# US 2018/0323381 A1 · Synthetic method of fused heteroaromatic compound and fused heteroaromatic compound, and intermediate thereof

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- Number: US 2018/0323381 A1
- Document ID: US20180323381A1
- Status: Published application
- Kind: A1
- Application number: 16/033,574
- Filed: 2018-07-12
- Published: 2018-11-08
- Earliest claimed: 2016-04-08
- Assignees: Samsung Electronics Co., Ltd.
- Applicants: Samsung Electronics Co., Ltd.
- Inventors: Eigo MIYAZAKI; Jeong II PARK; Hyun Bum KANG; Eun Kyung LEE
- Web page: https://patentgrep.com/patent/US20180323381A1

## CPC

- H10K 85/6576: {comprising only sulfur in the heteroaromatic polycondensed ring system, e.g. benzothiophene}
- C07D 333/74: Naphthothiophenes
- C07D 345/00: Heterocyclic compounds containing rings having selenium or tellurium atoms as the only ring hetero atoms
- C07D 495/04: Ortho-condensed systems
- C07D 495/22: in which the condensed system contains four or more hetero rings
- C07D 517/04: Ortho-condensed systems
- C07D 517/22: in which the condensed system contains four or more hetero rings
- C09K 11/06: containing organic luminescent materials
- H10K 85/657: {Polycyclic condensed heteroaromatic hydrocarbons}
- H10K 10/466: {Lateral bottom-gate IGFETs comprising only a single gate}
- H10K 10/484: {characterised by the channel regions}
- H10K: ORGANIC ELECTRIC SOLID-STATE DEVICES
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- C09K: MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE

## 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.

## Claims

### Claim at position 1

-11. (canceled)

### Claim 12

An intermediate represented by Chemical Formula 3:
wherein, in Chemical Formula 3,
each of Ar1 and Ar2 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,
X1 is a chalcogen element,
R1 is one of hydrogen, a substituted or unsubstituted C1 to C20 alkyl group, a C1 to C20 fluoroalkyl group, a substituted or unsubstituted C6 to C20 aryl group, a halogen, and a combination thereof,
Z is one of an ethene group and an ethyne group, and
Y1 is a halogen.

### Claim 13 (depends on 12)

The intermediate of claim 12, wherein the Ar1 and Ar2 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.

### Claim 14 (depends on 12)

The intermediate of claim 12, wherein the intermediate is represented by Chemical Formula 3a:
wherein, in Chemical Formula 3a,
each of Ar1 and Ar2 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,
X1 is a chalcogen element, and
R1 is one of hydrogen, a substituted or unsubstituted C1 to C20 alkyl group, a C1 to C20 fluoroalkyl group, a substituted or unsubstituted C6 to C20 aryl group, a halogen, and a combination thereof.

### Claim 15

(canceled)

### Claim 16

An intermediate represented by Chemical Formula 4:
wherein, in Chemical Formula 4,
each of Ar1 and Ar2 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,
X1 is a chalcogen element, and
each of Y1 and Y2 are independently a halogen.

### Claim 17 (depends on 16)

The intermediate of claim 16, wherein the Ar1 and Ar2 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.

### Claim 18 (depends on 16)

The intermediate of claim 16, wherein the intermediate is represented by Chemical Formula 4a:
wherein, in Chemical Formula 4a,
each of Ar1 and Ar2 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, and
X1 is a chalcogen element.

### Claim 19

-21. (canceled)