Carbazole compound and organic light-emitting device including the same

Patent metadata

Field	Value
Publication number	US-9812653-B2
Application number	US-201414550518-A
Country	US
Kind code	B2
Filing date	Nov 21, 2014
Priority date	Nov 28, 2013
Publication date	Nov 7, 2017
Grant date	Nov 7, 2017

Abstract

A carbazole compound represented by Formula 1:

wherein in Formula 1, groups and variables are the same as defined in the specification.

First claim

What is claimed is:

1. A carbazole compound represented by Formula 1:

wherein in Formula 1,
X 1 is selected from N-[(L 11 ) a11 -(R 11 ) b11 ], S, O, S(═O), S(═O) 2 , C(R 12 )(R 13 ), and Si(R 12 )(R 13 );
L 1 , L 2 , and L 11 are each independently selected from a substituted or unsubstituted C 1 -C 60 alkylene group, a substituted or unsubstituted C 2 -C 60 alkenylene group, a substituted or unsubstituted C 2 -C 60 alkynylene group, a substituted or unsubstituted C 3 -C 10 cycloalkylene group, a substituted or unsubstituted C 2 -C 10 heterocycloalkylene group, a substituted or unsubstituted C 3 -C 10 cycloalkenylene group, a substituted or unsubstituted C 2 -C 10 heterocycloalkenylene group, a substituted or unsubstituted C 6 -C 60 arylene group, a substituted or unsubstituted C 2 -C 60 heteroarylene group, a substituted or unsubstituted divalent non-aromatic condensed polycyclic group, and a substituted or unsubstituted divalent non-aromatic hetero-condensed polycyclic group;
a1 and a2 are each independently an integer selected from 1 to 5;
a11 is an integer selected from 0 to 5;
R 1 is selected from
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, —C(═O)—O-Q 1 , —C(═O)-Q 2 , 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; and
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 group 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, —C(═O)—O-Q 3 , —C(═O)-Q 4 , a sulfonic acid group or a salt thereof, and a phosphoric acid group or a salt thereof;
R 2 to R 4 and R 11 to R 13 are each independently selected from 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, —C(═O)—O-Q 11 , —C(═O)-Q 12 , 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 3 -C 10 cycloalkyl group, a substituted or unsubstituted C 2 -C 10 heterocycloalkyl group, a substituted or unsubstituted C 3 -C 10 cycloalkenyl group, a substituted or unsubstituted C 2 -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 7 -C 60 arylalkyl group, a substituted or unsubstituted C 2 -C 60 heteroaryl group, a substituted or unsubstituted C 2 -C 60 heteroaryloxy group, a substituted or unsubstituted C 2 -C 60 heteroarylthio group, a substituted or unsubstituted C 3 -C 60 heteroarylalkyl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, and a substituted or unsubstituted monovalent non-aromatic heterocondensed polycyclic group, —N(Q 13 )(Q 14 ), —Si(Q 15 )(Q 16 )(Q 17 ), and —B(Q 18 )(Q 19 );
b1 and b3 are each independently an integer selected from 1 to 4;
b2, b4, and b11 are each independently an integer selected from 1 to 3;
E 1 is an electron transporting-cyclic group containing at least one nitrogen as a ring-forming atom and substituted with at least one Ar 1 ,
wherein Ar 1 is selected from a substituted or unsubstituted C 3 -C 10 cycloalkyl group, a substituted or unsubstituted C 2 -C 10 heterocycloalkyl group, a substituted or unsubstituted C 3 -C 10 cycloalkenyl group, a substituted or unsubstituted C 2 -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 7 -C 60 arylalkyl group, a substituted or unsubstituted C 2 -C 60 heteroaryl group, a substituted or unsubstituted C 2 -C 60 heteroaryloxy group, a substituted or unsubstituted C 2 -C 60 heteroarylthio group, a substituted or unsubstituted C 3 -C 60 heteroarylalkyl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, and a substituted or unsubstituted monovalent non-aromatic heterocondensed polycyclic group; and
at least one substituent of the substituted C 1 -C 60 alkylene group, the substituted C 2 -C 60 alkenylene group, the substituted C 2 -C 60 alkynylene group, the substituted C 3 -C 10 cycloalkylene group, the substituted C 2 -C 10 heterocycloalkylene group, the substituted C 3 -C 10 cycloalkenylene group, the substituted C 2 -C 10 heterocycloalkenylene group, the substituted C 6 -C 60 arylene group, the substituted C 2 -C 60 heteroarylene group, the substituted divalent non-aromatic condensed polycyclic group, the substituted divalent non-aromatic hetero-condensed polycyclic group, the substituted C 1 -C 60 alkyl group, the substituted C 2 -C 60 alkenyl group, the substituted C 2 -C 60 alkynyl group, the substituted C 3 -C 10 cycloalkyl group, the substituted C 2 -C 10 heterocycloalkyl group, the substituted C 3 -C 10 cycloalkenyl group, the substituted C 2 -C 10 heterocycloalkenyl group, the substituted C 6 -C 60 aryl group, the substituted C 6 -C 60 aryloxy group, the substituted C 6 -C 60 arylthio group, a substituted or unsubstituted C 7 -C 60 arylalkyl group, the substituted C 2 -C 60 heteroaryl group, a substituted or unsubstituted C 2 -C 60 heteroaryloxy group, a substituted or unsubstituted C 2 -C 60 heteroarylthio group, a substituted or unsubstituted C 3 -C 60 heteroarylalkyl group, the substituted monovalent non-aromatic condensed polycyclic group, and the substituted monovalent non-aromatic heterocondensed polycyclic 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 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 group 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 3 -C 10 cycloalkyl group, a C 2 -C 10 heterocycloalkyl group, a C 3 -C 10 cycloalkenyl group, a C 2 -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 substituted or unsubstituted C 7 -C 60 arylalkyl group, a C 2 -C 60 heteroaryl group, a substituted or unsubstituted C 2 -C 60 heteroaryloxy group, a substituted or unsubstituted C 2 -C 60 heteroarylthio group, a substituted or unsubstituted C 3 -C 60 heteroarylalkyl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic heterocondensed polycyclic group, —N(Q 21 )(Q 22 ), —

Assignees

• Samsung Electronics Co Ltd
• Samsung Sdi Co Ltd

Inventors

• Jung Yongsik
• Son Jhunmo
• Lee Seungjae
• Kim Youngkwon
• Kim Hyungsun
• Chung Yeonsook

Classifications

• H01L51/5016

  Electricity · mapped topic

• C09K2211/1491

  containing other combinations of heteroatoms · CPC title

• C07D401/14 Primary

  containing three or more hetero rings · CPC title

• C09K2211/1483

  containing nitrogen and sulfur as heteroatoms · CPC title

• C09K2211/1416

  Condensed systems · CPC title