Compound taking anthrone as core and application of compound in OLED device
Active Publication Date: 2017-03-01
JIANGSU SUNERA TECH CO LTD
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[0005] Although theoretically TADF materials can achieve 100% exciton utilization, there are actually the following problems: (1) The T1 and S1 states of the designed molecules have strong CT characteristics, and the very small S1-T1 state energy gap, although it can High T through TADF process 1 →S 1 state exciton conversion rate, but at the same time lead to a low S1 state radiative transition rate, therefore, it is difficult to have both (or simultaneously achieve) high exciton utilization efficiency and high fluorescence radiation efficiency; (2) Even if doped devices have been used to alleviate the T excitation Subconcentration quenching effect, the efficiency of most TADF material devices has a serious roll-off at high current densities
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Embodiment 1
[0068] Synthesis of Example 1 Compound C03
[0069]
[0070] In a 250ml four-neck flask, under a nitrogen atmosphere, add 0.01mol 2-bromo-10,10-dimethyl-10H-anthrone, 0.015mol compound A1, 0.03mol sodium tert-butoxide, 1×10 -4 mol Pd 2 (dba) 3 , 1×10 -4 mol of tri-tert-butylphosphine, 150ml of toluene, heated to reflux for 24 hours, sampling plate, reaction complete, natural cooling, filtration, filtrate rotary evaporation, silica gel column, to obtain the target product with a purity of 99.40% and a yield of 36.90%.
[0071] HPLC-MS: The molecular weight of the material is 686.29, and the measured molecular weight is 686.31.
Embodiment 2
[0072] Example 2 Synthesis of Compound C11
[0073]
[0074] In a 250ml four-neck flask, under nitrogen atmosphere, add 0.01mol 3-(3-bromophenyl)-10,10-diphenyl-10H-anthrone, 0.015molA2, 0.03mol sodium tert-butoxide, 1×10 -4 mol Pd 2 (dba) 3 , 1×10 -4 mol tri-tert-butylphosphine, 150ml toluene, heating and reflux for 24 hours, sampling point plate, reaction complete, natural cooling, filtration, filtrate rotary evaporation, silica gel column, to obtain the target product with a purity of 97.6% and a yield of 45.8%.
[0075] HPLC-MS: The molecular weight of the material is 912.41, and the measured molecular weight is 912.59.
Embodiment 3
[0076] Synthesis of Example 3 Compound C24
[0077]
[0078] In a 500ml four-neck flask, under an atmosphere of nitrogen gas, add 0.01mol 3-bromo-10,10-diphenyl-10H-anthrone, 0.015molA3, dissolve with a mixed solvent (180ml toluene, 90ml ethanol), and then Add 0.03mol Na 2 CO 3 aqueous solution (2M), then add 0.0001mol Pd (PPh 3 ) 4 , heated to reflux for 10-24 hours, sampled and plated, the reaction was complete. Naturally cooled, filtered, the filtrate was rotary evaporated, and passed through a silica gel column to obtain the target product with an HPLC purity of 99.50% and a yield of 56.5%.
[0079] HPLC-MS: The molecular weight of the material is 683.32, and the measured molecular weight is 683.42.
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Abstract
The invention discloses a compound taking anthrone as a core and an application of the compound in an OLED device. The compound takes anthrone as a parent core, which is connected with a heterocyclic aromatic group to destroy molecular symmetry, so that molecular crystallinity is destroyed, aggregation effect among the molecules can be avoided, and the compound has good film forming ability. The compound as a luminescent layer material is used on an organic light-emitting diode, the OLED device using the compound has good photoelectric performance, so that the requirement by a panel manufacture enterprise can be satisfied.
Description
technical field [0001] The invention relates to the technical field of semiconductors, in particular to an anthrone-based compound and its application as a light-emitting layer material in an organic light-emitting diode. Background technique [0002] Organic Light Emitting Diodes (OLED: Organic Light Emission Diodes) has become a very popular emerging flat-panel display product at home and abroad. Domain, low operating voltage (3 ~ 10V), thin panel (less than 1mm) and rollable characteristics. OLED is hailed as the star flat panel display product of the 21st century. As the technology becomes more and more mature, it may develop rapidly in the future, and its future is limitless. [0003] The principle of OLED light emission is that by applying an external voltage, holes and electrons are injected from the anode and cathode after overcoming the interface energy barrier, and enter the HOMO energy level of the hole transport layer and the LUMO energy level of the electron t...
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