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Arylamine organic compound and organic electroluminescent device containing same

A technology of organic compounds and aromatic amines, applied in the field of semiconductor materials, can solve problems such as development that has not been fully realized, and achieve the effects of good high and low temperature driving life, ensuring stability, and high hole carrier conduction efficiency.

Active Publication Date: 2021-09-17
JIANGSU SUNERA TECH CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the development of materials for stable and efficient organic material layers for organic electroluminescent devices has not been fully realized

Method used

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  • Arylamine organic compound and organic electroluminescent device containing same
  • Arylamine organic compound and organic electroluminescent device containing same
  • Arylamine organic compound and organic electroluminescent device containing same

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0236] Embodiment 1: the synthesis of intermediate M-1

[0237]

[0238] In a 250ml three-neck flask, under the protection of nitrogen, add 0.01mol raw material A-1, 0.012mol 4-bromochlorobenzene, 150ml toluene and stir to mix, then add 5×10 -5 mol Pd 2 (dba) 3 , 5×10- 5 mol tri-tert-butylphosphine, 0.03mol sodium tert-butoxide, heated to 105°C, refluxed for 24 hours, sampling plate, showed no amino compound remaining, the reaction was complete; naturally cooled to room temperature, filtered, and the filtrate was rotary evaporated to nothing The fraction was passed through a neutral silica gel column to obtain intermediate P-1. LC-MS: found: 280.25 ([M+H]+); exact mass: 279.08.

[0239] Under a nitrogen atmosphere, weigh 0.01 mol of intermediate P-1 and dissolve it in 150 ml of tetrahydrofuran (THF), then add 0.03 mol of bis(pinacol radical) diboron, 1×10 -4 mol(1,1'-bis(diphenylphosphino)ferrocene)dichloropalladium(II) and 0.03mol potassium acetate were added, the mix...

Embodiment 2

[0244] Embodiment 2: the synthesis of compound 1

[0245]

[0246] In a 250ml three-neck flask, under the protection of nitrogen, add 0.01mol raw material C-1, 0.012mol 2-bromo-1-chloro-4-iodobenzene, 150ml toluene and stir to mix, then add 5×10 -5 mol Pd 2 (dba) 3 , 5×10 -5 mol tri-tert-butylphosphine, 0.03mol sodium tert-butoxide, heated to 105°C, refluxed for 24 hours, sampling plate, showed no amino compound remaining, the reaction was complete; naturally cooled to room temperature, filtered, and the filtrate was rotary evaporated to nothing The fraction was passed through a neutral silica gel column to obtain intermediate N-1. LC-MS: Found: 596.31 ([M+H] + ); exact mass: 595.07.

[0247] Under nitrogen atmosphere, add 0.005mol intermediate M-1, 0.006mol intermediate N-1, 5×10 -5 mol Pd(OAc) 2 , 40ml DMF, stirred with nitrogen gas for 30 minutes, then added K 3 PO 4 Aqueous solution (0.0075molK 3 PO 4dissolved in 20ml of water), heated to 130° C., reacted for...

Embodiment 3

[0253] Embodiment 3: the synthesis of compound 104

[0254]

[0255] In a 250ml three-neck flask, under the protection of nitrogen, add 0.01mol raw material A-1, 0.012mol 2-bromo-1-chloro-4-iodobenzene, 150ml toluene and stir to mix, then add 5×10 -5 mol Pd 2 (dba) 3 , 5×10 -5 mol tri-tert-butylphosphine, 0.03mol sodium tert-butoxide, heated to 105°C, refluxed for 24 hours, sampling plate, showed no amino compound remaining, the reaction was complete; naturally cooled to room temperature, filtered, and the filtrate was rotary evaporated to nothing The fraction was passed through a neutral silica gel column to obtain intermediate N-12. LC-MS: Found: 357.87 ([M+H]+); Exact mass: 356.99.

[0256] In a 250ml three-neck flask, under the protection of nitrogen, add 0.01mol raw material E-1, 0.012mol intermediate N-12, 150ml toluene and stir to mix, then add 5×10 -5 mol Pd 2 (dba) 3 , 5×10 -5 mol tri-tert-butylphosphine, 0.03mol sodium tert-butoxide, heated to 105°C, reflu...

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Abstract

The invention relates to the technical field of semiconductor materials, and particularly discloses an arylamine organic compound and an organic electroluminescent device containing the compound. The structure of the compound is shown as a general formula (I). The arylamine organic compound provided by the invention has excellent hole transport capability and stability. When the arylamine organic compound is used for forming a hole transport material of the organic electroluminescent device, the performance of the device can be improved, for example, the efficiency of the device is improved, the driving voltage is reduced, and the service life is prolonged.

Description

technical field [0001] The invention relates to the technical field of semiconductor materials, in particular to an aromatic amine organic compound and an organic electroluminescent device containing the compound. Background technique [0002] The carriers (holes and electrons) in the organic electroluminescent device (OLED) are respectively injected into the device by the two electrodes of the device under the drive of the electric field, and meet in the organic light-emitting layer to recombine and emit light. High-performance organic electroluminescent devices require various organic functional materials to have good photoelectric properties. For example, as a charge transport material, good carrier mobility is required. The injection and transport characteristics of hole injection layer materials and hole transport layer materials used in existing organic electroluminescent devices are relatively weak, and the hole injection and transport rates do not match the electron...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C211/61C07C211/54C07D317/58C07D317/66C07D307/81C07D307/82C07D307/52C07D209/86H01L51/50H01L51/54
CPCC07C211/61C07C211/54C07D317/58C07D317/66C07D307/81C07D307/82C07D307/52C07D209/86C07C2603/18C07C2603/94H10K85/624H10K85/636H10K85/633H10K85/653H10K85/615H10K85/631H10K85/6574H10K85/6572H10K50/15H10K50/156H10K50/17Y02E10/549
Inventor 王芳李崇
Owner JIANGSU SUNERA TECH CO LTD
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