Condensed cyclic compound and organic light-emitting device including the same
A condensed cyclic compound represented by Formula 1: wherein in Formula 1, a1, a2, Ar 1 , Ar 2 , R 1 , and R 2 are the same as described in the specification.
1. An organic light-emitting device comprising:
a first electrode as an anode;
a second electrode as a cathode; and
an organic layer disposed between the first electrode and the second electrode,
wherein the organic layer comprises an emission layer,
wherein the organic layer further comprises a hole transport region disposed between the first electrode and the emission layer,
wherein the hole transport region comprises an electron blocking layer, and
wherein the electron blocking layer comprises a condensed cyclic compound represented by Formula 1:
wherein, in Formula 1, Ar 1 is a group represented by Formulae 2A-1 to 2A-5, and Ar 2 is a group represented by Formula 2B,
ring A 1 in Formula 2B is a dibenzofuran ring or a dibenzothiophene ring,
R 1 to R 3 , R 11 , and R 12 in Formulae 1, 2A-1 to 2A-5, and 2B are each independently selected from:
hydrogen, deuterium, a C 1 -C 20 alkyl group, a C 1 -C 20 alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, a carbazolyl group, a pyridinyl group, a dibenzofuranyl group, a dibenzothiophenyl group, and a dibenzosilolyl group;
a C 1 -C 20 alkyl group and a C 1 -C 20 alkoxy group, each substituted with at least one deuterium; and
a phenyl group, a biphenyl group, a terphenyl group, a carbazolyl group, a pyridinyl group, a dibenzofuranyl group, a dibenzothiophenyl group, and a dibenzosilolyl group, each substituted with at least one selected from deuterium, a C 1 -C 20 alkyl group, a C 1 -C 20 alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, a carbazolyl group, a pyridinyl group, a dibenzofuranyl group, a dibenzothiophenyl group, and a dibenzosilolyl group,
a1 in Formula 1 is an integer selected from 0 to 3, wherein, when a1 is two or more, two or more groups R 1 are identical to or different from each other,
a3 in Formulae 2A-1 to 2A-5 is an integer selected from 0 to 2, wherein when a3 is two or more, two or more groups R 3 are identical to or different from each other,
a2 and a12 in Formulae 1 and 2B are each independently an integer selected from 0 to 4, wherein, when a2 is two or more, two or more groups R 2 are identical to or different from each other, and when a12 is two or more, two or more groups R 12 are identical to or different from each other,
a11 in Formula 2B is an integer selected from 0 to 6, wherein, when a11 is two or more, two or more groups R 11 are identical to or different from each other,
R 4 , R 4a , and R 4b are each independently selected from:
a phenyl group, a biphenyl group, and a terphenyl group;
a phenyl group, a biphenyl group, and a terphenyl group, each substituted with at least one selected from deuterium, a C 1 -C 20 alkyl group, and a C 1 -C 20 alkoxy group,
R 5 in Formulae 2A-1 to 2A-5 is selected from:
hydrogen, deuterium, a C 1 -C 20 alkyl group, and a C 1 -C 20 alkoxy group; and
a C 1 -C 20 alkyl group and a C 1 -C 20 alkoxy group, each substituted with at least one deuterium, and
* in Formulae 2A-1 to 2A-5 and 2B indicates a binding site to a neighboring atom.
2. The organic light-emitting device of claim 1 , wherein Ar 2 is one selected from groups represented by Formulae 2B-1 to 2B-6:
wherein, in Formulae 2B-1 to 2B-6,
X 1 is O or S,
R 12 and a12 are each independently the same as in claim 1 ,
R 13 to R 18 are each independently the same as R 11 in claim 1 , and
* indicates a binding site to a neighboring atom.
3. The organic light-emitting device of claim 1 , wherein R 1 to R 3 , R 11 , and R 12 are each independently selected from:
hydrogen, deuterium, a C 1 -C 10 alkyl group, a C 1 -C 10 alkoxy group, a phenyl group, a biphenyl group, and a terphenyl group;
a C 1 -C 10 alkyl group and a C 1 -C 20 alkoxy group, each substituted with at least one deuterium; and
a phenyl group, a biphenyl group, and a terphenyl group, each substituted with at least one selected from deuterium, a C 1 -C 20 alkyl group, a C 1 -C 20 alkoxy group, a phenyl group, a biphenyl group, and a terphenyl group.
4. The organic light-emitting device of claim 1 , wherein R 4 is one selected from groups represented by Formulae 3-1 to 3-7:
wherein, in Formulae 3-1 to 3-7,
R 21 to R 23 are each independently hydrogen, deuterium, a C 1 -C 10 alkyl group, or a C 1 -C 10 alkoxy group,
a21 is an integer selected from 0 to 5,
a22 and a23 are each independently an integer selected from 0 to 4, and
* indicates a binding site to a neighboring atom.
5. The organic light-emitting device of claim 1 , wherein R 5 is hydrogen, deuterium, a C 1 -C 10 alkyl group, or a C 1 -C 10 alkoxy group.
6. The organic light-emitting device of claim 1 , wherein the condensed cyclic compound is represented by one selected from Formulae 1-1 to 1-4:
wherein, in Formulae 1-1 to 1-4, Ar 1 , A 2 , R 1 , R 2 , a1, and a2 are each independently the same as in claim 1 .
7. The organic light-emitting device of claim 6 ,
wherein, in Formulae 2A-1 to 2A-5,
R 4 , R 4a , and R 4b are each independently selected from groups represented by Formulae 3-1 to 3-7
wherein, in Formulae 3-1 to 3-7,
R 21 to R 23 are each independently hydrogen, deuterium, a C 1 -C 10 alkyl group, or a C 1 -C 10 alkoxy group,
a21 is an integer selected from 0 to 5,
a22 and a23 are each independently an integer selected from 0 to 4, and
* indicates a binding site to a neighboring atom.
8. The organic light-emitting device of claim 7 , wherein Ar 2 is one selected from groups represented by Formulae 2B-1 to 2B-6:
wherein, in Formulae 2B-1 to 2B-6,
X 1 is O or S,
R 12 and a12 are each independently the same as in claim 1 ,
R 13 to R 18 are each independently the same as R 11 in claim 1 , and
* indicates a binding site to a neighboring atom.
9. The organic light-emitting device of claim 8 , wherein R 12 to R 18 are each independently selected from:
hydrogen, deuterium, a C 1 -C 10 alkyl group, a C 1 -C 10 alkoxy group, a phenyl group, a biphenyl group, and a terphenyl group;
a C 1 -C 10 alkyl group and a C 1 -C 10 alkoxy group, each substituted with at least one deuterium; and
a phenyl group, a biphenyl group, and a terphenyl group, each substituted with at least one selected from deuterium, a C 1 -C 20 alkyl group, a C 1 -C 20 alkoxy group, a phenyl group, a biphenyl group, and a terphenyl group.
10. The organic light-emitting device of claim 1 , wherein the condensed cyclic compound has an absolute value of a highest occupied molecular orbital in a range of about 5.0 electron volts to about 5.3 electron volts.
11. The organic light-emitting device of claim 1 , wherein the condensed cyclic compound has a triplet energy level of about 2.8 electron volts or more.
12. The organic light-emitting device of claim 1 , wherein the condensed cyclic compound is one selected from Compounds 1 to 11:
13. The organic light-emitting device of claim 1 , wherein the organic layer further comprises an electron transport region disposed between the emission layer and the second electrode, wherein the electron transport region comprises a hole blocking layer, an electron transport layer, an electron injection layer, or a combination thereof.
14. The organic light-emitting device of claim 1 , wherein the emission layer comprises the condensed cyclic compound represented by Formula 1.
15. The organic light-emitting device of claim 1 , wherein the emission layer further comprises a phosphorescent dopant, wherein the phosphorescent dopant comprises an organometallic compound represented by Formula 81:
M(L 81 ) n81 (L 82 ) n82 Formula 81
wherein, in Formulae 81 and 81A,
M is selected from iridium (Ir), platinum (Pt), osmium (Os), titanium (Ti), zirconium (Zr), hafnium (Hf), europium (Eu), terbium (Tb), thulium (Tm), and rhodium (Rh),
L 81 is a ligand represented by Formula 81A, wherein n81 is an integer selected from 1 to 3, and when n81 is two or more, two or more groups L 81 are identical to or different from each other,
L 82 is an organic ligand, wherein n82 is an integer selected from 0 to 4, and when n82 is two or more, two or more groups L 82 are identical to or different from each other,
Y 81 to Y 84 are each independently C or N,
Y 81 and Y 82 are linked to each other via a single bond or a double bond, and Y 83 and Y 84 are linked to each other via a single bond or a double bond,
CY 81 and CY 82 are each independently selected from a C 5 -C 30 carbocyclic group and a C 1 -C 30 heterocarbocyclic group,
CY 81 and CY 82 are optionally further linked to each other via an organic linking group,
R 81 to R 85 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, —SF 5 , 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, a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, —Si(Q 81 )(Q 82 )(Q 83 ), —N(Q 84 )(Q 85 ), —B(Q 86 )(Q 87 ), and —P(═O)(Q 88 )(Q 89 ),
a81 to a83 are each independently an integer selected from 0 to 5, wherein, when a81 is two or more, two or more groups R 81 are identical to or different from each other, when a82 is two or more, two or more groups R 82 are identical to or different from each other, when a81 is two or more, two or more neighboring groups R 81 are optionally linked to each other to form a saturated or unsaturated ring, and when a82 is two or more, two or more groups R 82 are optionally linked to each other to form a saturated or unsaturated ring,
* and *′ in Formula 81A each indicate a binding site to M of Formula 81,
at least one substituent selected from the substituted C 1 -C 60 alkyl group, the substituted C 2 -C 60 alkenyl group, the substituted C 2 -C 60 alkynyl group, the substituted C 1 -C 60 alkoxy group, the substituted C 3 -C 10 cycloalkyl group, the substituted C 1 -C 10 heterocycloalkyl group, the substituted C 3 -C 10 cycloalkenyl group, the substituted C 1 -C 10 heterocycloalkenyl group, the substituted C 6 -C 60 aryl group, the substituted C 6 -C 60 aryloxy group, the substituted C 6 -C 60 arylthio group, the substituted C 1 -C 60 heteroaryl group, the substituted monovalent non-aromatic condensed polycyclic group, and the substituted monovalent non-aromatic condensed heteropolycyclic group is 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 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 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, and —Si(Q 91 )(Q 92 )(Q 93 ), and
Q 81 to Q 89 and Q 91 to Q 93 are each independently selected from hydrogen, deuterium, a C 1 -C 60 alkyl 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 1 -C 60 heteroaryl group, a monovalent non-aromatic condensed polycyclic group, and a monovalent non-aromatic condensed heteropolycyclic group.
16. The organic light-emitting device of claim 15 , wherein, in Formula 81A, at least one selected from R 81 in the number of a81 and R 82 in the number of a82 is a cyano group or deuterium.
17. The organic light-emitting device of claim 14 , wherein the emission layer emits blue light.
18. The organic light-emitting device of claim 1 , wherein the hole transport region further comprises a hole injection layer, a hole transport layer, or a combination thereof.
19. A condensed cyclic compound represented by Formula 1:
wherein, in Formula 1, Ar 1 is one selected from groups represented by Formulae 2A-1, 2A-3, 2A-4 and 2A-5, and Ar 2 is a group represented by Formula 2B,
ring A 1 in Formula 2B is a dibenzofuran ring or a dibenzothiophene ring,
R 1 to R 3 , R 11 , and R 12 in Formulae 1, 2A-1, 2A-3, 2A-4, 2A-5 and 2B are each independently selected from:
hydrogen, deuterium, a C 1 -C 20 alkyl group, a phenyl group, a biphenyl group and a terphenyl group;
a C 1 -C 20 alkyl group substituted with at least one deuterium; and
a phenyl group, a biphenyl group and a terphenyl group, each substituted with at least one selected from deuterium, a C 1 -C 20 alkyl group, a phenyl group, a biphenyl group and a terphenyl group,
a1 and a3 in Formulae 1, 2A-1, 2A-3, 2A-4 and 2A-5 are each independently an integer selected from 0 to 2, wherein, when a1 is two or more, two or more groups R 1 are identical to or different from each other, and when a3 is two or more, two or more groups R 3 are identical to or different from each other,
a2 and a12 in Formulae 1 and 2B are each independently an integer selected from 0 to 4, wherein, when a2 is two or more, two or more groups R 2 are identical to or different from each other, and when a12 is two or more, two or more groups R 12 are identical to or different from each other,
a11 in Formula 2B is an integer selected from 0 to 6, wherein, when a11 is two or more, two or more groups R 11 are identical to or different from each other,
R 4 , R 4a and R 4b in Formula 2A-1, 2A-3, 2A-4 and 2A-5 are each independently selected from:
a phenyl group, a biphenyl group, and a terphenyl group;
a phenyl group, a biphenyl group, and a terphenyl group, each substituted with at least one selected from deuterium and a C 1 -C 20 alkyl group,
R 5 in Formulae 2A-1, 2A-3, 2A-4 and 2A-5 is selected from:
hydrogen, deuterium and a C 1 -C 20 alkyl group; and
a C 1 -C 20 alkyl group substituted with at least one deuterium, and
* in Formulae 2A-1, 2A-3, 2A-4, 2A-5 and 2B indicates a binding site to a neighboring atom.
20. A condensed cyclic compound represented by Formula 1.
wherein, in Formula 1, Ar 1 is a group represented by Formula 2A, and Ar 2 is one selected from groups represented by Formula 2B-1, 2B-3, 2B-4 and 2B-5,
X 1 in Formula 2B-1, 2B-3, 2B-4 and 2B-5 is O or S,
R 1 to R 3 and R 12 to R 18 in Formulae 1, 2A, 2B-1, 2B-3, 2B-4 and 2B-5 are each independently selected from:
hydrogen, deuterium, a C 1 -C 20 alkyl group, a phenyl group, a biphenyl group and a terphenyl group;
a C 1 -C 20 alkyl group substituted with at least one deuterium; and
a phenyl group, a biphenyl group and a terphenyl group, each substituted with at least one selected from deuterium, a C 1 -C 20 alkyl group, a phenyl group, a biphenyl group and a terphenyl group,
a1 and a3 in Formulae 1 and 2A are each independently an integer selected from 0 to 3, wherein, when a1 is two or more, two or more groups R 1 are identical to or different from each other, and when a3 is two or more, two or more groups R 3 are identical to or different from each other,
a2 and a12 in Formulae 1, 2B-1, 2B-3, 2B-4 and 2B-5 are each independently an integer selected from 0 to 4, wherein, when a2 is two or more, two or more groups R 2 are identical to or different from each other, and when a12 is two or more, two or more groups R 12 are identical to or different from each other,
R 4 in Formula 2A is selected from:
a phenyl group, a biphenyl group, and a terphenyl group;
a phenyl group, a biphenyl group, and a terphenyl group, each substituted with at least one selected from deuterium and a C 1 -C 20 alkyl group,
a4 in Formula 2A is an integer selected from 1 to 4, wherein, when a4 is two or more, two or more groups R 4 are identical to or different from each other,
R 5 in Formula 2A is selected from:
hydrogen, deuterium and a C 1 -C 20 alkyl group; and
a C 1 -C 20 alkyl group substituted with at least one deuterium, and
* in Formulae 2A, 2B-1, 2B-3, 2B-4 and 2B-5 indicates a binding site to a neighboring atom.
21. A condensed cyclic compound being selected from Compounds 1, 2, 4, 5, and 7: