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Ketone-containing compound and application thereof in organic electroluminescent devices

A compound and luminescent technology, applied in the field of semiconductors, can solve problems such as efficiency roll-off, difficult exciton utilization, high fluorescence radiation efficiency, and low S1 state radiation transition rate

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

[0006] (1) The T1 and S1 states of the designed molecule have strong CT characteristics and a very small S1-T1 state energy gap, although a high T1→S1 state exciton conversion rate can be achieved through the TADF process, but at the same time lead to low S1 state radiation Transition rate, therefore, it is difficult to combine (or achieve simultaneously) high exciton utilization efficiency and high fluorescence radiation efficiency;
[0007] (2) Even if doped devices have been used to alleviate the T-exciton concentration quenching effect, the efficiency of most TADF material devices has a serious roll-off at high current densities

Method used

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  • Ketone-containing compound and application thereof in organic electroluminescent devices
  • Ketone-containing compound and application thereof in organic electroluminescent devices
  • Ketone-containing compound and application thereof in organic electroluminescent devices

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0113] Embodiment 1: the synthesis of compound H4:

[0114]

[0115] In a 250ml three-neck flask, under the protection of nitrogen, add 0.01mol raw material A1, 0.012mol intermediate D4, 150ml toluene and stir to mix, then add 0.03mol sodium tert-butoxide, 1×10 -4 molPd 2 (dba) 3 , 1×10 -4 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 ), purified through a neutral silica gel column to obtain the target product, the HPLC purity was 99.3%, and the yield was 58.7%;

[0116] Elemental analysis structure (molecular formula C 44 h 25 NO 3 ): theoretical value C, 85.84; H, 4.09; N, 2.28; test value: C, 85.88; H, 4.12; N, 2.31. ESI-MS(m / z)(M + ): The theoretical value is 615.69, and the measured value is 615.72.

Embodiment 2

[0117] Embodiment 2: the synthesis of compound H5:

[0118]

[0119] In a 250ml three-neck flask, under the protection of nitrogen, add 0.01mol raw material A1, 0.012mol intermediate D7, 150ml toluene and stir to mix, then add 0.03mol sodium tert-butoxide, 1×10 -4 molPd 2 (dba) 3 , 1×10 -4 mol of tri-tert-butylphosphine, heated to 110°C, refluxed for 24 hours, sampling plate, showed that there was no raw material A1 remaining, and the reaction was complete; naturally cooled to room temperature, filtered, and the filtrate was rotary evaporated under reduced pressure (-0.09MPa, 85°C ), purified through a neutral silica gel column to obtain the target product, the HPLC purity was 99.1%, and the yield was 67.9%;

[0120] Elemental analysis structure (molecular formula C 47 h 31 NO 2 ): theoretical value C, 87.96; H, 4.87; N, 2.18; test value: C, 87.99; H, 4.91; N, 2.23. ESI-MS(m / z)(M + ): The theoretical value is 641.77, and the measured value is 641.83.

Embodiment 3

[0121] Embodiment 3: the synthesis of compound H10:

[0122]

[0123] The preparation method of compound H10 is the same as in Example 1, except that intermediate D4 is replaced by intermediate D9.

[0124] Elemental analysis structure (molecular formula C 46 h 28 N 4 O): theoretical value C, 84.64; H, 4.32; N, 8.58; O, 2.45; tested value: C, 84.65; H, 4.31; N, 8.57; ESI-MS(m / z)(M + ): The theoretical value is 652.23, and the measured value is 652.37.

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Abstract

The invention discloses a ketone-containing compound and application thereof to an organic light-emitting devices. The compound contains a ketone structure and has strong rigidity, and connection of the compound with a spiroazaanthracene fluorene derivative structure, the compound has the characteristics of difficult crystallization among molecules, difficult aggregation and good film-forming property; 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 the group, 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 currentefficiency, the power efficiency 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 ketone-containing compound and its application in organic electroluminescent devices. 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. [0003] 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 a...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D491/107C07D405/04C07D471/10C07D497/10C07D513/10C07D495/10C07D498/10C07D405/10C07D221/20C09K11/06H01L51/50H01L51/54
CPCC07D491/107C07D405/04C07D471/10C07D497/10C07D513/10C07D495/10C07D498/10C07D405/10C07D221/20C09K11/06C09K2211/1007C09K2211/1011C09K2211/1029C09K2211/1033C09K2211/1037C09K2211/1088C09K2211/1092C09K2211/1096H10K85/615H10K85/6576H10K85/657H10K85/6574H10K85/6572H10K50/11C07D413/14C07D405/14
Inventor 李崇王芳张兆超蔡啸
Owner JIANGSU SUNERA TECH CO LTD
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