Condensed cyclic compound and organic light-emitting device including the same
A condensed cyclic compound represented by Formula 1: Ar 1 -(L 1 ) a1 -Ar 2 Formula 1 wherein, in Formula 1, Ar 1 , Ar 2 , L 1 , and a1 are the same as described in the specification.
1. A condensed cyclic compound represented by Formula 1:
wherein, in Formulae 1, 2-2, 2-4, 3-12, 3-15, and 3-16,
Ar 1 is selected from groups represented by Formulae 2-2 and 2-4;
Ar 2 is selected from groups represented by Formulae 3-12, 3-15, and 3-16;
L 1 is selected from a substituted or unsubstituted C 6 -C 60 arylene group and a substituted or unsubstituted C 1 -C 60 heteroarylene group;
a1 is selected from 1, 2, and 3;
X 21 is selected from O, S, C(R 22 )(R 23 ), Si(R 22 )(R 23 ), Ge(R 22 )(R 23 ), and P(═O)(R 22 );
X 31 is selected from O, S, N(R 34 ), C(R 34 )(R 35 ), Si(R 34 )(R 35 ), and Ge(R 34 )(R 35 );
provided that when Ar 1 is Formula 2-4 and Ar 2 is Formula 3-12, when X 21 is S, then X 31 is selected from O, S, C(R 34 )(R 35 ), Si(R 34 )(R 35 ), and Ge(R 34 )(R 35 );
A 21 is selected from a C 5 -C 20 carbocyclic group and a C 4 -C 20 heterocyclic group;
Y 21 is selected from a substituted or unsubstituted C 6 -C 60 aryl group and a substituted or unsubstituted C 1 -C 60 heteroaryl group;
R 21 to R 23 , R 31a to R 31d , R 32a to R 32d , R 33a to R 33d , R 34 , and R 35 are each independently selected from
hydrogen, 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 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 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 monovalent non-aromatic condensed polycyclic group, and a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group;
b21 is selected from 1, 2, 3, 4, 5, 6, 7, and 8; and
* denotes a binding site to a neighboring atom.
2. The condensed cyclic compound of claim 1 , wherein L 1 is selected from
a phenylene group, a naphthylene group, a pyridinylene group, a pyrimidinylene group, a pyrazinylene group, a pyridazinylene group, and a triazinylene group; and
a phenylene group, a naphthylene group, a pyridinylene group, a pyrimidinylene group, a pyrazinylene group, a pyridazinylene group, and a triazinylene group, each substituted with at least one selected from 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 C 1 -C 10 alkyl group, a C 1 -C 10 alkoxy group, a phenyl group, and a naphthyl group.
3. The condensed cyclic compound of claim 1 , wherein L 1 is selected from a single bond and groups represented by Formulae 4-1 to 4-15:
wherein, in Formulae 4-1 to 4-15,
R 41 is selected from hydrogen, 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 C 1 -C 10 alkyl group, a C 1 -C 10 alkoxy group, a phenyl group, and a naphthyl group;
b41 is selected from 1, 2, 3, and 4;
b42 is selected from 1, 2, 3, 4, 5, and 6; and
* and *′ each independently denote a binding site to a neighboring atom.
4. The condensed cyclic compound of claim 1 , wherein a1 is 1.
5. The condensed cyclic compound of claim 1 , wherein (L 1 ) a1 is selected from groups represented by Formulae 5-1 to 5-3:
wherein, in Formulae 5-1 to 5-3,
* and *′ each independently denote a binding site to a neighboring atom.
6. The condensed cyclic compound of claim 1 , wherein A 21 is selected from a benzene group, a naphthalene group, an anthracene group, a phenanthrene group, a triphenylene group, a pyridine group, a pyrimidine group, a pyrazine group, a quinoline group, an isoquinoline group, 2,6-naphthyridine group, 1,8-naphthyridine group, 1,5-naphthyridine group, 1,6-naphthyridine group, 1,7-naphthyridine group, 2,7-naphthyridine group, a quinoxaline group, a phthalazine group, a quinazoline group, and a cinnoline group.
7. The condensed cyclic compound of claim 1 , wherein A 21 is selected from a benzene group and a naphthalene group.
8. The condensed cyclic compound of claim 1 , wherein Y 21 is selected from
a phenyl group, a biphenyl group, a terphenyl group, a pentalenyl group, a naphthyl group, an azulenyl group, a heptalenyl group, an indacenyl group, an acenaphthyl group, a phenalenyl group, a phenanthrenyl group, an anthracenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, a naphthacenyl group, a picenyl group, a perylenyl group, a pentaphenyl group, a hexacenyl group, a pyrrolyl group, an imidazolyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, an indolyl group, a quinolinyl group, an isoquinolinyl group, a benzoquinolinyl group, a phthalazinyl group, a naphthyridinyl group, a quinoxalinyl group, a quinazolinyl group, a cinnolinyl group, a phenanthridinyl group, an acridinyl group, a phenanthrolinyl group, a phenazinyl group, a furanyl group, a benzofuranyl group, a thiophenyl group, a benzothiophenyl group, and a triazinyl group; and
a phenyl group, a biphenyl group, a terphenyl group, a pentalenyl group, a naphthyl group, an azulenyl group, a heptalenyl group, an indacenyl group, an acenaphthyl group, a phenalenyl group, a phenanthrenyl group, an anthracenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, a naphthacenyl group, a picenyl group, a perylenyl group, a pentaphenyl group, a hexacenyl group, a pyrrolyl group, an imidazolyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, an indolyl group, a quinolinyl group, an isoquinolinyl group, a benzoquinolinyl group, a phthalazinyl group, a naphthyridinyl group, a quinoxalinyl group, a quinazolinyl group, a cinnolinyl group, a phenanthridinyl group, an acridinyl group, a phenanthrolinyl group, a phenazinyl group, a furanyl group, a benzofuranyl group, a thiophenyl group, a benzothiophenyl group, and a triazinyl group, each substituted with at least one selected from deuterium, 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 20 alkyl group, a C 1 -C 20 alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, and a naphthyl group.
9. The condensed cyclic compound of claim 1 , wherein Y 21 is selected from
a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a phenanthrenyl group, an anthracenyl group, a triphenylenyl group, a pyrenyl group, and a chrysenylgroup; and
a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a phenanthrenyl group, an anthracenyl group, a triphenylenyl group, a pyrenyl group, and a chrysenyl group, each substituted with at least one selected from deuterium, 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 20 alkyl group, a C 1 -C 20 alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, and a naphthyl group.
10. The condensed cyclic compound of claim 1 , wherein Y 21 is selected from groups represented by Formulae 6-1 to 6-4:
wherein, in Formulae 6-1 to 6-4,
R 61 is selected from hydrogen, deuterium, 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 20 alkyl group, and a C 1 -C 20 alkoxy group;
b61 is selected from 1, 2, 3, 4, and 5;
b62 is selected from 1, 2, 3, and 4;
b63 is selected from 1, 2, 3, 4, 5, 6, and 7; and
* denotes a binding site to a neighboring atom.
11. The condensed cyclic compound of claim 1 , wherein R 21 to R 23 , R 31a to R 31d , R 32a to R 32d , R 33a to R 33d , R 34 , and R 35 are each independently selected from
hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl 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 deuterium, a hydroxyl 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 phenyl group, and a naphthyl group;
a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclopentenyl group, a cyclohexenyl group, a phenyl group, a biphenyl group, a terphenyl group, a pentalenyl group, an indenyl group, a naphthyl group, an azulenyl group, a heptalenyl group, an indacenyl group, an acenaphthyl group, a fluorenyl group, a spiro-bifluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenalenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, a naphthacenyl group, a picenyl group, a perylenyl group, a pentaphenyl group, a hexacenyl group, a pentacenyl group, a rubicenyl group, a coronenyl group, an ovalenyl group, a thiophenyl group, a furanyl group, a carbazolyl group, a benzofuranyl group, a benzothiophenyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, and a dibenzocarbazolyl group; and
a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclopentenyl group, a cyclohexenyl group, a phenyl group, a biphenyl group, a terphenyl group, a pentalenyl group, an indenyl group, a naphthyl group, an azulenyl group, a heptalenyl group, an indacenyl group, an acenaphthyl group, a fluorenyl group, a spiro-bifluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenalenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, a naphthacenyl group, a picenyl group, a perylenyl group, a pentaphenyl group, a hexacenyl group, a pentacenyl group, a rubicenyl group, a coronenyl group, an ovalenyl group, a thiophenyl group, a furanyl group, a carbazolyl group, a benzofuranyl group, a benzothiophenyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, and a dibenzocarbazolyl group, each substituted with at least one selected from 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 C 1 -C 20 alkyl group, a C 1 -C 20 alkoxy group, a phenyl group, and a naphthyl group.
12. The condensed cyclic compound of claim 1 , wherein Ar 1 is selected from groups represented by Formulae 2-11 to 2-14:
wherein, in Formulae 2-12 and 2-14,
Y 21 and X 21 are the same as described in connection with Formulae 2-2 and 2-4;
R 24 to R 27 are the same as described in connection with R 21 in Formulae 2-2 and 2-4;
provided that when Ar 1 is Formula 2-14 and Ar 2 is Formula 3-12, when X 21 is S, then X 31 is selected from O, S, C(R 34 )(R 35 ), Si(R 34 )(R 35 ), and Ge(R 34 )(R 35 ); and
* denotes a binding site to a neighboring atom.
13. The condensed cyclic compound of claim 1 , wherein the condensed cyclic compound represented by Formula 1 is selected from compounds represented by Formulae 1-8, 1-11, 1-12, 1-20, 1-23, and 1-24:
wherein, in Formulae 1-8, 1-11, 1-12, 1-20, 1-23, and 1-24,
L 1 is selected from
a phenylene group, a naphthylene group, a pyridinylene group, a pyrimidinylene group, a pyrazinylene group, a pyridazinylene group, and a triazinylene group; and
a phenylene group, a naphthylene group, a pyridinylene group, a pyrimidinylene group, a pyrazinylene group, a pyridazinylene group, and a triazinylene group, each substituted with at least one selected from 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 C 1 -C 10 alkyl group, a C 1 -C 10 alkoxy group, a phenyl group, and a naphthyl group;
a1 is 1;
Y 21 and X 21 are the same as described in connection with Formulae 2-2 and 2-4;
R 24 to R 27 are the same as described in connection with R 21 in Formulae 2-2 and 2-4;
X 31 is the same as described in connection with Formulae 3-12, 3-15, and 3-16;
provided that in Formula 1-20, when X 21 is S, then X 31 is selected from O, S, C(R 34 )(R 35 ), Si(R 34 )(R 35 ), and Ge(R 34 )(R 35 );
R 31a , R 31b , R 31c , and R 31d are each independently the same as described in connection with R 31 in Formulae 3-12, 3-15 and 3-16;
R 32a and R 32b are each independently the same as described in connection with R 32 in Formulae 3-12, 3-15, and 3-16; and
R 33a , R 33b , R 33c , and R 33d are each independently the same as described in connection with R 33 in Formulae 3-12, 3-15, and 3-16.
14. The condensed cyclic compound of claim 1 , wherein (L 1 ) a1 is selected from groups represented by Formulae 5-1 to 5-3:
wherein, in Formulae 5-1 to 5-3,
* and *′ each independently denote a binding site to a neighboring atom.
15. 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 claim 1 .
16. The organic light-emitting device of claim 15 , wherein the emission layer comprises the condensed cyclic compound.
17. 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 represented by Formula 1,
wherein the emission layer emits blue light:
wherein, in Formulae 1, 2-1 to 2-4, 3-1, and 3-2,
Ar 1 is selected from groups represented by Formulae 2-1 to 2-4;
Ar 2 is selected from groups represented by Formulae 3-1 and 3-2;
L 1 is selected from a substituted or unsubstituted C 6 -C 60 arylene group and a substituted or unsubstituted C 1 -C 60 heteroarylene group;
a1 is selected from 1, 2, and 3;
X 21 is selected from O, S, C(R 22 )(R 23 ), Si(R 22 )(R 23 ), Ge(R 22 )(R 23 ), and P(═O)(R 22 );
X 31 is selected from O, S, N(R 34 ), C(R 34 )(R 35 ), Si(R 34 )(R 35 ), and Ge(R 34 )(R 35 );
A 21 , A 31 , and A 33 are each independently selected from a C 5 -C 20 carbocyclic group and a C 4 -C 20 heterocyclic group;
A 32 is selected from a C 5 -C 20 carbocyclic group;
Y 21 is selected from a substituted or unsubstituted C 6 -C 60 aryl group and a substituted or unsubstituted C 1 -C 60 heteroaryl group;
R 21 to R 23 and R 31 to R 35 are each independently selected from hydrogen, 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 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 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 monovalent non-aromatic condensed polycyclic group, and a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group;
b21 is selected from 1, 2, 3, 4, 5, 6, 7, and 8;
b31 to b33 are each independently selected from 1, 2, 3, 4, 5, and 6; and
* denotes a binding site to a neighboring atom,
wherein the emission layer comprises the condensed cyclic compound, wherein the emission layer further comprises a host, and wherein the condensed cyclic compound is a dopant.
18. The condensed cyclic compound of claim 17 , wherein A 32 is selected from a benzene group, a naphthalene group, an anthracene group, a phenanthrene group, and a triphenylene group.
19. The condensed cyclic compound of claim 17 , wherein A 32 is selected from a benzene group and a naphthalene group.