Condensed-cyclic compound and organic light-emitting diode comprising the same

Patent metadata

Field	Value
Publication number	US-9853222-B2
Application number	US-201313973831-A
Country	US
Kind code	B2
Filing date	Aug 22, 2013
Priority date	Mar 27, 2013
Publication date	Dec 26, 2017
Grant date	Dec 26, 2017

Abstract

A condensed-cyclic compound is represented by Formula 1, and an organic light-emitting diode includes the condensed-cyclic compound. The organic light-emitting diode includes a first electrode, a second electrode facing the first electrode, and an organic layer. The organic layer includes an emission layer and the condensed-cyclic compound. The condensed-cyclic compound can be included in the emission layer as a host, and the emission layer may further include a dopant.

First claim

What is claimed is:

1. A condensed-cyclic compound represented by Formula 1:

wherein:
ring A 1 , ring A 2 , and ring A 3 are condensed with each other;
ring A 2 is represented by Formula 2, wherein Y1 is N-(L 1 ) aa -(R 11 ) ab ;
ring A 1 , ring A 3 , ring A 4 , and ring A 5 are each independently a substituted or unsubstituted benzene ring or a substituted or unsubstituted naphthalene ring;
R 1 and R 2 are each independently a hydrogen, a deuterium, a halogen atom, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine, a hydrazone, a carboxyl group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a substituted or unsubstituted C 1 -C 60 alkyl group, a substituted or unsubstituted C 2 -C 60 alkenyl group, a substituted or unsubstituted C 2 -C 60 alkynyl group, a substituted or unsubstituted C 1 -C 60 alkoxy group, a substituted or unsubstituted C 3 -C 60 cycloalkyl group, a substituted or unsubstituted C 3 -C 60 cycloalkenyl group, a substituted or unsubstituted C 6 -C 60 aryl group, a substituted or unsubstituted C 6 -C 60 aryloxy group, a substituted or unsubstituted C 6 -C 60 arylthio group, or a substituted or unsubstituted C 2 -C 60 heteroaryl group, wherein R 1 and R 2 are non-ring forming substituents which are not linked to each other and do not form a ring;
L 1 is a substituted or unsubstituted C 6 -C 60 arylene group or a substituted or unsubstituted C 2 -C 60 heteroarylene group;
aa is an integer of 0 to 5;
R 11 is a substituted or unsubstituted 5-membered hetero ring, or a substituted or unsubstituted 6-membered hetero ring in which at least one ring-forming atom is nitrogen (N); and
ab is an integer of 1 to 10.

2. The condensed-cyclic compound of claim 1 , wherein the condensed-cyclic compound is represented by Formula 3 or 4:

wherein C 1 to C 10 indicate distinct carbon atoms.

3. The condensed-cyclic compound of claim 2 , wherein the ring A 1 is represented by one of Formulae 5(1) and 5(2), the ring A 3 is represented by one of Formulae 6(1) to 6(4), the ring A 4 is represented by one of Formulae 7(1) to 7(4), and the ring A 5 is represented by one of Formulae 8(1) to 8(4):

wherein:
R 21 to R 24 are each independently a hydrogen, a deuterium, a halogen atom, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine, a hydrazone, a carboxyl group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a substituted or unsubstituted C 1 -C 60 alkyl group, a substituted or unsubstituted C 2 -C 60 alkenyl group, a substituted or unsubstituted C 2 -C 60 alkynyl group, a substituted or unsubstituted C 2 -C 60 alkoxy group, a substituted or unsubstituted C 3 -C 60 cycloalkyl group, a substituted or unsubstituted C 3 -C 60 cycloalkenyl group, a substituted or unsubstituted C 6 -C 60 aryl group, a substituted or unsubstituted C 6 -C 60 aryloxy group, a substituted or unsubstituted C 6 -C 60 arylthio group, a substituted or unsubstituted C 2 -C 60 heteroaryl group, or -(L 2 ) ao -(R 12 ) ap ;
ac is 1 or 2;
ag is an integer of 1 to 3;
ae and ai are each independently an integer of 1 to 4;
ah is an integer of 1 to 5;
af and aj are each independently an integer of 1 to 6;
L 2 is a substituted or unsubstituted C 6 -C 60 arylene group or a substituted or unsubstituted C 2 -C 60 heteroarylene group;
ao is an integer of 0 to 5;
R 12 is a substituted or unsubstituted C 3 -C 60 cycloalkyl group, a substituted or unsubstituted C 3 -C 60 cycloalkenyl group, a substituted or unsubstituted C 6 -C 60 aryl group, or a substituted or unsubstituted C 2 -C 60 heteroaryl group; and
ap is an integer of 1 to 10.

4. The condensed-cyclic compound of claim 3 , wherein R 21 to R 24 are each independently:
a hydrogen, a deuterium, a halogen atom, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine, a hydrazone, a carboxyl group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C 1 -C 20 alkyl group, or a C 1 -C 20 alkoxy group; or
a C 1 -C 20 alkyl group or a C 1 -C 20 alkoxy group substituted with at least one of a deuterium atom, a halogen atom, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine, a hydrazone, a carboxyl group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a phenyl group, a naphthyl group, or an anthracenyl group; or
a C 6 -C 14 aryl group or a C 2 -C 14 heteroaryl group; or
a C 6 -C 14 aryl group or a C 2 -C 14 heteroaryl group substituted with at least one of a deuterium atom, a halogen atom, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine, a hydrazone, a carboxyl group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C 1 -C 20 alkyl group, a C 1 -C 20 alkoxy group, a phenyl group, a naphthyl group, or an anthracenyl group; or
-(L 2 ) ao (R 12 ) ap ,
wherein:
L 2 is a substituted or unsubstituted phenylene group, a substituted or unsubstituted pentalenylene group, a substituted or unsubstituted indenylene group, a substituted or unsubstituted naphthylene group, a substituted or unsubstituted azulenylene group, a substituted or unsubstituted heptalenylene group, a substituted or unsubstituted indacenylene group, a substituted or unsubstituted acenaphthylene group, a substituted or unsubstituted fluorenylene group, a substituted or unsubstituted spiro-fluorenyl group, a substituted or unsubstituted phenalenylene group, a substituted or unsubstituted phenanthrenylene group, a substituted or unsubstituted anthracenylene group, a substituted or unsubstituted fluoranthenylene group, a substituted or unsubstituted triphenylenylene group, a substituted or unsubstituted pyrenylene group, a substituted or unsubstituted chrysenylene group, a substituted or unsubstituted naphthacenylene group, a substituted or unsubstituted picenylene group, a substituted or unsubstituted perylenylene group, a substituted or unsubstituted pentaphenylene group, or a substituted or unsubstituted hexacenylene group;
ao is 0, 1, or 2;
R 12 is a substituted or unsubstituted 5-membered hetero ring, a substituted or unsubstituted 6-membered hetero ring, a substituted or unsubstituted 9-membered hetero ring, or a substituted or unsubstituted 10-membered hetero ring, in which at least one ring-forming atom is nitrogen (N); and
ap is 1 or 2.

5. The condensed-cyclic compound of claim 4 , wherein R 21 to R 24 are each independently:
a hydrogen, a deuterium, a halogen atom, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine, a hydrazone, a carboxyl group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a methyl group, an ethyl group, a propyl group, a butyl group, a pentyl group, a hexyl group, a heptyl group, an octyl group, a methoxy group, an ethoxy group, a propoxy group, a butoxy group, or a pentoxy group; or
a methyl group, an ethyl group, a pr

Assignees

• Samsung Display Co Ltd

Inventors

• Kim Se-Hun
• Kim Mi-Kyung
• Lee Kwan-Hee
• Chu Chang-Woong

Classifications

• C09K2211/1044

  containing two nitrogen atoms as heteroatoms · CPC title

• C09B57/00

  Other synthetic dyes of known constitution · CPC title

• H01L51/0061

  Electricity · mapped topic

• H01L51/0067

  Electricity · mapped topic

• C07D491/16

  Peri-condensed systems · CPC title