Condensed cyclic compound and organic light-emitting device including the same
A condensed cyclic compound represented by Formula 1: Ar 1 -L 1 -L 2 -Ar 2 Formula 1 wherein in Formula 1, Ar 1 , Ar 2 , L 1 , and L 2 are the same as described in the specification.
1. A condensed cyclic compound represented by Formula 1:
wherein, in Formula 1,
Ar 1 is a group represented by Formula 2,
Ar 2 is a group represented by Formula 3,
L 1 is selected from a group represented by Formula 4A, a group represented by Formula 4B, and a group represented by Formula 4C, L 2 is selected from a group represented by Formula 4D, a group represented by Formula 4E, and a group represented by Formula 4F, wherein a case in which L 1 is the group represented by Formula 4C and L 2 is the group represented by Formula 4F is excluded,
R 1 to R 4 , R 11 to R 14 , R 21 to R 24 , R 31 to R 34 , and R 41 to R 49 are each independently selected from hydrogen, deuterium, —F, —Cl, —Br, —I, 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 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, a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group (provided that the substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group is not a substituted or unsubstituted carbazolyl group), —N(Q 4 )(Q 5 ), and —B(Q 6 )(Q 7 ),
the number of cyano group(s) (CN) in a group represented by *-L 1 -L 2 -*′ in Formula 1 is 1, 2, 3, or 4,
a1 to a9 are each independently an integer selected from 0 to 5,
* and *′ each indicate a binding site to a neighboring atom,
at least one of substituents of the substituted carbazolyl group, substituted C 6 -C 60 aryl group, substituted C 6 -C 60 aryloxy group, substituted C 6 -C 60 arylthio group, substituted C 1 -C 60 heteroaryl group, substituted monovalent non-aromatic condensed polycyclic group, and substituted monovalent non-aromatic condensed heteropolycyclic group is selected from
deuterium, —CD 3 , —CD 2 H, —CDH 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, and a phosphoric acid group or a salt thereof;
a C 6 -C 60 aryl group, a C 6 -C 60 aryloxy group, a C 6 -C 60 arylthio group, a C 1 -C 60 heteroaryl group, a monovalent non-aromatic condensed polycyclic group, and a monovalent non-aromatic condensed heteropolycyclic group (provided that the non-aromatic condensed heteropolycyclic group is not a carbazolyl group);
a C 6 -C 60 aryl group, a C 6 -C 60 aryloxy group, a C 6 -C 60 arylthio group, a C 1 -C 60 heteroaryl group, a monovalent non-aromatic condensed polycyclic group, and a monovalent non-aromatic condensed heteropolycyclic group (provided that the non-aromatic condensed heteropolycyclic group is not a carbazolyl group), each substituted with at least one selected from deuterium,—CD 3 , —CD 2 H, —CDH 2 , a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazine 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, C 6 -C 60 aryl group, a C 6 -C 60 aryloxy group, a C 6 -C 60 arylthio group, a C 1 -C 60 heteroaryl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group (provided that the non-aromatic condensed heteropolycyclic group is not a carbazolyl group), —N(Q 24 )(Q 25 ), and —B(Q 26 )(Q 27 ); and
—N(Q 34 )(Q 35 ) and —B(Q 36 )(Q 37 ),
wherein Q 4 to Q 7 , Q 24 to Q 27 and Q 34 to Q 37 are each independently 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 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 (provided that the substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group is not a substituted or unsubstituted carbazolyl group).
2. The condensed cyclic compound of claim 1 , wherein
R 1 to R 4 , R 11 to R 14 , R 21 to R 24 , R 31 to R 34 , and R 41 to R 49 are each independently selected from:
hydrogen, deuterium, —F, —Cl, —Br, —I, 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 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 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 pyrrolyl group, an imidazolyl group, a pyrazolyl 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 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 benzooxazolyl group, a benzimidazolyl group, a furanyl group, a benzofuranyl group, a thiophenyl group, a benzothiophenyl group, a thiazolyl group, an isothiazolyl group, a benzothiazolyl group, an isoxazolyl group, an oxazolyl group, a triazolyl group, a tetrazolyl group, an oxadiazolyl group, a triazinyl group, a dibenzofuranyl group, a dibenzothiophenyl group, imidazopyrimidinyl group, an imidazopyridinyl group, a pyridoindolyl group, a benzofuropyridinyl group, a benzothienopyridinyl group, a pyrimidoindolyl group, a benzofuropyrimidinyl group, a benzothienopyrimidinyl group, a phenoxazinyl group, a pyridobenzooxazinyl group, and a pyridobenzothiazinyl 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-fluorenyl 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 pyrrolyl group, an imidazolyl group, a pyrazolyl 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 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 benzooxazolyl group, a benzimidazolyl group, a furanyl group, a benzofuranyl group, a thiophenyl group, a benzothiophenyl group, a thiazolyl group, an isothiazolyl group, a benzothiazolyl group, an isoxazolyl group, an oxazolyl group, a triazolyl group, a tetrazolyl group, an oxadiazolyl group, a triazinyl group, a dibenzofuranyl group, a dibenzothiophenyl group, imidazopyrimidinyl group, an imidazopyridinyl group, a pyridoindolyl group, a benzofuropyridinyl group, a benzothienopyridinyl group, a pyrimidoindolyl group, a benzofuropyrimidinyl group, a benzothienopyrimidinyl group, a phenoxazinyl group, a pyridobenzooxazinyl group, and a pyridobenzothiazinyl 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 phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, an anthracenyl group, a pyrenyl group, a phenanthrenyl group, a fluorenyl group, a pyridinyl group, a pyrimidinyl group, a pyrazinyl group, a pyridazinyl group, a triazinyl group, a quinolinyl group, an isoquinolinyl group, a phthalazinyl group, a quinoxalinyl group, a cinnolinyl group, a quinazolinyl group, —N(Q 34 )(Q 35 ), and —B(Q 36 )(Q 37 ); and
—N(Q 4 )(Q 5 ) and —B(Q 6 )(Q 7 ),
wherein Q 4 to Q 7 and Q 34 to Q 37 are each independently selected from hydrogen, C 1 -C 20 alkyl group, a C 1 -C 20 alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a fluorenyl group, a dibenzofuranyl group, and a dibenzothiophenyl group.
3. The condensed cyclic compound of claim 1 , wherein
R 1 to R 4 , R 11 to R 14 , R 21 to R 24 , R 31 to R 34 , and R 41 to R 49 are each independently selected from:
hydrogen, deuterium, and a cyano group (CN);
a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a fluorenyl group, a dibenzofuranyl group and a dibenzothiophenyl group; and
a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a fluorenyl group, a dibenzofuranyl group, and a dibenzothiophenyl group, each substituted with at least one selected from deuterium, a cyano group, a phenyl group, a biphenyl group, a terphenyl group, and a naphthyl group.
4. The condensed cyclic compound of claim 1 , wherein
at least one selected from R 3 , R 13 , R 23 , and R 33 in Formulae 2 and 3 is a cyano group.
5. The condensed cyclic compound of claim 1 , wherein
a1 to a9 in Formulae 4A to 4F are each independently 0, 1, or 2.
6. The condensed cyclic compound of claim 1 , wherein
one, two, three, or four substituents of *-L 1 -L 2 -*′ in Formula 1 are each independently selected from:
hydrogen, deuterium, and a cyano group;
a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a fluorenyl group, a dibenzofuranyl group, and a dibenzothiophenyl group;
a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a fluorenyl group, a dibenzofuranyl group, and a dibenzothiophenyl group, each substituted with at least one selected from deuterium, a cyano group, a phenyl group, a biphenyl group, a terphenyl group, and a naphthyl group.
7. The condensed cyclic compound of claim 1 , wherein
one, two, three, or four substituents of *-L 1 -L 2 -*′ in Formula 1 are each independently selected from:
a cyano group; and
a phenyl group, a biphenyl group, and a terphenyl group, each substituted with at least one cyano group.
8. The condensed cyclic compound of claim 1 , wherein
the number of cyano group(s) in the condensed cyclic compound represented by Formula 1 is 1, 2, 3, or 4.
9. The condensed cyclic compound of claim 1 , wherein
the number of carbazole ring systems in the condensed cyclic compound represented by Formula 1 is 2.
10. The condensed cyclic compound of claim 1 , wherein
the condensed cyclic compound is represented by one of Formulae 1-1 to 1-28:
wherein, in Formulae 1-1 to 1-28,
Ar 1 and Ar 2 are the same as described in claim 1 ,
R 51 to R 58 and R 61 to R 64 are each independently the same as described in connection with R 41 in claim 1 , and
the number of cyano group(s) in R 51 to R 58 and R 61 to R 64 is 1, 2, 3, or 4.
11. The condensed cyclic compound of claim 10 , wherein
R 51 to R 58 and R 61 to R 64 are each independently selected from:
hydrogen, deuterium, and a cyano group;
a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a fluorenyl group, a dibenzofuranyl group, and a dibenzothiophenyl group; and
a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a fluorenyl group, a dibenzofuranyl group, and a dibenzothiophenyl group, each substituted with at least one selected from deuterium, a cyano group, a phenyl group, a biphenyl group, a terphenyl group, and a naphthyl group.
12. The condensed cyclic compound of claim 10 , wherein
one, two, three, or four selected from R 51 to R 58 and R 61 to R 64 are each independently selected from:
a cyano group; and
a phenyl group, a biphenyl group, and a terphenyl group, each substituted with at least one cyano group.
13. The condensed cyclic compound of claim 10 , wherein
one, two, three, or four selected from R 51 to R 58 and R 61 to R 64 are a cyano group.
14. A condensed cyclic compound selected from Compounds 1 to 260:
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
wherein the organic layer comprises at least one of the condensed cyclic compounds represented by Formula 1 of claim 1 .
16. The organic light-emitting device of claim 15 , wherein
the first electrode is an anode,
the second electrode is a cathode, and
the organic layer comprises a hole transport region disposed between the first electrode and the emission layer and an electron transport region disposed between the emission layer and the second electrode,
wherein the hole transport region comprises at least one selected from a hole injection layer, a hole transport layer, and an electron blocking layer, and
wherein the electron transport region comprises at least one selected from a hole blocking layer, an electron transport layer, and an electron injection layer.
17. The organic light-emitting device of claim 15 , wherein
the emission layer comprises the condensed cyclic compound represented by Formula 1.
18. 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 represented by Formula 1, and
an amount of the host is greater than an amount of the dopant.
19. The organic light-emitting device of claim 18 , wherein
the emission layer is a layer that emits blue light.
20. The organic light-emitting device of claim 16 , wherein
the electron transport region comprises the hole blocking layer, and the hole blocking layer comprises the condensed cyclic compound represented by Formula 1.