Ultraviolet absorbing compound and sealant composition comprising same
A compound and ultraviolet technology, applied in the direction of non-polymer organic compound adhesives, adhesive additives, non-polymer adhesive additives, etc., can solve the problems of equipment function decline, organic light-emitting device degradation, degradation, etc.
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[0070] The preparation method of the ultraviolet absorbing compound of chemical formula 1 according to one aspect of the present invention comprises: making the fluorenyl magnesium halide of the following chemical formula 1 react with the cyanuric chloride of the following chemical formula 2 to obtain the bisfluorenyl cyanuric chloride of the following chemical formula 3 Step; make the bisfluorenyl cyanuric chloride of above-mentioned chemical formula 3 react with the resorcinol of following chemical formula 4 to obtain the step of the bisfluorenyl cyanurate compound of following chemical formula 5 that the resorcinol replaces; And make The step of reacting the above-mentioned resorcinol-substituted bisfluorenyl cyanurate compound with an alkyl halide to obtain a compound of formula I,
[0071] Chemical formula 1:
[0072]
[0073] Chemical formula 2:
[0074]
[0075] Chemical formula 3:
[0076]
[0077] Chemical formula 4:
[0078]
[0079] Chemical formula 5...
preparation example 1
[0119] Preparation Example 1: Preparation of Compound 1
[0120] (1) Synthesis of compound 1-a
[0121]
[0122] 6.8 g (282 mmol) of magnesium, a small amount of iodine and 200 ml of tetrahydrofuran were added to a dry 2 L reactor and stirred for 15 minutes under nitrogen atmosphere. After dissolving 62.8 g (256 mmol) of 2-bromofluorene in tetrahydrofuran, it was added dropwise to the reactor at 0° C. and stirred under reflux for about 2 hours.
[0123] The reactant was added dropwise at 0°C to a tetrahydrofuran solution in which 23.6 g (128 mmol) of cyanuric chloride was dissolved, and the resulting mixture was stirred at 50°C under reflux for 12 hours. After completion of the reaction, an aqueous ammonium chloride solution was slowly added dropwise at 0°C to extract an organic layer, and then concentrated. The concentrate was purified by column chromatography to obtain 42.6 g of the above compound 1-a (75% yield).
[0124] 1 H NMR (300MHz, CDCl 3 ): δ7.98 (2H, d, J=8...
preparation example 2
[0133] Preparation Example 2: Preparation of Compound 2
[0134] (1) Synthesis of compound 2-a
[0135]
[0136] 6.8 g (282 mmol) of magnesium, a small amount of iodine and 200 ml of tetrahydrofuran were added to a dry 2 L reactor and stirred for 15 minutes under nitrogen atmosphere. After dissolving 77.1 g (256 mmol) of 2-bromo-9,9-diethylfluorene in tetrahydrofuran, this was added dropwise to the above-mentioned reactor at 0° C., followed by stirring under reflux for about 2 hours.
[0137] The above reactant was added dropwise at 0°C to a tetrahydrofuran solution in which 23.6 g (128 mmol) of cyanuric chloride was dissolved, and the resulting mixture was stirred at 50°C under reflux for 12 hours. After completion of the reaction, an aqueous ammonium chloride solution was slowly added dropwise at 0°C to extract an organic layer, and then concentrated. The concentrate was purified by column chromatography to obtain 55.5 g of Compound 2-a (78% yield).
[0138] 1 H NMR (...
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