Organic electroluminescence device and amine compound for organic electroluminescence device

Patent metadata

Field	Value
Publication number	US-12439820-B2
Application number	US-202016997683-A
Country	US
Kind code	B2
Filing date	Aug 19, 2020
Priority date	Dec 6, 2019
Publication date	Oct 7, 2025
Grant date	Oct 7, 2025

Abstract

An organic electroluminescence device includes a first electrode and a second electrode facing each other, and a plurality of organic layers between the first electrode and the second electrode, wherein at least one of the organic layers includes an amine compound represented by Formula 1 below. The organic electroluminescence device may have improved luminous efficiency.

First claim

What is claimed is:

1. An organic electroluminescence device, comprising:
a first electrode;
a second electrode facing the first electrode; and
a plurality of organic layers between the first electrode and the second electrode,
wherein at least one organic layer of the plurality of organic layers comprises an amine compound,
the amine compound comprises an amine group and a tetraphenylethylene group substituted in the amine group,
the amine group is linked to one phenyl group contained in the tetraphenylethylene group and two other groups,
the two other groups are each independently a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group selected from the group consisting of a thiophene group, a furan group, a pyrrole group, an imidazole group, an oxadiazole group, a triazole group, a pyridine group, a bipyridine group, a pyrimidine group, a triazine group, an acridyl group, a pyridazine group, a pyrazinyl group, a quinoline group, a quinazoline group, a quinoxaline group, a phenoxazine group, a phthalazine group, a pyrido pyrimidine group, a pyrido pyrazine group, a pyrazino pyrazine group, an isoquinoline group, an indole group, a carbazole group, an N-arylcarbazole group, an N-heteroarylcarbazole group, an N-alkylcarbazole group, a benzoxazole group, a benzimidazole group, a benzothiazole group, a benzocarbazole group, a benzothiophene group, a dibenzothiophene group, a thienothiophene group, a benzofuran group, a phenanthroline group, a thiazole group, an isoxazole group, an oxazole group, an oxadiazole group, a phenothiazine group, a dibenzosilole group, and a dibenzofuran group,
wherein each substituent of the substituted aryl group is selected from the group consisting of a deuterium atom, a halogen atom, a cyano group, a nitro group, a silyl group, an oxy group, a sulfinyl group, a sulfonyl group, a carbonyl group, a boron group, a phosphine oxide group, a phosphine sulfide group, an alkyl group, an alkenyl group, an alkoxy group, a hydrocarbon ring group, an aryl group, and a heterocyclic group, the heterocyclic group being selected from the group consisting of a thiophene group, a furan group, a pyrrole group, an imidazole group, a thiazole group, an oxazole group, an oxadiazole group, a pyridine group, a bipyridine group, a pyrimidine group, a triazine group, a triazole group, an acridyl group, a pyridazine group, a pyrazinyl group, a quinoline group, a quinazoline group, a quinoxaline group, a phenoxazine group, a phthalazine group, a pyrido pyrimidine group, a pyrido pyrazine group, a pyrazino pyrazine group, an isoquinoline group, an indole group, a carbazole group, an N-arylcarbazole group, an N-heteroarylcarbazole group, an N-alkylcarbazole group, a benzoxazole group, a benzothiazole group, a benzocarbazole group, a benzothiophene group, a dibenzothiophene group, a benzofuran group, a phenanthroline group, a thiazole group, an isoxazole group, an oxazole group, an oxadiazole group, a thiadiazole group, a phenothiazine group, a dibenzosilole group, and a dibenzofuran group, and
wherein the amine compound is a monoamine compound, in which only one amine group exists in its molecular structure without forming a ring,
when one of the two other groups is an unsubstituted phenyl group, then the two other groups are different from each other, and
when the amine group is directly linked to the one phenyl group contained in the tetraphenylethylene group and one or both of the two other groups are each an unsubstituted aryl group, then the unsubstituted aryl group has 6 to 13 ring-forming carbon atoms.

2. The organic electroluminescence device of claim 1 , wherein the tetraphenylethylene group is bonded through a linker or directly to the amine group.

3. The organic electroluminescence device of claim 1 ,
wherein the plurality of organic layers comprise:
a hole transport region on the first electrode;
an emission layer on the hole transport region; and
an electron transport region on the emission layer, and

wherein the hole transport region comprises the amine compound.

4. The organic electroluminescence device of claim 3 ,
wherein the hole transport region comprises:
a hole injection layer on the first electrode; and
a hole transport layer on the hole injection layer, and

wherein the hole transport layer comprises the amine compound.

5. The organic electroluminescence device of claim 3 , wherein the hole transport region comprises a plurality of organic layers, and
an organic layer adjacent to the emission layer from among the plurality of organic layers comprised in the hole transport region comprises the amine compound.

6. An organic electroluminescence device, comprising:
a first electrode;
a second electrode facing the first electrode; and
a plurality of organic layers between the first electrode and the second electrode,
wherein at least one organic layer of the plurality of organic layers comprises an amine compound represented by Formula 1:

wherein in Formula 1,
Ar 1 and Ar 2 are each independently a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group selected from the group consisting of a thiophene group, a furan group, a pyrrole group, an imidazole group, an oxadiazole group, a triazole group, a pyridine group, a bipyridine group, a pyrimidine group, a triazine group, an acridyl group, a pyridazine group, a pyrazinyl group, a quinoline group, a quinazoline group, a quinoxaline group, a phenoxazine group, a phthalazine group, a pyrido pyrimidine group, a pyrido pyrazine group, a pyrazino pyrazine group, an isoquinoline group, an indole group, a carbazole group, an N-arylcarbazole group, an N-heteroarylcarbazole group, an N-alkylcarbazole group, a benzoxazole group, a benzimidazole group, a benzothiazole group, a benzocarbazole group, a benzothiophene group, a dibenzothiophene group, a thienothiophene group, a benzofuran group, a phenanthroline group, a thiazole group, an isoxazole group, an oxazole group, an oxadiazole group, a phenothiazine group, a dibenzosilole group, and a dibenzofuran group, and
wherein each substituent of the substituted aryl group is selected from the group consisting of a deuterium atom, a halogen atom, a cyano group, a nitro group, a silyl group, an oxy group, a sulfinyl group, a sulfonyl group, a carbonyl group, a boron group, a phosphine oxide group, a phosphine sulfide group, an alkyl group, an alkenyl group, an alkoxy group, a hydrocarbon ring group, an aryl group, and a heterocyclic group, the heterocyclic group being selected from the group consisting of a thiophene group, a furan group, a pyrrole group, an imidazole group, a thiazole group, an oxazole group, an oxadiazole group, a pyridine group, a bipyridine group, a pyrimidine group, a triazine group, a triazole group, an acridyl group, a pyridazine group, a pyrazinyl group, a quinoline group, a quinazoline group, a quinoxaline group, a phenoxazine group, a phthalazine group, a pyrido pyrimidine group, a pyrido pyrazine group, a pyrazino pyrazine group, an isoquinoline group, an indole group, a carbazole group, an N-arylcarbazole group, an N-heteroarylcarbazole group, an N-alkylcarbazole group, a benzoxazole group, a benzothiazole group, a benzocarbazole group, a benzothiophene group, a dibenzothiophene group, a benzofuran group, a phenanthroline group, a thiazole group, an isoxazole group, an oxazole group, an oxadiazole group, a thiadiazole group, a phenothiazine group, a dibenzosilole group, and a dibenzofuran group,
L 1 is a direct linkage, a substituted or unsubstituted arylene

Assignees

• Samsung Display Co Ltd

Inventors

• Jo Sohee
• Kim Dongjun
• Kim Minji
• Jeong Eunjae
• Han Sanghyun

Classifications

• H10K50/11

  characterised by the electroluminescent [EL] layers · CPC title

• C07C211/54

  having amino groups bound to two or three six-membered aromatic rings · CPC title

• H10K85/633 Primary

  comprising polycyclic condensed aromatic hydrocarbons as substituents on the nitrogen atom · CPC title

• H10K50/15

  Hole transporting layers · CPC title

• H10K85/6572

  comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole · CPC title