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Phosphate group based small-molecule water/alcohol soluble material and preparation method and application thereof

A phosphonate group, alcohol-soluble material technology, used in semiconductor/solid-state device manufacturing, chemical instruments and methods, compounds of Group 5/15 elements of the periodic table, etc. Problems such as polymer molecular weight and structural uncertainty, to achieve the effect of easy purification, avoid batch instability, and strong electrophilicity

Inactive Publication Date: 2014-12-31
SOUTH CHINA UNIV OF TECH +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] In the research of such water / alcohol-soluble interface materials, one is polyelectrolyte containing anion and cation, and the other is neutral polymer containing amino group, hydroxyl group and phosphonate group. Good results have been achieved in interface modification, but due to the uncertainty of the molecular weight and structure of the polymer itself, different batches of interface materials have different effects on device performance
At the same time, most of these materials (referring to neutral polymers containing amino groups, hydroxyl groups, and phosphonate groups) are polymers with neutral group fluorene as the main chain, which is very helpful for the introduction of electrical groups such as triphenylamine or There are few reports on small molecule water / alcohol soluble materials with electro-absorbing groups such as triazine and used for electrode interface modification of organic / polymer optoelectronic devices

Method used

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  • Phosphate group based small-molecule water/alcohol soluble material and preparation method and application thereof
  • Phosphate group based small-molecule water/alcohol soluble material and preparation method and application thereof
  • Phosphate group based small-molecule water/alcohol soluble material and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0041] A kind of small molecule water / alcohol soluble material based on phosphonate group, its synthetic method comprises the following steps:

[0042] Step 1: Synthesis of 2-bromo-9,9-di(6'-bromohexyl)fluorene

[0043]

[0044]Under nitrogen protection, 200ml of 50% aqueous potassium hydroxide solution, phase transfer catalyst tetrabutylammonium bromide (3.87g, 0.012mol) and 1,6-dibromohexane (109.79g, 0.45 mol), heated to 70°C and stirred for 0.5 hours. After that, 2-bromofluorene (22.05 g, 0.09 mol) was added slowly, and reacted at 75° C. for 2 hours. Add appropriate amount of concentrated hydrochloric acid to neutralize and cool with ice water. Extract with dichloromethane, wash the organic layer 3 times with concentrated brine, dry over anhydrous magnesium sulfate, filter with suction, and remove the solvent and excess 1,6-dibromohexane from the filtrate under reduced pressure to obtain a yellow liquid. Using petroleum ether as the mobile phase to pass through the c...

Embodiment 2

[0077] A kind of small molecule water / alcohol soluble material based on phosphonate group, its synthetic method comprises the following steps:

[0078] Steps one to seven are the same as steps one to seven of embodiment 1;

[0079] Step 8: Synthesis of Compound 2TPA-2(F-EP)

[0080]

[0081] Under nitrogen protection, 2-boronic acid pinacol ester-9,9-bis(6'-phosphoethylhexyl)fluorene (2.20 g, 3.0 mmol) was dissolved in 12 ml of toluene and added to a 100 ml reactor, followed by Join N 4 ,N 4 -Bis(4-iodophenyl)-N 4 ,N 4’ -Diphenylbiphenyl-4,4'-diamine (0.89g, 1.2mmol), 18ml of toluene, after stirring for half an hour, add 15ml of 2 mol / liter potassium carbonate solution, 10ml of absolute ethanol, and the reaction system is The catalyst Pd(PPh 3 ) 4 (0.084g, 0.072mmol), stirred for half an hour and then heated to 80°C for 24 hours. After cooling to room temperature, it was extracted with ethyl acetate, washed three times with saturated brine, and the obtained organic ...

Embodiment 3

[0084] A kind of small molecule water / alcohol soluble material based on phosphonate group, its synthetic method comprises the following steps:

[0085] Steps one to four are the same as steps one to four of embodiment 1;

[0086] Step five: the synthesis of compound TPA-3 (F-EP)

[0087]

[0088] Under nitrogen protection, 2-boronic acid pinacol ester-9,9-bis(6'-phosphoethylhexyl)fluorene (3.51g, 4.8mmol) was dissolved in 15ml of toluene and added to a 250ml reactor, followed by Add 4,4',4"-triiodotriphenylamine (0.75g, 1.2mmol), 20ml of toluene, stir for half an hour, add 15ml of 2 mol / L potassium carbonate solution, 10ml of absolute ethanol, and the reaction system is in a nitrogen atmosphere Add catalyst Pd(PPh 3 ) 4 (0.208g, 0.18mmol), stirred for half an hour and then heated to 80°C for 24 hours. After cooling to room temperature, it was extracted with ethyl acetate, washed three times with saturated brine, and the obtained organic layer was dried over anhydrous ma...

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Abstract

The invention discloses a phosphate group based small-molecule water / alcohol soluble material and a preparation method and application thereof. The structural formula of the material is shown as follows, wherein the n ranges from 0 to 20, the R represents alkyl with the carbon atomic number of 1-20, and Ar, Arl and Ar2 represent heteroaromatic compound, derivatives of triphenylamine and derivatives of fluorene or carbazole respectively. Owning to certainty of structure and molecular weight of the phosphate group based small-molecule water / alcohol soluble material, unstability of batches of polymer interface materials is avoided. The phosphate group based small-molecule water / alcohol soluble material has the advantages of good dissolvability and film forming property, stability in film form, high eletrophilicity, good interference modificability, and low electronic injection / extraction capacity. By changing number of the phosphate groups and chemical structures for connecting the groups of the phosphate group based small-molecule water / alcohol soluble material, dissolvability, thermal stability, film forming property and electrophilicity of products can be regulated and controlled effectively, and expansion of application scope of the phosphate group based small-molecule water / alcohol soluble material is facilitated.

Description

technical field [0001] The invention relates to a class of water / alcohol-soluble phosphonate materials based on small organic molecules, in particular to a class of phosphonate materials with fluorene containing phosphonate groups in their side chains as constituent units and a preparation method thereof, and to the class of phosphonate materials The application of materials in the electrode interface modification layer of organic photoelectric devices including organic / polymer light-emitting diodes and organic / polymer solar cells. Background technique [0002] In the past two decades, due to the excellent potential of lightness, softness, economy, and ease of industrialization, organic optoelectronics have increasingly become a hot spot in commercial and scientific research. In order to continuously improve the performance and life of devices, while continuously developing high-performance and high-stability active layer materials, the development and research of interface ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07F9/40H01L51/52H01L51/44H01L51/54H01L51/46
CPCY02E10/549
Inventor 苏仕健周虎陈东成赵伟明
Owner SOUTH CHINA UNIV OF TECH
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