Compound and organic thin film and thin film transistor and electronic device

Patent metadata

Field	Value
Publication number	US-11038116-B2
Application number	US-201916531376-A
Country	US
Kind code	B2
Filing date	Aug 5, 2019
Priority date	Nov 26, 2018
Publication date	Jun 15, 2021
Grant date	Jun 15, 2021

Abstract

Disclosed are a compound represented by Chemical Formula 1A or 1B, an organic thin film including the same, a thin film transistor, and an electronic device.In Chemical Formula 1A or 1B, X1, X2, Ar1, R1 to R4, and n1 are the same as described in the detailed description.

First claim

What is claimed is:

1. A compound represented by Chemical Formula 1A:

wherein, in Chemical Formula 1A,
X 1 and X 2 are different from each other and are independently O, S, Se, Te, or NR a ,
Ar 1 is at least one substituted or unsubstituted benzene, at least one substituted or unsubstituted furan, at least one substituted or unsubstituted thiophene, at least one substituted or unsubstituted selenophene, at least one substituted or unsubstituted tellurophene, or a structure represented by a substituted or unsubstituted group listed in Group 1 :

wherein, in Group 1 , Y 1 and Y 2 are independently one of O, S, Se, and Te, and * is a linking point with Chemical Formula 1A
R 1 and R 2 are different from each other or R 3 and R 4 are different from each other,
R 1 to R 4 and R a are 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 C3 to C30 cycloalkyl group, a substituted or unsubstituted C3 to C30 cycloalkenyl group, a substituted or unsubstituted C1 to C30 alkoxy group, a substituted or unsubstituted C3 to C30 cycloheteroalkyl group, a substituted or unsubstituted C3 to C30 cycloheteroalkenyl 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.

2. The compound of claim 1 , wherein one of X 1 and X 2 is Se or Te.

3. The compound of claim 1 , wherein Ar 1 includes at least one of a substituted or unsubstituted furan, a substituted or unsubstituted thiophene, substituted or unsubstituted selenophene, and substituted or unsubstituted tellurophene.

4. The compound of claim 1 , wherein at least one of X 1 and X 2 of Chemical Formula 1A is different from Y 1 and Y 2 listed in Group 1, respectively.

5. The compound of claim 4 , wherein
one of X 1 and X 2 is Se or Te, and
Y 1 and Y 2 are independently O or S.

6. The compound of claim 1 , wherein
one of R 1 and R 2 is hydrogen, and
the other 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 C3 to C30 cycloalkyl group, a substituted or unsubstituted C3 to C30 cycloalkenyl group, a substituted or unsubstituted C1 to C30 alkoxy group, a substituted or unsubstituted C3 to C30 cycloheteroalkyl group, a substituted or unsubstituted C3 to C30 cycloheteroalkenyl 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.

7. The compound of claim 1 , 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, and
the other of R 1 and R 2 is a substituted or unsubstituted C4 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.

8. The compound of claim 1 , 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 C3 to C30 cycloalkyl group, a substituted or unsubstituted C3 to C30 cycloalkenyl group, a substituted or unsubstituted C3 to C30 cycloheteroalkyl group, a substituted or unsubstituted C3 to C30 cycloheteroalkenyl 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, or a combination thereof.

9. The compound of claim 1 , wherein
one of R 1 and R 2 is a substituted or unsubstituted C3 to C30 cycloalkyl group, a substituted or unsubstituted C3 to C30 cycloalkenyl group, a substituted or unsubstituted C6 to C30 aryl group, or a combination thereof, and
the other of R 1 and R 2 is a substituted or unsubstituted C3 to C30 cycloheteroalkyl group, a substituted or unsubstituted C3 to C30 cycloheteroalkenyl group, a substituted or unsubstituted C3 to C30 heteroaryl group, or a combination thereof.

10. The compound of claim 1 , wherein one of R 1 and R 2 includes a structure represented by one of Chemical Formulae 2A to 2C:

wherein, in Chemical Formula 2A, 2B, or 2C,
Z 1 to Z 3 are independently N or CR b ,
one of Z 1 to Z 3 is N,
X 3 is O, S, Se, Te, NR c , CR d R e , or SiR f R g ,
m1 is an integer ranging from 0 to 5,
m2 is an integer ranging from 0 to 3,
R 5 to R 9 and R b to R g are 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 C3 to C30 cycloalkyl group, a substituted or unsubstituted C3 to C30 cycloalkenyl group, a substituted or unsubstituted C1 to C30 alkoxy group, a substituted or unsubstituted C3 to C30 cycloheteroalkyl group, a substituted or unsubstituted C3 to C30 cycloheteroalkenyl 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 or a linking point with Chemical Formula 1A,
when R 5 is two or more, each R 5 is the same or different and adjacent two R 5 's are present independently or linked with each other to form a ring, and
when R 9 is two or more, each R 9 is the same or different and adjacent two R 9 's are present independently or linked with each other to form a ring.

11. The compound of claim 1 , wherein
one of X 1 and X 2 is Se or Te,
one of R 1 and R 2 is hydrogen, and
the other 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 C3 to C30 cycloalkyl group, a substituted or unsubstituted C3 to C30 cycloalkenyl group, a substituted or unsubstituted C1 to C30 alkoxy group, a substituted or unsubstituted C3 to C30 cycloheteroalkyl group, a substituted or unsubstituted C3 to C30 cycloheteroalkenyl 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.

12. The compound of claim 1 , wherein
one of X 1 and X 2 is Se or Te,
one of R 1 and R 2 is a substituted or unsubstituted C1 to C30 linear a

Assignees

• Samsung Electronics Co Ltd

Inventors

• Lee Eunkyung
• Lee Don-Wook
• Park Jeong Il

Classifications

• H10K10/40

  Organic transistors · CPC title

• H10K85/657

  Polycyclic condensed heteroaromatic hydrocarbons · CPC title

• C07D517/04 Primary

  Ortho-condensed systems · CPC title

• Y02E10/549

  Organic PV cells · CPC title

• C07D517/22

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