Fused polycyclic heteroaromatic compound, organic thin film including compound and electronic device including organic thin film

Patent metadata

Field	Value
Publication number	US-9947873-B2
Application number	US-201715621021-A
Country	US
Kind code	B2
Filing date	Jun 13, 2017
Priority date	Jun 13, 2016
Publication date	Apr 17, 2018
Grant date	Apr 17, 2018

Abstract

A low-molecular-weight fused polycyclic heteroaromatic compound has a compact planar structure in which seven or more aromatic rings and heteroaromatic rings are fused together, and thereby exhibits relatively high charge mobility, and improved processibility due to improved dissolubility for a solvent. An organic thin film and an electronic device include the fused polycyclic heteroaromatic compound expressed in Chemical Formula 1.

First claim

What is claimed is:

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

wherein, in Chemical Formula 1,
each of X 1 to X 8 is independently one of S, Se, Te, N—R a , and C—R b , wherein R a and R b are independently one of hydrogen, a halogen, a cyano group, a linear or branched substituted or unsubstituted C 1 to C 10 alkyl group, a substituted or unsubstituted C 3 to C 10 cycloalkyl group, a substituted or unsubstituted C 6 to C 10 aryl group, and a substituted or unsubstituted C 4 to C 10 heteroaryl group,
one of X 1 to X 3 is one of S, Se, Te, and N—R a and remaining two of X 1 to X 3 are C—R b wherein R b is one of hydrogen, a halogen, a cyano group, a linear or branched substituted or unsubstituted C 1 to C 10 alkyl group, a substituted or unsubstituted C 3 to C 10 cycloalkyl group, a substituted or unsubstituted C 6 to C 10 aryl group, and a substituted or unsubstituted C 4 to C 10 heteroaryl group or R b 's are linked with each other to provide a C 5 aromatic ring or a C 6 aromatic ring,
one of X 4 to X 6 is one of S, Se, Te, and N—R a and remaining two of X 4 to X 6 are C—R b wherein R b is one of hydrogen, a halogen, a cyano group, a linear or branched substituted or unsubstituted C 1 to C 10 alkyl group, a substituted or unsubstituted C 3 to C 10 cycloalkyl group, a substituted or unsubstituted C 6 to C 10 aryl group, and a substituted or unsubstituted C 4 to C 10 heteroaryl group or R b 's are linked with each other to provide a C 5 aromatic ring or a C 6 aromatic ring,
each of R 3 to R 6 is independently one of hydrogen, a halogen, a cyano group, a C 1 to C 4 alkyl group, and a C 1 to C 4 fluoroalkyl group, and
each of R 1 and R 2 is independently a functional group represented by Chemical Formula 2,
*-L-Y 1   [Chemical Formula 2]

wherein, in Chemical Formula 2,
L is an ethynylene group or a functional group represented by Chemical Formula 2-1, and
Y 1 is one of hydrogen, a halogen, a cyano group, —Si(R x )(R y )(R z ) (wherein each of R x , R y , and R z are independently one of hydrogen, a halogen, a cyano group, a linear or branched substituted or unsubstituted C 1 to C 10 alkyl group, a substituted or unsubstituted C 3 to C 10 cycloalkyl group, a substituted or unsubstituted C 6 to C 10 aryl group, and a substituted or unsubstituted C 4 to C 10 heteroaryl group), a linear or branched substituted or unsubstituted C 1 to C 10 alkyl group, a substituted or unsubstituted C 3 to C 10 cycloalkyl group, a substituted or unsubstituted C 6 to C 10 aryl group, and a substituted or unsubstituted C 4 to C 10 heteroaryl group,

wherein, in Chemical Formula 2-1,
each of R 31 to R 34 is independently one of hydrogen, a halogen, a cyano group, a linear or branched substituted or unsubstituted C 1 to C 10 alkyl group, a substituted or unsubstituted C 3 to C 10 cycloalkyl group, a substituted or unsubstituted C 6 to C 10 aryl group, and a substituted or unsubstituted C 4 to C 10 heteroaryl group or optionally R 31 and R 32 are linked with each other to provide a C 5 aromatic ring or a C 6 aromatic ring or optionally R 33 and R 34 are linked with each other to provide a C 5 aromatic ring or a C 6 aromatic ring.

2. The fused polycyclic heteroaromatic compound of claim 1 , wherein the fused polycyclic heteroaromatic compound represented by Chemical Formula 1 is one of compounds represented by Chemical Formulae 1-1 to 1-3:

wherein, in Chemical Formulae 1-1 to 1-3,
R 1 to R 6 are same as in Chemical Formula 1,
each of X 1 to X 8 is one of S, Se, Te, and N—R a , wherein R a is one of hydrogen, a halogen, a cyano group, a linear or branched substituted or unsubstituted C 1 to C 10 alkyl group, a substituted or unsubstituted C 3 to C 10 cycloalkyl group, a substituted or unsubstituted C 6 to C 10 aryl group, and a substituted or unsubstituted C 4 to C 10 heteroaryl group, and
each of R 11 to R 22 is independently one of hydrogen, a halogen, a cyano group, a linear or branched substituted or unsubstituted C 1 to C 10 alkyl group, a substituted or unsubstituted C 3 to C 10 cycloalkyl group, a substituted or unsubstituted C 6 to C 10 aryl group, and a substituted or unsubstituted C 4 to C 10 heteroaryl group, or optionally at least one of R 11 and R 12 and R 13 and R 14 or at least one of R 19 and R 20 and R 21 and R 22 are linked with each other to provide a C 5 aromatic ring or a C 6 aromatic ring.

3. The fused polycyclic heteroaromatic compound of claim 1 , wherein in Chemical Formula 1:
one of X 1 to X 3 is independently a sulfur atom (S) or a selenium atom (Se), and
one of X 4 to X 6 is independently a sulfur atom (S) or a selenium atom (Se).

4. The fused polycyclic heteroaromatic compound of claim 1 , wherein in Chemical Formula 1:
the C 5 aromatic ring or the C 6 aromatic ring is respectively an X 9 -containing ring and an X 10 -containing ring wherein X 9 and X 10 are independently one of O, S, Se, Te, N—R a , and
C(R c )═C(R d ), wherein each of R a , R c , and R d are independently one of hydrogen, a halogen, a cyano group, a linear or branched substituted or unsubstituted C 1 to C 10 alkyl group, a substituted or unsubstituted C 3 to C 10 cycloalkyl group, a substituted or unsubstituted C 6 to C 10 aryl group, and a substituted or unsubstituted C 4 to C 10 heteroaryl group.

5. The fused polycyclic heteroaromatic compound of claim 1 , wherein in Chemical Formula 2:
the C 5 aromatic ring or the C 6 aromatic ring is respectively an X 11 -containing ring and an X 12 -containing ring, wherein X 11 and X 12 are independently one of O, S, Se, Te, N—R a , and
C(R c )═C(R d ), wherein each of R a , R c , and R d are independently one of hydrogen, a halogen, a cyano group, a linear or branched substituted or unsubstituted C 1 to C 10 alkyl group, a substituted or unsubstituted C 3 to C 10 cycloalkyl group, a substituted or unsubstituted C 6 to C 10 aryl group, and a substituted or unsubstituted C 4 to C 10 heteroaryl group.

6. The fused polycyclic heteroaromatic compound of claim 1 , wherein the functional group represented by Chemical Formula 2-1 is one of functional groups represented by Chemical Formula 2-1-1:

7. The fused polycyclic heteroaromatic compound of claim 1 , wherein the fused polycyclic heteroaromatic compound has an average molecular weight of about 300 to about 3000.

8. The fused polycyclic heteroaromatic compound of claim 1 , wherein the fused polycyclic heteroaromatic compound is one of compounds of Chemical Formula 1-1-1:

wherein, in Chemical Formula 1-1-1,
each of R 4 and R 5 is independently one of hydrogen, a halogen, a cyano group, a substituted or unsubstituted C 1 to C 30 alkyl group, a substituted or unsubstituted C 6 to C 30 aryl group, a substituted or unsubstituted C 2 to C 30 heteroaryl group, a substituted or unsubstituted C 7 to C 30 arylalkyl group, a substituted or unsubstituted C 2 to C 30 heteroaryla

Assignees

• Samsung Electronics Co Ltd

Inventors

• Park Jeong Il
• Kang Hyun Bum

Classifications

• H01L51/0062

  Electricity · mapped topic

• C07D513/22

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

• C07D517/22

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

• C07D495/22 Primary

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

• C07D487/22 Primary

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