Organic electroluminescent element

Patent metadata

Field	Value
Publication number	US-2022077403-A1
Application number	US-201917417267-A
Country	US
Kind code	A1
Filing date	Dec 18, 2019
Priority date	Dec 25, 2018
Publication date	Mar 10, 2022
Grant date	—

Abstract

The present invention provides various organic electroluminescent elements using a material for a capping layer and a material for a luminous layer, in which the material for a capping layer uses an arylamine material that exhibit excellent stability and durability in the form of a thin film, especially a specific amine compound having a high refractive index and having a high absorbance within a wavelength range from 400 nm to 410 nm in the absorption spectrum at a concentration of 10−5 mol/L; and in which the material for a luminous layer uses a compound containing a heterocyclic compound that has a specific fused ring structure.

First claim

1 . An organic electroluminescent element comprising at least an anode, a hole transport layer, a luminous layer, an electron transport layer, a cathode and a capping layer in this order,
wherein the capping layer comprises an arylamine compound represented by a following general formula (1); and the luminous layer comprises either or both of a heterocyclic compound having a fused ring structure represented by a following general formula (2) and a heterocyclic compound having a fused ring structure represented by a following general formula (3),

wherein, in the formula (1),
Ar 1 , Ar 2 , Ar 3 , and Ar 4 may be the same or different from each other and represent any one selected from a substituted or unsubstituted aromatic hydrocarbon group, a substituted or unsubstituted aromatic heterocyclic group, or a substituted or unsubstituted fused polycyclic aromatic group; and
n represents an integer of 0 to 4,
wherein at least one of Ar 1 , Ar 2 , Ar 3 , and Ar 4 are a monovalent group represented by a structural formula (B) or a structural formula (B′), or has the monovalent group as a substituent,

wherein, in the formula (B),
R 1 to R 4 may be the same or different from each other and represent a linking group as a binding site, a hydrogen atom, a deuterium atom, a fluorine atom, a chlorine atom, a cyano group, a nitro group, a trimethylsilyl group, a triphenylsilyl group, a linear or branched alkyl group having 1 to 6 carbon atoms which may have a substituent group, a cycloalkyl group having 5 to 10 carbon atoms which may have a substituent group, a linear or branched alkenyl group having 2 to 6 carbon atoms which may have a substituent group, a linear or branched alkoxy group having 1 to 6 carbon atoms which may have a substituent group, a cycloalkyloxy group having 5 to 10 carbon atoms which may have a substituent group, a substituted or unsubstituted aromatic hydrocarbon group, a substituted or unsubstituted aromatic heterocyclic group, a substituted or unsubstituted fused polycyclic aromatic group, or a substituted or unsubstituted aryloxy group;
Ar 5 and Ar 6 may be the same or different from each other and represent a linking group as a binding site, a substituted or unsubstituted aromatic hydrocarbon group, a substituted or unsubstituted aromatic heterocyclic group, or a substituted or unsubstituted fused polycyclic aromatic group;
X represents a carbon atom or a nitrogen atom; and Y represents any one selected from a carbon atom, a nitrogen atom, an oxygen atom, and a sulfur atom,
however, when Y is an oxygen atom or a sulfur atom, Y has no Ar 6 ; when X and Y are nitrogen atoms, X or Y has no Ar 5 or Ar 6 ; the case when X and Y are both carbon atoms; and the case when X is a nitrogen atom and Y is an oxygen atom, and the case when X is a nitrogen atom and Y is a sulfur atom are excluded; and
with the same substituted benzene ring, R 1 to R 4 are bonded to each other, via a single bond, a substituted or unsubstituted methylene group, a substituted or unsubstituted amino group, an oxygen atom, or a sulfur atom to form a ring,

wherein, in the formula (B′),
R 3 , R 4 , and R 23 to R 26 may be the same or different from each other and represent a linking group, a hydrogen atom, a deuterium atom, a fluorine atom, a chlorine atom, a cyano group, a nitro group, a trimethylsilyl group, a triphenylsilyl group, a linear or branched alkyl group having 1 to 6 carbon atoms which may have a substituent group, a cycloalkyl group having 5 to 10 carbon atoms which may have a substituent group, a linear or branched alkenyl group having 2 to 6 carbon atoms which may have a substituent group, a linear or branched alkyloxy group having 1 to 6 carbon atoms which may have a substituent group, a cycloalkyloxy group having 5 to 10 carbon atoms which may have a substituent group, a substituted or unsubstituted aromatic hydrocarbon group, a substituted or unsubstituted aromatic heterocyclic group, a substituted or unsubstituted fused polycyclic aromatic group, or a substituted or unsubstituted aryloxy group;
Ar 5 and Ar 6 may be the same or different from each other and represent a linking group as a binding site, a substituted or unsubstituted aromatic hydrocarbon group, a substituted or unsubstituted aromatic heterocyclic group, or a substituted or unsubstituted fused polycyclic aromatic group;
X represents a carbon atom or a nitrogen atom; and Y represents any one selected from a carbon atom, a nitrogen atom, an oxygen atom, and a sulfur atom, and
however, when Y is an oxygen atom or a sulfur atom, Y has no Ar 6 ; and when X and Y are nitrogen atoms, X or Y has no Ar 5 or Ar 6 ; the case when X and Y are carbon atoms; and the case when X is a nitrogen atom and Y is an oxygen atom, and the case when X is a nitrogen atom and Y is a sulfur atom are excluded; and
with the same substituted benzene ring, R 3 , R 4 and R 23 to R 26 may be bonded to each other, via a single bond, a substituted or unsubstituted methylene group, a substituted or unsubstituted amino group, an oxygen atom, or a sulfur atom to form a ring,

wherein, in the formula (2),
A 1 represents a divalent group of a substituted or unsubstituted aromatic hydrocarbon, a divalent group of a substituted or unsubstituted aromatic heterocyclic ring, a divalent group of a substituted or unsubstituted fused polycyclic aromatic ring, or a single bond;
Ar 7 represents a substituted or unsubstituted aromatic hydrocarbon group, a substituted or unsubstituted aromatic heterocyclic group, or a substituted or unsubstituted fused polycyclic aromatic group;
R 5 to R 8 may be the same or different from each other and represent a hydrogen atom, a deuterium atom, a fluorine atom, a chlorine atom, a cyano group, a nitro group, a linear or branched alkyl group having 1 to 6 carbon atoms which may have a substituent, or a cycloalkyl group having 5 to 10 carbon atoms which may have a substituent group, a linear or branched alkenyl group having 2 to 6 carbon atoms which may have a substituent group, a linear or branched alkyloxy group having 1 to 6 carbon atoms which may have a substituent, a cycloalkyloxy group having 5 to 10 carbon atoms which may have a substituent, a substituted or unsubstituted aromatic hydrocarbon group, a substituted or unsubstituted aromatic heterocyclic group, a substituted or unsubstituted fused polycyclic aromatic group, a substituted or unsubstituted aryloxy group, or a disubstituted amino group substituted by a group selected from an aromatic hydrocarbon group, an aromatic heterocyclic group, and a fused polycyclic aromatic group,
wherein R 5 to R 8 may be bonded to each other via a single bond, a substituted or unsubstituted methylene group, an oxygen atom, or a sulfur atom to form a ring; and R 5 to R 8 may be bonded to the substituted benzene ring to form a ring, via a substituted or unsubstituted methylene group, an oxygen atom, a sulfur atom, or a linking group;
R 9 to R 12 may be the same or different from each other and represent a hydrogen atom, a deuterium atom, a fluorine atom, a chlorine atom, a cyano group, a nitro group, a linear or branched alkyl group having 1 to 6 carbon atoms which may have a substituent, a cycloalkyl group having 5 to 10 carbon atoms which may have a substituent, a linear or branched alkenyl group having 2 to 6 carbon ato

Assignees

• Hodogaya Chemical Co Ltd
• Sfc Co Ltd

Inventors

• HIRAYAMA Yuta
• Yamamoto Takeshi
• Mochizuki Shunji
• Hayashi Shuichi
• Lee Se-Jin
• Lee Oun-Gyu
• Shin Bong-Ki

Classifications

• H10K50/858

  comprising refractive means, e.g. lenses · CPC title

• H10K85/6572

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

• C09K11/06 Primary

  containing organic luminescent materials · CPC title

• H01L51/0061

  Electricity · mapped topic

• H01L51/0074

  Electricity · mapped topic