IP Library Granted Patent US 11,387,418
Granted Patent B2
US 11,387,418 · App. 16/496,870 · Granted Jul 12, 2022

Organic light emitting element and composition for organic material layer in organic light emitting element

Inventors: Young Seok No (Osan-si, KR); Jiyoon Byun (Osan-si, KR); Dongjun Kim (Yongin-si, KR)
Assignee: LT MATERIALS CO., LTD.
H01L51/0072C07D209/86C07D405/14C07D409/14C07D495/04H01L51/0067H01L51/0073H01L51/0074H01L51/001H01L51/5016H01L51/5024H01L51/5072H01L51/5092H01L51/5096H01L51/56H01L2251/558
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Quick Facts
Patent No.
US 11,387,418
App. No.
16/496,870
Granted
Jul 12, 2022
Kind
B2
Abstract

The present specification relates to 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 Chemical Formula 1 and a heterocyclic compound represented by Chemical Formula 2 at the same time, and a composition for an organic material layer of an organic light emitting device.

Claims (48)

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 2 at the same time:

in Chemical Formulae 1 and 2,

N-Het is a monocyclic or multicyclic heterocyclic group substituted or unsubstituted, and comprising one or more Ns;

L is a direct bond; a substituted or unsubstituted arylene group; or a substituted or unsubstituted 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;

Ra and Rb are the same as or different from each other, and each independently a substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group; and

R9 and R10 are the same as or different from each other, and each independently selected from the group consisting of hydrogen and deuterium;

R1 to R8, Rc and Rd 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 alkyl group; a substituted or unsubstituted alkenyl group; a substituted or unsubstituted alkynyl group; a substituted or unsubstituted alkoxy group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted heterocycloalkyl group; a substituted or unsubstituted aryl group; a substituted or unsubstituted heteroaryl group; a substituted or unsubstituted silyl 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 aliphatic or aromatic hydrocarbon ring or heteroring, b and c are each an integer of 1 to 3, and 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, r and s are each an integer of 0 to 7, and when r is 2 or greater, Rcs are the same as or different from each other and when s is 2 or greater, Rds are the same as or different from each other.

2. The organic light emitting device of claim 1 , wherein Chemical Formula 1 is represented by one of the following Chemical Formulae 3 to 6:

in Chemical Formulae 3 to 6, substituents 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 7 to 9:

in Chemical Formulae 7 to 9, R1 to R10, L, a, b and c have the same definitions as in Chemical Formula 1;

X1 is CR11 or N, X2 is CR12 or N, X3 is CR13 or N, X4 is CR14 or N, and X5 is CR15 or N; one or more of X1 to X5 are N, and

R11 to R15 and R17 to R22 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 alkyl group; a substituted or unsubstituted alkenyl group; a substituted or unsubstituted alkynyl group; a substituted or unsubstituted alkoxy group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted heterocycloalkyl group; a substituted or unsubstituted aryl group; a substituted or unsubstituted 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 aliphatic or aromatic hydrocarbon ring or heteroring.

4. The organic light emitting device of claim 3 , wherein

is represented by one of the following Chemical Formulae 10 to 12:

in Chemical Formula 10, one or more of X1, X3 and X5 are N, and the rest have the same definitions as in Chemical Formula 7;

in Chemical Formula 11, one or more of X1, X2 and X5 are N, and the rest have the same definitions as in Chemical Formula 7;

in Chemical Formula 12, one or more of X1 to X3 are N, and the rest have the same definitions as in Chemical Formula 7; and

R12, R14 and R23 to R26 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 alkyl group; a substituted or unsubstituted alkenyl group; a substituted or unsubstituted alkynyl group; a substituted or unsubstituted alkoxy group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted heterocycloalkyl group; a substituted or unsubstituted aryl group; a substituted or unsubstituted 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 aliphatic or aromatic hydrocarbon ring or heteroring.

5. The organic light emitting device of claim 4 , wherein Chemical Formula 10 is selected from among the following structural formulae:

in the structural formulae, R11 to R15 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 alkyl group; a substituted or unsubstituted alkenyl group; a substituted or unsubstituted alkynyl group; a substituted or unsubstituted alkoxy group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted heterocycloalkyl group; a substituted or unsubstituted aryl group; a substituted or unsubstituted 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 aliphatic or aromatic hydrocarbon ring or heteroring.

6. The organic light emitting device of claim 1 , wherein Rc and Rd of Chemical Formula 2 are hydrogen.

7. The organic light emitting device of claim 1 , wherein Ra and Rb of Chemical Formula 2 are the same as or different from each other, and each independently a substituted or unsubstituted C6 to C40 aryl group.

8. The organic light emitting device of claim 1 , wherein Chemical Formula 1 is represented by any one of the following compounds:

9. The organic light emitting device of claim 1 , wherein Chemical Formula 2 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 layer of a hole blocking layer, an electron injection layer and an electron transfer layer, and at least one layer 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 2 at the same time.

11. The organic light emitting device of claim 1 , wherein the organic material layer comprises a light emitting layer, and the light emitting layer comprises the heterocyclic compound represented by Chemical Formula 1 and the heterocyclic compound represented by Chemical Formula 2 at the same time.

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 the host material comprises the heterocyclic compound represented by Chemical Formula 1 and the heterocyclic compound represented by Chemical Formula 2 at the same time.

13. The organic light emitting device of claim 1 , 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.

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 heterocyclic compound represented by the following Chemical Formula 2 at the same time:

wherein, in Chemical Formulae 1 and 2,

N-Het is a monocyclic or multicyclic heterocyclic group substituted or unsubstituted, and comprising one or more Ns;

L is a direct bond; a substituted or unsubstituted arylene group; or a substituted or unsubstituted 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;

Ra and Rb are the same as or different from each other, and each independently a substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group; and

R9 and R10 are the same as or different from each other, and each independently selected from the group consisting of hydrogen; and deuterium;

R1 to R8, Rc and Rd 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 alkyl group; a substituted or unsubstituted alkenyl group; a substituted or unsubstituted alkynyl group; a substituted or unsubstituted alkoxy group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted heterocycloalkyl group; a substituted or unsubstituted aryl group; a substituted or unsubstituted heteroaryl group; a substituted or unsubstituted silyl 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 aliphatic or aromatic hydrocarbon ring or heteroring, b and c are each an integer of 1 to 3, and 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, r and s are each an integer of 0 to 7, and when r is 2 or greater, Rcs are the same as or different from each other and when s is 2 or greater, Rds are the same as or different from each other.

15. The composition for an organic material layer of an organic light emitting device of claim 14 , wherein a weight ratio of the heterocyclic compound represented by Chemical Formula 1: the heterocyclic compound represented by Chemical Formula 2 in the composition is from 1:10 to 10:1.

16. A method for manufacturing an organic light emitting device 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 an organic material layer 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 an organic material layer is forming using a thermal vacuum deposition method after pre-mixing the heterocyclic compound of Chemical Formula 1 and the heterocyclic compound of Chemical Formula 2.

Assignments (2)
CHANGE OF NAME Recorded Feb 13, 2020
From: HEESUNG MATERIAL LTD.
To: LT MATERIALS CO., LTD.
Reel/Frame 051926/0419 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Sep 24, 2019
From: NO, YOUNG SEOK; BYUN, JIYOON; KIM, DONGJUN
To: HEESUNG MATERIAL LTD.
Reel/Frame 050477/0058 →
Priority Claims (3)
KR 10-2017-0037976 · Mar 24, 2017 · national
KR 10-2018-0018780 · Feb 14, 2018 · national
KR 10-2018-0018784 · Feb 14, 2018 · national
Continuity (1)
Related Publication 20200119285A1 · Apr 16, 2020
Cited By (1)
US 12,534,464