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

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 heteroarylalkyl group, a substituted or unsubstituted C 2 to C 30 alkylheteroaryl group, a substituted or unsubstituted C 5 to C 30 cycloalkyl group, and a substituted or unsubstituted C 2 to C 30 heterocycloalkyl group, and

each of R x , R y , R z , R′ x , R′ y , and R′ z 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, 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.

9. The fused polycyclic heteroaromatic compound of claim 1 , wherein the fused polycyclic heteroaromatic compound is one of compounds of Chemical Formula 1-2-1:

wherein, in Chemical Formula 1-2-1,

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 C7 to C30 arylalkyl group, a substituted or unsubstituted C 2 to C 30 heteroarylalkyl group, a substituted or unsubstituted C 2 to C 30 alkylheteroaryl group, a substituted or unsubstituted C 5 to C 30 cycloalkyl group, and a substituted or unsubstituted C 2 to C 30 heterocycloalkyl group, and

each of R x , R y , R z , R′ x , R′ y , and R′ z 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, 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.

10. The fused polycyclic heteroaromatic compound of claim 1 , wherein the fused polycyclic heteroaromatic compound is one of compounds of Chemical Formula 1-3-1:

wherein, in Chemical Formula 1-3-1,

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 C7 to C30 arylalkyl group, a substituted or unsubstituted C 2 to C 30 heteroarylalkyl group, a substituted or unsubstituted C 2 to C 30 alkylheteroaryl group, a substituted or unsubstituted C 5 to C 30 cycloalkyl group, and a substituted or unsubstituted C 2 to C 30 heterocycloalkyl group, and

each of R x , R y , R z , R′ x , R′ y , and R′ z 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, 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.

11. An organic thin film comprising the fused polycyclic heteroaromatic compound of claim 1 .

12. An electronic device comprising the fused polycyclic heteroaromatic compound of claim 1 .

13. The electronic device of claim 12 , wherein the electronic device is one of a transistor, an organic light emitting diode (OLED), a photovoltaic device, a solar cell, a laser device, a memory device, and a sensor.