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Spiro-xanthene fluorene-cored compound and application thereof to organic electroluminescent devices
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A compound, xanthene technology, applied in the application field of organic electroluminescent devices, can solve problems such as disparity
Inactive Publication Date: 2019-04-05
JIANGSU SUNERA TECH CO LTD
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In addition, for the collocation of OLED devices with different structures, the photoelectric functional materials used have strong selectivity, and the performance of the same material in devices with different structures may be completely different.
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Embodiment 1
[0109] The synthesis of embodiment 1 compound 4
[0110]
[0111] In a 250ml three-neck flask, under the protection of nitrogen, add 0.01mol raw material A1, 0.012mol raw material B1, 150ml toluene and stir to mix, then add 0.03mol sodium tert-butoxide, 5×10 -5 molPd 2 (dba) 3 , 5×10 -5 mol of tri-tert-butylphosphine, heated to 105°C, refluxed for 24 hours, sampling plate, showed no remaining bromide, the reaction was complete; naturally cooled to room temperature, filtered, and the filtrate was rotary evaporated under reduced pressure (-0.09MPa, 85°C ), through a neutral silica gel column, to obtain the target product, HPLC purity 99.3%, yield 65.7%;
[0112] Elemental analysis structure (molecular formula C 40 h 29 NO): Theoretical C, 89.02; H, 5.42; N, 2.60; O, 2.96; Tested: C, 89.05; H, 5.41; N, 2.58; ESI-MS(m / z)(M + ): The theoretical value is 539.22, and the measured value is 539.31.
Embodiment 2
[0113] The synthesis of embodiment 2 compound 15
[0114]
[0115] In a 250ml three-necked flask, under the protection of nitrogen, add 0.01mol raw material A2, 0.012mol raw material B2, 150ml toluene and stir to mix, then add 0.03mol sodium tert-butoxide, 5×10 -5 molPd 2 (dba) 3 , 5×10 -5 mol of tri-tert-butylphosphine, heated to 105°C, refluxed for 24 hours, sampling plate, showed no remaining bromide, the reaction was complete; naturally cooled to room temperature, filtered, and the filtrate was rotary evaporated under reduced pressure (-0.09MPa, 85°C ), through a neutral silica gel column, to obtain the target product, HPLC purity 99.1%, yield 66.7%;
[0116] Elemental analysis structure (molecular formula C 40 h 29NS): theoretical value C, 83.90; H, 4.38; N, 2.64; O, 3.02; S, 6.05; test value: C, 83.91; ESI-MS(m / z)(M + ): The theoretical value is 529.15, and the measured value is 529.21.
Embodiment 3
[0117] The synthesis of embodiment 3 compound 20
[0118]
[0119] In a 250ml three-neck flask, under the protection of nitrogen, add 0.01mol raw material A3, 0.012mol raw material B3, 150ml toluene and stir to mix, then add 0.03mol sodium tert-butoxide, 5×10 -5 molPd 2 (dba) 3 , 5×10 -5 mol of tri-tert-butylphosphine, heated to 105°C, refluxed for 24 hours, sampling plate, showed no remaining bromide, the reaction was complete; naturally cooled to room temperature, filtered, and the filtrate was rotary evaporated under reduced pressure (-0.09MPa, 85°C ), through a neutral silica gel column, to obtain the target product, HPLC purity 98.8%, yield 65.6%;
[0120] Elemental analysis structure (molecular formula C 46 h 31 NO 2 ): theoretical value C, 87.73; H, 4.96; N, 2.22; O, 5.08; test value: C, 87.75; H, 4.97; N, 2.21; ESI-MS(m / z)(M + ): The theoretical value is 629.24, and the measured value is 629.32.
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Abstract
The invention discloses a spiro-xanthenefluorene-cored compound and application thereof to organic electroluminescent devices. Containing a s spiro-xanthenefluorene structure, the spiro-xanthenefluorene-cored compound is high in rigidity, and after being connected with the long-branch-chain structure of carbazole derivatives, has the advantages of being less prone to intermolecular crystallization and aggregation, good in film forming properties and the like. Due to the facts that the parent nucleus is bipolarized and the branch chains serve as electron-donating groups with different electron-donating capacities, the spiro-xanthene fluorene-cored compound can present different HOMO (highest occupied molecular orbital) energy levels and further can serve as different functional layer materials. Besides, the spiro-xanthene fluorene-cored compound is high in triplet stateenergy level and capable of effectively blocking energy loss and facilitating energy transferring. Therefore, whenthe spiro-xanthene fluorene-cored compound is applied to OLED (organic light emitting diode) devices, the current efficiency, the power efficiency and the external quantum efficiency of the devices can be greatly improved, and meanwhile, the service life of the devices can be significantly prolonged.
Description
technical field [0001] The invention relates to the technical field of semiconductors, in particular to a compound with spiroxanthene fluorene as the core and its application in organic electroluminescent devices. Background technique [0002] Organic electroluminescence (OLED: Organic Light Emission Diodes) device technology can not only be used to manufacture new display products, but also can be used to make new lighting products, and is expected to replace the existing liquid crystal display and fluorescent lighting, and has a very broad application prospect. The OLED light-emitting device is a sandwich structure, including electrode material film layers, and organic functional materials sandwiched between different electrode film layers. Various functional materials are superimposed on each other according to the application to form an OLED light-emitting device. As a current device, when a voltage is applied to the electrodes at both ends of the OLED light-emitting dev...
Claims
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