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Organic compound, light-emitting element, light-emitting device, electronic device, and lighting device

專利號
US10868258B2
公開日期
2020-12-15
申請人
Semiconductor Energy Laboratory Co., Ltd.
發(fā)明人
Miki Kurihara; Hideko Yoshizumi; Hiromitsu Kido; Tatsuyoshi Takahashi; Satoshi Seo
IPC分類
H01L51/50; H01L51/00; C07D491/048; C07D495/04
技術(shù)領(lǐng)域
emitting,light,skeleton,8cz,layer,compound,in,phenyl,material,electron
地域: Kanagawa-ken

摘要

A novel organic compound is provided. Moreover, a light-emitting element with high emission efficiency and a long lifetime is provided. A novel organic compound having a bicarbazole skeleton and a benzofuropyrimidine skeleton or a benzothienopyrimidine skeleton that includes at least one condensed ring or two condensed rings is provided. Moreover, a light-emitting element including the organic compound is provided.

說明書

In this example, a method for synthesizing one of the compounds that are one embodiment of the present invention and represented by General Formula (G0), 8-(9H-carbazol-9-yl)-4-[3-(9′-phenyl-2,3′-bi-9H-carbazol-9-yl)phenyl]benzofuro[3,2-d]pyrimidine (abbreviation: 8Cz-4mPCCzPBfpm) (Structural Formula (104)), and characteristics thereof are described.

Synthesis Example 3 Step 1: Synthesis of 9-(3-bromophenyl)-9′-phenyl-2,3′-bi-9H-carbazole

Into a 500-mL three-neck flask, 16 g of 9-phenyl-2,3′-bi-9H-carbazole, 14 g of 3-bromoiodobenzene, and 12 g of tripotassium phosphate were put, and the air in the flask was replaced with nitrogen. Then, 190 mL of 1,4-dioxane, 0.65 g of trans-1,2-diaminocyclohexane, and 0.54 g of copper(I) iodide were added thereto, and the mixture was heated under a nitrogen stream at 120° C. for 8 hours. Furthermore, 3.0 g of tripotassium phosphate, 0.16 g of trans-1,2-diaminocyclohexane, and 0.13 g of copper(I) iodide were added, and the mixture was heated under a nitrogen stream at 120° C. for 14 hours. Water and ethanol were added to the obtained reaction mixture and filtration was performed. The filtrate was extracted with toluene, the solution of the extract was washed with saturated saline, magnesium sulfate was added, and then filtration was performed. The solvent of the filtrate was distilled off and the residue was dissolved in hot toluene. Purification was performed by silica gel column chromatography using a mixed solvent of a 1:2 ratio of toluene to hexane as a developing solvent, whereby 16 g of a target pale yellow solid was obtained in a yield of 72%. The synthesis scheme of Step 1 is shown in (C-1) below.

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