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

Patent metadata

Field	Value
Publication number	US-2016308144-A1
Application number	US-201514941417-A
Country	US
Kind code	A1
Filing date	Nov 13, 2015
Priority date	Apr 16, 2015
Publication date	Oct 20, 2016
Grant date	—

Abstract

An organic light-emitting device includes: a first electrode; a second electrode facing the first electrode; and an organic layer between the first electrode and the second electrode, the organic layer including an emission layer, and further including at least one condensed cyclic compound of Formula 1. The organic light-emitting device may have high efficiency and a long lifespan.

First claim

What is claimed is:

1 . A condensed cyclic compound represented by Formula 1:

wherein, in Formula 1,
C 1 to C 4 each independently represent chemically distinct carbon atoms,
ring A 1 is represented by one selected from Formulae 2A and 2B,
ring A 2 is represented by one selected from Formulae 2C and 2D,
X 1 is selected from N-(L 1 ) a1 -(Ar 1 ) b1 , O, and S, and X 2 is selected from N-(L 2 ) a2 -(Ar 2 ) b2 , O, and S,
L 1 , L 2 , L 21 , and L 22 are each independently selected from a substituted or unsubstituted C 3 -C 10 cycloalkylene group, a substituted or unsubstituted C 1 -C 10 heterocycloalkylene group, a substituted or unsubstituted C 3 -C 10 cycloalkenylene group, a substituted or unsubstituted C 1 -C 10 heterocycloalkenylene group, a substituted or unsubstituted C 6 -C 60 arylene group, a substituted or unsubstituted C 1 -C 60 heteroarylene group, a substituted or unsubstituted divalent non-aromatic condensed polycyclic group, and a substituted or unsubstituted divalent non-aromatic condensed heteropolycyclic group,
a1, a2, a21, and a22 are each independently selected from 0, 1, 2, and 3, and when a1 is 2 or more, two or more Li(s) are identical to or different from each other, when a2 is 2 or more, two or more L 2 (s) are identical to or different from each other, when a21 is 2 or more, two or more L 21 (s) are identical to or different from each other, and when a22 is 2 or more, two or more L 22 (s) are identical to or different from each other,
Ar 1 and Ar 2 are each independently selected from a substituted or unsubstituted C 6 -C 60 aryl group, a substituted or unsubstituted C 1 -C 60 heteroaryl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, and a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group,
when X 1 is N-(L 1 ) a1 -(Ar 1 ) b1 and X 2 is N-(L 2 ) a2 -(Ar 2 ) b2 , at least one of Ar 1 and Ar 2 is selected from a substituted or unsubstituted C 1 -C 60 heteroaryl group and a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group,
b1 and b2 are each independently selected from 1, 2, and 3, and when b1 is 2 or more, two or more Ar 1 (s) are identical to or different from each other, and when b2 is 2 or more, two or more Ar 2 (s) are identical to or different from each other,
R 21 and R 22 are each independently selected from hydrogen, deuterium, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid 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 10 cycloalkyl group, a substituted or unsubstituted C 1 -C 10 heterocycloalkyl group, a substituted or unsubstituted C 3 -C 10 cycloalkenyl group, a substituted or unsubstituted C 1 -C 10 heterocycloalkenyl 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 1 -C 60 heteroaryl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, —Si(Q 1 )(Q 2 )(Q 3 ), —B(Q 4 )(Q 5 ), and N(Q 6 )(Q 7 ),
b21 and b22 are each independently selected from 0, 1, 2, and 3, and when b21 is 2 or more, two or more R 21 (s) are identical to or different from each other, and when b22 is 2 or more, two or more R 22 (s) are identical to or different from each other,
c21 and c22 are each independently selected from 0, 1, 2, 3, 4, 5, and 6, and when c21 is 2 or more, two or more *-[(L 21 ) a21 -(R 21 ) b21 ](s) are identical to or different from each other, and when c22 is 2 or more, two or more *-[(L 22 ) a22 -(R 22 ) b22 ](s) are identical to or different from each other, and
at least one substituent of the substituted C 1 -C 60 alkyl group, substituted C 2 -C 60 alkenyl group, substituted C 2 -C 60 alkynyl group, substituted C 1 -C 60 alkoxy group, substituted C 3 -C 10 cycloalkyl group, substituted C 1 -C 10 heterocycloalkyl group, substituted C 3 -C 10 cycloalkenyl group, substituted C 1 -C 10 heterocycloalkenyl group, substituted C 6 -C 60 aryl group, substituted C 6 -C 60 aryloxy group, substituted C 6 -C 60 arylthio group, substituted C 1 -C 60 heteroaryl group, substituted monovalent non-aromatic condensed polycyclic group, and substituted monovalent non-aromatic condensed heteropolycyclic group is selected from:
deuterium, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid 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 60 alkyl group, a C 2 -C 60 alkenyl group, a C 2 -C 60 alkynyl group, and a C 1 -C 60 alkoxy group;
a C 1 -C 60 alkyl group, a C 2 -C 60 alkenyl group, a C 2 -C 60 alkynyl group, and a C 1 -C 60 alkoxy group, each substituted with at least one selected from deuterium, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C 3 -C 10 cycloalkyl group, a C 1 -C 10 heterocycloalkyl group, a C 3 -C 10 cycloalkenyl group, a C 1 -C 10 heterocycloalkenyl group, a C 6 -C 60 aryl group, a C 6 -C 60 aryloxy group, a C 6 -C 60 arylthio group, a C 1 -C 60 heteroaryl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, —Si(Q 11 )(Q 12 )(Q 13 ), —B(Q 14 )(Q 15 ), and —N(Q 16 )(Q 17 );
a C 3 -C 10 cycloalkyl group, a C 1 -C 10 heterocycloalkyl group, a C 3 -C 10 cycloalkenyl group, a C 1 -C 10 heterocycloalkenyl group, a C 6 -C 60 aryl group, a C 6 -C 60 aryloxy group, a C 6 -C 60 arylthio group, a C 1 -C 60 heteroaryl group, a monovalent non-aromatic condensed polycyclic group, and a monovalent non-aromatic condensed heteropolycyclic group;
a C 3 -C 10 cycloalkyl group, a C 1 -C 10 heterocycloalkyl group, a C 3 -C 10 cycloalkenyl group, a C 1 -C 10 heterocycloalkenyl group, a C 6 -C 60 aryl group, a C 6 -C 60 aryloxy group, a C 6 -C 60 arylthio group, a C 1 -C 60 heteroaryl group, a monovalent non-aromatic condensed polycyclic group, and a monovalent non-aromatic condensed heteropolycyclic group, each substituted with at least one selected from deuterium, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid 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 60 alkyl group, a C 2 -C 60 alkenyl group, a C 2 -C 60 alkynyl group, a C 1 -C 60 alkoxy group, a C 3 -C 10 cycloalkyl group, a C 1 -C 10 heterocycloalkyl group, a C 3 -C 10 cycloalkenyl group, a C 1 -C 10 heterocycloalkenyl group, a C 6 -C 60 aryl group, a C 6 -C 60 aryloxy group, a C 6 -C 60 arylthio group, a C 1 -C 60 heteroaryl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, —Si(Q 21 )(Q 22 )(Q 23 ), —B(Q 24 )(Q 25 ), and —N(Q 26 )(Q 27 ); and
—Si(Q 31 )(Q 32

Assignees

• Samsung Display Co Ltd

Inventors

• Lee Jungsub

Classifications

• C07D405/14

  containing three or more hetero rings · CPC title

• C09K2211/1059

  containing three nitrogen atoms as heteroatoms · CPC title

• C09K11/06

  containing organic luminescent materials · CPC title

• C09K2211/1044

  containing two nitrogen atoms as heteroatoms · CPC title

• C09K2211/1022

  bridged by heteroatoms, e.g. N, P, Si or B · CPC title