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Organic electroluminescent compound containing cycloheptylnaphthalene, application thereof, and light-emitting device

A cycloheptyl naphthalene and electroluminescence technology, applied in organic chemistry, electro-solid devices, electrical components, etc., can solve the problems of reduced device efficiency, unbalanced charge in the light-emitting layer, difficult electron flow, etc., and achieve good thermal stability. , The effect of high luminous purity and high luminous efficiency

Inactive Publication Date: 2019-05-03
SHANGHIA TAOE CHEM TECH CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, due to the characteristics of CBP that holes are easy to transport and electrons are difficult to flow, the charge in the light-emitting layer is unbalanced, which reduces the efficiency of the device.

Method used

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  • Organic electroluminescent compound containing cycloheptylnaphthalene, application thereof, and light-emitting device
  • Organic electroluminescent compound containing cycloheptylnaphthalene, application thereof, and light-emitting device
  • Organic electroluminescent compound containing cycloheptylnaphthalene, application thereof, and light-emitting device

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0051] Synthetic route of intermediates

[0052]

[0053] Synthetic method of intermediate A

[0054] In a flask, add bromodibenzocycloheptane benzene naphthalene (18 g, 47 mmol), o-nitrophenylboronic acid (8.6 g, 51 mmol), potassium carbonate (13.6 g, 100 mmol), tetrahydrofuran (300 mL), water (150 mL) ), tetrakistriphenylphosphine palladium (1 g), heated back under nitrogen protection for 12 hours, cooled, extracted with dichloromethane, dried, concentrated, and the crude product was purified by column chromatography to obtain 14 g in 75% yield.

[0055] Synthetic method of intermediate B

[0056] In the flask, add intermediate C (20 g, 50 mmol), 100 mL of triethyl phosphite, heat under reflux for 5 hours, cool, remove excess triethyl phosphite under reduced pressure, and the crude product is purified by column chromatography to obtain product 10.8 g, 59% yield. Synthetic method of intermediate C

[0057] The synthesis method was the same as that of intermediate A, an...

Embodiment 2

[0061] Synthetic route of compound 5

[0062]

[0063] Synthetic method of compound 5

[0064] In a flask, add intermediate B (2 g, 5.4 mmol), bromophenanthrene (1.7 g, 5.4 mmol), sodium tert-butoxide (1 g, 10 mmol), palladium acetate (0.1 g), X-phos (0.3 g) , toluene (30 mL), heated to reflux for 15 hours under nitrogen protection, cooled, and the solvent was removed. The crude product was purified by column chromatography to obtain 2.2 g with a yield of 69%.

[0065] The synthesis of other example compounds is the same as the synthesis of compound 5 in Example 1, and the raw material used is the reaction of intermediate B or intermediate D with other halides, as shown in Table 1 below:

[0066] Table 1 Raw materials and yields

[0067]

[0068]

[0069]

[0070]

Embodiment 14

[0072] Synthetic route of compound 29

[0073]

[0074] Synthetic method of compound 29

[0075] In a flask, add Intermediate C (2 g, 5.4 mmol), N,N-dimethylformamide (20 mL), sodium hydride (12 mmol), 2-chloro-4,6-diphenyltriazine (1.45 mmol) in sequence g, 5.4 mmol), stirred for 5 hours, added water, filtered, and recrystallized from toluene to obtain 2.6 g of the product with a yield of 79%.

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Abstract

The invention provides an organic electroluminescent compound containing cycloheptylnaphthalene, which is represented as the structure formula in the specification. The compound has good thermal stability, high luminous efficiency and high luminescence purity, and can be applied to the field of organic electroluminescent devices, organic solar cells, organic thin film transistors or organic photoreceptors, etc. The invention also provides an organic light-emitting device, which includes an anode, a cathode and an organic layer containing at least one of a light-emitting layer, a hole injectionlayer, a hole transport layer, a hole blocking layer, an electron injection layer and an electron transport layer. At least one layer among the organic layers contains the compound as the structure formula I. The organic light-emitting device manufactured from the compound has the advantages of high electroluminescence efficiency, excellent color purity and long life.

Description

technical field [0001] The invention relates to the field of organic electroluminescence materials, in particular to an organic electroluminescence compound containing cycloheptylnaphthalene and uses thereof, and also to an organic electroluminescence device. Background technique [0002] Organic electroluminescent devices (OLEDs) are devices prepared by depositing a layer of organic material between two metal electrodes by spin coating or vacuum evaporation. A classic three-layer organic electroluminescent device contains a hole transport layer, Light emitting layer and electron transport layer. The holes generated by the anode are combined with the electrons generated by the cathode through the electron transport layer to form excitons in the light-emitting layer through the hole transport layer, and then emit light. The organic electroluminescent device can be adjusted to emit various required light by changing the material of the light-emitting layer as required. [00...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D209/94C07D405/04C07D409/04C07D405/10C07D401/04C07D401/10C07D403/04C07D403/10C07D403/14C07D405/14C09K11/06H01L51/50H01L51/54
Inventor 黄锦海苏建华
Owner SHANGHIA TAOE CHEM TECH CO LTD
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