Synthetic method of fused heteroaromatic compound and fused heteroaromatic compound, and intermediate thereof

Patent metadata

Field	Value
Publication number	US-10056563-B2
Application number	US-201615392816-A
Country	US
Kind code	B2
Filing date	Dec 28, 2016
Priority date	Apr 8, 2016
Publication date	Aug 21, 2018
Grant date	Aug 21, 2018

Abstract

A method of synthesizing a fused heteroaromatic compound includes obtaining a first intermediate from a first compound represented by Chemical Formula 1 and a second compound represented by Chemical Formula 2, obtaining a second intermediate including a ring having a chalcogen element from the first intermediate, and obtaining a fused heteroaromatic compound by a cyclization reaction of the second intermediate.

First claim

What is claimed is:

1. A method of synthesizing a fused heteroaromatic compound, the method comprising:
obtaining a first intermediate by reaction of a first compound represented by Chemical Formula 1 and a second compound represented by Chemical Formula 2;
obtaining a second intermediate including a chalcogen-containing ring by reaction of the first intermediate; and
obtaining a fused heteroaromatic compound by a cyclization reaction of the second intermediate:

wherein, in Chemical Formula 1 or 2,
each of Ar 1 and Ar 2 are independently one of a substituted or unsubstituted aromatic ring, a substituted or unsubstituted heteroaromatic ring, and a fused ring of two or more rings therefrom,
X 1 is a chalcogen element,
each of R 1 and R 2 are independently one of hydrogen, a substituted or unsubstituted C 1 to C 20 alkyl group, a C 1 to C 20 fluoroalkyl group, a substituted or unsubstituted C 6 to C 20 aryl group, a halogen, and a combination thereof,
L 1 is one of an ethenyl group and an ethynyl group, and
Y 1 is a halogen,
wherein the first intermediate is represented by Chemical Formula 3:

wherein, in Chemical Formula 3,
each of Ar 1 and Ar 2 are independently one of a substituted or unsubstituted aromatic ring, a substituted or unsubstituted heteroaromatic ring, and a fused ring of two or more rings therefrom,
X 1 is a chalcogen element,
R 1 is independently one of hydrogen, a substituted or unsubstituted C 1 to C 20 alkyl group, a C 1 to C 20 fluoroalkyl group, a substituted or unsubstituted C 6 to C 20 aryl group, a halogen, and a combination thereof,
Z is one of an ethene group and an ethyne group, and
Y 1 is a halogen,
the second intermediate is represented by Chemical Formula 4:

wherein, in Chemical Formula 4,
each of Ar 1 and Ar 2 are independently one of a substituted or unsubstituted aromatic ring, a substituted or unsubstituted heteroaromatic ring, and a fused ring of two or more rings therefrom,
X 1 is a chalcogen element, and
each of Y 1 and Y 2 are independently a halogen, and
the fused heteroaromatic compound is represented by Chemical Formula 5:

wherein, in Chemical Formula 5,
each of Ar 1 and Ar 2 are independently one of a substituted or unsubstituted aromatic ring, a substituted or unsubstituted heteroaromatic ring, and a fused ring of two or more rings therefrom, and
each of X 1 and X 2 are independently a chalcogen element.

2. The method of claim 1 , wherein the obtaining a first intermediate by reaction of the first compound and the second compound is performed in the presence of a halogen salt.

3. The method of claim 2 , wherein the obtaining a first intermediate by reaction of the first compound and the second compound is performed in the presence of a one of potassium iodide, copper iodide, and a combination thereof.

4. The method of claim 1 , wherein the first compound is represented by Chemical Formula 1a:

wherein, in Chemical Formula 1a,
Ar 1 is one of a substituted or unsubstituted aromatic ring, a substituted or unsubstituted heteroaromatic ring, and a fused ring of two or more rings therefrom,
X 1 is a chalcogen element,
each of R 1 and R 3 to R 7 are independently one of hydrogen, a substituted or unsubstituted C 1 to C 20 alkyl group, a C 1 to C 20 fluoroalkyl group, a substituted or unsubstituted C 6 to C 20 aryl group, a halogen, and a combination thereof,
n is 0, 1, or 2, and
m is an integer ranging from 0 to 10.

5. The method of claim 1 , wherein the first compound is represented by Chemical Formula 1aa:

wherein, in Chemical Formula 1aa,
Ar 1 is one of a substituted or unsubstituted aromatic ring, a substituted or unsubstituted heteroaromatic ring, and a fused ring of two or more rings therefrom,
X 1 is a chalcogen element, and
R 1 is one of hydrogen, a substituted or unsubstituted C 1 to C 20 alkyl group, a C 1 to C 20 fluoroalkyl group, a substituted or unsubstituted C 6 to C 20 aryl group, a halogen, and a combination thereof.

6. The method of claim 1 , wherein the obtaining a second intermediate by reaction of the first intermediate is performed in the presence of a halogen molecule.

7. The method of claim 1 , wherein the obtaining a fused heteroaromatic compound is performed in the presence of a chalcogen element.

8. The method of claim 1 , wherein the Ar 1 and Ar 2 groups are independently one of a phenyl group, a naphthyl group, an anthracenyl group, a tetracenyl group, a pentacenyl group, a thiophenyl group, a selenophenyl group, a tellurophenyl group, a furanyl group, a pyrrolyl group, and a fused ring of two or more rings therefrom.

9. A method of synthesizing an intermediate, the method comprising:
obtaining an intermediate represented by Chemical Formula 3 by reaction of a first compound represented by Chemical Formula 1 and a second compound represented by Chemical Formula 2:

wherein, in Chemical Formula 1 or 2,
each of Ar 1 and Ar 2 are independently one of a substituted or unsubstituted aromatic ring, a substituted or unsubstituted heteroaromatic ring, and a fused ring of two or more rings therefrom,
X 1 is a chalcogen element,
each of R 1 and R 2 are independently one of hydrogen, a substituted or unsubstituted C 1 to C 20 alkyl group, a C 1 to C 20 fluoroalkyl group, a substituted or unsubstituted C 6 to C 20 aryl group, a halogen, and a combination thereof,
L 1 is one of an ethenyl group and an ethynyl group, and
Y 1 is a halogen,

wherein, in Chemical Formula 3,
each of Ar 1 and Ar 2 are independently one of a substituted or unsubstituted aromatic ring, a substituted or unsubstituted heteroaromatic ring, and a fused ring of two or more rings therefrom,
X 1 is a chalcogen element,
R 1 is independently one of hydrogen, a substituted or unsubstituted C 1 to C 20 alkyl group, a C 1 to C 20 fluoroalkyl group, a substituted or unsubstituted C 6 to C 20 aryl group, a halogen, and a combination thereof,
Z is one of an ethene group and an ethyne group, and
Y 1 is a halogen.

10. A method of synthesizing an intermediate, the method comprising:
obtaining a first intermediate represented by Chemical Formula 3 by reaction of a first compound represented by Chemical Formula 1 and a second compound represented by Chemical Formula 2; and
obtaining a second intermediate represented by Chemical Formula 4 by reaction of the first intermediate and a halogen molecule:

wherein,

Assignees

• Samsung Electronics Co Ltd

Inventors

• Miyazaki Eigo
• Park Jeong Il
• Kang Hyun Bum
• Lee Eun Kyung

Classifications

• C09K11/06

  containing organic luminescent materials · CPC title

• C07D517/22

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

• C07D517/04

  Ortho-condensed systems · CPC title

• C07D495/22 Primary

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

• C07D495/04

  Ortho-condensed systems · CPC title