Heterocyclic compound, and organic light-emitting element using same
The present specification relates to a heterocyclic compound represented by Chemical Formula 1, and an organic light emitting device using the same.
1. A heterocyclic compound represented by the following Chemical Formula 1:
wherein, in Chemical Formula 1,
X is O; S; or NR;
L1 to L3 are the same as or different from each other, and each independently a direct bond; a substituted or unsubstituted arylene group having 6 to 60 carbon atoms; or a substituted or unsubstituted heteroarylene group having 2 to 60 carbon atoms;
Z1 to Z3 are the same as or different from each other, and each independently selected from the group consisting of hydrogen; deuterium; a halogen group; a cyano group; —P(═O)(R104)(R105); —N(R106)(R107); a substituted or unsubstituted alkyl group having 1 to 60 carbon atoms; a substituted or unsubstituted alkenyl group having 2 to 60 carbon atoms; a substituted or unsubstituted alkynyl group having 2 to 60 carbon atoms; a substituted or unsubstituted alkoxy group having 1 to 60 carbon atoms; a substituted or unsubstituted cycloalkyl group having 3 to 60 carbon atoms; a substituted or unsubstituted heterocycloalkyl group having 2 to 60 carbon atoms; a substituted or unsubstituted aryl group having 6 to 60 carbon atoms; and a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms;
R1 and R2 are the same as or different from each other, and each independently selected from the group consisting of hydrogen; deuterium; a halogen group; a cyano group; —P(═O)(R104′)(R105′); —N(R106′)(R107′); a substituted or unsubstituted alkyl group having 1 to 60 carbon atoms; a substituted or unsubstituted alkenyl group having 2 to 60 carbon atoms; a substituted or unsubstituted alkynyl group having 2 to 60 carbon atoms; a substituted or unsubstituted alkoxy group having 1 to 60 carbon atoms; a substituted or unsubstituted cycloalkyl group having 3 to 60 carbon atoms; a substituted or unsubstituted heterocycloalkyl group having 2 to 60 carbon atoms; a substituted or unsubstituted aryl group having 6 to 60 carbon atoms; and a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms, or adjacent two or more groups bond to each other to form a substituted or unsubstituted aliphatic hydrocarbon ring; a substituted or unsubstituted aromatic hydrocarbon ring; a substituted or unsubstituted aliphatic heteroring; or a substituted or unsubstituted aromatic heteroring;
R is hydrogen; deuterium; a halogen group; a cyano group; a substituted or unsubstituted alkyl group having 1 to 60 carbon atoms; a substituted or unsubstituted alkenyl group having 2 to 60 carbon atoms; a substituted or unsubstituted alkynyl group having 2 to 60 carbon atoms; a substituted or unsubstituted alkoxy group having 1 to 60 carbon atoms; a substituted or unsubstituted cycloalkyl group having 3 to 60 carbon atoms; a substituted or unsubstituted heterocycloalkyl group having 2 to 60 carbon atoms; a substituted or unsubstituted aryl group having 6 to 60 carbon atoms; or a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms;
R104 to R107 and R104′ to R107′ are each independently hydrogen; deuterium; a halogen group; an alkyl group; an alkenyl group; an alkoxy group; a cycloalkyl group; an aryl group; or a heteroaryl group;
m, p, x, n, q and y are each an integer of 1 to 5;
a is an integer of 1 to 3; and
when m, p, x, n, q, y and a are each an integer of 2 or greater, substituents in the parentheses are the same as or different from each other.
2. The heterocyclic compound of claim 1 , wherein Chemical Formula 1 is represented by one of the following Chemical Formulae 2 to 5:
in Chemical Formula 2 to Chemical Formula 5,
X, m, p, x, n, q, y, a and R have the same definitions as in Chemical Formula 1,
L11 to L13 are the same as or different from each other, and each independently a direct bond; a substituted or unsubstituted arylene group having 6 to 60 carbon atoms; or a substituted or unsubstituted heteroarylene group having 2 to 60 carbon atoms,
Z11 to Z13 are the same as or different from each other, and each independently selected from the group consisting of a cyano group; —P(═O)(R104)(R105); a substituted or unsubstituted aryl group having 6 to 60 carbon atoms; and a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms,
R11 and R12 are the same as or different from each other, and each independently selected from the group consisting of hydrogen; deuterium; a halogen group; a cyano group; —P(═O)(R104′)(R105′); —N(R106′)(R107′); a substituted or unsubstituted alkyl group having 1 to 60 carbon atoms; a substituted or unsubstituted alkenyl group having 2 to 60 carbon atoms; a substituted or unsubstituted alkynyl group having 2 to 60 carbon atoms; a substituted or unsubstituted alkoxy group having 1 to 60 carbon atoms; a substituted or unsubstituted cycloalkyl group having 3 to 60 carbon atoms; and a substituted or unsubstituted heterocycloalkyl group having 2 to 60 carbon atoms,
R104, R105 and R104′ to R107′ are each independently hydrogen; deuterium; a halogen group; an alkyl group; an alkenyl group; an alkoxy group; a cycloalkyl group; an aryl group; or a heteroaryl group,
b is 1 or 2,
c is an integer of 1 to 4,
when b is 2, two R11s are the same as or different from each other, and
when c is 2 or greater, a plurality of R12s are the same as or different from each other.
3. The heterocyclic compound of claim 1 , wherein R1 and R2 are hydrogen.
4. The heterocyclic compound of claim 1 , wherein L1 to L3 are the same as or different from each other, and each independently a direct bond; a phenylene group unsubstituted or substituted with a halogen group; a biphenylene group; or a terphenylene group.
5. The heterocyclic compound of claim 1 , wherein R is a substituted or unsubstituted aryl group having 6 to 60 carbon atoms.
6. The heterocyclic compound of claim 1 , wherein Z1 to Z3 are the same as or different from each other, and each independently hydrogen; deuterium; a cyano group; —P(═O)(R104)(R105); a substituted or unsubstituted aryl group having 6 to 40 carbon atoms; or a substituted or unsubstituted heteroaryl group having 2 to 40 carbon atoms.
7. The heterocyclic compound of claim 1 , wherein Chemical Formula 1 is represented by any one of the following compounds:
8. An organic light emitting device comprising:
a first electrode;
a second electrode; and
one or more organic material layers provided between the first electrode and the second electrode,
wherein one or more layers of the organic material layers include the heterocyclic compound of claim 1 .
9. The organic light emitting device of claim 8 , wherein the organic material layer includes an electron transfer layer, and the electron transfer layer includes the heterocyclic compound.
10. The organic light emitting device of claim 8 , wherein the organic material layer includes a hole blocking layer, and the hole blocking layer includes the heterocyclic compound.
11. The organic light emitting device of claim 8 , further comprising one, two or more layers selected from the group consisting of a light emitting layer, a hole injection layer, a hole transfer layer, an electron injection layer, an electron transfer layer, an electron blocking layer and a hole blocking layer.
12. The organic light emitting device of claim 8 comprising:
a first stack provided on the first electrode and including a first light emitting layer;
a charge generation layer provided on the first stack;
a second stack provided on the charge generation layer and including a second light emitting layer; and
the second electrode provided on the second stack.
13. The organic light emitting device of claim 12 , wherein the charge generation layer includes the heterocyclic compound.
14. The organic light emitting device of claim 12 , wherein the charge generation layer includes an N-type charge generation layer, and the N-type charge generation layer includes the heterocyclic compound.
15. The organic light emitting device of claim 12 , wherein the second stack further includes a hole injection layer, and the hole injection layer includes the heterocyclic compound.