Organic electroluminescence device

Patent metadata

Field	Value
Publication number	US-9203043-B2
Application number	US-201313902355-A
Country	US
Kind code	B2
Filing date	May 24, 2013
Priority date	May 28, 2012
Publication date	Dec 1, 2015
Grant date	Dec 1, 2015

Abstract

An organic electroluminescence device 1 includes: an anode 3, a cathode 4 opposed to the anode 3 and an emitting layer 5 provided between the anode 3 and the cathode 4. The emitting layer 5 contains first and second host materials and a luminescent material. The first host material has a partial structure represented by at least one of the following formulae (1) and (2) while the second host material has a partial structure represented by the following formula (3). Az represents a substituted or unsubstituted aromatic heterocyclic group containing a nitrogen-containing six-membered ring. WCN is an aromatic hydrocarbon group substituted by at least one cyano group (CN) or an aromatic heterocyclic group substituted by at least one cyano group (CN). Ar1 is a substituted or unsubstituted aromatic hydrocarbon group or a substituted or unsubstituted aromatic heterocyclic group, but is not an aromatic heterocyclic group containing a nitrogen-containing six-membered ring. —Az—(WCN)p  (1) —Az—(CN)q  (2) —Ar1—(CN)r  (3)

First claim

What is claimed is:

1. An organic electroluminescence device comprising:
an anode;
a cathode opposed to the anode; and
an emitting layer provided between the anode and the cathode, wherein
the emitting layer comprises a first host material, a second host material and a luminescent material,
the first host material comprises a partial structure represented by at least one of the following formulae (1) and (2), and
the second host material comprises a partial structure represented by the following formula (3) and does not comprise a partial structure represented by the formula (1) or the formula (2),
-Az-(W CN ) p   (1)

-Az-(CN) q   (2)

—Ar 1 —(CN) r   (3)

where: in the formula (1),
Az represents a substituted or unsubstituted aromatic heterocyclic group comprising a nitrogen-containing six-membered ring,
W CN is an aromatic hydrocarbon group substituted by at least one cyano group (CN) or an aromatic heterocyclic group substituted by at least one cyano group (CN),
p is an integer of 1 or more, and
W CN optionally comprises a substituent other than the cyano group and, when a plurality of W CN are present, the plurality of W CN are mutually the same or different;
In the formula (2),
Az represents the same as Az of the formula (1), and
q is an integer of 1 or more; and
in the formula (3),
Ar 1 is a substituted or unsubstituted aromatic hydrocarbon group or a substituted or unsubstituted aromatic heterocyclic group, but is not an aromatic heterocyclic group comprising a nitrogen-containing six-membered ring, and
r is an integer of 1 or more.

2. The organic electroluminescence device according to claim 1 , wherein
the first host material is represented by at least one of the formulae (1-1) and (2-1), and
the second host material is represented by the following formula (3-1),
Ar 2 -Az-(W CN ) p   (1-1)

Ar 2 -Az-(CN) q   (2-1)

Ar 3 —Ar 1 —(CN) r   (3-1)

where:
Ar 2 and Ar 3 each independently represent a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted aromatic heterocyclic group having 5 to 30 ring atoms,
Az, W CN and p in the formula (1-1) are the same as Az, W CN and p in the formula (1),
Az and q in the formula (2-1) are the same as Az and q in the formula (2), and
Ar 1 and r in the formula (3-1) are the same as Ar 1 and r in the formula (3).

3. The organic electroluminescence device according to claim 1 , wherein
the first host material is represented by the following formula (4),

where:
M 1 represents a group represented by one of the formulae (1) and (2),
L 1 represents a single bond, a substituted or unsubstituted polyvalent aromatic hydrocarbon group having 6 to 30 ring carbon atoms, a substituted or unsubstituted polyvalent aromatic heterocyclic group having 5 to 30 ring atoms, a cycloalkylene group having 5 to 30 ring carbon atoms, or a group provided by linking the polyvalent aromatic hydrocarbon group, the polyvalent aromatic heterocyclic group and the cycloalkylene group,
k is 1 or 2,
X 11 to X 18 each independently represent a nitrogen atom or CR b ,
R b each independently represents a hydrogen atom, a halogen atom, a cyano group, a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 ring carbon atoms, a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 30 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 30 ring carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, a substituted or unsubstituted aralkyl group having 6 to 30 ring carbon atoms, and a substituted or unsubstituted aryloxy group having 6 to 30 ring carbon atoms, and
a part of one of adjacent two R b in X 11 to X 18 is optionally bonded to a part of the other R b to form a cyclic structure.

4. The organic electroluminescence device according to claim 1 , wherein
the second host material is represented by the following formula (5),

where:
A 1 represents a group represented by the formula (3),
X 1 to X 8 each independently represent N (nitrogen atom) or CR a ,
R a each independently represents a hydrogen atom, a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 ring carbon atoms, a substituted or unsubstituted aromatic heterocyclic group having 5 to 30 ring atoms, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted silyl group, a halogen atom, or a cyano group, when a plurality of R a are present, the plurality of R a are the same or different, and
when at least adjacent two of X 1 to X 4 and X 5 to X 8 are CR a , a part of R a in the adjacent CR a is optionally bonded to a part of the other R a to form a cyclic structure.

5. The organic electroluminescence device according to claim 3 , wherein
the first host material is represented by at least one of the following formulae (4-3) and (4-4),

where:
L 1 and X 11 to X 18 are the same as L 1 and X 11 to X 18 in the formula (4),
Az, W CN and p in the formula (4-3) are the same as Az, W CN and p in the formula (1), and
Az and q in the formula (4-4) are the same as Az and q in the formula (1).

6. The organic electroluminescence device according to claim 4 , wherein
the first host material is represented by at least one of the following formulae (4-3) and (4-4),

where:
L 1 represents a single bond, a substituted or unsubstituted polyvalent aromatic hydrocarbon group having 6 to 30 ring carbon atoms, a substituted or unsubstituted polyvalent aromatic heterocyclic group having 5 to 30 ring atoms, a cycloalkylene group having 5 to 30 ring carbon atoms, or a group provided by linking the polyvalent aromatic hydrocarbon group, the polyvalent aromatic heterocyclic group and the cycloalkylene group,
X 11 to X 18 each independently represent a nitrogen atom or CR b ,
R b each independently represents a hydrogen atom, a halogen atom, a cyano group, a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 ring carbon atoms, a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 30 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 30 ring carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, a substituted or unsubstituted aralkyl group having 6 to 30 ring carbon atoms, and a substituted or unsubstituted aryloxy group having 6 to 30 ring carbon atoms, and
a part of one of adjacent two R b in X 11 to X 18 is optionally bonded to a part of the other R b to form a cyclic structure,
Az, W CN and p in the formula (4-3) are the same as Az, W CN and p in the formula (1), and
Az and q in the formula (4-4) are the same as Az

Assignees

• Nishimura Kazuki
• Inoue Tetsuya
• Mizuki Yumiko
• Yabunouchi Nobuhiro
• Eida Mitsuru
• Idemitsu Kosan Co

Inventors

• Nishimura Kazuki
• Inoue Tetsuya
• Mizuki Yumiko
• Yabunouchi Nobuhiro
• Eida Mitsuru

Classifications

• H01L51/5016

  Electricity · mapped topic

• C09K2211/185

  of the platinum group, i.e. Os, Ir, Pt, Ru, Rh or Pd · CPC title

• H01L51/0072

  Electricity · mapped topic

• H01L51/5044

  Electricity · mapped topic

• H01L2251/308

  Electricity · mapped topic