Polymer semiconductors, stretchable polymer thin films, and electronic devices

Patent metadata

Field	Value
Publication number	US-11737346-B2
Application number	US-202217745155-A
Country	US
Kind code	B2
Filing date	May 16, 2022
Priority date	May 27, 2021
Publication date	Aug 22, 2023
Grant date	Aug 22, 2023

Abstract

Provided are a polymer semiconductor including a first structural unit represented by Chemical Formula 1 and a second structural unit represented by Chemical Formula 2, a stretchable polymer thin film including the same, and an electronic device.

Definitions of Chemical Formulas 1 and 2 are as described in the detailed description.

First claim

What is claimed is:

1. A polymer semiconductor, comprising:
a first structural unit represented by Chemical Formula 1 and a second structural unit represented by Chemical Formula 2:

wherein, in Chemical Formula 1,
R 11 and R 12 are each independently hydrogen, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C1 to C30 alkoxy group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C2 to C30 heteroaryl group, —COR a , —OC(═O)R b , —C(═O)OR b , —OC(═O)OR d , a halogen, a cyano group, or any combination thereof, wherein R a to R d are each independently hydrogen, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C1 to C30 alkoxy group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C2 to C30 heteroaryl group, a halogen, a cyano group, or any combination thereof,
L 1 and L 2 are each independently a single bond, a substituted or unsubstituted C6 to C30 arylene group, a substituted or unsubstituted divalent C3 to C30 heterocyclic group, fused rings thereof, or any combination thereof, and
D 1 is a substituted or unsubstituted C6 to C30 arylene group; a substituted or unsubstituted divalent C3 to C30 heterocyclic group including at least one of N, O, S, Se, Te, or Si; fused rings thereof, or any combination thereof,

wherein, in Chemical Formula 2,
R 21 , R 22 , R 23 , and R 24 are each independently hydrogen, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C1 to C30 alkoxy group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C2 to C30 heteroaryl group, —COR a , —OC(═O)R b , —C(═O)OR b , —OC(═O)OR d , a halogen, a cyano group, or any combination thereof, wherein R a to R d are each independently hydrogen, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C1 to C30 alkoxy group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C2 to C30 heteroaryl group, a halogen, a cyano group, or any combination thereof,
X 1 and X 2 are each independently S, Se, or Te, and
X 1 and X 2 are different from each other.

2. The polymer semiconductor of claim 1 , wherein D 1 is one or more substituted or unsubstituted phenylene groups; one or more substituted or unsubstituted naphthylene groups; one or more substituted or unsubstituted anthracenylene groups; one or more substituted or unsubstituted phenanthrenylene groups; one or more substituted or unsubstituted pentagonal rings including at least one of N, O, S, Se, Te, or Si; a fused ring of two or more of the substituted or unsubstituted pentagonal rings; a fused ring of one or more substituted or unsubstituted pentagonal rings and one or more substituted or unsubstituted phenylene groups; a fused ring of one or more substituted or unsubstituted pentagonal rings and one or more substituted or unsubstituted naphthylene groups; a fused ring of one or more substituted or unsubstituted pentagonal rings and one or more substituted or unsubstituted anthracenylene groups; a fused ring of one or more substituted or unsubstituted pentagonal rings and one or more substituted or unsubstituted phenanthrenylene groups; or any combination thereof.

3. The polymer semiconductor of claim 1 , wherein in Chemical Formula 1, D 1 is one electron-donating moiety of a group of electron-donating moieties of Group 1:

wherein, in Group 1,
X 3 to X 9 and X 11 to X 18 are each independently O, S, Se, or Te,
X 10 is O, S, Se, Te, NR v , CR w R x , or SiR y R z ,
X 19 and X 20 are each independently N, CR aa , or SiR ab ,
R a to R z and R aa to R ab 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 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 C7 to C30 alkylaryl group, a substituted or unsubstituted C6 to C30 aryloxy group, a substituted or unsubstituted C3 to C30 heterocyclic group, a halogen, a cyano group, or any combination thereof,
n is 0, 1, or 2, and
* is a linking point with Chemical Formula 1.

4. The polymer semiconductor of claim 1 , wherein in Chemical Formula 1, L 1 and L 2 are each independently a single bond; one electron-donating moiety of a group of electron-donating moieties of Group 1; a substituted or unsubstituted pyridine; a substituted or unsubstituted pyrimidine; fused rings thereof; or any combination thereof:

wherein, in Group 1,
X 3 to X 9 and X 11 to X 18 are each independently O, S, Se, or Te,
X 10 is O, S, Se, Te, NR v , CR w R x , or SiR y R z ,
X 19 and X 20 are each independently N, CR aa , or SiR ab ,
R a to R z and R aa to R ab 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 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 C7 to C30 alkylaryl group, a substituted or unsubstituted C6 to C30 aryloxy group, a substituted or unsubstituted C3 to C30 heterocyclic group, a halogen, a cyano group, or any combination thereof,
n is 0, 1, or 2, and
* is a linking point with Chemical Formula 1.

5. The polymer semiconductor of claim 1 , wherein in Chemical Formula 1, L 1 and L 2 are each independently a divalent linking group including a single bond; 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; at least one substituted or unsubstituted pyrrole; at least one substituted or unsubstituted benzene; at least one substituted or unsubstituted pyridine; at least one substituted or unsubstituted pyrimidine; a fused ring of two or more thereof; or any combination thereof.

6. The polymer semiconductor of claim 1 , wherein in Chemical Formula 1, R 11 and R 12 are each independently a substituted or unsubstituted C6 to C30 linear alkyl group or a substituted or unsubstituted C6 to C30 branched alkyl group.

7. The polymer semiconductor of claim 1 , wherein in Chemical Formula 2, X 1 is S and X 2 is Se or Te.

8. The polymer semiconductor of claim 1 , wherein in Chemical Formula 2, X 1 is Se or Te and X 2 is S.

9. The polymer semiconductor of claim 1 , wherein in Chemical Formula 2, R 21 , R 22 , R 23 , and R 24 are each independently a substituted or unsubstituted C6 to C30 linear alkyl group or a substituted or uns

Assignees

• Samsung Electronics Co Ltd

Inventors

• Gam Sangah
• Chung Jong Won
• Kang Hyun Bum
• Yun Youngjun
• LEE Yeongjun

Classifications

• H10K85/113 Primary

  Heteroaromatic compounds comprising sulfur or selene, e.g. polythiophene · CPC title

• C08G61/126

  with a five-membered ring containing one sulfur atom in the ring · CPC title

• C08J5/18

  Manufacture of films or sheets · CPC title

• H01B1/121

  Charge-transfer complexes · CPC title

• H10K85/151

  Copolymers · CPC title