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Compound taking aza-dibenzosuberone as core and application thereof on OLED

A technology of dibenzocycloheptanone and compound, which is applied in the fields of organic chemistry, chemical instruments and methods, electrical components, etc., can solve the problems of external quantum efficiency lower than 5%, low internal quantum efficiency, very different and other problems

Active Publication Date: 2017-08-08
JIANGSU SUNERA TECH CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In addition, for the collocation of OLED devices with different structures, the photoelectric functional materials used have strong selectivity, and the performance of the same material in devices with different structures may be completely different.
At present, the research on fluorescent materials has made considerable progress, which can meet the needs of industrialization; traditional organic fluorescent materials can only use 25% singlet excitons formed by electrical excitation to emit light, and the internal quantum efficiency of the device is low (up to 25 %), resulting in external quantum efficiency generally lower than 5%; especially in the blue light lifetime, there are still huge challenges

Method used

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  • Compound taking aza-dibenzosuberone as core and application thereof on OLED
  • Compound taking aza-dibenzosuberone as core and application thereof on OLED
  • Compound taking aza-dibenzosuberone as core and application thereof on OLED

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0070] The synthesis of embodiment 1 compound 04:

[0071]

[0072] In a 250ml four-necked flask, under nitrogen atmosphere, add 0.01mol of 8-bromoazepine dibenzocycloheptanone, 0.012mol of intermediate B1, 0.03mol of 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 98.7% and a yield of 68.7%. HRMS(EI): The calculated value is 490.2045, and the measured value is 490.2065.

Embodiment 2

[0073] The synthesis of embodiment 2 compound 13:

[0074]

[0075] In a 250ml four-neck flask, under a nitrogen atmosphere, add 0.01mol 8-bromoazepine dibenzocycloheptanone, 0.012mol intermediate B2, 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 97.7% and a yield of 68.7%. HRMS(EI): calculated value 539.1998, found value 539.1963.

Embodiment 3

[0076] The synthesis of embodiment 3 compound 19:

[0077]

[0078]In a 250ml four-neck flask, under an atmosphere of nitrogen gas, add 0.01mol 8-bromoazepine dibenzocycloheptanone, 0.012mol intermediate B5, 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 97.7% and a yield of 68.7%. HRMS(EI): calculated value 554.1630, found value 554.1689.

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Abstract

The invention discloses a compound taking aza-dibenzosuberone as a core and application thereof on organic light emission diodes device. The compound takes the aza-dibenzosuberone as the core, the material is hard to crystalize and has good film-forming property, thermal stability and the like; at the same time, the material disclosed by the invention has smaller triplet state and singlet state energy difference compared with the dibenzosuberone, and the triplet state energy can be sufficiently utilized. When the compound disclosed by the invention is used as the luminescent layer material of the OLED device, the current efficiency, the power efficiency and the external quantum efficiency of the device are greatly improved; and meanwhile, the life of the device is obviously prolonged.

Description

technical field [0001] The invention relates to the technical field of semiconductors, in particular to an azadibenzocycloheptanone compound 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. Currently, OLED display technology has been applied in smart phones, tablet computers and other fields, and will further expand to large-size applications such as TVs. However, compared with the actual product application requirements, the luminous efficiency and service life of OLED devices need to be further improved. The OLED light-emitting device is like a sandwich structure, including electrode material fil...

Claims

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Application Information

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IPC IPC(8): C07D221/18C07D401/04C07D401/10C07D401/14C07D413/14C07D471/04C07D487/04C07D491/048C07D491/153C09K11/06H01L51/54
CPCC09K11/06C07D221/18C07D401/04C07D401/10C07D401/14C07D413/14C07D471/04C07D487/04C07D491/048C07D491/153C09K2211/1029C09K2211/1033H10K85/657H10K85/6572
Inventor 张小庆高晓祥徐凯张兆超
Owner JIANGSU SUNERA TECH CO LTD
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