Electron transport material or electron injection material containing alkyl-substituted polycyclic aromatic compound

An electron injection material and electron transport material technology, which is applied in the fields of display devices, lighting devices, and organic electroluminescence elements, and can solve the problems of undocumented NO linking compound manufacturing method, different electronic states, unknown characteristics, etc.

Pending Publication Date: 2020-11-13
KWANSEI GAKUIN EDUCTIONAL FOUND +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

The above document evaluates, for example, the charge transport properties of the NO-linking compound (compound 1 on page 63), but does not describe the production method of materials other than the NO-linking compound. In addition, if the linking elements are different, the overall compound The electronic state of the compound is different, therefore, the properties obtained from materials other than NO linking compounds are still unknown

Method used

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  • Electron transport material or electron injection material containing alkyl-substituted polycyclic aromatic compound
  • Electron transport material or electron injection material containing alkyl-substituted polycyclic aromatic compound
  • Electron transport material or electron injection material containing alkyl-substituted polycyclic aromatic compound

Examples

Experimental program
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Embodiment

[0570] Hereinafter, although an Example demonstrates this invention more concretely, this invention is not limited to these Examples. First, a synthesis example of a polycyclic aromatic compound will be described below.

Synthetic example (1

[0571] Synthesis Example (1): Synthesis of Compound (1-101)

[0572] [chem 93]

[0573]

[0574] Under nitrogen atmosphere, put 1,3-dibromo-5-fluorobenzene (50.0g), carbazole (36.2g), potassium carbonate (54.0g) and N-methylpyrrolidone (NMP, 250mL) into the flask , stirred at 170°C for 6 hours. After the reaction, the reaction liquid was cooled, and after adding water, the precipitate was filtered. After the precipitate was washed with water and methanol and dried, it was purified with a silica gel column (eluent: toluene / heptane = 2 / 8 (volume ratio)), and the crude product was dissolved in toluene and purified with heptane It was reprecipitated with alkane to obtain compound (A) (55.3 g).

[0575] [chem 94]

[0576]

[0577] Under a nitrogen atmosphere, compound (A) (25.0g), 3-(2-methylphenyl)phenol (25.2g), copper iodide (0.60g), tris(acetylacetonate)iron (2.20g), Potassium carbonate (34.0 g) and N-methylpyrrolidone (NMP, 100 mL) were put into the flask, and it st...

Synthetic example (2

[0585] Synthesis Example (2): Synthesis of Compound (1-201)

[0586] [chem 97]

[0587]

[0588] Under nitrogen atmosphere, 1,3-dibromo-5-fluorobenzene (80.0 g), 4-(9H-carbazol-9-yl)phenylboronic acid (130.9 g), dichlorobis( Di-tert-butyl(4-dimethylaminophenyl)phosphino)palladium (Pd-132, 1.47g), potassium phosphate (176g), toluene (600mL), isopropanol (IPA, 150mL) and water ( 70 mL) into the flask and stirred at reflux temperature for 2 hours. After cooling the reaction liquid, water was added and stirred, toluene was added and liquid separation extraction was performed, and the water layer was removed, and the organic layer was further washed with water. Further, the crude product obtained by concentrating the organic layer under reduced pressure was washed with a mixed solution of heptane / ethyl acetate=4 / 1 (volume ratio), thereby obtaining a compound (C) (166 g).

[0589] [chem 98]

[0590]

[0591] Under nitrogen atmosphere, compound (C) (25.0g), 3-(2-methylphenyl)...

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Abstract

By introducing an alkyl group at a specified position (specifically, an ortho position) of a polycyclic aromatic compound in which a plurality of aromatic rings are linked by a boron atom and an oxygen atom or the like, the present invention provides a compound that is suitable as an electron transport material, such as an organic EL element that exhibits superior luminous efficiency and element life.

Description

technical field [0001] The present invention relates to an electron transport material or an electron injection material (hereinafter also collectively referred to as "polycyclic aromatic compound") containing an alkyl-substituted polycyclic aromatic compound and a multimer thereof (hereinafter also collectively referred to as "polycyclic aromatic compound") Electron transport materials"), and organic electroluminescent elements using them, as well as display devices and lighting devices. In addition, in this specification, an "organic electroluminescence element" may be expressed as an "organic EL (electroluminescence) element" or simply as a "device". Background technique [0002] In the past, display devices using light-emitting elements that perform electroluminescence have been researched in various ways because they can save power or reduce thickness. Further, organic electroluminescent elements made of organic materials have been actively studied because they can be e...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): H01L51/50G09F9/30H01L27/32C07F5/02
CPCC07F5/02G09F9/30H10K59/00H10K50/00G09F9/33H10K85/322H10K50/16H10K50/171
Inventor 畠山琢次笹田康幸枝连一志影山明子今井宏之
Owner KWANSEI GAKUIN EDUCTIONAL FOUND
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