IP Library Granted Patent US 10,519,166
Granted Patent B2
US 10,519,166 · App. 15/562,581 · Granted Dec 31, 2019

Heterocyclic compound and organic light emitting device comprising the same

Inventors: Wanpyo Hong (Daejeon, KR); Dongheon Kim (Daejeon, KR); Hyoungcheul Kim (Daejeon, KR); Yongbum Cha (Daejeon, KR); Yun Hwan Kim (Daejeon, KR)
Assignee: LG Chem, Ltd.
C07D495/14C07D333/76C07D333/78C07D409/14C07D495/04C07D495/22C09K11/06H01L51/0074H01L51/0094H01L51/5012C09K2211/1092H01L51/5088
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Quick Facts
Patent No.
US 10,519,166
App. No.
15/562,581
Granted
Dec 31, 2019
Kind
B2
Abstract

The present specification provides a heterocyclic compound and an organic light emitting device including the same.

Claims (47)

1. A compound represented by the following Chemical Formula 1:

in Chemical Formula 1,

Z is a thiophene ring or a thienothiophene ring,

Ar 1 is

Ar 2 is

X 1 and X 2 are the same as or different from each other, and are each independently any one selected from the following (a) to (g),

Y 1 to Y 4 are the same as or different from each other, and are each independently N or CR 5 ,

R 1 to R 5 are the same as or different from each other, and are each independently hydrogen; deuterium; a halogen group; a nitrile group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted haloalkyl group; a substituted or unsubstituted alkoxy group; a substituted or unsubstituted haloalkoxy group; a substituted or unsubstituted aryl group; a substituted or unsubstituted haloaryl group; a substituted or unsubstituted silyl group; or a substituted or unsubstituted hetero ring,

when Z is a thiophene ring, all of Y 1 to Y 4 are CH, and X 1 and X 2 are the same as or different from each other and are each any one of (a) to (f), then at least one of R 1 to R 4 is a halogen group; a nitrile group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted haloalkyl group; a substituted or unsubstituted alkoxy group; a substituted or unsubstituted haloalkoxy group; a substituted or unsubstituted aryl group; a substituted or unsubstituted haloaryl group; a substituted or unsubstituted silyl group; or a substituted or unsubstituted heterocyclic group, or adjacent groups of R 1 to R 5 combine with each other to form a substituted or unsubstituted aromatic hydrocarbon ring or a substituted or unsubstituted hetero ring, and

R 21 to R 24 are the same as or different from each other, and are each independently hydrogen; deuterium; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heterocyclic group.

2. The compound of claim 1 , wherein the compound of Chemical Formula 1 is represented by any one of the following Chemical Formulae 2 to 4:

in Chemical Formulae 2 to 4,

definitions of X 1 , X 2 , Y 1 to Y 4 , R 1 to R 5 , and R 21 to R 24 are the same as those in Chemical Formula 1.

3. The compound of claim 1 , wherein the compound of Chemical Formula 1 is represented by any one of the following Chemical Formulae 5 to 8:

in Chemical Formulae 5 to 8,

definitions of X 1 , X 2 , Y 1 to Y 4 , R 1 to R 5 , and R 21 to R 24 are the same as those in Chemical Formula 1.

4. The compound of claim 1 , wherein the compound of Chemical Formula 1 is represented by any one of the following Chemical Formulae 9 to 11:

in Chemical Formulae 9 to 11,

definitions of X 1 , X 2 , Y 1 to Y 4 , R 1 to R 5 , and R 21 to R 24 are the same as those in Chemical Formula 1.

5. The compound of claim 1 , wherein the compound of Chemical Formula 1 is any one selected from the following compounds:

6. An organic light emitting device comprising:

a first electrode;

a second electrode; and

one or more organic material layers disposed between the first electrode and the second electrode, wherein one or more layers of the organic material layers comprise the compound of claim 1 .

7. The organic light emitting device of claim 6 , wherein the organic material layer comprises one or more layers of an electron transport layer, an electron injection layer, and a layer which transports and injects electrons simultaneously, and one or more layers of the layers comprise the compound.

8. The organic light emitting device of claim 6 , wherein the organic material layer comprises a light emitting layer, and the light emitting layer comprises the compound as a host of the light emitting layer.

9. The organic light emitting device of claim 6 , wherein the organic material layer comprises one or more layers of a hole injection layer, an electron blocking layer, a hole transport layer, and a layer which injects and transports holes simultaneously, and one or more layers of the layers comprise the compound.

10. The organic light emitting device of claim 6 , wherein the organic material layer comprises a hole injection layer, and the hole injection layer comprises the compound represented by Chemical Formula 1 as a dopant.

11. The organic light emitting device of claim 6 , wherein the organic material layer comprises the compound as a host, and comprises another organic compound, a metal, or a metal compound as a dopant.

12. The organic light emitting device of claim 6 , wherein the organic material layer comprises two or more light emitting layers, and comprises a charge generation layer provided between the two light emitting layers, and the charge generation layer comprises the compound.

13. The organic light emitting device of claim 6 , wherein the organic material layer comprises a compound represented by the following Chemical Formula 1-A:

in Chemical Formula 1-A,

n1 is an integer of 1 or more,

Ar7 is a substituted or unsubstituted monovalent or more benzofluorene group; a substituted or unsubstituted monovalent or more fluoranthene group; a substituted or unsubstituted monovalent or more pyrene group; or a substituted or unsubstituted monovalent or more chrysene group,

L4 is a direct bond; a substituted or unsubstituted arylene group; or a substituted or unsubstituted heteroarylene group,

Ar8 and Ar9 are the same as or different from each other, and are each independently a substituted or unsubstituted aryl group; a substituted or unsubstituted silyl group; a substituted or unsubstituted germanium group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted arylalkyl group; or a substituted or unsubstituted heteroaryl group, or optionally combine with each other to form a substituted or unsubstituted ring, and

when n1 is 2 or more, two or more structures in the parenthesis are the same as or different from each other.

14. The organic light emitting device of claim 13 , wherein L4 is a direct bond, Ar7 is a divalent pyrene group, Ar8 and Ar9 are the same as or different from each other, and are each independently an aryl group having 6 to 30 carbon atoms, which is unsubstituted or substituted with an alkyl group having 1 to 30 carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms, and n1 is 2.

15. The organic light emitting device of claim 13 , wherein the organic material layer comprises a compound represented by the following Chemical Formula 2-A:

in Chemical Formula 2-A,

Ar4 and Ar5 are the same as or different from each other, and are each independently a substituted or unsubstituted monocyclic aryl group; or a substituted or unsubstituted polycyclic aryl group, and

G1 to G8 are the same as or different from each other, and are each independently hydrogen; a substituted or unsubstituted alkyl group; a substituted or unsubstituted monocyclic aryl group; or a substituted or unsubstituted polycyclic aryl group.

16. The organic light emitting device of claim 6 , wherein the organic material layer comprises a compound represented by the following Chemical Formula 2-A:

in Chemical Formula 2-A,

Ar4 and Ar5 are the same as or different from each other, and are each independently a substituted or unsubstituted monocyclic aryl group; or a substituted or unsubstituted polycyclic aryl group, and

G1 to G8 are the same as or different from each other, and are each independently hydrogen; a substituted or unsubstituted alkyl group; a substituted or unsubstituted monocyclic aryl group; or a substituted or unsubstituted polycyclic aryl group.

17. The light emitting device of claim 16 , wherein Ar4 and Ar5 are a 2-naphthyl group, and G1 to G8 are hydrogen or a substituted or unsubstituted alkyl group.

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Oct 2, 2017
From: HONG, WANPYO; KIM, DONGHEON; KIM, HYOUNGCHEUL; CHA, YONGBUM; KIM, YUN HWAN
To: LG CHEM, LTD.
Reel/Frame 043753/0984 →
Priority Claims (1)
KR 10-2015-0148680 · Oct 26, 2015 · national
Continuity (1)
Related Publication 20180086775A1 · Mar 29, 2018