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A compound containing spiroxanthene fluorene and nitrogen-containing six-membered heterocycle, its preparation method and its application in organic electroluminescent devices

An electroluminescent device, a six-membered heterocycle technology, applied to compounds containing spiroxanthrene and nitrogen-containing six-membered heterocycles, the application field of organic electroluminescent devices, can solve the problems of different, to avoid Aggregation, improvement of power efficiency and external quantum efficiency, and beneficial effect of energy transfer

Active Publication Date: 2022-04-19
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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  • A compound containing spiroxanthene fluorene and nitrogen-containing six-membered heterocycle, its preparation method and its application in organic electroluminescent devices
  • A compound containing spiroxanthene fluorene and nitrogen-containing six-membered heterocycle, its preparation method and its application in organic electroluminescent devices
  • A compound containing spiroxanthene fluorene and nitrogen-containing six-membered heterocycle, its preparation method and its application in organic electroluminescent devices

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0081] The preparation of embodiment 1 boric acid compound A

Embodiment 1-1

[0082] The preparation of embodiment 1-1 boronic acid compound A8

[0083]

[0084] Step 1: In a 250mL three-necked flask, blow nitrogen, add 0.04mol 2,4,6-trichloropyridine, 150mlTHF, 0.05mol 4-biphenylboronic acid, 0.0004molPd(PPh 3 ) 4 , stirred, and then added 30 mL of K 2 CO 3 Aqueous solution (molar concentration: 2M), heated to 80°C, refluxed for 10h, 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 intermediate X with a HPLC purity of 99.5% and a yield of 75.4%. Elemental analysis structure (molecular formula C 17 h 11 Cl 2 N): Theoretical C, 68.02; H, 3.69; Cl, ​​23.62; N, 4.67; Found: C, 68.02; H, 3.68; Cl, ​​23.64; N, 4.66. ESI-MS(m / z)(M + ): The theoretical value is 299.03, and the measured value is 299.45.

[0085]

[0086] Step 2: In a 250mL three-necked fl...

Embodiment 2

[0097] Example 2 Preparation of compounds containing spiroxanthene fluorene and nitrogen-containing six-membered heterocycle

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Abstract

The invention discloses a compound containing spiroxanthene fluorene and nitrogen-containing six-membered heterocycle, its preparation method and its application in organic electroluminescent devices. The spiroxanthene fluorene structure contained in the compound has strong Rigidity, and after connecting the nitrogen-containing six-membered heterocyclic long-chain branched structure, the compound has the characteristics of intermolecular crystallization, aggregation, and good film-forming properties. The compound of the present invention has a bipolar core, and the branch chain is an electron-withdrawing group, and the strength of the branch-chain group’s electron-absorbing ability is different. Therefore, the HOMO energy level of the material is different, and it can be used as a material for different functional layers. . In addition, the compound of the present invention has a higher triplet state energy level, which can effectively block energy loss and facilitate energy transfer. Therefore, after the compound of the present invention is used as an organic electroluminescent functional layer material in an OLED device, the current efficiency, power efficiency and external quantum efficiency of the device are greatly improved, and at the same time, the life of the device is significantly improved.

Description

technical field [0001] The invention relates to the technical field of photoelectric materials, in particular to a compound containing spiroxanthene fluorene and a nitrogen-containing six-membered heterocycle, a preparation method thereof and an application in organic electroluminescent devices. Background technique [0002] Organic Light Emission Diodes (OLED) 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 broad 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 device. As a current device, when a voltage is applied to the electrodes at...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D405/14C07D405/10C07D405/04C07D471/04C07D413/14C09K11/06H01L51/50H01L51/54
Inventor 王芳张兆超李崇张小庆
Owner JIANGSU SUNERA TECH CO LTD
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