Synthetic method of fused heteroaromatic compound and fused heteroaromatic compound and intermediate therefor

Patent metadata

Field	Value
Publication number	US-9932357-B2
Application number	US-201615332186-A
Country	US
Kind code	B2
Filing date	Oct 24, 2016
Priority date	Jun 14, 2016
Publication date	Apr 3, 2018
Grant date	Apr 3, 2018

Abstract

A synthetic method of a fused heteroaromatic compound includes preparing a first intermediate represented by Chemical Formula 1, obtaining a second intermediate by reacting the first intermediate and an aldehyde compound, obtain a third intermediate by performing deprotection and reduction reactions on the second intermediate, and obtaining a fused heteroaromatic compound by performing a cyclization reaction on the third intermediate.

First claim

What is claimed is:

1. A synthetic method of a fused heteroaromatic compound, comprising:
preparing a first intermediate represented by Chemical Formula 1;
reacting the first intermediate with an aldehyde compound represented by Chemical Formula 2 or 3 to obtain a second intermediate represented by Chemical Formula 4 or 5;
substituting Y1 in Chemical Formula 4 or 5 with a cyano group by reacting the second intermediate with a metal cyanide to obtain a nitrile compound;
performing deprotection and reduction reactions on the nitrile compound to obtain a third intermediate represented by one of Chemical Formula 6a to 6d; and
performing a cyclization reaction on the third intermediate by supplying an acidic catalyst to obtain a fused heteroaromatic compound having an unsubstituted terminal end,

wherein, in Chemical Formula 1,
X 1 is Se, or Te,
Y 1 is hydrogen or a halogen, and
R is a protective group, the protective group including a substituted or unsubstituted silyl group,

wherein, in Chemical Formulae 2 to 5,
X1 is Se, or Te,
Ar is one of benzene, thiophene, selenophene, tellurophene, furan, pyrrole, and a fused ring of the foregoing two or more rings,
each of Y 1 and Y 2 is hydrogen or halogen, provided that one of Y 1 and Y 2 is a halogen and the other of Y 1 and Y 2 is hydrogen,
each of Z 1 and Z 2 are hydrogen or a hydroxy group, and
R is a substituted or unsubstituted silyl group.

2. The synthetic method of claim 1 , wherein the protective group is a trimethylsilyl group, a triethylsilyl group, an isopropyldimethylsilyl group, a diethylisopropylsilyl group, a t-butyldimethylsilyl group, a t-butyldiphenylsilyl group, or a triisopropylsilyl group.

3. The synthetic method of claim 1 , wherein the performing the deprotection and reduction reactions includes performing the deprotection reaction using a fluorine-containing compound, the fluorine-containing compound including at least one of tetrabutylammonium fluoride, triethylamine trihydrofluoride, hydrofluoric acid, tris(dimethylamino)sulfonium difluorotrimethylsilicate, or ammonium fluoride.

4. The synthetic method of claim 1 , wherein the fused heteroaromatic compound is represented by Chemical Formula 7 or 8:

wherein, in Chemical Formulae 7 and 8,
Ar is one of a substituted or unsubstituted aromatic ring, a substituted or unsubstituted heteroaromatic ring, and a fused ring of the foregoing two or more rings, and
X 1 is O, S, Se, or Te.

Assignees

• Samsung Electronics Co Ltd

Inventors

• Lee Don-Wook
• Park Jeong Il
• Miyazaki Eigo

Classifications

• C07D517/22 Primary

  in which the condensed system contains four or more hetero rings · CPC title

• C07D495/04

  Ortho-condensed systems · CPC title

• H01L51/0558

  Electricity · mapped topic

• H01L51/0071

  Electricity · mapped topic

• C07D495/22 Primary

  in which the condensed system contains four or more hetero rings · CPC title