Organic electroluminescence device and monoamine compound for organic electroluminescence device

Patent metadata

Field	Value
Publication number	US-11038111-B2
Application number	US-201816200412-A
Country	US
Kind code	B2
Filing date	Nov 26, 2018
Priority date	Nov 28, 2017
Publication date	Jun 15, 2021
Grant date	Jun 15, 2021

Abstract

An organic electroluminescence device includes a first electrode and a second electrode which are positioned facing each other, and at least one organic layer between the first electrode and the second electrode, wherein the at least one organic layer includes a monoamine compound which is represented by Formula 1 and includes at least one adamantyl group as a substituent, thereby achieving improved device efficiency:

First claim

What is claimed is:

1. An organic electroluminescence device, comprising:
a first electrode;
a second electrode on the first electrode; and
a plurality of organic layers between the first electrode and the second electrode,
wherein at least one organic layer among the plurality of organic layers comprises a monoamine compound represented by the following Formula 1:

wherein, in Formula 1,
at least one selected from Ar 1 , Ar 2 and Ar 3 is represented by the following Formula 2, and the remaining ones of Ar 1 , Ar 2 and Ar 3 are each independently a substituted or unsubstituted aryl group having 6 to 30 carbon atoms for forming a ring, or a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms for forming a ring:

in Formula 2,
R 1 to R 3 are each independently a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted silyl group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms for forming a ring, or a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms for forming a ring,
“m” is 0 or 1,
“a”, “b”, “x” and “y” are each independently an integer of 0 to 4,
wherein if “m” is 0, “x” is an integer of 1 or more, and if “m” is 1, “x+y” is an integer of 1 or more, and
Ad is represented by the following Formula 3:

in Formula 3,
R 4 is a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted silyl group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms for forming a ring, or a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms for forming a ring, and
“n” is an integer of 0 to 15.

2. The organic electroluminescence device of claim 1 , wherein the plurality of organic layers comprise:
an emission layer; and
a hole transport region between the first electrode and the emission layer,
wherein the hole transport region comprises the monoamine compound represented by Formula 1.

3. The organic electroluminescence device of claim 1 , wherein the plurality of organic layers comprise:
an emission layer;
a hole injection layer between the first electrode and the emission layer; and
a hole transport layer between the hole injection layer and the emission layer,
wherein the hole transport layer comprises the monoamine compound represented by Formula 1.

4. The organic electroluminescence device of claim 1 , wherein Formula 3 is represented by the following Formula 3-1 or Formula 3-2:

wherein, in Formula 3-1 and Formula 3-2, R 4 and “n” are the same as defined in Formula 3.

5. The organic electroluminescence device of claim 1 , wherein Formula 1 is represented by the following Formula 1-A or Formula 1-B:

wherein, in Formula 1-B,
“m1” and “m2” are each independently 0 or 1, and
“a1”, “a2”, “b1”, “b2”, “x11”, “x12”, “y11”, and “y12” are each independently an integer of 0 to 4,
where if “m1” is 0, “x11” is an integer of 1 or more, if “m1” is 1, “x11+y11” is an integer of 1 or more,
if “m2” is 0, “x12” is an integer of 1 or more, and if “m2” is 1, “x12+y12” is an integer of 1 or more, and
in Formula 1-A and Formula 1-B, Ar 1 and Ar 2 are the same as defined in Formula 1, and R 1 to R 3 , “a”, “b”, “x”, “y”, and Ad are the same as defined in Formula 2.

6. The organic electroluminescence device of claim 5 , wherein Formula 1-A is represented by any one selected from the following Formula 1-1 to Formula 1-3:

wherein, in Formula 1-1 to Formula 1-3, Ar 1 and Ar 2 are the same as defined in Formula 1, and R 1 to R 3 , “a”, “b”, “b”, “x”, “y”, and Ad are the same as defined in Formula 2.

7. The organic electroluminescence device of claim 5 , wherein Ar 1 and Ar 2 are each independently a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted phenanthryl group, a substituted or unsubstituted dibenzofuran group, or a substituted or unsubstituted dibenzothiophene group.

8. The organic electroluminescence device of claim 5 , wherein Ar 1 and Ar 2 are each independently an aryl group having 6 to 30 carbon atoms for forming a ring, the aryl group being an unsubstituted aryl group or an aryl group substituted with at least one selected from a halogen atom, a cyano group, an alkyl group having 1 to 20 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, an aryloxy group having 1 to 20 carbon atoms, an alkylthio group having 1 to 10 carbon atoms, an arylthio group having 1 to 20 carbon atoms, a triarylsilyl group having 18 to 50 carbon atoms, and an adamantyl group, or
a heteroaryl group having 2 to 30 carbon atoms for forming a ring, the heteroaryl group being an unsubstituted heteroaryl group or a heteroaryl group substituted with at least one selected from a halogen atom, a cyano group, an alkyl group having 1 to 20 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, an aryloxy group having 1 to 20 carbon atoms, an alkylthio group having 1 to 10 carbon atoms, an arylthio group having 1 to 20 carbon atoms, a triarylsilyl group having 18 to 50 carbon atoms, and an adamantyl group.

9. The organic electroluminescence device of claim 5 , wherein Ar 1 and Ar 2 are each independently represented by any one selected from the following Formula A-1 to Formula A-20:

10. The organic electroluminescence device of claim 1 , wherein the monoamine compound comprises at least one selected from compounds in the following Compound Group 1 and Compound Group 2:

Assignees

• Samsung Display Co Ltd

Inventors

• Takada Ichinori
• Imada Ichiro

Classifications

• H10K50/181

  Electron blocking layers · CPC title

• H10K85/633

  comprising polycyclic condensed aromatic hydrocarbons as substituents on the nitrogen atom · CPC title

• C09K11/06 Primary

  containing organic luminescent materials · CPC title

• C07F7/081

  comprising at least one atom selected from the elements N, O, halogen, S, Se or Te · CPC title

• C07C2603/26

  Phenanthrenes; Hydrogenated phenanthrenes · CPC title