Aromatic hetrocyclic compound, organic light-emitting diode including organic layer comprising the aromatic hetrocyclic compound, and method of manufacturing the organic light-emitting diode

1. An aromatic heterocyclic compound represented by Formula 1 below:

wherein A is one of substituted or unsubstituted benzo[k]fluoranthene or substituted or unsubstituted chrysene;

Ar 1 is substituted or unsubstituted C 5 -C 12 arylene group,

n is an integer in the range of 0 to 6,

Ar 2 is a terminal group of Formula 2 below;

m is an integer in the range of 1 to 6; and

k is an integer in the range of 2 to 4:

wherein X 1 is N(R 4 );

X 2 and X 3 are each C(R 5 ); and

at least one of R 1 to R 5 is a linkage site to A or Ar 1 of Formula 1 above, and the remaining groups of R 1 to R 5 that are not linkage sites to A or Ar 1 are each independently one selected from the group consisting of hydrogen, halogen, cyano group, nitro group, hydroxyl group, substituted or unsubstituted C 1 -C 20 alkyl group, substituted or unsubstituted C 2 -C 20 alkenyl group, substituted or unsubstituted C 2 -C 20 alkynyl group, substituted or unsubstituted C 5 -C 20 cycloalkyl group, substituted or unsubstituted C 5 -C 20 cycloalkenyl group, substituted or unsubstituted C 5 -C 20 aryl group, substituted or unsubstituted C 2 -C 30 heteroaryl group, and a group represented by —N(Z 1 )(Z 2 ), wherein Z 1 and Z 2 are each independently one of hydrogen, substituted or unsubstituted C 1 -C 20 alkyl group, or substituted or unsubstituted C 5 -C 20 aryl group.

2. An aromatic heterocyclic compound of claim 1 , represented by Formula 1a below:

wherein k 1 is the number of linkage sites to Ar 1 among R 8 to R 19 ;

the remaining groups of R 8 to R 19 that are not linkage sites to Ar 1 are each independently one selected from the group consisting of hydrogen, halogen, cyano group, nitro group, hydroxyl group, substituted or unsubstituted C 1 -C 20 alkyl group, substituted or unsubstituted C 2 -C 20 alkenyl group, substituted or unsubstituted C 2 -C 20 alkynyl group, substituted or unsubstituted C 5 -C 20 cycloalkyl group, substituted or unsubstituted C 5 -C 20 cycloalkenyl group, substituted or unsubstituted C 5 -C 20 aryl group, substituted or unsubstituted C 2 -C 30 heteroaryl group, and a group represented by —N(Z 1 )(Z 2 ) wherein Z 1 and Z 2 are each independently one of hydrogen, substituted or unsubstituted C 1 -C 20 alkyl group, or substituted or unsubstituted C 5 -C 20 aryl group;

Ar 1 is a substituted or unsubstituted C 5 -C 12 arylene group;

n 1 is an integer in the range of 1 to 6;

Ar 2 is a terminal group of Formula 2 below;

m 1 is an integer in the range of 1 to 6; and

k 1 is an integer in the range of 2 to 4;

wherein X 1 is N(R 4 );

X 2 and X 3 are C(R 5 ); and

at least one of R 1 to R 5 is a linkage site to A or Ar 1 of Formula 1a above, and the remaining groups of R 1 to R 5 that are not linkage sites to A or Ar 1 are each independently one selected from the group consisting of hydrogen, halogen, cyano group, nitro group, hydroxyl group, substituted or unsubstituted. C 1 -C 20 alkyl group, substituted or unsubstituted C 2 -C 20 alkenyl group, substituted or unsubstituted C 2 -C 20 alkynyl group, substituted or unsubstituted C 5 -C 20 cycloalkyl group, substituted or unsubstituted C 5 -C 20 cycloalkenyl group, substituted or unsubstituted C 5 -C 20 aryl group, substituted or unsubstituted C 2 -C 30 heteroaryl group, and a group represented by —N(Z 1 )(Z 2 ), wherein Z 1 and Z 2 are each independently one of hydrogen, substituted or unsubstituted C 1 -C 20 alkyl group, or substituted or unsubstituted C 5 -C 20 aryl group.

3. An aromatic heterocyclic compound of claim 2 , wherein k is the number of linkage sites to Ar 1 among R 8 to R 19 , and the remaining groups that are not linkage sites to Ar 1 among R 8 to R 19 are each independently selected from the group consisting of hydrogen, halogen, cyano group, nitro group, hydroxyl group, substituted or unsubstituted C 1 -C 10 alkyl group, substituted or unsubstituted C 5 -C 14 aryl group, and substituted or unsubstituted C 2 -C 14 heteroaryl group.

4. An aromatic heterocyclic compound of claim 2 , wherein at least one of R 11 , R 14 , R 15 and R 18 is a linkage site to Ar 1 .

5. An aromatic heterocyclic compound of claim 1 , represented by, Formula 1b below:

wherein among R 20 to R 31 , k 2 is the number of linkage sites to one of Ar 1 or Ar 2 ;

the remaining groups among R 20 to R 31 that are not linkage sites to Ar 1 or Ar 2 are each independently one selected from the group consisting of hydrogen, halogen, cyano group, nitro group, hydroxyl group, substituted or unsubstituted C 1 -C 20 alkyl group, substituted or unsubstituted C 2 -C 20 alkenyl group, substituted or unsubstituted C 2 -C 20 alkynyl group, substituted or unsubstituted C 5 -C 20 cycloalkyl group, substituted or unsubstituted. C 5 -C 20 cycloalkenyl group, substituted or unsubstituted C 5 -C 20 aryl group, substituted or unsubstituted C 2 -C 30 heteroaryl group, and a group represented by —N(Z 1 )(Z 2 ), wherein Z 1 and Z 2 are each independently one of hydrogen, substituted or unsubstituted C 1 -C 20 alkyl group, or substituted or unsubstituted C 5 -C 20 aryl group;

Ar 1 is a substituted or unsubstituted C 5 -C 12 arylene group;

n 2 is an integer in the range of 0 to 6;

Ar 2 is a terminal group of Formula 2 below;

m 2 is an integer in the range of 1 to 6; and

k 2 is an integer in the range of 2 to 4:

wherein X 1 is N(R 4 );

X 2 and X 3 are each C(R 5 ); and

at least one of R 1 to R 5 is a linkage site to A or Ar 1 of Formula 1 above, and the remaining groups of R 1 to R 5 that are not linkage sites to A or Ar 1 are each independently one selected from the group consisting of hydrogen, halogen, cyano group, nitro group, hydroxyl group, substituted or unsubstituted C 1 -C 20 alkyl group, substituted or unsubstituted C 2 -C 20 alkenyl group, substituted or unsubstituted C 2 -C 20 alkynyl group, substituted or unsubstituted C 5 -C 20 cycloalkyl group, substituted or unsubstituted C 5 -C 20 cycloalkenyl group, substituted or unsubstituted C 5 -C 20 aryl group, substituted or unsubstituted C 2 -C 30 heteroaryl group, and a group represented by —N(Z 1 )(Z 2 ), wherein Z 1 and Z 2 are each independently one of hydrogen, substituted or unsubstituted C 1 -C 20 alkyl group, or substituted or unsubstituted C 5 -C 20 aryl group.

6. An aromatic heterocyclic compound of claim 5 , wherein k 2 is the number of linkage sites among R 20 to R 31 to one of Ar 1 or Ar 2 , and remaining groups that are not linkage sites to one of Ar 1 or Ar 2 among R 20 to R 31 are each independently selected from the group consisting of hydrogen, halogen, cyano group, nitro group, hydroxyl group, substituted or unsubstituted C 1 -C 10 alkyl group, substituted or unsubstituted C 5 -C 14 aryl group, and substituted or unsubstituted C 2 -C 14 heteroaryl group.

7. An aromatic heterocyclic compound of claim 1 , wherein A is one of the structures below:

wherein * and *' each independently represent linkage sites to Ar 1 or Ar 2 .

8. An aromatic heterocyclic compound of claim 1 , wherein Ar 1 is one selected from the group consisting of phenylene, bromophenylene, chlorophenylene, fluorophenylene, cyanophenylene, C 1 -C 10 alkylphenylene, C 1 -C 10 alkoxyphenylene, naphthylphenylene, dinaphthylphenylene, naphthylene, bromonaphthylene, chloronaphthylene, fluoronaphthylene, cyanonaphthylene, C 1 -C 10 alkylnaphthylene, C 1 -C 10 alkoxynaphthylene, phenylnaphthylene, diphenylnaphthylene, and terphenylnaphthylene.

9. An aromatic heterocyclic compound of claim 1 , wherein —(Ar 1 ) n — is one of the structures represented below:

wherein * represents a linkage site to A, and *' represents a linkage site to Ar 2 .

10. An aromatic heterocyclic compound of claim 1 , wherein one of R 1 to R 5 is a linkage site to one of A or Ar 1 , and the remaining groups of R 1 to R 5 that are not linkage sites to one of A or Ar 1 are each independently selected form the group consisting of hydrogen, halogen, cyano group, nitro group, hydroxyl group, substituted or unsubstituted C 1 -C 10 alkyl group, substituted or unsubstituted C 5 -C 14 aryl group, and substituted or unsubstituted C 2 -C 14 heteroaryl group, and a group represented by —N(Z 1 )(Z 2 ), wherein Z 1 and Z 2 are each independently one of hydrogen, substituted or unsubstituted C 1 -C 10 alkyl group, or substituted or unsubstituted C 5 -C 14 aryl group.

11. An aromatic heterocyclic compound of claim 1 , wherein one of R 1 and R 2 of Formula 2 is a linkage site to A or Ar 1 .

12. An aromatic heterocyclic compound of claim 1 , wherein X 2 and X 3 of Formula 2 are the same.

13. An aromatic heterocyclic compound of claim 1 , wherein Ar 2 is one of the structures represented below:

wherein * represents a linkage site to Ar 1 .

14. The aromatic heterocyclic compound of claim 1 , represented by one of the formulae represented below:

15. An organic light-emitting diode comprising:

a first electrode;

a second electrode; and

an organic layer between the first electrode and the second electrode, wherein the organic layer comprises an aromatic heterocyclic compound of claim 1 .

16. The organic light-emitting diode of claim 15 , wherein the organic layer is at least one selected from the group consisting of an emitting layer, an electron transport layer, a hole injection layer, a hole transport layer, and a hole blocking layer.

17. The organic light-emitting diode of claim 15 , further comprising at least one selected from the group consisting of a hole injection layer, a hole transport layer, a hole blocking layer, an electron transport layer and an electron injection layer, between the first electrode and the second electrode.

18. A method of manufacturing an organic light-emitting diode, comprising:

forming a first electrode on a substrate;

forming an organic layer comprising an aromatic heterocyclic compound of claim 1 on the first electrode; and

forming a second electrode on the organic layer.

19. The method of claim 18 , wherein the organic layer is formed using a method selected from the group consisting of vacuum deposition, spin coating, inkjet printing, screen printing, spray printing, and heat-transfer.