Organic compound, electron transport material and application thereof

An organic compound and selected technology, applied in the field of organic compounds and electron transport materials, can solve the problems of affecting the luminous efficiency and stability of devices, imbalance of electron and hole mobility, poor carrier transport balance, etc. Electron flow, reduced exciton blocking, favorable balance effects

Pending Publication Date: 2021-03-05
WUHAN TIANMA MICRO ELECTRONICS CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the glass transition temperature of electron transport materials represented by the above compounds is low, generally less than 85°C. When the device is running, the Joule heat generated will lead to molecular degradation and molecular structure changes, resulting in low luminous efficiency of the device. 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 decrease in the performance of electron transport, an imbalance in the electron and hole mobility of the entire device, and a large exciton formation efficiency. 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 device efficiency and lifetime
At the same time, the electron mobility of existing electron transport materials is generally low, which is 1 to 2 orders of magnitude lower than that of hole transport materials, which makes the carrier transport balance of the device poor and seriously affects the luminous efficiency of the device. and stability

Method used

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  • Organic compound, electron transport material and application thereof
  • Organic compound, electron transport material and application thereof
  • Organic compound, electron transport material and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0088] This embodiment provides an organic compound M1 with the following structure:

[0089]

[0090] The preparation method of this organic compound M1 comprises the steps:

[0091]

[0092] Add compound A (2.94g, 20mmol), compound B (2.46g, 20mmol), 150mL toluene, sodium tert-butoxide NaOt-Bu (2.88g, 30mmol) and tri(di Benzylideneacetone) Dipalladium Pd 2 (dba) 3 (0.18g, 0.2mmol), and then reacted at 120°C for 24h under nitrogen atmosphere. Cool to room temperature, pour the reaction solution into 200 mL of ice water, extract three times with dichloromethane, combine the organic phases, spin into silica gel, and perform column chromatography (the mobile phase is a mixed solution of dichloromethane and n-hexane with a volume ratio of 1:1) Separate and purify to obtain compound C.

[0093] Characterization results of compound C:

[0094] 1 H-NMR (400MHz, CDCl 3 ): δ8.74-8.69 (m, 2H), 7.90 (t, J = 4.5Hz, 2H), 7.83 (t, J = 4.4Hz, 2H), 7.55-7.50 (m, 2H);

[0095] ...

Embodiment 2

[0107] This embodiment provides an organic compound M2 with the following structure:

[0108]

[0109] The preparation method of this organic compound M2 comprises the steps:

[0110]

[0111] Add compound A (2.94g, 20mmol), compound B-2 (2.51g, 20mmol), 150mL toluene, sodium tert-butoxide NaOt-Bu (2.88g, 30mmol) and three (dibenzylideneacetone)dipalladium Pd 2 (dba)3 (0.18g, 0.2mmol), and then reacted at 120°C for 24h under nitrogen atmosphere. Cool to room temperature, pour the reaction solution into 200 mL of ice water, extract three times with dichloromethane, combine the organic phases, spin into silica gel, and perform column chromatography (the mobile phase is a mixed solution of dichloromethane and n-hexane with a volume ratio of 1:1) Separation and purification yielded compound C-2.

[0112] Characterization results of compound C-2:

[0113] 1 H-NMR (400MHz, CDCl 3 ): δ8.09(s, 2H), 7.92(t, J=4.4Hz, 2H), 7.82(t, J=4.5Hz, 2H);

[0114] 13 C-NMR (100MHz, CD...

Embodiment 3

[0121] This embodiment provides an organic compound M3 with the following structure:

[0122]

[0123] The preparation method of this organic compound M3 comprises the steps:

[0124]

[0125] Add compound A (2.94g, 20mmol), compound B-3 (2.44g, 20mmol), 150mL of toluene, sodium tert-butoxide NaOt-Bu (2.88g, 30mmol) and three (dibenzylideneacetone)dipalladium Pd 2 (dba) 3 (0.18g, 0.2mmol), and then reacted at 120°C for 24h under nitrogen atmosphere. Cool to room temperature, pour the reaction solution into 200 mL of ice water, extract three times with dichloromethane, combine the organic phases, spin into silica gel, and perform column chromatography (the mobile phase is a mixed solution of dichloromethane and n-hexane with a volume ratio of 1:1) Separation and purification yielded compound C-3.

[0126] Characterization results of compound C-3:

[0127] 1 H-NMR (400MHz, CDCl 3 ): δ7.91(dd, J=5.6,3.4Hz,2H),7.82(dd,J=5.6,3.4Hz,2H),7.55-7.48(m,2H),7.45-7.38(m,1H), ...

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Abstract

The present invention provides an organic compound, an electron transport material and application thereof. The organic compound has a structure represented by a formula I, contains an olefin structure, and forms a large conjugated system through the mutual cooperation of a skeleton structure and a substituent group, such that the electron mobility of the material is effectively improved. Meanwhile, due to the non-planar configuration of intramolecular groups, loose molecular accumulation can be formed during evaporation film forming, the surface appearance of the film can be improved, the permeability and the pore filling capacity can be improved, and the amorphous state performance, the thermal stability and the glass-transition temperature of the electron transport material can be improved. As an electron transport material, the organic compound has relatively high electron mobility and proper energy level, can balance carriers, enhance electron injection, reduce working voltage andblock excitons, and as an electron transport layer material, can significantly improve the luminous efficiency of a device, prolong the service life and reduce turn-on voltage and power consumption.

Description

technical field [0001] The invention belongs to the technical field of organic electroluminescent materials, and in particular relates to an organic compound, an electron transport material and applications thereof. Background technique [0002] Organic electroluminescent technology is an emerging technology in the field of optoelectronics. Since the rise of organic electroluminescent devices (Organic Light Emitting Diode, OLED) in 1987, it has attracted great attention from industry and science, and is considered to be the most competitive Force display technology. Compared with traditional inorganic electroluminescent devices, OLED has the advantages of fast response, low power consumption, full color, easy bending, wide viewing angle, self-illumination, ultra-thin, large-area display, high luminous efficiency, good temperature adaptability and production Due to the advantages of simple process, it has been widely used in industries such as flat panel display, flexible di...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D401/14C07D403/14C07D209/44C07D403/04C07D403/10C09K11/06H01L51/50H01L51/54H01L27/32
CPCC07D401/14C07D403/14C07D209/44C07D403/04C07D403/10C09K11/06C09K2211/1011C09K2211/1029C09K2211/1044C09K2211/1059H10K59/10H10K85/626H10K85/654H10K85/6572H10K50/16
Inventor 汪奎潘龙鑫
Owner WUHAN TIANMA MICRO ELECTRONICS CO LTD
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