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A compound with azabenzene as the core and an organic electroluminescent device

An electroluminescent device, azabenzene technology, applied in the field of semiconductors, can solve the problems of low S1 state radiation transition rate, difficult exciton utilization rate, high fluorescence radiation efficiency, efficiency roll-off, etc., to achieve good film-forming properties Effects of fluorescence quantum efficiency, avoidance of aggregation, and mitigation of efficiency roll-off

Active Publication Date: 2021-03-02
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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  • A compound with azabenzene as the core and an organic electroluminescent device
  • A compound with azabenzene as the core and an organic electroluminescent device
  • A compound with azabenzene as the core and an organic electroluminescent device

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0096] The synthesis of embodiment 1 compound 1

[0097]

[0098] The concrete synthetic route of this compound is provided now:

[0099]

[0100] In a 250ml four-neck flask, under a nitrogen atmosphere, add 0.01mol 4-(4-bromophenyl)-2,6-bis-(4-tert-butylphenyl)-pyrimidine, 0.015molN,N, N',N'-Tetra-p-benzyl-9H-carbazole-3,6-diamine, 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, showing no bromide remaining, the reaction was complete; naturally cooled to room temperature, filtered, and the filtrate was subjected to vacuum rotary evaporation (-0.09MPa, 85°C), After passing through a neutral silica gel column, the target product was obtained with a purity of 99.80% and a yield of 62.20%.

[0101]HPLC-MS: The theoretical value is 975.52, and the measured value is 975.68.

Embodiment 2

[0102] The synthesis of embodiment 2 compound 5

[0103]

[0104] The concrete synthetic route of this compound is provided now:

[0105]

[0106] In a 250ml four-neck flask, add 0.01mol 4-(3-bromophenyl)-2,6-bis(4-tert-butylphenyl)-pyridine, 0.015molN,N,N ',N'-Tetra-p-benzyl-9H-carbazole-3,6-diamine, 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, showing no bromide remaining, the reaction was complete; naturally cooled to room temperature, filtered, and the filtrate was subjected to vacuum rotary evaporation (-0.09MPa, 85°C), After passing through a neutral silica gel column, the target product was obtained with a purity of 95.76% and a yield of 58.00%.

[0107] HPLC-MS: The theoretical value is 974.53, and the measured value is 974.65.

Embodiment 3

[0108] The synthesis of embodiment 3 compound 8

[0109]

[0110] The concrete synthetic route of this compound is provided now:

[0111]

[0112] In a 250ml four-neck flask, under a nitrogen atmosphere, add 0.01mol 4-(4-bromophenyl)-2-dibenzofuran-4-yl-6-phenyl-pyridine, 0.015molN,N,N ',N'-Tetra-p-benzyl-9H-carbazole-3,6-diamine, 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, showing no bromide remaining, the reaction was complete; naturally cooled to room temperature, filtered, and the filtrate was subjected to vacuum rotary evaporation (-0.09MPa, 85°C), After passing through a neutral silica gel column, the target product was obtained with a purity of 98.63% and a yield of 82.80%.

[0113] HPLC-MS: The theoretical value is 952.41, and the measured value is 952.52.

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Abstract

The present invention relates to a compound with azabenzene as the core and its application in organic electroluminescent devices. The compound takes azabenzene as the core and has the characteristics of difficult crystallization and aggregation between molecules and good film-forming properties. . When the compound of the present invention is used as a light-emitting layer material of an organic electroluminescent device, the current efficiency, power efficiency and external quantum efficiency of the device are all greatly improved; meanwhile, the life of the device is significantly improved.

Description

technical field [0001] The invention relates to the technical field of semiconductors, in particular to a compound with azabenzene as the core and its application as a light-emitting layer material in an organic light-emitting diode. Background technique [0002] Organic electroluminescence (OLED: Organic Light Emission Diodes) device technology can be used to manufacture new display products and new lighting products, and it 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 light-emitting device,...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D403/10C07D401/10C07D405/14C07D409/14C07D471/04C07D471/14C09K11/06H01L51/54
CPCC09K11/06C07D401/10C07D403/10C07D405/14C07D409/14C07D471/04C07D471/14C09K2211/1088C09K2211/1092C09K2211/1044C09K2211/1029H10K85/6576H10K85/6574H10K85/6572
Inventor 徐凯李崇张小庆张兆超
Owner JIANGSU SUNERA TECH CO LTD
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