Organic light-emitting device and method of manufacturing the same

Patent metadata

Field	Value
Publication number	US-11696458-B2
Application number	US-201816197710-A
Country	US
Kind code	B2
Filing date	Nov 21, 2018
Priority date	Nov 24, 2017
Publication date	Jul 4, 2023
Grant date	Jul 4, 2023

Abstract

An organic light-emitting device including a first electrode, a second electrode, an emission layer disposed between the first electrode and the second electrode, a hole transport region disposed between the first electrode and the emission layer, and an electron transport region disposed between the emission layer and the second electrode, wherein the emission layer includes a host and a dopant, wherein the dopant is an iridium-free organometallic compound, and wherein a dopant concentration profile of the emission layer satisfies predetermined parameters disclosed in the specification.

First claim

What is claimed is:

1. An organic light-emitting device comprising:
a first electrode;
a second electrode;
an emission layer comprising a host and a dopant, the emission layer disposed between the first electrode and the second electrode;
a hole transport region disposed between the first electrode and the emission layer; and
an electron transport region disposed between the emission layer and the second electrode,
wherein the dopant comprises platinum or palladium, and a tetradentate organic ligand including a benzimidazole and a pyridine group, a dopant concentration profile of the emission layer satisfies N 1 ≤D con (x)≤N 2 in a direction from the hole transport region toward the electron transport region,
wherein the dopant concentration profile of the emission layer is continuous,
x of D con (x) is a real number and a variable satisfying 0≤x≤L EML ,
L EML is a thickness of the emission layer,
D con (x) represents a dopant concentration (percent by weight) in the emission layer at a distance x from an interface between the hole transport region and the emission layer to an interface between the electron transport region and the emission layer,
N 1 is a minimum value of a dopant concentration of the emission layer and is in a range of about 1 percent by weight to about 10 percent by weight,
N 2 is a maximum value of the dopant concentration of the emission layer and is greater than about 10 percent by weight and less than or equal to about 40 percent by weight,
wherein D con (0) and D con (L EML ) are each N 2 ,
wherein the dopant is represented by Formula 1A-1:

wherein in Formula 1A-1,
M represents the palladium or the platinum,
X 1 is O or S, and a bond between X 1 and M is a covalent bond, X 2 is N, and X 3 is C,
X 11 is N or C-[(L 11 ) b11 -(R 11 ) c11 ], X 12 is N or C-[(L 12 ) b12 -(R 12 ) c12 ], X 13 is N or C-[(L 13 ) b13 -(R 13 ) c13 ], and X 14 is N or C-[(L 14 ) b14 -(R 14 ) c14 ],
X 21 is N or C-[(L 21 ) b21 -(R 21 ) c21 ], X 22 is N or C-[(L 22 ) b22 -(R 22 ) c22 ], and X 23 is N or C-[(L 23 ) b23 -(R 23 ) c23 ],
X 31 is N or C-[(L 31 ) b31 -(R 31 ) c31 ], X 32 is N or C-[(L 32 ) b32 -(R 32 ) c32 ], and X 33 is N or C-[(L 33 ) b33 -(R 33 ) c33 ],
X 41 is N or C-[(L 41 ) b41 -(R 41 ) c41 ], X 42 is N or C-[(L 42 ) b42 -(R 42 ) c42 ], X 43 is N or C-[(L 43 ) b43 -(R 43 ) c43 ], and X 44 is N or C-[(L 44 ) b44 -(R 44 ) c44 ], and X 51 is N-[(L 7 ) b7 -(R 7 ) c7 ], wherein
L 7 , L 11 to L 14 , L 21 to L 23 , L 31 to L 33 , and L 41 to L 44 , are independently a substituted or unsubstituted C 5 -C 30 carbocyclic group, or a substituted or unsubstituted C 1 -C 30 heterocyclic group,
b11 to b14, b21 to b23, b31 to b33, and b41 to b44, are independently an integer of 0 to 5, and b 7 is 0,
R 7 is a substituted or unsubstituted C 3 -C 10 cycloalkyl group, a substituted or unsubstituted C 1 -C 10 heterocycloalkyl group, a substituted or unsubstituted C 6 -C 60 aryl group, a substituted or unsubstituted C 1 -C 60 heteroaryl group, or a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group,
R 11 to R 14 , R 21 to R 23 , R 31 to R 33 , and R 41 to R 44 , are independently hydrogen, deuterium, —F, a hydroxyl group, a cyano group, a nitro group, an amidino group, a substituted or unsubstituted C 1 -C 60 alkyl group, a substituted or unsubstituted C 1 -C 60 alkoxy group, a substituted or unsubstituted C 6 -C 60 aryl group, a substituted or unsubstituted C 1 -C 60 heteroaryl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, or a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group,
c7 is 1, and c11 to c14, c21 to c23, c31 to c33, and c41 to c44, are independently an integer of 1 to 5, and
optionally, at least two of R 11 to R 14 are linked to form a substituted or unsubstituted C 5 -C 30 carbocyclic group or a substituted or unsubstituted C 1 -C 30 heterocyclic group,
optionally, at least two of R 21 to R 23 are linked to form a substituted or unsubstituted C 5 -C 30 carbocyclic group or a substituted or unsubstituted C 1 -C 30 heterocyclic group,
optionally, at least two of R 31 to R 33 are linked to form a substituted or unsubstituted C 5 -C 30 carbocyclic group or a substituted or unsubstituted C 1 -C 30 heterocyclic group, or
optionally, at least two of R 41 to R 44 are linked to form a substituted or unsubstituted C 5 -C 30 carbocyclic group or a substituted or unsubstituted C 1 -C 30 heterocyclic group.

2. An organic light-emitting device comprising:
a first electrode;
a second electrode;
an emission layer comprising a host and a dopant, the emission layer disposed between the first electrode and the second electrode;
a hole transport region disposed between the first electrode and the emission layer; and
an electron transport region disposed between the emission layer and the second electrode,
a dopant concentration profile of the emission layer satisfies N 1 ≤D con (x)≤N 2 in a direction from the hole transport region toward the electron transport region, wherein
the dopant concentration profile of the emission layer is continuous,
x of D con (x) is a real number and a variable satisfying 0≤x≤L EML ,
L EML is a thickness of the emission layer,
D con (x) represents a dopant concentration (percent by weight) in the emission layer at a distance x from an interface between the hole transport region and the emission layer to an interface between the electron transport region and the emission layer,
N 1 is a minimum value of a dopant concentration of the emission layer and is in a range of about 1 percent by weight to about 10 percent by weight,
N 2 is a maximum value of the dopant concentration of the emission layer and is greater than about 10 percent by weight and less than or equal to about 40 percent by weight,
wherein
D con (0) and D con (L EML ) are each N 2 ,
wherein the dopant is represented by one or more of the following:

Assignees

• Samsung Electronics Co Ltd

Inventors

• Hong Seokhwan
• Kwak Seungyeon
• Koo Hyun
• Kim Sangdong
• Kim Sungjun
• Kim Jiwhan
• Lee Sunghun
• Aratani Sukekazu
• Lee Sunyoung
• Ishihara Shingo
• Jeon Aram
• Choi Byoungki

Classifications

• H10K71/00

  Manufacture or treatment specially adapted for the organic devices covered by this subclass · CPC title

• H10K50/11 Primary

  characterised by the electroluminescent [EL] layers · CPC title

• C09K11/06 Primary

  containing organic luminescent materials · CPC title

• H10K2101/90

  Multiple hosts in the emissive layer · CPC title

• H10K85/346

  comprising platinum · CPC title