A compound with azadibenzocycloheptanone as the core and its application in oled

A dibenzocycloheptanone and compound technology, which is applied to the application fields of azadibenzocycloheptanone compounds and organic light-emitting diodes, can solve the problems of disparity, low internal quantum efficiency, and external quantum efficiency lower than 5%. question

Active Publication Date: 2020-05-29
JIANGSU SUNERA TECH CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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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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  • A compound with azadibenzocycloheptanone as the core and its application in oled
  • A compound with azadibenzocycloheptanone as the core and its application in oled
  • A compound with azadibenzocycloheptanone as the core and its application in oled

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0070] The synthesis of embodiment 1 compound 04:

[0071]

[0072] In a 250ml four-neck 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 an atmosphere of nitrogen gas, 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 tri-tert-butylphosphine, 150ml toluene, heating and reflux for 24 hours, sampling point 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 with azadibenzocycloheptanone as the core and its application in organic electroluminescent devices. This type of compound takes azadibenzocycloheptanone as the core, and the material is not easy to crystallize, and has the characteristics of good film formation and thermal stability; at the same time, it has a smaller triplet state than dibenzocycloheptanone. It is different from the singlet state energy, and can make full use of the triplet state energy. When the compound of the present invention is used as a light-emitting layer material of an OLED light-emitting device, the current efficiency, power efficiency and external quantum efficiency of the device are greatly improved; at the same time, the life of the device is significantly improved.

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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Patent Type & Authority Patents(China)
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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