Organic light-emitting device

1. A heterocyclic compound represented by Formula 1 below:

wherein R 1 through R 5 are each independently a hydrogen atom, a deuterium atom, a substituted or unsubstituted C 1 -C 60 alkyl group, a substituted or unsubstituted C 2 -C 60 alkenyl group, a substituted or unsubstituted C 2 -C 60 alkynyl group, a substituted or unsubstituted C 3 -C 60 cycloalkyl group, a substituted or unsubstituted C 1 -C 60 alkoxy group, a substituted or unsubstituted C 5 -C 60 aryloxy group, a substituted or unsubstituted C 5 -C 60 arylthio group, a substituted or unsubstituted C 5 -C 60 aryl group, an amino group substituted with a C 5 -C 60 aryl or C 3 -C 60 heteroaryl group, a substituted or unsubstituted C 3 -C 60 heteroaryl group, a substituted or unsubstituted C 6 -C 60 condensed polycyclic group, a halogen atom, a cyano group, a nitro group, a hydroxyl group, or a carboxyl group;

Ar 1 and Ar 2 are each independently a substituted or unsubstituted C 3 -C 50 cycloalkyl group, a substituted or unsubstituted C 5 -C 60 aryloxy group, a substituted or unsubstituted C 5 -C 60 arythio group, a substituted or unsubstituted C 5 -C 60 aryl group, an amino group substituted with a C 5 -C 60 aryl or C 3 -C 60 heteroaryl group, a substituted or unsubstituted C 3 -C 60 heteroaryl group, or a substituted or unsubstituted C 6 -C 60 condensed polycyclic group; and

X is a divalent linking group represented by —(Ar 3 ) n — wherein Ar 3 is a substituted or unsubstituted C 5 -C 60 arylene group, a substituted or unsubstituted C 3 -C 60 heteroarylene group, or a substituted or unsubstituted C 6 -C 60 condensed polycyclic group, and n is an integer from 1 to 10, wherein n groups of Ar 3 are identical to or different from each other, and wherein when n is greater than 1, at least two adjacent groups of the n Ar 3 groups are fused or linked to each other by a single bond.

2. The heterocyclic compound of claim 1 , wherein R 1 to R 5 in Formula 1 are each independently a hydrogen atom, a deuterium atom, a cyano group, a halogen atom, an unsubstituted C 1 -C 20 alkyl group, a substituted C 1 -C 20 alkyl group with at least one fluorine (—F) substituent, a substituted or unsubstituted C 5 -C 20 aryl group, or a substituted or unsubstituted C 3 -C 20 heteroaryl group.

3. The heterocyclic compound of claim 1 , wherein R 1 to R 5 in Formula 1 are each independently a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted C 1 -C 20 alkyl group, or groups represented by Formulae 2a to 2i below:

wherein, in Formulae 2a to 2i, Q 1 is a linking group represented by —C(R 6 )(R 7 )—, —N(R 6 )—, —S—, or —O—;

Y 1 , Y 2 , and Y 3 are each independently a linking group represented by —N═ or —C(R 8 )═;

Z 1 , Z 2 , Ar 12 , Ar 13 , R 6 , R 7 , and R 8 are each independently a hydrogen atom, a deuterium atom, a substituted or unsubstituted C 1 -C 20 alkyl group, a substituted or unsubstituted C 5 -C 20 aryl group, a substituted or unsubstituted C 3 -C 20 heteroaryl group, a substituted or unsubstituted C 6 -C 20 condensed polycyclic group, a halogen atom, a cyano group, a nitro group, a hydroxyl group, or a carboxy group;

Ar 11 is a substituted or unsubstituted C 1 -C 20 alkylene group, a substituted or unsubstituted C 5 -C 20 arylene group, or a substituted or unsubstituted C 3 -C 20 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

* indicates a binding site.

4. The heterocyclic compound of claim 1 , wherein R 1 to R 5 in Formula 1 are each independently a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a methyl group, an ethyl group, a propyl group, a butyl group, a pentyl group, or groups represented by Formulae 3a to 31 below:

wherein in Formula 3a to 31, Ar 12 and Ar 13 are each independently an unsubstituted aryl group, a substituted or unsubstituted C 3 -C 20 heteroaryl group, or a substituted or unsubstituted C 6 -C 20 condensed polycyclic group;

r is an integer from 0 to 2; and

* indicates a binding site.

5. The heterocyclic compound of claim 1 , wherein R 2 and R 5 in Formula 1 are hydrogen atoms; and R 1 , R 3 , and R 4 are each independently a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a methyl group, an ethyl group, a propyl group, a butyl group, a pentyl group, or groups represented by Formulae 3a to 3l below:

wherein, in Formula 3a to 3l, Ar 12 and Ar 13 are each independently an unsubstituted aryl group, a substituted or unsubstituted C 3 -C 20 heteroaryl group, or a substituted or unsubstituted C 6 -C 20 condensed polycyclic group; r is an integer from 0 to 2; and * indicates a binding site.

6. The heterocyclic compound of claim 1 , wherein R 2 and R 5 are hydrogen atoms;

R 1 is a substituted or unsubstituted C 6 -C 20 aryl group or a substituted or unsubstituted C 3 -C 20 heteroaryl group,

R 3 is a hydrogen atom or a substituted or unsubstituted C 6 -C 20 aryl group, and

R 4 is a hydrogen atom or an amino group substituted with a C 3 -C 20 heteroaryl group.

7. The heterocyclic compound of claim 1 , wherein Ar 1 and Ar 2 in Formula 1 are each independently a substituted or unsubstituted C 1 -C 20 alkyl group, a substituted or unsubstituted C 5 -C 20 aryl group, or a substituted or unsubstituted C 3 -C 20 heteroaryl group.

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

wherein, in Formula 4a to 4d, Q 1 is a linking group represented by —C(R 6 )(R 7 )—, —N(R 6 )—, —S—, or —O—;

Y 1 , Y 2 , and Y 3 are each independently a linking group represented by —N═ or —C(R 8 )═;

Z 1 , Z 2 , R 6 , R 7 , and R 8 are each independently a hydrogen atom, a deuterium atom, a substituted or unsubstituted C 1 -C 20 alkyl group, a substituted or unsubstituted C 5 -C 20 aryl group, a substituted or unsubstituted C 3 -C 20 heteroaryl group, a substituted or unsubstituted C 6 -C 20 condensed polycyclic group, a halogen atom, a cyano group, a nitro group, a hydroxyl group, or a carboxy group;

p is an integer from 1 to 8; and

* indicates a binding site.

9. The heterocyclic compound of claim 1 , wherein Ar 1 and Ar 2 in Formula 1 are each independently a group represented by one of Formulae 5a to 5i below:

wherein Z 1 and Z 2 are each independently a hydrogen atom, a deuterium atom, a substituted or unsubstituted C 1 -C 20 alkyl group, a substituted or unsubstituted C 5 -C 20 aryl group, a substituted or unsubstituted C 3 -C 20 heteroaryl group, or a substituted or unsubstituted C 6 -C 20 condensed polycyclic group; and * indicates a binding site.

10. The heterocyclic compound of claim 1 , wherein Ar 3 for X in Formula 1 is a substituted or unsubstituted C 5 -C 20 arylene group, a substituted or unsubstituted C 3 -C 20 heteroarylene group, or a substituted or unsubstituted C 6 -C 20 condensed polycyclic group.

11. The heterocyclic compound of claim 1 , wherein Ar 3 for X in Formula 1 comprises a group represented by one of Formulae 6a to 6e below:

wherein, in Formula 6a to 6e, Q 1 is a linking group represented by —C(R 6 )(R 7 )—, —N(R 6 )—, or —S—;

Y 4 , Y 5 , and Y 6 are each independently a linking group represented by —N═ or —C(R 8 )═, —S—, or —O—;

Z 1 , Z 2 , R 6 , R 7 , and R 8 are each independently a hydrogen atom, a deuterium atom, a substituted or unsubstituted C 1 -C 20 alkyl group, a substituted or unsubstituted C 5 -C 20 aryl group, a substituted or unsubstituted C 3 -C 20 heteroaryl group, a substituted or unsubstituted C 6 -C 20 condensed polycyclic group, a halogen atom, a cyano group, a nitro group, a hydroxyl group, or a carboxy group;

p is an integer from 1 to 8;

q is an integer from 1 to 8; and

* indicates a binding site.

12. The heterocyclic compound of claim 1 , wherein n is 1 or 2.

13. The heterocyclic compound of claim 1 , wherein X in Formula 1 comprises a group represented by one of Formulae 7a to 7j:

wherein, in Formula 7a to 7j, * indicates a binding site.

14. The heterocyclic compound of claim 1 , wherein R 1 , R 3 , and R 4 in Formula 1 are each independently a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a methyl group, an ethyl group, a propyl group, a butyl group, a pentyl group, or groups represented by Formulae 3a to 3l below:

wherein, in Formula 3a to 3l, Ar 12 and Ar 13 are each independently an unsubstituted aryl group, a substituted or unsubstituted C 3 -C 20 heteroaryl group, or a substituted or unsubstituted C 6 -C 20 condensed polycyclic group; r is an integer from 0 to 2, and * indicates a binding site;

R 2 and R 5 are hydrogen atoms;

Ar 3 comprises a group represented by one of Formulae 6a to 6e below:

wherein, in Formulae 6a to 6e, Q 1 is a linking group represented by —C(R 6 )(R 7 )—, —N(R 6 )—, or —S—; Y 4 , Y 5 and Y 6 are each independently a linking group represented by —N═, —C(R 8 )═, —S—, or —O—; Z 1 , Z 2 , R 6 , R 7 , and R 8 are each independently a hydrogen atom, a deuterium atom, a substituted or unsubstituted C 1 -C 20 alkyl group, a substituted or unsubstituted C 5 -C 20 aryl group, a substituted or unsubstituted C 3 -C 20 heteroaryl group, a substituted or unsubstituted C 6 -C 20 condensed polycyclic group, a halogen atom, a cyano group, a nitro group, a hydroxyl group, or a carboxy group; p is an integer from 1 to 8; q is an integer from 1 to 8; and * indicates a binding site;

n in Formula 1 is 1 or 2; and

Ar 1 and Ar 2 are each independently selected from among groups represented by Formulae 4a to 4d below:

wherein, in Formulae 4a to 4d, Q 1 is a linking group represented by —C(R 6 )(R 7 )—, —N(R 6 )—, —S—, or —O—; Y 1 , Y 2 and Y 3 are each independently a linking group represented by —N═ or —C(R 8 )═; Z 1 , Z 2 , R 6 , R 7 , and R 8 are each independently a hydrogen atom, a deuterium atom, a substituted or unsubstituted C 1 -C 20 alkyl group, a substituted or unsubstituted C 5 -C 20 aryl group, a substituted or unsubstituted C 3 -C 20 heteroaryl group, a substituted or unsubstituted C 6 -C 20 condensed polycyclic group, a halogen atom, a cyano group, a nitro group, a hydroxyl group, or a carboxy group; p is an integer from 1 to 8; and * indicates a binding site.

15. The heterocyclic compound of claim 1 , comprising one of the compounds below:

16. An organic light-emitting device comprising:

a first electrode;

a second electrode; and

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

wherein the organic layer comprises a first layer comprising the heterocyclic compound of claim 1 .

17. The organic light-emitting device of claim 16 , wherein the first layer comprises at least one layer, a hole injection layer, a hole transport layer, a functional layer having both hole injection and hole transport capabilities, an electron injection layer, an electron transport layer, a functional layer having both electron injection and electron transport capabilities or any combination thereof.

18. The organic light-emitting device of claim 16 , wherein the first layer comprises an emission layer, and the heterocyclic compound of Formula 1 is used in the emission layer as a host or a dopant for a fluorescent or phosphorescent device.

19. The organic light-emitting device of claim 16 , wherein

the first layer comprises an emission layer, and the emission layer comprises an anthracene compound, an arylamine compound, or a styryl compound.

20. The organic light-emitting device of claim 16 , wherein

the first layer comprises an emission layer, and a red layer, a green layer, a blue layer, or a white layer of the emission layer comprises a phosphorescent compound.

21. The organic light-emitting device of claim 16 , wherein the first layer comprises a blue emission layer.

22. The organic light-emitting device of claim 16 , wherein the first layer comprises a blue emission layer; and the heterocyclic compound of Formula 1 is used as a blue dopant.

23. The organic light-emitting device of claim 16 , wherein the organic layer further comprises a hole injection layer, a hole transport layer, a functional layer having hole injecting and transporting capabilities, an emission layer, a hole blocking layer, an electron transport layer, an electron injecting layer, or a combination of two or more layers thereof.

24. The organic light-emitting device of claim 23 , at least one layer selected from the hole injection layer, the hole transport layer, or the functional layer having hole injecting and transporting capabilities further comprises a charge-generating material.

25. The organic light-emitting device of claim 23 , wherein the electron transport layer of the organic light-emitting device comprises an electron transporting organic material and a metal-containing material.

26. The organic light-emitting device of claim 25 , wherein the metal-containing material comprises a Li complex.

27. The organic light-emitting device of claim 16 , wherein the first layer is formed by using a wetting process by using the heterocyclic compound of claim 1 .

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