Organic light-emitting diode including multi-layered hole transporting layer, and flat display device including the organic light-emitting diode

Patent metadata

Field	Value
Publication number	US-9299936-B2
Application number	US-201213543714-A
Country	US
Kind code	B2
Filing date	Jul 6, 2012
Priority date	Dec 2, 2011
Publication date	Mar 29, 2016
Grant date	Mar 29, 2016

Abstract

An organic light-emitting diode including: a first mixed layer between an emission layer and a first electrode and including first and second compounds; a second mixed layer between the emission layer and the first mixed layer and including third and fourth compounds; a first charge generation layer between the first mixed layer and the first electrode and including the first and second compounds and a first charge generation material; a second charge generation layer between the first mixed layer and the second mixed layer and including the third and fourth compounds and a second charge generation material; and a buffer layer between the emission layer and the second mixed layer, the first and the third compounds are each independently a compound represented by Formula 1 below, and the second compound and fourth compounds are each independently a compound represented by Formula 2 below:

First claim

What is claimed is:

1. An organic light-emitting diode comprising:
a first electrode;
a second electrode facing the first electrode;
an emission layer between the first electrode and the second electrode;
a first mixed layer between the emission layer and the first electrode and comprising a first compound and a second compound;
a second mixed layer between the emission layer and the first mixed layer and comprising a third compound and a fourth compound;
a first charge generation layer between the first mixed layer and the first electrode and comprising the first compound, the second compound, and a first charge generation material;
a second charge generation layer between the first mixed layer and the second mixed layer and comprising the third compound, the fourth compound, and a second charge generation material; and
a buffer layer between the emission layer and the second mixed layer,
wherein the first compound and the third compound are each independently a compound represented by Formula 1 below, and the second compound and the fourth compound are each independently a compound represented by Formula 2 below:

wherein in Formula 1,
Ar 11 and Ar 12 are each independently a substituted or unsubstituted C 6 -C 60 arylene group;
e and f are each independently an integer of 0 to 5;
R 51 to R 58 and R 61 to R 69 are each independently a hydrogen atom, a deuterium atom, a halogen atom, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, hydrazine, hydrazone, a carboxylic group or salt thereof, a sulfonic acid group or salt thereof, a phosphoric acid group or salt thereof, a substituted or unsubstituted C 1 -C 60 alkyl group, a substituted or unsubstituted C 2 -C 60 alkenyl group, a substituted or unsubstituted C 2 -C 60 alkynyl group, a substituted or unsubstituted C 1 -C 60 alkoxy group, a substituted or unsubstituted C 3 -C 60 cycloalkyl group, a substituted or unsubstituted C 6 -C 60 aryl group, a substituted or unsubstituted C 6 -C 60 aryloxy group, or substituted or unsubstituted C 6 -C 60 arylthio group; and
R 59 is a phenyl group, a naphthyl group, an anthryl group, a biphenyl group, or a pyridyl group or is a phenyl group, a naphthyl group, an anthryl group, a biphenyl group, or a pyridyl group, of which at least one hydrogen atom is each independently substituted with a deuterium atom; a halogen atom, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, hydrazine, hydrazone, a carboxylic group or salt thereof, a sulfonic acid group or salt thereof, a phosphoric acid group or salt thereof, a substituted or unsubstituted C 1 -C 20 alkyl group, or a substituted or unsubstituted C 1 -C 20 alkoxy; and

wherein in Formula 2,
Ar 1 to Ar a are each independently a substituted or unsubstituted C 6 -C 60 arylene group;
a and b are each independently an integer of 0 to 5;
c is an integer of 1 to 5;
R 1 to R 5 are each independently a hydrogen atom, a deuterium atom, a halogen atom, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, hydrazine, hydrazone, a carboxylic group or salt thereof, a sulfonic acid group or salt thereof; a phosphoric acid group or salt thereof; a substituted or unsubstituted C 1 -C 60 alkyl group, a substituted or unsubstituted C 2 -C 60 alkenyl group, a substituted or unsubstituted C 2 -C 60 alkynyl group, a substituted or unsubstituted C 1 -C 60 alkoxy group, a substituted or unsubstituted C 3 -C 60 cycloalkyl group, a substituted or unsubstituted C 6 -C 60 aryl group, a substituted or unsubstituted C 6 -C 60 aryloxy group, a substituted or unsubstituted C 6 -C 60 arylthio group, —Si(R 31 )(R 32 )(R 33 ), —N(R 34 )(R 35 ), or a nitrogen atom-containing group, and at least one of R 1 to R 5 is a nitrogen atom-containing group;
d is an integer of 0 to 5;
R 11 to R 23 are each independently a hydrogen atom, a deuterium atom, a halogen atom, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, hydrazine, hydrazone, a carboxylic group or salt thereof, a sulfonic acid group or salt thereof, a phosphoric acid group or salt thereof, a substituted or unsubstituted C 1 -C 60 alkyl group, a substituted or unsubstituted C 2 -C 60 alkenyl group, a substituted or unsubstituted C 2 -C 60 alkynyl group, a substituted or unsubstituted C 1 -C 60 alkoxy group, a substituted or unsubstituted C 3 -C 60 cycloalkyl group, a substituted or unsubstituted C 6 -C 60 aryl group, a substituted or unsubstituted C 6 -C 60 aryloxy group, a substituted or unsubstituted C 6 -C 60 arylthio group, —Si(R 36 )(R 37 )(R 38 ), or —N(R 39 )(R 40 ); and
R 31 to R 40 are each independently a hydrogen atom, a deuterium atom, a halogen atom, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, hydrazine, hydrazone, a carboxylic group or salt thereof, a sulfonic acid group or salt thereof, a phosphoric acid group or salt thereof, a substituted or unsubstituted C 1 -C 60 alkyl group, a substituted or unsubstituted C 2 -C 60 alkenyl group, a substituted or unsubstituted C 2 -C 60 alkynyl group, a substituted or unsubstituted C 1 -C 60 alkoxy group, a substituted or unsubstituted C 3 -C 60 cycloalkyl group, a substituted or unsubstituted C 6 -C 60 aryl group, a substituted or unsubstituted C 6 -C 60 aryloxy group, a substituted or unsubstituted C 6 -C 60 arylthio group, or a substituted or unsubstituted C 2 -C 60 heteroaryl group;
wherein the nitrogen atom-containing group is a 5-membered aromatic ring group comprising a nitrogen atom as a ring atom, a 6-membered aromatic ring group comprising a nitrogen atom as a ring atom, or a 9-membered aromatic ring group comprising a nitrogen atom as a ring atom and is formed by fusing a 5-membered aromatic group and a 6-membered aromatic group.

2. The organic light-emitting diode of claim 1 , wherein a highest occupied molecular orbital (HOMO) energy level of the second compound is 0.1 eV to 0.2 eV lower than a HOMO energy level of the first compound, and a lowest unoccupied molecular orbital (LUMO) energy level of the second compound is 0.1 eV to 0.2 eV lower than a LUMO energy level of the first compound.

3. The organic light-emitting diode of claim 1 , wherein a hole mobility of the first compound is higher than a hole mobility of the second compound.

4. The organic light-emitting diode of claim 1 , wherein the first compound and the third compound are each independently a compound represented by Formula 1A:

wherein in Formula 1A,
R 51 , R 59 , R 61 , and R 62 are the same as with respect to Formula 1.

5. The organic light-emitting diode of claim 1 , wherein the first compound and the third compound are each independently Compound 301 below:

6. The organic light-emitting diode of claim 1 , wherein the second compound and the fourth compound are each independently at least one of compounds represented by Formulae 2A to 2K below:

Assignees

• Kho Sam-Il
• Park Mie-Hwa
• Jeong Hye-In
• Kwak Yoon-Hyun
• Shin Dae-Yup
• Lee Kwan-Hee
• Samsung Display Co Ltd

Inventors

• Kho Sam-Il
• Park Mie-Hwa
• Jeong Hye-In
• Kwak Yoon-Hyun
• Shin Dae-Yup
• Lee Kwan-Hee

Classifications

• H01L51/006

  Electricity · mapped topic

• H01L51/5064

  Electricity · mapped topic

• H01L51/0061

  Electricity · mapped topic

• H01L51/0067 Primary

  Electricity · mapped topic

• C07D403/12

  linked by a chain containing hetero atoms as chain links · CPC title