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

A technology of light-emitting devices and compounds, applied in the fields of electrical solid devices, electrical components, light-emitting materials, etc., can solve the problems of efficiency roll-off, difficult exciton utilization rate, high fluorescence radiation efficiency, and low S1 state radiation transition rate, etc. The effect of increasing orbital overlap, good fluorescence quantum efficiency, and good industrialization prospects

Active Publication Date: 2017-03-01
JIANGSU SUNERA TECH 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 with acridone as core and application of compound to organic electroluminescent device
  • Compound with acridone as core and application of compound to organic electroluminescent device
  • Compound with acridone as core and application of compound to organic electroluminescent device

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0039] The synthesis of embodiment 1 compound 2

[0040]

[0041] The concrete synthetic route of this compound is provided now:

[0042]

[0043] In a 250ml four-neck flask, under nitrogen atmosphere, add 0.01mol 3-bromo-9-(3,5-dimethylphenyl)-6-(diphenylamino)carbazole, 0.025mol acridone , 0.03mol sodium tert-butoxide, 1×10 -4 mol Pd 2 (dba) 3 , 1×10 -4 mol tri-tert-butylphosphine, 150ml toluene, heated to reflux for 24 hours, sampled and spotted, 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 a purity of 99.60% and a yield of 57.32%.

[0044] Using DEI-MS to identify the compound, formula C 45 h33 N 3 O, detection value [M+1] + =631.42, calculated value 631.26.

Embodiment 2

[0045] The synthesis of embodiment 2 compound 4

[0046]

[0047] The concrete synthetic route of this compound is provided now:

[0048]

[0049] In a 250ml four-neck flask, under an atmosphere of nitrogen gas, add 0.01mol 3-bromo-9-(3,5-diphenylphenyl)-6-tert-butylcarbazole, 0.025mol acridone, 0.03 mol 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 99.62% and a yield of 62.32%.

[0050] Using DEI-MS to identify the compound, formula C 47 h 36 N 2 O, detection value [M+1] + =644.52, calculated value 644.28.

Embodiment 3

[0051] The synthesis of embodiment 3 compound 7

[0052]

[0053] The concrete synthetic route of this compound is provided now:

[0054]

[0055] In a 250ml four-neck flask, under nitrogen atmosphere, add 0.01mol 3-bromo-9-phenyl-6-acridylcarbazole, 0.025mol acridone, 0.03mol sodium tert-butoxide, 1×10 -4 mol Pd 2 (dba) 3 , 1×10 -4 mol tri-tert-butylphosphine, 150ml 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 99.52% and a yield of 64.42%.

[0056] Using DEI-MS to identify the compound, formula C 46 h 33 N 3 O, detection value [M+1] + =643.58, calculated value 643.26.

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Abstract

The invention discloses a compound with acridone as the core and application of the compound to an organic electroluminescent device. The compound has acridone as the core, is not easy to crystallize between molecules and is not easy to aggregate, and has good film forming ability. When the compound is used as a luminescent layer material of an OLED luminescent device, current efficiency, power efficiency and external quantum efficiency of the device are all greatly improved. Meanwhile, life of the device is obviously 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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Patent Type & Authority Applications(China)
IPC IPC(8): C07D401/04C07D401/14C07D417/14C07D413/14C07D421/14C09K11/06H01L51/54H01L51/50
CPCC09K11/06C07D401/04C07D401/14C07D413/14C07D417/14C07D421/14C09K2211/1029C09K2211/104C09K2211/1037C09K2211/1033H10K85/636H10K85/657H10K85/6572H10K50/11
Inventor 李崇于凯朝张兆超徐凯
Owner JIANGSU SUNERA TECH CO LTD
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