Organic electroluminescence device and monoamine compound for organic electroluminescence device

Patent metadata

Field	Value
Publication number	US-11805697-B2
Application number	US-202217947056-A
Country	US
Kind code	B2
Filing date	Sep 16, 2022
Priority date	Jan 26, 2018
Publication date	Oct 31, 2023
Grant date	Oct 31, 2023

Abstract

An organic electroluminescence device includes a first electrode, a hole transport region on the first electrode, an emission layer on the hole transport region, an electron transport region on the emission layer, and a second electrode on the electron transport region. The hole transport region includes a monoamine compound represented by the following Formula 1:

First claim

What is claimed is:

1. A monoamine compound represented by Formula 1:

wherein in Formula 1,
X is S, O or CRR′,
R and R′ are each independently a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 20 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 10 ring carbon atoms, and are separate or form a ring by combining adjacent groups with each other,
L 1 is an unsubstituted phenylene group, an unsubstituted biphenylene group, or an unsubstituted heteroarylene group having 2 to 12 carbon atoms for forming a ring,
L 2 is a direct linkage, a substituted or unsubstituted arylene group having 6 to 12 ring carbon atoms, or a substituted or unsubstituted heteroarylene group having 2 to 12 ring carbon atoms,
m is an integer of 0 to 2,
n is 1 or 2,
R A is a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring carbon atoms,
q is an integer of 0 to 7,
Ar 1 is a substituted or unsubstituted aryl group having 6 to 12 ring carbon atoms, or a substituted or unsubstituted heteroaryl group selected from thiophenyl, furanyl, pyrrolyl, imidazolyl, thiazolyl, oxazolyl, oxadiazolyl, triazolyl, pyridinyl, bipyridinyl, pyrimidinyl, triazinyl, triazolyl, pyridazinyl, pyrazinyl, quinolinyl, quinazolinyl, quinoxalinyl, phenoxazinyl, phthalazinyl, pyridopyrimidinyl, pyridopyrazinyl, pyrazinopyrazinyl, isoquinolinyl, indolyl, carbazolyl, N-aryl carbazolyl, N-heteroaryl carbazolyl, N-alkyl carbazolyl, benzoxazolyl, benzimidazoyl, benzothiazolyl, dibenzothiophenyl, thienothiophenyl, phenanthrolinyl, thiazolyl, isoxazolyl, oxadiazolyl, thiadiazolyl, and phenothiazinyl, provided that when X is CRR′, Ar 1 does not comprise a heteroaryl group, and
FR is represented by one of the following:

wherein R 1 is a hydrogen atom, a deuterium atom, or a halogen atom, and b is an integer of 0 to 6.

2. The monoamine compound as claimed in claim 1 , wherein n is 1, and L 1 is an unsubstituted phenylene group, an unsubstituted biphenylene group.

3. The monoamine compound as claimed in claim 2 , wherein L 1 is an unsubstituted phenylene group.

4. The monoamine compound as claimed in claim 3 , wherein FR is substituted on the phenylene group at a para position to the amine nitrogen atom.

5. The monoamine compound as claimed in claim 3 , wherein FR is substituted on the phenylene group at a meta position to the amine nitrogen atom.

6. The monoamine compound as claimed in claim 3 , wherein FR is substituted on the phenylene group at an ortho position to the amine nitrogen atom.

7. The monoamine compound as claimed in claim 1 , wherein m is 1, L 2 is a substituted or unsubstituted arylene group having 6 to 12 ring carbon atoms, and Ar 1 is a substituted or unsubstituted aryl group having 6 to 12 ring carbon atoms.

8. The monoamine compound as claimed in claim 7 , wherein L 2 is a substituted or unsubstituted phenylene group, and Ar 1 is a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, or a substituted or unsubstituted naphthyl group.

9. The monoamine compound as claimed in claim 1 , wherein m is 0, and Ar 1 is a substituted or unsubstituted heteroaryl group selected from pyridinyl, bipyridinyl, quinolinyl, quinazolinyl, quinoxalinyl, phenoxazinyl, phthalazinyl, pyridopyrimidinyl, pyridopyrazinyl, pyrazinopyrazinyl, isoquinolinyl, indolyl, carbazolyl, N-aryl carbazolyl, N-heteroaryl carbazolyl, N-alkyl carbazolyl, benzoxazolyl, benzimidazoyl, benzothiazolyl, dibenzothiophenyl, thienothiophenyl, phenanthrolinyl, and phenothiazinyl.

10. The monoamine compound as claimed in claim 9 , wherein Ar 1 is a substituted or unsubstituted dibenzothiophene group.

11. The monoamine compound as claimed in claim 1 , wherein the monoamine compound represented by Formula 1 is selected from Compound Group 1:

12. An organic electroluminescence device, comprising:
a first electrode;
a hole transport region on the first electrode;
an emission layer on the hole transport region;
an electron transport region on the emission layer; and
a second electrode on the electron transport region,
wherein the hole transport region comprises a monoamine compound represented by Formula 1:

wherein in Formula 1,
X is CRR′,
R and R′ a

Assignees

• Samsung Display Co Ltd

Inventors

• Miyake Hideo
• Ueno Masatsugu
• Jin Xiulan
• Takada Ichinori
• Uno Takuya
• Itoi Hiroaki

Classifications

• H10K50/181

  Electron blocking layers · CPC title

• H10K85/636 Primary

  comprising heteroaromatic hydrocarbons as substituents on the nitrogen atom · CPC title

• C07D311/96 Primary

  spiro-condensed with carbocyclic rings or ring systems · CPC title

• C07D409/12

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

• C07D333/76

  Dibenzothiophenes · CPC title