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Compound taking acridone as core and application of compound to organic electroluminescent device

A compound, the technology of acridone, applied in the application of organic light-emitting diodes, the field of compounds with acridone as the core, can solve the problem of efficiency roll-off, low S1 state radiation transition rate, difficult exciton utilization rate and high fluorescence radiation Efficiency and other issues, to achieve the effect of increasing orbital overlap, good film formation and fluorescence quantum efficiency, and avoiding aggregation

Inactive Publication Date: 2017-08-18
VALIANT CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[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

Method used

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  • Compound taking acridone as core and application of compound to organic electroluminescent device
  • Compound taking acridone as core and application of compound to organic electroluminescent device
  • Compound taking acridone as core and application of compound to organic electroluminescent device

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0046] Synthesis of Example 1 Compound 1

[0047]

[0048] The concrete synthetic route of this compound is provided now:

[0049]

[0050] In a 250ml four-neck flask, under a nitrogen atmosphere, add 0.01mol 2-bromo-9,9-dimethyl-10-phenyl-9,10-dihydro-acridine, 0.025mol acridone, 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 99.56% and a yield of 55.32%.

[0051] HPLC-MS: The molecular weight of the material is 478.20, and the measured molecular weight is 478.39.

Embodiment 2

[0052] Synthesis of Example 2 Compound 2

[0053]

[0054] The concrete synthetic route of this compound is provided now:

[0055]

[0056] In a 250ml four-necked flask, add 0.01mol 10-(4-bromophenyl)-9,9-dimethyl-9,10-dihydro-acridine and 0.025mol acridone under nitrogen atmosphere , 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 point plate, complete reaction, natural cooling, filtration, filtrate rotary evaporation, silica gel column, to obtain the target product with a purity of 99.81% and a yield of 65.20%.

[0057] HPLC-MS: The molecular weight of the material is 478.20, and the measured molecular weight is 478.62.

Embodiment 3

[0058] Synthesis of Example 3 Compound 3

[0059]

[0060] The concrete synthetic route of this compound is provided now:

[0061]

[0062] In a 250ml four-necked flask, add 0.01mol 10-(3-bromophenyl)-9,9-dimethyl-9,10-dihydro-acridine and 0.025mol acridone under nitrogen atmosphere , 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 98.95% and a yield of 78.00%.

[0063] HPLC-MS: The molecular weight of the material is 478.20, and the measured molecular weight is 478.59.

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Abstract

The invention discloses a compound taking acridone as the core and application of the compound to an organic electroluminescent device. The compound takes acridone as the core, and therefore, has the characteristics that the probabilities of crystallization and clustering between molecules are low and the film-forming property is favorable. When the compound serves as a luminescent layer material of the organic electroluminescent device, the current efficiency, the power efficiency and the external quantum efficiency of the organic electroluminescent device are greatly improved; and meanwhile, the service life of the organic electroluminescent device can be remarkably prolonged.

Description

technical field [0001] The invention relates to the technical field of semiconductors, in particular to a compound with acridone as the core and its application as a light-emitting layer material in an organic light-emitting diode. Background technique [0002] Organic electroluminescent (OLED: Organic Light Emission Diodes) device technology can be used to manufacture new display products and also can be used to make new lighting products, which is expected to replace the existing liquid crystal display and fluorescent lighting, and has a wide application prospect. [0003] The OLED light-emitting device is like 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 l...

Claims

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Application Information

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IPC IPC(8): C09K11/06C07D471/04H01L51/54H01L51/50
CPCC09K11/06C07D471/04H10K85/111H10K50/11H10K2102/00H10K2102/301
Inventor 徐凯张兆超王立春
Owner VALIANT CO LTD
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