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Compound and application thereof

A compound and an independent technology, applied in the field of organic electroluminescence, can solve the problems of OLED product efficiency, lifespan, cost, etc., and achieve the effects of enhancing TADF properties, reducing orbital overlap, and low driving voltage

Pending Publication Date: 2021-07-16
BEIJING ETERNAL MATERIAL TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The currently used OLED materials and device structures cannot completely solve the problems of OLED product efficiency, lifespan, cost, etc.

Method used

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  • Compound and application thereof
  • Compound and application thereof
  • Compound and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Synthetic example 1

[0130] Synthesis Example 1: Synthesis of BH22

[0131]

[0132] Synthesis of intermediate BH22-1:

[0133] At room temperature, A (2.18g, 10mmol), B (4.2g, 25mmol), potassium carbonate (4.15g, 30mmol) and N,N-dimethylformamide (DMF, 300mL) were added to a 0.5L single-necked bottle, Nitrogen was replaced and protected, the temperature was raised to 60 degrees Celsius, and the reaction was carried out for 4 hours.

[0134] Stop the reaction, filter while hot, and wash the solid with a large amount of water and ethanol respectively. 3.7 g of a yellow solid was obtained with a yield of 72.6%. Molecular ion mass determined by mass spectrometry: 514.15 (theoretical value: 513.06).

[0135] Synthesis of intermediate BH22-2:

[0136] At room temperature, add D (2.4g, 10.0mmol), E (4.15g, 25.0mmol) and potassium carbonate (4.15g, 30mmol) to a 0.5L three-necked flask, DMF (300mL), nitrogen replacement and protection, and heat up to 60 Celsius, reaction 4h.

[0137] Stop the rea...

Synthetic example 2

[0141] Synthesis Example 2: Synthesis of BH23

[0142]

[0143] Synthesis of intermediate BH23-1:

[0144] At room temperature, add D (2.4g, 10.0mmol), F (5.56g, 25.0mmol) and potassium carbonate (4.15g, 30mmol) to a 0.5L three-necked flask, DMF (300mL), nitrogen replacement and protection, and heat up to 60 Celsius, reaction 4h.

[0145] Stop the reaction, filter while hot, and wash the solid with a large amount of water and ethanol respectively. 3.74 g of a yellow solid was obtained with a yield of 57.9%. Molecular ion mass determined by mass spectrometry: 647.61 (theoretical value: 646.37).

[0146] Synthesis of compound BH23:

[0147] Add BH22-1 (2g, 3.89mmol), BH23-1 (2.77g, 4.28mmol), tetrakistriphenylphosphine palladium (45mg, 39μmol) and sodium carbonate (1.24g, 11.66mmol) to a 500mL three-necked flask and dissolve in 300mL of 1,4-dioxane and 100mL of water were replaced with nitrogen three times and protected, the temperature was raised to 110°C, and the react...

Synthetic example 3

[0149] Synthesis Example 3: Synthesis of BH49

[0150]

[0151] Synthesis of intermediate BH49-1:

[0152] At room temperature, A (2.18g, 10mmol), G (6.99g, 25mmol), potassium carbonate (4.15g, 30mmol) and DMF (300mL) were added to a 0.5L single-necked bottle, replaced with nitrogen and protected, and the temperature was raised to 60 degrees Celsius, Reaction 4h.

[0153] Stop the reaction, filter while hot, and wash the solid with a large amount of water and ethanol respectively. 5.38 g of a yellow solid was obtained, and the yield was 73.0%.

[0154] Synthesis of compound BH49:

[0155] Add BH49-1 (4g, 3.89mmol), BH22-2 (3.19g, 4.28mmol), tetrakistriphenylphosphine palladium (62mg, 39μmol) and sodium carbonate (1.73g, 16.29mmol) to a 500mL three-necked flask and dissolve in 300mL of 1,4-dioxane and 100mL of water were replaced with nitrogen three times and protected, the temperature was raised to 110°C, and the reaction was carried out overnight.

[0156] Silica gel ...

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Abstract

The invention relates to a compound and application thereof, the compound has a structure as shown in a formula I, the compound has thermal activation delay property, adopts a mono-cyano structure to enable blue shift of an emission spectrum, meanwhile, by introducing Dw and Cz groups of a specific structure on a cyano-substituted benzene ring, especially Cz has a double ortho-substitution structure of d1 and d2, finally, the molecular structure is more twisted, HOMO-LUMO track overlapping of molecules is reduced, the TADF property is enhanced, when the compound is applied to an OLED device, the device can have high luminous efficiency, low driving voltage and long service life, and particularly, the effect is better when the compound is used as a luminous layer dye.

Description

technical field [0001] The invention relates to the technical field of organic electroluminescence, in particular to a compound and its application. Background technique [0002] In recent years, optoelectronic devices based on organic materials have become increasingly popular. The inherent flexibility of organic materials makes them very suitable for manufacturing on flexible substrates. They can design and produce beautiful and cool optoelectronic products according to requirements, and obtain incomparable advantages over inorganic materials. Examples of such organic optoelectronic devices include organic light emitting diodes (OLEDs), organic field effect transistors, organic photovoltaic cells, organic sensors, and the like. Among them, OLED is developing rapidly, and has achieved commercial success in the field of information display. OLED can provide high-saturation red, green, and blue colors, and the full-color display device made of it does not need an additional...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D209/86C07D413/14C07D401/14C07D519/00C07F7/10C07D417/10C07D413/10C07D401/10C07D417/14C07D403/14C09K11/06C09B57/00H01L51/50H01L51/54
CPCC07D209/86C07D413/14C07D401/14C07D519/00C07F7/0816C07D417/10C07D413/10C07D401/10C07D417/14C07D403/14C09K11/06C09B57/00C09K2211/1007C09K2211/1029C09K2211/1033C09K2211/1037C09K2211/104C09K2211/1044H10K85/6572H10K85/657H10K50/11
Inventor 李熠烺曲忠国魏金贝李国孟
Owner BEIJING ETERNAL MATERIAL TECH