Benzil-containing compound and application thereof in organic electroluminescent devices

A compound, benzil technology, applied to organic electroluminescent devices, the field of compounds containing benzil groups, can solve problems such as differences

Inactive Publication Date: 2019-12-10
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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  • Benzil-containing compound and application thereof in organic electroluminescent devices
  • Benzil-containing compound and application thereof in organic electroluminescent devices
  • Benzil-containing compound and application thereof in organic electroluminescent devices

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0184] Embodiment 1: the synthesis of compound 1:

[0185]

[0186] In a 250ml three-neck flask, under the protection of nitrogen, add 0.01mol raw material A1, 0.024mol raw material D1, 150ml toluene and stir to mix, then add 0.06mol sodium tert-butoxide, 1×10 -4 molPd 2 (dba) 3 , 1×10 -4mol of tri-tert-butylphosphine, heated to 110°C, refluxed for 24 hours, sampled and spotted on the plate, showed that no raw material A1 remained, and the reaction was complete; naturally cooled to room temperature, filtered, and the filtrate was subjected to vacuum rotary evaporation (-0.09MPa, 85°C ), through a neutral silica gel column, to obtain the target product, HPLC purity 99.3%, yield 55.7%;

[0187] Elemental analysis structure (molecular formula C 56 h 40 N 2 o 2 ): theoretical value C, 87.02; H, 5.22; N, 3.62; O, 4.14; test value: C, 87.05; H, 5.19; N, 3.63; ESI-MS(m / z)(M + ): The theoretical value is 772.31, and the measured value is 772.43.

Embodiment 2

[0188] Embodiment 2: the synthesis of compound 5:

[0189]

[0190] 1) In a 250ml three-neck flask, under the protection of nitrogen, add 0.01mol raw material A1, 0.012mol raw material D1, 150ml toluene and stir to mix, then add 0.03mol sodium tert-butoxide, 5×10 -5 molPd 2 (dba) 3 , 5×10 -5 mol of tri-tert-butylphosphine, heated to 110°C, refluxed for 24 hours, sampled and spotted on the plate, showed that no raw material A1 remained, and the reaction was complete; naturally cooled to room temperature, filtered, and the filtrate was subjected to vacuum rotary evaporation (-0.09MPa, 85°C ), through a neutral silica gel column to obtain intermediate M1 with a HPLC purity of 98.6% and a yield of 68.2%;

[0191] 2) In a 250ml three-neck flask, under the protection of nitrogen, add 0.01mol of intermediate M1, 0.012mol of raw material D2, and 150ml of toluene, stir and mix, then add 0.03mol of sodium tert-butoxide, 5×10 -5 molPd 2 (dba) 3 , 5×10 -5 mol of tri-tert-butylph...

Embodiment 3

[0193] Embodiment 3: the synthesis of compound 7:

[0194]

[0195] The preparation method of compound 7 is the same as that of Example 1, except that raw material A1 is replaced with raw material A2.

[0196] Elemental analysis structure (molecular formula C 56 h 40 N 2 o 2 ): theoretical value C, 87.02; H, 5.22; N, 3.62; O, 4.14; test value: C, 87.03; H, 5.21; N, 3.63; ESI-MS(m / z)(M + ): The theoretical value is 772.31, and the measured value is 772.42.

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Abstract

The invention discloses a benzil-containing compound and application thereof to organic light-emitting devices. The compound contains a benzil structure, has strong rigidity, and has the characteristics of difficult crystallization between molecules, difficult aggregation and good film-forming property after being connected with a carbazole derivative long-chain branch structure; the compound disclosed by the invention has double polarity, branched chains are electron-donating groups, and the HOMO energy levels of the material are different due to different electron-donating capacities of thegroups, so that the compound can be used as different functional layer materials; in addition, the compound provided by the invention has a high triplet state energy level, can effectively block energy loss, and is beneficial to energy transfer, therefore, after application of the compound in OLED devices as an organic electroluminescent functional layer material, the current efficiency, the powerefficiency and the external quantum efficiency of the device are greatly improved; and meanwhile, the service life of the device is obviously prolonged.

Description

technical field [0001] The invention relates to the technical field of semiconductors, in particular to a compound containing a benzil group and its application in an organic electroluminescent device. 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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Patent Type & Authority Applications(China)
IPC IPC(8): C07D209/94C07D519/00C07D221/18C07D265/34C07D279/36H01L51/50H01L51/54
CPCC07D209/94C07D519/00C07D221/18C07D265/34C07D279/36H10K85/657H10K50/12H10K85/6572
Inventor 蔡啸张兆超李崇张小庆
Owner JIANGSU SUNERA TECH CO LTD
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