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

1. A condensed cyclic compound represented by Formula 1:

wherein, in Formulae 1, 2-1 to 2-3, 3-1 to 3-5, 4-1, and 4-2,

Y 11 is a group represented by Formulae 2-1 to 2-3,

Y 12 is a group represented by Formulae 3-1 to 3-5, 4-1, or 4-2,

X 21 is N or C(R 23 ),

X 22 is N(R 24 ), C(R 24 )(R 25 ), O, or S,

X 31 is N or C(R 31 ), X 32 is N or C(R 32 ), X 33 is N or C(R 33 ), X 34 is N or C(R 34 ), X 35 is N or C(R 35 ), X 36 is N or C(R 36 ), X 37 is N or C(R 37 ), and X 38 is N or C(R 38 ), wherein at least one X 31 to X 35 in Formula 3-1 is N, and at least one X 36 to X 38 in Formulae 3-2 to 3-5 is N,

Y 31 is O or S,

X 41 is O, S, N(R 43 ), or C(R 43 )(R 44 ),

ring A 21 , ring A 22 , ring A 41 , and ring A 42 are each independently a C 5 -C 60 carbocyclic group or a C 2 -C 60 heterocyclic group,

R 11 to R 14 are each independently hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, 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 1 -C 60 alkoxy group, a substituted or unsubstituted C 3 -C 10 cycloalkyl group, a substituted or unsubstituted C 1 -C 10 heterocycloalkyl group, a substituted or unsubstituted C 3 -C 10 cycloalkenyl group, a substituted or unsubstituted C 1 -C 10 heterocycloalkenyl group, a substituted or unsubstituted C 6 -C 60 aryl group, a substituted or unsubstituted C 7 -C 60 alkylaryl group, a substituted or unsubstituted C 6 -C 60 aryloxy group, a substituted or unsubstituted C 6 -C 60 arylthio group, a substituted or unsubstituted C 1 -C 60 heteroaryl group, a substituted or unsubstituted C 2 -C 60 alkylheteroaryl group, a substituted or unsubstituted C 1 -C 60 heteroaryloxy group, a substituted or unsubstituted C 1 -C 60 heteroarylthio group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, —Si(Q 1 )(Q 2 )(Q 3 ), —B(Q 1 )(Q 2 ), —N(Q 1 )(Q 2 ), —P(Q 1 )(Q 2 ), —C(═O)(Q 1 ), —S(═O)(Q 1 ), —S(═O) 2 (Q 1 ), —P(═O)(Q 1 )(Q 2 ), or —P(═S)(Q 1 )(Q 2 ),

R 21 to R 25 , R 31 to R 39 , and R 41 to R 44 are each independently hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, 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 1 -C 60 alkoxy group, a substituted or unsubstituted C 3 -C 10 cycloalkyl group, a substituted or unsubstituted C 1 -C 10 heterocycloalkyl group, a substituted or unsubstituted C 3 -C 10 cycloalkenyl group, a substituted or unsubstituted C 1 -C 10 heterocycloalkenyl group, a substituted or unsubstituted C 6 -C 60 aryl group, a substituted or unsubstituted C 7 -C 60 alkylaryl group, a substituted or unsubstituted C 6 -C 60 aryloxy group, a substituted or unsubstituted C 6 -C 60 arylthio group, a substituted or unsubstituted C 1 -C 60 heteroaryl group, a substituted or unsubstituted C 2 -C 60 alkylheteroaryl group, a substituted or unsubstituted C 1 -C 60 heteroaryloxy group, a substituted or unsubstituted C 1 -C 60 heteroarylthio group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, —Si(Q 1 )(Q 2 )(Q 3 ), —B(Q 1 )(Q 2 ), —N(Q 1 )(Q 2 ), —P(Q 1 )(Q 2 ), —C(═O)(Q 1 ), —S(═O)(Q 1 ), —S(═O) 2 (Q 1 ), —P(═O)(Q 1 )(Q 2 ), or —P(═S)(Q 1 )(Q 2 ),

b21, b22, b39, b41, and b42 are each independently 1, 2, 3, 4, 5, 6, 7, 8, 9, or 10,

Q 1 to Q 3 are each independently hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, a C 1 -C 60 alkyl group, a C 2 -C 60 alkenyl group, a C 2 -C 60 alkynyl group, a C 1 -C 60 alkoxy group, a C 3 -C 10 cycloalkyl group, a C 1 -C 10 heterocycloalkyl group, a C 3 -C 10 cycloalkenyl group, a C 1 -C 10 heterocycloalkenyl group, a C 6 -C 60 aryl group, a C 7 -C 60 alkylaryl group, a C 6 -C 60 aryloxy group, a C 6 -C 60 arylthio group, a C 1 -C 60 heteroaryl group, a C 2 -C 60 alkylheteroaryl group, a C 1 -C 60 heteroaryloxy group, a C 1 -C 60 heteroarylthio group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropoly cyclic group, a C 1 -C 60 alkyl group substituted with deuterium, —F, a cyano group, a C 1 -C 60 alkyl group, a C 6 -C 60 aryl group, or any combination thereof, or a C 6 -C 60 aryl group substituted with deuterium, —F, a cyano group, a C 1 -C 60 alkyl group, a C 6 -C 60 aryl group, or any combination thereof,

and

* indicates a binding site to a neighboring atom,

wherein the condensed cyclic compound satisfies Equation 1,

0 eV<Δ E ST ≤0.5 eV,  Equation 1

in Equation 1, ΔE ST indicates a different between a lowest excitation singlet energy level (E S1 ) of the condensed cyclic compound of Formula 1 and a lowest excitation triplet energy level (E T1 ) of the condensed cyclic compound of Formula 1; and the lowest excitation triplet energy level E T1 and the lowest excitation singlet energy level E S1 are evaluated by a DFT method of Gaussian program structurally optimized at a level of B3LYP, 6-31 G(d,p).

2. The condensed cyclic compound of claim 1 , wherein

X 21 is N, and

X 22 is N(R 24 ), O, or S.

3. The condensed cyclic compound of claim 1 , wherein

two or three of X 31 to X 35 in Formula 3-1 are respectively N, and

two of X 36 to X 38 in Formulae 3-2 to 3-5 are respectively N.

4. The condensed cyclic compound of claim 1 , wherein

X 41 is N(R 43 ).

5. The condensed cyclic compound of claim 1 , wherein

ring A 21 , ring A 22 , ring A 41 , and ring A 42 are each independently a benzene group, a naphthalene group, an anthracene group, a phenanthrene group, a phenalene group, a triphenylene group, a pyridine group, a pyrimidine group, a pyrazine group, a pyridazine group, a triazine group, a quinoline group, an isoquinoline group, a 2,6-naphthyridine group, a 1,8-naphthyridine group, a 1,5-naphthyridine group, a 1,6-naphthyridine group, a 1,7-naphthyridine group, a 2,7-naphthyridine group, a quinoxaline group, a phthalazine group, a quinazoline group, a phenanthroline group, a benzoquinoline group, a benzoisoquinoline group, a benzoquinoxaline group, a benzoquinazoline group, a furan group, a thiophene group, a silole group, an indene group, a fluorene group, an indole group, a carbazole group, a benzofuran group, a dibenzofuran group, a benzothiophene group, a dibenzothiophene group, a benzosilole group, a dibenzosilole group, an indenopyridine group, an indolopyridine group, a benzofuropyridine group, a benzothienopyridine group, a benzosilolopyridine group, an indenopyrimidine group, an indolopyrimidine group, a benzofuropyrimidine group, a benzothienopyrimidine group, or a benzosilolopyrimidine group.

6. The condensed cyclic compound of claim 1 , wherein

ring A 21 and ring A 22 are each independently a benzene group or a naphthalene group, and

ring A 41 and ring A 42 are each independently a benzene group, a naphthalene group, a fluorene group, a carbazole group, a dibenzofuran group, or a dibenzothiophene group.

7. The condensed cyclic compound of claim 1 , wherein

R 11 to R 14 , R 21 to R 25 , R 31 to R 39 , and R 41 to R 44 are each independently:

hydrogen, deuterium, —F, —Cl, —Br, —I, 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, or a C 1 -C 20 alkoxy group;

a C 1 -C 20 alkyl group or a C 1 -C 20 alkoxy group, each substituted with deuterium, —F, —Cl, —Br, —I, —CD 3 , —CD 2 H, —CDH 2 , —CF 3 , —CF 2 H, —CFH 2 , 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 cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cycloctyl group, a an adamantyl group, a norbornyl group, a norbornenyl group, a cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, a phenyl group, a biphenyl group, a C 1 -C 20 alkylphenyl group, a naphthyl group, a pyridinyl group, a pyrimidinyl group, or any combination thereof;

a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cycloctyl group, a an adamantyl group, a norbornyl group, a norbornenyl group, a cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, a phenyl group, a biphenyl group, a C 1 -C 20 alkylphenyl group, a naphthyl group, a fluorenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, a pyrrolyl group, a thiophenyl group, a furanyl group, an imidazolyl group, a pyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolyl group, an isoxazolyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, an isoindolyl group, an indolyl group, an indazolyl group, a purinyl group, a quinolinyl group, an isoquinolinyl group, a benzoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, a cinnolinyl group, a carbazolyl group, a phenanthrolinyl group, a benzimidazolyl group, a benzofuranyl group, a benzothiophenyl group, an isobenzothiazolyl group, a benzoxazolyl group, an isobenzoxazolyl group, a triazolyl group, a tetrazolyl group, an oxadiazolyl group, a triazinyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a dibenzosilolyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, an imidazopyridinyl group, or an imidazopyrimidinyl group;

a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cycloctyl group, an adamantyl group, a norbornyl group, a norbornenyl group, a cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, a phenyl group, a biphenyl group, a C 1 -C 20 alkylphenyl group, a naphthyl group, a fluorenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, a pyrrolyl group, a thiophenyl group, a furanyl group, an imidazolyl group, a pyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolyl group, an isoxazolyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, an isoindolyl group, an indolyl group, an indazolyl group, a purinyl group, a quinolinyl group, an isoquinolinyl group, a benzoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, a cinnolinyl group, a carbazolyl group, a phenanthrolinyl group, a benzimidazolyl group, a benzofuranyl group, a benzothiophenyl group, an isobenzothiazolyl group, a benzoxazolyl group, an isobenzoxazolyl group, a triazolyl group, a tetrazolyl group, an oxadiazolyl group, a triazinyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a dibenzosilolyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, an imidazopyridinyl group, or an imidazopyrimidinyl group, each substituted with deuterium, —F, —Cl, —Br, —I, —CD 3 , —CD 2 H, —CDH 2 , —CF 3 , —CF 2 H, —CFH 2 , a hydroxyl group, a nitro group, a cyano 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 cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cycloctyl group, an adamantyl group, a norbornyl group, a norbornenyl group, a cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, a phenyl group, a biphenyl group, a phenyl(C 1 -C 20 alkyl) group, a naphthyl group, a fluorenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, a pyrrolyl group, a thiophenyl group, a furanyl group, an imidazolyl group, a pyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolyl group, an isoxazolyl group, a pyridinyl group, a pyridinyl group substituted with a phenyl group, a pyrazinyl group, a pyrazinyl group substituted with a phenyl group, a pyrimidinyl group, a pyrimidinyl group substituted with a phenyl group, a pyridazinyl group, a pyridazinyl group substituted with a phenyl group, an isoindolyl group, an indolyl group, an indazolyl group, a purinyl group, a quinolinyl group, an isoquinolinyl group, a benzoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, a cinnolinyl group, a carbazolyl group, a phenanthrolinyl group, a benzimidazolyl group, a benzofuranyl group, a benzothiophenyl group, an isobenzothiazolyl group, a benzoxazolyl group, an isobenzoxazolyl group, a triazolyl group, a tetrazolyl group, an oxadiazolyl group, a triazinyl group, a triazinyl group substituted with a phenyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a dibenzosilolyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, an imidazopyridinyl group, an imidazopyrimidinyl group, —Si(Q 11 )(Q 12 )(Q 13 ), —B(Q 11 )(Q 12 ), —N(Q 11 )(Q 12 ), or any combination thereof; and

—Si(Q 1 )(Q 2 )(Q 3 ), —B(Q 1 )(Q 2 ), or —N(Q 1 )(Q 2 ), and

Q 1 to Q 3 and Q 11 to Q 13 are each independently:

a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group, a sec-butyl group, a tert-butyl group, an n-pentyl group, an isopentyl group, a 2-methylbutyl group, a sec-pentyl group, a tert-pentyl group, a neo-pentyl group, a 3-pentyl group, a 3-methyl-2-butyl group, a phenyl group, a biphenyl group, a phenyl(C 1 -C 20 alkyl) group, or a naphthyl group; or

a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group, a sec-butyl group, a tert-butyl group, an n-pentyl group, an isopentyl group, a 2-methylbutyl group, a sec-pentyl group, a tert-pentyl group, a neo-pentyl group, a 3-pentyl group, a 3-methyl-2-butyl group, a phenyl group, or a naphthyl group, each substituted with deuterium, a phenyl group, or a combination thereof.

8. The condensed cyclic compound of claim 1 , wherein

Y 11 is a group represented by Formulae 2-11 to 2-13:

wherein, in Formulae 2-11 to 2-13,

X 21 and X 22 are the same as defined in connection with those in Formulae 2-1 to 2-3 of claim 1 ,

R 21a to R 21d are each independently the same as defined in connection with R 21 in Formula 2-1 of claim 1 ,

R 22a to R 22d are each independently the same as defined in connection with R 22 in Formula 2-1 of claim 1 , and

* indicates a binding site to a neighboring atom.

9. The condensed cyclic compound of claim 8 , wherein

X 21 is N, and

X 22 is N(R 24 ), O, or S.

10. The condensed cyclic compound of claim 1 , wherein

Y 12 is a group represented by Formulae 3-11 to 3-35 or 4-11 to 4-17:

wherein, in Formulae 3-11 to 3-35 and 4-11 to 4-17,

Y 31 , R 36 to R 39 , and b39 are the same as defined in connection with those of Formulae 3-1 to 3-5 in claim 1 ,

X 41 is O, S, N(R 42g ), or C(R 42g )(R 42h ),

R 41a to R 41d are the same as defined in connection with R 41 in Formula 4-1 in claim 1 ,

R 42a to R 42h are the same as defined in connection with R 42 in Formula 4-1 in claim 1 , and

* indicates a binding site to a neighboring atom.

11. The condensed cyclic compound of claim 1 , wherein

Y 11 is a group represented by Formulae 2-11 to 2-13, and

Y 12 is a group represented by Formulae 3-11 to 3-35 or 4-11 to 4-17:

wherein, in Formulae 2-11 to 2-13, 3-11 to 3-35, and 4-11 to 4-17,

X 21 and X 22 are the same as defined in connection with those in Formulae 2-1 to 2-3 in claim 1 ,

R 21a to R 21d are the same as defined in connection with R 21 in Formula 2-1 in claim 1 ,

R 22a to R 22d are the same as defined in connection with R 22 in Formula 2-1 in claim 1 ,

Y 31 , R 36 to R 39 , and b39 are the same as defined in connection with those in Formulae 3-1 to 3-5 in claim 1 ,

X 41 is O, S, N(R 42g ), or C(R 42g )(R 42h ),

R 41a to R 41d are the same as defined in connection with Ru in Formula 4-1 in claim 1 ,

R 42a to R 42h are the same as defined in connection with R 42 in Formula 4-1 in claim 1 , and

* indicates a binding site to a neighboring atom.

12. The condensed cyclic compound of claim 1 , wherein

the condensed cyclic compound is of Compounds 1 to 117:

13. An organic light-emitting device comprising:

a first electrode;

a second electrode; and

an organic layer between the first electrode and the second electrode and comprising an emission layer and the condensed cyclic compound of claim 1 .

14. The organic light-emitting device of claim 13 , wherein

the first electrode is an anode,

the second electrode is a cathode,

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,

the hole transport region comprises a hole injection layer, a hole transport layer, an electron blocking layer, or any combination thereof, and

the electron transport region comprises a hole blocking layer, an electron transport layer, an electron injection layer, or any combination thereof.

15. The organic light-emitting device of claim 13 , wherein

the emission layer comprises the condensed cyclic compound.

16. The organic light-emitting device of claim 15 , wherein

a proportion of fluorescence components among the total emission components emitted from the emission layer is 90% or more.

17. The organic light-emitting device of claim 15 , wherein

the condensed cyclic compound is a fluorescence emitter, and

a proportion of emission components emitted from the condensed cyclic compound among the total emission components emitted from the emission layer is 80% or more.

18. The organic light-emitting device of claim 17 , wherein

the emission layer consists of the condensed cyclic compound only, or

the emission layer further comprises a host.

19. The organic light-emitting device of claim 15 , wherein

the emission layer comprises a host and a dopant,

the host comprises the condensed cyclic compound,

an amount of the host is greater than that of the dopant, and

a proportion of emission components emitted from the dopant among the total emission components emitted from the emission layer is 80% or more.

20. The organic light-emitting device of claim 15 , wherein

the emission layer comprises a host, an auxiliary dopant, and a dopant,

the auxiliary dopant comprises the condensed cyclic compound, and

a proportion of emission components emitted from the dopant among the total emission components emitted from the emission layer is 80% or more.