Organic electroluminescence device and electronic apparatus provided with the same

Patent metadata

Field	Value
Publication number	US-12284916-B2
Application number	US-202017602273-A
Country	US
Kind code	B2
Filing date	Apr 8, 2020
Priority date	Apr 8, 2019
Publication date	Apr 22, 2025
Grant date	Apr 22, 2025

Abstract

An organic electroluminescence device comprising: a cathode, an anode, and an organic layer disposed between the cathode and the anode, wherein the organic layer comprises an emitting layer and a first layer, the first layer is disposed between the cathode and the emitting layer, the emitting layer comprises a compound represented by the following formula (1), and the first layer comprises a compound represented by the following formula (BE1):

First claim

The invention claimed is:

1. An organic electroluminescence device comprising:
a cathode,
an anode, and
an organic layer disposed between the cathode and the anode, wherein
the organic layer comprises an emitting layer, a first layer, and a second layer,
the first layer is disposed between the cathode and the emitting layer,
the second layer is disposed between the cathode and the first layer,
the second layer comprises a compound represented by the following formula (EB4),
the emitting layer comprises a compound represented by the following formula (1), and
the first layer comprises a compound represented by the following formula (BE1):

wherein in the formula (1),
X 1 is an oxygen atom or a sulfur atom;
Ar 1 is a substituted or unsubstituted aryl group including 6 to 50 ring carbon atoms, or
a substituted or unsubstituted monovalent heterocyclic group including 5 to 50 ring atoms;
L 1 is a single bond,
a substituted or unsubstituted arylene group including 6 to 50 ring carbon atoms, or
a substituted or unsubstituted divalent heterocyclic group including 5 to 50 ring atoms;
R 1 to R 8 and R 11 to R 19 are independently
a hydrogen atom, a halogen atom, a cyano group, a nitro group,
a substituted or unsubstituted alkyl group including 1 to 50 carbon atoms,
a substituted or unsubstituted alkenyl group including 2 to 50 carbon atoms,
a substituted or unsubstituted alkynyl group including 2 to 50 carbon atoms,
a substituted or unsubstituted cycloalkyl group including 3 to 50 ring carbon atoms,
—Si(R 901 )(R 902 )(R 903 ),
—O—(R 904 ),
—S—(R 905 ),
—N(R 906 )(R 907 ),
a substituted or unsubstituted aryl group including 6 to 50 ring carbon atoms, or
a substituted or unsubstituted monovalent heterocyclic group including 5 to 50 ring atoms;
R 901 to R 907 are independently
a hydrogen atom,
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 aryl group including 6 to 50 ring carbon atoms, or
a substituted or unsubstituted monovalent heterocyclic group including 5 to 50 ring atoms; and
when two or more of each of R 901 to R 907 are present, the two or more of each of R 901 to R 907 are the same or different;

wherein in the formula (BE1),
two or more of X 31 to X 33 are nitrogen atoms, and the rest which is not a nitrogen atom is CR;
R is
a hydrogen atom,
a cyano 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,
—Si(R 901 )(R 902 )(R 903 ),
—O—(R 904 ),
a substituted or unsubstituted aryl group including 6 to 50 ring carbon atoms, or
a substituted or unsubstituted monovalent heterocyclic group including 5 to 50 ring atoms;
R 901 to R 904 are as defined in the formula (1);
when a plurality of R's are present, the plurality of R's may be the same as or different from each other;
AE is a substituted or unsubstituted aryl group including 6 to 50 ring carbon atoms, or a substituted or unsubstituted monovalent heterocyclic group including 5 to 50 ring atoms;
BE is a substituted or unsubstituted aryl group including 6 to 50 ring carbon atoms, or a substituted or unsubstituted monovalent heterocyclic group including 5 to 50 ring atoms;
LE is a single bond, a substituted or unsubstituted (nE+1)-valent aromatic hydrocarbon ring group including 6 to 50 ring carbon atoms, or a substituted or unsubstituted (nE+1)-valent heterocyclic group including 5 to 50 ring atoms; the aromatic hydrocarbon ring group may have a structure in which two or more different aromatic hydrocarbon rings are bonded;
CE's are independently a substituted or unsubstituted aryl group including 6 to 50 ring carbon atoms, or a substituted or unsubstituted monovalent heterocyclic group including 5 to 50 ring atoms;
nE is an integer of 1 to 3; and when nE is 2 or more, LE is not a single bond;

wherein in the formula (EB4),
ArE 1 and ArE 3 are independently
a single bond,
a substituted or unsubstituted phenylene group,
a substituted or unsubstituted naphthylene group,
a substituted or unsubstituted phenanthrylene group, or
a substituted or unsubstituted anthrylene group;
ArE 2 and ArE 4 are independently
a substituted or unsubstituted phenyl group,
a substituted or unsubstituted naphthyl group,
a substituted or unsubstituted phenanthryl group, or
a substituted or unsubstituted anthryl group;
ArE 1 and ArE 2 , and ArE 3 and ArE 4 independently form a substituted or unsubstituted, saturated or unsaturated ring constituted only by a 6-membered ring by bonding with each other, or do not form a ring.

2. The organic electroluminescence device according to claim 1 , wherein the compound represented by the formula (BE1) is a compound represented by the following formula (BE10):

wherein in the formula (BE10),
AE, BE, LE, CE, and nE are as defined in the formula (BE1).

3. The organic electroluminescence device according to claim 1 , wherein L 1 is
a single bond, or
a substituted or unsubstituted arylene group including 6 to 14 ring carbon atoms.

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

wherein in the formula (1-1), X 1 , Ar 1 , R 1 to R 8 , and R 11 to R 19 are as defined in the formula (1).

5. The organic electroluminescence device according to claim 1 , wherein Ar 1 is a substituted or unsubstituted aryl group including 6 to 50 ring carbon atoms.

6. The organic electroluminescence device according to claim 1 , wherein Ar 1 is selected from the group represented by the following formulas (al) to (a4),

wherein in the formulas (al) to (a4), “*” is bonded to a carbon atom of the anthracene skeleton;
R 21 is
a substituted or unsubstituted alkyl group including 1 to 50 carbon atoms,
a substituted or unsubstituted alkenyl group including 2 to 50 carbon atoms,
a substituted or unsubstituted alkynyl group including 2 to 50 carbon atoms,
a substituted or unsubstituted cycloalkyl group including 3 to 50 ring carbon atoms,
—Si(R 901 )(R 902 )(R 903 ),
—O—(R 904 ),
—S—(R 905 ),
—N(R 906 )(R 907 ),
a halogen atom, a cyano group, a nitro group,
a substituted or unsubstituted aryl group including 6 to 50 ring carbon atoms, or
a substituted or unsubstituted monovalent heterocyclic group including 5 to 50 ring atoms;
R 901 to R 907 are as defined

Assignees

• Idemitsu Kosan Co

Inventors

• Itoi Hiroaki
• Nakano Yuki
• TASAKI Satomi
• Yamaki Taro
• Masuda Tetsuya

Classifications

• H10K2101/10

  Triplet emission · CPC title

• H10K50/11

  characterised by the electroluminescent [EL] layers · CPC title

• H10K85/615

  Polycyclic condensed aromatic hydrocarbons, e.g. anthracene · CPC title

• C09K2211/1018

  Heterocyclic compounds · CPC title

• C09K11/06 Primary

  containing organic luminescent materials · CPC title