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Compounds, electron transport materials, display panels and display devices

An electron transport material and display panel technology, which is applied in the field of OLED, can solve problems such as small molecular weight, reduced device life, and increased drift voltage, and achieve the effects of avoiding the increase of intermolecular attraction, improving luminous efficiency, and improving working life

Active Publication Date: 2022-04-05
WUHAN TIANMA MICRO ELECTRONICS CO LTD +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] The combination of this structure and the metal is relatively strong, which can prevent the following from happening: the heat and electric field generated during the device driving process will cause the metal to move, thereby driving the initial electron transport layer to change, changing the electron injection and mobility characteristics, will eventually lead to reduced lifetime of the device
[0007] Compared with mono-dentate (mono-dentate) or electron transport layer materials that cannot be coordinated, double-dentate electron transport layer materials have stronger stability and longer life, but there is still the problem of increased drift voltage, and Life expectancy also needs further improvement
[0008] In addition, the most used phenanthroline (Phenanthroline), due to its small molecular weight, it is difficult to control the evaporation rate, and it has a planar molecular structure, with strong intermolecular attraction, which may block the entrance of the crucible or As a result, a lot of materials are accumulated on the baffle on the inner wall of the cavity, which is not conducive to the production process

Method used

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  • Compounds, electron transport materials, display panels and display devices
  • Compounds, electron transport materials, display panels and display devices
  • Compounds, electron transport materials, display panels and display devices

Examples

Experimental program
Comparison scheme
Effect test

Embodiment approach

[0042] According to one embodiment of the compound of the present invention, Ar is selected from any one of the following groups:

[0043]

[0044] *Indicates possible connection positions.

[0045] According to one embodiment of the compound of the present invention, Ar is selected from any one of the following groups:

[0046]

[0047] R 7 Selected from hydrogen atom, C1-C6 alkyl, C6-C18 aryl, C4-C20 heteroaryl;

[0048] *Indicates possible connection positions.

[0049] According to one embodiment of the compound of the present invention, Ar is selected from any one of the following groups:

[0050]

[0051] *Indicates possible connection positions.

[0052] According to one embodiment of the compound of the present invention, the compound is selected from one of the following compounds:

[0053]

[0054]

[0055]

[0056]

[0057]

[0058]

[0059]

[0060]

[0061]

[0062]

[0063]

[0064]

[0065]

[0066] The present ...

Embodiment 1

[0075] Synthesis of compound M004

[0076]

[0077] X002 (1.15 mmol) was dissolved in 40 mL of anhydrous tetrahydrofuran (THF) at room temperature under nitrogen atmosphere. NaH (1.4 mmol) was repeatedly washed with n-hexane, and then added to the above solution. After stirring for 1 h, X001 (1.1 mmol) was added and stirred overnight at room temperature. The reaction was quenched by adding methanol and water. Extract with dichloromethane, collect the organic phase, and wash with anhydrous Na 2 SO 4 Dry processing. The dried solution was filtered, and the solvent was removed by a rotary evaporator to obtain a crude product. The crude product was purified by silica gel chromatography using chloroform / n-hexane as eluent to obtain intermediate X003 (0.94 mmol, yield 85%).

[0078] MALDI-TOF MS: C 15 h 8 Cl 2 N 4 : m / z calculated: 314.0; tested: 314.2.

[0079]

[0080] X004 (1.15 mmol) was dissolved in 45 mL of anhydrous THF at room temperature under nitrogen atmo...

Embodiment 2

[0087] Synthesis of compound M037

[0088]

[0089] Under nitrogen protection, weigh compound X005 (1.3mmol), X007 (1.45mmol), [Pd 2 (dba) 3 ]·CHCl 3 (0.06mmol) and HP(tBu) 3 ·BF 4 (0.12mmol), was added to a 250mL two-necked flask. Inject 60mL of toluene into the two-necked flask (pass N in advance 2 15min to remove oxygen), and then add 6mL concentration of 1M K 2 CO 3 Aqueous solution (pass N in advance 2 15min to remove oxygen), and stirred overnight at room temperature. After the reaction was completed, 20 mL of deionized water was added, followed by a few drops of 2M HCl. Extract with dichloromethane, collect the organic phase, and wash with anhydrous Na 2 SO 4 Dry processing. The dried solution was filtered, and the solvent was removed by a rotary evaporator to obtain a crude product. The crude product was purified by silica gel column chromatography, and the final purification afforded solid M037 (1.03 mmol, 79%).

[0090] MALDI-TOF MS: C 37 h 21 N ...

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Abstract

The invention belongs to the field of OLED technology and provides a compound used as an electron transport material, which has a structure shown in Chemical Formula 1, wherein X 1 -X 4 each independently selected from a carbon atom or a nitrogen atom, and X 1 –X 4 At least two of them are nitrogen atoms; R 1 -R 4 independently selected from absence, hydrogen atom, C1-C20 alkyl, C1-C20 alkoxy, C1-C20 alkylthio, C1-C20 alkylamino, C6-C30 aryl, C2-C30 heteroaryl; m selected from 1 or 2; n and q are each independently selected from 0, 1, 2 and n+q≥1; and m+n+q=3; Ar is selected from C6-C30 aryl. The molecular structure of the compound described in the present invention has multi-dentate nitrogen-containing ligands, which can be complexed with Yb metal or LiQ to form a metal-organic complex with multi-dentate combination. When it is applied to OLED devices, it can effectively The light-on voltage of the OLED device is reduced, the operating voltage of the OLED device is reduced, the luminous efficiency of the OLED device is improved, and the working life of the OLED device is improved at the same time. The invention also provides a display panel and a display device.

Description

technical field [0001] The invention belongs to the technical field of OLEDs, and in particular relates to a compound that can be used as an electron transport material, an electron transport material comprising the compound, a display panel and a display device. Background technique [0002] The electron transport material used in traditional electroluminescent devices is Alq3, but the electron mobility of Alq3 is relatively low (about l0 -6 cm 2 / Vs), which makes the electron transport and hole transport of the device unbalanced. With the commercialization and practical application of electroluminescent devices, people hope to obtain electron transport materials with higher transport efficiency and better performance. In this field, researchers have done a lot of exploratory work. [0003] The material used for the electron transport layer should avoid absorbing visible light. In order to receive electrons from the cathode, a LUMO energy of about 2.4 to 3.0 eV is requir...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D471/14C07D519/00C07F9/6568C07F7/08H01L51/50H01L51/54
CPCC07D519/00C07F9/65685C07F7/0816C07D471/04C07F7/0812H10K85/624H10K85/626H10K85/615H10K85/654H10K85/6576H10K85/6574H10K85/6572H10K85/657H10K85/40H10K50/16H10K50/18C07D471/14H10K50/19H10K50/165H10K50/171H10K50/131H10K50/125
Inventor 高威翟露张磊冉佺代文朋过宇阳李侠
Owner WUHAN TIANMA MICRO ELECTRONICS CO LTD