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

Patent metadata

Field	Value
Publication number	US-9960365-B2
Application number	US-201514688434-A
Country	US
Kind code	B2
Filing date	Apr 16, 2015
Priority date	Sep 26, 2014
Publication date	May 1, 2018
Grant date	May 1, 2018

Abstract

A condensed cyclic compound represented by Formula 1:

wherein in Formula 1, groups L 1 and X 1 to X 16 are the same as described in the specification.

First claim

What is claimed is:

1. A condensed cyclic compound represented by Formula 1:

wherein in Formula 1,
L 1 is selected from a phenylene group, a pyridinylene group, a pyrimidinylene group, and a triazinylene group;
X 1 is N or CR 1 ;
X 2 is N or CR 2 ;
X 3 is N or CR 3 ;
X 4 is N or CR 4 ;
X 5 is N or CR 5 ;
X 6 is N or CR 6 ;
X 7 is N or CR 7 ;
X 8 is N or CR 8 ;
X 9 is N or CR 9 ;
X 10 is N or CR 10 ;
X 11 is N or CR 11 ;
X 12 is N or CR 12 ;
X 13 is N or CR 13 ;
X 14 is N or CR 14 ;
X 15 is N or CR 15 ;
X 16 is N or CR 16 ;
R 1 to R 16 are each independently selected from R ET , a hydrogen, a deuterium, —F, —Cl, —Br, —I, 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 1 -C 60 alkoxy group, a substituted or unsubstituted C 3 -C 10 cycloalkyl 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, and a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group;
at least one selected from X 1 to X 16 is CR ET ;
R ET is represented by any one of Formulae 2-1 to 2-8:

wherein in Formulae 2-1 to 2-8,
R 21 and R 22 are each independently selected from a substituted C 1 -C 60 alkyl group, a substituted C 1 -C 60 alkoxy group, a substituted C 3 -C 10 cycloalkyl group, a substituted or unsubstituted C 6 -C 60 aryl group, a substituted C 6 -C 60 aryloxy group, a substituted C 6 -C 60 arylthio group, a substituted unsubstituted C 1 -C 60 heteroaryl group, a substituted monovalent non-aromatic condensed polycyclic group, and a substituted monovalent non-aromatic condensed heteropolycyclic group;
* indicates a binding site to a neighboring atom, and
at least one of substituents of the substituted C 1 -C 60 alkyl group, substituted C 1 -C 60 alkoxy group, substituted C 3 -C 10 cycloalkyl 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
a deuterium, —F, —Cl, —Br, —I, 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 1 -C 60 alkenyl group, a C 1 -C 60 alkynyl group, and a C 1 -C 60 alkoxy group, each substituted with at least one selected from deuterium, —F, —Cl, —Br, —I, 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, and —Si(Q 11 )(Q 12 )(Q 13 );
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 a deuterium, —F, —Cl, —Br, —I, 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 1 -C 60 alkenyl group, a C 1 -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, and —Si(Q 21 )(Q 22 )(Q 23 ); and
—Si(Q 31 )(Q 32 )(Q 33 ),
wherein Q 11 to Q 13 , Q 21 to Q 23 and Q 31 to Q 33 are each independently selected from a C 1 -C 60 alkyl group, a C 6 -C 60 aryl group, a C 1 -C 60 heteroaryl group, a monovalent non-aromatic condensed polycyclic group, and a monovalent non-aromatic condensed heteropolycyclic group.

2. The condensed cyclic compound of claim 1 , wherein
L 1 is selected from Formulae 3-1 to 3-14;

wherein in Formulae 3-1 to 3-14,
* and *′ indicate each independently a binding site to a neighboring atom.

3. The condensed cyclic compound of claim 1 , wherein
L 1 is selected from Formulae 3-2, 3-5, 3-6, 3-7, 3-11, 3-12, and 3-14:

wherein in Formulae 3-2, 3-5, 3-6, 3-7, 3-11, 3-12, and 3-14,
* and *′ indicate each independently a binding site to a neighboring atom.

4. The condensed cyclic compound of claim 1 , wherein
X 1 is CR 1 X 2 is CR 2 ; X 3 is CR 3 ; X 4 is CR 4 ; X 5 is CR 5 ; X 6 is CR 6 ; X 7 is CR 7 ; X 8 is CR 8 ; X 9 is CR 9 ; X 10 is CR 10 ; X 11 is CR 11 ; X 12 is CR 12 ; X 13 is CR 13 ; X 14 is CR 14 ; X 15 is CR 15 ; and X 16 is CR 16 , or
X 1 is N; X 2 is CR 2 ; X 3 is CR 3 ; X 4 is CR 4 ; X 5 is CR 5 ; X 6 is CR 6 ; X 7 is CR 7 ; X 8 is CR 8 ; X 9 is CR 9 ; X 10 is CR 10 ; X 11 is CR 11 ; X 12 is CR 12 ; X 13 is CR 13 ; X 14 is CR 14 ; X 15 is CR 15 ; and X 16 is CR 16 , or
X 1 is CR 1 ; X 2 is N; X 3 is CR 3 ; X 4 is CR 4 ; X 5 is CR 5 ; X 6 is CR 6 ; X 7 is CR 7 ; X 8 is CR 8 ; X 9 is CR 9 ; X 10 is CR 10 ; X 11 is CR 11 ; X 12 is CR 12 ; X 13 is CR 13 ; X 14 is CR 14 ; X 15 is CR 15 ; and X 16 is CR 16 , or
X 1

Assignees

• Samsung Electronics Co Ltd
• Samsung Sdi Co Ltd

Inventors

• Jeon Soonok
• Son Jhunmo
• Kim Sangmo
• Kim Hyunjung
• Jung Yeonsook
• Jung Yongsik
• Huh Dalho

Classifications

• C09K2211/1074

  containing more than three nitrogen atoms as heteroatoms · CPC title

• H01L51/5016

  Electricity · mapped topic

• H01L51/0067

  Electricity · mapped topic

• H01L51/0085

  Electricity · mapped topic

• H01L51/0072 Primary

  Electricity · mapped topic