Reaction products of stannyl derivatives of naphthalene diimides with rylenes

A composition and compound technology, applied in applications, inks, electrical components, etc., can solve the problems of difficult to separate dibrominated mixtures, impractical, and difficult to obtain metallizing reagents, and achieve the effect of improving solid filling

Inactive Publication Date: 2016-12-14
INST OF CHEM CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In particular, metallation reagents such as stannanes are difficult to obtain for electron-poor-(acceptor) building blocks
In addition, mono-brominated NDIs, which are available for a complete set of NDI-derived compounds, can usually only be obtained by utilizing equivalents of brominating reagents and / or by utilizing alternate reaction conditions; however, it is difficult to separate the non-brominated, mono-brominated Brominated and dibrominated mixtures that make large-scale production difficult or impractical

Method used

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  • Reaction products of stannyl derivatives of naphthalene diimides with rylenes
  • Reaction products of stannyl derivatives of naphthalene diimides with rylenes
  • Reaction products of stannyl derivatives of naphthalene diimides with rylenes

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Experimental program
Comparison scheme
Effect test

Embodiment

[0159] Additional specific embodiments are provided below without limitation.

[0160] PART I.

Embodiment A-1

[0161] Embodiment A-1 prepares compound 3,4

[0162] Scheme 1. Preparation of stannyl NDI derivatives.

[0163]

[0164] N,N'-bis(n-hexyl)-2-tris-(n-butyl)stannylnaphthalene-1,4,5,8-bis(dicarboximide), 3, and N,N' -bis(n-hexyl)-2,6-bis(tri(n-butyl)stannyl)naphthalene-1,4,5,8-bis(dicarboximide), 4, according to scheme 1 with moderate The yield is obtained. A mixture of suitable mono- or dibrominated derivatives, 1 or 2, and hexabutylditin (1 equivalent per brominated substituent) in toluene on Pd 2 dba 3 (0.05 equiv per bromide) and P(o-tol) 3 (0.2 equivalent per bromide) was heated. The reaction products were purified by silica gel chromatography and recrystallization from methanol to provide mono- and stannyl derivatives as long yellow needles; these compounds were analyzed by NMR spectroscopy, mass spectroscopy, elemental analysis and, in In the case of compound 4, the crystal X-ray structure was characterized.

[0165] Under the same conditions, in comparison, mon...

Embodiment A-2

[0167] Embodiment A-2 replaces preparation method; The synthesis of 5 and 6

[0168] Scheme 2. Preparation of stannyl NDI derivatives from commercially available NDA.

[0169]

[0170] Compounds 3 and 4 have different chromatographic properties (3: Rf = 0.3 on silica, eluting with 1:1 dichloromethane / hexane; 4: Rf = 0.3 on silica, using 1:10 dichloromethane / hexane elution), it is recommended to use a mixture of mono- and dibromo species for this reaction, which comes from the bromination and imylation of NDA and is only purified in the final stage. It is even possible to carry out these transformations without isolation of the mono- and di-functionalized intermediates, to obtain isolated yields of the mono- and stannyl derivatives of approximately 20% and 5%, respectively (e.g., when using 1eq.DBI said brominating agent).

[0171] The relative yields can be adjusted according to the brominating agent, about 10% yields were obtained for using 2.1 eq. of DBI mono- and di-s...

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Abstract

NDI-tin compounds react with rylene compounds to form NDI-rylene compounds. The rylene compound may be a perylene compound. NDI-rylene compounds can be used in organic electronic devices, including field effect transistors.

Description

technical field [0001] The present invention relates to compositions and compounds, methods of making them, methods of using them, inks and devices comprising these compositions and compounds. The composition comprises at least one naphthalene diimide (NDI) compound containing at least one stannyl substituent bonded to the naphthalene moiety of the NDI compound. Background technique [0002] Organic electronics are an important area of ​​commercial development and include, for example, advanced transistors, displays, light devices, photovoltaic devices, and sensing devices. The wide diversity of organic compounds and materials offers advantages for use in organic electronic devices. An example of the multifaceted chemistry and materials science that can be adapted for organic electronic devices is rylene (rylene) tetracarboxylic diimide derivatives, in particular, naphthalene and perylene (NDIs and PDIs, respectively) represent Almost the most widely studied category of fu...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D471/22C07D519/00C09D11/03C09D11/38H01L51/00
Inventor 王朝晖岳晚
Owner INST OF CHEM CHINESE ACAD OF SCI
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