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

1. A condensed cyclic compound for an organic light-emitting device represented by Formula 1:

wherein in Formula 1,

X is an oxygen atom (O) or a sulfur (S) atom;

one selected from Y 1 and Y 2 is a nitrogen (N) atom and the other of Y 1 and Y 2 is a nitrogen (N) atom or —CR 6 ;

C 1 and C 2 are each a carbon (C) atom;

ring A is a benzene ring represented by Formula 1A, wherein 3 to 6 in Formula 1A are reference numbers and two of the reference numbers 3 to 6 correspond to respective carbon atoms of the ring B;

the ring B is an indole ring represented by Formula 1B, wherein 7 and 8 in Formula 1B are reference numbers, each of which corresponds to a carbon atom of the ring A;

R 1 to R 13 are each independently selected from a hydrogen atom, a deuterium atom, a halogen atom, 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 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 substituted or unsubstituted C 3 -C 10 cycloalkyl group, a substituted or unsubstituted C 3 -C 10 cycloalkenyl group, a substituted or unsubstituted C 3 -C 10 heterocycloalkyl group, a substituted or unsubstituted C 3 -C 10 heterocycloalkenyl group, a substituted or unsubstituted C 6 -C 30 aryl group, a substituted or unsubstituted C 2 -C 30 heteroaryl group, a substituted or unsubstituted C 6 -C 30 aryloxy group, a substituted or unsubstituted C 6 -C 30 arylthio group, a monovalent C 6 -C 30 non-aromatic condensed polycyclic group, —Si(Q 1 )(Q 2 )(Q 3 ), and —B(Q 4 )(Q 5 ),

at least one substituent of the C 1 -C 10 substituted alkyl group, the substituted C 2 -C 10 alkenyl group, the substituted C 2 -C 10 alkynyl group, the substituted C 1 -C 10 alkoxy group, the substituted C 3 -C 10 cycloalkyl group, the substituted C 3 -C 10 cycloalkenyl group, the substituted C 3 -C 10 heterocycloalkyl group, the substituted C 3 -C 10 heterocycloalkenyl group, the substituted C 6 -C 30 aryl group, the substituted C 2 -C 30 heteroaryl group, the substituted C 6 -C 30 aryloxy group, and the substituted C 6 -C 30 arylthio group is selected from:

a deuterium atom, a halogen atom, 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 C 1 -C 30 alkyl group, a C 2 -C 30 alkenyl group, a C 2 -C 30 alkynyl group, and a C 1 -C 30 alkoxy group;

a C 1 -C 30 alkyl group, a C 2 -C 30 alkenyl group, a C 2 -C 30 alkynyl group, and a C 1 -C 30 alkoxy group, each substituted with at least one selected from a deuterium atom, a halogen atom, 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 C 3 -C 10 cycloalkyl group, a C 3 -C 10 heterocycloalkyl group, a C 3 -C 10 cycloalkenyl group, a C 3 -C 10 heterocycloalkenyl group, a C 6 -C 30 aryl group, a C 2 -C 30 heteroaryl group, a C 6 -C 30 aryloxy group, a C 6 -C 30 arylthio group, a monovalent C 6 -C 30 non-aromatic condensed polycyclic group, —N(Q 11 )(Q 12 ), —Si(Q 13 )(Q 14 )(Q 15 ), and —B(Q 16 )(Q 17 );

a C 3 -C 10 cycloalkyl group, a C 3 -C 10 cycloalkenyl group, a C 3 -C 10 heterocycloalkyl group, a C 3 -C 10 heterocycloalkenyl group, a C 6 -C 30 aryl group, a C 2 -C 30 heteroaryl group, a C 6 -C 30 aryloxy group, a C 6 -C 30 arylthio group, and a monovalent C 2 -C 30 non-aromatic condensed polycyclic group;

a C 3 -C 10 cycloalkyl group, a C 3 -C 10 cycloalkenyl group, a C 3 -C 10 heterocycloalkyl group, a C 3 -C 10 heterocycloalkenyl group, a C 6 -C 30 aryl group, a C 2 -C 30 heteroaryl group, a C 6 -C 30 aryloxy group, a C 6 -C 30 arylthio group, and a monovalent C 6 -C 30 non-aromatic condensed polycyclic group, each substituted with at least one selected from a deuterium atom, a halogen atom, 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 C 1 -C 30 alkyl group, a C 2 -C 30 alkenyl group, a C 2 -C 30 alkynyl group, a C 1 -C 30 alkoxy group, a C 3 -C 10 cycloalkyl group, a C 3 -C 10 heterocycloalkyl group, a C 3 -C 10 cycloalkenyl group, a C 3 -C 10 heterocycloalkenyl group, a C 6 -C 30 aryl group, a C 2 -C 30 heteroaryl group, a C 6 -C 30 aryloxy group, a C 6 -C 30 arylthio group, a monovalent C 6 -C 30 non-aromatic condensed polycyclic group, —N(Q 21 )(Q 22 ), —Si(Q 23 )(Q 24 )(Q 25 ), and —B(Q 26 )(Q 27 ); and

Si(Q 31 )(Q 32 )(Q 33 ) and —B(Q 34 )(Q 35 ), and

Q 1 to Q 5 , Q 11 to Q 17 , Q 21 to Q 27 , and Q 31 to Q 35 are each independently selected from a hydrogen atom, a C 1 -C 30 alkyl group, a C 2 -C 30 alkenyl group, a C 2 -C 30 alkynyl group, a C 1 -C 30 alkoxy group, a C 3 -C 10 cycloalkyl group, a C 3 -C 10 heterocycloalkyl group, a C 3 -C 10 cycloalkenyl group, a C 3 -C 10 heterocycloalkenyl group, a C 6 -C 30 aryl group, a C 2 -C 30 heteroaryl group, and a monovalent C 6 -C 30 non-aromatic condensed polycyclic group.

2. The condensed cyclic compound of claim 1 , wherein the carbon atoms corresponding to the reference numbers 3 and 4 of the ring A are present in the ring B, the carbon atoms corresponding to the reference numbers 4 and 5 of the ring A, or the carbon atoms corresponding to the reference numbers 5 and 6 of the ring A.

3. The condensed cyclic compound of claim 1 , wherein the rings A and B

are a group represented by any one of Formulae 2A to 2F:

wherein in Formulae 2A to 2F,

R 7 to R 13 are each independently selected from a hydrogen atom, a substituted or unsubstituted C 6 -C 30 aryl group, and a substituted or unsubstituted C 2 -C 30 heteroaryl group,

at least one substituent of the substituted C 6 -C 30 aryl group and the substituted C 2 -C 30 heteroaryl group is selected from a C 6 -C 30 aryl group and a C 2 -C 30 heteroaryl group, and

R 13 is not a hydrogen atom.

4. The condensed cyclic compound of claim 1 , wherein

R 1 to R 13 are each independently selected from:

a hydrogen atom, a methyl group, an ethyl group, a propyl group, a butyl group, a pentyl group, a hexyl group, a heptyl group, an octyl group, a nonyl group, a decyl group, a phenyl group, a pentalenyl group, an indenyl group, a naphthyl group, an azulenyl group, an indacenyl group, an acenaphthyl group, a biphenyl group, a heptalenyl group, a phenalenyl group, a fluorenyl group, a phenanthrenyl group, an anthryl function, a fluoranthenyl group, a pyrenyl group, a benzofluorenyl group, a naphthacenyl group, a chrysenyl group, a triphenylenyl group, a terphenyl group, a perylenyl group, a picenyl group, a hexacenyl group, a spiro-fluorenyl group, a pyrrolyl group, a furyl group, a pyrazolyl group, an imidazolyl group, an oxazolyl group, an isoxazolyl group, a triazolyl group, a tetrazolyl group, an oxadiazolyl group, a pyridyl group, a pyrimidinyl group, a pyrazinyl group, a pyridazinyl group, a triazinyl group, a pyranyl group, a thiophenyl group, a thiazolyl group, an isothiazolyl group, a thiopyranyl group, an indolyl group, an isoindolyl group, an indolizinyl group, a benzofuryl group, an isobenzofuryl group, an indazolyl group, a benzimidazolyl group, a benzoxazolyl group, a benzisoxazolyl group, an imidazopyridyl group, a purinyl group, a quinolyl group, an isoquinolyl group, a phthalazinyl group, a quinazolinyl group, a quinoxalinyl group, a naphthyridinyl group, a cinnolinyl group, a benzothiophenyl group, a benzothiazolyl group, a carbazolyl group, a benzocarbazolyl group, a pyridoindolyl group, a dibenzofuryl group, a phenanthridinyl group, a benzoquinolyl group, a phenazinyl group, a dibenzosilolyl group, a dibenzothiophenyl group, and a benzocarbazolyl group;

a methyl group, an ethyl group, a propyl group, a butyl group, a pentyl group, a hexyl group, a heptyl group, an octyl group, a nonyl group, and a decyl group, each substituted with at least one selected from a deuterium atom, a halogen atom, a hydroxyl group, a cyano group, a nitro group, and an amino group; and

a phenyl group, a pentalenyl group, an indenyl group, a naphthyl group, an azulenyl group, an indacenyl group, an acenaphthyl group, a biphenyl group, a heptalenyl group, a phenalenyl group, a fluorenyl group, a phenanthrenyl group, an anthryl function, a fluoranthenyl group, a pyrenyl group, a benzofluorenyl group, a naphthacenyl group, a chrysenyl group, a triphenylenyl group, a terphenyl group, a perylenyl group, a picenyl group, a hexacenyl group, a spiro-fluorenyl group, a pyrrolyl group, a furyl group, a pyrazolyl group, an imidazolyl group, an oxazolyl group, an isoxazolyl group, a triazolyl group, a tetrazolyl group, an oxadiazolyl group, a pyridyl group, a pyrimidinyl group, a pyrazinyl group, a pyridazinyl group, a triazinyl group, pyranyl group, a thiophenyl group, a thiazolyl group, an isothiazolyl group, a thiopyranyl group, an indolyl group, an isoindolyl group, an indolizinyl group, a benzofuryl group, an isobenzofuryl group, an indazolyl group, a benzimidazolyl group, a benzoxazolyl group, a benzisoxazolyl group, an imidazopyridyl group, a purinyl group, a quinolyl group, an isoquinolyl group, a phthalazinyl group, a quinazolinyl group, a quinoxalinyl group, a naphthyridinyl group, a cinnolinyl group, a benzothiophenyl group, a benzothiazolyl group, a carbazolyl group, a benzocarbazolyl group, a pyridoindolyl group, a dibenzofuryl group, a phenanthridinyl group, a benzoquinolyl group, a phenazinyl group, a dibenzosilolyl group, a dibenzothiophenyl group, and a benzocarbazolyl group, each substituted with at least one selected from a deuterium atom, a halogen atom, a hydroxyl group, a cyano group, a nitro group, an amino 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 C 1 -C 10 alkyl group, a C 2 -C 10 alkenyl group, a C 2 -C 10 alkynyl group, a C 1 -C 10 alkoxy group, a C 3 -C 10 cycloalkyl group, a C 3 -C 10 heterocycloalkyl group, a C 3 -C 10 cycloalkenyl group, C 3 -C 10 heterocycloalkenyl group, a C 6 -C 30 aryl group, a C 4 -C 30 heteroaryl group, a C 5 -C 30 aryloxy group, a C 5 -C 30 arylthio group, and —Si(Q 31 )(Q 32 )(Q 33 ) (wherein, Q 31 to Q 33 are each independently selected from a hydrogen atom, a C 1 -C 10 alkyl group, a C 1 -C 10 alkoxy group, and a C 6 -C 20 aryl group), wherein R 5 and R 13 are not hydrogen.

5. The condensed cyclic compound of claim 1 , wherein

R 1 to R 4 and R 6 to R 12 are each independently a hydrogen atom or a compound represented by one of Formulae 3A to 3C, and

R 5 and R 13 are each independently selected from a compound represented by one of Formulae 3A to 3C:

wherein in Formulae 3A to 3C,

Z 11 is selected from a deuterium atom, a halogen atom, 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 C 1 -C 10 alkyl group, a C 1 -C 10 alkoxy group, a C 6 -C 30 aryl group, a C 4 -C 30 heteroaryl group, and —Si(Q 31 )(Q 32 )(Q 33 ) (wherein Q 31 to Q 33 are each independently selected from a hydrogen atom, a C 1 -C 10 alkyl group, a C 1 -C 10 alkoxy group, and a C 6 -C 20 aryl group),

p1 is selected from an integer of 1 to 5,

p2 is selected from an integer of 1 to 4,

p3 is selected from an integer of 1 to 3, and

* is a binding site.

6. The condensed cyclic compound of claim 1 , wherein:

R 1 to R 4 and R 6 to R 12 are each independently a hydrogen atom or a compound represented by one of Formulae 4A to 4M, and

R 5 and R 13 are each independently a compound represented by one of Formulae 4A to 4M:

7. The condensed cyclic compound of claim 1 , wherein X is a sulfur (S) atom, Y 1 is a nitrogen (N) atom, and Y 2 is —CR 6 .

8. The condensed cyclic compound of claim 1 , wherein X is a S atom, Y 1 is —CR 6 , and Y 2 is a N atom.

9. The condensed cyclic compound of claim 1 , wherein X is an oxygen (O) atom, Y 1 is a N atom, and Y 2 is —CR 6 .

10. The condensed cyclic compound of claim 1 , wherein X is an O atom, Y 1 is CR 6 , and Y 2 is a N atom.

11. The condensed cyclic compound of claim 1 , wherein the condensed cyclic compound of Formula 1 is represented by Formulae 1-1 to 1-6:

12. The condensed cyclic compound of claim 11 , wherein:

R 1 to R 4 and R 6 to R 12 are each independently selected from a hydrogen atom, a phenyl group, a pyridyl group, and a pyrimidinyl group; a phenyl group, a pyridyl group, and a pyrimidinyl group, each substituted with at least one selected from a phenyl group, a pyridyl group, a pyrimidinyl group, and a carbazolyl group, and

R 5 and R 13 are each independently selected from a phenyl group, a pyridyl group, and a pyrimidinyl group; a phenyl group, a pyridyl group, and a pyrimidinyl group, each substituted with at least one selected from a phenyl group, a pyridyl group, a pyrimidinyl group, and a carbazolyl group.

13. The condensed cyclic compound of claim 1 , wherein the condensed cyclic compound is any one of Compounds 1 to 159:

14. The condensed cyclic compound of claim 1 , wherein the condensed cyclic compound is any one of Compounds 1, 7, 29, 59, 70, 88, 101, 112, 133, 149, 152, 155, and 159:

15. An organic light-emitting device comprising:

a first electrode;

a second electrode facing the first electrode; and

an organic layer between the first and second electrodes and comprising an emission layer,

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

16. The organic light-emitting device of claim 15 , wherein the organic layer comprises:

a hole transport region between the first electrode and the emission layer; and

an electron transport region between the emission layer and the second electrode.

17. The organic light-emitting device of claim 16 , wherein the electron transport region comprises at least one selected from a hole blocking layer, an electron transport layer, and an electron injection layer.

18. The organic light-emitting device of claim 16 , wherein the hole transport region comprises at least one selected from an electron blocking layer, a hole transport layer, and a hole injection layer.

19. The organic light-emitting device of claim 16 , wherein the emission layer comprises the condensed cyclic compound.

20. The organic light-emitting device of claim 16 , wherein the electron transport region comprises the condensed cyclic compound.