Organic electroluminescent element, electronic device and compound

Patent metadata

Field	Value
Publication number	US-2018053901-A1
Application number	US-201615557681-A
Country	US
Kind code	A1
Filing date	Mar 18, 2016
Priority date	Mar 27, 2015
Publication date	Feb 22, 2018
Grant date	—

Abstract

An organic electroluminescence device includes an anode, an emitting layer, and a cathode, the emitting layer including a delayed-fluorescent first compound represented by a formula (1), and a fluorescent second compound. In the formula (1), Ar 1 is a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms and the like, and Ar EWG is a substituted or unsubstituted heteroaryl group having 5 to 30 ring atoms and including one or more nitrogen atom in the ring, or an aryl group having 6 to 30 ring carbon atoms and substituted by one or more cyano group, at least one of Ar 1 and Ar X being at least one group selected from the group consisting of groups represented by a formula (1a) and the like.

First claim

1 : An organic electroluminescence device comprising:
an anode; an emitting layer; and a cathode, wherein the emitting layer comprises a delayed-fluorescent first compound represented by a formula (1) and a fluorescent second compound,

wherein:
Ar 1 is a group selected from the group consisting of a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, a substituted or unsubstituted heteroaryl group having 5 to 30 ring atoms, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted fluoroalkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 ring carbon atoms, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, a substituted phosphoryl group, a substituted silyl group, a cyano group, a nitro group, a carboxy group, and groups represented by formulae (1a) to (1j);
Ar EWG is a substituted or unsubstituted heteroaryl group having 5 to 30 ring atoms which has one or more nitrogen atom in the ring, or an aryl group having 6 to 30 ring carbon atoms and substituted by one or more cyano group;
Ar X is each independently a hydrogen atom or a substituent, and Arx as a substituent is a group selected from the group consisting of a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, a substituted or unsubstituted heteroaryl group having 5 to 30 ring atoms, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted fluoroalkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 ring carbon atoms, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, a substituted phosphoryl group, a substituted silyl group, a cyano group, a nitro group, a carboxy group, and the groups represented by the formulae (1a) to (1j);
n represents an integer ranging from 0 to 5;
when n is 2 or more, a plurality of Arxs are mutually the same or different;
the ring (A) is a five-membered ring, a six-membered ring, or a seven-membered ring;
at least one of Ar 1 and Ar X is a group selected from the group consisting of groups represented by the formulae (1a) to (1j):

wherein, in the formulae (1a) to (1j): X 1 to X 20 are each independently N or C-Rx; with a proviso that:
in the formula (1b), one of X 5 to X 8 is a carbon atom bonded to one of X 9 to X 12 , and one of X 9 to X 12 is a carbon atom bonded to one of X 5 to X 8 ;
in the formula (1c), one of X 5 to X 8 is a carbon atom bonded to the nitrogen atom in the ring comprising A 2 ;
in the formula (1e), one of X 5 to X 8 and X 18 is a carbon atom bonded to one of X 9 to X 12 , and one of X 9 to X 12 is a carbon atom bonded to one of X 5 to X 8 and X 18 ;
in the formula (1f), one of X 5 to X 8 and X 18 is a carbon atom bonded to one of X 9 to X 12 and X 19 and one of X 9 to X 12 , and X 19 is a carbon atom bonded to one of X 5 to X 8 and X 18 ;
in the formula (1g), one of X 5 to X 8 is a carbon atom bonded to one of X 9 to X 12 and X 19 , and one of X 9 to X 12 and X 19 is a carbon atom bonded to one of X 5 to X 8 ;
in the formula (1h), one of X 5 to X 8 and X 18 is a carbon atom bonded to the nitrogen atom in the ring comprising A 2 ;
in the formula (1i), one of X 5 to X 8 and X 18 is a carbon atom bonded to the nitrogen atom connecting the ring comprising X 9 to X 12 and X 19 and the ring comprising X 13 to X 16 and X 20 ;
in the formula (1j), one of X 5 to X 8 is a carbon atom bonded to the nitrogen atom connecting the ring comprising X 9 to X 12 and X 19 and the ring comprising X 13 to X 16 and X 20 ;
R X is each independently a hydrogen atom or a substituent, and Rx as a substituent is a group selected from the group consisting of a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, a substituted or unsubstituted heteroaryl group having 5 to 30 ring atoms, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted fluoroalkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 ring carbon atoms, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, a substituted phosphoryl group, a substituted silyl group, a cyano group, a nitro group, and a carboxy group;
a plurality of Rxs as substituents are mutually the same or different; the plurality of Rxs as the substituents are directly bonded to each other to form a ring, are bonded via a hetero atom to form a ring, or do not form a ring;
A 1 and A 2 are each independently a single bond, O, S, C(R 1 )(R 2 ), Si(R 3 )(R 4 ), C(═O) S(═O), SO 2 or N(R 5 );
R 1 to R 5 are each independently a hydrogen atom or a substituent, and R 1 to R 5 as substituents are groups selected from the group consisting of a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, a substituted or unsubstituted heteroaryl group having 5 to 30 ring atoms, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted fluoroalkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 ring carbon atoms, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, a substituted phosphoryl group, a substituted silyl group, a cyano group, a nitro group, and a carboxy group; and
Ara is a group selected from the group consisting of a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, a substituted or unsubstituted heteroaryl group having 5 to 30 ring atoms, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted fluoroalkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 ring carbon atoms, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, a substituted phosphoryl group, and a substituted silyl group.

2 : The organic electroluminescence device according to claim 1 , wherein
the first compound is represented by a formula (10),

wherein:
Y 1 to Y 5 are each independently N, C—CN or C-Ry, at least one of Y 1 to Y 5 being N or C—CN:
Ry is each independently a hydrogen atom or a substituent, and Ry as a substituent is a group selected from the group consisting of a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, a substituted or unsubstituted heteroaryl group having 5 to 30 ring atoms, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted fluoroalkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 ring carbon atoms, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, a substituted phosphoryl group, a substituted silyl group, a cyano group, a nitro group, and a carboxy group;
A plurality of R y s are mutually the same or different;
Ar 1 is a group selected from the group consisting of a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, a substituted or unsubstituted heteroaryl group having 5 to 30 ring atoms, a substituted or unsubstituted alkyl group having 1 to

Assignees

• Idemitsu Kosan Co

Inventors

• Yoshida Kei
• Hashimoto Ryohei
• Ogiwara Toshinari
• Kawamura Yuichiro
• Saito Masatoshi

Classifications

• C09K2211/1007

  Non-condensed systems · CPC title

• C09K11/06

  containing organic luminescent materials · CPC title

• C09K2211/1018

  Heterocyclic compounds · CPC title

• C07D403/14

  containing three or more hetero rings · CPC title

• C07D403/10 Primary

  linked by a carbon chain containing aromatic rings · CPC title