Fused polycyclic heteroaromatic compound and organic thin film and electronic device

Patent metadata

Field	Value
Publication number	US-11242357-B2
Application number	US-201816140661-A
Country	US
Kind code	B2
Filing date	Sep 25, 2018
Priority date	Oct 18, 2017
Publication date	Feb 8, 2022
Grant date	Feb 8, 2022

Abstract

A fused polycyclic heteroaromatic compound represented by Chemical Formula 1, and an organic thin film, an organic thin film transistor, and an electronic device including the fused polycyclic heteroaromatic compound are provided. The fused polycyclic heteroaromatic compound may have a conjugation structure but reinforce planarity among adjacent rings and have further dense packing and thus much increase charge mobility.

First claim

What is claimed is:

1. A fused polycyclic heteroaromatic compound represented by Chemical Formula 1:

wherein, in Chemical Formula 1,
X 1 and X 2 are independently O, S, Se, Te, or N—R a , wherein R a is hydrogen, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C3 to C30 cycloalkyl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C7 to C30 arylalkyl group, a substituted or unsubstituted C1 to C30 heteroalkyl group, a substituted or unsubstituted C2 to C30 heterocycloalkyl group, a substituted or unsubstituted C2 to C30 heterocyclic group, a substituted or unsubstituted C2 to C30 alkenyl group, a substituted or unsubstituted C2 to C30 alkynyl group, a hydroxy group, a halogen atom, or a combination thereof,
Ar is a substituted or unsubstituted C6 to C30 aromatic ring, a substituted or unsubstituted C3 to C30 heteroaromatic ring, or a fused ring including the fused two or more rings, Ar is combined with an X 1 -containing hetero ring and an X 2 -containing hetero ring to provide a condensed polycyclic ring,
R 1 and R 2 are independently hydrogen or a halogen atom, and
R 3 and R 4 of Chemical Formula 1 are independently one of heterocyclic groups represented by Chemical Formula 2-1 and Chemical Formula 2-2:

wherein, in Chemical Formula 2-1 and Chemical Formula 2-2,
X 3 is S, Se, or Te,
R 11 and R 12 are independently hydrogen, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C3 to C30 cycloalkyl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C7 to C30 arylalkyl group, a substituted or unsubstituted C1 to C30 heteroalkyl group, a substituted or unsubstituted C2 to C30 heterocycloalkyl group, a substituted or unsubstituted C2 to C30 heterocyclic group, a substituted or unsubstituted C2 to C30 alkenyl group, a substituted or unsubstituted C2 to C30 alkynyl group, a hydroxy group, a halogen atom, or a combination thereof,
R 11 and R 12 are independently present alone or combined to provide a ring,
R 13 and R 14 are hydrogen or are a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C3 to C30 cycloalkyl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C7 to C30 arylalkyl group, a substituted or unsubstituted C1 to C30 heteroalkyl group, a substituted or unsubstituted C2 to C30 heterocycloalkyl group, a substituted or unsubstituted C2 to C30 heterocyclic group, a substituted or unsubstituted C2 to C30 alkenyl group, a substituted or unsubstituted C2 to C30 alkynyl group, a hydroxy group, or a combination thereof combined to provide a ring,
R 15 is a halogen atom, and
* is a linking point with the condensed polycyclic ring of Chemical Formula 1, and
wherein the condensed polycyclic ring and the heterocyclic group represented by Chemical Formula 2-1 or Chemical Formula 2-2 are substantially present in the same plane.

2. The fused polycyclic heteroaromatic compound of claim 1 , wherein R 11 to R 14 are independently hydrogen.

3. The fused polycyclic heteroaromatic compound of claim 1 , wherein at least one of R 1 and R 2 is a halogen atom.

4. The fused polycyclic heteroaromatic compound of claim 1 , wherein Ar has four to eight rings.

5. The fused polycyclic heteroaromatic compound of claim 1 , wherein the condensed polycyclic ring is represented by one of Chemical Formula 3-1 to Chemical Formula 3-16:

wherein, in Chemical Formula 3-1 to Chemical Formula 3-16,
X 1 , X 2 , R 1 , R 2 , R 3 , and R 4 are the same as in Chemical Formula 1,
X 11 to X 19 are independently O, S, Se, Te, or N—R a , wherein R a is hydrogen, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C3 to C30 cycloalkyl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C7 to C30 arylalkyl group, a substituted or unsubstituted C1 to C30 heteroalkyl group, a substituted or unsubstituted C2 to C30 heterocycloalkyl group, a substituted or unsubstituted C2 to C30 heterocyclic group, a substituted or unsubstituted C2 to C30 alkenyl group, a substituted or unsubstituted C2 to C30 alkynyl group, a hydroxy group, a halogen atom, or a combination thereof.

6. The fused polycyclic heteroaromatic compound of claim 1 , wherein R 3 and R 4 have the same heterocyclic groups.

7. The fused polycyclic heteroaromatic compound of claim 1 , wherein the fused polycyclic heteroaromatic compound is represented by Chemical Formula 4:

wherein, in Chemical Formula 4,
X 1 , X 2 , Ar, R 1 , and R 2 are the same as in Chemical Formula 1,
R 41 to R 44 are independently hydrogen, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C3 to C30 cycloalkyl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C7 to C30 arylalkyl group, a substituted or unsubstituted C1 to C30 heteroalkyl group, a substituted or unsubstituted C2 to C30 heterocycloalkyl group, a substituted or unsubstituted C2 to C30 heterocyclic group, a substituted or unsubstituted C2 to C30 alkenyl group, a substituted or unsubstituted C2 to C30 alkynyl group, a hydroxy group, a halogen atom, or a combination thereof,
R 41 and R 42 are independently present alone or adjacent two thereof are combined to provide a ring, and
R 43 and R 44 are independently present alone or adjacent two thereof are combined to provide a ring.

8. The fused polycyclic heteroaromatic compound of claim 7 , wherein the fused polycyclic heteroaromatic compound is represented by one of Chemical Formula 5-1 to Chemical Formula 5-36:

9. The fused polycyclic heteroaromatic compound of claim 1 , wherein the fused polycyclic heteroaromatic compound is represented by Chemical Formula 6:

wherein, in Chemical Formula 6,
Ar, R 1 , and R 2 are the same as in Chemical Formula 1,
X 61 to X 64 are independently S or Se,
R 63 and R 66 are independently a halogen atom,
R 61 and R 62 are hydrogen or a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C3 to C30 cycloalkyl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C7 to C30 arylalkyl group, a substituted or unsubstituted C1 to C30 heteroalkyl group, a substituted or unsubstituted C2 to C30 heterocycloalkyl group, a substituted or unsubstituted C2 to C30 heterocyclic group, a substituted or unsubstitut

Assignees

• Samsung Electronics Co Ltd

Inventors

• Lee Don-Wook
• Park Jeong Il

Classifications

• C07D517/22 Primary

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

• Y02E10/549

  Organic PV cells · CPC title

• C07D495/22

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

• H01L51/0071

  Electricity · mapped topic

• H01L51/0068

  Electricity · mapped topic