A spirodimethylanthrafluorene organic compound and its application in organic electroluminescent devices
A technology of spirodimethylanthrafluorenes and dimethylanthrafluorenes, which is applied to spirodimethylanthrafluorene organic compounds and their application in organic electroluminescent devices, and can solve problems such as very different performances , to achieve the effects of not being easy to aggregate, improving stability, and maintaining film stability
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Embodiment 1
[0038] Embodiment 1: the synthesis of intermediate A
[0039]
[0040] Take the synthesis of intermediate A1 as an example:
[0041]
[0042] In a 250ml three-neck flask, under nitrogen atmosphere, add 0.01mol 1-benzidine, 0.012mol 2-bromobiphenyl, 0.03mol potassium tert-butoxide, 1×10 -4 molPd 2 (dba) 3 , 1×10 -4 mol of tri-tert-butylphosphine, 150ml of toluene, heated to reflux for 12 hours, sampled on a plate, and the reaction was complete; naturally cooled, filtered, the filtrate was rotary evaporated, and passed through a silica gel column to obtain intermediate A1 with a HPLC purity of 99.5% and a yield of 82.7%; Elemental analysis structure (molecular formula C 19 h 11 N): theoretical value C, 89.68; H, 5.96; N, 4.36; tested value: C, 89.65; H, 5.95N, 4.38. ESI-MS(m / z)(M + ): The theoretical value is 321.42, and the measured value is 321.58.
[0043] Intermediate A was prepared by the synthesis method of Intermediate A1, and the specific structure is shown i...
Embodiment 2
[0046] Embodiment 2: the synthesis of intermediate B
[0047]
[0048] In a 250ml three-necked flask, add 0.01mol of raw material III, 0.012mol of raw material IV-1 (or raw material IV-2), and 0.03mol of KN(SiMe) under a nitrogen atmosphere. 3 , 150ml of dioxane, heated at 80°C for 16 hours, sampled and plated, and the reaction was complete; naturally cooled, filtered, the filtrate was rotary evaporated, and passed through a silica gel column to obtain intermediate B-1 (or intermediate B-2), HPLC Purity 99.4% (99.0%), yield 90.5% (84.9%);
[0049] B-1(C 28 h 21 Br) elemental analysis: theoretical value C, 76.89; H, 4.84; test value: 76.74; H, 4.89;
[0050] ESI-MS(m / z)(M + ): The theoretical value is 437.78, and the measured value is 437.25;
[0051] B-2(C 28 h 21 Br) element analysis: theoretical value C, 76.89; H, 4.84; test value: 76.65; H, 4.91;
[0052] ESI-MS(m / z)(M + ): The theoretical value is 437.78, and the measured value is 437.31;
Embodiment 3
[0053] Embodiment 3: the synthesis of compound 12:
[0054]
[0055] In a 250ml three-necked flask, add 0.01mol of intermediate A2, 0.012mol of intermediate A2, 0.03mol of potassium tert-butoxide, 1×10 -4 molPd 2 (dba) 3 , 1×10 -4 mol of tri-tert-butylphosphine, 150ml of toluene, heated to reflux for 12 hours, sampling point plate, the reaction was complete; naturally cooled, filtered, the filtrate was rotary evaporated, and passed through a silica gel column to obtain compound 12 with a HPLC purity of 99.4% and a yield of 80.3%; Analytical structure (molecular formula C 52 h 39 N): theoretical value C, 92.13; H, 5.80; N, 2.07; tested value: C, 92.08; H, 5.85; N, 2.01. ESI-MS(m / z)(M + ): The theoretical value is 677.87, and the measured value is 676.54.
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