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Naphthalene diimide containing 2-(1,3-dithio/seleno-2-subunit)ethylcyanide conjugate structure unit and derivatives thereof

A naphthalene diimide, C2-C48 technology, applied in the field of organic electronic materials, can solve the problems of lack and reduction of polymerized monomers

Active Publication Date: 2014-12-24
SHANGHAI INST OF ORGANIC CHEM CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] For the development of n-type oligomers and polymer semiconductor materials, the biggest bottleneck is the lack of polymer monomers (reaction intermediates) that can effectively reduce the LUMO energy level of semiconductor materials (Li, H.Y. et al. J. Am. Chem.Soc.2013,135,14920.; Lei,T.et al.J.Am.Chem.Soc.2013,135,12168.)

Method used

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  • Naphthalene diimide containing 2-(1,3-dithio/seleno-2-subunit)ethylcyanide conjugate structure unit and derivatives thereof
  • Naphthalene diimide containing 2-(1,3-dithio/seleno-2-subunit)ethylcyanide conjugate structure unit and derivatives thereof
  • Naphthalene diimide containing 2-(1,3-dithio/seleno-2-subunit)ethylcyanide conjugate structure unit and derivatives thereof

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Experimental program
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preparation example Construction

[0217] The preparation of formula (A) compound

[0218] The present invention also provides a preparation method of a compound of formula (A), comprising the steps of:

[0219]

[0220] (a) in an inert solvent, react with a compound of formula Ia and a halogenating reagent to obtain a compound of formula I or a compound of formula II;

[0221] or include steps:

[0222]

[0223] (b) in an inert solvent, react with a compound of formula (IIIa) and a halogenating reagent to obtain a compound of formula (IIIb);

[0224] Wherein, M is CN or H, and the definitions of other groups are as described in the first aspect of the present invention.

[0225] In another preferred example, the steps are performed in air or under the protection of an inert gas.

[0226] In another preferred embodiment, the inert solvent is a chlorine-containing organic solvent, preferably selected from the group consisting of chloroform and carbon tetrachloride.

[0227] In another preferred example...

Embodiment 1

[0330] Example 1: N-(2-decyl-dodecyl)-[2,3-d:6,7-d']-bis[2-(1,3-dithio-2-ylidene) Synthesis of -2-bromoacetocyanide]-naphthalene-1,4,5,8-tetracarboxylic diimide (1)

[0331]

[0332] 1mL Br at room temperature 2 (179mg, 1.12mmol) in chloroform solution was added dropwise to N-(2-decyl-dodecyl)-[2,3-d:6,7-d′]-bis[2-(1,3 -Dithio-2-ylidene) acetocyanide]-naphthalene-1,4,5,8-tetracarboxylic diimide (568mg, 0.487mmol) in 8mL chloroform solution, react for 2h, stop the reaction, reduce pressure The solvent was distilled off, and the remaining solid was subjected to column chromatography with petroleum ether / dichloromethane (1 / 1) as eluent to obtain 594 mg of product (blue solid) with a yield of 92%. 1 HNMR (300MHz, CDCl 3 )δ(ppm):0.84–0.87(t,12H),1.22(br,80H),2.02(br,2H),4.17(br,4H); 13 C NMR (100MHz, CDCl 3 ): δ: 14.10, 22.68, 26.34, 29.36, 29.63, 29.66, 29.67, 29.70, 29.71, 30.10, 31.44, 36.49, 31.53, 31.91, 36.40, 36.44, 36.49, 46.29, 71.24, 1114.14.14, 2 124.75, 124.98,...

Embodiment 2

[0333]Example 2: N-(2-octyl-dodecyl)-[2,3-d]-[2-(1,3-dithio-2-ylidene) propanedicyanide]-[6, 7-d'][2-(1,3-dithio-2-ylidene)-2-bromoacetonitrile]-naphthalene-1,4,5,8-tetracarboxylic diimide (2) Synthesis

[0334]

[0335] The compound N-(2-octyl-dodecyl)-[2,3-d]-[2-(1,3-dithio-2-ylidene) propanedicyanide]-[6,7- d'][2-(1,3-dithio-2-ylidene)acetocyanide]-naphthalene-1,4,5,8-tetracarboxylic diimide (30mg, 0.028mmol) was dissolved in 3mL chloroform 0.16 mL of a chloroform solution (V%=0.01) containing liquid bromine (0.031 mmol) was slowly added dropwise to the above solution, and the reaction solution was refluxed and stirred for 1 hour, then cooled to room temperature, and the solvent was removed under reduced pressure, and dichloromethane / Petroleum ether (1 / 1) was used as eluent, and the crude product was separated and purified by silica gel chromatography to obtain 28 mg of compound (2), with a yield of 88%. 1 H-NMR (300MHz, CDCl 3 )δ(ppm):0.86–0.88(m,6H,–CH 3 ),1.25–1...

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Abstract

The invention provides a naphthalene diimide containing 2-(1,3-dithio / seleno-2-subunit)ethylcyanide conjugate structure unit and derivatives thereof, particularly compounds disclosed as Formula (A), wherein the groups are defined in the specification. The monomer can be used for preparing a series of polymers (dimers or polymers) with favorable device properties; and the polymers can be used for preparing organic photoelectric devices with favorable properties.

Description

technical field [0001] The invention relates to the field of organic electronic materials, specifically, the invention provides a class of electron-deficient naphthalene diimides containing 2-(1,3-disulfide / selenium-2-ylidene) acetocyanide conjugated structural units Polymerized monomers, dimer compounds (oligomers) and polymers, their preparation methods and applications. Background technique [0002] New organic electronic materials are the material basis for the development of organic electronic devices. The rapid development of organic optoelectronic devices such as organic field effect transistors and polymer solar cells urgently requires organic semiconductor materials with high mobility, high stability and easy processing. [0003] The realization of fully organic flexible electronic devices requires semiconductor materials with good film-forming properties and processability. Printed electronics (Printed electronics) technologies can be used, such as: film throwing, ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D495/22C07D495/16C07D519/00C08G61/12H01L51/00H10K99/00
CPCC07D495/16C07D495/22C07D519/00C08G61/122C08G61/126C08G2261/3243C08G2261/92H10K85/113H10K85/151H10K85/621H10K85/657H10K99/00C07D517/16C07D517/22C08G61/12Y02E10/549
Inventor 高希珂赵征胡云宾王中丽
Owner SHANGHAI INST OF ORGANIC CHEM CHINESE ACAD OF SCI
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