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

Patent metadata

Field	Value
Publication number	US-10600973-B2
Application number	US-201816033574-A
Country	US
Kind code	B2
Filing date	Jul 12, 2018
Priority date	Apr 8, 2016
Publication date	Mar 24, 2020
Grant date	Mar 24, 2020

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. An intermediate represented by Chemical Formula 3b:

wherein, in Chemical Formula 3b,
each of Ar 1 and Ar 2 are independently a substituted or unsubstituted aromatic ring,
each of Ar 3 and Ar 4 are independently a substituted or unsubstituted heteroaromatic ring,
X 1 is a chalcogen element,
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,
Z is one of an ethene group and an ethyne group,
Y 1 is a halogen, and
Y 1 and X 1 are bonded to β-carbon positions in Ar 1 and Ar 2 , respectively, that are adjacent to Z.

2. The intermediate of claim 1 , wherein
the Ar 1 and Ar 2 groups are independently a phenyl group, a naphthyl group, an anthracenyl group, a tetracenyl group, or a pentacenyl group, and
the Ar 3 and Ar 4 groups are independently a thiophenyl group, a selenophenyl group, a tellurophenyl group, a furanyl group, or a pyrrolyl group.

3. The intermediate of claim 1 , wherein in Chemical Formula 3b,
Y 1 is a bromine,
Z is an ethyne group,
each of Ar 1 and Ar 2 are independently a naphthyl group, an anthracenyl group, a tetracenyl group, or a pentacenyl group,
each Ar 3 and Ar 4 are 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,
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.

4. The intermediate of claim 2 , wherein the Ar 3 and Ar 4 groups are a thiophenyl group.

5. The intermediate of claim 2 , wherein the Ar 3 and Ar 4 groups are a selenophenyl group.

6. The intermediate of claim 2 , wherein the Ar 3 and Ar 4 groups are a tellurophenyl group.

7. The intermediate of claim 2 , wherein the Ar 3 and Ar 4 groups are a furanyl group.

8. The intermediate of claim 2 , wherein the Ar 3 and Ar 4 groups are a pyrrolyl group.

9. The intermediate of claim 2 , wherein the Z is an ethene group.

10. The intermediate of claim 2 , wherein the Z is an ethyne group.

11. The intermediate of claim 3 , wherein the X 1 is S.

12. The intermediate of claim 11 , wherein the R 1 is a methyl group.

Assignees

• Samsung Electronics Co Ltd

Inventors

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

Classifications

• C07D517/22

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

• C09K11/06

  containing organic luminescent materials · CPC title

• C07D517/04

  Ortho-condensed systems · CPC title

• C07D345/00

  Heterocyclic compounds containing rings having selenium or tellurium atoms as the only ring hetero atoms · CPC title

• C07D495/22 Primary

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