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

A technology of triphenylpyrimidine and compounds, which is applied in the field of organic electroluminescent materials, can solve the problems of increasing electron injection barriers from the cathode to the light-emitting layer, increasing the device driving voltage, and complicating the device structure, so as to suppress energy transfer and improve Effect of device performance, strong electron transport capability

Active Publication Date: 2015-04-22
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 tri-8-hydroxyquinoline aluminum, because of their lower triplet energy level, usually need to insert a layer of holes 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 triphenylpyrimidine as core as well as preparation method and application thereof
  • Compound using triphenylpyrimidine as core as well as preparation method and application thereof
  • Compound using triphenylpyrimidine as core as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0054] Example 1: Preparation of 2,4,6-tris(4-(3-pyridyl)phenyl)pyrimidine (Tp3PyPM)

[0055] (1) Synthesis of 2,4,6-tris(4-chlorophenyl)pyrimidine

[0056] Under a nitrogen atmosphere, 2,4,6-trichloropyrimidine (3.67g, 20mmol, Aldrich), 4-chlorophenylboronic acid (10.95g, 70mmol, Aldrich), 2M potassium carbonate aqueous solution ( 50ml), bistriphenylphosphine palladium dichloride (0.84g, 1.2mmol, Aldrich) and 1,4-dioxane (120ml, Aldrich), stirred and reacted at 85°C for 8 hours. After the reaction was naturally cooled, the reaction solution was extracted with chloroform, 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 chloroform / n-hexane=2:1. After being spin-dried, vacuum-dried to obtain 5.73 g of white powder with a yield of 69.6%.

[0057] 1 H...

Embodiment 2

[0062] Example 2: Preparation of 2,4,6-tris(3'-(3-pyridyl)di-3-phenyl)-pyrimidine (Tm3PyBPM)

[0063] (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, wi...

Embodiment 3

[0075] Example 3: Preparation of 2,4,6-tris(3-(2-pyrimidinyl)phenyl)pyrimidine (Tm2PmPM)

[0076] (1) Synthesis of 2-(3-chlorophenyl)-pyrimidine

[0077] Under a nitrogen atmosphere, 3-chlorophenylboronic acid (5.00g, 32.0mmol), 2-bromopyrimidine (5.08g, 32.0mmol, Aldrich), tetrakis(triphenylphosphine) palladium (0.740 g, 0.64mmol, Aldrich), 2M potassium carbonate aqueous solution (100ml), toluene (150ml) and ethanol (30ml), stirred and reacted under reflux at 85°C for 18 hours. After the reaction was naturally cooled, the reaction solution was extracted with chloroform, 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=2 / 1. After being spin-dried, vacuum-dried to obtain 5.2 g of white crystals with a yield of 86.3%.

[0078] (...

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Abstract

The invention belongs to the technical field of organic electroluminescence materials, and discloses a compound using triphenylpyrimidine as a core as well as a preparation method and application thereof. The compound can be prepared through SUZUKI coupling reaction of halogenopyrimidine and chlorophenylboronic acid to synthesize tri(chlorophenyl)pyrimidine and SUZUKI coupling reaction of the tri(chlorophenyl)pyrimidine and an azacyclo-borate, or prepared through SUZUKI coupling reaction of azacyclo-borate synthesized through coupling reaction and the like and trichloropyrimidine. The compound using the triphenylpyrimidine as the core consists of a nitrogen heterocyclic unit containing pyridine, pyrimidine and the like with strong electron affinity, and has lower electron injection barrier and stronger electron transmission capability, so that the driving voltage of a device is reduced and the power efficiency of the device is improved; under the brightness of 100cd / m<2>, the driving voltage is 2.71V, the external quantum efficiency reaches 21.6 percent, and the power efficiency reaches 56.71m / W.

Description

technical field [0001] The invention belongs to the technical field of organic electroluminescent materials, and in particular relates to a compound with triphenylpyrimidine as the core and 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 sin...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D401/14C07D239/26C07D403/14C09K11/06H01L51/54
Inventor 苏仕健叶华
Owner SOUTH CHINA UNIV OF TECH
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