Organic light emitting device, method for manufacturing same and composition for organic material layer
The present specification relates to an organic light emitting device, a method for manufacturing the same, and a composition for an organic material layer.
1. 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 comprise a heterocyclic compound represented by the following Chemical Formula 1 and a heterocyclic compound represented by the following Chemical Formula 24:
in Chemical Formulae 1 and 24,
N-Het is a monocyclic or polycyclic heterocyclic group substituted or unsubstituted and comprising one or more Ns;
L and L1 are a direct bond; a substituted or unsubstituted C6 to C60 arylene group; or a substituted or unsubstituted C2 to C60 heteroarylene group, a is an integer of 1 to 3, and when a is 2 or greater, Ls are the same as or different from each other;
R1 to R14 are the same as or different from each other, and each independently selected from the group consisting of hydrogen; deuterium; halogen; a cyano group; a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C2 to C60 alkenyl group; a substituted or unsubstituted C2 to C60 alkynyl group; a substituted or unsubstituted C2 to C60 alkoxy group; a substituted or unsubstituted C3 to C60 cycloalkyl group; a substituted or unsubstituted C2 to C60 heterocycloalkyl group; a substituted or unsubstituted C6 to C60 aryl group; a substituted or unsubstituted C2 to C60 heteroaryl group; a substituted or unsubstituted phosphine oxide group; and a substituted or unsubstituted amine group, or two or more groups adjacent to each other bond to each other to form a substituted or unsubstituted C6 to C60 aromatic hydrocarbon ring or a substituted or unsubstituted C2 to C60 heteroring;
b and c are each an integer of 1 to 3;
when b is 2 or greater, R9s are the same as or different from each other, and when c is 2 or greater, R10s are the same as or different from each other;
m, p and q are an integer of 0 to 4;
n is an integer of 0 to 2;
when m is 2 or greater, R11s are the same as or different from each other, when n is an integer of 2, R12s are the same as or different from each other, when p is 2 or greater, R13s are the same as or different from each other, and when q is 2 or greater, R14s are the same as or different from each other;
Ar1 is a substituted or unsubstituted C6 to C60 aryl group; or a C2 to C60 heteroaryl group substituted or unsubstituted and comprising at least one of S and O; and
Ar2 is a substituted or unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 to C60 heteroaryl group.
2. The organic light emitting device of claim 1 , wherein Chemical Formula 1 is represented by the following Chemical Formula 2 or Chemical Formula 3:
in Chemical Formulae 2 and 3,
R1 to R10, L, N-Het, a, b and c have the same definitions as in Chemical Formula 1.
3. The organic light emitting device of claim 1 , wherein Chemical Formula 1 is represented by one of the following Chemical Formulae 12 to 14:
in Chemical Formulae 12 to 14,
X1 is CR21 or N, X2 is CR22 or N, X3 is CR23 or N, X4 is CR24 or N, X5 is CR25 or N, and at least one of X1 to X5 is N; and
R21 to R25 and R27 to R32 are the same as or different from each other, and each independently selected from the group consisting of hydrogen; deuterium; halogen; a cyano group; a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C2 to C60 alkenyl group; a substituted or unsubstituted C2 to C60 alkynyl group; a substituted or unsubstituted C2 to C60 alkoxy group; a substituted or unsubstituted C3 to C60 cycloalkyl group; a substituted or unsubstituted C2 to C60 heterocycloalkyl group; a substituted or unsubstituted C6 to C60 aryl group; a substituted or unsubstituted C2 to C60 heteroaryl group; a substituted or unsubstituted phosphine oxide group; and a substituted or unsubstituted amine group, or two or more groups adjacent to each other bond to each other to form a substituted or unsubstituted C6 to C60 aromatic hydrocarbon ring or a substituted or unsubstituted C2 to C60 heteroring.
4. The organic light emitting device of claim 3 , wherein
of Chemical Formula 12 is represented by one of the following Chemical Formulae 15 to 18:
in Chemical Formula 15, one or more of X1, X3 and X5 are N, and the rest have the same definitions as in Chemical Formula 12;
in Chemical Formula 16, one or more of X1, X2 and X5 are N, and the rest have the same definitions as in Chemical Formula 12;
in Chemical Formula 17, one or more of X1 to X3 are N, and the rest have the same definitions as in Chemical Formula 12;
in Chemical Formula 18, one or more of X1, X2 and X5 are N, and the rest have the same definitions as in Chemical Formula 12; and
R22, R24 and R33 to R36 are the same as or different from each other, and each independently selected from the group consisting of hydrogen; deuterium; halogen; a cyano group; a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C2 to C60 alkenyl group; a substituted or unsubstituted C2 to C60 alkynyl group; a substituted or unsubstituted C2 to C60 alkoxy group; a substituted or unsubstituted C3 to C60 cycloalkyl group; a substituted or unsubstituted C2 to C60 heterocycloalkyl group; a substituted or unsubstituted C6 to C60 aryl group; a substituted or unsubstituted C2 to C60 heteroaryl group; a substituted or unsubstituted phosphine oxide group; and a substituted or unsubstituted amine group, or two or more groups adjacent to each other bond to each other to form a substituted or unsubstituted C6 to C60 aromatic hydrocarbon ring or a substituted or unsubstituted C2 to C60 heteroring.
5. The organic light emitting device of claim 4 , wherein Chemical Formula 15 is selected from among the following structural formulae:
in the structures,
R21 to R25 have the same definitions as in Chemical Formula 15.
6. The organic light emitting device of claim 1 , wherein Chemical Formula 24 is represented by any one of the following Chemical Formulae 25 to 28:
in Chemical Formulae 25 to 28,
R11 to R14, L1, Ar1, Ar2, m, n, p and q have the same definitions as in Chemical Formula 24.
7. The organic light emitting device of claim 1 , wherein Art of Chemical Formula 24 is a C6 to C20 monocyclic or polycyclic aryl group unsubstituted or substituted with a C1 to C10 alkyl group; or a polycyclic C2 to C20 heteroaryl group comprising at least one of S and O; and
Ar2 of Chemical Formula 24 is a C6 to C20 aryl group.
8. The organic light emitting device of claim 1 , wherein Chemical Formula 1 is represented by any one of compounds of the following Group 1 and Group 2:
[Group 1]
9. The organic light emitting device of claim 1 , wherein Chemical Formula 24 is represented by any one of the following compounds:
10. The organic light emitting device of claim 1 , wherein the organic material layer comprises at least one of a hole blocking layer, an electron injection layer and an electron transfer layer, and at least one of the hole blocking layer, the electron injection layer and the electron transfer layer comprises the heterocyclic compound represented by Chemical Formula 1 and the heterocyclic compound represented by Chemical Formula 24.
11. The organic light emitting device of claim 1 , wherein the organic material layer comprises a light emitting layer, the light emitting layer comprises a host material, and the host material comprises the heterocyclic compound represented by Chemical Formula 1 and the heterocyclic compound represented by Chemical Formula 24.
12. The organic light emitting device of claim 1 , wherein the organic material layer comprises a light emitting layer, the light emitting layer comprises a host material and a dopant material, and the host material comprises the heterocyclic compound represented by Chemical Formula 1 and the heterocyclic compound represented by Chemical Formula 24; and
the dopant material is included in greater than or equal to 1 parts by weight and less than or equal to 15 parts by weight with respect to 100 parts by weight of the host material.
13. The organic light emitting device of claim 1 , 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.
14. A composition for an organic material layer of an organic light emitting device, the composition comprising:
a heterocyclic compound represented by the following Chemical Formula 1; and
a compound represented by the following Chemical Formula 24:
in Chemical Formulae 1 and 24,
N-Het is a monocyclic or polycyclic heterocyclic group substituted or unsubstituted and comprising one or more Ns;
L and L1 are a direct bond; a substituted or unsubstituted C6 to C60 arylene group; or a substituted or unsubstituted C2 to C60 heteroarylene group, a is an integer of 1 to 3, and when a is 2 or greater, Ls are the same as or different from each other;
R1 to R14 are the same as or different from each other, and each independently selected from the group consisting of hydrogen; deuterium; halogen; a cyano group; a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C2 to C60 alkenyl group; a substituted or unsubstituted C2 to C60 alkynyl group; a substituted or unsubstituted C2 to C60 alkoxy group; a substituted or unsubstituted C3 to C60 cycloalkyl group; a substituted or unsubstituted C2 to C60 heterocycloalkyl group; a substituted or unsubstituted C6 to C60 aryl group; a substituted or unsubstituted C2 to C60 heteroaryl group; a substituted or unsubstituted phosphine oxide group; and a substituted or unsubstituted amine group, or two or more groups adjacent to each other bond to each other to form a substituted or unsubstituted C6 to C60 aromatic hydrocarbon ring or a substituted or unsubstituted C2 to C60 heteroring;
b and c are each an integer of 1 to 3;
when b is 2 or greater, R9s are the same as or different from each other, and when c is 2 or greater, R10s are the same as or different from each other;
m, p and q are an integer of 0 to 4;
n is an integer of 0 to 2;
when m is 2 or greater, R11s are the same as or different from each other, when n is an integer of 2, R12s are the same as or different from each other, when p is 2 or greater, R13s are the same as or different from each other, and when q is 2 or greater, R14s are the same as or different from each other;
Ar1 is a substituted or unsubstituted C6 to C60 aryl group; or a C2 to C60 heteroaryl group substituted or unsubstituted and comprising at least one of S and O; and
Ar2 is a substituted or unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 to C60 heteroaryl group.
15. The composition for an organic material layer of an organic light emitting device of claim 14 , wherein, in the composition, the heterocyclic compound represented by Chemical Formula 1: the heterocyclic compound represented by Chemical Formula 24 have a weight ratio of 1:10 to 10:1.
16. A method for manufacturing an organic light emitting device, the method comprising:
preparing a substrate;
forming a first electrode on the substrate;
forming one or more organic material layers on the first electrode; and
forming a second electrode on the organic material layer,
wherein the forming of organic material layers comprises forming one or more organic material layers using the composition for an organic material layer of claim 14 .
17. The method for manufacturing an organic light emitting device of claim 16 , wherein the forming of organic material layers is forming using a method of thermal vacuum deposition after pre-mixing the heterocyclic compound of Chemical Formula 1 and the heterocyclic compound of Chemical Formula 24.