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Compound using tripyridylbenzene as core as well as preparation method and application thereof

A technology of tripyridylbenzene and pyridylbenzene boronate, which is applied in the field of compounds with tripyridylbenzene as a core and the preparation thereof, can solve the problems of increasing injection barriers, increasing device driving voltage, complex device structure and the like, and achieving Effects of low electron injection barrier, reduced driving voltage, and simple device structure

Active Publication Date: 2013-11-20
SOUTH CHINA UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

The commonly used electron transport materials, such as tris(8-hydroxyquinoline)aluminum, because of their lower triplet energy level, usually need to insert a layer of space between the light-emitting layer and the electron transport layer of phosphorescent devices. Hole and exciton blocking layer, which correspondingly increases the electron injection barrier from the cathode to the light-emitting layer, increases the driving voltage of the device, and the device structure is more complex

Method used

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  • Compound using tripyridylbenzene as core as well as preparation method and application thereof
  • Compound using tripyridylbenzene as core as well as preparation method and application thereof
  • Compound using tripyridylbenzene as core as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0056] Embodiment 1: The preparation of the compound taking tripyridylbenzene as nucleus

[0057] (1) Preparation of pyridylbromobenzene: Add 1,3-dibromobenzene (24.8g, 105mmol, Aldrich), 2-pyridylzinc bromide (0.5M in THF, 140mL, 70mmol, Aldrich), tetrakis(triphenylphosphine)palladium (2.43g, 2.1mmol, TCI) and anhydrous tetrahydrofuran (30ml), stirred and reacted at 75°C for 24h. After the reaction was naturally cooled, the reaction solution was extracted with ethyl acetate, washed three times with saturated brine, and the obtained organic layer was dried over anhydrous magnesium sulfate. Filter with suction, and remove the solvent in the resulting filtrate under reduced pressure. Separation with a chromatographic column, the mobile phase used is n-hexane / ethyl acetate=8:1. After spin-dried, vacuum-dried to obtain 10.3 g of a colorless oily product, 3-(2-pyridyl)bromobenzene, with a yield of 63%.

[0058] 1 H NMR (270MHz, CDCl 3 ):δ(ppm)8.83(d,J=2.3Hz,1H),8.63(dd,J=4.8an...

Embodiment 2

[0070] Embodiment 2: The preparation of the compound taking tripyridylbenzene as nucleus

[0071] (1) Preparation of pyridylchlorobenzene: Add 3-bromopyridine (4.84g, 30.6mmol, Aldrich), 3-chlorophenylboronic acid (4.95g, 31.6mmol, Aldrich) into a 250ml three-necked flask under nitrogen atmosphere, Tetrakis(triphenylphosphine)palladium (0.70g, 0.61mmol, TCI), 2M potassium carbonate aqueous solution (90ml), toluene (150ml) and ethanol (50ml), stirred and reacted at 85°C for 24h. After the reaction was naturally cooled, the reaction solution was extracted with toluene, washed three times with saturated brine, and the obtained organic layer was dried over anhydrous magnesium sulfate. Filter with suction, and remove the solvent in the resulting filtrate under reduced pressure. Separation with a chromatographic column, the mobile phase used is n-hexane / ethyl acetate=3:1. After spin-dried, vacuum-dried to obtain 5.3 g of a colorless oily product, 3-(3-pyridyl)chlorobenzene, with a...

Embodiment 3

[0081] Embodiment 3: The preparation of the compound taking tripyridylbenzene as nucleus

[0082] (1) Preparation of pyridylbromobenzene: Add 4-pyridine borate (18.1g, 88.4mmol, Aldrich), 3-iodo-1-bromobenzene (25g, 88.4mmol) into a 250ml three-necked flask under nitrogen atmosphere , Aldrich), tetrakis(triphenylphosphine)palladium (2.04g, 1.77mmol, TCI), 2M potassium carbonate aqueous solution (100ml), toluene (150ml) and ethanol (50ml), stirred and reacted at 85°C for 24h. After the reaction was naturally cooled, the reaction solution was extracted with toluene, washed three times with saturated brine, and the obtained organic layer was dried over anhydrous magnesium sulfate. Filter with suction, and remove the solvent in the resulting filtrate under reduced pressure. Separation with a chromatographic column, the mobile phase used is n-hexane / ethyl acetate=3:1. After being spin-dried, vacuum-dried to obtain 11.1 g of a colorless oily product, 3-(4-pyridyl)bromobenzene, wit...

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Abstract

The invention belongs to the technical field of organic electroluminescence materials, and discloses a compound using tripyridylbenzene as a core as well as a preparation method and application thereof. The compound can be prepared by synthesizing a halogen substituted pyridine derivative and then performing SUZUKI coupling reaction on the halogen substituted pyridine derivative and a triphenyl borate in the presence of a catalyst, or prepared by synthesizing a halogenotripyridylbenzene derivative through SUZUKI coupling reaction and then performing SUZUKI coupling reaction on the halogenotripyridylbenzene derivative and an azacyclo-substituted phenyl borate in the presence of a catalyst. The compound consists of a nitrogen heterocyclic unit containing pyridine and the like with strong electron affinity, and has lower electron injection barrier and stronger electron transmission capability, so as to reduce the driving voltage of a photoelectric device and improve the power efficiency; under the brightness of 100cd / m<2>, the driving voltage of the prepared photoelectric device is 3.03V, the power efficiency is 59.71m / W, and the external quantum efficiency is 25.7 percent.

Description

technical field [0001] The invention belongs to the technical field of organic electroluminescence materials, and in particular relates to a compound with tripyridylbenzene as the core, its preparation method and application. Background technique [0002] In the past two decades, organic light-emitting diodes (OLEDs) have broad application prospects due to their high efficiency, low-voltage drive, easy large-area preparation and full-color display, and have attracted widespread attention. The research began in the 1950s, and until 1987, Dr. Deng Qingyun of Kodak Company of the United States adopted a sandwich device structure in the patent US4356429, and the OLED device developed by the 10V DC voltage drive had a luminous brightness of 1000cd / m 2 , so that OLED has achieved an epoch-making development. [0003] Organic electroluminescence is mainly divided into fluorescence and phosphorescence, but according to the spin quantum statistical theory, the probability of singlet...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D213/06C07D213/127C09K11/06H01L51/54
Inventor 苏仕健陈东成
Owner SOUTH CHINA UNIV OF TECH
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