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Organic electroluminescent compound and organic electroluminescent device comprising the same

An electroluminescent device and compound technology, applied in organic chemistry, luminescent materials, circuits, etc., can solve the problems of high driving voltage, short operating life, poor thermal stability, etc., and achieve the effect of high luminous efficiency and low driving voltage

Pending Publication Date: 2021-08-17
ROHM & HAAS ELECTRONICS MATERIALS LLC
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] However, although conventional materials provide good light-emitting characteristics, they have the following disadvantages: (1) Due to their low glass transition temperature and poor thermal stability, they may degrade during the high-temperature deposition process in vacuum and may shorten the device life span
Although OLEDs containing phosphorescent host materials offer higher current efficiencies (cd / A) than OLEDs containing fluorescent materials, they require considerably higher drive voltages
Therefore, there is no advantage in terms of power efficiency (lm / W)
(3) In addition, OLEDs have a short operating life and still need to improve luminous efficiency
[0006] In order to improve luminous efficiency, operating voltage and / or lifetime, various materials or concepts for organic layers of OLEDs have been proposed, but they are not satisfactory for practical use

Method used

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  • Organic electroluminescent compound and organic electroluminescent device comprising the same
  • Organic electroluminescent compound and organic electroluminescent device comprising the same
  • Organic electroluminescent compound and organic electroluminescent device comprising the same

Examples

Experimental program
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Effect test

example 1

[0114] [Example 1] Synthesis of Compound C-1

[0115]

[0116] 1. Synthesis of compound A-2

[0117] Compound A-1 (85g, 0.359mol), bis(pinacolate) diboron (100g, 0.394mol), and (1,1'-bis(diphenylphosphino)ferrocene)dichloropalladium (II)(PdCl 2 (dppf)) (7.87 g, 0.0108 mol) was added to the flask and dissolved in potassium acetate (106 g, 1.08 mol) and 1.8 L of 1,4-dioxane, and then refluxed for 24 hours. After the reaction was completed, the organic layer was extracted with ethyl acetate, and dried over magnesium sulfate. Next, it was separated by column chromatography to obtain compound A-2 (86 g, yield: 84%).

[0118] 2. Synthesis of Compound A-3

[0119] Compound A-2 (15g, 0.0528mol), 2-bromo-1-fluoro-3-nitrobenzene (23.2g, 0.106mol), tripotassium phosphate (K 3 PO 4 ) (33.6 g, 0.158 mol), palladium acetate (1.19 g, 0.00528 mol), and Xantphos (6.11 g, 0.0106 mol) were added to the flask and dissolved in tetrahydrofuran, and then refluxed for 24 hours. After the...

example 2

[0129] [Example 2] Synthesis of Compound C-3

[0130]

[0131] Compound A-6 (2.3 g, 0.00995 mol), Compound D (3.86 g, 0.00995 mol), copper(II) sulfate (0.794 g, 0.00497 mol), and potassium carbonate (2.75 g, 0.0199 mol) were added to the flask , and dissolved in 66.3 mL of o-dichlorobenzene, and then refluxed for 24 hours. After the reaction was completed, the solvent was removed by distillation, and dissolved in ethyl acetate. The organic layer was separated and dried over magnesium sulfate. Next, it was separated by column chromatography to obtain compound C-3 (2.2 g, yield: 41.1%).

[0132] MW Tg M.P. Example 2 538.61 82.57 200.3

[0133] Hereinafter, light emission characteristics of an organic electroluminescent device including the organic electroluminescent compound of the present disclosure will be explained for a detailed understanding of the present disclosure.

example 1 and 2

[0134] [Device Examples 1 and 2] Preparation of OLEDs Comprising Host Compounds According to the Present Disclosure

[0135] OLEDs according to the present disclosure were produced. First, a transparent electrode indium tin oxide (ITO) film (10Ω / sq) (GEOMATEC CO., LTD., Japan) on a glass substrate for an OLED was subjected to sequential treatment with acetone and isopropanol. Sonicated and thereafter stored in isopropanol and then used. Next, the ITO substrate was mounted on the substrate holder of the vacuum vapor deposition equipment. Compound HI-1 was introduced into one chamber of the vacuum vapor deposition apparatus, and compound HT-1 was then introduced into the other chamber of the vacuum vapor deposition apparatus. The two materials were respectively evaporated at different rates and deposited with a doping amount of 3 wt % to form a hole injection layer with a thickness of 10 nm on the ITO substrate. Next, compound HT-1 was introduced into a chamber of a vacuum va...

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Abstract

The present disclosure relates to an organic electroluminescent compound and an organic electroluminescent device comprising the same. By comprising the organic electroluminescent compound according to the present disclosure, it is possible to provide an organic electroluminescent device having a low driving voltage and / or high luminous efficiency.

Description

technical field [0001] The present disclosure relates to an organic electroluminescent compound and an organic electroluminescent device comprising the same. Background technique [0002] TPD / Alq with green emission consisting of emissive layer and charge transport layer 3 Double-layer small-molecule organic electroluminescent devices (OLEDs) were first developed in 1987 by Tang et al. at Eastman Kodak. Since then, research on OLEDs has been rapidly commercialized. [0003] The most important factor determining the luminous efficiency in OLEDs is the light emitting material. Fluorescent materials have been widely used as light-emitting materials so far. However, in view of the mechanism of electroluminescence, phosphorescent light-emitting materials have been extensively studied since they theoretically enhance luminous efficiency by four (4) times compared with fluorescent light-emitting materials. So far, iridium(III) complexes have been widely known as phosphorescent ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D491/06C07D519/00C07D495/06C07D493/06C09K11/06H01L51/50H01L51/54H10K99/00
CPCC07D491/06C07D519/00C07D495/06C07D493/06C09K11/06C09K2211/1011C09K2211/1014C09K2211/1096C09K2211/1088C09K2211/1092C09K2211/1037C09K2211/1033C09K2211/1059C09K2211/1048C09K2211/1051C09K2211/1044H10K85/633H10K85/631H10K85/615H10K85/654H10K85/6576H10K85/6574H10K85/657H10K85/6572H10K50/11H10K50/18H10K85/342H10K2101/10H10K50/12C07D491/052C07D493/04C07D495/04H10K85/636H10K50/15H10K50/16H10K50/171
Inventor 李孝姃金荣光洪镇理
Owner ROHM & HAAS ELECTRONICS MATERIALS LLC