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Organic compounds and application thereof

An organic compound, unsubstituted technology, used in organic chemistry, chemical instruments and methods, luminescent materials, etc., can solve the problems of mismatch between electrons and holes in the luminescent layer, efficiency roll-off, shortened life, etc., and achieve thermodynamic stability and prolongation. Longevity and good protection

Active Publication Date: 2020-02-11
YANTAI XIANHUA CHEM TECH CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The single carrier transport capability will cause a mismatch of electrons and holes in the light-emitting layer, resulting in severe efficiency roll-off and shortened lifetime

Method used

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  • Organic compounds and application thereof
  • Organic compounds and application thereof
  • Organic compounds and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0033] The synthesis of compound A1, the reaction equation is as follows:

[0034]

[0035] The synthesis method is as follows:

[0036] (1) Add 20g (100mmol) of 2,3-dichloroquinoxaline, 60g (110mmol) of 1-dibenzofuran-7-(3-N-phenylcarbazole)boronic acid, tetrakis(triphenylphosphine palladium) 0.9g (0.785mmol, 0.5%), toluene 1500mL, ethanol 1000mL and potassium carbonate 43.3g (314mmol) / water 1000mL, reacted at 80°C for 8h; after the reaction was completed, the reaction was stopped; cooled to room temperature, filtered, and the obtained solid was passed through toluene Purified by medium recrystallization to obtain white powder M1;

[0037] (2) In the reaction flask, add M1 26g (50mmol), phenylboronic acid 22g (110mmol), tetrakis (triphenylphosphine palladium) 0.9g (0.785mmol, 0.5%), toluene 1500mL, ethanol 1000mL and potassium carbonate 43.3g ( 314mmol) / water 1000mL, reacted at 80°C for 8h; after the reaction was completed, the reaction was stopped; cooled to room temper...

Embodiment 2

[0040] The synthesis of compound A6, reaction equation is as follows:

[0041]

[0042] The synthesis method is as follows:

[0043] (1) Add 20g (100mmol) of 2,3-dichloroquinoxaline, 1-dibenzothiophene-boronic acid (110mmol), 0.9g (0.785mmol, 0.5%) of tetrakis(triphenylphosphine palladium), 1500mL of toluene, Ethanol 1000mL and potassium carbonate 43.3g (314mmol) / water 1000mL were reacted at 80°C for 8h; after the reaction was completed, the reaction was stopped; cooled to room temperature, filtered, and the obtained solid was purified by recrystallization from toluene to obtain a white powder M1;

[0044] (2) In the reaction flask, add M126g (50mmol), dibenzocarbazole-N-4-phenylboronic acid (110mmol), tetrakis(triphenylphosphine palladium) 0.9g (0.785mmol, 0.5%), toluene 1500mL, Ethanol 1000mL and potassium carbonate 43.3g (314mmol) / water 1000mL were reacted at 80°C for 8h; after the reaction was completed, the reaction was stopped; cooled to room temperature and filtered...

Embodiment 3

[0047] The synthesis of compound A13, the reaction equation is as follows:

[0048]

[0049] The synthesis method is as follows:

[0050] (1) Add 20g (100mmol) of 2,3-dichloroquinoxaline, 1-dibenzofuran-boronic acid (110mmol), 0.9g (0.785mmol, 0.5%) of tetrakis(triphenylphosphine palladium), 1500mL of toluene, Ethanol 1000mL and potassium carbonate 43.3g (314mmol) / water 1000mL, reacted at 80°C for 8h; after the reaction was completed, the reaction was stopped; cooled to room temperature, filtered, and the obtained solid was purified by recrystallization from toluene to obtain a white powder M1;

[0051] (2) Add intermediate M1 (100mmol), 7H-benzo[4,5]thiophene[2,3-b]carbazole (110mmol), DMF (500mL) and cesium carbonate 43.3g (314mmol), 120°C React for 8 hours; after the reaction is completed, stop the reaction; cool to room temperature, add water, and filter, and the obtained solid is purified by recrystallization from toluene to obtain yellow powder A13.

[0052] 1 H NM...

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Abstract

The invention belongs to the technical field of organic photoelectric materials, and particularly relates to organic compounds and an application thereof. A 1-substituted dibenzoheterocycle structureand an aromatic ring / heteroaromatic ring are connected to the 2,3 positions of quinoxaline. The dibenzoheterocycle structure has a very good electron transmission effect, and quinoxaline is connectedwith the dibenzoheterocycle to realize efficient transmission of charges in molecules, so reduction of the voltage of the material is facilitated, and the light-emitting efficiency is improved. Compared with other connection modes, the 1-substituted dibenzoheterocycle connection mode adopted by the invention has a large steric hindrance, can well protect the active center, is beneficial to the stability of the molecular structure, and prolongs the service life. The compounds are thermodynamically stable, have an excellent material stability, and can be used as a bipolar host material for a light-emitting layer of an organic light-emitting device to achieve the very high light-emitting efficiency and long service life.

Description

technical field [0001] The invention belongs to the technical field of organic photoelectric materials, and in particular relates to a class of organic compounds and applications thereof. Background technique [0002] Organic electroluminescent display (hereinafter referred to as OLED) has a series of advantages such as self-luminescence, low-voltage DC drive, full curing, wide viewing angle, light weight, simple composition and process, etc. Compared with liquid crystal display, organic electroluminescent display is not It needs a backlight source, has a large viewing angle, low power, and its response speed can reach 1000 times that of a liquid crystal display, but its manufacturing cost is lower than that of a liquid crystal display with the same resolution. Therefore, organic electroluminescent devices have broad application prospects. [0003] With the continuous advancement of OLED technology in the two major fields of lighting and display, people pay more attention to...

Claims

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Application Information

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IPC IPC(8): C07D405/14C07D409/14C07D405/04C07D409/04C07D495/04C07D487/04C07D519/00C09K11/06H01L51/54
CPCC07D405/14C07D409/14C07D405/04C07D409/04C07D495/04C07D487/04C07D519/00C09K11/06C09K2211/1029C09K2211/1044C09K2211/1088C09K2211/1092C09K2211/1059C09K2211/1033C09K2211/1037C09K2211/1007H10K85/636H10K85/615H10K85/6576H10K85/6574H10K85/657H10K85/6572Y02E10/549
Inventor 邢其锋丰佩川陈跃胡灵峰陈义丽
Owner YANTAI XIANHUA CHEM TECH CO LTD
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