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Compounds containing quinoxaline and biphenyl groups and their organic electroluminescent devices
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A biphenyl group and compound technology, applied in the field of organic electroluminescent compounds and organic electroluminescent devices, can solve the problems of low electron mobility, affecting device life and efficiency, low electron mobility, etc., and achieve high life , good thermal stability, high luminous purity effect
Active Publication Date: 2019-01-15
SHANGHIA TAOE CHEM TECH CO LTD
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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.
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Embodiment 1
[0041] Synthesis of Compound 3
[0042]
[0043] Synthesis of Intermediate 3-1
[0044] In a three-necked flask, add p-chlorophenylboronic acid (2g, 12.8mmol), 2-(4-bromophenyl)-4,6-diphenyl-1,3,5-triazine (5g, 12.8mmol), Potassium carbonate (3.5g, 25.6mmol), tetrakistriphenylphosphine palladium (0.2g), tetrahydrofuran (50ml) and water (15ml), heated to reflux for 10 hours under nitrogen protection, cooled, concentrated, filtered, and the crude product was washed with tetrahydrofuran Recrystallization from ethanol gave a yield of 4.9 g, a yield of 91%.
[0045] Synthesis of Compound 3
[0046] In a three-necked flask, add intermediate 3-1 (3g, 7.2mmol), 2,3-diphenyl-6-(4,4,5,5-tetramethyl-1,3,2-dioxy -boryl)-quinoxaline (2.9g, 7.2mmol), potassium carbonate (2g, 15mmol), palladium acetate (0.2g), X-phos (0.4g), tetrahydrofuran (50ml) and water (15ml), in Heated to reflux for 10 hours under the protection of nitrogen, cooled, concentrated, filtered, and the crude product ...
Embodiment 2
[0048] Synthesis of compound 5
[0049]
[0050] Intermediate 5-1
[0051] The synthesis method is the same as that of intermediate 3-1, the raw materials used are 3-chloro-phenylboronic acid and 4-(4-bromophenyl)-2,6-diphenylpyrimidine, and the yield is 87%.
[0052] Synthesis of compound 5
[0053] The synthesis method is the same as that of compound 3, using intermediate 5-1 instead of intermediate 3-1, and the yield is 71%. Mass Spectrum 664.71.
Embodiment 3
[0055] Synthesis of Compound 12
[0056]
[0057] Synthesis of intermediate 12-1
[0058] The synthesis method is the same as that of intermediate 3-1, the raw materials used are 3-chloro-phenylboronic acid and 4-(3-bromophenyl)-2,6-diphenyl-1,3,5-triazine, and the yield is 93 %.
[0059] Synthesis of Compound 12
[0060] The synthesis method is the same as that of compound 3, except that intermediate 12-1 is used instead of intermediate 3-1, and the yield is 75%. Mass Spectrum 665.49.
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Abstract
The invention provides an organic electroluminescent compound containing quinoxaline and biphenyl group, the compound has good thermal stability, long life and high luminous purity, can be used to make organic electroluminescent devices, and is used in Field of organic solar cells, organic thin film transistors or organic photoreceptors. The present invention also provides an organic electroluminescence device, which comprises an anode, a cathode and an organic layer, the organic layer comprising a light-emitting layer, a hole injection layer, a hole transport layer, a hole blocking layer, an electron injection layer, and an electron transport layer More than one layer of the organic layer, at least one layer of the organic layer contains a compound such as structural formula I.
Description
technical field [0001] The invention relates to the field of organic electroluminescence materials, in particular to an organic electroluminescence compound containing quinoxaline and biphenyl groups and an organic electroluminescence device thereof, belonging to the technical field of display of organic electroluminescence devices. 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 chang...
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Application Information
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