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Di-aza-carbazole derivatives and application thereof

A technology of azacarbazole and derivatives, applied in the application field of organic photoelectric materials, can solve the problems of insufficient attention and low luminous efficiency, and achieve the effects of low turn-on voltage, high efficiency and good performance

Inactive Publication Date: 2015-12-02
WUHAN SUNSHINE OPTOELECTRONICS TECH CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, due to its high driving voltage and extremely low luminous efficiency, compared with the booming inorganic material technology, organic electroluminescence has not attracted enough attention.

Method used

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  • Di-aza-carbazole derivatives and application thereof
  • Di-aza-carbazole derivatives and application thereof
  • Di-aza-carbazole derivatives and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0050] Embodiment 1, the preparation of compound 1

[0051]

[0052] Add 2-chloro-3-nitropyridine (10g, 63.25mmol), 3-pyridineboronic acid (6g, 75.5mmol) in a 500ml single-necked flask, and dissolve 100ml of 2M potassium carbonate aqueous solution in 100ml of ethanol, in a solvent of 200ml of toluene . in N 2 Under the protection conditions, adding PdCl 2 (PPh 3 ) 2(1.5 g, 1.95 mmol). The temperature was raised slowly to 100°C, and the mixture was reacted under reflux for 24h. After cooling, the liquid was separated, the organic layer was rotary evaporated, and the column was passed through petroleum ether and ethyl acetate (1.5:1) to obtain 9 g of a light yellow solid with a yield of 70%.

Embodiment 2

[0053] Embodiment 2, the preparation of compound 2

[0054]

[0055] In a single-necked flask of 250ml, add 3-(3-nitropyridin-2-yl)pyridine (8.13g, 40.5mmol) and triphenylphosphine (26.6g, 101.3mmol) solvent in 200ml of o-dichlorobenzene solvent . in N 2 Under the condition of protection, the temperature was raised to 180°C, and the reaction was refluxed for 24h. After the reaction was completed, distill under reduced pressure, concentrate the reaction solvent to 40ml, and pass through the column with dichloromethane and methanol (15:1) to obtain 4g of white solid with a yield of 60%. MS(APCI)m / zcalcdforC 10 h 7 N 3 : 169.18, Found[M + ]:169.7.

Embodiment 3

[0056] Embodiment 3, the preparation of compound 3

[0057]

[0058] Add compound 2 (1g, 6mmol), o-bromoiodobenzene (2g, 7.2mmol), copper powder (1.2g, 18mmol) in a single-necked flask of 250ml, K 2 CO 3 (2.5g, 18mmol) was dissolved in 100ml of dry DMF solvent. in N 2 Under the conditions of protection, the temperature was raised to 150°C, and the reaction was carried out for 48h. After the reaction was terminated, it was cooled to room temperature, extracted, spin-dried, and passed through a column to obtain a light yellow liquid with a yield of 70%. MS(APCI)m / zcalcdforC 16 h 10 BrN 3 : 323.01, Found[M + ]: 324.05.

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Abstract

The invention belongs to the technical field of organic photoelectric material application, and particularly relates to di-aza-carbazole derivatives and application thereof. The derivatives are obtained by bonding di-aza-carbazole serving as a core to different aromatic cyclic compounds. Efficient compounding of current carriers in an organic electroluminescence device can be realized radically by adjusting the bonding amount and the bonding positions of di-aza-carbazole, and adjusting the energy level structure and the current carrier transmission capability of the derivatives, so as to obtain an efficient and energy-saving OLED device.

Description

technical field [0001] The invention belongs to the technical field of application of organic photoelectric materials, and specifically relates to bisazacarbazole derivatives and applications thereof. Background technique [0002] Electroluminescence (EL) refers to a phenomenon in which electrons and holes are injected into organic light-emitting materials under the action of an electric field, and then recombined to emit light. The physical devices produced by this phenomenon are called organic electroluminescent devices. Because such devices are used in display and solid-state lighting technologies, compared with traditional technologies, they have many advantages such as ultra-thin, self-luminous, fast response, high contrast, and flexible devices can be prepared, which has attracted widespread attention worldwide. . [0003] As a new technology with huge market potential, electroluminescence research began in the 1960s, and was first observed in 1936 by Destriau et al....

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F7/10C07D471/14C07D519/00C07D471/04C09K11/06H01L51/54
Inventor 王磊谭江红穆广园
Owner WUHAN SUNSHINE OPTOELECTRONICS TECH CO LTD
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