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Pyridine derivative, application thereof and organic electroluminescence device

A technology of pyrimidine derivatives and devices, applied in the field of organic electroluminescent materials, can solve the problems of low electron mobility, affecting device life and efficiency, and low electron mobility, and achieve high luminous purity, good thermal stability, high The effect of luminous efficiency

Inactive Publication Date: 2018-03-23
SHANGHIA TAOE CHEM TECH CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In addition, when the OLED device is operated with an applied voltage, it will generate Joule heat, which makes the organic material easy to crystallize, which affects the life and efficiency of the device. Therefore, it is also necessary to develop stable and efficient organic electroluminescent materials.
[0005] In OLED materials, since most organic electroluminescent materials transport holes faster than electrons, it is easy to cause an imbalance in the number of electrons and holes in the light-emitting layer, so that the efficiency of the device is relatively low.
Tris(8-hydroxyquinoline)aluminum (Alq 3 ) has been widely studied since its invention, but as an electron transport material, its electron mobility is still very low, and it will degrade itself. In the device using it as an electron transport layer, there will be a voltage drop , at the same time, due to the lower electron mobility, a large number of holes enter the Alq 3 In the layer, the excess holes radiate energy in a non-luminescent form, and when used as an electron-transporting material, its application is limited due to its green-emitting properties.

Method used

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  • Pyridine derivative, application thereof and organic electroluminescence device
  • Pyridine derivative, application thereof and organic electroluminescence device
  • Pyridine derivative, application thereof and organic electroluminescence device

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0037] Synthetic route of compound 7

[0038]

[0039] The synthetic method of intermediate 7-1

[0040] In the flask, add 2-iodo-4,4'-dibromobiphenyl (2.5g, 5.8mmol), 3,5-diphenylphenylboronic acid (1.6g, 5.8mmol), potassium carbonate (1.6g, 11.6 mmol), tetrahydrofuran (20mL) and water (10mL), tetrakistriphenylphosphine palladium (0.2g), heated to reflux under nitrogen protection for 10 hours, cooled, extracted with dichloromethane, dried, concentrated, and the crude product was passed through the column Analysis and purification afforded 2 g of product with a yield of 63%.

[0041] The synthetic method of compound 7

[0042] In a flask, add intermediate 7-1 (2 g, 3.7 mmol), pinacol 5-pyrimidineboronate (2.2 g, 11 mmol), potassium carbonate (1 g, 7.4 mmol), tetrahydrofuran (20 mL) and water (10 mL) , tetrakistriphenylphosphine palladium (0.2g), heated to reflux under nitrogen protection for 24 hours, cooled, extracted with dichloromethane, dried, concentrated, and the c...

Embodiment 2

[0044] Synthetic route of compound 8

[0045]

[0046] The synthetic method of intermediate 8-1

[0047] The same as the synthesis method of intermediate 7-1, the boronic acid used was 2-triaceneboronic acid, and the yield was 70%.

[0048] The synthetic method of compound 8

[0049] The synthesis method is the same as that of compound 7, the raw material used is intermediate 8-1, and the yield is 48%.

Embodiment 3

[0051] The synthetic method of compound 13

[0052]

[0053] The synthetic method of intermediate 13-1

[0054] The synthesis method of intermediate 7-1 is the same, the raw material used is 9,9-spirobifluorene-2 ​​boronic acid, and the yield is 65%. The synthetic method of compound 13

[0055] The synthesis method was the same as that of compound 7, the raw material used was intermediate 13-1, and the yield was 44%.

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Abstract

The invention provides a pyridine derivative. The pyridine derivative has a following structure formula (which is as shown in the description). The pyridine derivative provided by the invention has better thermal stability, high luminous efficiency and high luminous purity, and can be applied to the fields of organic electroluminescence devices, organic solar cells, organic thin-film transistors or organic photoreceptors. The invention also provides an organic electroluminescence device. The organic electroluminescence device comprises a positive electrode, a negative electrode and an organiclayer, wherein the organic layer comprises at least one layer of a luminous layer, a hole injection layer, a hole transfer layer, a hole barrier layer, an electron injection layer and an electron transfer layer; at least one layer in the organic layer contains a compound as shown in structural formula I. The organic electroluminescence device manufactured by adopting the pyridine derivative has the advantages of good electroluminescence efficiency, excellent color purity and long service life.

Description

technical field [0001] The invention relates to the field of organic electroluminescent materials, in particular to a pyrimidine derivative and its application, and also relates to an organic electroluminescent device. Background technique [0002] Organic electroluminescent devices (OLEDs) are devices prepared by depositing a layer of organic materials between two metal electrodes by spin coating or vacuum evaporation. A classic three-layer organic electroluminescent device includes a hole transport layer, emissive layer and electron transport layer. The holes generated by the anode are combined with the electrons generated by the cathode through the hole transport layer to form excitons in the light emitting layer through the hole transport layer, and then emit light. Organic electroluminescent devices can be adjusted to emit various required lights by changing the material of the light-emitting layer as required. [0003] As a new type of display technology, organic ele...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D239/26C07D409/14C07D405/14C07D401/14C07D403/14C07D413/14C09K11/06H01L51/50H01L51/54
CPCC09K11/06C07D239/26C07D401/14C07D403/14C07D405/14C07D409/14C07D413/14C09K2211/1029C09K2211/1011C09K2211/1007C09K2211/1059C09K2211/1048C09K2211/1044C09K2211/1092C09K2211/1088H10K85/624H10K85/615H10K85/654H10K85/6576H10K85/6574H10K85/6572H10K50/171H10K50/18H10K50/15H10K50/16H10K50/17H10K2102/00H10K50/11H10K2102/301Y02E10/549
Inventor 黄锦海苏建华
Owner SHANGHIA TAOE CHEM TECH CO LTD