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Benzo-five-membered ring-fused heterocyclic organic compound and application thereof

A technology of organic compounds and five-membered rings, applied in the field of organic optoelectronic materials, can solve the problems of mismatch between electrons and holes, shortened lifetime, and efficiency roll-off, and achieve the goals of reducing turn-on voltage, improving lifetime, and good thermal stability Effect

Active Publication Date: 2020-06-19
YANTAI XIANHUA CHEM TECH CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Currently used phosphorescent host materials often have a single carrier transport capability, such as hole transport hosts and electron transport hosts. However, a single carrier transport capability will cause a mismatch between electrons and holes in the light-emitting layer. , resulting in severe efficiency roll-off and shortened life

Method used

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  • Benzo-five-membered ring-fused heterocyclic organic compound and application thereof
  • Benzo-five-membered ring-fused heterocyclic organic compound and application thereof
  • Benzo-five-membered ring-fused heterocyclic organic compound and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0030] For the synthesis of compound A1, the reaction equation is as follows:

[0031]

[0032] The synthesis method is as follows:

[0033] (1) Add 100mmol 3-bromobenzothiophene, 110mmol o-nitrophenylboronic acid, (1%) Pd(PPh 3 ) 4 , Sodium carbonate 40g (300mmol), toluene 800mL, ethanol 200mL and water 200mL, heated to reflux, reacted for 8h, the reaction is complete; the reaction solution is extracted with ethyl acetate, the organic phase is concentrated to obtain a yellow solid M1;

[0034] (2) Add 100mmol of intermediate M1 to 1000mL of o-dichlorobenzene solution, add 300mmol of triphenylphosphine, heat to reflux, react for 12h, the reaction is completed; the solvent is evaporated, silica gel column chromatography is separated, and intermediate M2 is obtained;

[0035] (3) In the reaction flask, take 100mmol of intermediate M2, 2-chloro-4-phenylquinazoline (100mmol), 40g (300mmol) of potassium carbonate and 1000mL of DMF, and react at 120℃ for 12h; stop the reaction after the reac...

Embodiment 2

[0042] For the synthesis of compound A9, the reaction equation is as follows:

[0043]

[0044] The synthesis method is as follows:

[0045] (1) In the reaction flask, add (100mmol) 7-bromobenzothiophene, (110mmol) o-boronic acid methyl benzoate, (1%) Pd(PPh3) 4 , Sodium carbonate 40g (300mmol), toluene (800ml), ethanol (200ml), water (200ml), heated to reflux, reacted for 8h, the reaction is complete. The reaction solution was extracted with ethyl acetate, and the organic phase was concentrated to obtain a yellow solid M1;

[0046] (2) Dissolve 100mmol M1 in 500mL THF, add (220mmol) methylmagnesium bromide at 0°C, control the temperature for 30min, naturally raise the temperature to room temperature, stir and react for 8h, the reaction is complete; add water to the reaction solution, there is solid Precipitate and filter to obtain white solid M2;

[0047] (3) In the reaction flask, add (100mmol) intermediate M2 and 1000mL glacial acetic acid, and react at 120°C for 12h; stop the rea...

Embodiment 3

[0054] For the synthesis of compound A6, the reaction equation is as follows:

[0055]

[0056] The synthesis method is as follows:

[0057] (1) Add 100mmol 3-bromobenzothiophene, 110mmol o-nitrophenylboronic acid, (1%) Pd(PPh 3 ) 4 , Sodium carbonate 40g (300mmol), toluene 800mL, ethanol 200mL and water 200mL, heated to reflux, reacted for 8h, the reaction is complete; the reaction solution is extracted with ethyl acetate, the organic phase is concentrated to obtain a yellow solid M1;

[0058] (2) Add 100mmol of intermediate M1 to 1000mL of o-dichlorobenzene solution, add 300mmol of triphenylphosphine, heat to reflux, react for 12h, the reaction is completed; the solvent is evaporated, silica gel column chromatography is separated, and intermediate M2 is obtained;

[0059] (3) In the reaction flask, take 100mmol of intermediate M2, 2-chloro-4-phenylquinazoline (100mmol), 40g (300mmol) of potassium carbonate and 1000mL of DMF, and react at 120℃ for 12h; stop the reaction after the reac...

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Abstract

The invention belongs to the technical field of organic photoelectric materials, and specifically relates to a benzo-five-membered ring-fused heterocyclic organic compound and an application thereof.The organic compound has a parent structure of benzo-five-membered ring -fused heterocycle, has high bond energy between atoms, has good thermal stability, facilitates intermolecular solid accumulation, and can effectively prolong the service life of a material when being used as a light-emitting layer material. The compound provided by the invention is a derivative of a large conjugated fused heterocycle, is applied to a light emitting layer, has a proper energy level with adjacent levels, facilitates injection of holes and electrons, can effectively reduce turn-on voltage, and can realize good light emitting efficiency in a device due to a high exciton migration rate. The compound disclosed by the invention has large conjugate plane, facilitates molecular accumulation, shows good thermodynamic stability and shows long service life in a device. The preparation process for the derivative provided by the invention is simple and practicable, easily-available in raw materials, and applicable to large-scale production.

Description

Technical field [0001] The invention belongs to the technical field of organic photoelectric materials, and in particular relates to a benzo five-membered ring and fused heterocyclic organic compound and its application. Background technique [0002] Electroluminescence (EL) refers to the phenomenon that luminescent materials are excited by current and electric field to emit light under the action of an electric field. It is a luminescence process that directly converts electrical energy into light energy. Organic electroluminescent display (hereinafter referred to as OLED) has a series of advantages such as autonomous light emission, low-voltage DC drive, full curing, wide viewing angle, light weight, simple composition and process, etc. Compared with liquid crystal displays, organic electroluminescent displays do not It needs a backlight, has a large viewing angle, low power, and its response speed can reach 1,000 times that of a liquid crystal display, but its manufacturing co...

Claims

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Application Information

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IPC IPC(8): C07D471/04C07D487/04C07D495/04C07D495/14C07D498/14C07D513/14C07D519/00C09K11/06H01L51/54H01L51/50
CPCC07D495/14C07D495/04C07D487/04C07D519/00C07D498/14C07D471/04C07D513/14C09K11/06C09K2211/1051C09K2211/1044C09K2211/1037C09K2211/1033C09K2211/1088C09K2211/1059C09K2211/1029C09K2211/1048C09K2211/1007C09K2211/1011H10K85/615H10K85/654H10K85/6574H10K85/657H10K85/6572H10K50/11Y02E10/549
Inventor 邢其锋丰佩川孙伟胡灵峰陈跃陈义丽
Owner YANTAI XIANHUA CHEM TECH CO LTD
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