HETEROCYCLIC COMPOUND, ORGANIC LIGHT-EMITTING DEVICE INCLUDING THE SAME, AND ELECTRONIC APPARATUS INCLUDING THE ORGANIC LIGHT-EMITTING DEVICE
Provided are a heterocyclic compound, an organic light-emitting device including the heterocyclic compound, and an electronic apparatus including the organic light-emitting device, the heterocyclic compound including: a group represented by Formula 1; a group represented by Formula 2; and one to four groups each independently represented by Formula 3 or 4: The substituents in Formulae 1 to 4 are the same as described in the detailed description.
1 . A heterocyclic compound comprising:
a group represented by Formula 1;
a group represented by Formula 2; and
one to four groups each independently represented by Formula 3 or 4:
wherein, in Formulae 1 to 4,
at least one of: Ar 1 and Ar 2 ; Ar 1 and Cy 1 , or a combination thereof are linked to each other via the group represented by Formula 2,
Cy 1 , Cy 2 , and Ar 1 to Ar 6 are each independently a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 30 ring-forming atoms or a substituted or unsubstituted aromatic hetero ring having 5 to 30 ring-forming atoms,
X 1 and X 2 are each independently O, S, NR, CR′R″, or a single bond, wherein R, R′, and R″ are each independently a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group,
Y is O, S, NZ, or CZ′Z″, wherein Z, Z′, and Z″ are each independently a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group,
Z in NZ is optionally bonded to Cy 1 , Cy 2 , or Ara via O, S, NZ, CZ′Z″, or a single bond,
* in Formula 2 indicates a binding site to Ar 1 , Ar 2 , or Cy 1 , and
two *(s) in Formulae 3 and 4 each indicate a binding site to Cy 1 or Cy 2 in Formula 1.
2 . The heterocyclic compound of claim 1 , wherein Cy 1 , Cy 2 , and Ar 1 to Ar 6 are each independently an aromatic hydrocarbon ring having 6 to 10 ring-forming atoms or an aromatic hetero ring having 5 to 20 ring-forming atoms.
3 . The heterocyclic compound of claim 1 , wherein a substituent of the substituted aromatic hydrocarbon ring and the substituted aromatic hetero ring is independently a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted heteroaryloxy group, a substituted or unsubstituted diarylamino group, a substituted or unsubstituted diheteroaryl amino group, or a substituted or unsubstituted arylheteroaryl amino group.
4 . The heterocyclic compound of claim 1 , wherein a substituent of the substituted aromatic hydrocarbon ring and the substituted aromatic hetero ring is a tert-butyl group, a phenyl group, a 4-tert-butyl phenyl group, a 2,4,6-trimethyl phenyl group, a 4-(2,4,6-trimethylphenyl)phenyl group, a 2,5-diphenylphenyl group, a 3,5-diphenylphenyl group, a biphenyl group, a 2-pyridyl group, a 3-pyridyl group, a 4-pyridyl group, a carbazolyl group, a 3,6-di-tert-butylcarbazolyl group, a diphenylamino group, or a bis(4-tert-butylphenyl)amino group.
5 . The heterocyclic compound of claim 1 , wherein, in the heterocyclic compound, a moiety represented by Formulae 1 and 2 is represented by one of Formulae 5-1 to 5-3:
wherein, in Formulae 5-1 to 5-3,
one to four groups represented by at least one of Formulae 3, 4, or a combination thereof are bonded to at least one of Cy 1 , Cy 2 , or a combination thereof.
two *(s) in Formulae 3 and 4 each indicate a binding site to Cy 1 or Cy 2 in Formulae 5-1 to 5-3, and
Cy 1 , Cy 2 , Ar 1 , Ar 2 , X 1 , X 2 , and Y are the same as those described in claim 1 , respectively.
6 . The heterocyclic compound of claim 1 , wherein the heterocyclic compound is represented by one of Formulae 6-1 to 6-4:
wherein, in Formulae 6-1 to 6-4,
Cy 1 , Cy 2 , Ar 1 , Ar 2 , X 1 , X 2 , and Y are the same as those as described in claim 1 , respectively.
7 . The heterocyclic compound of claim 1 , wherein the heterocyclic compound is represented by one of Formulae 1 to 43:
wherein, in Formulae 1 to 43,
X 1 and X 2 are each independently O, S, NR, CR′R″, or a single bond, wherein R, R′, and R″ are each independently a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group,
Y is O, S, NZ, or CZ′Z″, wherein Z, Z′, and Z″ are each independently a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group,
Z in NZ is optionally bonded to Cy 1 , Cy 2 , or Ar 3 via O, S, NZ, CZ′Z″, or a single bond, and
at least one hydrogen atom of Formulae 1 to 43 is optionally substituted with a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, or a substituted or unsubstituted diarylamino group.
8 . The light-emitting device of claim 1 , wherein the heterocyclic compound is a compound of Group I:
Group I
9 . The heterocyclic compound of claim 1 , wherein a highest occupied molecular orbital (HOMO) energy level of the heterocyclic compound is about −5.8 eV to about −4.6 eV, and
a lowest unoccupied molecular orbital (LUMO) energy level of the heterocyclic compound is about −2.4 eV to about −0.8 eV.
10 . The heterocyclic compound of claim 1 , wherein a peak of a fluorescence wavelength of the heterocyclic compound is about 360 nm to about 515 nm, and a full width at half maximum (FWHM) of a peak of a fluorescence spectrum of the heterocyclic compound is about 30 nm or less.
11 . The heterocyclic compound of claim 1 , wherein ΔE ST of the heterocyclic compound is about 0.4 eV or less.
12 . The heterocyclic compound of claim 1 , wherein an oscillator strength of a stable structure in an adiabatic first excited singlet state of the heterocyclic compound is about 0.22 or more.
13 . The light-emitting device of claim 1 , wherein a reorganization energy of the heterocyclic compound is about 0.1 eV or less.
14 . An organic light-emitting device comprising:
a first electrode; a second electrode; an organic layer comprising an emission layer located 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 do not each emit light, and the dopant emits light.
20 . An electronic apparatus comprising the organic light-emitting device of claim 14 .