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A kind of OLED material containing azacarbazole-o-phenanthroline structure, preparation method and application thereof

A technology of o-phenanthroline and azacarbazole, which is applied in the field of organic electroluminescence, can solve problems such as poor device performance and concentration quenching, and achieve improved power efficiency and external quantum efficiency, low turn-on voltage, and high heat The effect of stability

Active Publication Date: 2018-01-02
VALIANT CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Phosphorescent emitters typically have very long lifetimes and diffusion lengths; however, when emitter concentrations are high, concentration quenching and T1-T1 annihilation are often the main causes of poor device performance

Method used

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  • A kind of OLED material containing azacarbazole-o-phenanthroline structure, preparation method and application thereof
  • A kind of OLED material containing azacarbazole-o-phenanthroline structure, preparation method and application thereof
  • A kind of OLED material containing azacarbazole-o-phenanthroline structure, preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

preparation example Construction

[0037] Preparation of intermediate c

[0038]

[0039] Under nitrogen protection, 5-bromo-1-phenylindole-2,3-dione (intermediate a) (30.2g, 0.1mol) and 1,10-phenanthroline-5,6-diamine (Intermediate b) (21.0 g, 0.1 mol) was put into 200 mL of absolute ethanol. The reaction system was heated to 70-75°C and stirred for 24 hours. After the reaction was completed, after cooling down to room temperature, suction filtration was performed directly, and the filter cake was rinsed with absolute ethanol. The crude product was crystallized with dichloroethane / absolute ethanol to obtain a yellow solid, namely intermediate c, with a yield of 70%.

Embodiment 1

[0040] Embodiment 1 Preparation of host material C01

[0041]

[0042]Under nitrogen protection, the intermediate c (4.76g, 0.01mol) and phenylboronic acid (1.46g, 0.012mol) were added to 100mL of toluene, and then the catalyst tetrakistriphenylphosphine palladium (0.12g, 0.1mmol) and carbonic acid Potassium (4.14g, 0.03mol) aqueous solution. The system was heated to reflux and stirred for 12 hours, then cooled to room temperature naturally, separated, and rotary evaporated to obtain the crude product.

[0043] The crude product was chromatographed on a neutral alumina column, and the eluent was V 二氯甲烷 :V 乙酸乙酯 =1:3 Purification and separation to obtain an off-white powder, which was further sublimated and purified using a chemical vapor deposition system at a sublimation temperature of 340°C to obtain compound C01 with a yield of 60%.

[0044] High resolution mass spectrometry, ESI source, positive ion mode, molecular formula C 32 h 19 N 5 , theoretical value 473.1640...

Embodiment 2

[0045] Embodiment 2 preparation of host material C02

[0046]

[0047] Under nitrogen protection, intermediate c (4.76g, 0.01mol) and 4-biphenylboronic acid (2.38g, 0.012mmol) were added to 100mL of toluene, and then the catalyst tetrakistriphenylphosphine palladium (0.12g, 0.1mmol ) and potassium carbonate (4.14g, 0.03mol) in water. The system was heated to reflux and stirred for 12 hours, then cooled to room temperature naturally, separated, and rotary evaporated to obtain the crude product.

[0048] The crude product was chromatographed on a neutral alumina column, and the eluent was V 二氯甲烷 :V 乙酸乙酯 = 1:3 purification and separation to obtain an off-white powder, which was further sublimated and purified by a chemical vapor deposition system at a sublimation temperature of 360°C to obtain compound C02 with a yield of 63%.

[0049] High resolution mass spectrometry, ESI source, positive ion mode, molecular formula C 38 h 23 N 5 , theoretical value 549.1953, test valu...

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Abstract

The invention discloses an OLED material containing an azacarbazole-o-phenanthroline structure, a preparation method and an application thereof, and belongs to the technical field of organic electroluminescence. It has the following structure: wherein, R1 is an aromatic group without substituents; R2 is an aromatic group with or without substituents. The invention also discloses a preparation method and application of the OLED material. The OLED material of the invention can satisfy high efficiency and high thermal stability at the same time, and the OLED material can be used in an organic electroluminescent device to significantly improve the efficiency of the device.

Description

technical field [0001] The invention relates to an OLED material containing an azacarbazole-o-phenanthroline structure, a preparation method and an application thereof, and belongs to the technical field of organic electroluminescence. Background technique [0002] As a display technology with great application prospect, organic electroluminescent device (OLED) has attracted more and more attention. Due to its inherent characteristics, such as self-illumination, wide viewing angle, fast response speed, flexible display and many other advantages, it has become the most favorable competitor for the next generation of display technology. Since its invention in the 1980s, organic electroluminescent devices have been used in industries, such as cameras, computers, mobile phones, and television monitors. Due to the continuous investment and unremitting efforts of all walks of life over the years, organic electroluminescent Technology has evolved enormously. Nevertheless, many pr...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D471/22C09K11/06H01L51/50H01L51/54
CPCC09K11/06C07D471/22C09K2211/1044C09K2211/1059C09K2211/1007C09K2211/1029C09K2211/1011H10K85/624H10K85/654H10K85/6572H10K50/00
Inventor 张学衡巨成良石宇杨腾迟鹏利杨昊
Owner VALIANT CO LTD
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