Organic electroluminecence device

Patent metadata

Field	Value
Publication number	US-10435350-B2
Application number	US-201816141909-A
Country	US
Kind code	B2
Filing date	Sep 25, 2018
Priority date	Sep 19, 2014
Publication date	Oct 8, 2019
Grant date	Oct 8, 2019

Abstract

A compound is represented by the following formula (1). In the formula (1), Ar is a substituted or unsubstituted aryl group including 6 to 30 ring carbon atoms, R a are independently a substituted or unsubstituted alkyl group including 1 to 15 carbon atoms, or a substituted or unsubstituted cycloalkyl group including 3 to 15 carbon atoms, R b1 to R b4 are independently a halogen atom, a cyano group, a substituted or unsubstituted alkyl group including 1 to 15 carbon atoms, or the like, R c1 to R c10 are independently a hydrogen atom, a halogen atom, a cyano group, a substituted or unsubstituted alkyl group including 1 to 15 carbon atoms, or the like, * is a bonding position at which one of R c1 to R c10 is bonded to either nitrogen atom, x is an integer from 0 to 3, y is an integer from 0 to 4, and z are independently an integer from 0 to 5.

First claim

The invention claimed is:

1. An organic electroluminescence device comprising a cathode, an anode, and one or more organic thin film layers that are provided between the cathode and the anode,
wherein the one or more organic thin film layers comprises at least an emitting layer, and
at least one organic thin film layer included in the one or more organic thin film layers comprises a compound represented by a formula (1) and a compound represented by a formula (5),

wherein Ar is a substituted or unsubstituted aryl group including 6 to 30 ring carbon atoms with the proviso that Ar is not a substituted or unsubstituted fluorenyl group,
R a are independently a substituted or unsubstituted alkyl group including 1 to 15 carbon atoms, or a substituted or unsubstituted cycloalkyl group including 3 to 15 carbon atoms,
R b1 to R b4 are independently a halogen atom, a cyano group, a substituted or unsubstituted alkyl group including 1 to 15 carbon atoms, a substituted or unsubstituted cycloalkyl group including 3 to 15 carbon atoms, a substituted or unsubstituted alkylsilyl group including 1 to 45 carbon atoms, a substituted or unsubstituted arylsilyl group including 6 to 50 carbon atoms, a substituted or unsubstituted alkoxy group including 1 to 15 carbon atoms, a substituted or unsubstituted aryloxy group including 6 to 30 ring carbon atoms, a substituted or unsubstituted alkylthio group including 1 to 15 carbon atoms, a substituted or unsubstituted arylthio group including 6 to 30 ring carbon atoms, a substituted or unsubstituted arylamino group including 6 to 30 ring carbon atoms, a substituted or unsubstituted aryl group including 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group including 3 to 30 ring atoms,
R c1 to R c10 are independently a hydrogen atom, a halogen atom, a cyano group, a substituted or unsubstituted alkyl group including 1 to 15 carbon atoms,
a substituted or unsubstituted cycloalkyl group including 3 to 15 carbon atoms,
a substituted or unsubstituted alkylsilyl group including 1 to 45 carbon atoms,
a substituted or unsubstituted arylsilyl group including 6 to 50 carbon atoms,
a substituted or unsubstituted alkoxy group including 1 to 15 carbon atoms,
a substituted or unsubstituted aryloxy group including 6 to 30 ring carbon atoms,
a substituted or unsubstituted alkylthio group including 1 to 15 carbon atoms,
a substituted or unsubstituted arylthio group including 6 to 30 ring carbon atoms,
a substituted or unsubstituted arylamino group including 6 to 30 ring carbon atoms, a substituted or unsubstituted aryl group including 6 to 30 ring carbon atoms,
a substituted or unsubstituted heteroaryl group including 3 to 30 ring atoms, or
a single bond that is bonded to either nitrogen atom,
* is a bonding position at which any of R c1 to R c10 is bonded to either nitrogen atom,
x is an integer from 0 to 3,
y is an integer from 0 to 4,
z is independently an integer from 0 to 5,
a plurality of R b1 are either identical or different when x is an integer equal to or larger than 2, a plurality of R b2 are either identical or different when y is an integer equal to or larger than 2, and a plurality of R b3 or R b4 are either identical or different when z is an integer equal to or larger than 2,
when R a is substituted with a substituent, the substituent is an alkyl group including 1 to 10 carbon atoms, a cycloalkyl group including 3 to 10 ring carbon atoms, an alkylsilyl group including 3 to 30 carbon atoms, an arylsilyl group including 6 to 60 carbon atoms, an alkoxy group including 1 to 10 carbon atoms, an aryloxy group including 6 to 20 ring carbon atoms, an alkylthio group including 1 to 10 carbon atoms, an arylthiol group including 6 to 20 ring carbon atoms, an arylamino group including 12 to 30 ring carbon atoms, an aryl group including 6 to 20 ring carbon atoms, or a heteroaryl group including 5 to 20 ring atoms,

wherein Ar 11 is a substituted or unsubstituted monocyclic group including 5 to 50 ring atoms, or a substituted or unsubstituted fused aromatic ring group including 8 to 50 ring atoms,
Ar 12 is a substituted or unsubstituted fused heterocyclic ring group including 8 to 50 ring atoms, a monocyclic group including 5 to 50 ring atoms substituted with a substituted or unsubstituted fused heterocyclic ring group including 8 to 50 ring atoms, or a fused aromatic ring group including 8 to 50 ring atoms substituted with a substituted or unsubstituted fused heterocyclic ring group including 8 to 50 ring atoms, and
R 101 to R 108 are independently an atom or a group selected from a group consisting of a hydrogen atom,
a substituted or unsubstituted monocyclic group including 5 to 50 ring atoms,
a substituted or unsubstituted fused ring group including 8 to 50 ring atoms,
a group formed by a combination of the monocyclic group and the fused ring group,
a substituted or unsubstituted alkyl group including 1 to 50 carbon atoms,
a substituted or unsubstituted cycloalkyl group including 3 to 50 ring carbon atoms,
a substituted or unsubstituted alkoxy group including 1 to 50 carbon atoms,
a substituted or unsubstituted aralkyl group including 7 to 50 carbon atoms,
a substituted or unsubstituted aryloxy group including 6 to 50 ring carbon atoms,
a substituted or unsubstituted silyl group, a halogen atom, and a cyano group.

2. The organic electroluminescence device according to claim 1 , wherein the compound represented by the formula (1) is a compound represented by a formula (2),

wherein Ar, R a , R b1 to R b4 , R c1 to R c10 , x, z, and * are the same as defined for the formula (1).

3. The organic electroluminescence device according to claim 1 , wherein in the formula (1), R c1 to R c10 are independently a hydrogen atom, a halogen atom, a cyano group,
a substituted or unsubstituted alkyl group including 1 to 15 carbon atoms,
a substituted or unsubstituted cycloalkyl group including 3 to 15 carbon atoms,
a substituted or unsubstituted alkylsilyl group including 1 to 45 carbon atoms,
a substituted or unsubstituted arylsilyl group including 6 to 50 carbon atoms,
a substituted or unsubstituted alkoxy group including 1 to 15 carbon atoms,
a substituted or unsubstituted aryloxy group including 6 to 30 ring carbon atoms,
a substituted or unsubstituted alkylthio group including 1 to 15 carbon atoms,
a substituted or unsubstituted arylthio group including 6 to 30 ring carbon atoms,
a substituted or unsubstituted aryl group including 6 to 30 ring carbon atoms,
a substituted or unsubstituted heteroaryl group including 3 to 30 ring atoms, or
a single bond that is bonded to either nitrogen atom.

4. The organic electroluminescence device according to claim 1 , wherein the compound represented by the formula (1) is a compound represented by a formula (3),

wherein Ar, R a , R b1 to R b4 , R c2 to R c10 , x, z, and * are the same as defined for the formula (1).

5. The organic electroluminescence device according to claim 1 , wherein the compound represented by the formula (1) is a compound represented by a formula (4),

Assignees

• Idemitsu Kosan Co

Inventors

• Ito Hirokatsu
• Kawamura Masahiro
• Mizuki Yumiko
• Haketa Tasuku
• HAYAMA Tomoharu
• Takahashi Ryota

Classifications

• C07C2603/50

  Pyrenes; Hydrogenated pyrenes · CPC title

• C09K2211/1014

  bridged by heteroatoms, e.g. N, P, Si or B · CPC title

• C09K11/06

  containing organic luminescent materials · CPC title

• C09K2211/1007

  Non-condensed systems · CPC title

• C07C255/50

  to carbon atoms of non-condensed six-membered aromatic rings · CPC title