Organic electroluminescent element

Patent metadata

Field	Value
Publication number	US-9412964-B2
Application number	US-201313914540-A
Country	US
Kind code	B2
Filing date	Jun 10, 2013
Priority date	Jun 12, 2012
Publication date	Aug 9, 2016
Grant date	Aug 9, 2016

Abstract

[It is an object] to provide an organic electroluminescent element with which the initial durability of the element can be greatly improved while maintaining the efficiency of the element at a high level. This is an organic electroluminescent element having an anode, a hole injection layer, a first hole transport layer, a second hole transport layer, a light-emitting layer, and a cathode, in this order, with this organic electroluminescent element being such that the aforementioned hole injection layer includes a material for which the energy of the lowest unoccupied molecular orbital (LUMO) is less than −4.0 eV and also such that the energy E1(LUMO) of the LUMO of the material included in the aforementioned first hole transport layer and the energy E2(LUMO) of the LUMO of the material included in the aforementioned second hole transport layer satisfy [the inequality] E1(LUMO)>E2(LUMO).

First claim

The invention claimed is:

1. An organic electroluminescent element having an anode, a hole injection layer, a first hole transport layer, a second hole transport layer, a light-emitting layer, and a cathode, in this order, wherein
this hole injection layer includes a material for which the energy of the lowest unoccupied molecular orbital (LUMO) is less than −4.0 eV, and the energy E1(LUMO) of the LUMO of the material included in said first hole transport layer and the energy E2(LUMO) of the LUMO of the material included in said second hole transport layer satisfy the inequality: E1(LUMO)>E2(LUMO).

2. The organic electroluminescent element according to claim 1 , wherein said first hole transport layer includes at least one type of material expressed by any of General Formulas 1 to 3 below:

M represents the following structure, wherein if M is bonded to X, then M represents a structure in which hydrogen atoms have been removed from the benzene ring of the following structure in a number corresponding to the number of bonded X groups:

wherein: R 1 , R 2 , and R 3 each independently represents an alkyl group, a cycloalkyl group, a silyl group, an alkoxy group, an aryloxy group, an alkylthio group, or an arylthio group; R 1 , R 2 , and R 3 may each bond together to form a ring;
X groups each independently represents one of the following structures:

wherein: R 4 and R 5 each independently represents an alkyl group, a cycloalkyl group, a silyl group, an alkoxy group, an aryloxy group, an alkylthio group, or an arylthio group; R 4 and R 5 may bond together to form a ring; and
n represents an integer greater than or equal to 0.

3. The organic electroluminescent element according to claim 1 , wherein the energy E1(LUMO) of the LUMO of the material included in said first hole transport layer and the energy E2(LUMO) of the LUMO of the material included in said second hole transport layer satisfy [the inequality] E1(LUMO)>E2(LUMO)+0.3 eV.

4. The organic electroluminescent element according to claim 1 , wherein said second hole transport layer includes at least one type of material expressed by either of General Formulas 4 and 5 below:

wherein: Ar 1 and Ar 2 represent each independently an aryl group; aryl groups Ar 1 and Ar 2 may be substituted with an alkyl group, an aryl group, or an amino group;
Ar 3 represents an amino group substituted with an alkyl group or an aryl group; the aryl group substituted on the amino group of Ar 3 may be further substituted with an alkyl group, an aryl group, or an amino group; and the alkyl group or aryl group substituted on the amino group of Ar 3 may form a ring by bonding to another alkyl group or aryl group substituted on the amino group of Ar 3 ;
Z represents one of the following structures:

R 6 to R 8 represent each independently an alkyl group or an aryl group; and the aryl group of R 6 to R 8 may be substituted with an alkyl group, an aryl group, or an amino group.

5. The organic electroluminescent element according to claim 1 , wherein the material which is included in said hole injection layer and for which the energy of the LUMO is less than −4.0 eV is a material expressed by General Formula A below:
Rpi−(CN) j   General Formula A

wherein: Rpi indicates an organic group including four or more π electrons, and j indicates an integer from 1 to 8.

6. The organic electroluminescent element according to claim 1 , wherein the thickness of said first hole transport layer is 3 to 30 nm.

7. The organic electroluminescent element according to claim 1 , wherein the thickness of said second hole transport layer is 3 to 30 nm.

8. The organic electroluminescent element according to claim 1 , further comprising an electron transport layer between said light-emitting layer and said cathode.

9. The organic electroluminescent element according to claim 1 , wherein said light-emitting layer contains a light-emitting dopant and a host material, and said light-emitting dopant is a phosphorescent material.

10. The organic electroluminescent element according to claim 9 , wherein said phosphorescent material is an iridium complex.

11. A light-emitting device featuring the organic electroluminescent element according to claim 1 .

12. A display device featuring the organic electroluminescent element according to claim 1 .

13. A lighting device featuring the organic electroluminescent element according to claim 1 .

14. The electroluminescent element according to claim 1 , wherein the material included in the hole injection layer is compound HI-1:

the material included in said first hole transport layer is Compound A-1:

and the material included in said second hole transport layer is Compound B-4:

Assignees

• Udc Ireland Ltd

Inventors

• Sotoyama Wataru
• Inoue Daisuke

Classifications

• H10K50/171

  Electron injection layers · CPC title

• H10K50/11 Primary

  characterised by the electroluminescent [EL] layers · CPC title

• H01L51/0081

  Electricity · mapped topic

• H01L51/5092 Primary

  Electricity · mapped topic

• H01L51/5088

  Electricity · mapped topic