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N-type water-alcohol-soluble conjugated polymer material containing naphthalimide ring, preparation method and application

A naphthalene diimide ring and conjugated polymer technology is applied to n-type water-alcohol-soluble conjugated polymer materials and the application field of electron transport layers, and can solve the requirements of low electron mobility and device processing technology. more severe problems, to achieve the effect of improving processing technology and performance

Active Publication Date: 2017-02-01
SOUTH CHINA UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the lowest unoccupied orbital (LUMO) energy level of this type of conjugated polyelectrolyte material is high, and the electron mobility is low, so that the optimal thickness of this type of material in optoelectronic devices is only 5nm, and the requirements for device processing technology more demanding

Method used

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  • N-type water-alcohol-soluble conjugated polymer material containing naphthalimide ring, preparation method and application
  • N-type water-alcohol-soluble conjugated polymer material containing naphthalimide ring, preparation method and application
  • N-type water-alcohol-soluble conjugated polymer material containing naphthalimide ring, preparation method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0043] Preparation of 2,6-(bis-5-bromo-2-thienyl)-N,N'-diisooctyl-1,4,5,8-naphthodiimide (abbreviated as DBrNDITEH)

[0044] The chemical reaction process is as follows, and the specific reaction steps and reaction conditions are as follows:

[0045]

[0046] (1) Monomers 1 and 2 are prepared according to the method disclosed in the patent [PCT WO2011 / 144537A1].

[0047] (2) The monomer 2-tributyltinthiophene was prepared according to the method disclosed in literature [Synthetic Metals 2006, 156(2-4), 166-175].

[0048] (3) Preparation of monomer 2,6-(bis-2-thienyl)-N,N'-diisooctyl-1,4,5,8-naphthodiimide

[0049] Take monomer 2,6-dibromo-N,N'-diisooctyl-1,4,5,8-naphthodiimide 1.944g (3mmol) into a 100mL two-necked bottle with a stirring bar , after 10 minutes of blowing nitrogen, take 40mL of clean toluene and add it to the reaction flask, stir and dissolve, under the protection of nitrogen, add 2.5g (6.1mmol) of thiophene tributyltin, and then add the catalyst tetraphen...

Embodiment 2

[0053] Preparation of 2,7-bis(trimethylene borate)-9,9'-bis(N,N-diethylhexyl-6-amino)fluorene (abbreviated as F6N)

[0054] The chemical reaction process is as follows, and the specific reaction steps and reaction conditions are as follows:

[0055]

[0056] Monomers 5 and 6 were prepared according to the method disclosed in literature [Adv. Mater., 2011, 23, 1665].

Embodiment 3

[0058] Preparation of 2,7-bis(trimethylene borate)-9,9'-bis(N,N-dimethylpropyl-3-amino)fluorene (abbreviated as F3N)

[0059] The chemical reaction process is as follows, and the specific reaction steps and reaction conditions are as follows:

[0060]

[0061] Monomers 7 and 8 were prepared according to the methods disclosed in literature [J.Am.Chem.Soc.2004, 126, 9845-9853].

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Abstract

The invention discloses an n-type water-alcohol-soluble conjugated polymer material containing a naphthodiimide ring and its application. It has the following structure, in which Ar is an aromatic group; A and B are hydrogen atoms or water-alcohol solubility. Strong polar group, and at least one of A and B is a water-alcohol-soluble strong polar group; the π unit is benzene, naphthalene, thiophene, thiophene, selenophene, tellurophene, furan, pyrrole, silole , thiazole, oxazole, triazole or other conjugated units containing carbon-carbon double bonds and carbon-nitrogen bonds; the m is an integer from 0 to 3; the 0<x<1, 0<y<1, x+ y=1; n is a natural number from 1 to 10,000. The material can be used as an electron transport layer with good charge transport capability in optoelectronic devices such as luminescence and photovoltaics to improve the processing technology and performance of the device.

Description

technical field [0001] The invention belongs to the field of optoelectronic technology, and specifically relates to a class of n-type hydroalcohol-soluble conjugated polymer materials containing naphthalene diimide and its application as an electron transport layer in optoelectronic devices. Background technique [0002] Organic photoelectric materials and devices are very suitable for industrial production and promotion due to their easy-to-obtain materials, low-temperature solvent processing, good mechanical properties, and large-area preparation, and have very broad commercialization prospects. Since 1987, Deng Qingyun's research group [Tang, C.W.; Van Slyke S.A. et al.; Applied Physics Letters, 1987,51,913.] of Kodak Company of the United States proposed organic small molecule thin film electroluminescent devices and in 1990, the R.H.Friend research group of Cambridge University in the United Kingdom [Burroughes J.H., Bradley D.C., Brown A.R., et al. Nature, 1990, 347:53...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C08G61/12H01L51/00H01L51/46H10K99/00
CPCY02E10/549Y02P70/50
Inventor 黄飞吴志鸿孙辰曹镛
Owner SOUTH CHINA UNIV OF TECH
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