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Thieno thiophene fused heterocyclic organic compound and application thereof

An organic compound, dithiophene technology, which is applied in the field of dithiophene condensed heterocyclic organic compounds, can solve the problems of electron and hole mismatch, efficiency roll-off, and shortened life, so as to reduce the turn-on voltage and improve The effect of life, good thermal stability

Pending Publication Date: 2020-07-17
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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  • Thieno thiophene fused heterocyclic organic compound and application thereof
  • Thieno thiophene fused heterocyclic organic compound and application thereof
  • Thieno thiophene fused heterocyclic organic compound and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0025] The synthesis of compound A1, the reaction equation is as follows:

[0026]

[0027] The synthesis method is as follows:

[0028] (1) Dissolve 100mmol of dithiophene in 500mL of dichloromethane, add to the reaction flask, add NBS in batches to a total of 200mmol, stir at room temperature, react for 8h, and the reaction is complete; add water to the reaction solution, solids are precipitated, filter to obtain a white solid M1;

[0029] (2) Add 100mmol M1, 220mmol 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, and the reaction was completed; the reaction solution was extracted with ethyl acetate, and the organic phase was concentrated to obtain yellow solid M2;

[0030] (3) In the reaction flask, take 100mmol intermediate M2 and add it to 1000mL o-dichlorobenzene solution, then add 300mmol triphenylphosphine, heat to reflux, react for 12h, and the reaction...

Embodiment 2

[0034] The synthesis of compound A7, reaction equation is as follows:

[0035]

[0036] The synthesis method is as follows:

[0037] (1) Dissolve 100mmol of dithiophene in 500mL of dichloromethane, add to the reaction flask, add NBS in batches to 100mmol at 0°C, stir at room temperature, react for 8h, and the reaction is complete; add water to the reaction solution, solids precipitate out, filter , to obtain white solid M1;

[0038] (2) Add M1 (100mmol), o-nitrophenylboronic acid (110mmol), (1%) Pd(PPh 3 ) 4 , sodium carbonate 40g (300mmol), toluene 800mL, ethanol 200mL and water 200mL, heated to reflux, reacted for 8h, and the reaction was completed; the reaction solution was extracted with ethyl acetate, and the organic phase was concentrated to obtain yellow solid M2;

[0039] (3) Take 100mmol of intermediate M2 and add it to 1000mL o-dichlorobenzene solution, add (300mmol) triphenylphosphine, heat to reflux, react for 12h, and the reaction is complete; evaporate the so...

Embodiment 3

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

[0048]

[0049] The synthesis method is as follows:

[0050] (1) Dissolve 100mmol of dithiophene in 500mL of dichloromethane, add to the reaction flask, add NBS in batches to 100mmol at 0°C, stir at room temperature, react for 8h, and the reaction is complete; add water to the reaction solution, solids precipitate out, filter , to obtain white solid M1;

[0051] (2) Add M1 (100mmol), o-nitrophenylboronic acid (110mmol), (1%) Pd(PPh 3 ) 4 , sodium carbonate 40g (300mmol), toluene 800mL, ethanol 200mL and water 200mL, heated to reflux, reacted for 8h, and the reaction was completed; the reaction solution was extracted with ethyl acetate, and the organic phase was concentrated to obtain yellow solid M2;

[0052] (3) Take 100mmol of intermediate M2 and add it to 1000mL o-dichlorobenzene solution, add (300mmol) triphenylphosphine, heat to reflux, react for 12h, and the reaction is complete; evaporate...

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Abstract

The invention belongs to the technical field of organic photoelectric materials, and particularly relates to a thieno thiophene fused heterocyclic organic compound and application thereof. The organiccompound provided by the invention has a thieno thiophene fused heterocyclic parent structure, has high bond energy between atoms, has good thermal stability, is beneficial to intermolecular solid accumulation, and can effectively prolong material service life when being used as a luminescent 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, is beneficial to injection of holes and electrons, can effectively reduce turn-on voltage, and can realizegood light emitting efficiency in a device due to a relatively high exciton migration rate. The compound disclosed by the invention has a relatively large conjugate plane, is beneficial to molecular accumulation, shows good thermodynamic stability and shows long service life in a device. The preparation process of the derivative is simple and feasible, raw materials are easy to obtain, and the derivative is suitable for large-scale production.

Description

technical field [0001] The invention belongs to the technical field of organic photoelectric materials, in particular to a dithieno condensed heterocyclic organic compound and its application. Background technique [0002] Electroluminescence (EL) refers to the phenomenon that luminescent materials are excited by electric current and electric field to emit light under the action of 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 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 requires a backlight source, has a large viewing angle and low power, and its response speed can reach 1000 times that of a liquid crystal display, but its manufacturing cost is lower tha...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D495/22C07D495/14C09K11/06H01L51/50H01L51/54
CPCC07D495/22C07D495/14C09K11/06C09K2211/1051C09K2211/1037C09K2211/1044C09K2211/1059C09K2211/1029H10K85/615H10K85/654H10K85/657H10K85/6572H10K50/12
Inventor 邢其锋丰佩川单鸿斌胡灵峰陈跃陈义丽
Owner YANTAI XIANHUA CHEM TECH CO LTD
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