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Functional diamine monomers having high planarity and containing naphthaline structure and synthesis method and application thereof

A technology of diamine monomer and synthesis method, which is applied in the field of material science to achieve the effect of compact packing, easy purification and small free volume

Active Publication Date: 2015-07-01
江西有泽新材料科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the temperature characteristics (use temperature of 200°C) and barrier properties (water vapor transmission rate below 10 -6 g / m 2 / day, the oxygen transmission rate is lower than 10 -5 cm 3 / m 2 / day) is one of the key issues to be overcome to achieve flexible OLEDs, and no polymers with this property have been reported yet.

Method used

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  • Functional diamine monomers having high planarity and containing naphthaline structure and synthesis method and application thereof
  • Functional diamine monomers having high planarity and containing naphthaline structure and synthesis method and application thereof
  • Functional diamine monomers having high planarity and containing naphthaline structure and synthesis method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0039] Synthesis of 4,4'-(naphthalene-2,7-diyl)dianiline:

[0040]

[0041] Add 8.579g (0.03mol) of 2,7-dibromonaphthalene and 11.272g (0.065mol) of p-aminophenyl borate hydrochloride into a 500ml three-necked flask, add 400ml of tetrahydrofuran, and then add 2mol / L potassium carbonate solution 97.5ml and an appropriate amount of Aliquat336, magnetically stirred and argon, heated to 75°C in an oil bath, added 0.100g tetrakistriphenylphosphinepalladium, and refluxed for 24h. The reaction solution was poured into water, and a large amount of precipitates precipitated out. Suction filter with a funnel, evaporate the solvent under reduced pressure. The product was purified by column chromatography using dichloromethane as the mobile phase and silica gel as the stationary phase. The product was collected and spin-dried to obtain an orange-red solid, which was vacuum-dried at 60° C. for 24 h with a yield of 80%. The infrared spectrum of the compound is shown in figure 1 As sho...

Embodiment 2

[0043] Synthesis of Bis(4-aminobenzyl)naphthalene-2,6-dicarboxylate:

[0044]

[0045] (1) Synthetic intermediate naphthalene-2,6-dicarbonyl dichloride

[0046] 10.810g (0.050mol) of 2,6-naphthalene dicarboxylic acid was added to a 250ml three-necked flask, 100ml of dehydrated dichloromethane was added, and 17.846g (0.150mol) of thionyl chloride was slowly added dropwise under ice bath conditions. Add 3 to 4 drops of N,N-dimethylformamide dropwise as a catalyst, stir magnetically and flow argon, heat up to 75°C and reflux for 12h. The solvent and excess thionyl chloride were distilled off under reduced pressure to obtain a light yellow solid with a yield of 85%. The intermediate structure is as follows:

[0047]

[0048] (2) Synthesis of intermediate bis(4-nitrobenzyl)naphthalene-2,6-dicarboxylate:

[0049] Add 18.376g (0.12mol) of 4-nitrobenzyl alcohol into a 500ml three-necked flask, add 200ml of N,N-dimethylacetamide, 40ml of triethylamine, and slowly add the napht...

Embodiment 3

[0054] N 2 ,N 6 Synthesis of -bis(4-((4-aminophenyl)amino)phenyl)naphthalene-2,6-dicarboxami-de:

[0055]

[0056] (1) synthetic intermediate naphthalene-2,6-dicarbonyl dichloride according to Example 2;

[0057] (2) Synthetic intermediate N 2 ,N 6 -bis(4-aminophenyl)naphthalene-2,6-dicarboxamide:

[0058] Dissolve 10.814g (0.1mol) of p-phenylenediamine in a 4:1 solution of N-methylpyrrolidone and pyridine in 150ml, then slowly add 5.061g (0.02mol) of naphthalene-2,6-dicarbonyl dichloride under argon Add 12.420g (0.04mol) of triphenyl phosphite under ambient conditions, stir at room temperature for 2 hours, then raise the temperature to 100°C for 12 hours, pour the reaction solution into methanol after cooling, filter out the precipitate, wash thoroughly with methanol, - Recrystallize from dimethylformamide and water, dry in a vacuum oven at 50°C for 10 hours to obtain off-white product N 2 ,N 6 -bis(4-aminophenyl)naphthalene-2,6-dicarboxamide 6.739 g, yield 85%. Th...

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Abstract

The invention discloses functional diamine monomers having high planarity and containing a naphthaline structure and a synthesis method and application thereof. The novel functional diamine monomers are prepared from raw materials monomers such as dihalogenated naphthaline, naphthalic acid, naphthalenediol or naphthylenediamine through a series of chemical reactions such as substitution reaction, Suzuki reaction, amidation reaction, esterification reaction, Grignard reaction, Kumada coupling reaction. The diamine monomers containing a naphthaline structure, which have a lowest energy state 3D molecular structure and have high planarity, can be obtained. Due to planar space structure, the diamine monomers disclosed by the invention can serve as monomers used for preparing polymers with strong molecular chain interaction force, tight molecular chain packing and small free volume and the polymers can be endowed with an excellent barrier property. The synthesis method of the diamine monomers is simple in process and purification operation is easy; therefore, the synthesis method is suitable for industrial production. The diamine monomers disclosed by the invention can be used for synthesizing functional polymers such as polyamide, polyimide, polyamide-imide and polyester-imide.

Description

technical field [0001] The invention relates to the field of material science, in particular to a highly planar naphthalene-containing functional diamine monomer and a synthesis method thereof. The diamine monomer can be used to synthesize polyamide, polyimide, polyamide-imide High performance, functional polymers such as amines and polyesterimides. Background technique [0002] Organic electroluminescent devices (OLEDs) highlight all solid-state, active luminescence, high luminous efficiency, high brightness, high contrast, ultra-thin, low power consumption, no viewing angle limitation, fast response, wide operating temperature range, simple processing technology, With many advantages such as energy saving and environmental protection, it is considered to be an ideal and promising new-generation information display technology to replace liquid crystal displays, and it will be the focus of the development of the world's information industry in the next 30 years. Moreover, O...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C211/61C07C209/68C07C219/32C07C213/02C07C233/80C07C231/12C07C217/84
CPCC07C211/50C07C217/84C07C219/32C07C233/80C08G69/02C08G73/10C08G73/14C08G73/16C08L77/00C08L79/08
Inventor 刘亦武曾义谭井华张海良胡敏陈洪黄杰刘跃军魏珊珊
Owner 江西有泽新材料科技有限公司
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