Organic semiconductor material containing naphtho-dithiadiazole and naphthalene tetracarboxylic diimide, preparation method and application of organic semiconductor material
A naphthalene tetracarboxylic acid diimide, organic semiconductor technology, applied in the field of organic semiconductor materials and their preparation, can solve the problems of low conversion efficiency and the like
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[0062] see figure 1 , a method for preparing an organic semiconductor material containing naphthobisthiadiazole and naphthalenetetracarboxylic diimide, comprising the steps of:
[0063] Step S101, provide compound A and compound B, the structural formula of compound A is:
[0064]
[0065] Among them, R 1 for C 1 ~C 20 The alkyl group or the following structural unit:
[0066]
[0067] Among them, R 2 , R 3 , R 4 for H, C 1 ~C 20 Alkyl or C 1 ~C 20 of alkoxy. R 2 , R 3 , R 4 Can be the same or different. C above 1 ~C 20 The alkyl group is C 1 ~C 20 straight chain alkyl or C 1 ~C 20 branched chain alkyl. C 1 ~C 20 The alkoxy group is C 1 ~C 20 Linear alkoxy or C 1 ~C 20 branched chain alkoxy.
[0068] Compound A can be obtained from commercial purchase or preparation. Preferably, compound A can be prepared by the following method:
[0069] Provide compound C and compound D, described compound C has following structure:
[0070]
[0071] ...
Embodiment 1
[0106] Poly(N,N′-di-octyl-1,4,5,8-naphthalene tetracarboxylic acid diimide-3,7-bis(4-ethylthiophen-5-yl)-naphtho[1, Preparation of 2-c:5,6-c]bis[1,2,5]thiadiazole
[0107] (1) Preparation of N,N'-dioctyl-2,6-dibromo-1,4,5,8-naphthalene tetracarboxylic acid diimide (compound A).
[0108] Compound C and compound D are provided, compound C is 2,6-dibromo-1,4,5,8-naphthalene dianhydride, and compound D is n-octylamine (C 8 h 17 NH 2 ).
[0109] Under nitrogen protection, n-octylamine (compound D) (0.13 g, 1 mmol) was added to propionic acid containing 2,6-dibromo-1,4,5,8-naphthalene dianhydride (0.43 g, 0.1 mmol) (15 mL) solution, reflux at 141°C for 12 hours. After cooling to room temperature, the reaction solution was poured into 10 mol / L sodium hydroxide aqueous solution, and extracted with chloroform. The organic solvent was removed, washed with ethyl acetate, dissolved in chloroform, and then subjected to column chromatography with an alumina column. The solvent was re...
Embodiment 2
[0123] Poly(N,N′-bis-((1-octylnonyl))-1,4,5,8-naphthalene tetracarboxylic acid imide-4,8-bis(thiophen-2-yl)benzo[ Preparation of 1,2-c;4,5-c′]bis-[1,2,5]thiadiazole
[0124] (1) Preparation of N,N'-bis-(1-octylnonyl)-2,6-dibromo-1,4,5,8-naphthalene tetracarboxylic acid imide (Compound A)
[0125] Provide compound C and compound D, compound C is 2,6-dibromo-1,4,5,8-naphthalene dianhydride, compound D is 1-octyl-nonylamine;
[0126] Under nitrogen protection, 1-octyl-nonylamine (compound D) (0.255 g, 1 mmol) was added to 2,6-dibromo-1,4,5,8-naphthalene dianhydride (compound C) ( 0.43g, 0.1mmol) in propionic acid (15mL) solution, reflux at 141°C for 14 hours. After cooling to room temperature, the reaction solution was poured into 10 mol / L sodium hydroxide aqueous solution, and extracted with chloroform. The organic solvent was removed, washed with ethyl acetate, dissolved in chloroform, and then subjected to column chromatography with an alumina column. The solvent was remov...
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