Ortho-substituted thermally activated delayed fluorescence material and organic light-emitting device comprising same
A technology of luminescent materials and chemical formulas, applied in luminescent materials, organic semiconductor devices, organic chemistry, etc., can solve the problems of application limitations, instability of blue luminescent materials, high price, etc., and achieve the effect of delayed fluorescence
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[0129] [Experimental examples (Examples)]
[0130] [Reaction 1]
[0131]
[0132] In the reaction formula 1, in R 1 and R 2 When both are hydrogen, it is compound 1, in R 1 is methyl, R 2 It is compound 2 when it is hydrogen, and in R 1 is tert-butyl, R 2 When it is hydrogen, it is compound 3, at R 1 is hydrogen, R 2 Compound 37 when it is methyl.
Synthetic example 1
[0133] Synthesis Example 1: Synthesis of Compound 1
[0134] step 1: Carbazole (10.0g, 59.8mmol), 1,2 dibromobenzene (21.16g, 89.71mmol), potassium carbonate (16.53g, 119.61mmol) and cuprous iodide (CuI) (5.69g, 29.90mmol) After dissolving in 250 ml of N,N-dimethylacetamide, the oxygen in the solution was removed by nitrogen bubbling. After oxygen removal, the loop was stirred for 24 hours. After extracting the reaction solution with dichloromethane, column chromatography was performed using a dichloromethane / hexane mixed solvent as a developing solvent (eluent) to obtain 15.99 g of 9-(2-bromophenyl)carbazole. 9-(2-Bromophenyl)carbazole: mass analysis (El) m / z 322[(M+H)+]
[0135] step 2 : 9-(2-bromophenyl)carbazole (10g, 31.03mmol), 4,4,4`,4`,5,5,5`,5`-octamethyl-2,2`- (1,2,3-Dioxaborane) (11.82g, 46.55mmol), potassium acetate (9.14g, 93.11mmol), 1,1`-bis(diphenylphosphine)dipentyliron-palladium (II) (0.76g, 0.93mmol) was dissolved in 180ml of 1,4-dioxane, and the o...
Synthetic example 2
[0138] Synthesis Example 2: Synthesis of Compound 2
[0139] Compound 2 was obtained by the same method as Synthesis Example 1 except that 3,6-dimethylcarbazole was used instead of carbazole in Step 1 of Synthesis Example 1, and the yield was 83%.
[0140] Compound 2 : mass analysis (FAB) m / z 502 [(M+H) + ]. Elemental Analysis Theoretical Value C 35 h 26 N 4 : C (83.64%) H (5.21%) N (11.15%) Measured value: C (83.69%) H (5.26%) N (11.09%). 1 HNMR (500MHz, CDCl 3 ): 8.50(d, 1H), 8.00(d, 4H), 7.78(t, 3H), 7.73(t, 1H), 7.67(d, 1H), 7.47(t, 2H), 7.31(t, 4H) , 7.11 (d, 2H), 7.06 (d, 2H), 2.49 (s, 6H).
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