Space-through charge transfer compound, and organic light emitting diode and display device using the same

Patent metadata

Field	Value
Publication number	US-10141515-B2
Application number	US-201514885707-A
Country	US
Kind code	B2
Filing date	Oct 16, 2015
Priority date	Oct 17, 2014
Publication date	Nov 27, 2018
Grant date	Nov 27, 2018

Abstract

Discussed is a space-through charge transfer compound including a naphthalene core; an electron donor moiety selected from carbazole and phenylcarbazole; and an electron acceptor moiety selected from pyridine, diazine, triazole, and phenyl benzodiazole, wherein the electron donor moiety and the electron acceptor moiety are combined to first and eighth positions of the naphthalene core with a benzene linker, respectively.

First claim

What is claimed is:

1. A space-through charge transfer compound, comprising:
a naphthalene core;
an electron donor moiety selected from the group consisting of carbazole and phenylcarbazole; and
an electron acceptor moiety selected from the group consisting of pyridine, diazine, triazole, and phenyl benzodiazole,
wherein the electron donor moiety and the electron acceptor moiety are combined to first and eighth positions of the naphthalene core with a benzene linker, respectively.

2. A space-through charge transfer compound of Formula 1:

wherein D is selected from Formula 2, and A is selected from Formula 3:

wherein R in the Formula 2 is selected from the group consisting of hydrogen, C1 alkyl through C8 alkyl, and C6 aryl through C20 aryl, and wherein X, Y, Z in the Formula 3 are independently selected from the group consisting of carbon and nitrogen, and at least one selected from X and Y is nitrogen.

3. The space-through charge transfer compound according to claim 2 , wherein a difference between a singlet energy of the space-through charge transfer compound and a triplet energy of the space-through charge transfer compound is less than 0.3 eV.

4. 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 space-through charge transfer compound,
wherein the space-through charge transfer compound includes a naphthalene core, an electron donor moiety selected from the group consisting of carbazole and phenylcarbazole, and an electron acceptor moiety selected from the group consisting of pyridine, diazine, triazole, and phenyl benzodiazole, and
wherein the electron donor moiety and the electron acceptor moiety are combined to first and eighth positions of the naphthalene core with a benzene linker, respectively.

5. The organic light emitting diode according to claim 4 , 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 space-through charge transfer compound.

6. The organic light emitting diode according to claim 4 , wherein a difference between a singlet energy of the space-through charge transfer compound and a triplet energy of the space-through charge transfer compound is less than 0.3 eV.

7. The organic light emitting diode according to claim 4 , wherein the organic emitting layer further includes a host, and the space-through charge transfer compound is used as a dopant.

8. The organic light emitting diode according to claim 7 , wherein a difference between a highest occupied molecular orbital (HOMO) of the host and a 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.

9. The organic light emitting diode according to claim 4 , wherein the organic emitting layer further includes a dopant, and the space-through charge transfer compound is used as a host.

10. The organic light emitting diode according to claim 4 , wherein the organic emitting layer further includes a host and a first dopant, and the space-through charge transfer 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.

11. 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 space-through charge transfer compound of Formula 1:

wherein D is selected from Formula 2, and A is selected from Formula 3:

wherein R in the Formula 2 is selected from the group consisting of hydrogen, C1 alkyl through C8 alkyl, and C6 aryl through C20 aryl, and wherein X, Y, Z in the Formula 3 are independently selected from the group consisting of carbon and nitrogen, and at least one selected from X and Y is nitrogen.

12. The organic light emitting diode according to claim 11 , 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 space-through charge transfer compound.

13. The organic light emitting diode according to claim 11 , wherein a difference between a singlet energy of the space-through charge transfer compound and a triplet energy of the space-through charge transfer compound is less than 0.3 eV.

14. The organic light emitting diode according to claim 11 , wherein the organic emitting layer further includes a host, and the space-through charge transfer compound is used as a dopant.

15. The organic light emitting diode according to claim 14 , wherein a difference between a highest occupied molecular orbital (HOMO) of the host and a 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.

16. The organic light emitting diode according to claim 11 , wherein the organic emitting layer further includes a dopant, and the space-through charge transfer compound is used as a host.

17. The organic light emitting diode according to claim 11 , wherein the organic emitting layer further includes a host and a first dopant, and the space-through charge transfer 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.

18. 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 space-through charge transfer compound;
an encapsulation film on the organic light emitting diode; and
a cover window on the encapsulation film,
wherein the space-through charge transfer compound includes a naphthalene core, an electron donor moiety selected from the group consisting of carbazole and phenylcarbazole, and an electron acceptor moiety selected from the group consisting of pyridine, diazine, triazole, and phenyl benzodiazole, and
wherein the electron donor moiety and the electron acceptor moiety are combined to first and eighth positions of the naphthalene core with a benzene linker, respectively.

19. A display device, comprising:
a substrate;
an organic light emitting diode on the substrate and including a first electrode, a second electrode facing the

Assignees

• Lg Display Co Ltd

Inventors

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

Classifications

• C09K2211/1011

  Condensed systems · CPC title

• C07D401/10

  linked by a carbon chain containing aromatic rings · CPC title

• H01L51/005

  Electricity · mapped topic

• H01L27/3258

  Electricity · mapped topic

• H01L2251/552

  Electricity · mapped topic