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Electron transport material and organic electroluminescent element using same

A carbon number and aryl group technology, applied in the field of new electron transport materials, can solve the problems of low Tg and impracticality of compounds

Active Publication Date: 2015-02-25
爱思开新材料捷恩智株式会社
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The compounds described in Non-Patent Document 1 have low Tg and are not practical

Method used

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  • Electron transport material and organic electroluminescent element using same
  • Electron transport material and organic electroluminescent element using same
  • Electron transport material and organic electroluminescent element using same

Examples

Experimental program
Comparison scheme
Effect test

Embodiment

[0662] Hereinafter, the present invention will be described in more detail based on examples. First, synthesis examples of benzo[a]carbazole compounds used in Examples will be described below.

Synthetic example 1

[0663] [Synthesis Example 1] Synthesis of Compound (1-1-66)

[0664]

[0665] [chem 229]

[0666]

[0667] Under a nitrogen atmosphere, 13.13 g of 1-chloro-4-methoxy-2-nitrobenzene, 15.56 g of (6-methoxynaphthalen-2-yl) boric acid, tetrakis (triphenylphosphine) palladium (O )(Pd(PPh 3 ) 4 ) 2.43 g, 29.72 g of tripotassium phosphate, and 280 ml of a mixed solvent of toluene and ethanol (toluene / ethanol=4 / 1 (volume ratio)) were added to the flask and stirred for 5 minutes. Next, 28 ml of pure water was added, and reflux was performed for 5 hours. After completion of heating, the reaction solution was cooled, and the precipitated solid was collected by filtration to obtain crude product 1. The filtrate was separated, and the organic layer was dried over anhydrous sodium sulfate. The desiccant was removed by filtration, the solvent was distilled off under reduced pressure, and the obtained solid was obtained as crude product 2. The above-mentioned crude product 1 and cr...

Synthetic example 2

[0695] [Synthesis Example 2] Synthesis of Compound (1-1-758)

[0696]

[0697] [chem 236]

[0698]

[0699] Under nitrogen atmosphere, compound (a-5a) 2g, 3-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl ) pyridine 2.01g, tetrakis (triphenylphosphine) palladium (O) (Pd (PPh 3 ) 4 ) 0.20 g, 2.89 g of tripotassium phosphate, and 14 ml of N,N-dimethylacetamide were added to the flask, stirred, and then heated at 120° C. for 4 hours. After the reaction was completed, pure water was added to the reaction solution, and the precipitated solid was collected by filtration, and then the obtained solid was purified using a silica gel column (solvent: toluene / ethyl acetate=2 / 1 (volume ratio)), Further, purification by sublimation was carried out to obtain the target compound (1-1-758): 11-phenyl-3,9-bis(3-pyridin-3-yl)phenyl-11H-benzo[a]carbazole 0.53 g (yield: 25%). The structure of the compound (1-1-758) was confirmed by MS spectrum and NMR measurement.

[0700] 1 H-...

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Abstract

A benzo[a]carbazole compound represented by formula (1) of the present invention is an electron transport material that contributes to increasing the lifespan, the high light-emitting efficiency, and the like of an organic electroluminescent element. Use of the compound in the production of an organic electroluminescent element enables the production of an organic electroluminescent element having high light-emitting efficiency and stabling operating characteristics over a long period of time. In formula (1): a, b, c, and d are 1 or 0; a and b are not 0 simultaneously; Py1 and Py2 are a pyridyl or bipyridyl; if a is 0, Ar1 is hydrogen or an aryl, if a is 1, Ar1 is an arylene, if b is 0, Ar2 is hydrogen or an aryl, and if b is 1, Ar2 is an arylene; A is an aryl; and R1-R8 each represent hydrogen, an alkyl, a cycloalkyl, an aryl, or a heteroaryl.

Description

technical field [0001] The present invention relates to a novel electron transport material having a pyridyl group, an organic electroluminescence device (hereinafter, sometimes abbreviated as an organic electroluminescence (EL) device or simply a device) using the electron transport material, and the like. Background technique [0002] In recent years, an organic EL element has attracted attention as a next-generation full-color flat panel display and has been actively researched. In order to promote the practical use of organic EL elements, reduction in driving voltage and long life of the element are essential elements, and new electron transport materials have been developed to achieve these elements. In particular, it is necessary to reduce the driving voltage of the blue element and increase its life. In Patent Document 1 (Japanese Patent Application Laid-Open No. 2003-123983), it is described that phenanthroline derivatives or 2,2'-bipyridyl compounds which are analo...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D401/04C07D401/10C07D401/14H01L51/50
CPCC07D401/14H01L51/0072H01L51/0067C07D401/10C07D401/04H10K85/624H10K85/626H10K85/654H10K85/6572C07D209/82C09K11/06H10K50/00
Inventor 王国防小野洋平
Owner 爱思开新材料捷恩智株式会社