 3: the preparation of compound 1

[0075]

[0076] Synthesis of Intermediate A1

[0077] Tri-tert-butylphosphine (3 mL of a 1.0M solution in toluene, 7.32 mmol), palladium acetate (0.4 g, 1.83 mmol) and sodium tert-butoxide (22.8 g, 238 mmol) were added to bis-(4-biphenyl) A solution of the amine (58.7 g, 183 mmol) and 4-bromo-4-iodobiphenyl (65.5 g, 183 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 (heptane / dichloromethane) and crystallized from isopropanol. Intermediate A1 was obtained (90.7 g, 90% of theory).

[0078] Mass Spectrum m / z: 551.13 (calculated: 551.12). Theoretical element content (%)C 36 h 26 BrN: C, 78.26; H, 4.74; Br, 14.46;...

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Abstract

The invention discloses a mixture applied to a hole injection layer and an organic light emitting device thereof, and relates to the technical field of organic light emitting materials. The mixture comprises three components: a radialene compound, an aromatic amine compound including carbazole groups and a solvent, wherein the substituent group of the aromatic amine compound is selected from a series of electron deficiency groups, particularly the electron deficiency groups with nitrogen heteroatoms, such as triazine groups, pyrimidine groups and pyridine groups; the electron deficiency performance of the radialene compound is more prominent via the electron deficiency groups with the nitrogen heteroatoms; the aromatic amine compound is provided with carbazole electron-donating groups, andmost of the structure has deuterium atoms but no hydrogen atoms; the carbon-deuterium bond is more stable than the carbon-hydrogen bond by about 6-9 times, and thus the more stable compound is acquired. The acquired mixture in a wet film mode is used for preparing the organic light emitting device, particularly the hole injection material in the organic light emitting device; the device has the advantages of low drive voltage, high efficiency, high brightness and long service life, and is better than the currently common OLED devices.

Description

technical field [0001] The invention relates to the technical field of organic photoelectric materials, in particular to a mixture used for a hole injection layer and an organic light emitting device thereof. Background technique [0002] In recent years, Organic Light Emitting Diode (OLED: Organic Light Emitting Diode) as a new and promising display technology has gradually entered people's field of vision. OLED is an electroluminescent device formed by a multilayer organic thin film structure, wherein the organic thin film is a film of organic light-emitting material formed on a substrate by evaporation, deposition or spin coating process. The vacuum evaporation method has many difficulties such as a complicated process and the need for a large evaporation apparatus, so it is desired to form an organic light emitting device by a wet film. [0003] Typically, OLEDs have a layered or laminated structure. For example, a typical OLED has an anode / organic light-emitting layer...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): H01L51/50H01L51/54
CPCH10K85/60H10K85/624H10K85/615H10K85/631H10K85/636H10K85/633H10K85/654H10K85/6576H10K85/6574H10K85/6572H10K50/17
Inventor 蔡辉
Owner CHANGCHUN HYPERIONS TECH CO LTD
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