Organic light-emitting device

Patent metadata

Field	Value
Publication number	US-9543538-B2
Application number	US-201414530637-A
Country	US
Kind code	B2
Filing date	Oct 31, 2014
Priority date	Jan 17, 2014
Publication date	Jan 10, 2017
Grant date	Jan 10, 2017

Abstract

An organic light-emitting device includes a positive electrode, a negative electrode and at least one organic material layer between the positive electrode and the negative electrode. The at least one organic material layer includes a hole-injecting layer, a hole-transporting layer, an emission layer, an electron-transporting layer, and an electron-injecting layer, and the emission layer includes a host material and a dopant material. In addition, a lifetime enhancement layer including a bipolar compound is positioned between the emission layer and the electron-transporting layer.

First claim

What is claimed is:

1. An organic light-emitting device comprising:
a positive electrode;
a negative electrode; and
at least one organic material layer between the positive electrode and the negative electrode, wherein
the at least one organic material layer comprises a hole-injecting layer, a hole-transporting layer, an emission layer comprising a host material and a dopant material, an electron-transporting layer, an electron-injecting layer, and
a lifetime enhancement layer between the emission layer and the electron-transporting layer, the lifetime enhancement layer comprising a bipolar compound comprising an electron withdrawing group (EWG) and an electron donating group (EDG), the bipolar compound having an ionization potential of 5.5 eV or greater, a difference between an energy of the highest occupied molecular orbital and an energy of the lowest occupied molecular orbital of greater than 3.0 eV, a triplet energy of 2.3 eV or greater, and a difference between a singlet energy and the triplet energy of less than 0.5 eV,
wherein the bipolar compound is a compound represented by Formula 1:

where
X 1 is selected from the group consisting of O, S, Se, N(Ar 1 ), C(Ar 2 )(Ar 3 ), and Si(Ar 4 )(Ar 5 ),
Y 1 to Y 4 are each independently N or C(R 1 ), wherein a plurality of R 1 s are the same or different and one or more R 1 s optionally bind to a nearby group to form a condensed ring; and
X 2 and X 3 are each independently N or C (R 2 ), wherein a plurality of R 2 s are the same or different and one or more R 2 s optionally bind to a nearby group to form a condensed ring;
R 1 to R 2 , and Ar 1 to Ar 5 are each independently selected from the group consisting of a hydrogen, a deuterium, a halogen group, a cyano group, a nitro group, an amino group, a C 1 ˜C 40 alkyl group, a C 2 ˜C 40 alkenyl group, a C 2 ˜C 40 alkynyl group, a C 3 ˜C 40 cycloalkyl group, a heterocycloalkyl group having 3 to 40 ring atoms, a C 6 ˜C 60 aryl group, a heteroaryl group having 5 to 60 ring atoms, a C 1 ˜C 40 alkoxy group, a C 6 ˜C 60 aryloxy group, a C 1 ˜C 40 alkylsilyl group, a C 6 ˜C 60 arylsilyl group, a C 1 ˜C 40 alkylboron group, a C 6 ˜C 60 arylboron group, a C 1 ˜C 40 phosphine group, a C 1 ˜C 40 phosphine oxide group, and a C 6 ˜C 60 arylamine group, and
a C 1 ˜C 40 alkyl group, a C 2 ˜C 40 alkenyl group, a C 2 ˜C 40 alkynyl group, a C 3 ˜C 40 cycloalkyl group, a heterocycloalkyl group having 3 to 40 ring atoms, a C 6 ˜C 60 aryl group, a heteroaryl group having 5 to 60 ring atoms, a C 1 ˜C 40 alkoxy group, a C 6 ˜C 60 aryloxy group, a C 1 ˜C 40 alkysilyl group, a C 6 ˜C 60 arylsilyl group, a C 1 ˜C 40 alkylboron group, a C 6 ˜C 60 arylboron group, a C 1 ˜C 40 phosphine group, a C 1 ˜C 40 phosphine oxide group, and a C 6 ˜C 60 arylamine group each independently substituted with at least one selected from the group consisting of a deuterium, a halogen group, a cyano group, a nitro group, an amino group, a C 1 ˜C 40 alkyl group, a C 2 ˜C 40 alkenyl group, a C 2 ˜C 40 alkynyl group, a C 3 ˜C 40 cycloalkyl group, a heterocycloalkyl group having 3 to 40 ring atoms, a C 6 ˜C 40 aryl group, a heteroaryl group having 5 to 40 ring atoms, a C 1 ˜C 40 alkoxy group, a C 6 ˜C 60 aryloxy group, a C 1 ˜C 40 alkylsilyl group, a C 6 ˜C 60 arylsilyl group, a C 1 ˜C 40 alkylboron group, a C 6 ˜C 60 arylboron group, a C 1 ˜C 40 phosphine group, a C 1 ˜C 40 phosphine oxide group, and a C 6 ˜C 60 arylamine group.

2. The organic light-emitting device of claim 1 , wherein when the emission layer emits blue fluorescent light, green fluorescent light, or red phosphorescent light, the triplet energy of the bipolar compound in the lifetime enhancement layer is 2.3 eV or greater.

3. The organic light-emitting device of claim 1 , wherein when the emission layer emits green phosphorescent light, the bipolar compound has a triplet energy of 2.5 eV or greater and an ionization potential of 6.0 eV or greater.

4. The organic light-emitting device of claim 1 , wherein when the emission layer emits blue phosphorescent light, the bipolar compound has a triplet energy of 2.7 eV or greater and an ionization potential of 6.0 eV or greater.

5. The organic light-emitting device of claim 1 , wherein
the lifetime enhancement layer comprises an organic membrane layer having a thickness of 1 um or greater, and
electron mobility and hole mobility measured through transit time of a carrier at room temperature is each at least 1×10 −6 cm 2 /V·s or greater.

6. The organic light-emitting device of claim 1 , wherein the compound represented by Formula 1 is represented by Formulae A-1 to A-24:

7. The organic light-emitting device of claim 1 ,
wherein any one of Y 1 and Y 2 , Y 2 and Y 3 , or Y 3 and Y 4 of the compound represented by Formula 1 forms a condensed ring with a compound represented by Formula 2:

where
a dotted line represents a portion where the compound represented by Formula 2 is condensed with the compound represented by Formula 1,
Y 5 to Y 8 are each independently N or C(R 3 ), wherein a plurality of R 3 s are the same or different,
X 4 is selected from the group consisting of O, S, Se, N(Ar 1 ), C(Ar 2 )(Ar 3 ), and Si (Ar 4 ) (Ar 5 ),
at least one of X 1 and X 4 is N(Ar 1 ),
R 1 to R 3 and Ar 1 to Ar 5 are each independently selected from the group consisting of a hydrogen, a deuterium, a halogen group, a cyano group, a nitro group, an amino group, a C 1 ˜C 40 alkyl group, a C 2 ˜C 40 alkenyl group, a C 2 ˜C 40 alkynyl group, a C 3 ˜C 40 cycloalkyl group, a heterocycloalkyl group having 3 to 40 ring atoms, a C 6 ˜C 60 aryl group, a heteroaryl group having 5 to 60 ring atoms, a C 1 ˜C 40 alkoxy group, a C 6 ˜C 60 aryloxy group, a C 1 ˜C 40 alkylsilyl group, a C 6 ˜C 60 arylsilyl group, a C 1 ˜C 40 alkylboron group, a C 6 ˜C 60 arylboron group, a C 1 ˜C 40 phosphine group, a C 1 ˜C 40 phosphine oxide group, and a C 6 ˜C 60 arylamine group, and
a C 1 ˜C 40 alkyl group, a C 2 ˜C 40 alkenyl group, a C 2 ˜C 40 alkynyl group, a C 3 ˜C 40 cycloalkyl group, a heterocycloalkyl group having 3 to 40 ring atoms, a C 6 ˜C 60 aryl group, a heteroaryl group having 5 to 60 ring atoms, a C 1 ˜C 40 alkoxy group, a C 1 ˜C 60 aryloxy group, a C 1 ˜C 40 alkylsilyl group, a C 6 ˜C 60 arylsilyl group, a C 1 ˜C 40 alkylboron group, a C 6 ˜C 60 arylboron group, a C 1 ˜C 40 phosphine group, a C 1 ˜C 40 phosphine oxide group, and a C 6 ˜C 60 arylamine group each independently substituted with at least one selected from a deuterium, a halogen group, a cyano group, a nitro group, an amino group, a C 1 ˜C 40 alkyl group, a C 2 ˜C 40 alkenyl group, a C 2 ˜C 40 alkynyl group, a C 3 ˜C 40 cycloalkyl group, a heterocycloalkyl group having 3 to 40 ring atoms, a C 6 ˜C 40 aryl group, a heteroaryl group having 5 to 40 ring atoms, a C 1 ˜C 40 alkoxy group, a C 6 ˜C 60 aryloxy group, a C 1 ˜C 40 alkylsilyl group, a C 6 ˜C 60 arylsilyl group, a C 1 ˜C 40 alkylboron group, a C 6 ˜C 60 arylboron group, a C 1 ˜C 40 phosphine group, a C 1 ˜C 40 phosphine oxide group, and a C 6 ˜C 60 arylamine group, and
R 1 to R 3 optionally bind to a nearby group to form a condensed ring

Assignees

• Samsung Display Co Ltd
• Doosan Corp
• Dosan Corp

Inventors

• Kim Seul-Ong
• Kim Mi-Kyung
• Shin Dong-Woo
• Chu Chang-Woong
• Kim Tae Hyung
• Park Hocheol
• Beak Youngmi
• Eum Min-Sik
• Lee Eunjung
• Lee Chang Jun

Classifications

• H10K50/181

  Electron blocking layers · CPC title

• H10K50/121

  for assisting energy transfer, e.g. sensitization · CPC title

• H10K85/654 Primary

  comprising only nitrogen as heteroatom (H10K85/652 takes precedence) · CPC title

• H01L51/5028 Primary

  Electricity · mapped topic

• H01L51/0067

  Electricity · mapped topic