Organic electroluminescent device

Patent metadata

Field	Value
Publication number	US-10385262-B2
Application number	US-201816233058-A
Country	US
Kind code	B2
Filing date	Dec 26, 2018
Priority date	Nov 7, 2014
Publication date	Aug 20, 2019
Grant date	Aug 20, 2019

Abstract

An organic electroluminescent device of which emission life may be improved. The organic electroluminescent device includes an anode, an emission layer, and an anode-side hole transport layer provided between the anode and the emission layer and including an anode-side hole transport material. An electron accepting material is doped in the anode-side hole transport layer. An intermediate hole transport material layer is provided between the anode-side hole transport layer and the emission layer and includes an intermediate hole transport material, and an emission layer-side hole transport layer is provided between the intermediate hole transport material layer and the emission layer and adjacent to the emission layer. 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; and
a hole transport region between the anode and the emission layer;
wherein the hole transport region comprises hole transport materials each of which is represented by Formula 1 and Formula 2:

wherein in Formula 1, Y is O or S;
R 1 to R 6 are each independently hydrogen, deuterium, a halogen atom, a substituted or unsubstituted alkyl group having 1 to 15 carbon atoms, a substituted or unsubstituted silyl group, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms for forming a ring, a substituted or unsubstituted heteroaryl group having 1 to 30 carbon atoms for forming a ring, or a substituted or unsubstituted aryl group or heteroaryl group formed via condensation of optional adjacent substituents;
Ar 1 and Ar 2 are each independently a substituted or unsubstituted aryl group having 6 to 30 carbon atoms for forming a ring, and each of Ar 1 and Ar 2 is not a heteroaryl-containing group;
L 1 to L 3 are each independently a direct linkage, a substituted or unsubstituted alkylene group having 1 to 15 carbon atoms, a substituted or unsubstituted aralkylene group having 7 to 30 carbon atoms, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms for forming a ring, a substituted or unsubstituted heteroarylene group having 1 to 30 carbon atoms for forming a ring, or a substituted or unsubstituted divalent silyl group;
m is an integer from 0 to 3, and
n is an integer from 0 to 4,
wherein in Formula 2, Ar 7 to Ar 9 are each independently a substituted or unsubstituted aryl group having 6 to 50 carbon atoms for forming a ring, or a substituted or unsubstituted heteroaryl group having 5 to 50 carbon atoms for forming a ring;
Ar 10 is hydrogen, deuterium, a halogen atom, a substituted or unsubstituted aryl group having 6 to 50 carbon atoms for forming a ring, a substituted or unsubstituted heteroaryl group having 5 to 50 carbon atoms for forming a ring, or a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms; and
L 4 is a direct linkage, a substituted or unsubstituted arylene group having 6 to 18 carbon atoms for forming a ring, or a substituted or unsubstituted heteroarylene group having 5 to 15 carbon atoms for forming a ring.

2. The organic EL device of claim 1 , wherein the hole transport region comprises a hole injection layer between the anode and the emission layer;
an anode-side hole transport layer between the hole injection layer and the emission layer;
an intermediate hole transport material layer between the anode-side hole transport layer and the emission layer; and
an emission layer-side hole transport layer between the intermediate hole transport material layer and the emission layer.

3. The organic EL device of claim 2 , wherein at least one of the intermediate hole transport material layer or the anode-side hole transport layer comprises a compound represented by Formula 2.

4. The organic EL device of claim 2 , wherein the anode-side hole transport layer comprises an anode-side hole transport material and doped with an electron accepting material, and
the electron accepting material has a lowest unoccupied molecular orbital (LUMO) level within a range from about −9.0 eV to about −4.0 eV.

5. The organic EL device of claim 4 , wherein the anode-side hole transport material is represented by Formula 2.

6. The organic EL device of claim 4 , wherein the electron accepting material is at least one selected from the group consisting of compounds represented in the following formulae 4-1 to 4-14:

wherein in Formulae 4-1 to 4-14,
R is a hydrogen atom, a deuterium atom, a halogen atom, a fluoroalkyl group having 1 to 50 carbon atoms, a cyano group, an alkoxy group having 1 to 50 carbon atoms, an alkyl group having 1 to 50 carbon atoms, an aryl group having 6 to 50 carbon atoms or a heteroaryl group having 5 to 50 carbon atoms for forming a ring,
Ar is a substituted or unsubstituted aryl group having 6 to 50 carbon atoms for forming a ring or a substituted or unsubstituted heteroaryl group having 5 to 50 carbon atoms for forming a ring,
Y is a methine group (—CH═) or a nitrogen atom (—N═),
Z is a pseudohalogen atom or a substituted sulfur atom, n is an integer of 10 and less, and X is one of the substituents represented by the following formulae X1 to X7:

wherein in Formulae X1 to X7,
Ra is a hydrogen atom, a deuterium atom, a halogen atom, a fluoroalkyl group having 1 to 50 carbon atoms, a cyano group, an alkoxy group having 1 to 50 carbon atoms, an alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 carbon atoms for forming a ring or a substituted or unsubstituted heteroaryl group having 5 to 50 carbon atoms for forming a ring.

7. The organic EL device of claim 2 , wherein the anode-side hole transport layer comprises an electron accepting material as a main component, and
the electron accepting material has a lowest unoccupied molecular orbital (LUMO) level within a range from about −9.0 eV to about −4.0 eV.

8. The organic EL device of claim 1 , wherein the emission layer comprises a compound represented by Formula 3:

wherein in Formula 3, Ar 11 is each independently hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 carbon atoms for forming a ring, 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 carbon atoms for forming a ring, a substituted or unsubstituted arylthio group having 6 to 50 carbon atoms for forming a ring, a substituted or unsubstituted alkoxycarbonyl group having 2 to 50 carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 carbon atoms for forming a ring, a substituted or unsubstituted heteroaryl group having 5 to 50 carbon atoms for forming a ring, a substituted or unsubstituted silyl group, a carboxyl group, a halogen atom, a cyano group, a nitro group, or a hydroxyl group; and
o is an integer from 1 to 10.

9. The organic EL device of claim 1 , wherein the hole transport material represented by Formula 1 is at least one selected from the group consisting of compounds represented in the following Compound Group 1:

Assignees

• Samsung Display Co Ltd

Inventors

• Matsuura Toshiyuki
• Itoi Hiroaki
• Sakamoto Naoya
• Akashi Nobutaka

Classifications

• C09K11/025 Primary

  non-luminescent particle coatings or suspension media · CPC title

• C07D403/10

  linked by a carbon chain containing aromatic rings · CPC title

• C07D401/14

  containing three or more hetero rings · CPC title

• C07C211/44

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

• C07C211/61

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