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Compound containing anthrone and nitrogen-containing heterocyclic rings and application of compound on OLED

A technology of compounds and nitrogen heterocycles, applied in organic chemistry, chemical instruments and methods, photovoltaic power generation, etc., can solve very different problems

Pending Publication Date: 2019-05-14
JIANGSU SUNERA TECH CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In addition, for the collocation of OLED devices with different structures, the photoelectric functional materials used have strong selectivity, and the performance of the same material in devices with different structures may be completely different.

Method used

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  • Compound containing anthrone and nitrogen-containing heterocyclic rings and application of compound on OLED
  • Compound containing anthrone and nitrogen-containing heterocyclic rings and application of compound on OLED
  • Compound containing anthrone and nitrogen-containing heterocyclic rings and application of compound on OLED

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0054] The synthesis of embodiment 1 intermediate M:

[0055]

[0056] (1) Under a nitrogen atmosphere, weigh raw material B and dissolve it in tetrahydrofuran, then add raw material C and tetrakis(triphenylphosphine)palladium, stir the mixture, then add potassium carbonate aqueous solution, and mix the above-mentioned reactants at the reaction temperature At 70-90°C, heat to reflux for 5-20 hours. After the reaction, cooling and adding water, the mixture was extracted with dichloromethane, the extract was dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure, the obtained residue was purified by silica gel column to obtain intermediate I;

[0057] The molar ratio of raw material B to raw material C is 1:1.0~1.5, the molar ratio of tetrakis(triphenylphosphine) palladium to raw material B is 0.001~0.02:1, and the molar ratio of potassium carbonate to raw material B is 1.0~2.0 :1, the ratio of THF dosage to raw material B is 1g:10~30ml.

[00...

Embodiment 2

[0079] The synthesis of embodiment 2 compound 3:

[0080]

[0081] In a 250mL three-necked flask, feed nitrogen, add 0.01mol of raw material A1, 150ml of THF, 0.015mol of intermediate M-1, 0.0001mol of tetrakis(triphenylphosphine) palladium, stir, and then add 0.02mol of K 2 CO 3 Aqueous solution (2M), heated to 80°C, refluxed for 15 hours, sampled and plated, the reaction was complete. Cool naturally, extract with 200ml of dichloromethane, separate layers, dry the extract with anhydrous sodium sulfate, filter, rotate the filtrate, and purify through a silica gel column to obtain the target compound with a HPLC purity of 99.1% and a yield of 77.3%. Elemental analysis structure (molecular formula C 34 h 21 N 3 o 2 ): theoretical value C, 81.10; H, 4.20; N, 8.34; test value: C, 81.10; H, 4.20; N, 8.33. ESI-MS(m / z)(M + ): The theoretical value is 503.16, and the measured value is 503.65.

Embodiment 3

[0082] The synthesis of embodiment 3 compound 10:

[0083]

[0084] In a 250mL three-necked flask, feed nitrogen, add 0.01mol of raw material A1, 150ml of THF, 0.015mol of intermediate M-2, 0.0001mol of tetrakis(triphenylphosphine) palladium, stir, and then add 0.02mol of K 2 CO 3 Aqueous solution (2M), heated to 80°C, refluxed for 15 hours, sampled and plated, the reaction was complete. Cool naturally, extract with 200ml of dichloromethane, separate layers, dry the extract with anhydrous sodium sulfate, filter, rotate the filtrate, and purify through a silica gel column to obtain the target compound with an HPLC purity of 99.3% and a yield of 71.9%. Element analysis structure (molecular formula C 40 h 25 N 3 o 2 ): theoretical value C, 82.88; H, 4.35; N, 7.25; test value: C, 82.88; H, 4.35; N, 7.24. ESI-MS(m / z)(M + ): The theoretical value is 579.19, and the measured value is 579.75.

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Abstract

The invention discloses a compound containing anthrone and nitrogen-containing heterocyclic rings and an application of the compound on OLED. The compound contains anthrone and nitrogen-containing heterocyclic ring structures, two groups are strong electron groups, have deep HOMO energy level and high electron mobility, and are suitable for an application as hole blocking materials or electron transport materials; the compound further can be used as a partial electron type luminescent layer main material; and in addition, the compound has strong group rigidity, and has the characteristics of difficult crystallization and aggregation among molecules and good film forming property. The current efficiency, power efficiency and external quantum efficiency of OLED devices are greatly improved after the compound is applied as an organic electroluminescent functional layer material; and at the same time, the improvement of the device life is very obvious.

Description

technical field [0001] The invention relates to the technical field of semiconductors, in particular to a compound containing anthrone and a nitrogen-containing heterocycle and its application in OLEDs. Background technique [0002] Organic electroluminescent (OLED: Organic Light Emission Diodes) device technology can be used to manufacture new display products and also can be used to make new lighting products, which is expected to replace the existing liquid crystal display and fluorescent lighting, and has a wide application prospect. The OLED light-emitting device is like a sandwich structure, including electrode material film layers, and organic functional materials sandwiched between different electrode film layers. Various functional materials are superimposed on each other according to the application to form an OLED light-emitting device. As a current device, when a voltage is applied to the electrodes at both ends of the OLED light-emitting device, and the positive...

Claims

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Application Information

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IPC IPC(8): C07D405/10C07D405/14C07D251/24C07D471/04C07D413/14C07D401/14C07D213/50C07D239/26C09K11/06H01L51/50H01L51/54
CPCC07D213/50C07D239/26C07D251/24C07D401/14C07D405/10C07D405/14C07D413/14C07D471/04C09K11/06C07D401/04Y02E10/549H10K85/654H10K85/6572H10K85/342H10K50/11H10K2101/10H10K50/16H10K50/18H10K30/353
Inventor 陈海峰李崇张兆超张小庆唐丹丹
Owner JIANGSU SUNERA TECH CO LTD
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