Organic electroluminescent element

Patent metadata

Field	Value
Publication number	US-9882144-B2
Application number	US-201314655612-A
Country	US
Kind code	B2
Filing date	Dec 27, 2013
Priority date	Dec 28, 2012
Publication date	Jan 30, 2018
Grant date	Jan 30, 2018

Abstract

An organic electroluminescence device includes: an anode; a cathode; and an organic layer interposed between the anode and the cathode, in which the organic layer includes an emitting layer and the emitting layer includes a compound represented by a formula (1) below and a compound represented by a formula (2) below. Az 1 of the formula (1) below and Az 2 of the formula (2) below are each an azine ring. Cz of the formula (1) below and HAr of the formula (2) below are each a nitrogen-containing heterocyclic ring.

First claim

The invention claimed is:

1. An organic electroluminescence device, comprising:
an anode;
a cathode; and
a single-layer or multi-layer organic layer interposed between the anode and the cathode;
wherein:
the organic layer comprises an emitting layer;
the emitting layer comprises a compound according to formula (1) and a compound according to formula (2);
the emitting layer does not comprise a metal complex;
formula (1) is:

where:
each Cz is a group according to formula (10b):

where:
each of A and B is independently a substituted or unsubstituted cyclic structure;
when at least one of the cyclic structure A and the cyclic structure B has a plurality of substituents, adjacent ones of the substituents optionally form a ring; and
at least one of the cyclic structure A and the cyclic structure B has a partial structure according to formula (11):

L 1 is a single bond, a substituted or unsubstituted (m+1)-valent aromatic hydrocarbon group, or a substituted or unsubstituted (m+1)-valent heterocyclic group;
L 2 is a single bond, a substituted or unsubstituted (n+p)-valent aromatic hydrocarbon group, or a substituted or unsubstituted (n+p)-valent heterocyclic group;
L 3 represents a single bond, a substituted or unsubstituted (o+1)-valent aromatic hydrocarbon group, or a substituted or unsubstituted (o+1)-valent heterocyclic group;
m is an integer of 1 to 6;
n and p are each independently an integer of 1 to 6;
o is an integer of 1 to 6; and
Az 1 is a group according to formula (12);

where:
each of X 11 to X 15 is independently CR 8 or a nitrogen atom;
at least one of X 11 to X 15 is a nitrogen atom; and
adjacent ones of R 8 optionally form a ring;
formula (2) is:

where:
L 20 is a substituted or unsubstituted (a+g)-valent aromatic hydrocarbon group or a substituted or unsubstituted (a+g)-valent heterocyclic group;
L 201 is a substituted or unsubstituted divalent aromatic hydrocarbon group or a substituted or unsubstituted divalent heterocyclic group;
a is an integer of 1 to 6;
b is an integer of 1 to 6;
g is an integer of 0 to 2; and
HAr is a group derived from a structure according to formula (20);

where:
X 20 represents a single bond, an oxygen atom, a sulfur atom, a carbonyl group, NR 9 , CR 10 R 11 , SiR 12 R 13 , or GeR 14 R 15 ;
each of G and H is independently a substituted or unsubstituted cyclic structure;
when at least one of the cyclic structure G and the cyclic structure H has a plurality of substituents, adjacent ones of the substituents optionally form a ring; and
when at least one of the cyclic structure G and the cyclic structure H is a substituted or unsubstituted heterocyclic structure, the heterocyclic structure has a partial structure according to formula (20-2):

and
Az 2 is a group according to formula (2d):

where:
each of X 21 to X 26 is independently CR 16 or a nitrogen atom;
at least one of X 21 to X 26 is a nitrogen atom and b of X 21 to X 26 is a carbon atom to be bonded to L 20 or L 201 ; and
adjacent ones of R 16 optionally form a ring; and
each of R 8 to R 16 is independently a hydrogen atom, a substituted or unsubstituted aryl 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 alkylsilyl group having 3 to 30 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 60 ring carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 ring carbon atoms, a substituted or unsubstituted alkylamino group having 2 to 30 carbon atoms, a substituted or unsubstituted arylamino group having 6 to 60 ring carbon atoms, a substituted or unsubstituted alkylthio group having 1 to 30 carbon atoms, or a substituted or unsubstituted arylthio group having 6 to 30 ring carbon atoms.

2. The organic electroluminescence device according to claim 1 , wherein
the compound according to formula (1) is a compound according to formula (13):

where:
X 1 is a single bond;
the cyclic structure A and the cyclic structure B are as defined in formula (10b);
L 2 is as defined in formula (1); and
X 1 to X 15 are as defined in formula (12).

3. The organic electroluminescence device according to claim 1 , wherein
each of the cyclic structure A and the cyclic structure B of formula (10b) is a six-membered ring having the partial structure according to formula (11).

4. The organic electroluminescence device according to claim 1 , wherein L 2 has a divalent six-membered ring structure according to formula (3):

where:
each of X 31 to X 34 is independently CR 51 ; and
each R 51 is independently as R 8 to R 16 are defined.

5. The organic electroluminescence device according to claim 1 , wherein HAr of formula (2) is a group derived from a structure according to formula (2B):

where:
X 2 is the same as X 20 of formula (20);
each of R 61 to R 62 is independently as R 8 to R 16 are defined;
i and j are 4;
E is a cyclic structure according to formula (2h);
F is a cyclic structure according to formula (2i) or (2j);
each of the cyclic structure E and the cyclic structure F is fused to an adjacent cyclic structure at any position;
h is 0 or 1;

in formula (2h), when R 63 and R 64 are substituents at adjacent positions, R 63 and R 64 optionally form a ring;
each of Y 3 of formula (2i) and Y 6 of formula (2j) is independently CR 65 R 66 , NR 67 , a sulfur atom, an oxygen atom, or a nitrogen atom to be bonded to L 20 ;
X 4 of formula (2j) is the same as X 20 of formula (20); and
each of R 63 to R 67 is independently as R 8 to R 16 are defined.

6. The organic electroluminescence device according to claim 5 , wherein HAr is a group according to formula (2b) or a group according to formula (2bx):

where:
X 2 is as defined in formula (2B);
each of R 17 , R 18 , and Ar 4 is independently as R 8 to R 16 are defined;
c and d are 4; and
adjacent ones of R 17 optionally form a ring and adjacent ones of R 18 optionally form a r

Assignees

• Idemitsu Kosan Co

Inventors

• Kawamura Masahiro
• Mizuki Yumiko
• Ogiwara Toshinari
• Kuma Hitoshi

Classifications

• H01L2251/308

  Electricity · mapped topic

• C07D471/04

  Ortho-condensed systems · CPC title

• C07D417/14

  containing three or more hetero rings · CPC title

• C09K2211/1033

  with oxygen · CPC title

• C09K11/025

  non-luminescent particle coatings or suspension media · CPC title