Delayed fluorescence compound, and organic light emitting diode and display device using the same

Patent metadata

Field	Value
Publication number	US-9711735-B2
Application number	US-201514885761-A
Country	US
Kind code	B2
Filing date	Oct 16, 2015
Priority date	Oct 17, 2014
Publication date	Jul 18, 2017
Grant date	Jul 18, 2017

Abstract

Discussed is a delayed fluorescence compound of Formula 1:

wherein n is 1 or 0, and A is selected from Formula 2:

wherein D is selected from Formula 3:

and each of “L 1 ” and “L 2 ” is independently selected from Formula 4:

wherein R1 in the Formula 2 is selected from hydrogen or phenyl, and each of X, Y, and Z is independently selected from carbon and nitrogen, and wherein at least two selected from X, Y, and Z are nitrogen, and R2 in the Formula 4 is selected from one of hydrogen and C1 alkyl through C10 alkyl.

First claim

What is claimed is:

1. A delayed fluorescence compound of Formula 1:

wherein n is 1 or 0, and A is selected from Formula 2, wherein D is selected from Formula 3, and each of L 1 and L 2 is independently selected from Formula 4:

wherein R1 in the Formula 2 is selected from hydrogen or phenyl, and each of X, Y, and Z is independently selected from the group consisting of carbon and nitrogen, and wherein at least two selected from X, Y, and Z are nitrogen, and R2 in the Formula 4 is selected from the group consisting of hydrogen and C1 alkyl through C10 alkyl.

2. The delayed fluorescence compound according to claim 1 , wherein a difference between a singlet energy of the delayed fluorescence compound and a triplet energy of the delayed fluorescence compound is less than 0.3 eV.

3. An organic light emitting diode, comprising:
a first electrode;
a second electrode facing the first electrode; and
an organic emitting layer between the first electrode and the second electrode, the organic emitting layer including a delayed fluorescence compound of Formula 1:

wherein n is 1 or 0, and A is selected from Formula 2, wherein D is selected from Formula 3, and each of L 1 and L 2 is independently selected from Formula 4:

wherein R1 in the Formula 2 is selected from hydrogen or phenyl, and each of X, Y, and Z is independently selected from the group consisting of carbon and nitrogen, and wherein at least two selected from X, Y, and Z are nitrogen, and R2 in the Formula 4 is selected from the group consisting of hydrogen and C1 alkyl through C10 alkyl.

4. The organic light emitting diode according to claim 3 , wherein the organic emitting layer includes a hole injection layer (HIL), a hole transporting layer (HTL), an emitting material layer (EML), an electron transporting layer (ETL), and an electron injection layer (EIL), and
wherein at least one from selected from the group consisting of the HIL, the HTL, the EML, the ETL and the EIL includes the delayed fluorescence compound.

5. The organic light emitting diode according to claim 3 , wherein a difference between a singlet energy of the delayed fluorescence compound and a triplet energy of the delayed fluorescence compound is less than 0.3 eV.

6. The organic light emitting diode according to claim 3 , wherein the organic emitting layer further includes a host, and the delayed fluorescence compound is used as a dopant.

7. The organic light emitting diode according to claim 6 , wherein a difference between a HOMO of the host and a highest occupied molecular orbital (HOMO) of the dopant or a difference between a lowest unoccupied molecular orbital (LUMO) of the host and a LUMO of the dopant is less than 0.5 eV.

8. The organic light emitting diode according to claim 3 , wherein the organic emitting layer further includes a dopant, and the delayed fluorescence compound is used as a host.

9. The organic light emitting diode according to claim 3 , wherein the organic emitting layer further includes a host and a first dopant, and the delayed fluorescence compound is used as a second dopant, and
wherein a triplet energy of the second dopant is smaller than a triplet energy of the host and larger than a triplet energy of the first dopant.

10. A display device, comprising:
a substrate;
an organic light emitting diode on the substrate and including a first electrode, a second electrode facing the first electrode and an organic emitting layer between the first electrode and the second electrode, the organic emitting layer including a delayed fluorescence compound of Formula 1;
an encapsulation film on the organic light emitting diode; and
a cover window on the encapsulation film,

wherein n is 1 or 0, and A is selected from Formula 2, wherein D is selected from Formula 3, and each of L 1 and L 2 is independently selected from Formula 4:

wherein R1 in the Formula 2 is selected from hydrogen or phenyl, and each of X, Y, and Z is independently selected from carbon and nitrogen, and wherein at least two selected from X, Y, and Z are nitrogen, and R2 in the Formula 4 is selected from the group consisting of hydrogen and C1 alkyl through C10 alkyl.

Assignees

• Lg Display Co Ltd

Inventors

• Yang Joong-Hwan
• Yoon Kyung-Jin
• Noh Hyo-Jin
• Yoon Dae-Wi
• Shin In-Ae
• Kim Jun-Yun

Classifications

• C09K11/02

  Use of particular materials as binders, particle coatings or suspension media therefor · CPC title

• C09K11/06 Primary

  containing organic luminescent materials · CPC title

• C09K2211/1044

  containing two nitrogen atoms as heteroatoms · CPC title

• H01L51/5012

  Electricity · mapped topic

• C09K2211/1059

  containing three nitrogen atoms as heteroatoms · CPC title