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Alcohol-soluble hole-transporting molecular material and preparation method thereof

A technology of hole transport and molecular materials, which is applied in the field of alcohol-soluble hole transport molecular materials and its preparation, can solve problems affecting device stability, device performance is difficult to control, and is difficult to overcome, so as to achieve convenient purification, avoid performance and lifespan , the effect of good performance

Inactive Publication Date: 2012-08-29
SOUTH CHINA UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

But as a kind of strongly acidic polymer material, it also has its own shortcomings that are difficult to overcome.
On the one hand, strong acidity will corrode the metal oxide anode material, thereby affecting the stability of the device; on the other hand, due to the uncertainty of the structure of the polymer itself, such as the polydispersity of molecular weight, it is difficult to control the performance of the device.

Method used

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  • Alcohol-soluble hole-transporting molecular material and preparation method thereof
  • Alcohol-soluble hole-transporting molecular material and preparation method thereof
  • Alcohol-soluble hole-transporting molecular material and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0040] As shown in the following formula, the preparation process of the alcohol-soluble hole transport molecular material of this embodiment is as follows:

[0041]

[0042] Step 1: slowly pour 2-bromoethanol (50g, 0.4mol) into dihydropyran (67g, 0.8mol) stirred in a flask, and cool with an ice-water bath. After pouring, add concentrated hydrochloric acid (12mol / L, 2mL), after 8h, the reaction solution turned black. After distillation under reduced pressure, a colorless oily liquid 1 was obtained.

[0043] Step 2: Pour 2,7-dibromofluorene (3.24g, 10mmol) into a flask, add dimethyl sulfoxide (30mL) and stir to exhaust until all solids are dissolved, then add KOH (5.8g, 104.1mmol), Reacted for 1 h under the protection of nitrogen, the solution gradually turned reddish brown. Then 1 (4.6g, 22mmol) was slowly added dropwise into the reaction flask, and reacted in an ice-water bath for 8h. The mixture was extracted and column chromatographed to give 2 as a white solid.

[...

Embodiment 2

[0056] As shown in the following formula, the preparation process of the alcohol-soluble hole transport molecular material of this embodiment is as follows:

[0057]

[0058] Step 1: Preparation 6. The process of preparation 6 in this example is the same as that in Example 1, and will not be repeated here.

[0059] Step 2: Dissolve 6 (1.6g, 1.6mmol) in dry THF (60mL), protect with nitrogen, and cool to -78°C. Slowly add n-BuLi (1.6M, 1 mL, 1.6 mmol) dropwise into the reaction flask. After the dropwise addition was completed, stirring was continued at -78°C for 1 h, and then 4,4,5,5-tetramethyl-1,3,2-isopropanol borate (0.3 mg, 1.6 mmol) was added with a syringe, Then naturally warmed to room temperature and stirred for 24h. After the mixture was terminated with ethanol, ethanol and THF were removed by rotary distillation, and the remaining solid was extracted and column chromatographed to obtain 8 as a yellow solid.

[0060] Step 3: Add 6 (0.5g, 0.5mmol), 8 (0.5g, 0.5mmo...

Embodiment 3

[0063] As shown in the following formula, the preparation process of the alcohol-soluble hole transport molecular material of this embodiment is as follows:

[0064]

[0065] Step 1: Slowly pour 6-bromo-1,2-hexanediol (50g, 254mmol) into dihydropyran (64g, 760mmol) stirred in a flask, and cool it in an ice-water bath. Concentrated hydrochloric acid (0.63mL, 12mol / L) was added after 8h. After distillation under reduced pressure, 10 was obtained as a colorless oily liquid.

[0066] Step 2: Pour 2,7-dibromofluorene (1.62g, 5mmol) into a flask, add dimethyl sulfoxide (30mL) and stir to exhaust until the solids are completely dissolved, then add KOH (2.8g, 50mmol), in Under the protection of nitrogen, the reaction was carried out for 1 h, and the solution gradually turned reddish brown. Then 1 (4.0g, 11mmol) was slowly added dropwise into the reaction flask, and reacted in a 50°C water bath for 36h. The mixture was extracted and column chromatographed to give 11 as a colorles...

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Abstract

The invention discloses an alcohol-soluble hole-transporting molecular material and a preparation method thereof. A plurality of hydroxyl groups are introduced into aromatic amine molecules, so that the prepared material has excellent hot-transporting performance and alcohol solubility, and is insoluble in other types of solvents such as toluene, chlorobenzene, dichloromethane, chloroform and the like. During the preparation, the alcohol-soluble hole-transporting molecular material is prepared by the following steps: protecting the hydroxyl groups of alkane, aromatic hydrocarbon, alkane derivative or aromatic hydrocarbon derivative containing the hydroxyl groups through dihydropyran; obtaining an aromatic amino precursor through reaction such as Suzuki coupling, Ullmann coupling, Stille coupling and the like; and finally removing the protective groups to obtain the target product. The material can perform film formation in alcohol solution, can resist corrosion by other solvents such as toluene, chlorobenzene, dichloromethane, chloroform and the like, and has application prospect in solution processing of multi-layer organic photoelectric devices.

Description

technical field [0001] The invention relates to a hole-transporting molecular material, in particular to an alcohol-soluble hole-transporting molecular material and a preparation method thereof. Background technique [0002] In 1987, Tang and VanSlyke prepared a multilayer thin-film electroluminescent device using small-molecule organometallic complexes of octahydroxyquinoline aluminum as electron transport and light-emitting layer materials, making a pioneering effort in the design of organic light-emitting diodes (OLEDs) work. In 1990, scientists at the University of Cambridge reported for the first time polymer electroluminescent devices prepared from soluble precursors; in 1991, Heeger and Braun reported polymer thin film electroluminescent devices prepared by spin-coating polymer solutions. At present, small molecule electroluminescence devices based on vacuum thermal evaporation film formation technology have been successfully applied to the display screens of some co...

Claims

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Application Information

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IPC IPC(8): C07C215/74C07C215/76C07C215/86C07C215/88C07C213/02C07D209/82C07D333/36C07D409/04C07D409/10C09K11/06
CPCY02P20/55
Inventor 朱旭辉邵剑刘刚李艳虎彭俊彪曹镛
Owner SOUTH CHINA UNIV OF TECH
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