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Triphenylamine-based hole transmission materials connected by different bridged bonds and preparation method thereof

A hole transport material, triphenylamine-based technology, applied in the field of organic electroluminescence display, can solve the problems of poor film formation of small molecular compounds, unfavorable commercial application, and poor thermal stability.

Active Publication Date: 2011-09-14
TIANJIN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although these compounds have excellent hole transport properties, their thermal stability is not very good, and their glass transition temperatures Tg are 75°C, 65°C, and 98°C, respectively.
In addition, due to the poor film-forming properties of small molecular compounds, these hole transport materials can only be applied to OLED displays by vacuum evaporation, which is not conducive to commercial applications, so good hole transport materials should also have Good solubility and film-forming ability to facilitate industrialization by spin coating or inkjet coating, large area application

Method used

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  • Triphenylamine-based hole transmission materials connected by different bridged bonds and preparation method thereof
  • Triphenylamine-based hole transmission materials connected by different bridged bonds and preparation method thereof
  • Triphenylamine-based hole transmission materials connected by different bridged bonds and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1～3

[0026] Examples 1 to 3 are (Z)-1,2-bis(4-N,N-di-p-tolylaminophenyl)ethylene (HTM I)

[0027]

Embodiment 1

[0028] Example 1: Synthesis of (Z)-1,2-bis(4-N,N-di-p-tolylaminophenyl)ethylene (HTM I):

[0029] Under the protection of nitrogen, 3.80g (0.02mol) of titanium tetrachloride and 60mL of tetrahydrofuran were added to a 250mL four-necked flask, 0.48g (0.02mol) of magnesium powder was added with stirring, and the reaction was refluxed for 2 hours. After cooling to room temperature, 0.60g (0.002mol) 4-(N,N-bis(4-methylphenyl)amino)benzaldehyde was added, and the reaction was stirred at room temperature for 8 hours.

[0030] Add 40 mL of 2M hydrochloric acid solution and extract with chloroform to obtain the organic layer. After drying the organic layer with anhydrous magnesium sulfate, the solvent is distilled off under reduced pressure, and the product is dissolved with 50 mL of chloroform, washed with 150 mL of deionized water three times, and collected The organic layer was dried with anhydrous magnesium sulfate, passed through a fast silica gel column (eluent: petroleum ether: ethy...

Embodiment 2

[0031] Example 2: Synthesis of (Z)-1,2-bis(4-N,N-di-p-tolylaminophenyl)ethylene (HTM I):

[0032] Under the protection of nitrogen, 5.70g (0.03mol) of titanium tetrachloride and 60mL of tetrahydrofuran were added to a 250mL four-necked flask, 0.86g (0.036mol) of magnesium powder were added with stirring, and the reaction was refluxed for 3 hours. After cooling to room temperature, 0.60g (0.002mol) 4-(N,N-bis(4-methylphenyl)amino)benzaldehyde was added, and the reaction was stirred at room temperature for 9 hours.

[0033] Add 40 mL of 2M hydrochloric acid solution and extract with chloroform to obtain the organic layer. After drying the organic layer with anhydrous magnesium sulfate, the solvent is distilled off under reduced pressure, and the product is dissolved with 50 mL of chloroform, washed with 150 mL of deionized water three times, and collected The organic layer was dried with anhydrous magnesium sulfate, passed through a fast silica gel column (eluent: petroleum ether: et...

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Abstract

The invention relates to triphenylamine-based hole transmission materials connected by different bridged bonds and a preparation method thereof. The triphenylamine structure-containing high-performance hole transmission materials connected by different bridged bonds are synthesized and the structure is represented; and the properties of the materials are tested and analyzed. In the triphenylamine-based hole transmission materials connected by different bridged bonds, due to high electron donating ability of the triphenylamine and a big conjugated system, the compounds have high photoelectric property and thermal stability; the compounds have high film-forming property, so the compounds can serve as the hole transmission materials in an organic electroluminescent display device to prepare a flexible display device; the hole transmission materials are easy to synthesize, have low cost and prominent photoelectric property, effectively meet the requirement that a hole jumps from a positive electrode to a hole transmission layer, show a potential application prospect in an organic electroluminescent material, and can be applied to photoconductor drums and dye sensitive solar batteries. The triphenylamine-based hole transmission materials connected by different bridged bonds have a structural formula shown in the specification.

Description

Technical field [0001] The invention relates to the field of organic electroluminescence displays, in particular to triphenylamine-based hole transport materials connected by different bridge bonds and a preparation method. Background technique [0002] Charge transport materials are important functional materials for the preparation of photoelectric conversion devices. They are mainly used in organic photoconductors (OPC), organic electroluminescence devices (OLED) and dye-sensitized solar cells (DSSC). They are used in information recording and solar energy utilization. The technical field has very important uses. According to the properties of transporting charges, charge transport materials can be divided into hole transport materials and electron transport materials. [0003] Hole transport materials directly affect hole injection efficiency and exciton formation, thereby affecting the brightness, efficiency, and lifetime of the device. The development of hole transport mate...

Claims

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Application Information

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IPC IPC(8): C07C211/54C07C209/66C07C209/60H01L51/50H01L27/32
Inventor 李祥高高文正王世荣吕海军
Owner TIANJIN UNIV
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