Electroluminescent compound and electroluminescent device including the same

Patent metadata

Field	Value
Publication number	US-11469378-B2
Application number	US-201916436603-A
Country	US
Kind code	B2
Filing date	Jun 10, 2019
Priority date	Jun 11, 2018
Publication date	Oct 11, 2022
Grant date	Oct 11, 2022

Abstract

The present invention provides an electroluminescent compound of one of following formulas Formula 1 and Formula 2. Another aspect of the invention is an electroluminescent device including a first electrode; a second electrode facing the first electrode; and at least one organic material layer between the first and second electrodes, wherein one or more of the at least one organic material layer includes the electroluminescent compound.

First claim

What is claimed is:

1. An electroluminescent device, comprising:
a first electrode;
a second electrode facing the first electrode;
at least one organic material layer between the first and second electrodes; and
a light-efficiency enhancing layer on a side of one of the first electrode and the second electrode,
wherein the light-efficiency enhancing layer is positioned to be opposite to the organic material layer,
wherein the light-efficiency enhancing layer includes an electroluminescent compound of Formula 1;
wherein one or more of the at least one organic material layer includes the electroluminescent compound of Formula 1, and
wherein the electroluminescent compound of Formula 1 is:

wherein each of X 1 to X 4 is independently N or CR′,
wherein each of R and R′ is independently selected from the group consisting of hydrogen, deuterium, cyano group, hydroxyl group, halogen, a substituted or non-substituted C1 to C10 alkyl group, a substituted or non-substituted C6 to C20 aryl group and a substituted or non-substituted C3 to C30 heteroaryl group,
wherein L 1 is selected from a single bond, a substituted or non-substituted C6 to C20 arylene group and a substituted or non-substituted C3 to C30 heteroarylene group, and
wherein Ar 1 is a substituted or non-substituted C6 to C20 aryl group, and Ar 2 is a substituted or non-substituted C3 to C30 heteroaryl group.

2. The electroluminescent device according to claim 1 , wherein L 1 is selected from Formula 3a and 3b:

wherein each of X 5 to X 7 is independently N or CR 1 ,
wherein each of Y 1 and Y 2 is independently selected from a single bond, O, S, Se, Si(R 2 )(R 4 ), and C(R 3 )(R 5 ), and
wherein each of R 1 , R 2 , R 3 , R 4 and R 5 is independently selected from the group consisting of hydrogen, deuterium, cyano group, hydroxyl group, halogen, a substituted or non-substituted C1 to C10 alkyl group, a substituted or non-substituted C6 to C20 aryl group and substituted or a non-substituted C3 to C30 heteroaryl group.

3. The electroluminescent device according to claim 1 , wherein when substituted, each substituent of L 1 , Ar 1 and Ar 2 is independently selected from the group consisting of deuterium, cyano group, halogen, amino group, hydroxyl group, nitro group, a substituted or non-substituted C1 to C10 alkyl group, a substituted or non-substituted C1 to C10 halogenated alkyl group, a substituted or non-substituted C6 to C20 aryl group, a substituted or non-substituted C3 to C30 heteroaryl group, a substituted or non-substituted C1 to C10 alkoxy group, a substituted or non-substituted C1 to C10 alkylsilyl group and a substituted or non-substituted C6 to C20 arylsilyl group.

4. The electroluminescent device according to claim 1 , wherein the electroluminescent compound is selected from Formula 5:

5. The electroluminescent device according to claim 1 , wherein the at least one organic material layer includes at least one of an electron injection layer, an electron transporting layer, a hole injection layer, a hole transporting layer, an electron blocking layer, a hole blocking layer and an emitting material layer.

6. The electroluminescent device according to claim 5 , wherein the hole transporting layer includes the electroluminescent compound.

7. The electroluminescent device according claim 1 , wherein the light-efficiency enhancing layer is formed on at least one of a lower surface of the first electrode and an upper surface of the second electrode.

8. The electroluminescent device according to claim 1 , wherein L 1 is selected from Formula 3a and 3b:

wherein each of X 5 to X 7 is independently N or CR 1 ,
wherein each of Y 1 and Y 2 is independently selected from a single bond, O, S, Se, Si(R 2 )(R 4 ), and C(R 3 )(R 5 ), and
wherein each of R 1 , R 2 , R 3 , R 4 and R 5 is independently selected from the group consisting of hydrogen, deuterium, cyano group, hydroxyl group, halogen, a substituted or non-substituted C1 to C10 alkyl group, a substituted or non-substituted C6 to C20 aryl group and a substituted or non-substituted C3 to C30 heteroaryl group.

9. The electroluminescent device of claim 1 , wherein R and R′ are hydrogen.

10. An electroluminescent compound selected from Formula 5:

11. An electroluminescent compound selected from Formula 5:

12. An electroluminescent device, comprising:
a first electrode;
a second electrode facing the first electrode;
at least one organic material layer between the first and second electrodes and including an electron injection layer, an electron transporting layer, a hole injection layer, a hole transporting layer, an electron blocking layer, a hole blocking layer and an emitting material layer, and
a light-efficiency enhancing layer on a side of one of the first electrode and the second electrode, the light-efficiency enhancing layer is positioned to be opposite to the organic material layer,
wherein one or more of the hole transporting layer and light-efficiency enhancing layer includes an electroluminescent compound of Formula 2:

wherein each of X 1 to X 4 is independently N or CR′,
wherein each of R and R′ is independently selected from the group consisting of hydrogen, deuterium, cyano group, hydroxyl group, halogen, a substituted or non-substituted C1 to C10 alkyl group, a substituted or non-substituted C6 to C20 aryl group and a substituted or non-substituted C3 to C30 heteroaryl group,
wherein L 2 is selected from a single bond, a substituted or non-substituted C6 to C20 arylene group and a substituted or non-substituted C3 to C30 heteroarylene group,
wherein Ar is selected from the group consisting of a sub

Assignees

• Lg Display Co Ltd
• Pnh Tech

Inventors

• Yoo Seon-Keun
• Park Hee-Jun
• Seo Jeong-Dae
• Hyun Seo-Yong
• Kim Ha-Yeon
• Yoon Seok-Keun
• Kim Sun-Gi
• Lee In-Ho

Classifications

• C09K2211/1096

  containing other heteroatoms · CPC title

• C09K2211/1092

  containing sulfur as the only heteroatom · CPC title

• C09K2211/1088

  containing oxygen as the only heteroatom · CPC title

• C09K2211/1077

  with oxygen · CPC title

• C09K2211/1074

  containing more than three nitrogen atoms as heteroatoms · CPC title