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Electroluminescent compound and preparation method and application thereof

A technology of luminescence and compounds, which is applied in the field of electroluminescence compounds and their preparation, can solve the problems of low transmission efficiency and poor stability, and achieve the effects of improving luminescence performance, high stability, and reducing driving voltage

Active Publication Date: 2021-12-03
EVERDISPLAY OPTRONICS (SHANGHAI) CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0009] However, there are few types of electron transport materials currently used in organic electroluminescent devices, and there are still problems of poor stability and low transport efficiency.

Method used

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  • Electroluminescent compound and preparation method and application thereof
  • Electroluminescent compound and preparation method and application thereof
  • Electroluminescent compound and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0072] This embodiment provides an electroluminescent compound with the following structure:

[0073]

[0074] The preparation method of compound 1 is as follows:

[0075]

[0076] Mix 3g of compound 1a, 6g of anhydrous potassium phosphate powder and 100mL of anhydrous 1,4-dioxane, and feed nitrogen gas while vacuuming, so that the reaction is in a nitrogen atmosphere, and add 0.3g of catalyst four ( Triphenylphosphine) palladium Pd (PPh 3 ) 4 and 2.5 g of 2,4-diphenyltriazineboronic acid, stirred and refluxed for 36 h, and the reaction was detected by thin-layer chromatography to be almost complete, and then by column chromatography, 2.1 g of the target product was obtained (yield 46%).

[0077] Characterization results of compound 1: the melting point T of compound 1 was measured by thermogravimetric analysis (TGA) m It is 320°C, and its purity is 99.9% as measured by high performance liquid chromatography (HPLC);

[0078] 1 H NMR (400MHz, DMSO): δ8.99(d,1H),8.41(...

Embodiment 2

[0080] This embodiment provides an electroluminescent compound with the following structure:

[0081]

[0082] The preparation method of compound 2 is as follows:

[0083]

[0084] Mix 2.82g of compound 2a, 6g of anhydrous potassium phosphate powder and 100mL of anhydrous 1,4-dioxane, and pass nitrogen gas while vacuuming, so that the reaction is in a nitrogen atmosphere, and add 0.28g of catalyst IV at 100°C. (Triphenylphosphine)palladiumPd(PPh 3 ) 4 and 2.91 g of compound 2b, stirred and refluxed for 36 h, and the reaction was detected by thin layer chromatography to be almost complete, and then by column chromatography, 2.9 g of the target product was obtained (yield 47%).

[0085] Characterization results of compound 2: The melting point T of compound 2 was measured by TGA m It is 340°C, and its purity measured by HPLC is 99.9%;

[0086] 1 H NMR (400MHz, DMSO): δ8.99(d,1H),8.81(s,1H),8.55(d,1H),8.41(d,1H),8.05(d,2H),7.91(d,1H ),7.87(d,1H),7.60(m,1H),7.57(d,2H),...

Embodiment 3

[0088] This embodiment provides an electroluminescent compound with the following structure:

[0089]

[0090] The preparation method of compound 3 is as follows:

[0091]

[0092] Mix 3g of compound 3a, 6g of anhydrous potassium phosphate powder and 100mL of anhydrous 1,4-dioxane, and feed nitrogen gas while vacuuming, so that the reaction is in a nitrogen atmosphere, and add 0.3g of catalyst four ( Triphenylphosphine) palladium Pd (PPh 3 ) 4 and 2.91 g of 2,4-diphenyltriazineboronic acid, stirred and refluxed for 36 h, and the reaction was detected by thin layer chromatography to be almost complete, and then by column chromatography, 2.3 g of the target product was obtained (yield 45%).

[0093] Characterization results of compound 3: The melting point T of compound 3 was measured by TGA m It is 310°C, and its purity measured by HPLC is 99.9%;

[0094] 1 H NMR (400MHz, DMSO): δ9.52(s,1H),8.59(d,1H),8.06(d,1H),8.05(d,2H),7.77(d,1H),7.61(d,1H ),7.58(d,1H),7.57(d,2H...

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Abstract

The invention provides an electroluminescent compound and a preparation method and application thereof, the electroluminescent compound has a structure as shown in a formula I and is an aza-aryl derivative, the electroluminescent compound is endowed with good electron affinity through combination and synergy of groups, the electroluminescent compound has excellent carrier injection and transmission performance and relatively high stability, and is particularly suitable for being used as an electron transmission material to be applied to OLED devices. The electroluminescent compound is used as the main body material of an electron transport layer, can effectively reduce the driving voltage of the device, improves the luminous efficiency of the device and prolongs the service life of the device.

Description

technical field [0001] The invention belongs to the technical field of organic photoelectric materials, and in particular relates to an electroluminescence compound and its preparation method and application. Background technique [0002] The phenomenon of organic light emission is the process of converting electric current into visible light through the internal process of specific organic molecules. The principle of the organic light-emitting phenomenon is as follows: when an organic material is placed between the negative electrode and the positive electrode, a voltage is applied between the two electrodes, and electrons and holes are injected into the organic material layer from the positive electrode and the negative electrode respectively, and the electrons and holes recombine to form Excitons, which emit light as they transition from an excited state to a ground state. [0003] An organic electroluminescence device is an active light-emitting display device that emit...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D471/04C07D491/048C07D491/147C07D495/14C09K11/06H01L51/54H01L51/50
CPCC07D471/04C07D491/147C07D495/14C07D491/048C09K11/06C09K2211/1044C09K2211/1059C09K2211/1048C09K2211/1029C09K2211/1051C09K2211/1092C09K2211/1077C09K2211/1033H10K85/654H10K85/657H10K85/6574H10K85/6576H10K85/6572H10K50/16Y02E10/549
Inventor 李丹丹
Owner EVERDISPLAY OPTRONICS (SHANGHAI) CO LTD
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