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.
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.