Heterocyclic compound, organic light-emitting device including the same, and electronic apparatus including the organic light-emitting device
Provided are a heterocyclic compound represented by Formula 1, an organic light-emitting device including the same, and an electronic apparatus including the organic light-emitting device: The substituents in Formula 1 are the same as described in the detailed description.
1 . A heterocyclic compound represented by Formula 1:
wherein, in Formula 1,
X 1 , X 2 , X 3 , and X 4 are each independently C or N, and at least one of three X 1 (s), four X 2 (s), three X 3 (s), four X 4 (s), or any combination thereof is N,
Y 1 and Y 2 are each independently C or N, and at least one of Y 1 and Y 2 is N,
R 1 , R 2 , R 3 , and R 4 are each independently a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted aryl group having 6 to 14 ring-forming atoms, a substituted or unsubstituted heteroaryl group having 5 to 14 ring-forming atoms, a substituted or unsubstituted amino group, a substituted or unsubstituted arylamino group having 6 to 14 ring-forming atoms, a substituted or unsubstituted heteroarylamino group having 5 to 14 ring-forming atoms, or a substituted or unsubstituted arylboranyl group having 6 to 14 ring-forming atoms,
R 5 is a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted aryl group having 6 to 14 ring-forming atoms, a substituted or unsubstituted heteroaryl group having 5 to 14 ring-forming atoms, a substituted or unsubstituted amino group, a substituted or unsubstituted arylamino group having 6 to 14 ring-forming atoms, a substituted or unsubstituted heteroarylamino group having 5 to 14 ring-forming atoms, a substituted or unsubstituted indolo[3,2,1-jk]carbazolyl group, or —R 51 —R 52 ,
R 51 is a substituted or unsubstituted arylene group having 6 to 14 ring-forming atoms or a substituted or unsubstituted heteroarylene group having 5 to 14 ring-forming atoms,
R 52 is a substituted or unsubstituted amino group, a substituted or unsubstituted arylamino group having 6 to 14 ring-forming atoms, a substituted or unsubstituted hetero arylamino group having 5 to 14 ring-forming atoms, or a substituted or unsubstituted heteroaryl group having 5 to 14 ring-forming atoms,
n1 and n2 are each independently 1, 2, 3, or 4,
m1 and m2 are each independently 1, 2, or 3, and
m3 is 0, 1, or 2.
2 . The heterocyclic compound of claim 1 , wherein R 1 , R 2 , R 3 , and R 4 are each independently a hydrogen atom, a substituted or unsubstituted phenyl group, a substituted or unsubstituted pyridyl group, a substituted or unsubstituted biphenylboranyl group, or a monovalent group represented by Formula B1:
wherein, in Formula B1, * indicates a binding site to a neighboring atom.
3 . The heterocyclic compound of claim 1 , wherein at least one of X 1 (s) is N, at least one of X 2 (s) is N, at least one of X 3 (s) is N, and at least one of X 4 (s) is N.
4 . The heterocyclic compound of claim 1 , wherein n1 and n2 are each 3, and
m1 and m2 are each 2.
5 . The heterocyclic compound of claim 1 , wherein, when two of X 1 (s) and two of X 3 (s) are each C, and m1 and m2 are each 2, one of R 1 (s) and one of R 3 (s) are each a hydrogen atom, and another one of R 1 (s) and another one of R 3 (s) are each a substituted or unsubstituted phenyl group, a substituted or unsubstituted pyridyl group, a substituted or unsubstituted biphenylboranyl group, or a monovalent group represented by Formula B1:
wherein, in Formula B1, * indicates a binding site to a neighboring atom.
6 . The heterocyclic compound of claim 1 , wherein, when three of X 2 (s) and three of X 4 (s) are each C, and n1 and n2 are each 3, two of R 2 (s) and two of R 4 (s) are each a hydrogen atom, and another one of R 2 (s) and another one of R 4 (s) are each a substituted or unsubstituted phenyl group, a substituted or unsubstituted pyridyl group, a substituted or unsubstituted biphenylboranyl group, or a monovalent group represented by Formula B1:
wherein, in Formula B1, * indicates a binding site to a neighboring atom.
7 . The heterocyclic compound of claim 1 , wherein m3 is 1 or 2.
8 . The heterocyclic compound of claim 1 , wherein R 5 is a hydrogen atom, a substituted or unsubstituted phenyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted indolo[3,2,1-jk]carbazolyl group, a substituted or unsubstituted N,N-diphenylamino group, a substituted or unsubstituted phenoxazinyl group, or —R 51 -R 52 , and
R 51 is a phenylene group, and R 52 is a substituted or unsubstituted N,N-diphenylamino group or a substituted or unsubstituted phenoxazinyl group.
9 . The heterocyclic compound of claim 1 , wherein the heterocyclic compound is represented by one of Group X:
10 . The heterocyclic compound of claim 1 , wherein the heterocyclic compound is a compound of Group I:
11 . The heterocyclic compound of claim 1 , wherein a highest occupied molecular orbital (HOMO) energy level of the heterocyclic compound is about −6.50 eV to about −4.6 eV, and
a lowest unoccupied molecular orbital (LUMO) energy level of the heterocyclic compound is about −4.00 eV to about −2.60 eV.
12 . The heterocyclic compound of claim 1 , wherein a peak of a fluorescence wavelength of the heterocyclic compound is about 440 nm to about 480 nm, and
a full width at half maximum (FWHM) of a peak of a fluorescence spectrum of the heterocyclic compound is about 20 nm or less.
13 . The heterocyclic compound of claim 1 , wherein AEST of the heterocyclic compound is about 0.3 eV or less.
14 . An organic light-emitting device comprising:
a first electrode; a second electrode; an organic layer comprising an emission layer between the first electrode and the second electrode; and
the heterocyclic compound of claim 1 .
15 . The organic light-emitting device of claim 14 , wherein the emission layer comprises the heterocyclic compound.
16 . The organic light-emitting device of claim 15 , wherein the emission layer further comprises a host,
the host is different from the heterocyclic compound, and
the emission layer consists of the host and the heterocyclic compound.
17 . The organic light-emitting device of claim 16 , wherein the host does not emit light, and the heterocyclic compound emits light.
18 . The organic light-emitting device of claim 15 , wherein the emission layer further comprises a host and a dopant,
the host, the dopant, and the heterocyclic compound are different from each other, and
the emission layer consists of the host, the dopant, and the heterocyclic compound.
19 . The organic light-emitting device of claim 18 , wherein the host and the heterocyclic compound each do not emit light, and the dopant emits light.
20 . An electronic apparatus comprising the organic light-emitting device of claim 14 .