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Organic electroluminescent compound based on pyridine and triazine and organic electroluminescent device thereof

A compound and luminescent technology, applied in organic chemistry, electrical solid devices, electrical components, etc., can solve the problems of low electron mobility, affecting device life and efficiency, low electron mobility, etc., and achieve high luminous purity and good heat The effect of stability and high luminous efficiency

Inactive Publication Date: 2018-02-23
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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  • Organic electroluminescent compound based on pyridine and triazine and organic electroluminescent device thereof
  • Organic electroluminescent compound based on pyridine and triazine and organic electroluminescent device thereof
  • Organic electroluminescent compound based on pyridine and triazine and organic electroluminescent device thereof

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0058] Synthesis of compound 2

[0059]

[0060] In the flask, add intermediate 1-1 (1.8g, 5.7mmol), 2,4-diphenyl-6-[3-(4,4,5,5-tetramethyl-1,3,2- Dioxaborolan-2-yl)phenyl]-1,3,5-triazine (2.5g, 5.7mmol), potassium carbonate (1.6g, 11.5mmol), tetrahydrofuran (20mL), water (10mL ), palladium acetate (0.1g), X-Phos (0.2g), heated to reflux under nitrogen protection for 24 hours, cooled, extracted with dichloromethane, dried, concentrated, and the crude product was purified by column chromatography to obtain 1.8g of the product. rate 55%.

[0061] Prepare the following other compounds with similar synthetic methods, see the following table:

[0062] Table 2

[0063]

[0064]

[0065] Synthesis of Intermediate 2-1

[0066]

[0067] In a flask, add 3-chloro-4-bromo-iodobenzene (5g, 15.9mmol), 1-naphthaleneboronic acid (2.7g, 15.9mmol), potassium carbonate (4.4g, 32mmol), tetrahydrofuran (30mL), water ( 15mL), tetrakistriphenylphosphine palladium (0.3g), heated to r...

Embodiment 9

[0078] Synthesis of compound 27

[0079]

[0080] In a flask, add Intermediate 3-1 (3g, 5.5mmol), 3-pyridineboronic acid pinacol ester (1.3g, 6.6mmol), potassium carbonate (1.5g, 11mmol), dioxane (20mL), Water (10mL), palladium acetate (0.1g), X-Phos (0.2g), under nitrogen protection, heated to reflux for 24 hours, cooled, extracted with dichloromethane, and purified by column chromatography to obtain a yield of 1.6g, product rate 48%.

[0081] Other compounds in Table 5 were prepared by similar synthetic methods:

[0082] table 5

[0083]

[0084]

Embodiment 13-24

[0086] Fabrication of Organic Electroluminescent Devices

[0087] Preparation of OLEDs using compounds of the invention

[0088] First, the transparent conductive ITO glass substrate 110 (with the anode 120 on it) (China CSG Group Co., Ltd.) is washed with deionized water, ethanol, acetone and deionized water in sequence, and then treated with oxygen plasma for 30 seconds.

[0089] Then, NPB was evaporated to form a hole transport layer 130 with a thickness of 60 nm.

[0090] Then, 37.5nm thick Alq was evaporated on the hole transport layer 3 Doped with 1% C545T as the light emitting layer 140 .

[0091] Then, the compound of the present invention was vapor-deposited as an electron transport layer 150 in a thickness of 37.5 nm on the light emitting layer.

[0092] Finally, 1nm LiF was vapor-deposited as the electron injection layer 160 and 100nm Al as the cathode 170 of the device.

[0093] The prepared device (the schematic diagram of the structure is shown in figure 1 )...

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Abstract

The invention provides an organic electroluminescent compound based on pyridine and triazine, which has a structure as shown in the specification. The compound has good thermal stability, high luminous efficiency and high luminous purity, and can be used in the fields of manufacturing organic electroluminescent devices, organic solar cells, organic thin film transistors or organic photoreceptors.The invention further provides an organic electroluminescent device comprising at least one of a light-emitting layer, a hole injection layer, a hole transport layer, a hole blocking layer, an electron injection layer, or an electron transport layer, wherein an organic layer comprises a compound shown by a structural formula I, and the organic electroluminescent device has the advantages of good electroluminescent efficiency, excellent color purity and long service life.

Description

technical field [0001] The invention relates to the field of organic electroluminescence materials, in particular to an organic electroluminescence material based on pyridine and triazine and an organic electroluminescence device thereof, belonging to the technical field of display of organic electroluminescence devices. 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 mate...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D401/10C07D405/14C07D409/14C09K11/06H01L51/50H01L51/54
CPCC09K11/06C07D401/10C09K2211/1029C09K2211/1011C09K2211/1007C09K2211/1092C09K2211/1088C09K2211/1059H10K85/622H10K85/615H10K85/624H10K85/626H10K85/654H10K85/6576H10K85/6574H10K50/16H10K50/171Y02E10/549
Inventor 黄锦海苏建华
Owner SHANGHIA TAOE CHEM TECH CO LTD
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