Heterocyclic compound, organic light-emitting device including the heterocyclic compound, and electronic apparatus including the organic light-emitting device
Provided are a heterocyclic compound represented by Formula 1-1 or 1-2, an organic light-emitting device including the heterocyclic compound, and an electronic apparatus including the organic light-emitting device: wherein Formulae 1-1 and 1-2 are respectively the same as described in the present specification.
1 . A heterocyclic compound represented by Formula 1-1:
wherein, in Formulae 1-1,
A 11 to A 16 are each independently a substituted or unsubstituted C 5 -C 30 carbocyclic group or a substituted or unsubstituted C 1 -C 30 heterocyclic group,
X 11 to X 16 are each independently a group represented by Formula 2-1 or 2-2,
n11 to n16 are each independently 0, 1, or 2,
the sum of n11 to n16 in Formula 1-1 is 2 or more,
Y 11 to Y 16 are each independently 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 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, or a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group,
m11 to m16 are each independently 0, 1, or 2,
the sum of n11 to n16 and m11 to m16 in Formula 1-1 is 3 or more, the
Z 11 to Z 16 are each independently a carbon atom, and a bond between Z 11 and Z 12 , a bond between Z 13 and Z 14 , and a bond between Z 15 and Z 16 are each independently a single bond or a double bond,
wherein, in Formulae 2-1 and 2-2,
X 21 is a single bond, O, S, N(R 25 ), or C(R 25 )(R 26 ),
L 21 and L 22 are each independently a substituted or unsubstituted C 5 -C 30 carbocyclic group or a substituted or unsubstituted C 1 -C 30 heterocyclic group,
a21 and a22 are each independently 0, 1, or 2,
R 21 and R 22 are each independently a substituted or unsubstituted C 6 -C 60 aryl group,
R 11 to R 16 and R 23 to R 26 are each independently hydrogen, deuterium, —F, —Cl, —Br, —I, —SF 5 , 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 ), —C(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 ),
b11 to b16 are each independently 0, 1, 2, or 3,
b23 and b24 are each independently 0, 1, 2, 3, or 4,
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 heteropolycyclic group, a C 1 -C 60 alkyl group that is substituted with at least one deuterium, —F, a cyano group, a C 1 -C 60 alkyl group, a C 6 -C 60 aryl group, or a combination thereof, or a C 6 -C 60 aryl group that is substituted with deuterium, —F, a cyano group, a C 1 -C 60 alkyl group, a C 6 -C 60 aryl group, or a combination thereof, and
* indicates a binding site to a neighboring atom.
2 . The heterocyclic compound of claim 1 , wherein the heterocyclic compound is represented by one of Formula 1-111:
wherein, in Formula 1-111,
R 110 to R 114 may each independently be X 11 , Y 11 , or R 11 ,
R 121 to R 124 may each independently be X 12 , Y 12 , or R 12 ,
R 131 to R 133 may each independently be X 13 , Y 13 , or R 13 ,
R 141 to R 143 may each independently be X 14 , Y 14 , or R 14 ,
R 151 to R 154 may each independently be X 15 , Y 15 , or R 15 ,
R 161 to R 164 may each independently be X 16 , Y 16 , or R 16 , and
X 11 to X 16 , Y 11 to Y 16 , and R 11 to R 16 are respectively the same as described in claim 1 .
3 . The heterocyclic compound of claim 1 , wherein X 11 to X 16 are each independently a group represented by Formula 2-11 or 2-21:
wherein, in Formulae 2-11 and 2-21,
L 21 and L 22 are respectively the same as described in claim 1 ,
a21 and a22 are each independently 0 or 1, and
R 201 to R 218 are each independently hydrogen, deuterium, —F, —Cl, —Br, —I, —SF 5 , 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 1 -C 60 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 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, or a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group.
4 . The heterocyclic compound of claim 1 , wherein X 11 to X 16 are each independently represented by one of Formulae 2-111 to 2-122:
wherein, in Formulae 2-111 to 2-122,
t-Bu represents a tert-butyl group, and
* indicates a binding site to a neighboring atom.
5 . The heterocyclic compound of claim 1 , wherein Y 11 to Y 16 are each independently a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, an adamantanyl group, a norbornanyl group, a norbornenyl group, a cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, a bicyclo[1.1.1]pentyl group, a bicyclo[2.1.1]hexyl group, a bicyclo[2.2.1]heptyl group, a bicyclo[2.2.2]octyl group, a phenyl group, a (C 1 -C 20 alkyl)phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a fluorenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, or a chrysenyl group, each substituted or unsubstituted 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 20 alkyl group, a deuterated C 2 -C 20 alkyl group, a C 1 -C 20 alkoxy group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, an adamantanyl group, a norbornanyl group, a norbornenyl group, a cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, a bicyclo[1.1.1]pentyl group, a bicyclo[2.1.1]hexyl group, a bicyclo[2.2.1]heptyl group, a bicyclo[2.2.2]octyl group, a (C 1 -C 20 )cyclopentyl group, a (C 1 -C 20 alkyl)cyclohexyl group, a (C 1 -C 20 alkyl)cycloheptyl group, a (C 1 -C 20 alkyl)cyclooctyl group, a (C 1 -C 20 alkyl) adamantanyl group, a (C 1 -C 20 alkyl) norbornanyl group, a (C 1 -C 20 alkyl) norbornenyl group, a (C 1 -C 20 )cyclopentenyl group, a (C 1 -C 20 )cyclohexenyl group, a (C 1 -C 20 alkyl)cycloheptenyl group, a (C 1 -C 20 alkyl) bicyclo[1.1.1]pentyl group, a (C 1 -C 20 alkyl) bicyclo[2.1.1]hexyl group, a (C 1 -C 20 alkyl) bicyclo[2.2.1]heptyl group, a (C 1 -C 20 alkyl) bicyclo[2.2.2]octyl group, a phenyl group, a (C 1 -C 20 alkyl)phenyl group, a biphenyl group, a terphenyl 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, or any combination thereof.
6 . The heterocyclic compound of claim 1 , wherein the sum of n11 to n15 in Formula 1-1 is 1 or 2.
7 . The heterocyclic compound of claim 1 , wherein the sum of m11 to m16 in Formula 1-1 is 1 or more.
8 . The heterocyclic compound of claim 1 , wherein, in Formula 1-1, the combined sum of n11 to n15 and m11 to m15 is 2, 3, 4, or 5.
9 . The heterocyclic compound of claim 1 , wherein the heterocyclic compound is represented by one of Formulae 1-11 to 1-24:
wherein, in Formulae 1-11 to 1-24,
A 11 to A 16 , X 11 to X 16 , Y 11 to Y 16 , Z 11 to Z 16 , R 11 to R 16 , and b11 to b16 are respectively the same as described in claim 1 ,
n11 to n15 are each independently 1 or 2,
m11 to m15 are each independently 0, 1, or 2, and
the combined sum of n11 to n15 and m11 to m15 is 3 or more.
10 . The heterocyclic compound of claim 1 , wherein the heterocyclic compound is one of the following Compounds:
11 . An organic light-emitting device comprising:
a first electrode;
a second electrode; and
an organic layer arranged between the first electrode and the second electrode and comprising an emission layer, wherein
the organic layer comprises the heterocyclic compound of claim 1 .
12 . The organic light-emitting device of claim 11 , wherein the emission layer comprises the heterocyclic compound.
13 . The organic light-emitting device of claim 12 , wherein the emission layer further comprises a host, and the host is different from the heterocyclic compound.
14 . The organic light-emitting device of claim 13 , wherein the emission layer emits blue light.
15 . The organic light-emitting device of claim 13 , further comprising an emitter that is a fluorescent emitter and/or a delayed fluorescence emitter.
16 . The organic light-emitting device of claim 12 , wherein the emission layer further comprises a host, and a sensitizer, wherein the host, the heterocyclic compound, and the sensitizer are different from each other.
17 . The organic light-emitting device of claim 16 , wherein the emission layer emits blue light.
18 . The organic light-emitting device of claim 16 , further comprising an emitter that is a fluorescent emitter and/or a delayed fluorescence emitter.
19 . An electronic apparatus comprising the organic light-emitting device of claim 11 .
20 . An organic light-emitting device comprising:
a first electrode;
a second electrode; and
an organic layer arranged between the first electrode and the second electrode and comprising an emission layer, wherein
the emission layer comprises the heterocyclic compound of claim 1 ,
wherein the emission layer comprises a host, and a sensitizer, and the heterocyclic compound of claim 1 , wherein the host, the heterocyclic compound, and the sensitizer are different from each other, and
wherein the heterocyclic compound satisfies Condition 5:
0 μs< T decay (HC)<5 μs Condition 5
wherein, in Condition 5,
T decay (HC) indicates a decay time of the heterocyclic compound.
21 . A heterocyclic compound represented by Formula 1-1 or 1-2, and
wherein the heterocyclic compound satisfies Condition 5:
wherein, in Formulae 1-1 and 1-2,
A 11 to A 16 are each independently a substituted or unsubstituted C 5 -C 30 carbocyclic group or a substituted or unsubstituted C 1 -C 30 heterocyclic group,
X 11 to X 16 are each independently a group represented by Formula 2-1 or 2-2,
n11 to n16 are each independently 0, 1, or 2,
the sum of n11 to n16 in Formula 1-1 is 1 or more, and the sum of n11 to n15 in Formula 1-2 is 1 or more,
Y 11 to Y 16 are each independently 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 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, or a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group,
m11 to m16 are each independently 0, 1, or 2,
the combined sum of n11 to n16 and m11 to m16 in Formula 1-1 is 2 or more, and the combined sum of n11 to n15 and m11 to m15 in Formula 1-2 is 2 or more,
Z 11 to Z 16 are each independently a carbon atom, and a bond between Z 11 and Z 12 , a bond between Z 13 and Z 14 , and a bond between Z 15 and Z 16 are each independently a single bond or a double bond,
wherein, in Formulae 2-1 and 2-2,
X 21 is a single bond, O, S, N(R 25 ), or C(R 25 )(R 26 ),
L 21 and L 22 are each independently a substituted or unsubstituted C 5 -C 30 carbocyclic group or a substituted or unsubstituted C 1 -C 30 heterocyclic group,
a21 and a22 are each independently 0, 1, or 2,
R 21 and R 22 are each independently a substituted or unsubstituted C 6 -C 60 aryl group,
R 11 to R 16 and R 23 to R 26 are each independently hydrogen, deuterium, —F, —Cl, —Br, —I, —SF 5 , 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 ), —C(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 ),
b11 to b16 are each independently 0, 1, 2, or 3,
b23 and b24 are each independently 0, 1, 2, 3, or 4,
Q 1 to Q 3 are each independently hydrogen, deuterium, —F, —C 1 , —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 heteropolycyclic group, a C 1 -C 60 alkyl group that is substituted with at least one deuterium, —F, a cyano group, a C 1 -C 60 alkyl group, a C 6 -C 60 aryl group, or a combination thereof, or a C 6 -C 60 aryl group that is substituted with deuterium, —F, a cyano group, a C 1 -C 60 alkyl group, a C 6 -C 60 aryl group, or a combination thereof, and
* indicates a binding site to a neighboring atom,
0 μs< T decay (HC)<5 μs Condition 5
wherein, in Condition 5,
T decay (HC) indicates a decay time of the heterocyclic compound.