Organic light-emitting device

Patent metadata

Field	Value
Publication number	US-11271167-B2
Application number	US-201515128381-A
Country	US
Kind code	B2
Filing date	Apr 1, 2015
Priority date	Apr 4, 2014
Publication date	Mar 8, 2022
Grant date	Mar 8, 2022

Abstract

Disclosed is an organic light emitting diode including a cathode, an anode, a light emitting layer provided between the cathode and the anode, a first electron transporting layer including a heterocyclic compound represented by Formula 1 and provided between the cathode and the light emitting layer, and a second electron transporting layer including a host material including one or two or more of compounds represented by Formulae 3 to 5 and one or two or more n-type dopants selected from alkali metals and alkaline earth metals and provided between the cathode and the first electron transporting layer:

First claim

The invention claimed is:

1. An organic light emitting diode comprising:
a cathode;
an anode;
a light emitting layer provided between the cathode and the anode;
a first electron transporting layer comprising a heterocyclic compound represented by the following Formula 1 and provided between the cathode and the light emitting layer to be in physical contact with the light emitting layer; and
a second electron transporting layer provided between the cathode and the first electron transporting layer,
wherein the light emitting layer comprises a host and a dopant, and a difference between a HOMO energy level of the host and a HOMO energy level of the heterocyclic compound represented by Formula 1 is 0.2 eV or more,
wherein the second electron transporting layer includes a host material including one or two or more of compounds represented by the following Formula 3, and one or two or more n-type dopants selected from alkali metals and alkaline earth metals,
wherein the organic light emitting diode comprises two or more light emitting layers, and comprises a charge generating layer between two adjacent light emitting layers among the two or more light emitting layers,
wherein the charge generating layer comprises the second electron transporting layer and a p-type organic material layer, and
wherein the first electron transporting layer is provided between an adjacent light emitting layer among the two or more light emitting layers and the second electron transporting layer:

in Formula 1,
Ar1 to Ar3 are different from each other,
Ar1 and Ar2 are different from each other, and are each independently a phenyl group; a biphenyl group; a terphenyl group; a naphthyl group; or a phenanthryl group, which is unsubstituted or substituted with deuterium; a phenyl group; a naphthyl group; or a phenanthryl group,
Ar3 is represented by the following Formula 2,

in Formula 2,
R1 and R2 are each independently hydrogen or deuterium, or optionally combine with an adjacent R1 or R2 respectively to form a fused benzene ring,
R3 and R4 are the same as or different from each other, and each independently hydrogen; deuterium; a C1 to C10 alkyl group; or a phenyl group,
L1 is a direct bond; a phenylene group unsubstituted or substituted with a deuterium; a divalent biphenyl group; a naphthylene group; or a phenanthrylene group,
1 is an integer of 1 to 5,
m is an integer of 1 to 3,
n is an integer of 1 to 4,
when 1, m, and n are each an integer of 2 or more, two or more structures in the parenthesis are the same as or different from each other,

in Formula 3,
A1 and A2 are the same as or different from each other, and each independently an alkyl group having 1 to 10 carbon atoms; a phenyl group; a naphthyl group; or a fluorenyl group substituted with an alkyl group having 1 to 10 carbon atoms,
L2 and L3 are the same as or different from each other, and each independently a direct bond; a phenylene group unsubstituted or substituted with a phenyl group; a naphthylene group; or a divalent biphenyl group,
A is any one of the following substituted or unsubstituted structures,

X is O; S; or CT12T13,
and p are an integer of 1 to 3, and
when o and p are an integer of 2 or more, two or more structures in the parenthesis are the same as or different from each other,
T1 to T8 are hydrogen,
T12 and T13 are the same as or different from each other, and each independently hydrogen or a C1 to C10 alkyl group.

2. The organic light emitting diode of claim 1 , wherein the first electron transporting layer further comprises an n-type dopant represented by the following Formula 10:

A3 is hydrogen; deuterium; a halogen group; a nitrile group; a nitro group; a hydroxy group; 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 aryl group; or substituted or unsubstituted heterocyclic group,
a curved line represents two or three carbon atoms required for forming a 5-membered or 6-membered ring having M, and each of the two or three carbon atoms are unsubstituted or substituted with one or two substituents having the same definition as A3, and
M is an alkali metal or an alkaline earth metal,
wherein the A3 on nitrogen atom and the substituents on the two or three carbon atoms in the curved line optionally combine with each other to form a fused ring, and
wherein the substituents on the two or three carbon atoms in the curved line optionally combine with each other to form a fused ring.

3. The organic light emitting diode of claim 2 , wherein the n-type dopant represented by Formula 10 is represented by the following Formula 10-1 or 10-2:

in Formulae 10-1 and 10-2,
M is the same as that defined in Formula 10, and
Formulae 10-1 and 10-2 are each independently unsubstituted or substituted with one or two or more substituents selected from the group consisting of hydrogen; deuterium; a halogen; a nitrile group; a nitro group; a hydroxy group; 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 aryl group; and a substituted or unsubstituted heterocyclic group, or adjacent substituents combine with each other to form a substituted or unsubstituted hydrocarbon ring or a substituted or unsubstituted hetero ring.

4. The organic light emitting diode of claim 1 , wherein a triplet energy of the heterocyclic compound represented by Formula 1 is 2.2 eV or more.

5. The organic light emitting diode of claim 1 , wherein a dipole moment of the heterocyclic compound represented by Formula 1 is 2 debye or less.

6. The organic light emitting diode of claim 1 , wherein an electron mobility of the heterocyclic compound represented by Formula 1 is 10 −6 cm 2 /Vs or more.

7. The organic light emitting diode of claim 1 , wherein the heterocyclic compound represented by Formula 1 is represented by the following Formula 1-B:

R1 to R4, Ar1, L1, 1, m, and n are the same as defined in Formula 1,

Assignees

• Lg Chemical Ltd

Inventors

• Jang Boonjae
• Lee Dong Hoon
• Huh Jungoh
• Kang Minyoung
• Heo Dong Uk
• Han Miyeon
• Jung Wooyung
• Jung Min Woo

Classifications

• C07F9/6561

  containing systems of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring or ring system, with or without other non-condensed hetero rings · CPC title

• C07D401/14

  containing three or more hetero rings · CPC title

• C07D219/06

  Oxygen atoms · CPC title

• C07D277/66

  with aromatic rings or ring systems directly attached in position 2 · CPC title

• C07D409/14

  containing three or more hetero rings · CPC title