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Polyaza-spirobifluorene compound and organic optoelectronic device using the same

A compound, azaspiro technology, applied in the field of organic optoelectronics, to achieve the effect of improving efficiency, simplifying structure, and improving luminous efficiency

Pending Publication Date: 2018-12-14
SHANGHAI FUTURE OPTOETECH CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the problem of obtaining high efficiency and long life at the same time has always been the bottleneck and hotspot of OLED research.

Method used

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  • Polyaza-spirobifluorene compound and organic optoelectronic device using the same
  • Polyaza-spirobifluorene compound and organic optoelectronic device using the same
  • Polyaza-spirobifluorene compound and organic optoelectronic device using the same

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Experimental program
Comparison scheme
Effect test

preparation example Construction

[0049] Preparation routes of key intermediate materials

[0050]

[0051] Preparation of M1:

[0052]

[0053] Add 3-bromo-2-(2-chlorophenyl)pyridine (13g) and 130mL anhydrous tetrahydrofuran into a dry three-necked flask, replace with nitrogen and cool down to -78°C with liquid nitrogen, then add 20mL of 2.5M n-butyllithium, keep at -78°C for half an hour, TCL detects that the reaction is complete, then dissolve 10g of chloroazafluorenone in 100ml of tetrahydrofuran, add it to the above three-necked flask, and keep at -78°C After reacting for half an hour, the reaction was detected by TCL, and the temperature was raised to room temperature, then quenched with 10% dilute hydrochloric acid solution, extracted with dichloromethane and then spin-dried to obtain the crude product of fluorenol. The resulting crude product of fluorenol was then directly added to 200ml of CH 3 COOH, and then added 10ml of concentrated sulfuric acid, and reacted overnight under reflux conditio...

Embodiment 1

[0056] Embodiment 1: the synthesis of compound 1-44-1

[0057]

[0058] M1 (1.8g) and 3-phenylphenylboronic acid (5g) were completely dissolved in 120ml tetrahydrofuran in a 250ml round-bottomed flask under a nitrogen atmosphere, then 60ml of 2M aqueous sodium carbonate was added, and then tetrakis-(triphenyl Phosphine)palladium (0.3g), and the mixture was heated and stirred for 12 hours. After cooling to room temperature, the aqueous layer was removed. Add 100 ml of dichloromethane, and wash twice with 30 ml of saturated brine. The dichloromethane layer was dried over anhydrous magnesium sulfate, and concentrated in vacuo. Then dichloromethane:ethyl acetate (20:1~2:1) was used as eluent to purify and separate on a silica gel column to obtain 1-44-1 (yield 82%); MS (ESI): 623.2 ( M+H)

Embodiment 2

[0059] Embodiment 2: the synthesis of compound 1-44-49

[0060] MS (ESI): 933.3 (M+H).

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Abstract

The invention provides a polyaza-spirobifluorene compound and its use in an organic optoelectronic device. The polyaza-spirobifluorene compound has a chemical formula (1). The polyaza-spirobifluorenecompound can be used as an electron transport material, an electron injecting material and a hole blocking material in organic photoelectric devices especially such as organic electroluminescent devices (OLEDs), organic field-effect transistors (OFETs) and organic solar cells. The polyaza-spirobifluorene compound also can be used as a host material or an illuminant material in an OLED. The polyaza-spirobifluorene compound has an adjustable energy level, good compatibility with other functional layer materials, a high glass transition temperature, good thermal and light stability and a tripletenergy level meeting exciton binding requirements, improves the efficiency of the organic electroluminescent devices (OLEDs), reduces the operating voltage of OLED, prolongs the service life of OLED and has a good application prospect.

Description

technical field [0001] The invention belongs to the field of organic photoelectric technology, in particular to a polyazaspirobifluorene compound and an organic photoelectric device containing the compound. Background technique [0002] Among organic optoelectronic devices, especially organic electroluminescent devices (OLEDs), organic field effect transistors (OFETs), and organic solar cells (OPVs), many scientists and industries have been researched. Among them, OLED or diode, as a new generation of flat-panel display technology, has gradually entered people's field of vision. Its wide application prospects and rapid technological advancement in recent years have made OLED one of the most popular researches in the field of flat-panel information display and scientific research product development. [0003] The research on organic electroluminescent materials began in the 1960s. Until 1987, Tang et al. made organic electroluminescent devices for the first time, and organic ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D471/10C07D519/00C07F9/6561C09K11/06H01L51/50H01L51/54
CPCC09K11/06C07D471/10C07D519/00C07F9/6561C09K2211/1029C09K2211/1037C09K2211/1044C09K2211/1033C09K2211/1059C09K2211/1088C09K2211/1092H10K85/622H10K85/615H10K85/626H10K85/6576H10K85/657H10K85/6574H10K85/6572H10K50/11Y02E10/549
Inventor 王子兴
Owner SHANGHAI FUTURE OPTOETECH CO LTD
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