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Organic electronic material based on phenanthrene and cyanobenzene, and application thereof

A technology of organic electronic materials and benzonitrile, which is applied in luminescent materials, organic chemistry, circuits, etc., can solve the problems of insufficient demand for rapid industrial development, and achieve good thermal stability, lower driving voltage, and high luminous purity.

Active Publication Date: 2020-05-22
SHANGHAI CHUANQIN NEW MATERIAL CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] At present, although a large number of organic electroluminescent materials with excellent performance have been developed one after another, it is still not enough for the rapid development of the entire industry.

Method used

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  • Organic electronic material based on phenanthrene and cyanobenzene, and application thereof
  • Organic electronic material based on phenanthrene and cyanobenzene, and application thereof
  • Organic electronic material based on phenanthrene and cyanobenzene, and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0046] An organic electronic material based on phenanthrene and benzonitrile, the organic electronic material contains compound 2, and the synthetic route of compound 2 is as follows:

[0047]

[0048] The synthetic method of intermediate 2-1

[0049] In the flask, add o-bromoiodobenzene (52.2g, 184.5mmol), phenylacetylene (18.85g, 184.5mmol) and triethylamine (260mL), under nitrogen protection, add cuprous iodide (0.35g, 1.84mmol) and Triphenylphosphinepalladium chloride (0.5g, 0.7mmol), stirred at room temperature for 0.5h, then stopped the reaction, filtered, and concentrated to remove triethylamine to obtain 46.8g of yellow oily liquid, with a yield of 98%.

[0050] The synthetic method of intermediate 2-2

[0051] In the flask, add intermediate 2-1 (13.4g, 52.1mmol), p-chlorophenylboronic acid (8.5g, 54.4mmol) and potassium carbonate (14.4g, 104.2mmol), then add toluene (80mL), tetrahydrofuran (40mL) and deionized water (40mL), under the protection of nitrogen, add t...

Embodiment 2

[0063] An organic electronic material based on phenanthrene and benzonitrile, the organic electronic material contains compound 7, and the synthetic route of compound 7 is as follows:

[0064]

[0065] Synthesis of Intermediate 7-1

[0066] In the flask, under nitrogen protection, add intermediate 2-3 (5g, 12mmol), 3-cyano pinacol borate (4.1g, 17.9mmol), potassium carbonate (5.0g, 36mmol), 30mL toluene, 15 mL of ethanol, 15 mL of deionized water, dichloroditriphenylphosphine palladium (0.15 g), heated to reflux for 3 hours, cooled, separated, washed once with water, and concentrated to dryness. After separation by column chromatography, 3.5 g of white crystalline solid was obtained, with a yield of 74%.

[0067] 1 H NMR (400MHz, CDCl 3 ,δ):8.73-8.78(m,2H),7.63-7.74(m,2H),7.50-7.56(m,3H),7.46(s,1H),7.23-7.41(m,6H),7.07-7.11( m,2H).

[0068] Synthesis of compound 7

[0069] Under the protection of nitrogen, intermediate 7-1 (3g, 7.7mmol), 2,4-diphenyl-6-(3-phenylboroni...

Embodiment 3

[0072] An organic electronic material based on phenanthrene and benzonitrile, the organic electronic material contains compound 8, and the synthetic route of compound 8 is as follows:

[0073]

[0074] The synthesis method of compound 8 is the same as that of compound 2 in Example 1, except that 2,4-diphenyl-6-(3-phenylboronic acid pinacolate)-1,3,5-triazine is used instead of 2 ,4-Diphenyl-6-(4-phenylboronic acid pinacolate)

[0075] Except for -1,3,5-triazine, the yield was 68%.

[0076] 1 H NMR (400MHz, CDCl 3 ,δ):8.96-8.98(m,2H),8.88-8.91(d,1H),8.75-8.78(m,5H),8.11-8.14(m,1H),7.94-7.95(m,1H),7.75 -7.81(m,2H),7.55-7.65(m,10H),

[0077] 7.44-7.46(m,1H),7.21-7.35(m,7H).MS(ESI,m / z):[M+H] + :663.21.

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Abstract

The invention provides an organic electronic material based on phenanthrene and cyanobenzene, and application thereof, belonging to the technical field of organic electroluminescence. According to theinvention, a cyano group, a triazinyl group and other groups are introduced, so the electronegativity of the material is enhanced, the electron transport performance of the material is improved, andthe thermal stability of the material is enhanced. The organic electron transport material provided by the invention is high in luminous efficiency and high in luminous purity. An organic electroluminescent device prepared from the organic electroluminescent compound has the advantages that driving voltage can be reduced, light-emitting efficiency is improved, color purity is excellent, and the service life of the device is prolonged.

Description

Technical field: [0001] The invention relates to the technical field of organic electroluminescence, in particular to an organic electronic material based on phenanthrene and benzonitrile and its application. Background technique: [0002] Organic electroluminescent devices (OLEDs) are a new type of display technology. Each pixel can be switched freely and emits light actively, which makes the display response time short and the color contrast high; the driving voltage can reduce energy consumption; the use of organic materials makes the device more Thin and light, environmentally friendly; and the diversified choices of substrates provide the possibility of flexible and transparent displays, which are widely used in mobile phones, flat panel displays, TVs, lighting and automotive displays. [0003] An organic electroluminescent device is a device prepared by depositing a layer of organic material by spin coating or vacuum evaporation between two metal electrodes, that is, t...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D251/24C07D405/04C09K11/06H01L51/54
CPCC07D251/24C07D405/04C09K11/06C09K2211/1059C09K2211/1011H10K85/626H10K85/615H10K85/654H10K85/6574Y02E10/549
Inventor 苏艳周海涛黄珠菊张景
Owner SHANGHAI CHUANQIN NEW MATERIAL CO LTD
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