Condensed-cyclic compound and organic light emitting diode including organic layer containing the condensed-cyclic compound

1. A condensed-cyclic compound represented by Formula 1 below:

wherein R 8 and R 7 are not identical and are each independently selected from the group consisting of a hydrogen atom, a halogen atom, a hydroxyl group, a cyano group, a substituted or unsubstituted C 1 -C 30 alkyl group, a substituted or unsubstituted C 2 -C 30 alkenyl group, a substituted or unsubstituted C 2 -C 30 alkynyl group, a substituted or unsubstituted C 1 -C 30 alkoxy group, a group represented by —(Ar 1 ) a —Ar 11 , and a group represented by —N[—(Ar 2 ) b —Ar 12 ][—(Ar 3 ) c —Ar 13 ]; or R 8 is connected to * of Formula 2 and R 7 is connected to *′ of Formula 2 represented by:

wherein R 1 through R 6 , R 11 through R 14 , and R 21 through R 24 are each independently selected from the group consisting of a hydrogen atom, a halogen atom, a hydroxyl group, a cyano group, a substituted or unsubstituted C 1 -C 30 alkyl group, a substituted or unsubstituted C 2 -C 30 alkenyl group, a substituted or unsubstituted C 2 -C 30 alkynyl group, a substituted or unsubstituted C 1 -C 30 alkoxy group, a group represented by —(Ar 4 ) d —Ar 14 , and a group represented by —N[—(Ar 5 ) c —Ar 15 ][—(Ar 6 ) f —Ar 16 ];

wherein Ar 1 through Ar 6 are each independently selected from the group consisting of a substituted or unsubstituted C 1 -C 30 alkylene group, a substituted or unsubstituted C 2 -C 30 alkenylene group, a substituted or unsubstituted C 5 -C 30 arylene group, and a substituted or unsubstituted C 4 -C 30 heteroarylene group;

wherein Ar 11 through Ar 16 are each independently selected from the group consisting of a hydrogen atom, a halogen atom, a hydroxyl group, a cyano group, a substituted or unsubstituted C 1 -C 30 alkyl group, a substituted or unsubstituted C 2 -C 30 alkenyl group, a substituted or unsubstituted C 2 -C 30 alkynyl group, a substituted or unsubstituted C 1 -C 30 alkoxy group, a substituted or unsubstituted C 5 -C 30 aryl group, and a substituted or unsubstituted C 4 -C 30 heteroaryl group;

wherein a through f are each independently an integer from 0 to 10;

wherein the moieties represented by Ar 1 in the group represented by —(Ar 1 ) a —Ar 11 are identical to or different from each other, the moieties represented by Ar e in the group represented by —(Ar 2 ) b —Ar 12 are identical to or different from each other, the moieties represented by Ar 3 in the group represented by —(Ar 3 ) c —Ar 13 are identical to or different from each other, the moieties represented by Ar 4 in the group represented by —(Ar 4 ) d —Ar 14 are identical to or different from each other, the moieties represented by Ar 5 in the group represented by —(Ar 5 ) e —Ar 15 are identical to or different from each other, and the moieties represented by Ar 6 in the group represented by [—(Ar 6 ) f —Ar 16 ] are identical to or different from each other;

wherein X 1 and X 2 are each independently a divalent linking group selected from the group consisting of —C(Q 1 )(Q 2 )- and —N(Q 3 )-; and

wherein Q 1 through Q 3 are each independently selected from the group consisting of a hydrogen atom, a halogen atom, a hydroxyl group, a cyano group, a substituted or unsubstituted C 1 -C 30 alkyl group, a substituted or unsubstituted C 2 -C 30 alkenyl group, a substituted or unsubstituted C 2 -C 30 alkynyl group, a substituted or unsubstituted C 1 -C 30 alkoxy group, a substituted or unsubstituted C 5 -C 30 aryl group, and a substituted or unsubstituted C 4 -C 30 heteroaryl group.

2. The condensed-cyclic compound of claim 1 , wherein R 1 , R 2 R 3 R 4 , R 5 , R 6 , and R 7 are hydrogen;

R 8 is selected from the group consisting of a substituted or unsubstituted C 1 -C 10 alkyl group, a substituted or unsubstituted C 2 -C 10 alkenyl group, a substituted or unsubstituted C 2 -C 10 alkynyl group, a substituted or unsubstituted C 1 -C 10 alkoxy group, a group represented by —(Ar 1 ) a —Ar 11 , and a group represented by —N[—(Ar 2 ) b —Ar 12 ][—(Ar 3 ) c —Ar 13 ];

R 11 , R 12 , R 13 and R 14 are each independently selected from the group consisting of hydrogen, a substituted or unsubstituted C 1 -C 10 alkyl group, a substituted or unsubstituted C 2 -C 10 alkenyl group, a substituted or unsubstituted C 2 -C 10 alkynyl group, a substituted or unsubstituted C 1 -C 10 alkoxy group, a group represented by —(Ar 4 ) d —Ar 14 , and a group represented by —N[—(Ar 5 ) e —Ar 15 ][—(Ar 6 ) f —Ar 16 ];

Ar 1 , Ar 2 , Ar 3 , Ar 4 , Ar 5 and Ar 6 are each independently selected from the group consisting of a substituted or unsubstituted C 1 -C 30 alkylene group, a substituted or unsubstituted C 2 -C 30 alkenylene group, a substituted or unsubstituted C 5 -C 30 arylene group, and a substituted or unsubstituted C 4 -C 30 heteroarylene group; and

Ar 11 and Ar 16 are each independently selected from the group consisting of a hydrogen atom, a halogen atom, a hydroxyl group, a cyano group, a substituted or unsubstituted C 1 -C 30 alkyl group, a substituted or unsubstituted C 2 -C 30 alkenyl group, a substituted or unsubstituted C 2 -C 30 alkynyl group, a substituted or unsubstituted C 1 -C 30 alkoxy group, a substituted or unsubstituted C 5 -C 30 aryl group, and a substituted or unsubstituted C 4 -C 30 heteroaryl group.

3. The condensed-cyclic compound of claim 2 , wherein a, b, c, d, e and f are each independently 0, 1, or 2.

4. The condensed-cyclic compound of claim 2 , wherein Ar 1 , Ar 2 , Ar 3 , Ar 4 , Ar 5 and Ar 6 are each independently selected from the group consisting of a pyridinylene group, a quinolinylene group, a benzimidazolylene group, an imidazopyridinylene group, an imidazopyrimidinylene group, a phenylene group, a C 1 -C 10 alkyl phenylene group, a carbazolylene group, a phenylcarbazolylene group, a fluorenylene group, a C 1 -C 10 alkylfluorenylene group, a di(C 1 -C 10 alkyl)fluorenylene group, an ethylene group, and a naphthylene group.

5. The condensed-cyclic compound of claim 2 , wherein Ar 11 Ar 12 , Ar 13 , Ar 14 , Ar 15 and Ar 16 are each independently selected from the group consisting of a methyl group, ethyl, a propyl group, a butyl group, a methoxy group, an ethoxy group, a propoxy group, a butoxy group, a pyridinyl group, a quinolinyl group, a benzimidazolyl group, an imidazopyridinyl group, an imidazopyrimidinyl group, a phenyl group, a carbazolyl group, a fluorenyl group, a di(C 1 -C 10 alkyl)fluorenyl group, a naphthyl group, and a functional group prepresented by the formula

6. The condensed-cyclic compound of claim 2 , wherein R 8 is selected from the group consisting of functional groups represented by Formulae 3A through 3O below

and R 11 , R 12 , R 13 and R 14 are each independently selected from the group consisting of hydrogen and functional groups represented by Formulae 3A through 3O below:

wherein, in Formulae 3A through 3O, Z 1 and Z 2 are each independently selected from the group consisting of hydrogen, a methyl group, an ethyl group, a propyl group, a butyl group, a methoxy group, an ethoxy group, a propoxy group, a butoxy group, a phenyl group, and a naphthyl group.

7. The condensed-cyclic compound of claim 2 , wherein R8 is selected from the group consisting of functional groups represented by Formula 4A through 4R below

and R 11 R 12 , R 13 and R 14 are each independently selected from the group consisting of hydrogen and functional groups represented by Formulae 4A through 4R below:

8. The condensed-cyclic compound of claim 2 , wherein Q 1 through Q 3 are each independently selected from the group consisting of hydrogen, a C 1 -C 30 alkyl group, a C 1 -C 30 alkoxy group, a C 5 -C 14 aryl group, and a C 4 -C 14 heteroaryl group.

9. The condensed-cyclic compound of claim 1 , wherein R 8 is connected to * of Formula 2 and R 7 is connected to *′ of Formula 2 so as to be represented by Formula 1a below:

10. The condensed-cyclic compound of claim 9 , wherein R 1 R 2 , R 3 , R 4 , R 5 and R 6 are hydrogen;

R 11 R 12 , R 13 , R 14 R 21 R 22 , R 23 and R 24 are each independently selected from the group consisting of hydrogen, a substituted or unsubstituted C 1 -C 10 alkyl group, a substituted or unsubstituted C 2 -C 10 alkenyl group, a substituted or unsubstituted C 2 -C 10 alkynyl group, a substituted or unsubstituted C 1 -C 10 alkoxy group, a group represented by —(Ar 4 ) d —Ar 14 , and a group represented by —N[—(Ar 5 ) e —Ar 15 ][—(Ar 6 ) f —Ar 16 ];

Ar 4 , Ar 5 and Ar 6 are each independently selected from the group consisting of a substituted or unsubstituted C 1 -C 30 alkylene group, a substituted or unsubstituted C 2 -C 30 alkenylene group, a substituted or unsubstituted C 5 -C 30 arylene group, and a substituted or unsubstituted C 4 -C 30 heteroarylene group; and

Ar 14 and Ar 16 are each independently selected from the group consisting of a hydrogen atom, a halogen atom, a hydroxyl group, a cyano group, a substituted or unsubstituted C 1 -C 30 alkyl group, a substituted or unsubstituted C 2 -C 30 alkenyl group, a substituted or unsubstituted C 2 -C 30 alkynyl group, a substituted or unsubstituted C 1 -C 30 alkoxy group, a substituted or unsubstituted C 5 -C 30 aryl group, and a substituted or unsubstituted C 4 -C 30 heteroaryl group.

11. The condensed-cyclic compound of claim 9 , wherein d, e and f are each independently 0, 1, or 2.

12. The condensed-cyclic compound of claim 9 , Ar 4 , Ar 5 and Ar 6 are each independently selected from the group consisting of a pyridinylene group, a quinolinylene group, a benzimidazolylene group, an imidazopyridinylene group, an imidazopyrimidinylene group, a phenylene group, a C 1 -C 10 alkyl phenylene group, a carbazolylene group, a phenylcarbazolylene group, a fluorenylene group, a C 1 -C 10 alkyl fluorenylene group, a di(C 1 -C 10 alkyl) fluorenylene group, an ethylene group, and a naphthylene group.

13. The condensed-cyclic compound of claim 9 , wherein Ar 14 , Ar 15 and Ar 16 are each independently selected from the group consisting of a methyl group, an ethyl group, a propyl group, a butyl group, a methoxy group, an ethoxy group, a propoxy group, a butoxy group, a pyridinyl group, a quinolinyl group, a benzimidazolyl group, an imidazopyridinyl group, an imidazopyrimidinyl group, a phenyl group, a carbazolyl group, a fluorenyl group, di(C 1 -C 10 alkyl)fluorenyl group, a naphthyl group, and a functional group prepresented by the formula

14. The condensed-cyclic compound of claim 9 , wherein R 11 R 12 , R 13 , R 14 R 21 R 22 , R 23 and R 24 are each independently selected from the group consisting of hydrogen and functional groups represented by Formulae 3A through 3O below:

wherein, in Formulae 3A through 3O, Z 1 and Z 2 are each independently selected from the group consisting of hydrogen, a methyl group, an ethyl group, a propyl group, a butyl group, a methoxy group, an ethoxy group, a propoxy group, a butoxy group, a phenyl group, and a naphthyl group.

15. The condensed-cyclic compound of claim 9 , wherein R 11 R 12 , R 13 R 14 R 21 R 22 , R 23 and R 24 are each independently selected from the group consisting of hydrogen and functional groups represented by Formulae 4A through 4R below:

16. The condensed-cyclic compound of claim 9 , wherein Q 1 , Q 2 and Q 3 are each independently selected from the group consisting of hydrogen, a C 1 -C 30 alkyl group, a C 1 -C 30 alkoxy group, a C 5 -C 14 aryl group, and a C 4 -C 14 heteroaryl group.

17. A condensed-cyclic compound having the structure of compounds 1 to 6 and 13 to 43 below:

18. An organic light emitting diode comprising:

a first electrode;

a second electrode facing the first electrode; and

an organic layer disposed between the first electrode and the second electrode;

wherein the organic layer comprises the condensed-cyclic compound of claim 1 .

19. The organic light emitting diode of claim 18 , wherein the organic layer is a hole transport layer, an emissive layer, or an electron transport layer.

20. The organic light emitting diode of claim 18 , further comprising, between the first electrode and the second electrode, at least one layer selected from the group consisting of a hole injection layer, a hole transport layer, an emissive layer, a hole blocking layer, an electron transport layer, and an electron injection layer.

21. A condensed-cyclic compound represented by Formula 1 below:

wherein R 7 is selected from the group consisting of a hydrogen atom, a halogen atom, a hydroxyl group, a cyano group, a substituted or unsubstituted C 1 -C 30 alkyl group, a substituted or unsubstituted C 2 -C 30 alkenyl group, a substituted or unsubstituted C 2 -C 30 alkynyl group, a substituted or unsubstituted C1-C30 alkoxy group, a group represented by —(Ar 1 ) a —Ar 11 , and a group represented by —N[—(Ar 2 ) b —Ar 12 ][—(Ar 3 ) c —Ar 13 ] and R 8 is selected from the group consisting of a halogen atom, a hydroxyl group, a cyano group, a substituted or unsubstituted C 1 -C 30 alkyl group, a substituted or unsubstituted C 2 -C 30 alkenyl group, a substituted or unsubstituted C 2 -C 30 alkynyl group, a substituted or unsubstituted C 1 -C 30 alkoxy group, a group represented by —(Ar 1 ) a —Ar 11 , and a group represented by —N[—(Ar 2 ) b — Ar 12 ][—(Ar 3 ) c —Ar 13 ]; or R 8 is connected to * of Formula 2 and R 7 is connected to *′ of Formula 2 represented by:

wherein R 1 through R 6 , R 11 through R 14 , and R 21 through R 24 are each independently selected from the group consisting of a hydrogen atom, a halogen atom, a hydroxyl group, a cyano group, a substituted or unsubstituted C 1 -C 30 alkyl group, a substituted or unsubstituted C 2 -C 30 alkenyl group, a substituted or unsubstituted C 2 -C 30 alkynyl group, a substituted or unsubstituted C 1 -C 30 alkoxy group, a group represented by —(Ar 4 ) d —Ar 14 , and a group represented by —N[—(Ar 5 ) e —Ar 15 ][—(Ar 6 ) f —Ar 16 ];

wherein Ar 1 through Ar 6 are each independently selected from the group consisting of a substituted or unsubstituted C 1 -C 30 alkylene group, a substituted or unsubstituted C 2 -C 30 alkenylene group, a substituted or unsubstituted C 5 -C 30 arylene group, and a substituted or unsubstituted C 4 -C 30 heteroarylene group;

wherein Ar 11 is selected from the group consisting of a halogen atom, a hydroxyl group, a cyano group, a substituted or unsubstituted C 1 -C 30 alkyl group, a substituted or unsubstituted C 2 -C 30 alkenyl group, a substituted or unsubstituted C 2 -C 30 alkynyl group, a substituted or unsubstituted C 1 -C 30 alkoxy group, a substituted or unsubstituted C 5 -C 30 aryl group, and a substituted or unsubstituted C 4 -C 30 heteroaryl group;

wherein Ar 12 through Ar 16 are each independently selected from the group consisting of a hydrogen atom, a halogen atom, a hydroxyl group, a cyano group, a substituted or unsubstituted C 1 -C 30 alkyl group, a substituted or unsubstituted C 2 -C 30 alkenyl group, a substituted or unsubstituted C 2 -C 30 alkynyl group, a substituted or unsubstituted C 1 -C 30 alkoxy group, a substituted or unsubstituted C 5 -C 30 aryl group, and a substituted or unsubstituted C 4 -C 30 heteroaryl group;

wherein a through f are each independently an integer from 0 to 10;

wherein the moieties represented by Ar 1 in the group represented by —(Ar 1 ) a —Ar 11 are identical to or different from each other, the moieties represented by Ar 2 in the group represented by —(Ar 2 ) b —Ar 12 are identical to or different from each other, the moieties represented by Ar 3 in the group represented by —(Ar 3 ) c —Ar 13 are identical to or different from each other, the moieties represented by Ar 4 in the group represented by —(Ar 4 ) d —Ar 14 are identical to or different from each other, the moieties represented by Ar 5 in the group represented by —(Ar 5 ) e —Ar 15 are identical to or different from each other, and the moieties represented by Ar 6 in the group represented by [—(Ar 6 ) f —Ar 16 ] are identical to or different from each other;

wherein X 1 and X 2 are each independently a divalent linking group selected from the group consisting of —C(Q 1 )(Q 2 )- and —N(Q 3 )-; and

wherein Q 1 through Q 3 are each independently selected from the group consisting of a hydrogen atom, a halogen atom, a hydroxyl group, a cyano group, a substituted or unsubstituted C 1 -C 30 alkyl group, a substituted or unsubstituted C 2 -C 30 alkenyl group, a substituted or unsubstituted C 2 -C 30 alkynyl group, a substituted or unsubstituted C 1 -C 30 alkoxy group, a substituted or unsubstituted C 5 -C 30 aryl group, and a substituted or unsubstituted heteroaryl group.