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An organic compound and an organic electroluminescence device containing the same

A technology of organic compounds and compounds, applied in organic chemistry, electrical solid-state devices, luminescent materials, etc., can solve problems such as high driving voltage, low luminous efficiency, low brightness, thermal stability, color purity, and device life

Active Publication Date: 2020-12-29
NANJING TOPTO MATERIALS CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0005] Technical problem to be solved: In view of the fact that there are still many deficiencies in the development of organic electroluminescent devices that need to be improved, the purpose of the present invention is to provide a new type of organic electroluminescent compound to solve the problem of high driving voltage in organic electroluminescent devices. Problems such as low luminous efficiency, brightness, thermal stability, color purity and device life

Method used

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  • An organic compound and an organic electroluminescence device containing the same
  • An organic compound and an organic electroluminescence device containing the same
  • An organic compound and an organic electroluminescence device containing the same

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0079] The synthesis of embodiment 1 compound 1

[0080] (1) Synthesis of Intermediate-1

[0081] [Reaction 1]

[0082]

[0083] Add 23.5g (100mmol, 1.0eq) 2-bromo-3,3'-bipyridine and 235ml THF into a dry 1L three-necked flask under nitrogen protection, and after cooling down to -78°C, add 60ml of n-butyllithium dropwise under stirring (2.5mol / L, 1.0eq), after the dropwise addition was completed, stirred at -78°C for 15min, then added dropwise 26g (100mmol, 1.0eq) (dissolved in 260ml THF) 7-bromo-9-indene[2,1- b] pyridin-9-one, keep stirring at -78°C for 1 hour after the dropwise addition, then naturally warm up to room temperature and stir for 3 hours. After the reaction was detected by TLC, 200ml of water was added to quench the reaction, the reaction solution was extracted twice with 500ml of ethyl acetate to obtain an organic phase, the organic phase was dried with anhydrous magnesium sulfate and passed through a silica gel column to obtain a filtrate, which was spin-...

Embodiment 2

[0102] The synthesis of embodiment 2 compound 26

[0103] (1) Synthesis of Intermediate-5

[0104] [Reaction 6]

[0105]

[0106] Add 23.5g (100mmol, 1.0eq) 2-bromo-3,3'-bipyridine and 235ml THF into a dry 1L three-necked flask under nitrogen protection, and after cooling down to -78°C, add 60ml of n-butyllithium dropwise under stirring (2.5mol / L, 1.0eq), after the dropwise addition, stir at -78°C for 15min, then add dropwise 25.9g (100mmol, 1.0eq) (dissolved in 260ml THF) 2-bromo-9-fluorenone, dropwise After the completion of stirring at -78°C for 1 hour, the temperature was naturally raised to room temperature and stirred for 3 hours. After the reaction was detected by TLC, 200ml of water was added to quench the reaction, the reaction solution was extracted twice with 500ml of ethyl acetate to obtain an organic phase, the organic phase was dried with anhydrous magnesium sulfate and passed through a short column of silica gel to obtain a filtrate, and the filtrate was sp...

Embodiment 3

[0125] The synthesis of embodiment 3 compound 51

[0126] (1) Synthesis of Intermediate-9

[0127] [Equation 11]

[0128]

[0129] Add 23.5g (100mmol, 1.0eq) 2-bromo-3,3'-bipyridine and 235ml THF into a dry 1L three-necked flask under nitrogen protection, and after cooling down to -78°C, add 60ml of n-butyllithium dropwise under stirring (2.5mol / L, 1.0eq), after the dropwise addition was completed, stirred at -78°C for 15min, then added dropwise 26.1g (100mmol, 1.0eq) (dissolved in 260ml THF) 2-bromo-9H-cyclopentene [1 ,2-b: 4'3-b']bispyridin-9-one, after the dropwise addition was completed, keep stirring at -78°C for 1 hour, then naturally warm up to room temperature and stir for 3 hours. After the reaction was detected by TLC, 200ml of water was added to quench the reaction, the reaction solution was extracted twice with 500ml of ethyl acetate to obtain an organic phase, the organic phase was dried with anhydrous magnesium sulfate and passed through a short column of si...

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Abstract

The invention discloses a novel organic compound, and an organic electroluminescent device containing the novel organic compound. The structural formula of the novel organic compound is represented byformula I, wherein X1-X16 are used for representing C or N; R1-R8 are used for representing groups independently selected from hydrogen, heavy hydrogen, F, Cl, Br, I, CN, Si(CH3)3, B(OH)2, substituted or non-substituted C1-C40 straight chain or branched chain alkyl, substituted or non-substituted C1-C40 alkyloxy, substituted or non-substituted C1-C40 thio alkyl, and the like. The novel organic compound can be used in organic electroluminescent devices as HTL, EBL, B-dopant, Host, EIL, ETL, and CPL materials, is capable of reducing driving voltage, increasing luminescence frequency, brightness, heat stability, and color purity, and prolonging device service life.

Description

technical field [0001] The invention belongs to the technical field of luminescent materials, and in particular relates to an organic electroluminescence compound which can be used as a hole transport layer material and an organic electroluminescence device using the compound. Background technique [0002] Organic light-emitting devices (Organic Light-emitting Devices, OLED) are spontaneous light-emitting devices using the following principle: when an electric field is applied, fluorescent substances emit light through the recombination of holes injected from the positive electrode and electrons injected from the negative electrode. This self-luminous device has the characteristics of low voltage, high brightness, wide viewing angle, fast response, good temperature adaptability, etc., and is ultra-thin, and can be fabricated on flexible panels. It is widely used in mobile phones, tablet computers, TVs, lighting, etc. and other fields. [0003] Organic electroluminescent dev...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D471/20C07D471/10C07D471/22C07D405/14C07D405/12C07D401/12C09K11/06H01L51/50H01L51/54
Inventor 许军吕鑫荣
Owner NANJING TOPTO MATERIALS CO LTD
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