Organic electroluminescent device

Patent metadata

Field	Value
Publication number	US-9893293-B2
Application number	US-201514937314-A
Country	US
Kind code	B2
Filing date	Nov 10, 2015
Priority date	Dec 2, 2014
Publication date	Feb 13, 2018
Grant date	Feb 13, 2018

Abstract

An organic EL device including an anode; an emission layer; an anode-side hole transport layer between the anode and the emission layer, the anode-side hole transport layer including an anode-side hole transport material and being doped with an electron accepting material; an intermediate hole transport layer between the anode-side hole transport layer and the emission layer, the intermediate hole transport layer including an intermediate hole transport material; and an emission layer-side hole transport layer between the intermediate hole transport layer and the emission layer, the emission layer-side hole transport layer being adjacent to the emission layer, wherein the emission layer-side hole transport layer includes an emission layer-side hole transport material represented by the following Formula 1:

First claim

What is claimed is:

1. An organic electroluminescent (EL) device, comprising:
an anode;
an emission layer;
an anode-side hole transport layer between the anode and the emission layer, the anode-side hole transport layer including an anode-side hole transport material and being doped with an electron accepting material;
an intermediate hole transport layer between the anode-side hole transport layer and the emission layer, the intermediate hole transport layer including an intermediate hole transport material; and
an emission layer-side hole transport layer between the intermediate hole transport layer and the emission layer, the emission layer-side hole transport layer being adjacent to the emission layer,
wherein the intermediate hole transport layer and the emission layer-side hole transport layer are in contact with each other,
wherein the emission layer-side hole transport layer includes an emission layer-side hole transport material represented by the following Formula 1:

wherein, in Formula 1,
Ar 1 and Ar 2 are each independently a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms or a substituted or unsubstituted heteroaryl group having 5 to 50 ring carbon atoms,
R 1 to R 3 are each independently a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, a substituted or unsubstituted heterocyclic group having 3 to 50 ring carbon atoms, adjacent ones of R 1 to R 3 being separate or bound to form a ring,
m is an integer of 0 to 4,
p and q are each independently an integer of 0 to 5,
L 1 is a direct linkage, a substituted or unsubstituted arylene group having 6 to 18 ring carbon atoms, or a substituted or unsubstituted heteroarylene group having 5 to 15 ring carbon atoms, and
carbon atoms a and b are separate.

2. The organic EL device as claimed in claim 1 , wherein the intermediate hole transport material includes a compound represented by the following Formula 2:

wherein, in Formula 2,
Ar 1 to Ar 3 are each independently a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms or a substituted or unsubstituted heteroaryl group having 5 to 50 ring carbon atoms,
Ar 4 is a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, a substituted or unsubstituted heteroaryl group having 5 to 50 ring carbon atoms, or a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, and
L 1 is a direct linkage, a substituted or unsubstituted arylene group having 6 to 18 ring carbon atoms, or a substituted or unsubstituted heteroarylene group having 5 to 15 ring carbon atoms.

3. The organic EL device as claimed in claim 2 , wherein the anode-side hole transport material includes the compound represented by Formula 2.

4. The organic EL device as claimed in claim 1 , wherein the electron accepting material has a lowest unoccupied molecular orbital (LUMO) level of about −9.0 eV to about −4.0 eV.

5. The organic EL device as claimed in claim 1 , wherein the anode-side hole transport layer is adjacent to the anode.

6. The organic EL device as claimed in claim 1 , wherein the emission layer includes a compound represented by the following Formula 3:

wherein, in Formula 3,
each Ar 1 is independently a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 50 carbon atoms, a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 50 ring carbon atoms, a substituted or unsubstituted arylthio group having 6 to 50 ring carbon atoms, a substituted or unsubstituted alkoxycarbonyl group having 2 to 50 carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, a substituted or unsubstituted heteroaryl group having 5 to 50 ring carbon atoms, a substituted or unsubstituted silyl group, a carboxyl group, a halogen atom, a cyano group, a nitro group, or a hydroxyl group, and
n is an integer of 1 to 10.

7. The organic EL device as claimed in claim 1 , wherein the emission layer-side hole transport material represented by Formula 1 is one of the following Compounds 1 to 12:

8. An organic electroluminescent (EL) device, comprising:
an anode;
an emission layer;
an anode-side hole transport layer between the anode and the emission layer, the anode-side hole transport layer including an electron accepting material;
an intermediate hole transport layer between the anode-side hole transport layer and the emission layer, the intermediate hole transport layer including an intermediate hole transport material; and
an emission layer-side hole transport layer between the intermediate hole transport layer and the emission layer, the emission layer-side hole transport layer being adjacent to the emission layer,
wherein the intermediate hole transport layer and the emission layer-side hole transport layer are in contact with each other,
wherein the emission layer-side hole transport layer includes an emission layer-side hole transport material represented by the following Formula 1:

wherein, in Formula 1,
Ar 1 and Ar 2 are each independently a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms or a substituted or unsubstituted heteroaryl group having 5 to 50 ring carbon atoms,
R 1 to R 3 are each independently a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, a substituted or unsubstituted heterocyclic group having 3 to 50 ring carbon atoms, adjacent ones of R 1 to R 3 being separate or bound to form a ring,
m is an integer of 0 to 4,
p and q are each independently an integer of 0 to 5,
L 1 is a direct linkage, a substituted or unsubstituted arylene group having 6 to 18 ring carbon atoms, or a substituted or unsubstituted heteroarylene group having 5 to 15 ring carbon atoms, and
carbon atoms a and b are separate.

9. The organic EL device as claimed in claim 8 , wherein the intermediate hole transport material includes a compound represented by the following Formula 2:

wherein, in Formula 2,
Ar 1 to Ar 3 are each independently a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms or a substituted or unsubstituted heteroaryl group having 5 to 50 ring carbon atoms,
Ar 4 is a hydrogen atom, a deuterium atom, a halogen atom, a substituted o

Assignees

• Samsung Display Co Ltd

Inventors

• Sasaki Ikuo
• Jin Xiulan
• Ueno Masatsugu
• Matsuoka Koushin

Classifications

• C07D403/10

  linked by a carbon chain containing aromatic rings · CPC title

• C07C211/61

  with at least one of the condensed ring systems formed by three or more rings · CPC title

• C09K11/025

  non-luminescent particle coatings or suspension media · CPC title

• C07C211/44

  having amino groups bound to only one six-membered aromatic ring · CPC title

• C07C211/49

  having at least two amino groups bound to the carbon skeleton · CPC title