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

A naphthodiimide ring and conjugated polymer technology, applied in the electron transport layer, in the field of n-type water-alcohol-soluble conjugated polymer materials, can solve the problem of relatively harsh device processing technology and electron migration Low efficiency and other problems, to achieve the effect of improving processing technology and performance, and excellent electron transmission performance

Active Publication Date: 2015-06-24
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 and alcohol soluble conjugated polymer material containing naphtho-diamide ring, and preparation method and application of material
  • N-type water and alcohol soluble conjugated polymer material containing naphtho-diamide ring, and preparation method and application of material
  • N-type water and alcohol soluble conjugated polymer material containing naphtho-diamide ring, and preparation method and application of material

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0042] Preparation of 2,6-(bis-5-bromo-2-thienyl)-N,N'-diisooctyl-1,4,5,8-naphthodiimide (abbreviated as DBrNDITEH)

[0043] The chemical reaction process is as follows, and the specific reaction steps and reaction conditions are as follows:

[0044]

[0045] (1) Monomers 1 and 2 are prepared according to the method disclosed in the patent [PCT WO2011 / 144537A1].

[0046] (2) The monomer 2-tributyltinthiophene was prepared according to the method disclosed in literature [Synthetic Metals 2006, 156(2-4), 166-175].

[0047] (3) Preparation of monomer 2,6-(bis-2-thienyl)-N,N'-diisooctyl-1,4,5,8-naphthodiimide

[0048] 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

[0052] Preparation of 2,7-bis(trimethylene borate)-9,9'-bis(N,N-diethylhexyl-6-amino)fluorene (abbreviated as F6N)

[0053] The chemical reaction process is as follows, and the specific reaction steps and reaction conditions are as follows:

[0054]

[0055] Monomers 5 and 6 were prepared according to the method disclosed in literature [Adv. Mater., 2011, 23, 1665].

Embodiment 3

[0057] Preparation of 2,7-bis(trimethylene borate)-9,9'-bis(N,N-dimethylpropyl-3-amino)fluorene (abbreviated as F3N)

[0058] The chemical reaction process is as follows, and the specific reaction steps and reaction conditions are as follows:

[0059]

[0060] 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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PUM

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Abstract

The invention discloses an n-type water and alcohol soluble conjugated polymer material containing a naphtho-diamide ring, and an application of the material. The material is in the following structure as shown in the description, wherein Ar is an aromatic group; A and B are hydrogen atoms or water and alcohol soluble strong polar groups; at least one of A and B is the water and alcohol soluble strong polar group; pi units are benzene, naphthalene, thiophene, bithiophene, selenophene, tellurophene, furan, pyrrole, silole, thiazole, oxazole, triazole or other conjugated units containing carbon-carbon double bonds and carbon-nitrogen bonds; m is an integer of 0 to 3; x is greater than 0 and less than 1; y is greater than 0 and less than 1; x plus y is equal to 1; and n is a natural number of 1 to 10000. The material can serve as an electron transfer layer with good charge transfer capability to be applied to luminous and photovoltaic photoconducting devices, etc., and a processing technology and the performance of the devices are improved.

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