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Compound with spirodimethylanthracene-fluorene and nitrogenous six-membered heterocycles and application thereof in organic light-emitting devices

A technology of dimethylanthracene fluorene and six-membered heterocyclic ring, which is applied in the fields of electric solid-state devices, electrical components, organic chemistry, etc., can solve different problems and achieve the effects of blocking energy loss, facilitating energy transfer, and good application effects

Inactive 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 with spirodimethylanthracene-fluorene and nitrogenous six-membered heterocycles and application thereof in organic light-emitting devices
  • Compound with spirodimethylanthracene-fluorene and nitrogenous six-membered heterocycles and application thereof in organic light-emitting devices
  • Compound with spirodimethylanthracene-fluorene and nitrogenous six-membered heterocycles and application thereof in organic light-emitting devices

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0079] Embodiment 1: the synthesis of 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 A1, 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 49 h 35 N 3 ): theoretical value C, 88.39; H, 5.30; N, 6.31; test value: C, 88.47; H, 5.36; N, 6.35. ESI-MS(m / z)(M + ): The theoretical value is 665.28, and the measured value is 665.34.

Embodiment 2

[0082] Embodiment 2: the synthesis of compound 13:

[0083]

[0084] In a 250mL three-necked flask, nitrogen was introduced, 0.01mol of raw material A2, 150ml of THF, 0.015mol of intermediate A1, 0.0001mol of tetrakis(triphenylphosphine) palladium were added, stirred, and then 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 49 h 35 N 3 ): theoretical value C, 88.39; H, 5.30; N, 6.31; test value: C, 88.47; H, 5.36; N, 6.35. ESI-MS(m / z)(M + ): The theoretical value is 665.28, and the measured value is 665.35.

Embodiment 3

[0085] Embodiment 3: the synthesis of compound 25:

[0086]

[0087] The preparation method of compound 25 is the same as that in Example 1, except that raw material A1 is replaced by raw material A3, and intermediate A1 is replaced by intermediate A2.

[0088] Elemental analysis structure (molecular formula C 55 h 39 N 3 ): theoretical value C, 89.04; H, 5.30; N, 5.66; test value: C, 89.11; H, 5.28; N, 5.65. ESI-MS(m / z)(M + ): The theoretical value is 741.31, and the measured value is 741.39.

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Abstract

The invention discloses a compound with spirodimethylanthracene-fluorene and nitrogenous heterocycles and application thereof in organic light-emitting devices. With spirodimethylanthracene-fluorene structure, the compound herein has great rigidity. After nitrogenous six-membered heterocyclic long-chain branch structure is linked to the compound, the compound features rarity of intermolecular crystallization and gathering, good film-forming capacity and the like. Since the stem nucleus is bipolar and the branch chains are electron-withdrawing groups which have different electron-withdrawing capacities, materials have different HOMO (highest occupied molecular orbital) energy levels and may act as different functional layer materials. In addition, with high trilinear energy level, the compound can effectively block energy loss and facilitate energy transfer. Therefore, after the compound is applied as an organic light-emitting functional layer material to OLED devices, all current efficiency, power efficiency and external quantum efficiency of the devices can be greatly improved. Furthermore, the service lives of the devices are significantly extended.

Description

technical field [0001] The invention relates to the technical field of semiconductors, in particular to a compound containing spirodimethylanthracene fluorene and nitrogen-containing six-membered heterocycle and its application in organic electroluminescent devices. Background technique [0002] Organic electroluminescence (OLED: Organic Light Emission Diodes) device technology can not only be used to manufacture new display products, but also can be used to make new lighting products, and is expected to replace the existing liquid crystal display and fluorescent lighting, and has a very wide application prospect . The OLED light-emitting device is 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 ...

Claims

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Application Information

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IPC IPC(8): C07D251/24C07D405/04C07D403/04C07D401/04C07D401/14C07D471/04C07D403/10C07D413/10C07D413/04C07D213/16C07D213/22C07D213/06C07D401/10C07D239/26H01L51/50H01L51/54
Inventor 王芳李崇张兆超张小庆
Owner JIANGSU SUNERA TECH CO LTD
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