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Organic compound and application thereof

An organic compound and selected technology, applied in organic chemistry, electro-solid devices, semiconductor devices, etc., can solve the problems of device electron and hole mobility imbalance, device efficiency and life decline, and exciton formation efficiency. The effect of reducing turn-on voltage and power consumption, reducing device voltage, and improving electron mobility

Active Publication Date: 2021-12-07
WUHAN TIANMA MICRO ELECTRONICS CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Electron transport materials currently widely used include bathophenanthroline (BPhen, ) and bathocuproline (BCP, ) and TmPyPB etc. These materials can generally It meets the market demand of organic electroluminescent panels, but their glass transition temperature is low, generally less than 85°C. When the device is running, the Joule heat generated will cause the degradation of molecules and the change of molecular structure, which will make the luminous efficiency of the device Low, poor thermal stability
Moreover, the symmetry of this molecular structure is very regular, and it is easy to crystallize after long-term use.
Once the electron transport material is crystallized, the intermolecular charge transition mechanism will be different from the normal operation of the amorphous film mechanism, resulting in a significant decrease in the performance of electron transport, making the electron and hole mobility of the entire device unbalanced, and the exciton formation efficiency. greatly reduced, and the formation of excitons will be concentrated at the interface between the electron transport layer and the light-emitting layer, resulting in a serious decrease in the efficiency and lifetime of the device
Moreover, in existing OLED devices, the mobility of electrons is generally 1 to 2 orders of magnitude lower than that of holes, which in turn affects the luminous efficiency of the device.

Method used

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  • Organic compound and application thereof
  • Organic compound and application thereof
  • Organic compound and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0106] A kind of organic compound M1, the structure is as follows:

[0107]

[0108] The preparation method of this organic compound M1 comprises the steps:

[0109] (1)

[0110] In a 25 mL dry reactor (Schlenk tube), sequentially add compound A1 (0.72 g, 5 mmol), compound B1 (3.09 g, 12 mmol), Li 2 CO 3 (2.22g, 30mmol), 1,4-dioxane 15mL and diacetonitrile palladium chloride PdCl 2 (CH 3 EN) 2 (12.9 mg, 0.05 mmol). The reaction mixture was evacuated (5 times) by vacuum-argon cycle and stirred at 140 °C for 24 h. After the reaction was cooled to room temperature and concentrated, the crude mixture was purified by silica gel column chromatography to afford compound Cl.

[0111] 1 H-NMR (400MHz, CDCl 3 ): δ8.61(d, J=7.5Hz, 2H), 8.15(d, J=7.5Hz, 2H), 7.54–7.46(m, 2H), 7.45–7.39(m, 2H), 7.38–7.31( m,1H),7.09(s,2H);

[0112] 13 C-NMR (100MHz, CDCl 3):δ145.58,144.67,144.61,143.88,143.82,139.30,136.57,135.69,135.64,135.62,135.59,129.58,129.57,129.56,129.54,127.88,125...

Embodiment 2

[0118] A kind of organic compound M2, the structure is as follows:

[0119]

[0120] The difference between the preparation method of the organic compound M2 and Example 1 is that the compound A1 in the step (1) is mixed with an equimolar amount of the compound A2 Replacement, other raw materials and process parameters are the same as in Example 1 to obtain the target product M2.

[0121] 1 H-NMR (400MHz, CDCl 3 ): δ8.56(q, J=15.0Hz, 4H), 7.92(s, 6H), 7.89(d, J=3.2Hz, 2H), 7.76(dt, J=4.6, 2.2Hz, 1H), 7.74 (dd, J=3.2,1.6Hz,1H),7.64(d,J=3.4Hz,2H),7.61(d,J=3.4Hz,2H),7.53–7.39(m,3H),7.34(td, J=14.9, 3.4Hz, 4H), 7.24(td, J=14.8, 3.3Hz, 4H).

Embodiment 3

[0123] A kind of organic compound M3, the structure is as follows:

[0124]

[0125] The difference between the preparation method of the organic compound M3 and Example 1 is that the compound A1 in the step (1) is mixed with an equimolar amount of the compound A3 Replacement, other raw materials and process parameters are the same as in Example 1 to obtain the target product M3.

[0126] 1 H-NMR (400MHz, CDCl 3 ): δ8.58(d, J=7.5Hz, 2H), 8.54(d, J=7.5Hz, 2H), 8.20(s, 2H), 7.90(dd, J=7.4, 1.5Hz, 4H), 7.61 (dd, J=7.4, 1.5Hz, 4H), 7.34 (td, J=7.5, 1.5Hz, 4H), 7.24 (td, J=7.5, 1.4Hz, 4H).

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Abstract

The invention provides an organic compound and application thereof. The organic compound has a structure as shown in a formula I, has a spirocyclic skeleton structure, can form an amorphous state membrane structure through interaction of the skeleton structure and a substituent group, is beneficial to electron flow so as to improve electron mobility, and has proper HOMO energy level and LUMO energy level, so that electrons can be effectively injected, and the device voltage is reduced; and meanwhile, the non-planar configuration of the intramolecular groups is beneficial to improving the amorphous performance, the thermal stability and the glass transition temperature. As an electron transport material, the organic compound has higher electron mobility, higher triplet state energy level and appropriate energy level, can balance current carriers, enhance electron injection, reduce working voltage and block excitons, can be applied to OLED devices, can improve the luminous efficiency of the devices, reduce turn-on voltage and power consumption and prolong the service life of the devices, so that the OLED devices have better comprehensive performance.

Description

technical field [0001] The invention belongs to the technical field of organic electroluminescent materials, and in particular relates to an organic compound and its application. Background technique [0002] Organic electroluminescent technology is one of the most promising photoelectric technologies at present. Compared with inorganic electroluminescent devices, organic electroluminescent devices (Organic Light Emitting Diode, OLED) have self-illumination, high contrast, wide color gamut, The advantages of flexibility and low power consumption have attracted extensive attention from scientific researchers and corporate researchers. They have been successfully applied commercially and are widely used in flexible displays, flat panel displays, and solid-state lighting and other fields. [0003] OLED devices usually have a stacked structure, including a cathode, an anode, and an organic film layer sandwiched between the two electrodes. The organic film layer includes a light-...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D487/20C07D519/00H01L51/54H01L51/50
CPCC07D487/20C07D519/00H10K85/6565H10K85/615H10K85/654H10K85/6576H10K85/6574H10K85/657H10K85/6572H10K50/16H10K50/18Y02E10/549
Inventor 汪奎潘龙鑫
Owner WUHAN TIANMA MICRO ELECTRONICS CO LTD
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