Condensed-cyclic compound and organic light emitting device including the same

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

wherein, in Formula 1,

Ar 11 is represented by one of Formulae 10-1 to 10-4:

wherein, in Formulae 1 and 10-1 to 10-4,

X 1 is N or C(R 1 ), X 2 is N or C(R 2 ), X 3 is N or C(R 3 ), X 4 is N or C(R 4 ), X 5 is N or C(R 5 ), X 6 is N or C(R 6 ), X 7 is N or C(R 7 ), X 8 is N or C(R 8 ), X 11 is N or C(R 11 ), X 12 is N or C(R 12 ), X 13 is N or C(R 13 ), X 14 is N or C(R 14 ), X 15 is N or C(R 15 ), X 16 is N or C(R 16 ), X 17 is N or C(R 17 ), and X 18 is N or C(R 18 );

Y 11 is O, S, N(R 101 ), C(R 101 )(R 102 ), or Si(R 101 )(R 102 );

Z 11 is selected from N and C(A 12 );

Z 12 to Z 14 are each independently selected from C(A 11 ) and C(A 12 ); and at least one of Z 12 to Z 14 is C(A 11 ); and

A 11 comprises at least one cyano group (CN); and A 11 is represented by one of Formulae 2-1 to 2-10:

wherein, in Formulae 2-1 to 2-10,

X 21 is N or C(R 21 ), X 22 is N or C(R 22 ), X 23 is N or C(R 23 ), X 24 is N or C(R 24 ), and X 25 is N or C(R 25 );

A 12 , R 1 to R 8 , R 11 to R 18 , R 101 , R 102 , R 21 to R 25 , and R 201 to R 203 are each independently selected from

a hydrogen, a deuterium, —F, a hydroxyl group, a cyano group (CN), a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C 1 -C 20 alkyl group, and a C 1 -C 20 alkoxy group;

a C 1 -C 20 alkyl group and a C 1 -C 20 alkoxy group, each substituted with at least one selected from a deuterium, —F, a hydroxyl group, a cyano group (CN), a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, and a phosphoric acid group or a salt thereof;

a phenyl group, a pyridinyl group, a fluorenyl group, a dibenzofuranyl group, and a dibenzothiophenyl group;

a phenyl group, a pyridinyl group, a fluorenyl group, a dibenzofuranyl group, and a dibenzothiophenyl group, each substituted with at least one selected from a deuterium, —F, a hydroxyl group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C 1 -C 20 alkyl group, a C 1 -C 20 alkoxy group, a phenyl group, a pyridinyl group, a fluorenyl group, a dibenzofuranyl group, a dibenzothiophenyl group, and —Si(Q 1 )(Q 2 )(Q 3 ); and

—Si(Q 11 )(Q 12 )(Q 13 ),

b201 is selected from 1, 2, 3, 4, and 5;

b202 and b203 are each independently selected from 1, 2, 3, and 4; and

* indicates a carbon atom in Formula 1,

wherein Q 1 to Q 3 and Q 11 to Q 13 are each independently selected from a hydrogen, a C 1 -C 20 alkyl group, a C 1 -C 20 alkoxy group, a phenyl group, a naphthyl group, a pyridinyl group, a fluorenyl group, a dibenzofuranyl group, and a dibenzothiophenyl group.

2. The condensed-cyclic compound of claim 1 , wherein X 1 is N, X 2 is C(R 2 ), X 3 is C(R 3 ), X 4 is C(R 4 ), X 5 is C(R 5 ), X 6 is C(R 6 ), X 7 is C(R 7 ), X 8 is C(R 8 ), X 11 is C(R 11 ), X 12 is C(R 12 ), X 13 is C(R 13 ), X 14 is C(R 14 ), X 15 is C(R 15 ), X 16 is C(R 16 ), X 17 is C(R 17 ), and X 18 is C(R 18 );

X 1 is C(R 1 ), X 2 is N, X 3 is C(R 3 ), X 4 is C(R 4 ), X 5 iS C(R 5 ), X 6 is C(R 6 ), X 7 is C(R 7 ), X 8 is C(R 8 ), X 11 is C(R 11 ), X 12 is C(R 12 ), X 13 is C(R 13 ), X 14 is C(R 14 ), X 15 is C(R 15 ), X 16 is C(R 16 ), X 17 is C(R 17 ), and X 18 is C(R 18 );

X 1 is C(R 1 ), X 2 is C(R 2 ), X 3 is N, X 4 is C(R 4 ), X 5 is C(R 5 ), X 6 is C(R 6 ), X 7 is C(R 7 ), X 8 is C(R 8 ), X 11 is C(R 11 ), X 12 is C(R 12 ), X 13 is C(R 13 ), X 14 is C(R 14 ), X 15 is C(R 15 ), X 16 is C(R 16 ), X 17 is C(R 17 ), and X 18 is C(R 18 );

X 1 is C(R 1 ), X 2 is C(R 2 ), X 3 is C(R 3 ), X 4 is N, X 5 is C(R 5 ), X 6 is C(R 6 ), X 7 is C(R 7 ), X 8 is C(R 8 ), X 11 is C(R 11 ), X 12 is C(R 12 ), X 13 is C(R 13 ), X 14 is C(R 14 ), X 15 is C(R 15 ), X 16 C(R 16 ), X 17 is C(R 17 ), and X 18 is C(R 18 )

X 1 is C(R 1 ), X 2 is C(R 2 ), X 3 is C(R 3 ), X 4 is C(R 4 ), X 5 is N, X 6 is C(R 6 ), X 7 is C(R 7 ), X 8 is C(R 8 ), X 11 is C(R 11 ), X 12 is C(R 12 ), X 13 is C(R 13 ), X 14 is C(R 14 ), X 15 is C(R 15 ), X 16 is C(R 16 ), X 17 is C(R 17 ), and X 18 is C(R 18 );

X 1 is C(R 1 ), X 2 is C(R 2 ), X 3 is C(R 3 ), X 4 is C(R 4 ), X 5 is C(R 5 ), X 6 is N, X 7 is C(R 7 ), X 8 is C(R 8 ), X 11 is C(R 11 ), X 12 is C(R 12 ), X 13 is C(R 13 ), X 14 is C(R 14 ), X 15 is C(R 15 ), X 16 is C(R 16 ), X 17 is C(R 17 ), and X 18 is C(R 18 );

X 1 is C(R 1 ), X 2 is C(R 2 ), X 3 is C(R 3 ), X 4 is C(R 4 ), X 5 is C(R 5 ), X 6 is C(R 6 ), X 7 is N, X 8 is C(R 8 ), X 11 is C(R 11 ), X 12 is C(R 12 ), X 13 is C(R 13 ), X 14 is C(R 14 ), X 15 is C(R 15 ), X 16 is C(R 16 ), X 17 is C(R 17 ), and X 18 is C(R 18 );

X 1 is C(R 1 ), X 2 is C(R 2 ), X 3 is C(R 3 ), X 4 is C(R 4 ), X 5 is C(R 5 ), X 6 is C(R 6 ), X 7 is C(R 7 ), X 8 is N, X 11 is C(R 11 ), X 12 is C(R 12 ), X 13 is C(R 13 ), X 14 is C(R 14 ), X 15 is C(R 15 ), X 16 is C(R 16 ), X 17 is C(R 17 ), and X 18 is C(R 18 ); or

X 1 is C(R 1 ), X 2 is C(R 2 ), X 3 is C(R 3 ), X 4 is C(R 4 ), X 5 is C(R 5 ), X 6 is C(R 6 ), X 7 is C(R 7 ), X 8 is C(R 8 ), X 11 is C(R 11 ), X 12 is C(R 12 ), X 13 is C(R 13 ), X 14 is C(R 14 ), X 15 is C(R 15 ), X 16 is C(R 16 ), X 17 is C(R 17 ), and X 18 is C(R 18 ).

3. The condensed-cyclic compound of claim 1 , wherein Y 11 is O, S, or N(R 101 ).

4. The condensed-cyclic compound of claim 1 , wherein

Z 11 is N, Z 12 is C(A 12 ), Z 13 is C(A 11 ), and Z 14 is C(A 12 ); or

Z 11 is C(A 12 ), Z 12 is C(A 12 ), Z 13 is C(A 11 ), and Z 14 is C(A 12 ).

5. The condensed-cyclic compound of claim 1 , wherein A 11 is represented by one of Formulae 2-1 to 2-7.

6. The condensed-cyclic compound of claim 1 , wherein A 11 is represented by one of Formulae 3-1 to 3-110:

wherein, in Formulae 3-1 to 3-110,

* indicates a carbon atom in Formula 1, and

X 21 to X 25 , R 21 to R 25 , R 202 , R 203 , b202, and b203 are the same as in Formulae 2-1to 2-10.

7. The condensed-cyclic compound of claim 1 , wherein A 11 is represented by one of Formulae 4-1 to 4-110:

wherein, in Formulae 4-1 to 4-110,

* indicates a carbon atom in Formula 1, and

R 202 , R 203 , b202, and b203 are the same as in Formulae 2-1 to 2-10.

8. The condensed-cyclic compound of claim 1 , wherein

A 12 is selected from a hydrogen, a deuterium, —F, a hydroxyl group, a cyano group (CN), a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C 1 -C 20 alkyl group, and a C 1 -C 20 alkoxy group;

a phenyl group, a pyridinyl group, a fluorenyl group, a dibenzofuranyl group, and a dibenzothiophenyl group; and

—Si(Q 31 )(Q 32 )(Q 33 ),

wherein Q 31 to Q 33 are each independently selected from a C 1 -C 10 alkyl group, a C 1 -C 10 alkoxy group, a phenyl group, a naphthyl group, and a pyridinyl group.

9. The condensed-cyclic compound of claim 1 , wherein

R 1 to R 8 , R 11 to R 18 , R 101 , R 102 , R 21 to R 25 , and R 201 to R 203 are each independently selected from

a hydrogen, a deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a methyl group, an ethyl group, an n-propyl group, an iso-propyl group, an n-butyl group, an isobutyl group, a sec-butyl group, a tert-butyl group, an n-pentyl group, an isopentyl group, a sec-pentyl group, a tert-pentyl group, an n-hexyl group, an iso-hexyl group, a sec-hexyl group, a tert-hexyl group, an n-heptyl group, an iso-heptyl group, a sec-heptyl group, a tert-heptyl group, an n-octyl group, an iso-octyl group, a sec-octyl group, a tert-octyl group, an n-nonyl group, an iso-nonyl group, a sec-nonyl group, a tert-nonyl group, an n-decyl group, an iso-decyl group, a sec-decyl group, a tert-decyl group, a methoxy group, an ethoxy group, a propoxy group, a butoxy group, a pentoxy group, a phenyl group, a pyridinyl group, a fluorenyl group, a dibenzofuranyl group, and a dibenzothiophenyl group;

a methyl group, an ethyl group, an n-propyl group, an iso-propyl group, an n-butyl group, an isobutyl group, a sec-butyl group, a tert-butyl group, an n-pentyl group, an isopentyl group, a sec-pentyl group, a tert-pentyl group, an n-hexyl group, an iso-hexyl group, a sec-hexyl group, a tert-hexyl group, an n-heptyl group, an iso-heptyl group, a sec-heptyl group, a tert-heptyl group, an n-octyl group, an iso-octyl group, a sec-octyl group, a tert-octyl group, an n-nonyl group, an iso-nonyl group, a sec-nonyl group, a tert-nonyl group, an n-decyl group, an iso-decyl group, a sec-decyl group, a tert-decyl group, a methoxy group, an ethoxy group, a propoxy group, a butoxy group, a pentoxy group, a phenyl group, a pyridinyl group, a fluorenyl group, a dibenzofuranyl group, and a dibenzothiophenyl group, each substituted with at least one selected from a deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, and a phosphoric acid group or a salt thereof; and

—Si(Q 11 )(Q 12 )(Q 13 ),

wherein Q 11 to Q 13 are each independently selected from a hydrogen, a C 1 -C 20 alkyl group, a C 1 -C 20 alkoxy group, a phenyl group, a naphthyl group, a pyridinyl group, a fluorenyl group, a dibenzofuranyl group, and a dibenzothiophenyl group.

10. The condensed-cyclic compound of claim 1 , wherein

R 1 to R 8 , R 11 to R 18 , R 101 , R 102 , R 21 to R 25 , and R 201 to R 203 are each independently selected from

a hydrogen, a deuterium, a cyano group, a methyl group, an ethyl group, an n-propyl group, an iso-propyl group, an n-butyl group, an isobutyl group, a sec-butyl group, a tert-butyl group, an n-pentyl group, an isopentyl group, a sec-pentyl group, a tert-pentyl group, an n-hexyl group, an iso-hexyl group, a sec-hexyl group, a tert-hexyl group and —Si(Q 11 )(Q 12 )(Q 13 ),

wherein Q 11 to Q 13 are each independently selected from a hydrogen, a C 1 -C 20 alkyl group, a C 1 -C 20 alkoxy group, and a phenyl group.

11. The condensed-cyclic compound of claim 1 , wherein at least one of X 3 , X 6 , X 13 , and X 16 is C(CN).

12. The condensed-cyclic compound of claim 1 , wherein

X 3 is C(CN); or

X 3 and X 6 are C(CN).

13. The condensed-cyclic compound of claim 1 , wherein R 1 , R 2 , R 4 , R 5 , R 7 , R 8 , R 11 , R 12 , R 14 , R 15 , R 17 , and R 18 are not a cyano group.

14. The condensed-cyclic compound of claim 1 , wherein the condensed-cyclic compound represented by Formula 1 is represented by one of Formulae 1-1 to 1-8:

wherein, in Formulae 1-1 to 1-8,

X 1 to X 8 and A 11 are the same as in Formula 1;

X 11 to X 18 and Y 11 are the same as in Formulae 10-1 to 10-4; and

A 12a , A 12b , and A 12c are each independently the same as A 12 in Formula 1.

15. The condensed-cyclic compound of claim 1 , wherein the condensed-cyclic compound represented by Formula 1 is represented by one of Formulae 1-11 to 1-18, 1-21 to 1-28, and 1-31 to 1-38:

wherein, in Formulae 1-11 to 1-18, 1-21 to 1-28, and 1-31 to 1-38,

A 11 is the same as in Formula 1;

Y 11 is the same as in Formulae 10-1 to 10-4; and

A 12a , A 12b , and A 12c are each independently the same as A 12 in Formula 1.

16. The condensed-cyclic compound of claim 1 , wherein the condensed-cyclic compound represented by Formula 1 is represented by one of Formulae 1-41 to 1-48, 1-51 to 1-58, and 1-61 to 1-68:

wherein, in Formulae 1-41 to 1-48, 1-51 to 1-58, and 1-61 to 1-68,

A 11 is the same as in Formula 1; and

Y 11 is the same as in Formulae 10-1 to 10-4.

17. The condensed-cyclic compound of claim 1 , wherein the condensed-cyclic compound represented by Formula 1 is selected from Compounds 1 to 90:

18. An organic light-emitting device comprising:

a first electrode;

a second electrode; and

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

wherein the organic layer comprises an emission layer and at least one condensed-cyclic compound of Formula 1 of claim 1 .

19. The organic light-emitting device of claim 18 , wherein the emission layer comprises the at least one condensed-cyclic compound of Formula 1.

20. The organic light-emitting device of claim 19 , wherein the emission layer further comprises a phosphorescent dopant.