Compound taking pyridine as core and application thereof to organic electroluminescence device

A compound, azabenzene technology, applied in the direction of electrical solid-state devices, electrical components, luminescent materials, etc., can solve the problems of efficiency roll-off, low S1 state radiation transition rate, difficult exciton utilization rate and high fluorescence radiation efficiency, etc. Achieve the effects of reducing difficulty and cost, good film formation and fluorescence quantum efficiency, and avoiding aggregation

Active Publication Date: 2018-06-12
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 taking pyridine as core and application thereof to organic electroluminescence device
  • Compound taking pyridine as core and application thereof to organic electroluminescence device
  • Compound taking pyridine as core and application thereof to organic electroluminescence device

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0072] The synthesis of embodiment 1 compound 2

[0073]

[0074] The concrete synthetic route of this compound is provided now:

[0075]

[0076] In a 250ml four-neck flask, under a nitrogen atmosphere, add 0.01mol 4-(4-bromophenyl)-2,6-diphenyl-pyrimidine, 0.015mol (9,9-dimethyl-9H- Fluoren-2-yl)-(6-methyl-9H-carbazol-3-yl)-phenyl-amine, 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 rotary evaporated under reduced pressure (-0.09MPa, 85°C), After passing through a neutral silica gel column, the target product was obtained with a purity of 99.20% and a yield of 59.20%.

[0077] HPLC-MS: The theoretical value is 786.37, and the measured value is 786.42.

Embodiment 2

[0078] The synthesis of embodiment 2 compound 4

[0079]

[0080] The concrete synthetic route of this compound is provided now:

[0081]

[0082] In a 250ml four-neck flask, under a nitrogen atmosphere, add 0.01mol 4-(4-bromophenyl)-2,6-diphenyl-pyrimidine, 0.015mol (9,9-dimethyl-9H- Fluoren-2-yl)-(6-cyclohexyl-9H-carbazol-3-yl)-phenyl-amine, 0.03mol sodium tert-butoxide, 1×10 -4 mol Pd 2 (dba) 3 , 1×10 -4mol 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 98.89% and a yield of 48.50%.

[0083] HPLC-MS: The theoretical value is 854.43, and the measured value is 854.56.

Embodiment 3

[0084] The synthesis of embodiment 3 compound 21

[0085]

[0086] The concrete synthetic route of this compound is provided now:

[0087]

[0088] In a 250ml four-necked flask, add 0.01mol 4-(4-bromophenyl)-2,6-bis-(4-methyl-phenyl)-pyridine, 0.015molN-(9, 9-Dimethyl-9H-fluoren-2-yl)-N,N',N'-triphenyl-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 99.50% and a yield of 58.50%.

[0089] HPLC-MS: The theoretical value is 950.43, and the measured value is 950.52.

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PUM

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Abstract

The invention discloses a compound taking pyridine as a core and application thereof to an organic electroluminescence device. The compound takes pyridine as the core, and has the characteristics thatmolecules are not likely to crystallize and aggregate, and the compound has an excellent film-forming property. When the compound is used as a luminescent layer material of the organic electroluminescence device, the current efficiency, the power efficiency and the external quantum efficiency of the device are greatly improved; and the service life of the device is remarkably prolonged.

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 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...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D403/10C07D401/10C07D405/14C07D413/14C07D401/14C07D403/14C07D409/14C09K11/06H01L51/50H01L51/54
CPCC09K11/06C07D401/10C07D401/14C07D403/10C07D403/14C07D405/14C07D409/14C07D413/14C09K2211/1088C09K2211/1092C09K2211/1059C09K2211/1044C09K2211/1029H10K85/615H10K85/636H10K85/633H10K85/654H10K85/657H10K85/6572H10K85/6574H10K85/6576H10K50/12
Inventor 徐凯李崇张小庆张兆超
Owner JIANGSU SUNERA TECH CO LTD
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