IP Library Granted Patent US 12,588,355
Granted Patent B2
US 12,588,355 · App. 17/815,173 · Granted Mar 24, 2026

Organic light-emitting element, display apparatus, photoelectric conversion apparatus, electronic equipment, lighting apparatus, moving body, and exposure light source

Inventors: Hironobu Iwawaki (Kanagawa, JP); Jun Kamatani (Tokyo, JP); Naoki Yamada (Tokyo, JP); Yosuke Nishide (Kanagawa, JP); Hirokazu Miyashita (Kanagawa, JP)
Assignee: Canon Kabushiki Kaisha
H10K50/12C07F15/0033H10K50/11H10K59/38H10K59/60H10K59/65H10K85/342H10K85/361H10K85/615H10K85/622H10K85/654H10K85/6572H10K85/6574H10K85/6576C07B2200/05H10K2101/40
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Quick Facts
Patent No.
US 12,588,355
App. No.
17/815,173
Granted
Mar 24, 2026
Kind
B2
Abstract

A organic light-emitting element including a positive electrode, a light-emitting layer, and a negative electrode in this order, wherein the light-emitting layer contains a dopant material, a host material, and an assist material, the dopant material is a compound represented by the following general formula [1], the host material is a hydrocarbon compound, and the assist material has a lower LUMO level than the host material. In the formula [1], R 1 to R 10 denote a hydrogen atom, an alkyl group, or the like. X denotes O or S. m denotes an integer in the range of 1 to 3, and n denotes an integer in the range of 0 to 2, provided that m+n is 3. The partial structure IrL n is any one of structures represented by the following formulae [2] and [3], wherein R 11 to R 21 denote a hydrogen atom, an alkyl group, or the like.

Claims (60)

1 . An organic light-emitting element comprising:

a positive electrode, a light-emitting layer, and a negative electrode in this order,

wherein the light-emitting layer contains a dopant material, a host material, and an assist material,

the dopant material is a compound represented by the following general formula [1],

the host material is an aromatic hydrocarbon compound, and

the assist material has a lower LUMO level than the host material (farther from the vacuum level),

wherein R 1 to R 10 independently denote a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted amino group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heterocyclic group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted heteroaryloxy group, a substituted or unsubstituted silyl group, or a cyano group,

X denotes O or S,

m denotes an integer in the range of 1 to 3, and n denotes an integer in the range of 0 to 2, provided that m+n is 3, and

the partial structure IrL n is any one of structures represented by the following general formulae [2] and [3],

wherein R 11 to R 21 independently denote a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted amino group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heterocyclic group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted heteroaryloxy group, a substituted or unsubstituted silyl group, or a cyano group, and

wherein the organic light-emitting element emits yellow light.

2 . The organic light-emitting element according to claim 1 , wherein the assist material is a compound partially having any one of the following structures:

wherein X denotes an oxygen atom, a sulfur atom, or a substituted or unsubstituted carbon atom.

3 . The organic light-emitting element according to claim 1 , wherein the host material has at least one of a triphenylene ring, a phenanthrene ring, a chrysene ring, and a fluoranthene ring as a backbone.

4 . The organic light-emitting element according to claim 1 , wherein at least one of R 1 to R 21 denotes an alkyl group having 1 to 4 carbon atoms.

5 . The organic light-emitting element according to claim 1 , wherein the organic light-emitting element emits green light.

6 . The organic light-emitting element according to claim 1 , further comprising another light-emitting layer on the light-emitting layer, wherein the other light-emitting layer emits light of a different emission color from the light-emitting layer.

7 . The organic light-emitting element according to claim 6 , wherein the organic light-emitting element emits white light.

8 . A display apparatus comprising a plurality of pixels, wherein at least one of the plurality of pixels includes the organic light-emitting element according to claim 1 and an active element coupled to the organic light-emitting element.

9 . The display apparatus according to claim 8 , further comprising a color filter.

10 . A photoelectric conversion apparatus comprising:

an optical unit with a plurality of lenses;

an imaging element configured to receive light passing through the optical unit; and

a display unit configured to display an image taken by the imaging element,

wherein the display unit includes the organic light-emitting element according to claim 1 .

11 . Electronic equipment comprising:

a display unit including the organic light-emitting element according to claim 1 ;

a housing in which the display unit is provided; and

a communication unit configured to communicate with an outside provided in the housing.

12 . A lighting apparatus comprising:

a light source including the organic light-emitting element according to claim 1 ; and

a light-diffusing unit or an optical filter that transmits light emitted by the light source.

13 . A moving body comprising:

a lamp including the organic light-emitting element according to claim 1 ; and

a body to which the lamp is provided.

14 . An exposure light source of an electrophotographic image-forming apparatus, comprising the organic light-emitting element according to claim 1 .

15 . An organic light-emitting element comprising:

a positive electrode, a light-emitting layer, and a negative electrode in this order,

wherein the light-emitting layer contains a dopant material, a host material, and an assist material,

the dopant material is a compound represented by the following general formula [1],

the host material is an aromatic hydrocarbon compound, and

the assist material has a lower LUMO level than the host material (farther from the vacuum level),

wherein R 1 to R 7 , R 9 , and R 10 independently denote a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted amino group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heterocyclic group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted heteroaryloxy group, a substituted or unsubstituted silyl group, or a cyano group,

R 8 denotes a phenyl group,

X denotes O or S,

m denotes an integer in the range of 1 to 3, and n denotes an integer in the range of 0 to 2, provided that m+n is 3, and

the partial structure IrL n is any one of structures represented by the following general formulae [2] and [3],

wherein R 11 to R 21 independently denote a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted amino group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heterocyclic group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted heteroaryloxy group, a substituted or unsubstituted silyl group, or a cyano group.

16 . An organic light-emitting element comprising:

a positive electrode, a light-emitting layer, and a negative electrode in this order,

wherein the light-emitting layer contains a dopant material, a host material, and an assist material,

wherein the dopant material is any one of the following compounds,

the host material is an aromatic hydrocarbon compound, and

the assist material has a lower LUMO level than the host material (farther from the vacuum level),

wherein R 1 to R 10 independently denote a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted amino group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heterocyclic group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted heteroaryloxy group, a substituted or unsubstituted silyl group, or a cyano group,

X denotes O or S,

m denotes an integer in the range of 1 to 3, and n denotes an integer in the range of 0 to 2, provided that m+n is 3, and

the partial structure IrL n is any one of structures represented by the following general formulae [2] and [3],

wherein R 11 to R 21 independently denote a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted amino group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heterocyclic group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted heteroaryloxy group, a substituted or unsubstituted silyl group, or a cyano group.

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Sep 9, 2022
From: IWAWAKI, HIRONOBU; KAMATANI, JUN; YAMADA, NAOKI; NISHIDE, YOSUKE; MIYASHITA, HIROKAZU
To: CANON KABUSHIKI KAISHA
Reel/Frame 061037/0140 →
Priority Claims (1)
JP 2021-124118 · Jul 29, 2021 · national
Continuity (1)
Related Publication 20230093269A1 · Mar 23, 2023
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