A ketone-containing compound and its application in organic electroluminescent devices

A ketone compound and compound technology, applied in the application field of organic electroluminescent devices, can solve the problems of efficiency roll-off, difficult and high exciton utilization rate, high fluorescence radiation efficiency, low S1 state radiation transition rate, etc. Effects of recombination efficiency, improved luminous efficiency, and improved electron injection and transport performance

Active Publication Date: 2020-11-20
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 features and a very small S1-T1 state energy gap, although high T can be achieved through the TADF process 1 →S 1 State exciton conversion rate, but at the same time lead to low S1 state radiative transition rate, therefore, it is difficult to have both (or simultaneously achieve) high exciton utilization rate 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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  • A ketone-containing compound and its application in organic electroluminescent devices
  • A ketone-containing compound and its application in organic electroluminescent devices
  • A ketone-containing compound and its application in organic electroluminescent devices

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0082] Embodiment 1: the synthesis of compound 1:

[0083]

[0084] In a 250ml three-neck flask, under the protection of nitrogen, add 0.01mol raw material A1, 0.012mol intermediate B1, 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, with an HPLC purity of 99.19% and a yield of 62.3%;

[0085] Elemental analysis structure (molecular formula C 46 h 41 NO 2 ): theoretical value C, 86.35; H, 6.46; N, 2.19; 0, 5.00; test value: C, 86.41; ESI-MS(m / z)(M + ): The theoretical value is 639.84, and the measured value is 639.91.

Embodiment 2

[0086] Embodiment 2: the synthesis of compound 3:

[0087]

[0088] The preparation of compound 3 is the same as in Example 1, except that raw material A1 is replaced by raw material A2;

[0089] Elemental analysis structure (molecular formula C 46 h 41 NO 2 ): theoretical value C, 86.35; H, 6.46; N, 2.19; O, 5.00; test value: C, 86.42; H, 6.53; N, 2.22; ESI-MS(m / z)(M +): The theoretical value is 639.84, and the measured value is 639.93.

Embodiment 3

[0090] Embodiment 3: the synthesis of compound 11:

[0091]

[0092] The preparation of compound 11 is the same as in Example 1, except that raw material A2 is used to replace raw material A1, intermediate B2 is used to replace intermediate B1; elemental analysis structure (molecular formula C 48 h 35 NO 2 ): theoretical value C, 87.64; H, 5.36; N, 2.13; 0, 4.86; test value: C, 87.67; ESI-MS(m / z)(M + ): The theoretical value is 657.81, and the measured value is 657.95.

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Abstract

The invention discloses a compound containing ketone and its application in organic electroluminescent devices, belonging to the field of semiconductor applications. The compound contains a ketone structure and has strong rigidity. After connecting the structure of spiroazaanthrene fluorene derivatives, it has the characteristics of intermolecular crystallization and aggregation, and good film-forming properties; the compound of the present invention has bipolarity, branched The chain is an electron-donating group. Because the electron-donating ability of the group is different, 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 high triplet energy level, which can be 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; at the same time, the life of the device is significantly improved.

Description

technical field [0001] The invention relates to the technical field of semiconductors, in particular to a compound containing ketone and nitrogen heterocycle in the structure 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...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D405/04C07D405/10C07D405/12C07D405/14C07D219/02C07D221/20C07D409/04C07D401/04C09K11/06H01L51/50H01L51/54
CPCC07D405/04C07D405/10C07D405/12C07D405/14C07D219/02C07D221/20C07D409/04C07D401/04C09K11/06C09K2211/1007C09K2211/1011C09K2211/1014C09K2211/1029C09K2211/1088C09K2211/1092H10K85/626H10K85/615H10K85/6576H10K85/6574H10K85/6572H10K50/11
Inventor 李崇王芳张兆超庞羽佳
Owner JIANGSU SUNERA TECH CO LTD
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