Heterocyclic compound and organic light-emitting device comprising the same

1. A heterocyclic compound represented by Formula 1 below:

wherein R 1 to R 13 are each independently a hydrogen atom, a heavy hydrogen atom, a substituted or unsubstituted C1-C60 alkyl group, a substituted or unsubstituted C2-C60 alkenyl group, a substituted or unsubstituted C2-C60 alkynyl group, a substituted or unsubstituted C3-C60 cycloalkyl group, a substituted or unsubstituted C1-C60 alkoxy group, a substituted or unsubstituted C5-C60 aryloxy group, a substituted or unsubstituted C5-C60 arylthio group, a substituted or unsubstituted C5-C60 aryl group, an amino group substituted with a C5-C60 aryl group or a C3-C60 heteroaryl group, a substituted or unsubstituted C3-C60 heteroaryl group, a substituted or unsubstituted C6-C60 condensed polycyclic group, a halogen atom, a cyano group, a nitro group, a hydroxy group, or a carboxy group.

2. The heterocyclic compound of claim 1 , wherein R 1 to R 5 are each independently a hydrogen atom, a heavy hydrogen atom, a halogen atom, a cyano group, a substituted or unsubstituted C1-C20 alkyl group, or one of Formulae 2a to 2i below:

wherein Q 1 is a linking group represented by —C(R 14 )(R 15 )—, —N(R 16 )—, —S—, or —O—;

Y 1 , Y 2 and Y 3 are each independently a linking group represented by —N═ or —C(R 17 )═;

Z 1 , Z 2 , Ar 12 , Ar 13 , R 14 , R 15 , R 16 , and R 17 are each independently a hydrogen atom, a heavy hydrogen atom, a substituted or unsubstituted C1-C20 alkyl group, a substituted or unsubstituted C5-C20 aryl group, a substituted or unsubstituted C3-C20 heteroaryl group, a substituted or unsubstituted C6-C20 condensed polycyclic group, a halogen atom, a cyano group, a nitro group, a hydroxy group, or a carboxy group;

Ar 11 is a substituted or unsubstituted C1-C20 alkylene group, a substituted or unsubstituted C5-C20 arylene group, or a substituted or unsubstituted C3-C20 heteroarylene group;

p is an integer from 1 to 12;

q is an integer from 1 to 12;

r is an integer from 0 to 5; and

* is a binding site.

3. The heterocyclic compound of claim 1 , wherein R 1 to R 5 are each independently a hydrogen atom, a heavy hydrogen atom, a halogen atom, a cyano group, a methyl group, an ethyl group, a propyl group, a butyl group, a t-butyl group, a pentyl group, or one of Formulae 3a to 3m below:

wherein Ar 12 and Ar 13 are each independently a substituted or unsubstituted C5-C20 aryl group, a substituted or unsubstituted C3-C20 heteroaryl group, or a substituted or unsubstituted C6-C20 condensed polycyclic group;

r is an integer from 0 to 2; and

* is a binding site.

4. The heterocyclic compound of claim 1 , wherein R 6 to R 8 and R 10 to R 13 are each independently a hydrogen atom or a heavy hydrogen atom, and R 9 is —X 1 —N(Ar 1 Ar 2 ) that is a substituted C5-C60 aryl group, a substituted C3-C60 heteroaryl group, or a substituted C6-C60 condensed polycyclic group; or

R 6 to R 10 , R 12 and R 13 are each independently a hydrogen atom or a heavy hydrogen atom, and R 11 is —X 1 —N(Ar 1 Ar 2 ) that is a substituted C5-C60 aryl group, a substituted C3-C60 heteroaryl group or a substituted C6-C60 condensed polycyclic group,

wherein X 1 is a divalent linking group represented by —(Ar 3 ) n —, wherein Ar 3 is a substituted or unsubstituted C5-C60 arylene group, a substituted or unsubstituted C3-C60 heteroarylene group, or a substituted or unsubstituted C6-C60 condensed polycyclic group, and n is an integer from 1 to 10;

the Ar 3 's are the same or different;

at least two adjacent Ar 3 's are fused or linked to each other via a single bond; and

Ar 1 and Ar 2 are each independently one of Formulae 4a to 4d below:

wherein Q 1 is a linking group represented by —C(R 14 )(R 15 )—, —N(R 16 )—, —S—, or —O—;

Y 1 , Y 2 and Y 3 are each independently a linking group represented by —N═ or —C(R 17 )═;

Z 1 , Z 2 , R 14 , R 15 , R 16 , and R 17 are each independently a hydrogen atom, a heavy hydrogen atom, a substituted or unsubstituted C1-C20 alkyl group, a substituted or unsubstituted C5-C20 aryl group, a substituted or unsubstituted C3-C20 heteroaryl group, a substituted or unsubstituted C6-C20 condensed polycyclic group, a halogen atom, a cyano group, a nitro group, a hydroxy group, or a carboxy group;

p is an integer from 1 to 8; and

* is a binding site.

5. The heterocyclic compound of claim 1 , wherein R 6 to R 8 and R 10 to R 13 are each independently a hydrogen atom or a heavy hydrogen atom, and R 9 is —X 1 —N(Ar 1 Ar 2 ) that is a substituted C5-C60 aryl group, a substituted C3-C60 heteroaryl group, or a substituted C6-C60 condensed polycyclic group; or

R 6 to R 10 , R 12 and R 13 are each independently a hydrogen atom or a heavy hydrogen atom, and R 11 is —X 1 —N(Ar 1 Ar 2 ) that is a substituted C5-C60 aryl group, a substituted C3-C60 heteroaryl group or a substituted C6-C60 condensed polycyclic group,

wherein X 1 is a divalent linking group represented by —(Ar 3 ) n —, wherein Ar 3 is a substituted or unsubstituted C5-C60 arylene group, a substituted or unsubstituted C3-C60 heteroarylene group, or a substituted or unsubstituted C6-C60 condensed polycyclic group, and n is an integer from 1 to 10;

the Ar 3 's are the same or different;

at least two adjacent Ar 3 's are fused or linked to each other via a single bond; and

Ar 1 and Ar 2 are each independently represented by one of Formulae 5a to 5i below:

wherein Z 1 to Z 5 are each independently a hydrogen atom, a heavy hydrogen atom, a halogen atom, a cyano group, a substituted or unsubstituted C1-C20 alkyl group, a substituted or unsubstituted C1-C20 alkoxy group, a substituted or unsubstituted C5-C20 aryl group, a substituted or unsubstituted C3-C20 heteroaryl group, or a substituted or unsubstituted C6-C20 condensed polycyclic group; and

* is a binding site.

6. The heterocyclic compound of claim 1 , wherein R 9 or R 11 are each independently X 1 —N(Ar 1 Ar 2 ) that is a substituted C5-C60 aryl group, a substituted C3-C60 heteroaryl group, or a substituted C6-C60 condensed polycyclic group,

wherein Ar 1 and Ar 2 are each independently a substituted or unsubstituted C3-C50 cycloalkyl group, a substituted or unsubstituted C5-C60 aryloxy group, a substituted or unsubstituted C5-C60 arylthio group, a substituted or unsubstituted C5-C60 aryl group, an amino group substituted with a C5-C60 aryl group or a C3-C60 heteroaryl group, a substituted or unsubstituted C3-C60 heteroaryl group, or a substituted or unsubstituted C6-C60 condensed polycyclic group; and

X 1 is a divalent linking group represented by —(Ar 3 ) n —, wherein Ar 3 is one of Formulae 6a to 6e, and the Ar 3 's are the same or different; and at least two adjacent Ar 3 's are fused or linked to each other via a single bond:

wherein Q 1 is a linking group represented by —C(R 14 )(R 15 )—, —S—, or —O—;

Y 4 , Y 5 and Y 6 are each independently a linking group represented by —O—, —S—, —N═ or —C(R 17 )═;

Z 1 , Z 2 , R 14 , R 15 , R 16 , and R 17 are each independently a hydrogen atom, a heavy hydrogen atom, a substituted or unsubstituted C1-C20 alkyl group, a substituted or unsubstituted C5-C20 aryl group, a substituted or unsubstituted C3-C20 heteroaryl group, a substituted or unsubstituted C6-C20 condensed polycyclic group, a halogen atom, a cyano group, a nitro group, a hydroxy group, or a carboxy group;

p is an integer from 1 to 4;

q is an integer from 1 to 4; and

* is a binding site.

7. The heterocyclic compound of claim 1 , wherein R 9 or R 11 are each independently X 1 —N(Ar 1 Ar 2 ) that is a substituted C5-C60 aryl group, a substituted C3-C60 heteroaryl group, or a substituted C6-C60 condensed polycyclic group,

wherein Ar 1 and Ar 2 are each independently a substituted or unsubstituted C3-C50 cycloalkyl group, a substituted or unsubstituted C5-C60 aryloxy group, a substituted or unsubstituted C5-C60 arylthio group, a substituted or unsubstituted C5-C60 aryl group, an amino group substituted with a C5-C60 aryl group or a C3-C60 heteroaryl group, a substituted or unsubstituted C3-C60 heteroaryl group, or a substituted or unsubstituted C6-C60 condensed polycyclic group; and

X 1 is one of Formulae 7a to 7k below:

wherein * is a binding site.

8. The heterocyclic compound of claim 1 , wherein the heterocyclic compound of Formula 1 is represented by Formula 2 or Formula 3 below:

wherein R 1 to R 5 are each independently a hydrogen atom, a heavy hydrogen atom, a substituted or unsubstituted C1-C60 alkyl group, a substituted or unsubstituted C2-C60 alkenyl group, a substituted or unsubstituted C2-C60 alkynyl group, a substituted or unsubstituted C3-C60 cycloalkyl group, a substituted or unsubstituted C1-C60 alkoxy group, a substituted or unsubstituted C5-C60 aryloxy group, a substituted or unsubstituted C5-C60 arylthio group, a substituted or unsubstituted C5-C60 aryl group, an amino group substituted with a C5-C60 aryl group or a C3-C60 heteroaryl group, a substituted or unsubstituted C3-C60 heteroaryl group, a substituted or unsubstituted C6-C60 condensed polycyclic group, a halogen atom, a cyano group, a nitro group, a hydroxy group, or a carboxy group;

Ar 1 and Ar 2 are each independently a substituted or unsubstituted C3-C50 cycloalkyl group, a substituted or unsubstituted C5-C60 aryloxy group, a substituted or unsubstituted C5-C60 arylthio group, a substituted or unsubstituted C5-C60 aryl group, an amino group substituted with a C5-C60 aryl group or a C3-C60 heteroaryl group, a substituted or unsubstituted C3-C60 heteroaryl group, or a substituted or unsubstituted C6-C60 condensed polycyclic group;

X 1 is a divalent linking group represented by —(Ar 3 ) n —, wherein Ar 3 may be a substituted or unsubstituted C5-C60 arylene group, a substituted or unsubstituted C3-C60 heteroarylene group, or a substituted or unsubstituted C6-C60 condensed polycyclic group, and n is an integer from 1 to 10;

the Ar 3 's are the same or different; and

at least two adjacent Ar 3 's are fused or linked to each other via a single bond.

9. The heterocyclic compound of claim 8 , wherein R 1 to R 5 are each independently a hydrogen atom, a heavy hydrogen atom, a halogen atom, a cyano group, a substituted or unsubstituted C1-C20 alkyl group, or one of Formulae 2a to 2i below:

wherein Q 1 is a linking group represented by —C(R 14 )(R 15 )—, —N(R 16 )—, —S—, or —O—;

Y 1 , Y 2 and Y 3 are each independently a linking group represented by —N═ or —C(R 17 )═;

Z 1 , Z 2 , Ar 12 , Ar 13 , R 14 , R 15 , R 16 , and R 17 are each independently a hydrogen atom, a heavy hydrogen atom, a substituted or unsubstituted C1-C20 alkyl group, a substituted or unsubstituted C5-C20 aryl group, a substituted or unsubstituted C3-C20 heteroaryl group, a substituted or unsubstituted C6-C20 condensed polycyclic group, a halogen atom, a cyano group, a nitro group, a hydroxy group, or a carboxy group;

Ar 11 is a substituted or unsubstituted C1-C20 alkylene group, a substituted or unsubstituted C5-C20 arylene group, or a substituted or unsubstituted C3-C20 heteroarylene group;

p is an integer from 1 to 12;

q is an integer from 1 to 12;

r is an integer from 0 to 5; and

* is a binding site.

10. The heterocyclic compound of claim 8 , wherein R 1 to R 5 are each independently a hydrogen atom, a heavy hydrogen atom, a halogen atom, a cyano group, a methyl group, an ethyl group, a propyl group, a butyl group, a t-butyl group, a pentyl group, or one of Formulae 3a to 3m below:

wherein Ar 12 and Ar 13 are each independently a substituted or unsubstituted C5-C20 aryl group, a substituted or unsubstituted C3-C20 heteroaryl group, or a substituted or unsubstituted C6-C20 condensed polycyclic group;

r is an integer from 0 to 2; and

* is a binding site.

11. The heterocyclic compound of claim 8 , wherein Ar 1 and Ar 2 are each independently one of Formulae 4a to 4d below:

wherein Q 1 is a linking group represented by —C(R 14 )(R 15 )—, —N(R 16 )—, —S—, or —O—;

Y 1 , Y 2 and Y 3 are each independently a linking group represented by —N═ or —C(R 17 )═;

Z 1 , Z 2 , R 14 , R 15 , R 16 , and R 17 are each independently a hydrogen atom, a heavy hydrogen atom, a substituted or unsubstituted C1-C20 alkyl group, a substituted or unsubstituted C5-C20 aryl group, a substituted or unsubstituted C3-C20 heteroaryl group, a substituted or unsubstituted C6-C20 condensed polycyclic group, a halogen atom, a cyano group, a nitro group, a hydroxy group, or a carboxy group;

p is an integer from 1 to 8; and

* is a binding site.

12. The heterocyclic compound of claim 8 , wherein Ar 1 and Ar 2 are each independently one of Formulae 5a to 5i below:

wherein Z 1 to Z 5 are each independently a hydrogen atom, a heavy hydrogen atom, a halogen atom, a cyano group, a substituted or unsubstituted C1-C20 alkyl group, a substituted or unsubstituted C1-C20 alkoxy group, a substituted or unsubstituted C5-C20 aryl group, a substituted or unsubstituted C3-C20 heteroaryl group, or a substituted or unsubstituted C6-C20 condensed polycyclic group; and

* is a binding site.

13. The heterocyclic compound of claim 8 , wherein Ar 3 is one of Formulae 6a to 6e below:

wherein Q 1 is a linking group represented by —C(R 14 )(R 15 )—, —N(R 16 )—, —S—, or —O—;

Y 4 , Y 5 and Y 6 are each independently a linking group represented by —O—, —S—, —N═ or —C(R 17 )═;

Z 1 , Z 2 , R 14 , R 15 , R 16 , and R 17 are each independently a hydrogen atom, a heavy hydrogen atom, a substituted or unsubstituted C1-C20 alkyl group, a substituted or unsubstituted C5-C20 aryl group, a substituted or unsubstituted C3-C20 heteroaryl group, a substituted or unsubstituted C6-C20 condensed polycyclic group, a halogen atom, a cyano group, a nitro group, a hydroxy group, or a carboxy group;

p is an integer from 1 to 4;

q is an integer from 1 to 4; and

* is a binding site.

14. The heterocyclic compound of claim 8 , wherein X 1 is one of Formulae 7a to 7k below:

wherein * is a binding site.

15. The heterocyclic compound of claim 1 , wherein the heterocyclic compound of Formula 1 is one of the compounds below:

16. An organic light-emitting device comprising:

a first electrode;

a second electrode; and

an organic layer interposed between the first electrode and the second electrode,

the organic layer comprised of a first layer comprising a heterocyclic compound according to claim 1 .

17. The organic light-emitting device of claim 16 , wherein the first layer comprises a hole injection layer, a hole transport layer, a layer having both hole injecting and hole transporting capabilities, an emission layer, an electron injection layer, an electron transport layer, or a layer having both electron injecting and electron transporting capabilities.

18. The organic light-emitting device of claim 16 , wherein the first layer comprises a hole injection layer, a hole transport layer, a layer having both hole injecting and hole transporting capabilities, an emission layer, an electron injection layer, an electron transport layer, or a layer having both electron injecting and electron transporting capabilities, wherein the first layer further comprises a charge-generating material.

19. The organic light-emitting device of claim 16 , wherein the first layer is formed of a heterocyclic compound represented by Formula 1 by using a wet process;

wherein R 1 to R 13 are each independently a hydrogen atom, a heavy hydrogen atom, a substituted or unsubstituted C1-C60 alkyl group, a substituted or unsubstituted C2-C60 alkenyl group, a substituted or unsubstituted C2-C60 alkynyl group, a substituted or unsubstituted C3-C60 cycloalkyl group, a substituted or unsubstituted C1-C60 alkoxy group, a substituted or unsubstituted C5-C60 aryloxy group, a substituted or unsubstituted C5-C60 arylthio group, a substituted or unsubstituted C5-C60 aryl group, an amino group substituted with a C5-C60 aryl group or a C3-C60 heteroaryl group, a substituted or unsubstituted C3-C60 heteroaryl group, a substituted or unsubstituted C6-C60 condensed polycyclic group, a halogen atom, a cyano group, a nitro group, a hydroxy group, or a carboxy group.

20. A flat panel display device comprising the organic light-emitting device of claim 16 , wherein a first electrode of the organic light-emitting device is electrically connected to a source electrode or a drain electrode of a thin film transistor.