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Benzophenone group-containing photo-crosslinkable hole transport material as well as preparation method and application thereof

A hole-transporting material, benzophenone-based technology, applied in the direction of light-emitting materials, chemical instruments and methods, semiconductor/solid-state device manufacturing, etc., can solve the problems of not being able to obtain high-performance stacked devices, and achieve the realization of carrier Effects of Transport Balance, Less Damage, and High Hole Injection and Transport Capabilities

Active Publication Date: 2020-11-27
SHANGHAI JIAO TONG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, when using the solution method to prepare QLED devices, especially when using the inkjet printing process, the benzene-based solvents of the quantum dots will dissolve the TFB, and high-performance stacked devices cannot be obtained.

Method used

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  • Benzophenone group-containing photo-crosslinkable hole transport material as well as preparation method and application thereof
  • Benzophenone group-containing photo-crosslinkable hole transport material as well as preparation method and application thereof
  • Benzophenone group-containing photo-crosslinkable hole transport material as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0046] The preparation method of embodiment 1, TFB-BP

[0047] 1) Preparation of Monomer 1

[0048] Under nitrogen protection, tris(4-bromophenyl)amine (16.00g, 33.2mmol) was dissolved in anhydrous THF (88.0mL), the reaction system was stirred in an ethanol bath at -78°C, and n-butyl Balithium (17.26mL, 2.5M in hexane, 43.15mmol) was added dropwise to the reaction system. After reacting at -78°C for 1h, anhydrous DMF (16mL) was added to the reaction flask. After the dropwise addition, the reaction was continued at -78° C. for 1 h, the temperature of the system was returned to room temperature and the reaction was continued for 1 h, and deionized water was added to quench the reaction. The mixture was extracted three times with ether, the organic phases were combined, the organic layer was washed three times with saturated sodium chloride solution, dried over anhydrous magnesium sulfate, and the solvent was evaporated by a rotary evaporator. Using petroleum ether / ethyl acet...

Embodiment 2

[0074] Embodiment 2, thermal stability, photophysics and electrochemical performance, solvent resistance and surface of TFB-BP hole transport material Surface morphology characterization and analysis

[0075] Figure 4 For the thermogravimetric loss (TGA) and differential scanning calorimetry (DSC) figure of the photocrosslinking hole transport material TFB-BP (polymer 1) that embodiment 1 prepares, by Figure 4 It can be seen that the decomposition temperature of the polymer TFB-BP is 326°C and the glass transition temperature is 123.8°C when the thermal weight loss fraction of the polymer TFB-BP is 5%, and the polymer TFB-BP has good thermal stability.

[0076] Figure 5 It is the ultraviolet-visible absorption spectrum of TFB-BP (polymer 1) before and after crosslinking. It can be seen from the figure that the initial absorption wavelengths of the film before and after crosslinking of TFB-BP are 429nm and 432nm, and the initial absorption wavelengths of the two before ...

Embodiment 3

[0081] Example 3, Preparation and Characterization of Single Hole Devices (HOD) Based on Different Hole Transport Materials

[0082] In order to verify that the cross-linked material TFB-BP has high hole transport performance, we prepared a single-hole device based on TFB, uncross-linked TFB-BP and cross-linked TFB-BP. The structure of the device is: ITO (160nm) / PEDOT:PSS(32nm) / HTL(25nm) / QDs(15nm) / MoO 3 (2nm) / Al(100nm).

[0083] Figure 8 It is the current density-voltage curve of single hole device (HOD) based on different hole transport materials. It can be seen from the figure that at low voltage, the current density of TFB-BP before and after photocrosslinking is lower than that of the reference TFB, showing the Low leakage current; TFB-BP (polymer 1) after cross-linking compared to before cross-linking ( Figure 8 TFB-BP in ) has a lower leakage current, which is due to the denser film after cross-linking, which can effectively prevent leakage current; when the volt...

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Abstract

The invention discloses a benzophenone group-containing photo-crosslinkable hole transport material as well as a preparation method and application thereof. The hole transport material is a polymer hole transport material taking TFB as a parent nucleus and benzophenone as a cross-linking group, and the chemical structural formula is shown in the specification, wherein, in the formula, x and y aremolar fractions, x is greater than 0 and less than 1, and y is greater than 0 and less than 1. The material film forms a three-dimensional network structure under ultraviolet radiation to realize cross-linking of the material, and a cross-linking material with solvent resistance is obtained, so that preparation of a light-emitting device by an all-solution method is realized. The cross-linked material has high hole injection and transmission capability, the performance is obviously superior to that of a commercial TFB hole transport material, an initiator or a catalyst does not need to be added in the photo-crosslinking method, the crosslinking time is short, no by-product is produced in the reaction process, the required ultraviolet excitation wavelength is long (365nm), the damage degreeto the material is small, and the influence on the electrical and optical properties of the hole transport material before and after crosslinking is small.

Description

technical field [0001] The present invention relates to the field of organic optoelectronic technology, in particular to a crosslinkable hole transport material and its preparation method and application, especially to a photocrosslinkable hole transport material containing benzophenone group and its preparation method with application. Background technique [0002] Quantum-dot light-emitting diode (QLED) is an electroluminescent device that uses quantum dots as the light-emitting layer. The organic quantum dot light-emitting diodes prepared based on the solution method are more and more widely used in the fields of flexible display, printed display and semiconductor lighting due to their high external quantum dot conversion efficiency, high brightness and color purity, and wider color gamut. QLED light depends on electroluminescence, and the holes injected from the anode and the electrons injected from the cathode are transported to the valence band and conduction band of ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08G61/12H01L51/50H01L51/54C09K11/06
CPCC08G61/12C09K11/06C08G2261/122C08G2261/1412C08G2261/148C08G2261/1426C08G2261/3142C08G2261/3162C08G2261/411C08G2261/512C08G2261/5222C08G2261/95C08G2261/1428C08G2261/76C09K2211/1416C09K2211/1425C09K2211/1433H10K85/111H10K85/151H10K50/115H10K50/15
Inventor 孙文建尹晓宽张清郭小军
Owner SHANGHAI JIAO TONG UNIV