Organic light emitting element

Patent metadata

Field	Value
Publication number	US-11877464-B2
Application number	US-201816497275-A
Country	US
Kind code	B2
Filing date	May 11, 2018
Priority date	May 31, 2017
Publication date	Jan 16, 2024
Grant date	Jan 16, 2024

Abstract

Provided is an organic light emitting device that includes an anode, a cathode provided to face the anode, and one or more light emitting units provided between the anode and the cathode, wherein the organic light emitting device includes a charge generation layer provided between the anode and the one light emitting unit, or between the two light emitting units adjacent to each other among the light emitting units, the charge generation layer comprises a p-type charge injection layer, a p-type charge generation layer, or a layer which simultaneously injects and generates p-type charges, and the p-type charge injection layer, the p-type charge generation layer, or the layer which simultaneously injects and generates p-type charges has electric conductivity of 1×10 −6 S/cm or more.

First claim

The invention claimed is:

1. An organic light emitting device comprising:
an anode;
a cathode provided to face the anode; and
one or more light emitting units provided between the anode and the cathode,
wherein the organic light emitting device includes a charge generation layer provided between the anode and the one light emitting unit, or between the two light emitting units adjacent to each other among the light emitting units,
the charge generation layer comprises a p-type charge injection layer, a p-type charge generation layer, or a layer which simultaneously injects and generates p-type charges, and
the p-type charge injection layer, the p-type charge generation layer, or the layer which simultaneously injects and generates p-type charges has electric conductivity of 1×10 −6 S/cm or more,
wherein the p-type charge injection layer, the p-type charge generation layer, or the layer which simultaneously injects and generates p-type charges comprises:
a compound of the following Chemical Formula 1-1 or 1-2; and
one or more of compounds of the following Chemical Formulae 2 to 4 at a weight ratio of 20:80 to 80:20:

wherein in Chemical Formula 1-1 or 1-2:
X1 to X4 are the same as or different from each other, and are each independently hydrogen, a nitrile group, a nitro group, a halogen group, a carboxyl group, a carbonyl group, a substituted or unsubstituted haloalkyl group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted heteroaryloxy group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group, or adjacent groups are optionally bonded to each other to form a substituted or unsubstituted ring;
R1 and R3 are the same as or different from each other, and are each independently hydrogen, a nitrile group, a halogen group, a substituted or unsubstituted haloalkyl group, a substituted or unsubstituted haloalkoxy group, a substituted or unsubstituted halothioalkoxy group, a substituted or unsubstituted ether group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted thioalkoxy group, a substituted or unsubstituted silyl group, a substituted or unsubstituted heteroaryl group, a substituted or unsubstituted aryl group selected from the group consisting of a biphenyl group, a terphenyl group, a naphthyl group, an anthracenyl group, a phenanthryl group, a triphenyl group, a pyrenyl group, a phenalenyl group, a perylenyl group, a chrysenyl group, and a fluorenyl group, or a phenyl group substituted with one or more selected from the group consisting of a halogen group, a nitrile group, a haloalkyl group, a haloalkoxy group, a halothioalkoxy group, and a silyl group substituted with an alkyl group;
R2 and R4 are the same as or different from each other, and are each independently hydrogen, a nitrile group, a halogen group, a substituted or unsubstituted haloalkyl group, a substituted or unsubstituted haloalkoxy group, a substituted or unsubstituted halothioalkoxy group, a substituted or unsubstituted ether group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted thioalkoxy group, a substituted or unsubstituted silyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group; and
Q1 and Q2 are the same as or different from each other, and are each independently hydrogen; a halogen group; a nitrile group; a substituted or unsubstituted haloalkyl group; a substituted or unsubstituted haloalkoxy group; an aryl group that is unsubstituted or substituted with one or more selected from the group consisting of a nitrile group, a haloalkyl group, and a haloalkoxy group; or a substituted or unsubstituted heteroaryl group;

wherein in Chemical Formula 2:
L1 is a substituted or unsubstituted arylene group or a substituted or unsubstituted heteroarylene group;
R5 to R8 are the same as or different from each other, and are each independently a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted alkylthioxy group, a substituted or unsubstituted arylthioxy group, a substituted or unsubstituted alkylsulfoxy group, a substituted or unsubstituted arylsulfoxy group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted silyl group, a substituted or unsubstituted boron group, a substituted or unsubstituted arylphosphine group, a substituted or unsubstituted phosphine oxide group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group, or adjacent groups are optionally bonded to each other to form a substituted or unsubstituted ring;
a is an integer from 1 to 10; and
when a is 2 or more, two or more L1s are the same as or different from each other;

wherein in Chemical Formula 3:
L2 is a substituted or unsubstituted arylene group;
R9 to R11 are the same as or different from each other, and are each independently a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted alkylthioxy group, a substituted or unsubstituted arylthioxy group, a substituted or unsubstituted alkylsulfoxy group, a substituted or unsubstituted arylsulfoxy group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted silyl group, a substituted or unsubstituted boron group, a substituted or unsubstituted arylphosphine group, a substituted or unsubstituted phosphine oxide group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group;
R101 and R102 are the same as or different from each other, and are each independently hydrogen, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted alkylthioxy group, a substituted or unsubstituted arylthioxy group, a substituted or unsubstituted alkylsulfoxy group, a substituted or unsubstituted arylsulfoxy group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted silyl group, a substituted or unsubstituted boron group, a substituted or unsubstituted arylphosphine group, a substituted or unsubstituted phosphine oxide group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group;
b is an integer from 1 to 10;
when b is 2 or more, two or more L2s are the same as or different from each other;
r101 is an integer from 1 to 4;
r102 is an integer from 1 to 3; and
when r101 and r102 are each 2 or more, two or more structures in the parenthesis are the same as or different from each other;

wherein in Chemical Formula 4:
L3 to L5 are the same as or different from each other, and are each independently a direct bond, a substituted or unsubstituted arylene group, or a substituted or unsubstituted heteroarylene group;
Ar1 is a substituted or unsubstituted aryl group or a substituted or unsubstituted he

Assignees

• Lg Chemical Ltd

Inventors

• Kim Dongheon
• Heo Nansra
• Hong Wanpyo
• Kim Yeon Hwan
• Choi Heungwoo
• Yun Jun
• Lee Hyungjin
• Ha Jae Seung

Classifications

• H10K50/19 Primary

  Tandem OLEDs · CPC title

• C07C211/54

  having amino groups bound to two or three six-membered aromatic rings · CPC title

• C07C211/61

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

• C07C255/47

  to carbon atoms of rings being part of condensed ring systems · CPC title

• H10K85/615

  Polycyclic condensed aromatic hydrocarbons, e.g. anthracene · CPC title