Compound and thin film transistor and electronic device

Patent metadata

Field	Value
Publication number	US-11066418-B2
Application number	US-201916693715-A
Country	US
Kind code	B2
Filing date	Nov 25, 2019
Priority date	Nov 26, 2018
Publication date	Jul 20, 2021
Grant date	Jul 20, 2021

Abstract

Disclosed are a compound represented by Chemical Formula 1A or 1B, an organic thin film, a thin film transistor, and an electronic device.

In Chemical Formulae 1A and 1B, X 1 , Ar 1 , R 1 to R 4 , and n 1 are the same as described in the detailed description.

First claim

What is claimed is:

1. A compound represented by Chemical Formula 1A or 1B:

wherein, in Chemical Formulae 1A and 1B,
X 1 is O, S, Se, or Te,
R 1 to R 4 are each independently hydrogen, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C2 to C30 alkenyl group, a substituted or unsubstituted C2 to C30 alkynyl group, a substituted or unsubstituted C1 to C30 alkoxy group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C6 to C30 aryloxy group, a substituted or unsubstituted C3 to C30 heteroaryl group, a halogen, a cyano group, or a combination thereof, and
n 1 is 1,
Ar 1 is one of substituted or unsubstituted rings listed in Group 1-1:

wherein, in Group 1-1,
Y 1 and Y 2 are each independently one of O, S, Se, and Te, and
* is a linking point with Chemical Formula 1A or 1B.

2. The compound of claim 1 , wherein
X 1 is different from Y 1 and Y 2 .

3. The compound of claim 2 , wherein
X 1 is Se or Te, and
Y 1 and Y 2 are S.

4. The compound of claim 1 , wherein
R 1 and R 2 are different from each other.

5. The compound of claim 4 , wherein
one of R 1 and R 2 is hydrogen.

6. The compound of claim 4 , wherein
one of R 1 and R 2 is a substituted or unsubstituted C1 to C30 linear alkyl group, a substituted or unsubstituted C2 to C30 linear alkenyl group, a substituted or unsubstituted C2 to C30 linear alkynyl group, a substituted or unsubstituted C1 to C30 alkoxy group, or a combination thereof,
the other of R 1 and R 2 is a substituted or unsubstituted C3 to C30 branched alkyl group, a substituted or unsubstituted C4 to C30 branched alkenyl group, a substituted or unsubstituted C4 to C30 branched alkynyl group, or a combination thereof.

7. The compound of claim 4 , wherein
one of R 1 and R 2 is a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C2 to C30 alkenyl group, a substituted or unsubstituted C2 to C30 alkynyl group, a substituted or unsubstituted C1 to C30 alkoxy group, or a combination thereof,
the other of R 1 and R 2 is a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C6 to C30 aryloxy group, a substituted or unsubstituted C3 to C30 heteroaryl group, or a combination thereof.

8. An organic thin film comprising the compound of claim 1 .

9. A thin film transistor comprising
a gate electrode,
an organic semiconductor overlapping with the gate electrode, and
a source electrode and a drain electrode electrically connected to the organic semiconductor, wherein the organic semiconductor comprises a compound represented by Chemical Formula 1A or 1B:

wherein, in Chemical Formulae 1A and 1B,
X 1 is O, S, Se, or Te,
R 1 to R 4 are each independently hydrogen, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C2 to C30 alkenyl group, a substituted or unsubstituted C2 to C30 alkynyl group, a substituted or unsubstituted C1 to C30 alkoxy group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C6 to C30 aryloxy group, a substituted or unsubstituted C3 to C30 heteroaryl group, a halogen, a cyano group, or a combination thereof, and
n 1 is 1,
Ar 1 is one of substituted or unsubstituted rings listed in Group 1-1:

wherein, in Group 1-1,
Y 1 and Y 2 are each independently one of O, S, Se, and Te, and
* is a linking point with Chemical Formula 1A or 1B.

10. The thin film transistor of claim 9 , wherein
X 1 is different from Y 1 and Y 2 .

11. The thin film transistor of claim 10 , wherein
X 1 is Se or Te, and
Y 1 and Y 2 are S.

12. The thin film transistor of claim 9 , wherein
R 1 and R 2 are different from each other.

13. The thin film transistor of claim 12 , wherein
one of R 1 and R 2 is hydrogen.

14. The thin film transistor of claim 12 , wherein
one of R 1 and R 2 is a substituted or unsubstituted C1 to C30 linear alkyl group, a substituted or unsubstituted C2 to C30 linear alkenyl group, a substituted or unsubstituted C2 to C30 linear alkynyl group, a substituted or unsubstituted C1 to C30 alkoxy group, or a combination thereof,
the other of R 1 and R 2 is a substituted or unsubstituted C1 to C30 branched alkyl group, a substituted or unsubstituted C4 to C30 branched alkenyl group, a substituted or unsubstituted C4 to C30 branched alkynyl group, or a combination thereof.

15. The thin film transistor of claim 12 , wherein
one of R 1 and R 2 is a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C2 to C30 alkenyl group, a substituted or unsubstituted C2 to C30 alkynyl group, a substituted or unsubstituted C1 to C30 alkoxy group, or a combination thereof, and
the other of R 1 and R 2 is a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C6 to C30 aryloxy group, a substituted or unsubstituted C3 to C30 heteroaryl group, or a combination thereof.

16. An electronic device comprising the organic thin film of claim 8 .

17. An electronic device comprising the thin film transistor of claim 9 .

Assignees

• Samsung Electronics Co Ltd

Inventors

• Lee Don-Wook
• Park Jeong Il
• Lee Eun Kyung

Classifications

• C07D495/04

  Ortho-condensed systems · CPC title

• C07D517/04 Primary

  Ortho-condensed systems · CPC title

• C07D517/22 Primary

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

• H01L51/0071

  Electricity · mapped topic

• H01L51/0558

  Electricity · mapped topic