Heterocyclic compound and organic light emitting element comprising same
The present specification provides a heterocyclic compound and an organic light emitting device including the same.
1. An organic light emitting device comprising:
a first electrode;
a second electrode; and
an organic material layer disposed between the first electrode and the second electrode,
wherein the organic material layer comprises at least one selected from an electron transfer layer, an electron injection layer, a layer carrying out electron transfer and electron injection at the same time, a hole transfer layer, an electron blocking layer, a layer carrying out hole transfer and electron blocking at the same time, a hole injection layer, or a layer carrying out hole injection and hole transfer at the same time, and the electron transfer layer, the electron injection layer, the layer carrying out electron transfer and electron injection at the same time, the hole transfer layer, the electron blocking layer, the layer carrying out hole transfer and electron blocking at the same time, the hole injection layer, or the layer carrying out hole injection and hole transfer at the same time comprises a compound represented by the following Chemical Formula 1:
wherein, in Chemical Formula 1,
X is O or S;
one of A or B has a structure of the following Chemical Formula 1-1, and the other one of A or B is an aryl group that is optionally substituted with a substituent that is not a carbazole group, wherein a carbon atom of the aryl group is directly bonded to the
of Chemical Formula 1; or a heterocyclic group selected from a dibenzothiophene group optionally substituted with an aryl group, or a dibenzofuranyl group that is optionally substituted, and a carbon atom of the heterocyclic group is directly bonded to the
of Chemical Formula 1,
wherein, in Chemical Formula 1-1, L1 is a direct bond; or a substituted or unsubstituted arylene group; and
Ar1 and Ar2 are the same as or different from each other, and each independently hydrogen; deuterium; a halogen group; a nitrile group; a nitro group; a hydroxyl group; a carbonyl group; an ester group; an imide group; an amino group; a substituted or unsubstituted silyl group; a substituted or unsubstituted boron group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted alkoxy group; a substituted or unsubstituted aryloxy group; a substituted or unsubstituted alkylthioxy group; a substituted or unsubstituted arylthioxy group; a substituted or unsubstituted alkylsulfoxy group; a substituted or unsubstituted arylsulfoxy group; a substituted or unsubstituted alkenyl group; a substituted or unsubstituted aralkyl group; a substituted or unsubstituted alkylaryl group; a substituted or unsubstituted alkylamine group; a substituted or unsubstituted aralkylamine group; a substituted or unsubstituted heteroarylamine group; a substituted or unsubstituted arylamine group; a substituted or unsubstituted arylphosphine group; a substituted or unsubstituted phosphine oxide group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heterocyclic group, provided that Ar1 and Ar2 are not both a naphthyl group, and that when Ar1 and Ar2 are both a phenyl group, L1 is a substituted or unsubstituted arylene group.
2. The organic light emitting device of claim 1 , wherein the compound represented by Chemical Formula 1 is represented by the following Chemical Formula 1-A or Chemical Formula 1-B:
wherein, in Chemical Formulae 1-A and 1-B,
definitions of X, L1, Ar1 and Ar2 are the same as in Chemical Formula 1 and Chemical Formula 1-1, and
A and B are each independently an aryl group that is optionally substituted with a substituent that is not a carbazole group, wherein a carbon atom of the aryl group is directly bonded to the
of Chemical Formula 1-A and 1-B, respectively; or a heterocyclic group selected from a dibenzothiophene group optionally substituted with an aryl group, or a dibenzofuranyl group that is optionally substituted, and a carbon atom of the heterocyclic group is directly bonded to the
of Chemical Formulae 1-A and 1-B, respectively.
3. The organic light emitting device of claim 1 , wherein the compound represented by Chemical Formula 1 is represented by any one of the following Chemical Formula 21 to Chemical Formula 24:
wherein, in Chemical Formulae 21 to 24,
definitions of Ar1 and Ar2 are the same as in Chemical Formula 1 and Chemical Formula 1-1, and
A and B are each independently an aryl group that is optionally substituted with a substituent that is not a carbazole group, wherein a carbon atom of the aryl group is directly bonded to the
of Chemical Formulae 21 and 23, and
of Chemical Formulae 22 and 24, respectively; or a heterocyclic group that is optionally substituted, wherein the heterocyclic group is a dibenzothiophene group or a dibenzofuranyl group, and a carbon atom of the heterocyclic group is directly bonded to the
of Chemical Formulae 21 and 23, and
of Chemical Formulae 22 and 24, respectively.
4. The organic light emitting device of claim 1 , wherein L1 is any one selected from among the following structures:
5. The organic light emitting device of claim 1 , wherein Ar1 and Ar2 are the same as or different from each other, and each independently hydrogen, a substituted or unsubstituted aryl group having 6 to 40 carbon atoms; or a substituted or unsubstituted heterocyclic group having 2 to 40 carbon atoms.
6. The organic light emitting device of claim 1 , wherein the compound of Chemical Formula 1 is any one selected from among the following structures:
7. The organic light emitting device of claim 1 , wherein the organic material layer comprises at least one of an electron transfer layer, an electron injection layer, or a layer carrying out electron transfer and electron injection at the same time, and the electron transfer layer, the electron injection layer, or the layer carrying out electron transfer and electron injection at the same time comprises the compound.
8. The organic light emitting device of claim 1 , wherein the organic material layer comprises at lease one of a hole transfer layer, an electron blocking layer, or a layer carrying out hole transfer and electron blocking at the same time, and the hole transfer layer, the electron blocking layer, or the layer carrying out hole transfer and electron blocking at the same time comprises the compound.
9. The organic light emitting device of claim 1 , wherein the organic material layer comprises at least one of a hole injection layer, a hole transfer layer, or a layer carrying out hole injection and hole transfer at the same time, and the hole injection layer, the hole transfer layer, or the layer carrying out hole injection and hole transfer at the same time comprises the compound.
10. The organic light emitting device of claim 1 , wherein the organic material layer comprises the compound represented by Chemical Formula 1 as a host, and comprises other organic compounds, metals or metal compounds as a dopant.
11. The organic light emitting device of claim 1 , wherein the organic material layer further comprises a light emitting layer, and the light emitting layer comprises a compound represented by the following Chemical Formula A-1:
wherein, in Chemical Formula A-1,
X1 is a substituted or unsubstituted monovalent or higher benzofluorene group; a substituted or unsubstituted monovalent or higher fluoranthene group; a substituted or unsubstituted monovalent or higher pyrene group; or a substituted or unsubstituted monovalent or higher chrysene group;
L is a direct bond; a substituted or unsubstituted arylene group; or a substituted or unsubstituted heteroarylene group;
X2 and X3 are the same as or different from each other, and each independently a substituted or unsubstituted aryl group; a substituted or unsubstituted silyl group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted aralkyl group; or a substituted or unsubstituted heteroaryl group, or bond to each other to form a substituted or unsubstituted ring;
r is an integer of 1 or greater; and
when r is 2 or greater, each NX2X3L is the same as or different from each other.
12. The organic light emitting device of claim 11 , wherein L is a direct bond, X1 is a substituted or unsubstituted divalent pyrene group, X2 and X3 are the same as or different from each other and each independently an aryl group unsubstituted or substituted with a germanium group, and r is 2.
13. The organic light emitting device of claim 1 , wherein the organic material layer further comprises a light emitting layer, and the light emitting layer comprises a compound represented by the following Chemical Formula A-2:
wherein, in Chemical Formula A-2,
X4 is a 1-naphthyl group, a 2-naphthyl group, a 1-anthryl group, a 2-anthryl group, a 1-phenanthryl group, a 2-phenanthryl group, a 3-phenanthryl group, a 4-phenanthryl group, a 9-phenanthryl group, a 1-naphthacenyl group, a 2-naphthacenyl group, a 9-naphthacenyl group, a 1-pyrenyl group, a 2-pyrenyl group, a 4-pyrenyl group, a 3-methyl-2-naphthyl group, a 4-methyl-1-naphthyl group or the following chemical formula
X6 is a phenyl group, a 1-naphthyl group, a 2-naphthyl group, a 1-anthryl group, a 2-anthryl group, a 1-phenanthryl group, a 2-phenanthryl group, a 3-phenanthryl group, a 4-phenanthryl group, a 9-phenanthryl group, a 1-naphthacenyl group, a 2-naphthacenyl group, a 9-naphthacenyl group, a 1-pyrenyl group, a 2-pyrenyl group, a 4-pyrenyl group, a 2-biphenylyl group, a 2-biphenylyl group, a 3-biphenylyl group, a 4-biphenylyl group, a p-terphenyl-4-yl group, a p-terphenyl-3-yl group, a p-terphenyl-2-yl group, an m-terphenyl-4-yl group, an m-terphenyl-3-yl group, an m-terphenyl-2-yl group, an o-tolyl group, an m-tolyl group, a p-tolyl group, a p-t-butylphenyl group, a p-(2-phenylpropyl)phenyl group, a 3-methyl-2-naphthyl group, a 4-methyl-1-naphthyl group, a 4-methyl-1-anthryl group, a 4′-methylbiphenyl group, a 4″-t-butyl-p-terphenyl-4-yl group or a 3-fluoranthenyl group;
X5 and X7 are the same as or different from each other, and each independently hydrogen; a substituted or unsubstituted alkyl group; a substituted or unsubstituted alkoxy group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group;
p2 is an integer of 1 to 5;
p1 and p3 are each an integer of 1 to 4; and
when p1 to p3 are each 2 or greater, each of X5, X6 and X7 is the same as or different from each other.
14. The organic light emitting device of claim 13 , wherein X4 is a 1-naphthyl group and X6 is a 2-naphthyl group.
15. The organic light emitting device of claim 11 , wherein the light emitting layer further comprises a compound represented by the following Chemical Formula A-2:
wherein, in Chemical Formula A-2,
X4 is a 1-naphthyl group, a 2-naphthyl group, a 1-anthryl group, a 2-anthryl group, a 1-phenanthryl group, a 2-phenanthryl group, a 3-phenanthryl group, a 4-phenanthryl group, a 9-phenanthryl group, a 1-naphthacenyl group, a 2-naphthacenyl group, a 9-naphthacenyl group, a 1-pyrenyl group, a 2-pyrenyl group, a 4-pyrenyl group, a 3-methyl-2-naphthyl group, a 4-methyl-1-naphthyl group or the following chemical formula
X6 is a phenyl group, a 1-naphthyl group, a 2-naphthyl group, a 1-anthryl group, a 2-anthryl group, a 1-phenanthryl group, a 2-phenanthryl group, a 3-phenanthryl group, a 4-phenanthryl group, a 9-phenanthryl group, a 1-naphthacenyl group, a 2-naphthacenyl group, a 9-naphthacenyl group, a 1-pyrenyl group, a 2-pyrenyl group, a 4-pyrenyl group, a 2-biphenylyl group, a 2-biphenylyl group, a 3-biphenylyl group, a 4-biphenylyl group, a p-terphenyl-4-yl group, a p-terphenyl-3-yl group, a p-terphenyl-2-yl group, an m-terphenyl-4-yl group, an m-terphenyl-3-yl group, an m-terphenyl-2-yl group, an o-tolyl group, an m-tolyl group, a p-tolyl group, a p-t-butylphenyl group, a p-(2-phenylpropyl)phenyl group, a 3-methyl-2-naphthyl group, a 4-methyl-1-naphthyl group, a 4-methyl-1-anthryl group, a 4′-methylbiphenyl group, a 4″-t-butyl-p-terphenyl-4-yl group or a 3-fluoranthenyl group;
X5 and X7 are the same as or different from each other, and each independently hydrogen; a substituted or unsubstituted alkyl group; a substituted or unsubstituted alkoxy group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group;
p2 is an integer of 1 to 5;
p1 and p3 are each an integer of 1 to 4; and
when p1 to p3 are each 2 or greater, each of X5, X6 and X7 is the same as or different from each other.