Compound adopting tribenzocycloheptenone as core, and application thereof in OLED devices

A technology of benzocycloheptenone and compound, which is applied in electric solid devices, semiconductor devices, chemical instruments and methods, etc., can solve the problems of limited application and lower triplet energy level, and achieves good optoelectronic performance, high triplet state and the like. state energy levels, the effect of avoiding aggregation

Inactive Publication Date: 2017-07-25
VALIANT CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

At the same time, there is a strong intramolecular charge transfer between the donor and the acceptor of the host material, which leads to the lowering of the triplet energy level of the material itself, which limits its application in industrial production.

Method used

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  • Compound adopting tribenzocycloheptenone as core, and application thereof in OLED devices
  • Compound adopting tribenzocycloheptenone as core, and application thereof in OLED devices
  • Compound adopting tribenzocycloheptenone as core, and application thereof in OLED devices

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0046] Embodiment 1: the synthesis of R structure (shown in general formula 3)

[0047]

[0048] The preparation method of R structure (shown in general formula 3):

[0049] Weigh raw material I o-bromonitro compound, raw material II boric acid, and dissolve it in a mixed solvent of toluene and ethanol with a volume ratio of 2:1, and add potassium carbonate aqueous solution, Pd(PPh 3 ) 4 , reacted at 95-110°C for 10-24 hours, cooled to and filtered the reaction solution, the filtrate was rotary evaporated, and passed through a silica gel column to obtain the target product; the molar ratio of o-bromonitro compound to boric acid was 1:1.0-3.0; o-bromo The molar ratio of nitro compound to potassium carbonate is 1:1.0~3.0; o-bromonitro compound and Pd(PPh 3 ) 4 The molar ratio is 1:0.006~0.02;

[0050] Weigh the product from the previous step, dissolve it with o-dichlorobenzene, and then add PPh 3 , under an inert atmosphere, react the mixed solution of the above reactant...

Embodiment 2

[0057] Embodiment 2: the synthesis of R structure (shown in general formula 2)

[0058]

[0059] The preparation method of Reaction Formula 3-1 is: Weigh the corresponding raw material 1-o-aminophenol, raw material 2-o-nitrophenol, and iodine, stir and dissolve with diethylene glycol as a solvent, and heat to 250-270°C under an inert atmosphere to react 12 ~ 24 hours, take a sample point plate, after the reaction is over, cool naturally to room temperature, solids are precipitated, filter, take the filter cake and pass through a neutral silica gel column to obtain the intermediate En; the mole of the o-nitrophenol and o-aminophenol The ratio is 1:0.8~2.0; the molar ratio of the o-nitrophenol and iodine is 1:0.05~0.1;

[0060] The preparation method of reaction formula 3-2 is: weigh the corresponding bromide and arylamine with methyl formate, then add Pd 2 (dba) 3 , tri-tert-butylphosphine, sodium tert-butoxide; under an inert atmosphere, react the mixed solution of the ab...

Embodiment 3

[0071] Example 3: Synthesis of halogenated compounds of tribenzocycloheptenone

[0072]

[0073]

[0074] Reaction equation 4-1 specific implementation steps:

[0075] Weigh tribenzocycloheptenone and dissolve it in acetic acid, cool down to 0°C with an ice-salt bath; weigh liquid bromine and dissolve it in glacial acetic acid, and slowly add it dropwise to the acetic acid solution containing tribenzocycloheptenone , after the dropwise addition, rise to room temperature, stir the reaction until the reaction is complete; after the reaction, add lye to the reaction solution for neutralization, extract with dichloromethane, separate layers, take the organic phase and filter, and the filtrate is rotary evaporated under reduced pressure to No fraction, through a neutral silica gel column to obtain the intermediate An; the molar ratio of the tribenzocycloheptenone to liquid bromine is 1:0.5~2;

[0076] Reaction equation 4-2 specific implementation steps:

[0077] Weigh the raw...

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Abstract

The invention discloses a compound adopting tribenzocycloheptenone as a core, and an application thereof in OLED devices. The compound adopts the tribenzocycloheptenone as a core, and has the characteristics of difficulty in intermolecular crystallization, difficulty in aggregation, and good film forming ability. When the compound is used as the luminescent layer main body material of the OLED luminescent devices, the current efficiency, the power efficiency and the external quantum efficiency of the devices are greatly improved, and the life of the devices is obviously prolonged.

Description

technical field [0001] The invention relates to the technical field of semiconductors, in particular to a compound of tribenzocycloheptenone and its application as a host material of a light-emitting layer 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 ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D209/86C07D491/153C07D219/02C07D221/20C07D265/38C07D491/048C07D265/34C07D491/16C07D209/94C07D487/04C07D209/88C07D471/04C09K11/06H01L51/54
CPCC07D209/86C07D209/88C07D209/94C07D219/02C07D221/20C07D265/34C07D265/38C07D471/04C07D487/04C07D491/048C07D491/153C07D491/16C09K2211/1029C09K2211/1088C09K2211/1033H10K85/657H10K85/6572
Inventor 高晓祥徐凯李崇张小庆张兆超
Owner VALIANT CO LTD
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