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Compound containing [1,2,4]-triazole [1,5-a] pyridine and organic electroluminescent device thereof

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

Inactive Publication Date: 2017-08-11
SHANGHIA TAOE CHEM TECH CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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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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  • Compound containing [1,2,4]-triazole [1,5-a] pyridine and organic electroluminescent device thereof
  • Compound containing [1,2,4]-triazole [1,5-a] pyridine and organic electroluminescent device thereof
  • Compound containing [1,2,4]-triazole [1,5-a] pyridine and organic electroluminescent device thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0054] Synthesis of Compound 4

[0055]

[0056] Synthesis of Intermediate 4-1

[0057] In the flask, add 2-amino-5-bromopyridine (10g, 58mmol), 4-biphenylboronic acid (11.4g, 58mmol), potassium carbonate (16g, 118mmol), tetrakistriphenylphosphine palladium (0.5g), Tetrahydrofuran (100 mL) and water (50 mL) were heated to reflux for 12 hours under nitrogen protection, cooled, extracted with dichloromethane, dried and concentrated. The crude product was purified by column chromatography to obtain 9 g with a yield of 63%.

[0058] Synthesis of Intermediate 4-2

[0059] In the flask, add 3,5-dibromobenzonitrile (3g, 11.6mmol), 4-(1-naphthyl)-phenylboronic acid (2.9g, 11.6mmol), potassium carbonate (4.1g, 30mmol), four Triphenylphosphine palladium (0.1g), tetrahydrofuran (30mL) and water (15mL), heated to reflux under nitrogen protection for 12 hours, cooled, extracted with dichloromethane, dried, concentrated, and the crude product was purified by column chromatography to ob...

Embodiment 2

[0065] Synthesis of compound 23

[0066]

[0067] Synthesis of intermediate 23-1

[0068] In a single-necked flask, add intermediate 4-1 (3g, 12mmol), 3,5-dibromobenzonitrile (3.1g, 12mmol), cuprous bromide (0.18mmol, 27mg), o-phenanthroline (0.18 mmol, 33mg), zinc iodide (0.37mmol, 118mg), o-dichlorobenzene (30mL), react in air at 150°C for 24 hours, cool to room temperature and dilute with dichloromethane, filter to remove inorganic salts, and use the filtrate after concentration Separated by column chromatography, 3 g of white solid was obtained with a yield of 50%.

[0069] Synthesis of compound 23

[0070] In a flask, add Intermediate 23-1 (2.6g, 5.2mmol), 4-(3-pyridine)-phenylboronic acid (2.6g, 13mmol), potassium carbonate (2.7g, 20mmol), tetrakistriphenylphosphine palladium (0.1g), tetrahydrofuran (20mL) and water (10mL), heated to reflux under nitrogen protection for 12 hours, cooled, extracted with dichloromethane, dried, concentrated, the crude product was pur...

Embodiment 3

[0072] Synthesis of Compound 36

[0073]

[0074] Synthesis of intermediate 36-1

[0075] The synthesis method is the same as that of intermediate 4-1, the raw materials are 2-amino-5-bromopyridine and 3-biphenylboronic acid, and the yield is 61%.

[0076] Synthesis of Intermediate 36-2

[0077] The synthesis method is the same as that of intermediate 23-1, except intermediate 4-1 is replaced by intermediate 36-1, and the yield is 52%.

[0078] Synthesis of Compound 36

[0079] The synthesis method is the same as that of compound 23, the raw materials used are intermediate 36-2 and 5-phenyl-2-pyridine pinacol borate, and the yield is 60%.

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Abstract

The invention provides an organic electroluminescent electron transport compound containing [1,2,4]-triazole [1,5-a] pyridine. The compound has relatively good heat stability, high electroluminescent efficiency and high electroluminescent purity, can be used for preparing an organic electroluminescent device, and is applied to the field of an organic solar cell, an organic thin-film transistor or an organic photoreceptor. The invention further provides an organic electroluminescent device, which comprises an anode, a cathode and an organic layer, wherein the organic layer comprises at least one layer of a electroluminescent layer, a hole injection layer, a hole transport layer, a hole barrier layer, an electron injection layer and an electron transport layer; and the at least one layer of the organic layer contains a compound as shown in a structural formula I. The structural formula I is as shown in the specification.

Description

technical field [0001] The invention relates to the field of organic electroluminescent materials, in particular to a compound containing [1,2,4]-triazol[1,5-a]pyridine and an organic electroluminescent device thereof, which belong to the field of organic electroluminescent device display technology field. 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 li...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D471/04H01L51/54
CPCC07D471/04H10K85/654H10K85/6572Y02E10/549
Inventor 黄锦海苏建华
Owner SHANGHIA TAOE CHEM TECH CO LTD
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